how to adjust to a new job with extreme flexibility

A reader writes:

I just started a new job last week, and it is nontraditional in the sense that there isn’t really a set office: The company is so small that we each just have a membership at a coworking space, our cells are our main phone lines, and people are often out and about for meetings. I basically stay in the “office” unless I’m accompanying someone to a meeting. Everything can be done online, so often people just leave early and work from home or sometimes just don’t come in at all.

This is great, but since I’m used to working in traditional offices, I’m not sure when I can start saying I’d like to work from home on certain days since I’m so new. When do you think it would be appropriate? A lot of days, I find myself done with my work pretty early and would love to beat the traffic, but I wait around until the last person leaves or until a little after 5 p.m. It seems that they would be fine if I starting leaving early as long as I’m finished with my work, but I’m nervous and I’d like your opinion first. I’d really like to make a good impression, but I’m not sure if they would even think twice because everything is so laid-back.

I answer this question — and four others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

{ 66 comments… read them below }

  1. SirTechSpec*

    Another priceless stock photo!

    One tiny issue – in the last answer, where it says “hiring for Y” I think it should be “hiring for X”.

  2. Jack the treacle eater*

    #2, I’m just thinking of situations where I’ve had people who found certain things difficult – an employee who was scared of the new, larger forklift, for example. Presumably the employee is otherwise valued; is there something practical the OP could do to help them – arrange foul weather driving tuition or skid training with a sympathetic trainer, for example?

    1. Elizabeth West*

      Good suggestion–and consider the vehicle as well. Is it a large one? Sometimes people are uncomfortable driving a larger vehicle than they’re used to, especially when the weather is bad. I’d also make sure the vehicle is well maintained and has good tires, etc. in case someone else is supposed to be doing it and isn’t.

      1. Gene*

        We dealt with this on FormerJob. One of the interview questions was, “Can you drive a stick?” We discovered with one hire that a yes didn’t mean she was comfortable driving what was essentially a bread truck (GMC ValueVan from the 70s) and she just refused to drive it. I was her work partner at the time and enjoy driving, but driving every day became a bit of a BEC situation. Finally one morning I announced I had “forgotten” my wallet and she was not only buying lunch that day, but she was driving. That was all it took, one day of being forced to drive it, and it broke her fear. I still drove most days, but that was by choice.

    2. irritable vowel*

      I’m not really clear on why the woman took this job that mostly involves driving, though, if she is afraid of driving to an unusual degree. (I’m assuming that she didn’t relocate from a different part of the country to take this job, so is familiar with the climate.) Either she didn’t really think it through, or she thought she could power through the fear and/or get other people to help her out. I think at this point the OP needs to make it clear to her that if she can’t handle what is a significant component of her job, it’s not going to work out. I don’t think the company should be offering her training on something that is basically what she was hired to do (ie. a skill/ability she was assumed to possess). If she wasn’t told how much driving the job would involve, then that’s different, but that’s not clear from the letter.

      1. C Average*

        In principle you’re probably right, but why not be the bigger person and offer her the training anyway? It could conceivably provide a solution to the problem for everyone–the company gets to keep an otherwise solid employee and doesn’t have to go through the hassle of managing her out and finding someone new; the employee solidifies a skill that’s been a little shaky in the past.

        1. Dr. Johnny Fever*

          I think it depends upon the criticality of the work and the type of vehicle, as well as skill vs. will. Does the driver needs new skills, or just not want to do it? One can teach skills but not will.

          If she’s driven a van but not one this size, then training would be kind.

          If she needs something closer to CDL training, that’s not on the employer to provide.

          The OP needs to determine how much she’s paying this driver, the hours the others are putting in to cover, the cost of training, and the expectation of driving hours to determine if it’s cost-efficient to keep this driver or hire someone with the skills, experience, and willingness.

      2. Jack the treacle eater*

        @ “irritable vowel”, I don’t know. There are lots of possible reasons why she might not have considered it when she started the job, not least that people, and confidence, change over time; but in a way I’m not sure this matters; they are where they are now. Assuming the employee is valued and productive, to make it a choice of “drive or leave” without exploring alternatives seems unreasonable – not least because if the employee leaves the employer will also incur significant costs in recruiting and onboarding a replacement.

      3. INTP*

        She could have relocated from another region and underestimated how difficult the winter driving would be. When I moved to a place with snow, everyone told me that driving in the snow is “easier than driving in the rain”…yet with every big snow there were pileups on the freeway and the one time I drove in like a cm of accumulation, my car skidded through an intersection. I was skeptical of the people telling me that winter driving is easy so I didn’t take on any commitments I couldn’t manage with a bus, but I could see someone being far more overwhelmed than they anticipated.

      4. Vicki*

        Or they didn’t really make things clear in the interview. I think the OP needs to consider how the interview questions were handled.

        Did the job description state: “Requires driving to sites in many types of weather year-round”?

        1. Victoria Nonprofit (USA)*

          And if it didn’t? The job still requires it, even if the posting was imperfect. The employee doesn’t get a “get out of job free” card because the description was poorly written.

      5. Joanna*

        It’s possible she took the job in good faith and is now for some reason finding the driving requirement more difficult than she anticipated. Driving it the wet never used to bother me until I was in a car accident on a wet road last year. Even though the accident didn’t result in an injury, ever since then I’ve found driving on wet roads unsettling and scary.

    3. KR*

      I agree with training of some kind! A lot of time in cold or slippery weather people are just scared by slipping at all. The secret of driving in the snow though is that your car will move unexpectedly but if you turn slowly and can manuver the car correctly when it doesn’t stop quickly or slips going around a curve you can avoid an accident. It might do good to let her know that the company has insurance and if snowy weather causes an accident, she won’t be held liable. She might be scared of damaging a company vehicle.

    4. INTP*

      I think driving lessons are a great idea. To be honest, I struggle with the ethics of even telling her “This is required for your position, you can do it or find a new job” because the last thing that you want is for someone who is unsafe driving in poor conditions to do so anyways because she’s afraid of getting fired. We don’t actually know that she’s “overly” nervous – she could really not be safe to drive in the snow (because of lack of experience, being an easily distracted driver in the first place, or whatever other reason). With driving lessons, not only does her confidence ideally improve, but you also know that she is reasonably safe to drive in the snow if she passes them.

      Actually, I didn’t drive in snow (except for 1 cm of unexpected accumulation) the whole 3 winters I spent in Wisconsin. I don’t think that I would have been safe to do so without some sort of training. I bought snow shoes because I didn’t even realize I could walk on the snowy sidewalks without slipping and falling…apply that level of ignorance to how tires work in the snow. No adult that taught me to drive had ever driven in snow, it wasn’t mentioned on my license test, etc – it was a 100% foreign concept.

      1. the gold digger*

        I had to drive to the shop to get the snow tires put on the morning that there had a been a huge snowstorm and the plows hadn’t gotten to all the roads yet. The light turned yellow and then red before I had time to stop and I knew I was going to slide right through that intersection.

        I leaned on the horn and prayed.

        Fortunately, everyone was driving very slowly and very carefully, so I was not hit. But it was very scary. I hate driving in snow.

    5. Tinker*

      About in the first week of my first job I had the following conversation with my boss:

      “And here are the trucks. Do you drive stick?”
      “Not really, I haven’t had much chance to learn.”
      “Then I’ll drive, and Bob will teach you to drive stick. Next time I expect you to drive.”

      I now don’t own an automatic transmission vehicle.

    6. Bunny*

      I have significant spatial disabilities. I’m high functioning, but on the spectrum. I was 23 when I learned how to drive. I cannot drive the giant SUVs at work well. I cannot park them. I CAN drive my much smaller AWD Subaru.

      She might have thought she could do it. It took me a loooong time to learn to handle snow.

      1. NutellaNutterson*

        I happily tell people “I *can* drive something bigger, but last time I did, I hit things. Repeatedly.”

        It’s all conveyed in the cheerful voice that Alison recommends. And I’ve never had to drive something other than my subcompact.

  3. Jack the treacle eater*

    #4, it sounds as though the moment to say ‘this is unethical’ is past – is there any reason to say anything (other than I resign effective X date) unless asked to an exit interview?

  4. The Other Dawn*

    RE: #1

    It’s really hard to go from an office where the boss wants to account for every minute of your time and you need to be at your desk, to one where people do what needs to be done, when it needs to be done. This was a difficult adjustment for me when I left Old Job I Hated to come to the new job. At Old Job, I was hourly, non-exempt (after years of being exempt and salaried) and my boss was very anal about everything, so I eventually got used to having to be in the office from 8 am to 5 pm. Not a minute earlier and not a minute later. I couldn’t work from home, because it was only allowed for the executives. When I left and came to this job, it took me several months before I felt like I could leave before 5 pm and come in at 8:15 am (or later or earlier). I always worried about whether my boss would think I’m a slacker, or that I don’t care about the job. But my boss cares about results, not butt-in-seat time. It’s been over a year now and I work the hours I need to work to get the job done, which average about 40 a week, and make sure I’m here if I’m needed outside those hours (meetings, training, vacations, etc.). Boss usually asks me, “Are you here tomorrow?” I love it.

      1. Vicki*

        One thing I would add… I think the OP needs to have a 1:1 conversation with her manager about this.

        From the outside, looking in, we’re saying “feel out the company, give it a few months, put in some time first…”. But from the description of the company, I’m guessing there may already be some people who are wondering “What’s wrong with her? Why is she always the last person to leave the office/ Why is she always in the office? Is she having trouble getting her work done? Is she slow? Does se need a phone? A computer? Internet service?”

    1. Sunshine Brite*

      Same here, we have multiple sites, open floor plans, I couldn’t wait to hear more about flex options. As part of getting to know the place I ended up asking something along the lines of ‘I see there’s a lot of flexibility here. What are the expectations around that?’ In a one on one and my supervisor took it from there.

    2. Vicki*

      Yeay for you!

      At LastJob, a co-worker moved into our team from the Call Center with a similar culture shift. It took us a few months to break him of thinking he had to tell everyone every time he left his desk, where he was going, and for how long.

      No, in the non-Call-Center teams, you don’t have for permission to go to the restroom.

  5. Daisy Steiner*

    It’s even more important that the gifts are roughly the same value, IMO, because this is meant to be a milestone of time rather than achievement – quantity rather than quality, to put it crudely. You’re rewarding loyalty and long-standing at the company – and they’ve both done that in equal measure. If you were rewarding more variable ‘qualitative’ achievements, I’d feel differently.

    1. irritable vowel*

      That is a good point. I also think the proposed gift for the higher-level person is excessively lavish and will possibly cause tongues to wag just in general, not only if presented in coordination with the lesser gift. If you wouldn’t give the more lavish gift to the person in the lower position because it seems like too much, then you probably shouldn’t be giving it to anyone.

      1. C Average*

        Yeah, and it’s especially insensitive given that the C-suite guy probably earns a salary that would enable him to spring for his own lavish ski trip (should he desire a lavish ski trip), while the admin’s salary may not.

    2. SMGW*

      Very well-said; you put my finger on what I was thinking but couldn’t articulate. If I were the AA in this situation I’d be pretty taken aback, since 20 years of whatever work your’e doing is still a full 2o years of your life.

    3. Ruffingit*

      I completely agree. I cannot imagine being the admin in this situation and seeing the upper-level guy get a lavish ski trip complete with air fare while I received a driving-distance hotel stay. Quite honestly, I might just quit on the spot at that point because for me I’d be seeing it as almost a giant f**k you, you’re not valued statement. And on a somewhat related note, I think admins need to stop being undervalued to begin with. Sure, C-level guy managed teams, etc, but the admin made it possible for him to do that because he didn’t have to worry about the smaller details that underpin the operation. She took care of all those things. Give the woman some credit. Without the bottom of the pyramid being solid, no one is standing at the top.

      1. JessaB*

        Thank you, I was going to come and say this. Not only did this admin stay as long as he did, but you dunned her pay every year during slow season. Did you do that to him? Probably not. Have a serious sit down and take a piece of paper and map out all the things she did to keep the company going. Because seriously, I don’t think she’s very valued by what the OP says.

      2. Miss M the Admin Clerk*

        I can completely see this. Sales people at my company get fancy trips and nice gifts and Admin gets squat.

        And the Admin in this situation can see this happening too.

  6. CeeCee*

    #3: Would it maybe make more sense to give each employee the same, but smaller gift as a 20 year service award, and then privately give each the separate gift you’d like (but frame it more as a performance achievement rather than a years of service award)?

    That way it would differentiate it from the 20 year award (which they both received fairly) but you’d still be able to thank your employees for what they do with a gift that reflects their responsibilities, etc.

    1. Artemesia*

      I’d do this. Give them watches or gift cards to local fancy restaurant or whatever as part of the celebration. Give the more valued employee a bonus quite separately. I’d make it a cash bonus.

      1. Koko*

        I would be OK with this if I were the admin, especially if the company has a practice of awarding bonuses in general. (I would not be OK with getting the third-rate vacation next to his first-class one.)

    2. Roscoe*

      Yeah, I agree with that. This to me goes with the “fair isn’t always equal” thing. I mean, yes they have been there the same amount of time, but one person’s job is much more valuable to the company, and likely has a lot more risk involved too. I don’t really have a problem with giving them different gifts, but definitely don’t do it at the same time.

      1. Fish Microwaer*

        Yes and presumably the “more valuable ” person’s contribution has been reflected in their salary .

  7. Long Time Reader First Time poster*

    OP#1: I’d make some efforts to build up my communication channels now — make sure you are talking to your colleagues regularly over chat and email. That way, once you are not in the office, they will already be accustomed to communicating with you in that manner, and communications will feel seamless to them whether you are in the office or at home.

    Additionally, be extremely cognizant about responding as quickly as you can to communications that come in during standard work hours. That means that if you do knock off early and go run some errands, you are watching your messages on your smartphone. If something important happens, you want to be on top of it.

    In my fairly extensive experience in working remotely, nobody really cares if you are remote as long as you don’t *feel* remote.

  8. JM in England*

    Re: #1

    At least one third of my working life so far has been in contract roles. Because of this, extreme flexibility has become a necessary survival skill. A good example of this was when I started a contract job some years ago. The reason they were hiring was because they had two scientists in their quality lab, one of which was on long-term sick leave and the other was about to go on their annual month-long holiday. During my first week there, I was trained in the workings of the lab by the holiday guy; after that, I was left to run things single handed. This impressed my then-boss. However, even the boss could see that I couldn’t keep this up forever so he hired another person from my agency at the time & I then trained him up.

  9. Kimmy*

    On the anniversary gifts, for the employees that hit huge tenure milestones, our employer provides you a salary based bonus. Example-2 weeks pay if you hit 25 years. Seems like applying the exact same formula to both employees would provide a fair application, but still result in different valued amounts.

    1. Tommy*

      Yes this kind of situation, where you want to give more to the person who already has more, is exactly what percentages are for. A 10% bonus would capture this difference very accurately.

  10. C Average*

    I can speak from the other side of the short-timer situation, having worked for a company where people tend to either love or hate the culture and where it’s not unheard-of for people to figure out pretty quickly that they’re not a fit and find opportunities elsewhere.

    It happens. We all know it happens. It’s sort of like going on a couple of dates with someone you really liked at first and then realizing you just don’t click. At that point, there’s kind of an unspoken agreement that you’ll say “You’re great, but I’m not really feeling a spark” and go your separate ways. You don’t say, “You smell weird and dress badly and have questionable principles and you’re not as tall as your online profile indicated and I’m moving on to someone better and I’m going to tell all my friends to stay away from you, too, because even from our brief acquaintance I can tell you are really bad news.”

    Be polite and brief. Don’t be the unhinged ex.

    1. Ruffingit*

      So agreed! Not to mention the fact that, in my experience, company cultures do not change unless a major situation forces it. So the OP is being naive in my view to say ” I don’t want to burn any bridges, but I do want to let them know why I’m leaving so that they can hopefully improve things for those that are still here if they choose to.”

      They already know and they do not care to improve. The OP is not the first short-timer most likely and won’t be the last. It’s not worth trying to “educate” employers on their short comings unless said short comings are illegal. Otherwise, just move along. You’re not the Company Culture Whisperer.

  11. Artemesia*

    The most important thing when starting a new role is to manage impressions. Thus the advice to put butt in chair for the first couple of months and to establish a high level of manageable productivity is important. Once you are known as hard working and productive, you can then begin to be more flexible. In this situation think about how you will make your productivity clear to your manager. Can you update him weekly with achievements, or is there a natural assessment as there is with sales? Finding routine or even informal ways to make sure your boss knows you are successful is important in many jobs and triply so if you are flexing your time or working from home.

    I once started in a new department where my strength was dealing with difficult clients. For the first two months, I scheduled a large number of client meetings and left my office door open so as my new colleagues walked by there I was hammering something out with a client. This established my reputation as being ‘great’ at a task most of them didn’t want to do but valued. It gave me enormous freedom to organize myself as I wished once that was done.

    Be intentional and mindful of how you establish yourself in the new role. Then you can say ‘I find I can get more TPS reports done if I work at home where it is quiet and less distracting the ‘officetown’ and so I will do that thursday and friday — I will be available by Email if anyone needs me.’ — Again here you are stressing your commitment to productivity that is measurable and your availability even if not on site.

    1. Persephone Mulberry*

      This is valuable advice, thank you. I’m also moving from a butt-in-seat job to one with a more flexible clock (although not “midair splits in a business suit” flexible) and I’m more nervous over “what time should I arrive? How late should I stay?” than I am about actually learning the job.

      1. Lizzie*

        “Midair splits in a business suit” is my new top of the range for flexibility. Thank you so much.

  12. DatSci*

    I couldn’t disagree more with the advice given in #3. It is obvious that the employee who provides more value to the company should be recognized with a higher value gift. It makes logical sense that the Operations Manager earns a higher salary and possibly more lucrative benefits than the Admin. This gift is part of the recognition package and should reflect their individual contribution accordingly. Twenty years of providing value as an Admin Assistant is not the same amount of value as an Operations Manager.

    However I do agree that when giving different gifts (as is appropriate here because these employees do different jobs), it should be done privately and the nature of the gifts should be kept private. The concern which AAM raised is likely moot, since the Admin should not “uncover” the value of the Operations Manager’s gift just like the Admin would not find out the Operations Manager’s salary or other compensation consideration.

    1. IT Kat*

      Agreed, with one caveat – if you’re basing this on the employee’s value (which both you and the LW are), then it shouldn’t be a “years of service” gift, it should be a performance bonus.

      Give them both the same “years of service” gift, then give a “performance/value” bonus to the Op Manager. Problem solved.

      But I think that’s where most are getting stuck – this is being framed as a years of service award, when actually, it isn’t.

    2. Tommy*

      Except when someone asks the manager what he’s doing for vacation and he tells them. I guess you could swear him to secrecy, but it’s a lot easier to just give him a bigger bonus, which people tend to keep secret anyhow.

    3. Fish Microwaer*

      Just because the roles are different and are different level on the totem pole is not indicative of performance within those roles. The Op manager might be a nightmare who has been allowed to remain for 20 years while the Admin has performed beyond diligently for the same time. Meanwhile Op man nightmare has been drawing a salary that reflects their position in the hierarchy. If we are rewarding time in service, we need to do that equitably. Apercentage bonus is one way of doing this.

    4. Anon Admin*

      Who processes the contracts? Who maintains the files? Who keeps track of those sales? Who does the books? Who answers the phone?

      Yes, the Senior Admin will know about the fancy pants trip because all the paperwork required for it goes through her.

  13. HardwoodFloors*

    I was hoping for comments about how to fit in on a new job. I have the 180 degree situation. I went from a very flexible job environment to one where the norm is to spend extremely long days, 10 hours ‘butt in the seat,’ to the point of skipping lunch sometimes. I am trying to figure out if I fit in (or even want to) because I find myself dehydrated when I go home. (Taboo on any fluids (even water) at desk and no food at desk.) No culture of taking turns bringing in the donuts…I am not a fan of donuts calorie-wise… but I like sharing good experiences with co-workers and this place seems to have a deadly serious, lack of friendlyness (if it is a word) culture.

    1. Tommy*

      Wait, people skip lunch AND can’t have food at their desks? That sounds pretty sucky.

    2. Koko*

      I am not being hyperbolic when I say I would quit any job that wouldn’t let me have water at my desk in under a week. Water is a human right.

      1. HardwoodFloors*

        Well, we do work in a laboratory and all labs I have previously worked in do prohibit eating or drinking so workers don’t inadvertently poison themselves … but the other work places have ALWAYS had another area where the workers had their desks out of the lab physically. And previous work places allowed drinking water, etc at the non-lab desk. This job has all the desks in the laboratory and the workers have a break area far, far away and I am not sure what I am going to do.

  14. Rachel B*

    This appears to be the same question and answer that was posted in December 2012. In the “You May Also Like” section at the bottom of this post, in the link that says “wee answer Wednesday….. ” this question is also in that post. Do you sometimes repost old columns without indicating it as such? Just wondering… Love the blog, regardless!

    1. Delyssia*

      I think you may have skimmed a little too quickly, because this is clearly described by Alison as “revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them).”

  15. AJ*

    I work at an extremely flexible company (we do have an actual office though) and what I’ve learned is that communication becomes even more important. I keep my calendar up to date (being very clear when I’ll be OOO or WFH or Unavailable if I’m leaving early).

    Honestly, I usually tell new employees that I expect them to come into the office and during normal-ish hours until they get comfortable with the work they are doing. The reasoning: it’s much easier to get help on something or a second opinion when you’re sitting right next to them. Once they are around 80% there, I have no problem about them coming in later, working from home, etc. It’s a conversation I have with my reportees every week during our initial few 1:1’s mostly so I know how they are doing learning the ropes. For some people it takes 2 months to get to that place, for others, 3 weeks.

    I think the main reason behind a flexible working structure is to focus on results and what you’re getting done rather than the number of hours you worked, etc. So, I’m pretty sure your manager wants you to use your best judgement on when to work from home, when to leave early, etc. I always stress communication (like telling your manager, I focus a lot better at home so I think I’m going to start doing that once a week) and they most likely won’t really worry about it unless your work suffers. I know I don’t. As long as my team’s consistent and they keep me in the loop when I need to be, I don’t worry about these things.

  16. Gwenderful*

    Re #3 – I agree – both should get the same award for years of service. Presumably the Ops manager has been recognized for his higher level contributions the whole time – with a higher salary than the admin. If the admin and the ops manager are making the same wage then that’s something to address with payroll, but I’d bet dollars to donuts that the ops manager has been out-earning the admin for some time.

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