In the last 10 minutes of an executive session I was leading, I had to make a decision. I wanted to tie a nice bow around the morning and give the group a preview of what our following conversation would entail. But I couldn’t.
“Is this working for you all? It doesn’t feel like this is worth your time.”
You could hear a pin drop.
We still had several more sessions left in our contract, and few leaders wake up in the morning expecting their trusted advisor to try and fire themselves. I gave them a moment to process, and several of them thanked me for having the courage to speak up and invite some real talk before we dismissed.
In the immediate aftermath, several team members went out of their way to ensure I didn’t feel discouraged about the progress of our work. But the truth is that I had never felt more confident in my work and ability to make change.
I’ve been a consultant for my entire career, and I’ve been facilitating executive sessions for nearly a decade. What comes with that experience is a clear understanding of when and where my work is most effective. A lot of it has to do with personality fit, but other factors are equally important: how the team make decisions, how comfortable they feel speaking up, and how open they are to change.
I went in with high hopes, but sometimes our ambitions don’t survive contact with reality. That’s normal. What we do with this realization is up to us.
It would have been a lot easier not to rock the boat, but I was unwilling to trade short-term comfort for long-term misalignment. The outcome? We decided to repurpose the remaining sessions for work with their people managers—work that everyone is excited for me to deliver.
What’s more: the client sees me embodying my values of authenticity, speaking truth to power, and being open to finding creative solutions.
Willie Jackson helps teams and organizations find harmony. He brings compassion and levity to the challenging work of