One of the hardest decisions Sunny and I have made in recent years came when we looked closely at our leadership team and asked whether everyone was sitting in the right seat for where ITBD is headed. We had chosen to become a company that fully embraces AI and helps lead the conversation around it in our community. To execute on that vision, our leadership team needed to evolve along with it. (Anyone who has rearranged a long-standing org chart knows it feels a little like rearranging furniture in a house where everyone has a favorite chair.)
Last week, I wrote about the weight we carry as leaders, and this decision was a perfect example of it. We had to rearrange what had become a very comfortable and constant norm for all of us, and we were doing it with people we deeply respect. It took a lot of thought and even more change management, and I won’t pretend it was easy.
What I’ve learned over the years is that a leader can’t carry all of the weight alone, and shouldn’t try. My job is to make sure the right load is carried by the right people, and that starts with having the right people in the right seats. When the seats don’t match the people sitting in them, everyone ends up carrying something that doesn’t quite fit, and the leader usually ends up picking up whatever falls in between.
Making the decision turned out to be the easier part. The real work began the day we announced it, because how you manage a decision afterward determines whether it becomes a good one. I’ve seen well-made decisions fall apart because no one guided people through them, and I’ve seen difficult ones succeed because leaders stayed close and kept communicating.
For us, that meant breaking the change into smaller steps, identifying transition timelines, and communicating the “why” personally in each office so everyone could absorb it. People need to know what happens next, they need a reason to trust the person leading them, and they need to see where the road ends up. How you say it matters just as much, because the right words can put a room at ease while the wrong ones can shut it down completely. (I’m a mom of three boys, so I’ve had plenty of practice choosing my words carefully, though I’ll admit my success rate is probably higher at the office 😊)
Timing played a big role, too. The shift toward AI made it clear that the moment had come, even though staying with what was familiar would have felt much easier. Waiting longer would only have made the change harder for everyone, including the people we were trying to protect, and on the initiative we knew we had to lead.
What we gained in return was clarity. Once the new structure was in place, everyone understood the direction of the organization and the role they played in getting us there, and that clarity has been a gift to the entire team. It also means the right leaders can make the right decisions on their own, so hopefully fewer of those decisions need to travel all the way to my desk.
If you’re facing a similar decision, take an honest look at whether the seats in your organization still match where you’re headed, and then put as much care into managing the change as you did into making the call, because the way you carry people through it is what they’ll remember long after the new org chart is in place.
