Ask a Boss: I’m Managing a Team of Lovable Screw-Ups!

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Dear Boss,

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 overeagerness 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? 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.

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Ask a Boss: I’m Managing a Team of Lovable Screw-Ups!