How to Learn What Your Team is Capable of

I recently finished my newsletter series on how I build high-performing software teams, and in that process, I recalled many moments from my career. One of those memories is a big part of my leadership style and what I want to share today.

I use a metaphor to describe folks professionally: we’re like balloons. Our capabilities are the air blowing the balloon up.

Now, when we join a company, we take on a role. That role has boundaries, responsibilities, and expectations. I call this the shoebox. Our balloon goes into the corresponding box. The organization is like a shelf full of tidy shoeboxes, each box with a balloon inside.

The fairly obvious and traditional approach to leading is to help inflate the balloon to fill the box. Be the best developer, senior developer, manager, product manager, etc., you can be.

As intuitive as this is, it has a pretty obvious problem. What if the balloon is larger than the box?

Leaders and organizations have many ways to view the box, but often struggle to see the balloons inside. So its tough for leaders to get a sense of how big the balloon is or could be. The pre-occupation is which box is the right box and if it is big enough.

I’m sure people are reading this, and you’re thinking, “No way is that me! I treat everyone as whole people!”

Can you name a non-role skill or capability that you and the team depend on? If so, that’s great! If that is harder than you’d like, then read on.

How do you learn about what folks are capable of?

I want to share an approach that I use that I’ve really never seen anywhere else.

Years ago, I was leading a team with a very outspoken person who relentlessly advocated for what they thought we should do. Nobody ever agreed with them, so I would almost always decide not to take their approach. They would never relent, though.

I found myself talking about this with a coach friend at the time who said, “What if they’re right, and you’re holding them back?”


So I went to work after talking through things with the coach and talked to the team and decided we would take this person’s lead, and support them unconditionally. I personally told the individual we’d be doing this and that I would assist them in any way they needed.

Everyone thought I was nuts and disaster was imminent.

It turned out that the individual overestimated their abilities. They could not get their plan to work. They couldn’t get it to happen even with all the help they wanted.

This event gave us a very clear idea of what this person could do and what they struggled with. They learned that, too. There were no excuses. There was no room for “If only.”

I had contingencies in place, so we recovered quickly. I wasn’t upset about the failure, so there was no punishment. Instead, we all knew what they were capable of and continued working with that in mind.

This technique is a core part of my leadership toolkit, and it’s never disappointed me. When I want to see what someone is capable of, I say “Yes” to them and give them unconditional help and support. By the end of the experiment, we’ll both know what they can do and what they still need help with.

I highly recommend giving this little technique a try. Have a backup plan, be sure you can offer the support you must, and say yes to someone.