Can you lead a struggling team to success?

Being asked to lead a team that isn’t entirely performing invites many open-ended questions and challenges.

Hi Mathias,

I recently started leading a new team, and things are going well. Now, my boss wants me to take charge of an underperforming team. I’m not sure whether stepping into this role is the right move or if it might have negative repercussions for me. I’m unsure if this is a chance for growth or if it’s something that will wear me down. 

Thanks,

Robin

Hi Robin,

I understand your hesitation: turning around a team is a special kind of challenge. The risk of burning out is very real, as is the risk of failing to lead them to calmer waters.

That being said, your position is ripe with opportunities for experimentation and learning. Whether it’s figuring out what’s holding the team back, how you can get folks to trust themselves, each other, and the rest of the company, and get them to the point of shipping frequently, there’s plenty of room to use your existing toolbox or try out new things.

A certain type of leader thrives in these environments, bringing direction and continuity to struggling teams, departments, or entire companies. This experience will help you figure out if you fall into this category. If not, you’ll still be able to carry forward the rare opportunity you had to lead multiple teams toward betterment. 

Let’s break down how you can prepare for this challenge so that you can be sure you truly want to take it on.

What are the worst things that could happen?

Thinking about failures upfront is never a fun thing to do. But in this case, it forces you to consider what might go wrong. Not only does it mentally prime you for a potential worst-case scenario, but it also allows you to craft your plan B ahead of time so that you can pivot quickly should things not pan out as you’d hoped.

Start by making a list of anything that might go “wrong.” For instance, you may not gel with the new team on a personal level. While facing challenges in connecting to your team may not be bad per se, it could make things more complicated when getting them to trust you and vice versa. For each scenario, think about what you can do to prevent this scenario from happening in the first place or how you can respond effectively once it comes up. By doing this, you’ll develop a set of simple frameworks that you can easily refer to when the time comes, helping you navigate these challenges smoothly. 

Avoid the temptation of being too prescriptive when outlining your method of remediation.  Remember that not everything will play out exactly as you expect, even in the worst scenarios. 

This exercise isn’t about having a detailed plan; it is about priming yourself for what could go wrong. A general action plan will help you respond quickly when things go awry, helping you take the appropriate measures calmly.

Setting expectations with your boss

Before accepting the position, it’s also a good idea to discuss your thoughts and feelings about this new opportunity with your manager.  

Hold off on bringing your manager a list of your “worst case” scenarios until you outline your more general concerns and get their thoughts on them. This may include your career trajectory or how your journey to promotion will be affected should you not be able to turn this team around. 

Elsewhere, you can set expectations on your workload and work hours by putting limits on both, establish when you should raise the alarm, and highlight early signs of burnout that your boss should be looking for to help mitigate overwhelm. Discuss what success looks like to both of you and what timeframe it might take place. Beyond this, talk about what you will do if/when the success doesn’t materialize in that timeframe. 

Once you’ve considered the key elements of taking on a struggling team, it’s a good time to discuss potential worst-case scenarios with your manager. Share the list you’ve compiled and ask for their input on how likely each scenario might be, how they would respond, and their thoughts on your initial plans.  You can also talk to other managers or your boss’s peers to get a broader perspective.

Should you eventually take on the project, continue having conversations with your boss about your turnaround progress, your own workload, and whether/how the scenarios you mapped out are progressing. Checking in regularly gives both of you a better way to review and adjust along the way.

Final thoughts 

Whether or not you’re looking to specialize in turning around struggling teams, taking on this team will present a unique challenge like few others. If the circumstances are right and you can set up safeguards to protect your career advancement, it’s worth giving it a go.