I manage a team of lovable screw-ups

by Alison Green on July 25, 2017

A reader writes:

I’m 30 years old, I work at a small start-up and I manage a small team. Before I was here I was at another start-up where I managed a slightly larger team, and before that I worked and interned for some very well-respected Fortune 500 companies. I’m used to pretty buttoned up environments, and while I didn’t always agree with the bureaucracy that came with them, I developed the skills that you expect to get from places like that – i.e. how to build process, develop strategy, and execute in a fairly rigorous setting.

Which brings me to my current spot. I’m managing this team and, well, I find them to be lacking! I adore them as people, but their inability to articulate, let alone structure and manage projects, drives me insane. This start-up has a pseudo-flat culture, which means that while there are department heads (I’m one), projects are designed pretty ad hoc across the whole organization, which doesn’t help my cause.

I’ve found on multiple occasions that members of my team had – independently of one another – kicked off projects that I’d never even heard of, let alone approved. It’s not just the over-eagerness that bugs me, it’s that the projects are bad and poorly thought out.

The first time it happened, I had conversations where I tried to suss out what it was that they wanted to achieve and helped them understand the underlying logic needed to better structure their projects for success. When it happened again, I held a team session to revisit the process and also work together to make some adjustments to incorporate some of their natural inclinations and concerns into the process. Fast forward eight months later, nothing has stuck and I routinely feel like the mom who turns her back only to find that the dog shit on the carpet and the baby has puked on the walls.

I’ve never experienced anything like this before. I do teach-ins, weekly meetings, team lunches, send them to conferences and events, developed a goddamn LEARNING CHANNEL ON SLACK, WHICH I HATE, and they’re still a mess. What keeps me up at night about these rogue projects, is that they are so half-baked and they don’t realize that on their own. How do they think these are good ideas? HOW SWAY?! I’d feel mutinied against if the glaring ineptitude didn’t incline me to think otherwise.

What do I do? They’re good kids, but they keep biting off more than they can chew and hindering our team’s efforts in the process. I routinely want to shake them all violently in hopes of getting the synapses to fire more efficiently. Am I being too tough on them? Too lenient? I’ve never micromanaged before because I’ve always been taught (and experienced) that good systems and open communication lead people to better outcomes, but now I feel like it’s coming to a point where I might have to. Basically, how do I get my team to follow my lead and more importantly, how do I shore up my patience until that day comes?

When you’re this frustrated with people working for you, you’re either not giving clear enough guidance or you have the wrong people on your team.

Let’s start with the first. How clear have you been with them about what you do and don’t want to see from them? Have you explicitly said, “I need you to talk to me about projects before taking them on, and I need to approve any new project?” Have you said, “When you bring me a project proposal, I need to see that you’ve thought through factors X, Y, and Z?” And when those things didn’t happen, have you said, “Hey, we talked about how I need to approve things ahead of time but this moved forward without my knowledge. What happened here?” That last part is how you hold people accountable for messing up — and if that’s not happening, it’s no surprise that you’re seeing the same problems occur over and over.

And have you given them specific feedback both on their work itself and on the broader patterns you’re seeing? The former is this kind of thing: “Right now this project doesn’t address budget and it’s not clear where your marketing projections come from. Can you make revisions to address those?” The latter is this kind of thing: “We’ve talked several times now about projects that are missing key details I need in order to be able to sign off, but I’m continuing to see work come to me without those elements. I’m concerned that it’s become a pattern. What can you do differently so this doesn’t keep happening?”

That second type of feedback is particularly crucial. Managers often just talk about specific incidences as they occur and figure that the employee will connect the dots and realize there’s a pattern, but never actually say, “Hey, there’s a pattern here.” But if you don’t name it and explain that it’s a serious concern, some employees truly won’t realize it.

Maybe you’ve been doing all of this, but your letter sounds like you’ve been leaning heavily on a collaborative approach and not being as directive as the situation probably requires. It’s great that your instincts are to be collaborative, but your staff might instead need very, very clear structure and boundaries and more limited roles than what you’ve currently given them — at least for now.

That doesn’t mean that you should micromanage — but right now it sounds like you’re on the opposite extreme from micromanaging, where you’re giving people more leeway than they’ve shown they can handle. It sounds like you need to get more hands-on in setting clear expectations and ensuring you’re all on the same page, checking in regularly as work progresses, giving feedback while work is ongoing (not just at the end of a project), and addressing it forthrightly if your expectations aren’t met. Those things aren’t micromanaging; they’re really just … managing.

If you do all this and you don’t see marked improvement, or if you’ve already been doing all this, then it’s time to seriously consider that you might have the wrong people on your team.

One thing to consider in that regard: Are they all pretty young? You called them “kids,” so I’m guessing yes. It might be that you or whoever hired them just hired at the wrong experience level — that for the type of work you expect, you need people with more experience and professional seasoning (which often means better-developed judgment).

However, before you go down that road, try investing about a month in making sure you’re being as clear as you can. During that month, don’t let fear of being labeled a micromanager deter you from being really, really explicit about where people are going wrong and what you need to see instead. If you feel weird about that, keep in mind that doing it will give them the best chances of success, so it’s really a kindness to make sure that the messages you’re delivering are loud and clear.

But if you do that and it doesn’t produce significant changes, then you can know with a pretty high degree of confidence that you’ve got a team that doesn’t take feedback and can’t or won’t do what you need. And that’s the wrong team, unfortunately. At that point, you’d need to start thinking about how to make some pretty big changes on your staff and bring in people who can do the work you need done.

Originally published at New York Magazine.

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{ 112 comments }

{ 112 comments… read them below }

  1. Nico M*

    Why bother? Sit back, put your feet up and play with your own resume enhancing hobby projects. If disheartened remember those projects at BigCorp that were so well planned and rigorous they were immediately obselete.

          1. Nico m*

            I think the real problem is above the LW not below

            “Ive been here 8 months and nobody cares what i achieve”

            1. Blue Anne*

              Uh, where are you getting the idea that no one cares what LW achieves? I can’t see anything to indicate that…

              2. Game of Scones*

                “When it happened again, I held a team session to revisit the process and also work together to make some adjustments to incorporate some of their natural inclinations and concerns into the process. Fast forward eight months later, nothing has stuck”

                That was 8 months after the team session. We don’t know how much time passed before the session.

    2. Natalie*

      your own resume enhancing hobby projects

      As the manager, I’m fairly sure this *is* her resume enhancing project.

    3. Antilles*

      Because it actually matters.
      1.) Even in a start-up culture where the goal isn’t necessarily showing an annual profit, other managers will eventually realize that all of OPs team members haven’t produced anything of value. In fact, if these other managers themselves have decent judgment, they’ll probably put some portion of the blame on OP for poor leadership/training/etc.
      2.) If OP wants the company to succeed, having employees working on doomed projects is just a waste of company resources. Many start-ups include either stock options, profit-sharing or potential for growth, so there’s a clear reason why you don’t want your employees wasting time on near-guaranteed failures.
      3.) Those ‘resume enhancing projects’ aren’t going to be nearly as dazzling to a new employer if they come with a side of “…and the company went bankrupt”.

    4. Not So NewReader*

      It’s true nobody has to do anything.

      If I had to work this way, I’d quit the job. I need more out of job than just collecting a paycheck.
      If a company is not thriving then it’s dying. There is no middle area because the middle area does not last. The company either gets better or it gets worse.
      Some people believe that businesses will go on forever. And that is not true. Everything is finite.
      A boss has an obligation to help her people remain employed. OP realizes this.
      I have had bosses who hid in their offices and failed to manage. It’s not fun and that is stating the problem mildly.
      Last, the inability to make a contribution for whatever reason can lead to depression, loss of self-worth and eventually be soul crushing. It’s a basic human need like food and water to make a contribution and to be a part of something bigger.

  2. MuseumChick*

    Sun Tzu’s “The Art of War” comes to mind here: “If words of command are not clear and distinct, if orders are not thoroughly understood, then the general is to blame. But, if orders are clear and the soldiers nevertheless disobey, then it is the fault of their officers.”

    Make sure your expectations are 1000% clear. I love having things in writing to reference so for me, I really appreciate when a manager sends out an email with very specific instructions on how we are handling something.

    Once you know you have been clear, you can start addressing the individuals who are not following your “clear and distinct” commands.

    1. Mike C. (╯°□°)╯︵ ┻━┻*

      Yes, this. The reason to hold management responsible is because they have the power and autonomy to actually do something about what’s going on.

  3. Amber Rose*

    Yeah, it sounds like you’re just cleaning up the mess without actually asking that they avoid making the mess in the first place. You’re being too passive. You need to lay out blatant, direct ground rules and something like a three step disciplinary process. Then you need to stop cleaning up. Instead of fixing the problems, tell them what the problems are then send them off to fix on their own.

    You’re used to teams who implicitly understand the rules. This team does not. You don’t need to micromanage, but you do need to be a little more controlling of the workflow. They don’t know how to follow your lead right now, so don’t lead. Push from the back. Watch where they go and course correct as needed. And there needs to be consequences. If you aren’t telling them that these problems are putting their positions in jeopardy or enforcing any rules, you’re doing them and yourself a disservice.

    2. LBK*

      I wonder how much of this is the OP not just fearing the appearance of micromanaging from her own experience but fearing running afoul of the culture of the company – I’m very hesitant to believe that a company that thinks a “pseudo-flat structure” is a great idea is going to love someone acting more authoritatively (although if it’s pseudo-flat, I guess there’s no one with the authority to reprimand the OP for being stricter!).

      1. zora*

        Yeah, this is my worry. A lot of the flat organizations I’ve heard about don’t really want someone telling other people to stop or start projects directly. It might be a culture fit issue, and the LW might be the one that doesn’t fit in this organization.

        I am guessing, though, I wish there was more information about the people “above” the LW and other parts of the organization and how they feel about this department’s work.

        1. Steve*

          Yes, the rest of the org is somewhat missing in the letter. It really is possible that it’s OP that needs to find a different opportunity and not her or his direct reports. That said, it doesn’t invalidate Alison’s advice. I would just add a second prong to also consider if the organization is right for you.

    3. Amber Rose*

      It’s pretty interesting. And it seems to be a sort of overall managing trend where people are given teams, and they go sort of He-Man I HAVE THE POWER then get frustrated when the power is not creating a hive mind. Which isn’t to say these are terrible managers or anything, it’s just that 9 times out of 10 communication is the issue.

    4. Junior Dev*

      They basically represent the whole of my tech career. Jobs 1 and 2 were the work-hard-party-hard frat house described in the previous letter. Current job is this one–but disorganized, people resistant to creating any formal process or doing things consistently.

      I’m definitely reaching the burnout phase with this one.

  5. Cassandra*

    I run into this a lot in higher education. Telling them “hey, project management! it’s a thing!” doesn’t always help as much as I wish it did — they need to see the WHY of the thing.

    I assign my graduate students Jo Freeman’s classic “Tyranny of Structurelessness,” but it’s rough going for a lot of the undergrads. For them, I have started assigning (and asking them to reflect briefly on) Kate Heddleston’s more accessible “The Null Process” from 2015: https://kateheddleston.com/blog/the-null-process So far, it’s working. It might help you spark an epiphany among your reports as well.

    (I just finished reading their reflections in the current course run, as it happens. Wow, some of their other instructors are giving them HORRENDOUS advice — or null advice, just as bad if not worse — on how to work in a team. Small wonder so many are bad at it when they graduate. I feel bad about this and wish I could fix it in more than my little corner of the university universe.)

    1. Matilda Jefferies*

      You might also look up the “situational leadership model” if you’re not familiar with it already. It talks about the difference between supportive and directive leadership behaviour, as it applies to the team’s understanding and competence of the task. It sounds to me like you are trying to work in the “supportive” quadrant (low levels of direction, high levels of support), whereas your employees need to be more in the “coaching” quadrant, where they need more direction along with those high levels of support.

      1. Cassandra*

        Thank you! I will definitely do that. Organizational behavior is not my strong suit.

      2. Dr. Speakeasy*

        Second the situational leadership recommendation (I teach it in COMM 101 and Small Group). Sometimes just getting people to think “oh! I have to adjust for context?” is helpful. Even going back to the old Tuckman Forming-Storming-Norming-Performing model is useful. Groups (especially student groups b/c of their limited experience and time frame to get the project done) sometimes interpret that Storming phase as “Everything is awful and we’ll never work together” when it’s just a normal part of group development. A heads-up that you’re going to have conflict can make the actual conflict feel more manageable.

        1. Cassandra*

          Oh, goodness yes. I learned this the hard way as a new instructor.

          Any project-management structure at all cuts way down on the mid-semester chaos, freakouts, and adjudication calls, fortunately.

    2. Hermione*

      Ooh thanks! I hadn’t read those, though I have read Gawande’s book (referenced by Kate Heddleston in that piece above). I don’t want to derail, but if you (or others) are inclined, I’d love more reading recs on this (or similar) topic(s), maybe during one of the open threads this weekend?

    3. Dankar*

      Do you mind sharing some of the bad advice they’re receiving? I used to teach some Comp 101 and it always seemed like that was the place to start building basic team skills (like understanding group dynamics and process- vs. product-driven methods) in addition to the usual writing/reading/comprehension work. I always like to know what others think undergrads should be steered away from!

      1. Cassandra*

        Not at all. Among the reflections:

        – An instructor just handwaving and saying vaguely “it’s teamwork; work it out”
        – An instructor telling students to pick a group leader, who would be responsible for “harassing” (the student quoting the instructor, and I believe the student!) other group members into compliance
        – An instructor waving off a student report of poor behavior from other team members, because (again, paraphrasing the student paraphrasing the instructor) “in the workplace you’ll be judged by output, not who did what”

        Pretty awful stuff.

        The Leading Virtually website (avoiding URL so as not to task Alison with moderating it) has a fairly low-impact charter substitute called a “Team Compact” that I use a lot in the classroom. I like it better for classroom use than standard PM charters because it is explicit about individual team members’ goals for the project, and everyone’s communication expectations. It is often safe to take those for granted in a workplace, but not in a class context where team members don’t know one another or have shared context.

        1. mirinotginger*

          As a recent student, I can confirm the last bullet absolutely happens. “In the real world you have to get the project done. They won’t care that somebody didn’t do their part, just that the project didn’t get done”. Which, while true, skips all the parts where you would escalate to your manager, their manager, etc and get other help or resources or whatever. Students constantly get put on teams because “teamwork! real world! yay!” but no actual training or advice on how to work well in teams.

          1. Government Worker*

            As a fairly recent grad student, I agree. No one pays much attention to the fact that the authority, incentives, and consequences are all arranged totally different for a student group project than a team project in a work environment. I got lucky that many of my student project groups were fairly functional, but they can go wrong pretty easily.

          2. Kate 2*

            YES! As another recent student, the lack of sick days “No excuses!” is another thing that is totally unlike the real world. Plus the 60 hour weeks the administration told us at the highest level were expected from us, all school year long. In the working world you wouldn’t do that, and if you were doing it, at a tech startup or a financial firm or something you would be paid mega bucks. At my school, and at others I have seen, students are told they are going to be saddled with an overwhelming workload, and the whole point is to see how they produce under pressure.

            1. JustaTech*

              Yes! I had a group project in grad school (where we were all working full time) where one of my teammates got very, very sick. Like, bedrest sick. And the professors were all “what do you want us to do about this person’s grade?” Uh, they’d contributed the whole semester, and they weren’t slacking, they were sick!
              As a group we said “in a work situation we would just redistribute the work and get it done, so that’s what we are going to do here. [Student] has contributed a lot and we as a group don’t want their grade reduced over something they can’t control.”

              The whole thing was bizarre.

          3. Julia*

            At my last job, I had a co-worker who actively sabotaged me (gave me wrong details, withheld information from me, answered my phone when I was away and telling the caller to stop calling!) – she was also a general slacker and could be pretty nasty to people she considered beneath her.

            When I tried to talk to our boss about the problem, he told me – I kid you not:
            “You’re not a student anymore, you need to figure out your personal (!) problems on your own.”

            Then when I quit, he was all “but why????”

          4. neverjaunty*

            Right. “Group projects” are the more complicated and annoying version of “I don’t really feel like doing teaching work so we’re going to see a filmstrip”.

  6. deesse877*

    The situation as described suggests to me that these employees believe they will be *rewarded* for starting new projects all the time. Younger people sometimes get that idea from the sorts of one-off, look-at-me resume-building activities that go into (a) college applications, especially for upper-tier institutions, and (b) college activities, like professional clubs, Greek-sponsored charities, and independent study, that have short timeframes and are relatively insulated from real-world resource constraints.

    It’s annoying AF, but it also means that such people enter adult life not knowing the difference between being validated themselves, and building something independent of themselves. OP may find that these folks get *hurt* or feel rejected when they get firmer feedback, simply because they didn’t know what was actually going on.

    1. The OG Anonsie*

      This is a good point. I can’t tell if the LW means “kids” in that they’re younger and greener than her or if they’re objectively young and green, but constantly starting up projects like this does give the scent of people trying really hard to look like go-getters who are achieving something.

      1. Dulf*

        Which, given that it’s a start-up, may be something that they’ve seen rewarded elsewhere. If upper management consists of the loudest, or the most creative, people, and not people with good work habits, then it makes sense that they’d be churning out bad ideas to see what sticks.

        1. Serial Entrepreneur*

          “Churning out ideas to see what sticks” is something of a mantra at startups, thanks to Steve Blank’s book 12 STEPS TO THE EPIPHANY and Eric Ries’ THE LEAN STARTUP. The idea is that startups need to be continually making hypotheses, testing them, and refining the hypotheses based on the results.

          For a startup, this tends to be much more important than “good work habits,” and legitimately so, although that’s not to say you can’t have both.

          Startups are always going to have a lot of bottom-up projects, and the same is true of intrapreneurship at big companies. Remember that 3M’s most successful product, the Post-It, was started by an engineer doing independent work?

          The problem here is that the manager does not know anything about these bottom-up projects. And that’s the fault of the holacracy culture. There are a lot of pros and cons to holacracy; I’m personally skeptical, but that’s neither here nor there. The point is that a “pseudo-holacracy” is the worst of both worlds. The manager has no authority to stop or alter the bottom-up projects, but is accountable for their outcome. So that’s the first thing that needs to change. Either you go to a full holacracy and learn to love it, or you abandon holacracy.

          1. Artemesia*

            Holacracy where critical functions have no home and are just supposed to magically get done, and where there is constant duplication of processes work just as well in business as in group houses where ‘everyone is supposed to keep the kitchen and bathroom clean’ with no system to make sure it happens.

      2. Meg Murry*

        I think this point is important.

        OP, rather than just telling them not to dive into projects without talking to you, are you discussing with them what they SHOULD be spending their time on?

        Is part of the issue that they don’t have enough we’ll developed projects to work on, and therefore they are diving in and “taking initiative” by creating their own projects? Or are they neglecting their already assigned projects in order to work on these pet projects?

        Could you give them more explicit projects, and detailed time frames on how to structure their week? As in: 50% of the week on Step 3 of Project A, 30% of the week of Step 4 of Project B, 10% of the week on housekeeping tasks and professional development and then 10% of their time on pet projects, which they have to bring to you to work out a project plan after no more than X hours of exploratory work?

        I would look at it as “structured mentoring on project management” and not so much “micromanagement”.

        1. Not So NewReader*

          Really. No means No, OP.
          The times I have seen this happen, the new boss said, “All projects MUST be approved by me before you can start. Failure to do so will mean automatic removal from the project.” This is absolutely KEY.
          And say it over and over. Either give people assigned projects with check in points or have them regularly review what they are working on right now.

          I have a lot of rope where I work. But there are times where the boss needs X and I have to jump on it because the need is immediate. Sometimes I will tell the boss I have Y idea and she will raise the importance of my own idea. “OH, you know that is a REALLY good idea! I think you ought to start that as soon as you can.” We go back and forth coming up with ideas on what I should target next.

          Do they have goals/deadlines? Project A needs to be done this afternoon. Project B needs to be done by Thursday. You can start Project C on Friday if nothing else comes up.

          Your secondary problem is that work is shoddy. So you use the checks to beef up shoddy work also. Sue is working on A, or supposed to be working on A. At the check in your ask her to show you her progress. Then you will know if she has been working on A and you will have the chance to make some points for her to improve quality.

          You may benefit from using a white board to make a chart in your office to show who is assigned to what.

          1. Gumption is not a dirty word*

            “All projects MUST be approved by me before you can start. Failure to do so will mean automatic removal from the project.”

            I think this is extreme. You don’t want to discourage people from taking the initiative. And sometimes in technical areas, a non-technical manager may not understand the need for the project.

    2. Falling Diphthong*

      This sounds exactly like the sort of thing some universities were doing with merit badges–the “Showed Initiative” badge and the “Worked in a Team” badge and so on.

      And if the employees are young, it could be a case of inadequate managing so that the abstract advice they’ve been given (“Start projects!” “Show initiative!”) gets channeled into “learn all the complicated things that go into a project so when I’m more experienced and suggest a project, people listen because it’s not going to be some pie-in-the-sky idea with no workable details.”

  7. Alex the Alchemist*

    As always, I thoroughly enjoy the NYM stock photo chosen for the article (as well as the wonderful advice itself, of course)

  8. Sara without an H*

    What Alison said, cubed and squared. Every failure I’ve ever had as a manager has been due to not being clear and explicit.

  9. Princess Carolyn*

    This is a fascinating question, and I really like Alison’s answer. I suspect OP’s background in more structured environments has led her to (reasonably) assume certain things can go unsaid, or that conscientious people will connect the dots. OP’s new environment doesn’t sound like a place that fosters that kind of “common sense” (which is really just a shared understanding). Being more explicit about expectations and trends is the first step.

    Of course, I’m someone who needs explicit, clear directions and goals to thrive, so that could just be my bias. It’s still possible that these people are incompetent, at least in the ways that count for these specific positions.

    1. Cobol*

      This! I’m experiencing the same thing as OP and it’s maddening, BUT I’m getting the sense that OP believes her employees should already know things because OP learned them at a young age at her buttoned-down Fortune 500 jobs.

      You’ll be more successful in getting things to change if you start from their experience, not yours.

  10. Dulf*

    I’m curious whether LW’s employees are getting a message from somewhere else (higher-up, the conferences they attend, etc.) that working on and advocating for their own projects is something that they need to do, since this happened independently multiple times and the ideas weren’t that good. They might not be over-eager so much as picking up cues about the company culture as a whole.

  11. A Person*

    I wonder if part of the problem is the company culture overall. Will actively requiring sign off on all projects be see as way more management than anyone else does? This might tie into the fear of looking like a “micromanager”. At that point, though, the LW may either have to risk overstepping or consider whether s/he wants to work at a company like that.

    1. Miss Brittany*

      This is where I was going, too. It seems like the square peg is actually the LW, through no fault of his/her own. It sounds like the company culture encourages this kind of behavior, and the LW is not the best fit.

      1. Gadfly*

        Although, as was discussed in today’s other manager letter in regards to diversity, LW might not be a match for this but still be the necessary compliment needed to make it actually be functional.

        Startup only works to a point. After that you have to maintain and sustain and produce.

  12. Junior Dev*

    How do all my coworkers have dopplegangers at this startup, is what I’m wondering.

  13. Menacia*

    Seems like the culture OP described “projects are designed pretty ad hoc across the whole organization” fits the staff but not the manager? This lack of structure would drive me nuts but I guess some places thrive on it. Would be interesting to hear, when staff are asked, why they aren’t following all the processes put in place by OP, perhaps too many constraints? Perhaps making changes in smaller doses might work better?

    1. Nicotene*

      I wondered about that line too. If I were the OP, I’d also try to look seriously at the wider context: 1. Are there negative consequences for me personally when my team performs this way? and 2. Is the broader culture encouraging this behavior (and will my enhanced oversight be out of step with other managers?). I did wonder if OP was having a culture fit issue herself, within the org – but assuming she’s already considered these questions, I think Alison’s advice is right on.

    2. Artemesia*

      Maybe they thrive on it — or maybe it is a major cause of the usual failure of startups — lack of management.

    3. LBK*

      It doesn’t really seem like it fits the staff, though, if the lack of structure is leading to projects being half-baked like this.

  14. Sue Wilson*

    The way you wrote this, it sounds as if you don’t believe you have the authority to stop them or you don’t believe your company culture would allow it. Like it feels like you believe the most authoritative you can get is encouragement. Alison’s advice is great, but I would also check in with your manager to make sure you’re going to get back-up yourself. And if you’re company does expect you to manage, I would take a good long look at how you feel about having managerial power in this environment.

    And if not, then I would move onto another job, because being a manager who can’t manage is a frustrating and useless endeavor.

  15. DecorativeCacti*

    Do you have any of this in writing, OP? I am in a very structured environment and we have SOPs about starting projects and required forms. You may not need to go that far, but would a simple checklist help? You can create something that they can use before they bring projects to you (or start them) that can help make sure they’ve thought through all of the layers. Something that says, “I have evaluated this project and understand how it will impact X, Y, and Z.”

  16. Lora*

    Have managed many recent graduates. Here is what works for me:

    1. You will be working on Project A. Here is the question we are trying to answer / thing we are trying to accomplish. Here are the ways it has been approached successfully in the past, and you can use it as a template to start from. Please write me an outline of how you would structure/design this project.
    2. I revise the outline, we go back and forth usually multiple times. It’s a lot of editing.
    3. OK, your outline is good, now can you fill this in with lots of detail and write a protocol with cost benefit analysis and scale calculations and (other detail-y stuff)? And include the spec sheets. Then send that to me.
    4. More revisions.
    5. Can you generate an interim report? Here is an example of an interim report we like. You can use it as a template.
    6. More revisions.
    7. Great, now I will walk you through the analysis with our software. Here is a tutorial, start with working your way through the tutorial and then I will show you how to do the actual data crunching.
    8. We’re at a good place. Can you write a final report now?
    9. More revisions and more revisions after that.
    10. Wow, this came out great! Can you put together a presentation of your data and you can present it to the Big Boss?

    Etc etc. I always make sure there’s reference material so they know what the expectation is and walk them through a few things before they are on their own to be creative.

    1. StellaMaris*

      This is the kind of step-by-step guidance I was thinking of – thank you for this!

      1. Lora*

        If they are fresh out of college, start with the assumption that their writing skills will be mediocre at best, more likely not appropriate (tending towards too flowery and verbose) for business. So you have to teach them to write properly for business and that means a lot of editing at first. By their third report / project they should have the hang of a business voice. Some will pleasantly surprise you, but set your expectation low.

        Even if they had loads of prior experience, you’d still have to train them in the style and format that your particular organization prefers for different types of documents. Have worked with many experienced technical writers who couldn’t write a training manual or regulatory submission to save their lives.

        Also, reckon it will take about 2.5 X the amount of time it will take someone who has experience to do the project. For whatever reason, 2.5 seems to be the magic multiplier for training schedules.

      2. Lora*

        Also, for controlling the rogue projects, maybe have a once-a-week brainstorming session in which each person talks about their idea du jour and other folks can critique or add to it or whatever? That way their horrible ideas get some feedback and they can develop a better notion of how to troubleshoot an idea before they act on it, and they can start to see you and others as resources for help rather than keeping everything super secret.

    2. Little Miss Cranky Pants*

      OMG, this idea of Actual Training and Feedback is terrific, and I wish more companies did this explicitly. So much more productive than being told, “read the Wiki for the department” and then “training” is, er, considered done. Done by the trainer, that is.

  17. Snark*

    My thinking is that, given that these workers are young and just out of college, and working in a startup where entrepeneurship and innovation are the bread and butter, they’re under the impression they need to show gumption and moxie by being as innovative as they possibly can. And they’re doing that in kind of a hamfisted and puppyish way, by trying to innovate and create on their own, and as a startup there’s likely no process or standards developed for evaluating and advancing projects.

    Startups can be super-creative and productive and innovative, but there’s a reason the rest of the business world has SOPs for this kind of thing, OP, and there’s a reason bosses typically are the ones to select, prioritize, and critique proposals from their underlings. You can be a boss, not just a playground monitor.

  18. StellaMaris*

    I definitely read it as “taking initiative” – which, in a start-up, makes sense. What I’m really confused about is that it doesn’t seem OP (or anyone?) has to be pitched to and/or sign off on projects before people start working on them… that’s bound to cause wasted time and effort!

    Teaching project management and effective project planning would definitely help. Otherwise you end up with Underpants Gnomes-type projects where there’s an idea and a desired outcome but no actual plan.

    Phase 1: Steal Underpants.
    Phase 2: ???
    Phase 3: Profit

  19. Junior Dev*

    On a more serious note: how do you deal with such an environment when you are not the boss, but the most junior person on the team? I try real hard not to care too much about the details of what my coworkers are doing but it’s tough when I am trying to debug an error that happened because someone copy/pasted code from the internet without knowing what it does.

    1. Not So NewReader*

      I would collect up some facts then go to the boss with something like this:

      “Boss, I have been watching this for a while. I am see that at least three times a week (sometimes more) I am debugging errors for x hours. These particular errors are happening because someone pasted code from the net without knowing what it does. Since this happens so often, how would you like me to handle it going forward?”

  20. Poster Child*

    Worrying about micromanaging isn’t the right way to think about it. You need different management styles for different situations. This situation appears to require a more directive approach which may or may not come naturally for you. That doesn’t mean you have to give direction on every detail like dictating an email they send but it does mean you need to give more specific direction at more points in the process and have more frequent check ins. Learning to flex your management style is a huge part of becoming a more effective manager.

    1. Artemesia*

      Precisely. What are you doing, where is the project in the process, what will be completed by Friday? is not micromanaging — it is managing.

    2. Princess Consuela Banana Hammock*

      Yes! Also maybe checklists. If there are key components that need to be in a proposal, or key questions that have to be answered before a project may launch, I find it helpful to have a checklist to make sure I didn’t miss anything. There are probably tools that, when paired with a more directive management style, can provide structure without feeling micro-manage-y or stifling.

    3. Not So NewReader*

      A person who directs traffic is not micromanaging that traffic. People drive the cars they want, they carry as many/few passengers as they wish, with in a range because of setting they drive at different speeds. Additionally, they drive at different times of the day and different days of the week. I could go on.

      Micromanagement comes with an attitude, OP. Usually a vengeful attitude that has roots in fear, animosity, negative thinking and lack of self-confidence. Micromanagement creates negative outcomes as people are unhappy or angry, people do sloppy work ON PURPOSE and morale tanks.

      Micromanagement boss: You may inhale, you may exhale. HEY! I did not give you permission to inhale again, how dare you, you stupid so-and-so.

      Confident Boss: Here are projects a, b and c. Please work on these. You need to know special information x, y and z. Since project a is new to you, I would like you to check in with me when you reach the half way point at step number 4. But you are good to go with projects b and c so just bring them to me when you are done.

  21. Artemesia*

    What shouts in this situation and isn’t addressed is what is upstream from the OP. I have just watched a very promising startup that was among the first out of the gate for a new market crash and burn because they implemented management by no one being in charge. There are lots of names for this nonsense ‘flat hierarchy’, ‘wholeocracy’, ‘collaborative’ etc etc but it boils down to no one managing and no one being accountable. Without support of the higher ups to both manage and if necessary fire this team, this team is going nowhere and if it reflects the whole company, the company is going nowhere.

    If individual team members are starting projects without approval where is the manager? Sounds like time for some more ‘management by walking around’ and firm implementation of Alison’s suggestions. If this doesn’t turn it around then the OP needs to sit down with his or her own management to explore options for firing and hiring or else needs to be seriously looking for a new position. I’d be getting my resume polished.

    1. zora*

      Exactly, this was where my mind went, too. I really want to know more about what is happening ‘above’ the OP, and what the decision-makers of the company think about this department.

    2. Not So NewReader*

      Yes, management by walking around. And this can be done in a friendly conversational manner.

      “Hi Bob, Good morning…. yes, yes. I am doing my morning walk. How’s it going for you here? Oh good. So how is project A doing where are you at on that? Oh I see looks great. I love how you did parts 2, 3 and 4. That is really sharp work right there. Bob, it looks like you may finish soon and we need to start project M next, please. Oh, okay, I will tell Kathy to give you the other half of the files so you can have the whole project. And we have something else that we need Kathy to help with.”

      Use the word “we” as often as possible. It’s a soft way of reminding everyone they are part of a group and there is a group effort going on. If you use the word “I” too much it sounds like it’s all about you, which as you know, that is not true.

  22. kindnessisitsownreward*

    A lot of people have the mistaken impression that structure stifles creativity, and that might be why the LW is having such a hard time getting her team to buy into what she is trying to accomplish. In fact, it may very well be that none of them have ever actually worked in the type of environment she is describing. I know I didn’t–a lot of organizations, especially small ones, don’t have much structure. I agree with AAM; the LW needs to be much more direct, much more “in their business” to effect any change.

  23. Chatterby*

    Surely not ALL of the projects are poop?

    Come up with a set template/style guide for submitting a project for approval.
    I suggest including rules that the proposal for a project must have a calendar timeline with measurable goals, include a list of required resources and/or teammates, an estimate of how many hours it will take, and a list of possible road blocks with plans on how to deal with them.
    Set up the template, make it and an example of a good proposal available, and then announce that all projects must be approved by you. If projects are not approved by you first, they are not a viable way to spend company time. Give the team an easy way to submit or talk about their plan with you, such as regular one-on-ones, and be encouraging but realistic in your feedback.
    Once a project is approved, demand transparency and regular check-ins on progress. Give warnings if their project goes off-course that it may be canceled if X happens, or they do not achieve Y.
    It’s going to be painful at first, but it will get better.

    1. Chatterby*

      If her team still doesn’t comply and starts going underground, the LW has bigger problems: i.e. she may not be a good culture fit for the team or this office, her team does not trust or respect her or her ability to manage them, or they’ve caught on to her exasperated opinion of them and decided she’s the enemy.

  24. AnonAcademic*

    I work in an academic environment that has a lot of parallels to a start up. I have at any one time several “shadow projects” that my boss doesn’t know about, or doesn’t know how much time I’m spending on them. The ones he knows about, he thinks are a waste of time. What it comes down to in my case is that left to his own devices he’d pile more and more work on me that benefits his career but not me or our organization necessarily. To progress in my field, you need to distinguish yourself as an independent contributor, not just “so and so’s mentee.” Most mentors respect this and allow time for professional development (teaching, learning new skills, building your own collaborations) but since he doesn’t, we all do it semi-secretly (in at least one case my grand-mentor suggested a shadow project for me and offered political cover when my boss finds out).

    The point is that sometimes pressure from dysfunctional faux-meritocracy environments will drive people to try to “make a name for themselves” for reasons and in ways that may be valid or misguided. It’s worth finding out what is motivating the team to act in this way – do they think they’ll be rewarded more for taking risks than working in a structured manner? Do they realize that it is working against them professionally (make sure it actually is)? Are the side projects actually favors they are doing for people who’ve pulled rank on them?

    1. Grapey*

      I disagree with this. Trello or JIRA or any other stuff tracking app is good once you have a good methodology in place to deal with project scope and accountability, etc.

      Otherwise you’ll still just throw stuff at a board to see what sticks, but now it comes with more notifications that clutter your inbox. I was tasked with designing a process workflow with approvals(!) but management never actually bothered to approve tickets, and staff never bothered waiting for approval.

  26. LBK*

    I can’t remember if the photos on these articles are chosen by you or your editor but whoever chose this one nailed it. They just look so gung ho about their terrible ideas.

      1. Safely Retired*

        I thought the image was in conflict with the letter. Kids? All I see is old folks.

        1. Not So NewReader*

          It’s about the attitude. You’re right that the age group is not the same. But look at the expression on each person’s face. They are happier than clams. Except for one person. I assumed that the one person who did not have her fist in the air was the boss.

    2. Rebecca in Dallas*

      I was already laughing at the stock photo, then when I got to OP’s “HOW SWAY?!” I lost it!

      Sorry, OP, it sounds very frustrating! Alison has spot-on advice as always. Good luck!

      1. AW*

        I laughed too. It’s nice to get new slang that isn’t immediately used incorrectly and driven into the ground.

  27. animaniactoo*

    OP, one thing that I would do in reference to all of this, is to reference the high statistic of failed projects, and talk about the need for everybody to pull back a step and think about project structure.

    Therefore, until there is a higher success rate of individual projects, you’re going to institute a policy that projects have to be brought to you, fleshed out, and approved before proceeding to work on them.

    Possibly it could work to call a once-a-week brainstorming session.

    One thing you want to do is not to tell someone “No, that clearly won’t work.” but rather challenge them to solve the issue that you see. If they can solve it they can go forward. If they can’t solve it – they’re stuck at the “solve this portion” stage until further notice.

    Because what you want to do is develop them to think through these things, these snags for themselves. So you raise it as “Do you think it will be a problem to X?” for some stuff, and for others, you “assume” they have the knowledge and say “Okay, what are you thinking about for Y variable which will create Z issue?” –

    Your goal is to be a constructive sounding board. As they develop, they’ll gain more experience in seeing those issues for themselves. In the meantime, it’s likely they’ll drop a lot of projects in the early stages in pursuit of others. That’s okay. Let em. You want to encourage the ability to at least explore the idea, rather than stamping it out right away. And it will feel much more their own choice when they abandon an idea rather than you being the roadblock that kept it from happening.

  28. Jaybeetee*

    I haven’t read all the comments, and admittedly don’t know much about start-ups (I’m aware more independent work is expected with them, but not the degree), but OP, does your team have enough to do? Half-baked impossible projects reminds me of a place I worked where the staff was both very young/inexperienced, and had almost nothing to do most of the day so were trying like crazy to “contribute” somehow.

  29. Soupspoon McGee*

    OP, it’s so important to make sure you have a good read on company culture. The semi-flat structure and fast-and-loose hiring lead me to think the startup is really not supportive of more structure or grew too fast, but might be ready for the kind of structure and management you’d like to see. You may have been told one thing, but you’ll see another.

    My experience is by no means universal, but I was hired to run a department and bring more structure to college-wide processes, and ultimately bring in more funding. The problem is the overall culture was not supportive, and things that were normal or even casual at other places were perceived as heavy-handed and mean–things like bringing projects to me early in the process and communicating with affected departments before making promises and spending money. I bent over backwards to be clear about expectations and offer help at any step of the way, but for the most part, not much changed. It came down to me having responsibility but no authority; the people who hired me retired, and their successors didn’t understand the problems that arose when the cowboys did their own things. Ultimately, I left, and my job was parsed out; I’ve heard that there have been several disasters since then.

  30. Trout 'Waver*

    I’m normally disinclined to micromanage. But when you have very enthusiastic yet unexperienced people without clear direction, that’s the time to micromanage. Explain exactly what you want and exactly how you want it. With good people, you can usually transition from micromanaging into more collaborative or delegating leadership techniques quickly.

  31. SeptemberGrrl*

    They’re good kids is kinda sticking out for me. OP says she doesn’t want to be their mom but then uses this language to describe them, and it feels off to me. FWIW.

    I agree with Alison’s advice. You need to make it clear that running a project by you is an absolute requirement and stick to it. Come up with a basic outline of the points you’ll want to review with them for each project and stick with it. When things go awry and the process isn’t followed, address it clearly and quickly. There’s no reason not to approach as you would if their performance was lacking in other areas of their job performance.

    1. A Different Name for This*

      it feels off to me

      It’s certainly contradictory. It’s too familiar and maybe even patronizing.

      And we know from other letters here that employees don’t enjoy the “work mom” dynamic from the other side either.

  32. designbot*

    I just don’t understand, if they’re kicking off projects without your approval, what is it you think they’re working on? And is that work not getting done?
    The way we’d handle this in my office is that if a project hasn’t gone through the proper approvals, it doesn’t appear in the staffing plan, and if it doesn’t appear in the staffing plan you’ll be staffed 100% on other projects and not have time for your unapproved poorly planned thing. If they’re not staffed on enough approved projects to take up their time, then that’s just asking for random unapproved stuff to happen because they have too much downtime.

    1. always in email jail*

      In my experience, staff who are constantly coming up with these “great initiatives” are trying to avoid doing the work they’re actually paid to do, aka the boring stuff. I had to make it clear to my staff that they don’t take on “extra projects” until they demonstrate they can complete the core responsibilities of their job.

  33. Safely Retired*

    The instructions to not start off on their own being ignored I suspect can be attributed to the corporate culture. The team may have been recruited with that promise! As much as the chaos of what they are working on is driving you nuts, I think you should address a different problem first.

    To me the bigger problem, the one I would address, is the quality of the work. Rather than telling the team not to do anything outside their assignments, I would tend to (try to) concentrate on getting them to do good work. Few programmers begin with the knack of knowing how to approach a problem. When I got my CS degree (40+ years ago) we had been taught to program, but not a thing about design, and from what my granddaughter describes it has only gotten worse. If all you try to do is squash everything they start they are unlikely to come to you and talk over how they are approaching things. Tell them you expect them to run things past you and then give constructive criticism without saying Stop. If (when) they don’t come to you, it is time for MBWA, Managing By Wandering Around. It is a classic approach in a casual environment such as yours. Drop in, shoot the breeze, show interest in what they are doing, and try not to dump on them as you point out problems and suggest solutions. “Yeah, I tried that approach once but I ran into… it wasn’t until I tried this other approach that I got around that.”

    I was never a manager – that would have been a disaster – but I did a LOT of MBWA, dropping in and helping out. One boss called me the “glue” that held a huge (5 years!) project together. To a large degree I built my career around it, and it worked until a boss a few levels up couldn’t stand to see me not fit neatly into an org chart. Your org sounds like it needs someone like that.

  34. always in email jail*

    I had a similar issue with my previous team, and you’ve articulated it much better than I ever could!
    They would come up with “ideas” and “initiatives”, and tell partners about the great “upcoming initiative” (!!!) before running them by me, and when I caught wind I’d realize how half-baked they were. A lot of “We’re going to undertake a huge initiative to engage stakeholders to educate the community on teapot safety!” “OK, which stakeholders are you thinking specifically?” “Our partners!” “yes, which ones” “from the organizations!” …. “Who is the target audience?” “the community!” “Ok, so the entire community? How are you going to reach them?” “Through education provided by our stakeholders!” “OK but physically where will you connect with them?” “Through outreach!” RAAAAGE.

    Anyway, as Alison suggested, I had to sit them down and tell them exactly what I needed from them when they wanted to implement a project. For our purposes, the list was something like this:
    -Overview, including the goal/objectives of the project/initiative
    -Evidence of need for this initiative (what gap is being addressed, and what evidence supports that gap?)
    -Partners you hope to engage (specific organizations, with specific points of contact from those organizations whenever possible)
    -an outline of the information you hope to present in the initiative (they were usually vague “outreach” or “education” or “training” initiatives with no proposed content)
    -Resource needs
    -Estimated timeline, with concrete deliverables

    They did feel “micromanaged” and ultimately found other positions. And you know what? It worked out. Because now I have staff who come to me with those details when asking for my support for a big project without being told. And the new staff are younger than my previous staff, so it’s not an age/experience thing either.

  35. MW*

    Really curious why the OP hates Slack. As a techy, I hate that I have to use abysmal Microsoft Slack substitutes in all the corporate jobs I’ve had. I abhor Lync, Skype for Business, Teams, etc. The only thing I might prefer to Slack is Discord, but I think that’d be a hard sell in most offices.

  36. Lady Ariel Ponyweather*

    No advice, but I think it’s great you’re trying to improve and be a more effective manager. Good luck, I hope everything works out.

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