transcript of “I Can’t Quit You” (Ask a Manager podcast episode 2)

This is a transcription of the Ask a Manager podcast, episode 2: “I Can’t Quit You”.

Alison: Hi, I’m Alison Green. Welcome to the Ask a Manager podcast. Some of you may know me from my website,, where I answer daily questions from readers about how to navigate all sorts of sticky situations with coworkers, managers, and employees. Each week on the show I’ll take calls and talk directly with listeners about the toughest, most frustrating, or just plain weirdest work predicaments they’re facing. I’ll help you figure out what to do and say to handle these situations successfully and get the outcomes you want. So let’s get started.

I hear a lot of questions at Ask a Manager about resigning. How to do it, when to do it, and what your obligations are when you’re leaving a job. And while most employers understand that people leaving is just a normal part of doing business, even if they’re very disappointed to be losing you, occasionally an employee behaves pretty badly around a resignation. That can mean acting like it’s a personal betrayal that you’re quitting, or expecting you to do way more work than what’s reasonable as part of your exit.

This week our guest is someone who’s dealing with that last situation. I’ll let her tell the story. Hi, and welcome to the show.

Guest: Hi Alison, thank you. I worked for a small nonprofit for 10 years. I loved the work and I loved my coworkers, but I dealt with an abusive boss. I recently gave notice and I left the company. Within 24 hours, I had a new job in the same field that’s a really good fit.

While my boss was really abusive, my coworkers and the agency’s mission were laudable, and I have no interest in harming my former boss. So I agreed to train my replacement until I was satisfied that she would be able to adequately replace me. However, my former boss ended up hiring someone completely unqualified and after three months, I am still training several hours a week with no end in sight.

Complicating the situation, it’s a small industry, and while my former boss is not well-liked, he could do significant damage to my reputation if he claimed I deliberately tried to sabotage his agency by reneging on my agreement. So how do I ethically extricate myself from the situation, knowing that there’s literally no one else to train her and the organization will be in significant financial trouble if she is not trained adequately? Where does my ethical obligation end?

Alison: Well first, good for you for getting a new job that you’re happy with in just 24 hours, that’s fantastic and it speaks so well of you and your skills. You must have been so pleased when that happened.

Guest: It was amazing. (Laughs)

Alison: Yeah, that’s really great. So tell me what led you to make this promise about training your replacement. Did you offer to do it because you were worried that things would fall apart, or were you pressured into it?

Guest: I offered to do it because I was afraid things were falling apart. When you work at a nonprofit, inevitably you take on more and more and more responsibilities, and I knew the workload I was carrying, and I also knew that he was going to have to hire a few people to replace me. I was really worried because no one else in the organization knew how to do what I was doing.

Alison: I don’t know if you know that I worked in nonprofits my whole career, so I know exactly the dynamic that you’re talking about. I think you’ve fallen into a trap that is really common in nonprofits, you have a lot of company in this trap. And that is that you feel a much higher degree of obligation to your old employer than is really warranted. At nonprofits, this thing happens where you feel such a personal commitment to the organization’s work. And depending on the organization you can feel like you’re letting down its mission when you leave, and certainly your coworkers. And so as a result, people often really want to go out of their way to make their departure as easy as possible for the organization and for their coworkers. And it can lead them to offer things that you don’t see people offering at all in the for-profit sector.

That can be a lovely impulse when it means things like, “I’m going to document my projects really thoroughly, and I’m going to be available for a couple of phone calls after I leave.” But you’ve taken it a lot further than that. When you made this promise to train your replacement until you were satisfied that she could do the job, you were promising too much. I’m sure you thought it was not going to take this long, but more often than not when people leave their job they don’t get to train their replacement at all, just because that’s the way the timing usually works out. And their employers do make do. I mean, it’s inconvenient, but it’s the nature of doing business. It’s just how this stuff works, and they figure it out, and life goes on. Most people aren’t doing any work at all for their old job after their last day, and even when you feel like you’re indispensable and things will fall apart without you – I mean, I know that feeling. But I promise you that most people, even in nonprofits, do make a clean break when they leave. The organization figures out a way to hold it together, and it’s totally normal and okay.

But I get that you did make this promise, and so now you feel like you’re stuck because you have to keep it. But the fact that you made the offer doesn’t bind you to keep training the person indefinitely. I’m sure that when you made that promise you assumed that your boss would hire someone qualified and that the training period would be much shorter than this, right?

Guest: Absolutely, yes.

Alison: And that was reasonable for you to assume. Let me ask you this too: have you told your boss that your replacement isn’t catching on as fast as you’d expect, and that you’re kind of concerned about whether she can do the job?

Guest: I have not stated it directly, I have beat around the bush on it and said, “She’s having some difficulty. She doesn’t really understand organizational systems. She doesn’t really understand this.” Maybe I haven’t directly said to him, “She’s really unqualified and I don’t think that she’s going to get this.”

Alison: What’s his response then, when you’ve said the things that you have said? Because any manager in his shoes hearing that should know that those are pretty serious alarm bells ringing.

Guest: He’s asked to schedule more training dates. (Laughs)

Alison: (Laughs) Of course, okay. All right. It’s reasonable for you to go back now and explain that this is a much larger time commitment than what you were envisioning. You know, you were assuming that someone would step into the role who was going to be competent at it. So it’s reasonable for you to go back and say you’re not going to be able to train her indefinitely. Frankly, it would be reasonable for you to just say now that you’ve given it three months, and you can’t keep doing a period, and they should just accept that and be grateful for what you’ve already done for them, but I know the guilt that can be involved in these situations. I know what it can be like to deal with an unreasonable boss who’s hearing a message he doesn’t like. I know you’re worried about him maybe hurting your reputation if he’s angry.

So I’m going to suggest a way to word this that’s going to take those things into account. And I want to be clear: you don’t owe them a reason for stopping your work for them. I think you should say that your new job is keeping you increasingly busy, that you just no longer have the time available to keep doing this. And you can sound regretful about it – even if you’re not regretful, you can sound regretful about it, which might help. And I suspect – tell me if I’m wrong about this, but I suspect you’ll feel more comfortable if you don’t just cut them off cold turkey, but instead offer to do maybe one final call with your replacement. And you can frame that as a concession that you’re making.

Guest: Okay.

Alison: You don’t owe them any concessions, I want to be really clear about that. You’ve already gone way beyond what you owe when you’re leaving a job. But I think including that will make you more comfortable. So before I suggest actual language to use, does that sound right to you?

Guest: That sounds good. And I think you’re spot on. I do feel really guilty, I feel really invested. This was my first job out of college, I really grew in my position, and grew the position. So there’s an emotional investiture there.

Alison: I just want to reiterate, I know I keep saying it, but it really is so normal to make a clean break and it’s okay that you’re doing this. So I would say something like this: “When I offered to train my replacement, I assumed she’d be up to speed pretty quickly. It’s been three months, I’ve spent hours working with her, and I’m worried she hasn’t picked up the job the way she needs to. My work schedule is keeping me increasingly busy, and it’s at the point where I can’t do more than the three months that I’ve already put in. So I need to hand her training back over to you at this point. I know you’re in a crunch, so I can do one more phone call with her for any final questions. And I wanted to give you a heads up now so that you can make sure that any final things you might need from me are included in that last conversation.”

Guest: Okay.

Alison: What do you think? Could you say something like that?

Guest: I absolutely could. I think there’ll be pushback (laughs), but I think that that’s a really great way to word it. And it has the virtue of being the truth – I’m increasingly busy.

Alison: I think if you do get pushback, and it’s great to be prepared for that so that you’re not… sometimes if you don’t prepare yourself for that, and the pushback happens, people will just give in because they don’t know what else to do in the moment. So assume it’s going to happen and plan out, you could even write down ahead of time what you’re going to say. Sometimes that helps to have it right in front of you. And again, you can sound really regretful, you know, “I’m so sorry, I know this is a difficult situation for you guys, I’ve really put in hours with her. I was hoping we would be done by now, she’s really having trouble with it. I wish I could help more, but my commitments at my new job are getting overwhelming.” So if you sound regretful, you’re completing your end of this weird emotional transaction that your old boss has you caught up in where you’re sort of paying lip service to the idea that you owe them anything, because frankly you don’t. But since he’s acting like you do, you might as well sound regretful. It’ll make it a little easier.

Guest: (Laughs) Okay.

Alison: Even a lot of unreasonable bosses would hear this and ultimately be okay with it. You know, the fact that you get pushback does not mean that he won’t ultimately accept your answer, so keep that in mind. There’s nothing to be sorry for here, this is just about softening the message a little bit to preserve the relationship if you can. And I wouldn’t worry too much about him badmouthing you for this. He probably won’t, but if he is so unreasonable as to badmouth you over something like this, then honestly he’s so out of his gourd that people already know that about him and aren’t likely to put much weight on anything he would say about a situation like this. Do you believe me about that?

Guest: Yes, I do. And, yeah. (Laughs) It could go either way, yeah.

Alison: Okay, good. So, my parting advice is really just to remember, it’s so normal for you to set a limit here. You’ve already gone way above and beyond what most people would do. Your promise to help out is not a promise that you’ll be bound to them indefinitely. You get to say, “this is the limit of what I can do.” And you get to say that you need to focus entirely on your new job now, or for that matter, on lounging around on your couch and watching TV if that’s what you want to do with your time. Now that you’re not working for them, you get to stop working for them. I hope that helps.

Guest: It does help, thank you very much.

Alison: Thanks for listening to the Ask a Manager podcast, produced in conjunction with Penguin Random House and Anchor. If you like what you heard, please take a minute to subscribe, rate, and review the show on Apple Podcasts, Spotify, or Google Play. If you’d like to ask a question on the show, email it to And check out my new book from Ballantine Books called Ask a Manager: Clueless Coworkers, Lunch-Stealing Bosses, and the Rest of Your Life at Work. It hits stores May 1st, and it’s the ultimate guide for tackling any and all workplace dilemmas. You can pre-order a copy today at or anywhere books are sold.

Thanks for listening! I’m Alison Green, and I’ll be back next week with another question.

Transcript provided by MJ Brodie.

You can see past podcast transcripts here.