how to professionally say “I told you so”

A reader writes:

I work at a small-ish company in a creative industry that has a lot of issues with changing/inconsistent expectations and management that isn’t in the habit of really listening to employee feedback. My direct manager and grandboss also have a habit of saying one thing in team trainings and then doing the complete opposite in practice. (Yes, I’m aware these are issues on their own, and I’m job searching.)

A while back we had a team training about red flags to look for in new projects, in which they stressed that there are some projects that aren’t worth seeing through if they’re going to cause more stress than they’re worth and/or take away our ability to give enough attention to other more successful projects.

Not too long after that, I began working on a project that had a lot of red flags from the very beginning. I brought up these concerns with my manager, saying that this felt like one of those projects where it’s better to cut your losses early, as the problems I was noticing (most of which were with outside creatives we’d be collaborating with) were likely to only compound and cause more chaos the longer I worked on it. I mentioned this several times, saying that I thought it would get worse, and that I thought it’d be a better use of my time to cancel this project and move on to another one. Every time, my manager said to give the outside creatives “one more chance” (I’ve lost track of how many “one last chances” they’ve gotten at this point), and we ended up signing contracts and officially moving forward with the project. I don’t have the authority to decide if these projects should get officially greenlit or canceled, so I had to just go with it.

Well, as I bet you’ve predicted, we’re several months into this project, and every concern I had has continued to be an issue. We’ve had to adjust the timeline for this project many times (which negatively affects other departments at our company), and I’ve dealt with issue after issue with the people we contracted with (without whom the project simply cannot be done) — missed deadlines, shoddy work, weeks and weeks of no communication, etc. It’s been incredibly frustrating for me, and I have no desire to work on this project or with these people ever again.

Where I need advice, I suppose, is in what to do if/when my manager talks to me about their concerns about how poorly the project is going and how many times we’ve had to readjust schedules and the like. They’ve been known to do this — subtly blaming employees when a project isn’t going well for reasons outside their control. Somehow it’s our fault if freelancers or other contracted individuals ignore our emails or turn in work that’s not in line with what we contracted them for or have every excuse under the sun for why they can’t meet a deadline they already agreed to. We get a lecture (either as a group or individually) about how we should be better at noticing red flags in the beginning of the process so that we don’t greenlight projects that are just going to end up being a huge pain and don’t end up benefiting the company at all.

But the thing is, as in this situation, my coworkers and I do bring up these concerns and do suggest pulling the plug on projects that aren’t worth the time and effort, and my manager just doesn’t take us seriously. The success of these projects directly affects how much money we make as a company, so we’re made to continue with them, even when they’re hell to work on.

So what am I to do when I get a lecture about “better identifying red flags” in projects so I don’t end up in this situation again? How do I professionally say, “I told you several times that this project was going to end up like this and you didn’t listen to me”? It’s frustrating to feel like my competence at my job is being called into question when the real problem is that my manager doesn’t take my opinion seriously. I know I can’t change the way my manager operates or the issues within the company as a whole, but I do think it’s important for me to be able to professionally and appropriately remind my manager that I’ve raised these concerns.

The key in talking with your boss is to approach it not as “I’m really frustrated that once again you didn’t listen to me and I turned out to be right” (which frames it as personal frustration) but rather as, “I want your thoughts on whether we can handle this business conundrum more effectively in the future.” The latter keeps it work-focused; you’re looking out for the work, not getting into your personal feelings.

That means that if your boss starts lecturing you about how you should have identified the red flags earlier with this project, you could say: “I agree that these are all serious concerns with the project! I had raised XYZ before we started because I was concerned we shouldn’t greenlight it. Since you’re seeing the same things that were worrying me earlier, is there a better way I could have flagged those things originally? From my perspective it seems like I did, so I’m wondering whether I should do something different in how I raise that sort of concern.”

This language allows for the possibility that your boss genuinely sees a piece of this that you don’t. Based on what you wrote, that’s probably not the case — but it’s not impossible. For example, maybe you’ll find out that you weren’t clear enough about the financial consequences you predicted and in the future if you can attach even rough dollar figures, people will pay more attention. Or maybe you’ll learn that you were too vague about why you were skeptical of the contractors and that in the future you shouldn’t pull any punches in describing things that worry you. Or on and on.

But even if it’s nothing like that — even your manager is just trying to duck responsibility and blame you for not doing something you actually did — it’s still helpful to frame it this way because (a) it’s a non-defensive way to point out the stuff you did raise at the beginning, and (b) by asking if you should have done something differently, you’re more likely to nudge your boss into realizing you couldn’t have. That’s not a guaranteed outcome, of course — but it works a lot of the time with at least partly reasonable people.

In fact, rather than wait for your boss to bring it up herself, another option is for you to bring it up proactively. You could say, “I’m concerned about issues XYZ with this project. Since you’ve stressed that we should flag potential problems early so we don’t greenlight projects that end up being problems, I’m curious about whether you’d put this one in that category or whether you think it’s worth continuing with. I’m wondering about whether I should have pushed harder a few months ago when I raised these worries or whether you’re looking at it in a different way than I am.”

Other language that can be useful: “In a situation like that, is there a better way for me to say X?”

Also, if you’re not already putting your concerns in writing before an ill-advised project begins, start doing that. Then if those concerns come to fruition, you can forward that to your boss with a note like, “I’m seeing a lot of the concerns we had in the beginning playing out now, like XYZ. Can we talk about the best way to navigate this at our current stage?” Your tone needs to be collaborative problem-solving, not “I told you so” — but it might drive home the point that you are anticipating these things.

Of course, none of this is a panacea for a boss who’s determined to blame you when they ignored your earlier warnings. But it’s worth a shot to see it improves any of this.

{ 175 comments… read them below }

  1. Chairman of the Bored*

    “I told you several times that this project was going to end up like this and you didn’t listen to me” actually sounds about right to me.

    Definitely put these things in writing, and don’t hesitate to dig those written communications up in the future as needed to prove your claims.

    People are less likely to ignore the warnings of somebody who has a well-established reputation for showing up with receipts after the chickens come home to roost.

    1. Per my previous email*

      Polite disagreement with your last point. Bosses like this never admit they’re wrong and rewrite reality in their heads. They’ll complain that the OP didn’t explain herself clearly enough, or that she told them at a time when she knew they were too busy to pay attention and then didn’t follow up.

      A new job with competent, mature bosses is the only real solution.

      1. Cedrus Libani*

        I agree that you’re unlikely to get a satisfactory response from a boss like this, however the real audience isn’t the boss. You want the other seniors, particularly the boss’ boss, to know who really made the mistake. You also want to make it known that you’re not easily thrown under the bus, such that people don’t try it with you in the future.

        1. Ellie*

          Alison’s response is better though, because it keeps the language positive. Otherwise, you risk the conversation moving on from being about the work issues, to being about your attitude problem instead. As in, ‘you’re right but I don’t like the way you said it so lets focus on that instead’ kind of rubbish. You can still loop the other seniors in.

        2. rebelwithmouseyhair*

          Which is why I would passive-aggressively copy mails in which I point out red flags to the boss’s boss.

      2. kat*

        100% agreed. For your own piece of mind- frame it as ‘this is what leadership is choosing to do.”

      3. ferrina*

        Exactly. I’ve worked for these bosses before, and if there’s one thing they hate, it’s receipts.

        Become a broken record. “I’m concerned about X”. Lodge your complaint, then move on.
        When boss finally agrees with you, say “I absolutely understand. Here’s why you’re right, boss.” List the reasons why the boss is (finally) making the right call, and feel free to say “As you remember, I flagged this, but at the time the strategic decision was to continue with the project.”
        Don’t assign blame. EVER. State the issues neutrally as though this could have happened to anyone.

        This is all about emotional management. You cannot logic or reason your way through an utterly unreasonable boss. You need to diplomatically soothe their ego long enough to get through this and escape. There will be no brilliant speeches or witticisms, no one will clap. But believe me that long after you are gone when they are alone and everything has fallen apart in the face of their incompetence and they can’t sleep in the middle of the night, that self-doubt will creep into their minds, and they will be haunted by the knowledge that that self-doubt is the voice of accuracy.

        Good luck on the job search!

      4. Puggles*

        I used to have a boss like this, told me one way then flip flopped when things didn’t go right and blame me. So I started putting it in writing. I would return to my desk after our conversation and send her a “per our conversation” email and bullet point the instructions she had given me and other pertinent info. I would end the email with “please let me know if you need further clarification or if I misunderstood anything”. This solution worked! She stopped blaming and gaslighting me.

        1. Overit*

          Yes. I was forced to do that and it worked. I actually printed out all of my emails and kept them in a paper folder because Boss liked to come to my desk to scream at me in front of others. When I would try to respond with reference to my emails she would insist it was too much trouble to check her email. So I would get out my folder and literally lay the printed emails out, saying, “Oh let me be of assistance” in an utterly bland tone.
          Not being too bright, it took her a few times to realize that she needed a different game plan with me. But she did. And it gave me some breathing room until I could quit.

        2. Reluctant Mezzo*

          I started that when one boss told me to do something and then asked, ‘why did you do that?’ She somehow had a better memory once we decided on things with emails–maybe she just processed stuff better when she saw it in print.

      5. My Useless 2 Cents*

        I think this is why I don’t really agree with Alison’s advise on this one. By bringing up the possibility that you could do something different in the future means you didn’t do what you could in the past to point out the red flags. Therefore (in the bosses eye) you are to blame for mess the project became.
        When they come with pitchforks, I’d stick to the facts, just the facts, and leave problem solving and solutions up to management since it doesn’t sound like they will listen to you anyway. Ex. “I pointed out X at this stage. I pointed out Y at this point. I pointed out Z here. I spoke with you about the issues I was seeing with outside contractor on this date. And I spoke with you on this date about the number of red flags on this job and I didn’t think we should proceed. I’m really at a loss as to what else I could have possibly done.”

        1. DJ Hymnotic*

          Yep, came here to say exactly this, and that saying something like, “What could I do differently in the future to point out X, Y, and Z?” not-so-subtly suggests that you are accepting fault for X/Y/Z going sideways by way of being a poor communicator. And maybe OP didn’t communicate their concerns well, but I can also easily see this type of manager who belatedly realizes they seriously borked up look for a fall guy and telli themselves that OP is (at least partly) to blame for all this by not convincing them earlier. If this manager believes they are good at their job, concluding that “OP should’ve more clearly communicated these concerns so that I could’ve reacted accordingly” does way less to challenge their self-image than “OP communicated these concerns and I repeatedly overruled them.”

          So yeah, I’d (respectfully but firmly) stick to facts and not open the door to taking any undue blame for poor communication. And I agree about not inserting yourself into the problem solving process unless you are clearly invited in.

        2. House On The Rock*

          I also don’t like the advice to soften or give them an out to shift blame. I get the point that maybe there’s another angle, but it seems pretty clear this is a toxic, blame heavy environment. I don’t think the bosses will respond in good faith to “how can this go better next time?”. The OP would likely be better served by documenting and referring back to the documentation.

      6. RebPar*

        I was coming in to say this, but you already said it so well. Usually I agree with Ask A Manager’s responses but this one wasn’t quite there. The real issue is not that there is a better way to raise concerns – the LW did, indeed, raise concerns repeatedly. The issue is a terrible manager and a dysfunctional setting. A new job is the only solution.

    2. Baby Yoda*

      Was just what I was thinking — document each and every flag you report in writing.

    3. OrdinaryJoe*

      re: “I told you several times that this project was going to end up like this and you didn’t listen to me” actually sounds about right to me.”

      Fully agree! BUT, I also know my boss would simply feel that *I* went into the project without being fully committed to its success, with a bad attitude, wanting it to fail, etc. Not saying that’s true at all, but that would be the feedback and impression I’d get.

      I’ve certainly had managers who felt we should all be jumping cheerfully off the cliff with the other lemmings on their orders, not hesitating and saying Hey … not so sure about this …

      1. anon for this*

        “I also know my boss would simply feel that *I* went into the project without being fully committed to its success, with a bad attitude, wanting it to fail, etc.”

        My father realized that buying another small, local manufacturer was a red flag festival. And he repeatedly brought his concerns to the attention of the president-CEO — his boss.

        His reward? Being told to make the acquisition work. And almost losing his own job when it didn’t.

        After years of six-day weeks for the company, Dad was thrown under the bus by people who been cheerleaders for the acquisition.

        He was accused of exactly the scenario that you present: Not being a team player. Not being all-in. Bad attitude, as you say. Etc., etc., etc.

        1. Fish*

          I don’t know if any heads rolled, but this reminds me of a past employer who acquired a firm that became their newest office location. I had left just before, so I didn’t see what happened afterward.

          Later they closed that office, and I heard that several senior professionals had urged against the acquisition in the first place. That was an early sign of big problems at the top, and the employer ended up merging with a bigger industry outfit to survive.

        2. Despachito*

          Damned if you do, damned if you don’t.

          It seems there is not a good solution to that. If the boss is unreasonable, she will blame the employee either way. I understand damage control at the moment but it is just a bandaid over a deep gaping wound. The real solution is to get out of there.

        3. münchner kindl*

          He didn’t believe in Brexit / new project enough, that’s why it failed! If he had just believed from the start, the unicorns would have arrived to bring the sunlit uplands to everybody!

          /s, of course, but if a major political party of a major modern country can after 7 years still not accept any blame or even reality, then it’s more widespread.
          At least people can look for new jobs with different bosses, but switching the whole government is difficult.

    4. Sparkles McFadden*

      They’re actually more likely to shoot the messenger.

      People really, really do not like being proven wrong. They will insist they weren’t wrong but “something unexpected” happened, or the LW didn’t explain the issues correctly and so on. People can ignore facts and even written proof when they’re determined to see things a certain way.

      If the idea is to avoid the situation in the future, you need to present this in a benign, post-mortem sort of a way so people will be open to your ideas. If you’re more interested in winning the conversation, “I told you so” is the way to go, but you won’t really accomplish anything positive. It’s frustrating for sure, (and it might not even work with certain bosses), but professional detachment makes it a little easier…or you go find a new job with sane people.

    5. lost academic*

      I don’t value anyone with this attitude and I value them less when they think they need to air it in that fashion. Your boss won’t either. If your goal is to just show that you were right about a situation and nothing else, cool. But don’t expect to be listened to MORE in the future if you approach it that way.

      I want to see people addressing root causes and proposing team and system oriented changes that improve the likelihood of success in the future. I want to see people interested and committed in overall success. I want to see people engaging others in solving problems that came up in the past or are/were identified as potential issues in the future – not just laundry lists of risks. If the concerns are real and they often are, they are not as likely to be ignored if they’re being handled correctly on all sides.

      1. Nia*

        The root cause of her problem is that her boss is incompetent. The solution to her problem is her boss suddenly decides to stop being incompetent or quits and is replaced with someone better.

        Do you honestly think that’s the kind of feedback her boss will “value”?

      2. Critical Rolls*

        You don’t value anyone who is frustrated after their warnings about the inadvisability of a project were ignored? You don’t value anyone who gets stuck with an impossible job after being blown off? You don’t value anyone who can’t fix the problem because their boss, the problem, is unwilling to be fixed?

        I get that “I told you so” isn’t a productive approach, but writing off someone in the LW’s position as not to be valued because of “attitude” is both unkind and bad management.

        1. Unkempt Flatware*

          It was such an adversarial choice of phrasing. You don’t value another human? Whoa.

      3. Chairman of the Bored*

        When the root cause is managers not listening to their technical experts the correct change is “listen to the experts you hired to advise you on these topics”.

        If you are one of these experts, it is not unreasonable to remind those managers that the last several times they didn’t listen to you things wound up going sideways.

      4. CakeOrDeath*

        Literally everything that you write in your last paragraph is something that was covered in the letter. Processes were put in place….did you miss the first paragraph of the letter? The problem is that the MANAGER did not follow the process they literally put the employees through training on.
        And you think the employees attitude is the problem? The whole point of their training was to not waste time on projects that are likely to fail/be trouble. And you think they should…waste time coming up with “solutions” to fixing failing projects…when they LITERALLY have a solution to that that was ignored by the manager???

        1. Venus*

          I have to admit, I almost wondered if lost_academic was OP’s boss!

          Not seriously of course, but the cluelessness was good for a laugh.

          1. rebelwithmouseyhair*

            I was just about to write “looks like we’ve found the manager”
            Except that the manager is not all that likely to be here, because they’d feel at odds with the whole vibe.

      5. Just No*

        It seems that your own list of what “people” should do is exactly the problem the OP is describing — throwing back responsibility on employees who aren’t managers who are then told to “go solve it, and do it with a smile!” instead of having competent management who stop bad decisions from becoming reality when they should.

        This is some real blame-shifting.

        1. CakeOrDeath*

          Yes exactly!!
          Especially the “don’t come at me with just a laundry lists of risks” when literally the first paragraph of the letter is LW describing how the company trained their employees on risks that they were supposed to identity and bring to management!

      6. Jenny Craig*

        This comment here is very blamey and it isn’t constructive to the OP. What actionable item are you suggesting? Be more interested and committed to success? Don’t supply a list of risks they identified (when boss specifically told them to identify and raise risks)?

        This isn’t a problem that is best addressed through a team or system-oriented change. This is the boss not listening. That’s the root cause that the OP, Alison, and most of the commenters have identified.

      7. I Have RBF*

        If I bring up red flags about something and the boss ignores me, there is no way I can solve those problems. Because the problem is not just the project, but the boss with blinders on!

        Yes, when things fail as predicted, those same blindereed bosses will blame the person who pointed out the problems, whining that they “weren’t invested”, “not a team player”, “sabotaged the project”, “change averse”, blah, blah, blah. Anything but admit that they were wrong and the project was a dud.

        I have no reason to put up with that crap. If I point out problems with a project, I’m not just doing it to hear myself talk. I’d rather just be able to do the job without badly screwed up projects hanging like an albatross around my neck.

        Some folks seem to think that people point out problems for no reason, like they don’t know what they’re talking about. Then they blame those same people when the projects that they pointed out problems with fail. This is incredibly stupid and frustrating, to the point that I will now start looking for a new job when management ignores my misgivings and insists that I do the ill-fated project anyway, because it is a no-win scenario, and I don’t like what bus treads do to my wardrobe.

        I’m a professional. I don’t owe people a polyanna outlook on craptastic projects that are doomed to fail. I owe them a realistic and carefully considered evaluation of the potential risks and rewards. If management doesn’t want to listen, I refuse to take the fall for their incompetence.

        1. Chairman of the Bored*

          Your last paragraph is especially spot-on. I’m a technical professional, a large part of my job is to provide a reality-based expert assessment of risks and likely problems.

          I don’t want my doctor to be a “team player” if that means she’s going to tell me my health is fine when it is not fine; I’m paying her to find problems and make a practical plan to deal with them.

      8. doctora colora*

        While I don’t love the adversarial tone of lost academic’s response, I do think that there’s an important part of useful perspective that highlights part of Allison’s advice.

        I’ve been in a situation where my boss hasn’t listened to my feedback on something for so long that I gave speaking up on or wasn’t as clear as I’d thought, at points I should have been. I later realized that I may have been right and had spoken up repeatedly, but wasn’t effectively strategic in documenting/communicating respectfully but directly up the food chain.

        I wasn’t THE problem, my boss was, but I had lots to learn about becoming a more effective part of the solution (and better CYA too).

    6. Mill Miker*

      In my experience, if it gets to the point you’re having to say that, it’s not going to work.

      Boss: You said it “might” end up like this, or would “probably” end up like this. If you can’t even be confident in your comments, why should I be?”
      Me: Okay, I crunched the numbers this time, and I’m positive this project is going to fail the same way as the last one.
      Boss: You’re using a lot of absolutes there, which means you’re falling into the trap of black-and-white thinking, and trying to use rhetoric to manipulate me. You don’t have a crystal ball, and can’t know the future, so I’m not entertaining these ramblings.

      And then that’s how you end up with “Cries wolf, and doesn’t raise issues soon enough” as a single point on your annual review.

      If a consistent track record isn’t convincing, then all that talk of noticing red flags is to get you to take accountability, not action.

    7. kanzeon*

      I understand the urge to say that, but I really doubt it would go well.

      After introspection, if the LW believes in their gut they did everything they could (and STRONGLY agree about getting it in writing & phrasing super-clearly), I’d say:

      “I agree that we identified early red flags in this process that we didn’t act on. We discussed it a few times, and it seems like you felt blocked/weren’t able to take action on those flags. What should we do in the future to make sure you can? Should I provide different documentation or more concrete numbers about what I’d seeing? I know we’re both so frustrated that those flags got blocked.”

      Lots of “we”, I’m on your side boss, you tried to fight it but you got blocked (even if that’s not true, it gives them a slight out so they feel less attacked and are less resistant). But also ensures LW is refusing to take responsibility.

      1. kanzeon*

        I understand the urge to say that, but I really doubt it would go well.

        After introspection, if the LW believes in their gut they did everything they could (and STRONGLY agree about getting it in writing & phrasing super-clearly), I’d say:

        “I agree that we identified early red flags in this process that we didn’t act on. We discussed it a few times, and it seems like you felt blocked/weren’t able to take action on those flags. What should we do in the future to make sure you can? Should I provide different documentation or more concrete numbers about what I’d seeing? I know we’re both so frustrated that those flags got blocked.”

        Lots of “we”, I’m on your side boss, you tried to fight it but you got blocked (even if that’s not true, it gives them a slight out so they feel less attacked and are less resistant). But also ensures LW is refusing to take responsibility.

        Could even add: “I can forward those emails to you and we could take a look at them together, and see what we can add for you to send to the grandboss next time”.

      2. But what to call me?*

        I like this one. It does well with straddling the line of ‘no, of course I’m not accusing you of doing anything wrong, boss [because that would immediately put you on the defensive and get me labeled as not a team player and I’m not in a position to not care about that]’ without implicitly or explicitly offering to take the blame.

    8. Beth*

      “I told you several times that this project was going to end up like this and you didn’t listen to me” would be satisfying to say, but not useful. It’s going to put OP’s boss on the defensive, which makes people shut down and get less likely to listen and adjust their behavior.

      That’s why a good post-mortem focuses on identifying problem processes rather than problem people. Even if a specific person is at the core of the problem, unless you can viably fire that person, calling them out personally will generally make the problem worse instead of better. “Our current process, when we are concerned that a project is likely to fail, is to document the red flags and recommend that we not continue with the project. I documented and escalated my concerns about this project and recommended that we cancel it, per that process; unfortunately the process didn’t end with correct outcome, since the project continued and has now become very expensive with no guarantee of success. Can we reevaluate the process by which we choose which projects to continue with?” is less personal and more likely to get traction.

  2. Aggretsuko*

    This reminds me of pointing out multiple times last fall that when we had people on strike, UPS was going to refuse to deliver to us. I brought it up over and over again with management and they refused to do anything, over and over again. Five packages had to get lost/stolen over the course of 2 months before they finally conceded to do anything like oh, have the packages mailed to non-strike territory.

    Oh yeah, and UPS is going to go on strike again, I brought it up again, and they still refuse to do anything. They. Just. Don’t. Learn.

    1. Moo*

      I feel you… and the OP

      At one place I was like an internal consultant I advised that the job should be X grade. The hiring manager had other advice that it should be X-1. I had been involved in a lot of hiring of this kind and knew it would be difficult to find a candidate for that rate. Others were included in the loop and it went back and forth so much.

      They went forward with recruitment at X-1 grade. After a very long and bureaucratic recruitment process they found someone they really liked but the salary was too low for them to take the job. The hiring manager complained to me that this was too low a salary and that the whole situation was terrible.

      I knew I couldn’t say I TOLD YOU SO because I might also actually just explode! And honestly I suspect they would not even remember the earlier discussions. I think I managed to say something like “yes, these roles are hard to hire to which is why I originally suggested X grade as a minimum.

      Apparently it’s not professional to just start yelling “THIS IS WHY YOU SHOULD LISTEN TO ME!” but maybe it should be…

  3. Roland*

    Oh my goodness. I’ve been there, OP. Called out that a project was unfeasible literally before anyone even started working on it, then it was brought up by my manager at the end of the quarter that it didn’t work and why I couldn’t have identified the issues sooner. Like I did bring the issues up, repeatedly and to the point my manager seemed to be getting annoyed, but I was new so no one wanted to listen. But still wanted to blame me for not being listened to.

    Hopefully this doesn’t happen again. But saving this answer anyway just in case…

    1. Nobby Nobbs*

      “If you don’t get me some support, in six months we’ll be on the verge of losing X project, Y site will be a disaster area, and Project Manager will be out in the field doing my job instead of his.” Six months later…

    2. Fish*

      Just to share a story, Samuel Goldwyn hired a young Garson Kanin as a production assistant at MGM Studios. Kanin immediately said a new script was terrible, and urged against making the film.

      Goldwyn fired Kanin and made the film, which lost millions. Several years later Kanin was a Broadway success with his play Born Yesterday, and someone suggested to Goldwyn that he hire Kanin to direct a film.

      Goldwyn’s response: “Kanin? He was connected with one of my worst failures!“

      1. Armchair Analyst*

        there is a new documentary out about the “American Gladiators” show which I guess was greenlit by Samuel Goldwyn Jr., who also was known for holding grudges and not changing his mind! hmm wonder where he learned that leadership from…

  4. Ellis Bell*

    Is it possible that the higher ups are losing track of things you’ve said before and treating every concern like the first one? Perhaps logging things as a timeline, or forwarding the last email with the more recent update would be a better way to keep them on track? If you get a response saying “give them one more chance”, I would reply “I just want to clarify that this would be their tenth chance! There’s also a possibility that it will affect x, and y and it’s extremely likely we will get a few more weeks in and still end up with nothing. If you really want to go ahead with it, at what point should we pull the plug if things stay this bad? I’ll continue keeping you informed of course”.

    1. Anon in Aotearoa*

      Yes, this. Do regular status reports (which are actually “will this project succeed?” reports), structured the same way every time including risks, issues, forecast timeline and total cost. Save them. Refer to previous reports in current reports.

      It could be that hearing individual concerns presented separately isn’t generating a pattern in their heads, so make that pattern much more visual and explicit.

      I mean, they’re still bad at this for not seeing the pattern.

    2. Ann O'Nemity*

      Yeah, I think we expect managers to remember details and conversations as well as we do. But often times managers are more removed from the day-to-day execution and/or have a lot more going on, and they just don’t remember! Sometimes it’s not malice, just forgetfulness.

      1. My Useless 2 Cents*

        But isn’t that why they get the bigger check? If they are responsible for making the bigger decision because they have the overall view of the project, they need to remember the details.

    3. Smithy*

      Only suggestion to this that I’d make is that instead of replying to email chains – I’d keep this log in a separate Google or Word doc that you update with each new issue or concern, and the date reporting this. The document is then attached to each new email that documents each time the concern was raised. So you both have the email chain of documentation, as well as the document with the bullet points of each concern, when it was raised, and the decision made by your boss after each meeting.

      With a growing tide of concerns, I’ve seen a few ways that supervisors/management can disregard how those concerns are reported. As mentioned, the first is that when something is first mentioned the response might be a version of “let’s wait and see.” Then over time, managers forget/misremember how long ago an issue started and only want to hear what happened recently. So they don’t treat the issue as long standing, but just the immediate issue at hand and relatively minor.

      Expecting a supervisor to read a longer email thread – particularly for a complicated project with a number of challenges becomes increasingly less likely over time. And misremembering how long ago an issue was first raised or how often an issue gets raised can be really easy. Thinking this is something you’ve been discussing once a week for 3 months vs twice a week for 4.5 months is an easy memory mistake, but on one document is a significant way of correcting how much extra work has been put in.

      1. Whodat*

        I was thinking about a Project OneNote with a tab specifically for this issue. Easy to attach the emails, and you can still have this timeline for them.

        1. Nameo*

          Yes, I was thinking OneNote, too! I think using a risk matrix would also help LW, if she doesn’t already. Numbers going up (especially color-coded numbers…) are easy to digest at a glance and give a more objective air. It also shows that LW takes the policies around risk identification seriously, but in a format that isn’t “just another email/meeting”, which is easy for this type of boss to dismiss

          1. Armchair Analyst*

            yes, this sort of tool or a Review Committee that asks about and evaluates risks is what the company needs, not what the LW should create or propose, though.

            something like “does this project require outside contractors? if yes, how many? of those, how many have we worked with before and [according to internal review of contractor system] received a rating of “yes, would work with again”?”

            I totally understand where the LW is coming from. but what else is going on in the company to understand project risk?

        2. Smithy*

          Excellent to learn about even better project management tools for this!

          But yeah – I think that while there are intentionally “bad bosses” that deliberately don’t see these things, there are also the “very busy bosses” who are just incentivized to not see these things. They’re not going out of their way to be malicious or sabotage, but to halt a project and fix problems does make their life harder. So they’d rather not if they don’t have to.

          For those bosses, having that information laid out as easily and clearly as possible, make it easier for them to copy-paste it for their bosses – etc. And then if even that doesn’t work, it doesn’t work. But clarity stops being the culprit.

  5. Sales Geek*

    My experience is that there is no benefit in an “I told you so” conversation with management. I’ve been there, done that. Our leadership would chat up how much they value the “wild ducks” in the organization. But it turns out that wild ducks are just easier to shoot.

    My job was in sales. For the first part of my career our sales team would treat a loss as a lesson. It was a formal part of the sales process to conduct a “loss review.” These meetings would include the front-line sales team, at least two (and often three) levels of management and sometimes a representative from the product development team. The point was to do an autopsy where we (the company) could learn to better compete. These meetings were documented and we had a library (online) where you could see where other teams failed so as to avoid their fate.

    Over time these meetings got smaller and smaller (less senior management) and slowly became a process where blame could be assigned and the target punished in some manner. Eventually the company just stopped the practice entirely because morale was so bad. The loss review process was by no means the only contributor to this change but it was not insignificant.

    If you can find a way to have this type of conversation, I wish you good fortune and I’d love to be wrong.

    1. Aggretsuko*

      Wait, they describe humans as “wild ducks?!?!”

      Welp, now we know what I am now. Maybe I should change usernames :P

    2. rebelwithmouseyhair*

      yeah this smacks of a blame culture. The point is not to learn from mistakes but to find someone to pin the blame on. That person is then fired. I have seen this happen all too many times.

    3. OtterB*

      There is an old list, sort of a joke and sort not, of the stages of a project that begins with Uncritical Acceptance, Wild Enthusiasm, … and ends with Search for the Guilty, Punishment of the Innocent, and Promotion of the Nonparticipants.

  6. BatManDan*

    “you’re the only one that didn’t think it would turn out this way; why do you suppose that is?” and “in the future, when I point out things that you asked me to point out, and then you ignore them, what do you want me to do next? Can you see why I’m frustrated? Can you see why I will not be listening to any whining, complaints, or blame about this project?” and “do you want to change the way you approach these things, or do you want me to change jobs?”
    Of course, this is all advice from someone who has never been anything other than self-employed, so your mileage may vary. LOL

    1. Not Tom, Just Petty*

      I remembered the tweet I saw in a list on Botaed Panda.
      The poster said she heard a woman on the phone at an airport bar say, “or you could just do what I told you in the first place.”

      That person said she would swear allegiance to that woman as soon as the call ended. I think OP needs to be that person.

      1. ShysterB*

        I saw that on Instagram. Screenshotted it immediately and sent it to all the women in my department in my office.

    2. Eukomos*

      Those would be great if you were talking to a student in your class, but a boss would take exception to them. OP would just end up on their shitlist, and sounds like the job change is inevitable at this point anyway.

  7. Bored Lawyer*

    Ahh, I agree with Alison that this is a tremendous opportunity for my favorite document in practicing law- the “CYA” or “Cover Your Ass” letter.

    After you have a conversation wherein your boss (or in my case, usually a client) essentially says “I hear your concerns but I am going to ignore your advice” take 10 minutes to write an email to him/her, or a memo to the file, or anything that has an obvious date on it stating what issues you pointed out, what advice you gave, and what the other party chose to do instead.

    “Dear [Boss], I am just writing to confirm the outcome of the conversation we had today wherein I raised issues A, B, and C. Having discussed it with you, I understand that I am to move forward with D, E, and F. I will begin per your instructions.”

    1. NobodyHasTimeForThis*

      AND when it comes up again, do not start with a fresh email. Start with revisiting the previous one. As in “Dear [Boss], In November we had decided to give Catastrophic Designers an extension. At this point A, B and C have escalated …etc.”

      I find if you phrase it not like “per my last email” but more on the lines of “refreshing your memory on the details of this project” it goes ok.

    2. ShysterB*

      This is pretty much what lawyers do when they advise “X” and clients decide “not X.” (Or when we advise, “Definitely not X” and the client decides, “Yup, gonna do X.”)

      1. Laser99*

        Does that occur frequently? I don’t have a lot o direct experience with lawyers, but when I have, I pretty much did whatever they advised.

        1. Avery*

          Unfortunately, it happens more often than you might think or hope.
          Though in my experience it’s things like “we told him to send us documents X, Y, and Z and instead he sent us X, part of Y, and also A and B for some reason” or “we told her she didn’t have to come to the Zoom court hearing for this, but she did anyway and it doesn’t really hurt anything but it’s just kind of awkward” more than the sort of flashy dramatic stuff you might be thinking of like “we told him to take a plea deal and he didn’t”.
          Though I work in family law, so maybe I’m just in the wrong field for the flashy dramatic stuff…

        2. rebelwithmouseyhair*

          yeah I think people ask for legal advice but don’t ask the real question. So they say “What should we do next?” even though they’ve decided what to do. The lawyer says, “well I recommend doing X, because Y would actually be against the law”. “Oh, what are the risks?” “If the other company finds out, they might sue you”. The client decides that the other company will simply not find out so they won’t get sued. And even if they did, well, they already have a lawyer to help them out of that pickle. They had actually been wondering whether they might get thrown in jail, so a possible lawsuit doesn’t sound nearly as threatening, especially since, as they already pointed out, the other company will simply magically never find out, because magical thinking.

    3. 10 Days of Unlimited PTO*

      This works exceptionally well for anything that has a significant outcome. It went well? Pull it up and cheer on the team. It went poorly? No individual takes unfair blame (it doesn’t just have to be to your own A that you save).

    4. Some Dude*

      And you can always just give the email a subject of “Meeting minutes” if you want to to look more benign.

      I also made a flag in Outlook “CYA” that I toggle on for emails I send or receive that I know are going to need to be found later on when something like this happens.

  8. ScruffyInternHerder*

    Isn’t that the definition of “Per my below email” attached to an email describing the issue from weeks ago that you’ve just forwarded, again?

    Oh, wait. Professionally.

  9. Hiring Mgr*

    Were you the only one flagging these concerns? Perhaps if there’s a next time you can get others on board in bringing it to the boss, and it won’t be as easy to ignore.

  10. Nervousmelon*

    I actually had this exact situation at my last job. A project I had flagged early on as dysfunctional because of the unreliability of external providers continued to be a huge time drain with no results. Management would sympathize with my (regularly flagged) concerns, but ultimately insisted I push ahead and try “once more”. I got poor feedback on a performance review partly because I had delivered so little. I had also completely lost my confidence as nothing I said seemed to matter, so ended up being criticised as “not contributing enough” in meetings. In the end, I had a breakdown, took some sick time and eventually quit with nothing lined up, but thankfully found a job at a much more sane company a month later. My advice is to get out of this situation as soon as possible!

    1. Coverage Associate*

      Yes, people remember how you make them feel with results that aren’t always fair.

      Recently, I had a project where I needed my boss’s approval before the work went out. I reminded him repeatedly leading up to the deadline. The deadline passed, and he was caught on his back foot. He knew it was his fault. He admitted this to my peer, and I found out later when reviewing the file. But his impression of me was a kill joy, and he didn’t offer me better opportunities offered to my peers who could massage his feelings better.

  11. VP of Monitoring Everyone’s LinkedIn Profiles*

    In my experience, anticipating problems at the start of a project leads to being accused of causing them.

    1. Not Tom, Just Petty*

      This. “You knew this would be a problem. You could have avoided (my hiring someone in a different time zone who only works their mornings which are 11 pm our time) missing deadlines since you had the information!

  12. Rick Tq*

    I’ve learned that I need strong evidence and at least one ally before I raise the No Bid flag at work. Being able to show how the last N projects with this subcontractor (or client) went over budget/missed schedules, etc. makes your objections more concrete and harder to ignore.

    If the outside creatives have a history of being that bad, why not start researching possible replacements for them?

  13. Sloanicota*

    Honestly, I deal with this at my job, and my current opinion is that it’s not my role to argue with the decisions the higher-ups have made (I may raise an issue once, but not “cancel the whole project” more like “we should document back-ups for these contractors, and have a clear section in the contract about how we can cut them loose”). There’s places where it is welcomed for more-junior people to push back, but not at my current org – they’ve made it clear they’re going to do what they’re going to do, and my job is to implement as best I can. Including sometimes when my best doesn’t work – it’s my job to try. I do not beat myself up, nor do accept being criticized or castigated when it doesn’t go well. Not my circus, not my monkeys.

    1. Workfromhome*

      This so much this.

      I once worked at a software company in support where the sales people flat out said to us:
      Our goal is to sell the product first and worry about YOU fixing it later.”

  14. Jane Bingley*

    It may also be helpful to reference past projects going forward, especially if you’re able to collect some very basic data. An example:

    “I’m really concerned that we’ve now been asked to do a fifth round of revisions when our contract only allows for three. In the past, I’ve seen five contracts where reaching the fifth round of revisions led to frustrations and a failed contract overall, and only one where it worked out. In the one that worked out, the client was apologetic and offered to compensate us for the extra work. The pattern I see is that if a client isn’t happy with us after four tries, they just don’t like our work, and the relationship is fundamentally broken. Do we have any signs that this client is different?”

    And strongly agreed about getting it in writing. Even when things are going well, it’s a good best practice to document meetings by sending a summary email afterwards with action items, commitments, and key decisions.

    1. Ashley*

      I also love when the same pattern seems to be happening in planning to reference disaster project X, and say I am seeing a lot of the same problems we had on X project and I think we all remember how poorly that went.

      1. Jam on Toast*

        First off, my sympathies, OP. I’ve been in your shoes and it’s the pits. It feels like you’re trapped in the passenger seat of a slow moving car and you can’t grab the wheel or get the driver to slow down, even though you *know* the car’s going to lose a tire, spin out of control, before bursting into flames.

        One thing I can suggest while you’re planning your exit, be strategic about your optimism and team player credentials. If you’re always the team’s Cassandra, it makes it easier for your boss to just lump your smaller, less urgent risk analysis and your legitimate APOCALYPTIC THE END IS NIGH! warnings and tell themselves a story about you…oh, that OP, they’re a worry wart/not a team player/exaggerates everything kinda person and just tune you out, because they’ve already made up their mind about the value of your messages . It’s a them problem, for sure, but it has a huge impact on whether or not they hear you objectively. But it’s much harder for your boss to ignore you if you’ve cultivated a consistent reputation as someone who is a positive problem solver. So I’d suggest you strap on your pompoms and find things to be visibly excited and positive about, and make a plan to only raise the alarm for big ticket issues above, say a level 3+, and not raise any level 1 and 2 annoyances with your boss, at least for temporarily (and yes, it probably will feel inauthentic and like you’re cutting corners, but do your best to make your praise as legitimate and consistent as possible, within the scope of your team’s reality and just remember that it’s a consequence of your boss’s poor listening skills and not your risk management abilities)
        Having that goodwill cushion will mean that when you do take up the warning drum it will be much more likely amplified by your co workers, who know you as a rational and generally can do peer who doesn’t sweat the small stuff and for your pie in the sky boss, the impact of bringing concerns about ONE big issue will be much harder for them to ignore/lump into general background noise AND hopefully dilute any impact that pointing out potential red flags has on your career trajectory and annual performance evaluations, because it’ll just be one aspect of your performance overall and not the one thing boss has to hang their (poorly managed, overly myopic) hat on.

  15. Lora*

    In my experience, here is what works:
    1) Attach a dollar value, even if only order of magnitude, to items identified as critical risk. Include both the dollar value of materials AND the dollar value of run time, ie “if Manufacturing is idled for 8 hours due to lack of Part # 349587, the productivity cost is $10,000” or whatever it is. It’s hard to find out overheads, but sometimes you can get Accounting to make a guess for you.
    2) Do a risk management and mitigation analysis. “If our contract genius E. Mask flakes out and doesn’t deliver on the new truck design, we plan to include a contract subclause that allows us to leverage existing designs from Fred Motor Company, this will cost $$ in contract negotiations and lawyer time.”

    When it’s very cut and dried and pre-agreed that “if the Bad Thing Happens, here’s the expensive thing we shall have to implement,” it’s more like you are following a plan than saying “I told you so.” If they complain about the risk mitigation expense – yes, well, this is the plan. It’s less about “I told you so” and more about forward planning and strategy.

    1. CM*

      I use a very similar approach — put in an email, “I raised a concern about delayed shipments and made the recommendation that we do __, but I understand we have made a business decision to proceed without addressing this. If the shipment is delayed, we should be aware that it will have ___ impact.”

      And then when the delayed shipment happens, you can say, “Yes, this is what we decided to do, and we decided to live with this impact. So now I think we should…”

  16. Not Tom, Just Petty*

    What if you take Alison’s advice before the project, a pre-mortem?
    Instead of raising problems, ask for solutions. Assume manager is going to do whatever s/he wants and work within that.
    Ask manager to brainstorm for solutions you damn well know are going to pop up.
    “Bob is in England. He works M-T-W morning, his time. How should we schedule his steps to include extra time for him?”
    He won’t need extra time. He will follow the schedule we give him.
    “I agree, he will do his best, but he’s also part time, so we need to put deadlines on his work days in his time zone.”

    1. Weaponized Pumpkin*

      I love pre-mortems and have successfully used them to get ahead of “what happens if…” questions. Surface ideas around how we’ll communicate problems, what happens if we go over scope, how we handle it if the other consultants don’t deliver. It can feel constructive and positive.

      I’ve also run into some people who just won’t do them! I’ve actually been asked: so what you’re saying is you think we’ll fail? Sigh. No. I’m saying that there are always problems and the more we’re prepared for them the less impact they’ll have.

      1. Not Tom, Just Petty*

        I’ve had that conversation. When it’s me trying to set expectations with my 8 year old nephew, it goes like, “Yes, we will never have time to get lunch and and see the movie and you will never see a movie again. Does that sound like what I’m saying?”
        And then we laugh and go on our way.
        I did once use this on a coworker who is the biggest Eeyore in the world…”yes, you are right. None of the fixes will work. The project will fail and we will all be laid off. Let’s go home.”
        She had the decency to laugh. But know your audience.

  17. G*

    Just concurring here that this type of pattern of behavior in picking and conceptualizing projects is also a thing in nonprofit sector too. It’s amazing how many people – especially higher-ups – love the feeling of saying yes to things above all feasibility and operational concerns.

  18. Anna Badger*

    one thing that I found personally useful in previous jobs (thankfully not needed in my current) was to be very consistent in my language when flagging the same concerns over time, which created a sort of echo effect that was harder to dismiss when I turned out to be right

    1. Annie Pi*

      This is such a great point. Sometimes, when I feel like I’m not being heard, I’ll try saying the same thing in multiple different ways – hoping to find something that will stick. But that probably inadvertently prevents that echo effect and dilutes the message.

      1. Anna Badger*

        it’s tricky because it really matters whether someone isn’t listening because they haven’t understood what you’re communicating ( in which case rephrasing is the right thing to do) vs because they don’t want to hear it ( in which case the echo might eventually get through but rephrasing won’t help)

  19. Hazel Atlas*

    Something my boss would respond well to (YMMV) would be a method of tracking project productivity as well as a scoring system for red flags before accepting a project, and an ongoing feedback loop on poorly performing projects. Making the conversations about data driven performance helps take the personal element out of it.

    1. Hazel Atlas*

      Coming back to flesh out my thoughts. Then it’s not “I told you so”, and it’s not “you didn’t raise concerns”, it’s “our data shows that projects with a red flag score of 6 or higher tend to perform poorly, so let’s make that the bar for rejecting them” or “we’re scoring ‘history of poor quality work’ equally with ‘doesn’t return calls within a day’, but based on this data from May to June, I think we should start giving it 2 points instead of 1 because it needs to count more” or “Freelance Annie has turned eight projects into duds this year with problems ranging from missed deadlines to client rejections to not returning our calls for days at a time, we should lose her number”

      You guys are reviewing this stuff very subjectively and reaching different conclusions, and also having trouble connecting the dots between the assessment you do in the beginning and results months later. Data and tracking can help solve those problems, and you’ll look proactive and forward-thinking, which is a better look than “I told you so”! Let the data tell them.

  20. TG*

    I hate this situation to be honest because I’ve had this happen and no matter how it is framed, management doesn’t want to hear it.
    In my case it’s a department I’m doendent on for work who operates in total chaos.
    I’ve had to learn to not invest in this department and projects with them. I continue to escalate red flags and hope the problems don’t come back on me.
    Sounds cold but I have e tried everything to help them or influence the work positively and nothing works:

    1. Grumpy Elder Millennial*

      As a former project manager with a giant project that kept morphing, sometimes you have to make the problems management’s issue. If a deliverable is late, that means an e-mail saying: “hey manager, I tried X, Y, and Z, but Deliverable is now late. How do you want to proceed?” or “hey manager, I’ve been trying to get an answer from Wakeen on Topic, but so far no response. If I don’t hear back by Date, that’s going to delay X and Y. How do you want to proceed?”

      Basically, a) I’ve tried All These Things to solve the problem, b) but haven’t been successful. c) What do you want to do?
      At some point, the issues with the contractors can get too big for staff to handle. Like the deliverables are consistently poor quality / missing stuff, or deadlines keep getting missed. At that point, someone in your leadership team needs to have a serious talk with someone in the leadership of the company that got the contract.

  21. Sunflower*

    Agree that you need to put every red flag in writing. You can forward it back to those who throw you under the bus. CYA is my motto.

  22. I Wrote This in the Bathroom*

    OMG I had this project! Very hot and high-visibility, poorly designed, that the leadership had brought in a new offshore team of contractors to implement, with us in-house folx serving mainly as subject matter experts (of sorts). We realized really early on that the project wouldn’t work. Had enough relationship with business and the clients to find out that it hadn’t really been requested, or needed, by anyone. I admit I panicked. Based on what I’d already seen of the project, I saw massive failures and loss of client satisfaction in our future. First I talked to my direct boss. Asked in advance for a few minutes on the next standup, and brought it up. Was shouted down and told to stop being negative and to be more positive. Next I went to talk to my grand-grandboss, who I’d worked with in a previous job and had a great working and personal relationship with. Seemed to get good traction there and he promised to bring it up to his friend, our CIO. Met with him again a few days later and he said CIO’s answer had been “yes this project is a hot mess, but it is also a web presence, which our company sorely needs”. At that point, I figured I’d exhausted all of my options, and continued to work on Project Doom until I was pulled into something new. Project Doom was completed, over time and probably over budget, went live, where it proceeded to not be used by anyone. My dire prophecies of Project Doom slowing down the database performance, and as such affecting all existing software (including the company’s flagship app that it uses to make money), did not come true, because when Project Doom became Website Of Doom, it went on to have zero daily users, every day, for eternity. So thankfully, the only consequences we suffered is that we’d wasted a lot of time and money. I never said I told you so, one reason being that after a few reorgs, layoffs, and retirements, I no longer worked for any of the people involved. My teammates and I did have good success with saying things, in design meetings for new projects, like “if we do thing X the Y way, it’ll become the next Project Doom and do we really want that?” to a resounding NO!!! from the management. So based on my own experience, only advice I have is to have your failed project be an example for the future. (If we do this again, we’ll have such and such problems again like we did with Failed Project.) Though, if y’all already had training to pinpoint the failure points, and Failed Project checked all the boxes, and the leadership still didn’t care, I don’t know what good using it as an example will be. It’s a good thing that you are job searching!

    1. Critical Rolls*

      “If you can’t be a good example, then you’ll just have to be a horrible warning.”
      ― Catherine Aird

        1. I Wrote This in the Bathroom*

          I have a fridge magnet that says it! (From a vintage-toy store that has since closed)

  23. Alton Brown's Evil Twin*

    I was going to suggest using a risk management approach — early warning signs of issues, what to do to forestall disaster, what to do after disaster strikes — but it looks like your company already has some sort of policy about at least steps 1 and 2, but then your manager fails to follow it.

    I’m afraid that this is a “your manager sucks” situation. He isn’t being rational about this – the “give the outside creatives one more chance” thing sounds like classic sunk cost fallacy.

    1. Peanut Hamper*

      This. All of this.

      LW says they are job hunting. I would be less concerned at this point about how to professionally say I told you so (“as per my last email”) and figure out how to inquire about this in future job interviews so they don’t have a repeat of this situation.

    2. OP*

      OP here to say that 99% of my boss’s bad decisions like this are based on the sunk cost fallacy. And also his refusal to like … do things. It’s fun.

      1. I Have RBF*

        My advice? Run. This won’t improve, and you will get all the blame when your boss throws you under the bus.

  24. LinesInTheSand*

    Depending on your relationship with your own boss, you could frame this as “How can we make sure we don’t find ourselves in this situation again?” and when your boss says “You should have brought this up earlier”, you say “I did make this visible in these ways, and obviously that didn’t work. How do we do this better going forward?” ad infinitum.

    I have noticed that even in organizations that do take retrospectives seriously, there’s a gap between drawing conclusions about the current project and applying those lessons to the next one. I think you could propose that in the future, your team schedules an early “state of the project” meeting to discuss red flags. Bring this project up as a reminder of what happens when they’re ignored

    1. LinesInTheSand*

      Also, I think it’s generally unlikely that people who are excited about a new project are going to pull the plug early because of red flags. A more probable scenario would be that you identify a bunch of red flags early on and develop strategies to mitigate them early as well so that they don’t spiral out of control.

    2. Weaponized Pumpkin*

      Yeah, at my company we do the post-mortems but generally don’t bring the lessons learned into the next project. Drives me nuts. That step needs to be on the PM’s checklist.

  25. Rage*

    Yeah, once I was putting together our annual HR retreat, and my boss at the time (former employer) proposed holding one of the breakout sessions outside in the garden “because then we can use that original room for another breakout session!” I said that: (1) the outside area is in a public garden and we don’t have the authority to tell other people to go away/be quiet/etc. and (2) we need a contingency plan for inclement weather; if it rains, you want somewhere for the outside session people to go, so we can’t use the original room.

    He told me to “stop being so negative”.

    Anyway, in the end, he decided to not go forward with an outside session.

    Guess what happened on the day of the retreat? IT SNOWED. In April. 2 inches.

    I didn’t even say anything, but he stopped calling my “prudent planning” negative.

    1. Unkempt Flatware*

      I hate working or eating outside. I hate when people suggest it. I’m glad he didn’t do it.

  26. Bad Wolf*

    I actually have to disagree with Alison’s advice here. That’s a lot of coddling of manager’s feelings and apologizing to them for their mistakes. If this was in the context of a romantic relationship, it would be obvious that it’s toxic as hell.
    I would throw the problem into your manager’s court instead – “I told you in the beginning this project will be a problem. You told us to run with it anyway. Ultimately it’s your call, so we are running with it. Well, it’s a problem. What do you want to do now? Tell me how you want to handle it. It’s your call.”

    1. CommanderBanana*

      Yeah, this bothers me. The amount of energy we’re expected to expend tiptoeing around managers is truly bananas.

    2. Mild Accountant*

      The problem is that the power dynamics are different. In a romantic (or platonic) relationship, everyone is equal. (In theory, anyway.) In work relationships, there’s often a clear hierarchy.

      Granted, it is toxic as all get-out and – as a former supervisor – I firmly believe we as a society should make it easier for subordinates to hurt their managers’ feelings when necessary. But…like, not everyone can potentially risk their job for their own values.

      1. Bad Wolf*

        In my experience, once you start accepting the blame for other people’s mistakes, you become the scapegoat. Anything that goes wrong becomes your fault. It starts to define you as the office f**k up. And your job will be at jeopardy regardless.

    3. Cedrus Libani*

      I read Alison’s advice as a short-term harm reduction strategy. Yes, in a perfect workplace, we’d all speak to each other like adults, which includes taking responsibility for our own emotions. We don’t always get to live in that world. Sometimes we just have to do the best we can with a boss who sucks and isn’t going to change.

      When I was younger, I might have had some optimism about finding just the right communication strategy. I’m now much more inclined to accept the situation as it is, which probably means running away from it as fast as possible, because I have a real talent for making enemies when I’m obliged to deal with such people over the long term. (Also, it’s miserable, and life is too short for that nonsense.) That said, I’m not above suffering fools gladly if it can save me some headaches in the here and now.

  27. Jaina Solo*

    Personally, I’d go to the boss and say something like “I’ve noticed x, y, and z on this project which are concerns for timeline/scope/etc. Based on that, can I get your blessing to [insert whatever your proposed plan is be it cancellation or something else]?”

    I used to use that template with a good boss and it helped because she was maxed out at work and couldn’t attend all the meetings and convos. There’s nothing for the boss to do but choose a yes/no which will help with an indecisive or just bad boss. And definitely get it in writing–you want that whole trail of your bringing up issues (and solutions) and the boss saying no. Paints a great picture that you were ahead and they were not.

  28. Anonymous editor*

    OMG! This is so similar to my day-to-day. Personally and professionally the most relevant AAM post ever.

  29. The_artist_formerly_known_as_Anon-2*

    Over my long career – I noted the thing that gave me the greatest personal and professional satisfaction – was to put forth a proposal, carry it through, and have it succeed.

    The next best thing that delivered personal and professional satisfaction – was to have your plan rejected — and when management failed – you just know …. you don’t have to say it….

    “I told you so.”

  30. BellyButton*

    I have found it helpful to do a project debrief/post mortem/lessons learned with the entire project team and the leaders who make the decisions on if a project continues or not. I would at a category for red flags, the date it was identified, the decision made at the time, and what action to take in the future.

  31. Problem!*

    In my experience those kids of bosses have egos that are too large to allow them to admit they made a poor decision.

    I recently left a job because the new management wanted to throw their weight around and tried to implement a new system that wouldn’t work for a myriad of reasons. As the most senior person below management I called a meeting with them at the beginning of this to spell out exactly what was going to happen and asked what their plan was for when the inevitable did happen. I was talked down to and told to stay in my lane. So I did. It was a disaster and I quit.

    If I was less professional my exit interview would have only consisted of “f around and find out”.

  32. GreenDoor*

    “I don’t think we should greenlight this” makes it too easy for your boss to disregard your opinions/concerns. Shift the decision making back to them.
    “I’m experiencing X problem….how would you handle that?”
    “I’m having trouble navigating Y issue…what would you suggest.” It forces them to consider the problem, ask you more questions, and harder to make you the poor decision maker.

    Even for follow-ups or problems midway you can ask, “the last time we chatted about the Z project, you suggested X but I’m still finding problem Y. What’s your ideal alternative?”
    Keep shoving it back on them. (But overall, yeesh! To be working where your concerns and opinions are blown off so much? Yikes!).

  33. Trout 'Waver*

    I think you have to be really careful when being a naysayer. It’s really easy to be pessimistic because you’re either proven right or the project is successful.

    Think about it from the other side. When you lead projects, everyone has an opinion about what you’re doing wrong. And they’re not shy with sharing it. Picking out the legitimate concerns from the non-legitimate ones is tough. Your most annoying coworker? They are just as confident in their criticisms as you are.

  34. Donkey Hotey*

    No advice but plenty of empathy, OP.

    Prior employer, I left after the fourth round of “This will go poorly” vs. “But we’ve always done it that way” resulted in “How could we ever have seen this coming?”

    Job before that, I had raised the red flag early and often but Sales was Convinced. It took (policy) sending the cost sheet out to all VPs with the glaring -500% margin to finally get Sales’ attention.

  35. I'veBeenThere*

    A RAID (Risks, Assumptions, Issues, Dependencies/Decisions) Log might be helpful in terms of keeping a written record. There are some nice templates online, many of which include places for who raised the issue and the date the issue was raised.

    P.S. I’ve been in your shoes on digital creative projects and I understand the frustration.

    1. Grey Coder*

      Came here to say this. Risk and Issue logs have been standard procedure at many of my jobs. Think of a potential problem? Raise it as a risk. Get the right people to look at it, consider any mitigating actions to prevent the risk from occurring, and/or accept the risk. Have a regular meeting to review the risks. Minute the heck out of that meeting.

      “No one said this could be a problem!” — it was raised as a risk two months ago, you were at the meeting where we decided not to do anything, see the minutes of March 15th, etc.

      Of course it’s best if you can all act like grownups and take responsibility, make contingency plans, etc in the meetings, but worst case it’s good for CYA.

    2. Respectfully, Pumat Sol*

      I also came here to say this! This is practically the reason RAID logs exist!

    3. Tiger Snake*

      The added bonus; if OP brings these as documented risks, that means that someone needs to approve moving forward anyway. And that gets logged in the RAID as well.

  36. Critical Rolls*

    It’s interesting how many people have had their concerns dismissed as “negativity” or “naysaying.” There’s a book by Barbara Ehrenreich called “Bright-sided” about the way toxic positivity has impacted America, including as a contributor to the 2008 financial collapse, due to just that kind of thing.

    1. I Wrote This in the Bathroom*

      I have a copy and recommend it to everyone! (Pretty sure I first heard about it on AAM.)

    2. Trout ‘Waver*

      Eh. The problem with opinions is that everyone has one. For every thoughtful person pointing out a legitimate flaw there are dozens offering poorly thought out unsolicited advice.

      1. Mill Miker*

        Everyone has an opinion, sure. The problem is when a “professional opinion” from a relevant domain expert with a track record of almost always being right is dismissed offhand as “Just an opinion, and a pessimistic one at that”.

        1. Trout ‘Waver*

          The point is that everyone thinks they’re an expert with a track record of almost always right.

      2. I Wrote This in the Bathroom*

        Toxic positivity in a workplace is a real and known problem, though, if we are talking about the specific issue when complaints and warnings are met with “just be positive”.

      3. Critical Rolls*

        This is clearly not the case here. LW said, “Hey, we talked about these red flags, and I see them in these 14 places on this project,” and then the project was a nightmare.

        You seem very willing to throw out 100% of concerns as “probably someone with an overblown idea of their competency who’s overreaching.” That is a recipe for being Very Surprised by any problems you can’t personally spot, and also a recipe for losing competent employees who don’t appreciate being assumed to be idiots.

  37. Coffee Bean*

    When you are assigned to these projects, are you creating a project plan that clearly calls out the risks? If not, I definitely recommend doing this, and color code the risk items in red. Identify the potential consequences of the risks (E.g., launch delays; lack of functionality; impacts to other projects; loss of revenue) Send an updated project plan every week. This way, you have backup if you manager questions why these risks were not identified previously.

  38. Serin*

    This is focusing on a detail rather than addressing the main point of the letter, but in this specific case I think there are alternatives other than “persuade the higher-ups that this project is doomed to failure and get them to cancel it” and “just let it fail.”

    OP writes: “Somehow it’s our fault if freelancers or other contracted individuals ignore our emails or turn in work that’s not in line with what we contracted them for or have every excuse under the sun for why they can’t meet a deadline they already agreed to.”

    This ought to be addressed at contract level. There need to be standards and deadlines in the contracts, and specific financial penalties if they’re not met.

  39. Rick Tq*

    And if specific contractors have a history of poor performance, dump them. Yes, it takes time and effort to qualify a new team but if there are no consequences your contractors will never get better at responding on time and to specification.

  40. ragazza*

    I feel like this is a situation where the competent person is just screwed. I had a boss I liked and respected a lot. We decided together that each project I worked on would have to have a brief. She emphasized that if there was no brief, I couldn’t begin, and she would back me up.

    Then she gave me a project without a brief. I tactfully pointed out our new policy. Oh, no problem, this project is easy, it doesn’t need a brief! Well, you know what happened. The project went off the rails and guess who got blamed for it and was made to feel stupid because I couldn’t do the project the way they wanted? Because I’m not a mind reader. I completely lost respect for my manager after that.

  41. Janeric*

    Alison’s advice is good for the LW’s current toxic environment but it would be GREAT in a less toxic environment. Good management would really appreciate a lot of the reflection and lack of accusations

    1. Grumpy Elder Millennial*

      And in the LW’s current environment, it’s definitely worth trying this out and seeing what the response is.

    1. The answer is (probably) 42*

      Ooooh I just mentioned her IG account in a comment below too! She’s hilarious!

  42. Dclgirl*

    I don’t know how common this is in your industry but it is very common in the Health Environment and Safety area where I spent a lot of career. After ever accident or incident we would do a Root Cause Analysis. There are many techniques and some require training in the process. However one that I like best requires no training. It is called 5 Whys.

    You get a fairly small group together and ask the question of why this happened If you say that the llama groomers didn’t respond quickly enough then you ask the question why didn’t they respond in s timely fashion? And so on. (I’m sure there are examples in the net that explain it better than I just did. Sorry typing in my phone at the beach

    The advantage is there are no pointing fingers and you usually come up with at least one root cause

    1. Tiger Snake*

      “there are no pointing fingers”

      How did you pull that off? I found the ‘just ask why until you reach the end’ solution always results in circular finger pointing.

  43. KEWLM0M*

    This! This is exactly what I come here to read! Thank you, Alison, for yet another example of precise, professional language to address a business issue.

  44. linger*

    The worst possible outcome from this problem — and it’s the one this boss is heading for — is the “Cassandra in a Coalmine” scenario.
    1. Cassandra gives her warning, and Boss ignores her.
    2. Bad thing happens just as Cassandra warned.
    3. Boss blames Cassandra for not giving a warning and letting bad thing happen.
    4. Cassandra is discouraged from speaking up next time.
    Of course, just because the warnings stop, that does not mean the situation has improved.

  45. Tiger Snake*

    “Every time, my manager said to give the outside creatives “one more chance” (I’ve lost track of how many “one last chances” they’ve gotten at this point)”

    Is it maybe this is a missing piece of the puzzle?As in; is the OP bringing up the issues to their manager as though its the first time, every time, rather than bringing this as a clear pattern and providing updates on how the last last chance failed. The actual conversation of “The ‘last time we gave them a last chance to fix _. They did not do this: and THAT has now turned into THIS, and if we don’t do X right now it will result in [future event] within the next 5 months’.”

    The upper executives are baking too many pies and thinking of too many things at once to understand and remember the ongoing timeline like you do, so you need to not just identify the risk, but also be able to explain the systematic stuff in upper-echelon-language.

    It’s like putting a topographic map in front of someone who reads thematic maps and expect them to know the mountain is steep: it doesn’t work. You need to draw the map that they know how to read.

  46. learnedthehardway*

    I think it is time for a mid-project review – do a write-up, point out what is working, what is not, how you had said originally that this wouldn’t work. Email it to your manager and grandboss.

  47. The answer is (probably) 42*

    All I can think of is loewhaley on Instagram’s series “How do you professionally say” with her work bestie. She’s talked about various flavors of how to say “I told you so” in a work setting, in a few different contexts.

    In general I highly recommend her account, @loewhaley – not really so much for work advice, more for general office based humor and her small cast of characters (all played by her) that navigate work boundaries together.

  48. Caroline*

    Always keep receipts. Always.

    Then, when the inevitable lecturing and blaming starts, you can respond with ”I agree that A and B are huge issues – this is why, on 11th August I raised it with you, and then again on 9th September, and then again when we discussed an adjacent problem on 19 September. Your view then was that it was worth it and not to over-think (or whatever). ” Then do not say anything else. Just sit there, ideally on a group call and look expectantly at the manager concerned.

    But mostly, please find a different job.

  49. TG*

    LW#1 definitely want an update but I’d do as Alison said and quickly bring in someone to take this over and if the person who is abusive tried to stop it let them know their status. Also in case they try and destroy anything see what legal recourse you have now so you can let them know if they do anything what the resource could be. Lesson learned never to let anyone take over like this and to always demand that industry tools be used when developing apps that need support and access.

  50. Purely Allegorical*

    I actually disagree with Alison on this one. I worry that the language she suggests is overly subservient to the manager and creates too much risk that the manager will blame everything on OP anyways. Been there, seen it happen too many times.

    If you have management who are already this bad at overseeing projects and making cost/benefit calculations, they are not going to be the managers who hear “what could I have done to raise these flags differently” in a way that makes them realize they were wrong.

    Other folks on this thread have made really great suggestions about getting your warnings in writing, using a risk matrix, an errors log in a Google doc, etc. Follow that advice. When the boss calls you in for the post-mortem (or you call it yourself), show them the log and ask “at what point in the timeline of errors stacking up should I be more vocal about halting the project? What would you like me to do to effectively put that on your radar?” And then agree on an escalation plan. Put that in writing too. And then follow it the next time.

  51. Florp*

    It’s possible your boss keeps saying try again because of A) sunk cost fallacy, and B) she can’t think of any good solutions. You may need to prod her into being more proactive.

    I take a “hope for the best and prepare for the worst” attitude towards…well, life in general. You can use that attitude at the beginning of these projects–in addition to predicting failure points, you can ask what options are available to you to mitigate them. Hope for the best allows you to be cheerful and positive. Prepare for the worst positions you as looking out for your company’s (and your boss’s) best interests.

    So, instead of “this freelancer has been a problem before,” say something like “this freelancer has previously given us work that required several revisions before it was acceptable. I’m hoping he’s got more experience with us now and better understands what we need, but if we’re going to continue to use him, can we withhold final payment until we’ve approved his work? Is there a point at which we can cancel the contract with him and get someone else?” It’s a problem and some possible solutions with a little face-saving politeness. Face-saving for the boss and freelancer, that is.

    For a project that you can see is going to be general chaos: “Of course I always hope for the best! But based on what we learned from the last project like this, we need to prepare for the worst. Can we plan now what we’ll do when X is late, Y has gone missing or Department Z can’t shift their schedule to accommodate us? I’m worried this could affect our ability to deliver [different project to more important customer].” Note the unpleasant consequences tacked on at the end.

    Use “We” instead of “I.” It always amazes me how much this helps.

    Always, always, always in writing! If you boss answers you verbally, send a follow up email reiterating what she said. You can disguise it as you doing further critical thinking on the subject, as in “after our conversation the other day when you said we could require a first draft from freelancer B to make sure he’s on the right track, I realized that if it’s good enough, we could give that first draft to marketing so they can start planning their work.” Or whatever is appropriate for your particular company.

    If you can be explicit ahead of time with problem/bad consequence/possible solution, and position yourself as protecting the company, your warnings may register better. Look up Failure Mode and Effects Analysis. It’s a way of thinking that might help you here.

  52. An Australian In London*

    I love the many hopeful optimistic comments about appealing to good faith and reasonableness.

    If only.

    OP discloses routine hypocrisy from the leadership and routine gaslighting from their immediate manager. While any of those people remain in this organisation I don’t believe there is *any* chance of things changing. (Them being gone is necessary but not sufficient; other org changes are needed too.)

    You cannot reason someone out of a position they did not reason themselves into. These projects will always fail at this org, and these managers will always blame everyone but themselves. Leave, quickly, before one of the blamethrowers becomes litigious or reputation-trashing. Sorry.

  53. Grumpy Elder Millennial*

    For future projects, could you explicitly point out that you’re seeing the same red flags that made Previous Project be X months late and $Y over budget? I think it’s one thing to have a checklist tell you there will be problems and another to remind people about an experience they had. (To be fair, I’d listen to the checklist, but it sounds like your leadership doesn’t).

    Or could you note that you’ve had X, Y, and Z problems with that contractor in the past, so if the decision is to proceed, you’d suggest having a plan to monitor those things and deal with the issues proactively.

  54. FlufferNutter*

    OP- are you my husband? I did send this to him so he has the support of knowing how many other people are, sadly, dealing with this. CYA, by all means. Humans are so exhausting sometimes. Good luck!

  55. Book miner*

    I might just be projecting, but this sounds like book publishing to me. I never was able to convince anyone to listen to my concerns at the start of a project, but by putting things in writing and phrasing them in as clear and neutral a way as I could, I at least managed to avoid getting blamed for them later.

  56. CR*

    The immediate issue is that the leadership is allowing flawed projects to continue despite multiple warnings from multiple employees.

    The underlying issue is that the company is clearly dysfunctional, uses a blame based approach to deal with known issues, and gaslights the employees when the issues show up as predicted.

    Those are all red flags, and a sign to start looking for another job.

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