The First Two Questions to Ask When Your Team Is Struggling

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Problems can arise as teams grow and change.

I’ve never stepped into a leadership role without it quickly becoming clear why a new leader was needed. I think it’s normal for companies to hire new leaders when there are problems that need to be addressed. So I suspect that as the congratulations die down, it’s also normal to look at the set of problems that surround you and ask, “Where do I begin?” (also normal: “What have I done?!”).  I suggest instead starting with these two questions:

  • How do I create clarity?
  • How do I create capacity?

How do I create clarity?

Every struggling team I have encountered seems to be experiencing some kind of existential crisis about “who we are” or “what is our purpose.” Often this crisis is framed as a need for defining a “vision,” but as a pragmatist (and someone who frankly hates the word “vision”), this seems beside the point. If we’re not shipping, how much does it matter what we’re not shipping? How can we possibly know what we should be doing two or five years from now if we don’t have a consistent idea of what we are doing today?

Here’s the thing about the “vision” problem: It’s a comfortable one. No one on the team feels threatened by it, because it’s largely someone else’s problem. Everyone can have an opinion about it, because it’s abstract enough that most people won’t have to do anything to shape or change it. Vision debates are the “bikeshedding” of team purpose and structure: They’re the sideshow discussions people have in order to avoid confronting more pertinent problems.

Clarity is harder because it’s more immediate, and has to be based on what’s happening today—which means you need to confront what’s actually happening today—there’s no hiding behind “lack of vision.” Are teams delivering? Are projects drifting on and on with no end in sight? Are we doing things because they are interesting or because they are valuable?

The more concrete we get, the harder it is to get everyone in agreement: A wide range of opinions can find shelter in a broad, fuzzy, statement in a way that is not possible in a narrow and clear one. Clarity involves hard conversations, hard truths, and defining one, then two, then three steps ahead. It is hard work that looks small from the outside—a “no” here, a “no” there, a refinement of this and that. It’s often stating what at least some people believed to be true, anyway, such as what isn’t going well or what the next steps include.

And yet, it’s the most effective way I’ve found to stop teams from drifting and get them to start executing.

What actions you can take in order to achieve clarity depend on the team, but typically you might:

  • Take stock of all ongoing projects, as well as the purpose and timeline for each of those projects.
  • Clearly define the scope of upcoming milestones in every current (and new) project.
  • Articulate the current priorities of the team, the purposes of those priorities, and the rationale behind making them priorities.
  • Determine timeframes that you can predict (e.g. we are focused on X through the end of Q4) and highlight parallel work that will determine what comes next.
  • Make sure project status is visible and that teams have visibility into each other’s work (e.g. stand up meetings).

How do I create capacity?

Struggling teams also commonly suffer from a sense of overload. Often this is very unevenly distributed across the team—some people are exceptionally relaxed, whereas others seem alarmingly overwhelmed.

If you view your team as a system, you’ll see where you have bottlenecks that, if cleared, would increase the overall capacity of the team.

Perhaps you have teams that are working on too many disparate things (this usually involves people working alone). How do you streamline, focus, and make progress?

Perhaps your incoming requests are out of control. How do you stop checking off requests one-by-one and take a more strategic approach instead? What kind of help do you need to do that?

Perhaps you need to realign people closer to the work they want to do.

Perhaps you need to give some people clear feedback about where they’re falling short, and if that doesn’t work, start the process of letting them go.

Usually people outside the team (leadership, marketing, etc.) are talking about dates and delivery, but you need to get the team itself estimating its timelines and embracing continuous delivery.

If you manage managers, improving them as leaders will always create capacity on your team:  Their teams will get better, and you can rely on them more and delegate more effectively. Sometimes it feels like we don’t have time to coach the people around us, but medium-term—not even long-term—we don’t have time not to.

OK, now what?

It’s likely that asking these questions has given you a whole lot of work to do. As you are human and can only do so much at once, now comes the question, “What do I do first?”

Answering this question is a balance between impact and time. The highest impact things you can do will likely take longer, but there are usually several relatively impactful things that won’t take too much time. If you’re new, you’ll also have to balance building trust and demonstrating impact. For example, clearly communicating big-picture information about what is going on to the team is a worthwhile exercise that often uncovers new information, is usually relatively quick, and creates shared understanding across the team of where projects are at.

However, these smaller time investments  will not have any impact unless we also take on some bigger ones. For example, there is nothing more corrosive to overall output than if one or more teams have a lead who is struggling or just isn’t a good fit. Addressing this kind of situation is never straightforward, and never easy—the only thing worse and harder, ultimately, is letting it continue unaddressed.

Every situation is different, so my suggestion is to write down a list of ideas for each, talk them over with your boss, a trusted peer, or a coach, and then start taking them on one or two at a time. Just remember the list isn’t static: As teams evolve, the bottlenecks change, and you’ll need to keep asking these questions, revisiting and adjusting as you go.

Cate Huston is an engineering manager at Automattic.