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  • Writer's pictureJason Costa

Turning around a Team

Updated: Feb 15

I’ve been asked twice to take over an ailing team and turn the initiative around. 

The first time I was still early in my career, and failed spectacularly. At the time, the team I was working with was understaffed and a company afterthought with very little support. Engineering was checked out, and ultimately I failed to rally the team. After just a few quarters (though it seemed like millenia), the situation felt hopeless and I punched a ticket to switch to a new team that was better staffed and supported. 

The second time around, I had far more experience and had learned from my first pass.

When the second situation sprung up, the group had just lost key leadership positions across the board - critical product, engineering, and design leaders had all left the team within weeks of one another for various reasons. I was asked by the head of product to simply step in and stabilize morale on the team. Just stemming further attrition would be considered a win, I was told. 

If you’ve ever taken over a team in crisis before, you know it’s not easy. It’s a sustained uphill battle with a long time horizon. There is literally no quick fix. But here are some things you can start to do in your first couple of quarters at the helm to begin shifting the tide. 

The Right Partners

You won’t be able to do this by yourself. You must have the right partners on the roster with you. That means incredible leaders on engineering, design, and data. If you don’t have folks that you actively want to be in the trenches with, who can solve problems and manage the team’s momentum, the team isn’t going to win. 

The first thing I did was start seeking out a strong engineering director. I looked high and low: internal candidates, potential transfers from other parts of the company, and external candidates. I was clear in managing the situation with all pertinent stakeholders that this was the most critical hire we’d make on the team that year. It took six painful months, but we finally hired an engineering director who knew how to set & drive a new performance bar. I conducted a similar exercise with design, and there we were able to internally reallocate a phenomenal director who had the background & grit to take on the role. Lastly, we hired someone in to take over data leadership on the team. 

Make sure that these folks are eyes wide open coming in: they need to know the good, the bad, and the ugly. In total it took almost a year to get these critical pieces in place: but it paid dividends over the next several years & totally leveled up the team. Until you find those partners, you have to work with what you have and you should expect it to get messy.

Listening Tour

In parallel with finding the right partners, it’s important to immediately set out on a listening tour across the team. Sit down with folks, open up with them, create a safe space for the existing team members to share their thoughts & feelings about where things are at and how the team arrived there. Do this cross-functionally across the different disciplines too. Much information will be gleaned from this process, including who some of your key players are. 

In my case, I was able to quickly infer who was really a missionary, who was a mercenary, and who was just hanging out. Keep your missionaries close, as these are likely to become or already are your high performers. They’re most likely to stick with you as things get thicker.

Where’s the Strategy & Vision

Both of the teams I took over had something in common - they didn’t know which direction the coast was. They were both paddling aimlessly & in different directions; throwing things against the wall & hoping that a few things would stick. If folks don’t know which direction the coast is, you’re going to either row in circles or just in place as the team isn’t directionally rowing in unison. 

As a leader, you must bring a certain level of clarity that enables the team to collectively see the horizon, and then you work backwards to identify your milestones along the way that will take you to that horizon. The good news is that you don’t need to do that by yourself, nor should you do that by yourself. Get your team involved, push your cross-discipline partners and product lieutenants to help you craft the vision and the strategy. 

This has the added benefit of generating buy-in as you’re effectively pregaming and sharing ownership of the plan with the team. Folks are naturally going to be bought in from the get go as they helped to shape the path forward. That way, you’re not looking like Moses coming down off of mount high with the tablets in your hand. That approach is far more likely to backfire, and have you looking more dictatorial than a true leader.

Get the Analytics Right

When I joined the second team, the metrics were a shitshow. There were 6 different metrics being tracked, with no rationale for each nor clear laddering to the company’s goals & strategy. The first thing I did was chuck all six of them, focus on a new key metric that I knew had a high correlation coefficiency with a company level strategic metric I was ultimately trying to move. This gave the team more strategic positioning in the eyes of the executive leadership team. 

So my recommendation is to pick one metric that matters, and rally the team around that in tandem with the Strategy & Vision. This should take a great deal of analysis and debate. There should be a clean story on how the metric the team is picking ladders up into key strategic priorities for the enterprise. Your team's metric should be a leading indicator for the metric you ultimately want to move downstream: so if wearing hardhats on a construction site is the largest lever to decrease onsite injuries, you want to get more hardhats worn on the jobsite. To torture the analogy - company priority is less injuries, team priority is more hardhats.

But remember - the map is not the territory. Metrics are ultimately a reductionist approach to user value. It’s easy to lose sight of what the metric represents - a user journey you’re looking to enable that drives value for that user, but it is not a perfect representation of user value (behaviors can change, be over-optimized, etc.). If metrics are driving the team’s strategy, there’s a bigger problem (i.e. no strategy - see the "Where's the Vision & Strategy" section above). 

Raise the Bar & Set the Tone

It’s critical that the team understands that change is happening, and that what may have worked previously is no longer going to take the group to the next chapter. In the case of a turnaround, it’s often far easier to sell that story as it’s (hopefully) quite clear that things aren’t working and that change is not just desired but required. There are likely to be some folks on the team who are unaware that things aren’t working; as a leader you should worry about those folks as you begin to evaluate the roster. Make it clear that working together as a team is a prerequisite, that execution and delivery are baseline expectations, and that impact is a must. 

I recall one instance where a subteam, literally the week as I was joining the team, was doing a massive launch with a large advertising partner. The stakes were high. Literally the weekend before the launch, I’m playing with the feature and noticing that it’s totally broken. Naturally the CEO noticed this too, and (rightfully so) was quite upset. It was clear that no real QA had happened from the launch team, and when I reached out to them to discuss options on the weekend they were indignant about that. While I don’t normally expect to make weekend calls, this was a major launch with high stakes - if that sentiment isn’t shared wholly amongst the team, it’s time to evaluate the roster.

Evaluate the Roster

Once you’ve raised the bar, see who rises to the occasion on the team. Be open minded and let people surprise you. But constantly be asking yourself - do I have the right people around me to ensure this journey ends in success? 

This is an incredibly hard dance to negotiate. You’ll need to read the room and understand how much agency you have here. If someone is good, but not the right fit for your team - see if you can land them somewhere else in the organization where they’re likely to have more impact & ultimately be happier. If someone is checked out or just no longer the right fit for the company, consider whether they’ll be happier pursuing a new adventure. And if you do have to say goodbye, be sure to treat people humanely and take care of them on the way out. 

The inverse is true too - especially if it’s a turnaround situation. Keep your impact players, who are likely to be few and far between, close to you. These folks are likely to have options, both inside of the company with new teams and outside of the company in new jobs. Do what you can to ensure that they’re intrigued with the path ahead.

Always be Recruiting 

You’re always recruiting, whether you’ve got open headcount on the team or not. If you don’t have open heads, know that you’re going to see change on the team - some folks may tap out as you change the pace, others may just be ready to move on or open to other opportunities. This is true for your cross-functional teammates too. Folks move on - it’s a natural part of the process. 

That said, it’s good to have those networked connections in the backpocket so that you’re not stuck with an open backfill for too long. Having the work pile up on a team going through a transitory period can become a real anchor after a lengthy period of time.

Alignment up the chain

You also have to ensure that the culture of the company will support you. If you get into a situation where you have to say goodbye to folks, it’s important to understand if the company and your management chain will have your back. If not, you need to know that you’re likely to end up as an organ rejection. 

The second time I had to do a turnaround, the leadership team was not a fan of parting ways with people - it was a cultural faux pas at that time. That was tough. I knew that I’d be going out on a limb to turn the team over. In the most extreme cases, I could make changes. But there were some folks who clearly were anchors on the team - but had been around for a while, or were friends with certain people. In that case, you have to find new homes for folks where stakes are lower and hopefully they can contribute more effectively there. It’s not ideal, because in many of these cases you’re going to feel like you’re foisting problems on other teams. It is what it is, and sometimes that is the hand you’ve been dealt to play.

Likewise, you also need to ensure clear alignment on the strategy, vision, and the user value (as measure by your one metric that matters) that you're team is driving. Ensure that as you pitch the story, it's clear what the team is doing ladders directly into strategic company objective(s). That pitch must be crisp & crystal clear to the leadership team above you - they should be excited.

Connect with the next Layer

Don’t just converse with your direct counterparts, though of course you should be doing that most heavily. You need to connect with their lieutenants too. Giving them access to you provides a valuable feedback pipeline to you about how the team is doing & feeling, and also works the other way, giving you an avenue to communicate & reinforce key messages via proxy across the broader organization. 

As part of this, make sure that the org design of your team is configured in such a way as to bring the most out of your most effective people. Set them up for success, and design the org so that the team’s success is facilitated rather than inhibited by it. But as a warning: be thoughtful and deliberate here. Doing any kind of a reorg is expensive and taxing on people - ideally you get it right the first time and don’t have to revisit this for some time.

Pair autonomy & decision ownership with Accountability 

You have to empower the team to take on decisions, and ultimately to own the outcomes of those decisions. Part of that is making it clear which decisions you need to own as the leader, which ones you want to be consulted on, and which ones they should run point on without your involvement. 

If you want to expand autonomy and help your team feel comfortable with owning decisions - then you have to help them understand what criteria is most important to you. If they’re constantly coming to you for input on all decisions, then you haven’t made it clear what’s important to you. Furthermore, if they make the right call (i.e. they made the call with what’s most important in mind) but the outcome is bad you can’t come down on them about it else you’ll tear at their confidence to make a decision again.

In Conclusion

I could probably write a book on this process. It’s an incredibly hard road to travel, so don’t discount the risk of taking on such a project. I did my first time around, “how hard could it really be?” was my thinking going into the situation, and it really bit me hard. Know too that it will be a long process, in which you’ll need to navigate a lot of feelings & emotions; those of your colleagues and your own. 

And you might ask yourself: how will I know that the tide is turning? You’ll know. Plans will start to manifest with greater clarity, timelines will start to be met in a way that they weren’t before, and the product quality going out the door will consistently get higher. As those circumstances start to materialize, so too will the team’s confidence grow. You’ll start to feel the electricity of being on a high performing team - the contrast will be a stark one. It will feel like the team is winning. One easy test to run is to take a vacation for a week or two, and see what happens. If things don't fall apart while you're out, that's a sign that the situation is improving.

The best thing you can do over the course of this process is to think clearly, evaluate the facts, and take a “ride the wave” type of attitude in your approach. You’ll have some tough days, but know that the weather will change with enough time & effort. The highs after you’ve turned the team around and the realization that new, different opportunities lie ahead for your team is a very, very rewarding feeling.

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