One thing I’d tell my 40-year-old leader self: Have the hard conversation.
A while back I was reflecting on one of the only leaders I was never able to build a relationship with. I tried everything I knew to build rapport and trust, but she was not having it.
At the time I believed she just didn’t like me. In retrospect, it most likely had nothing to do with me, and everything to do with her own fears and insecurities about her role compared to mine.
What I didn’t do? Invite in the conversation to explore what was going on.
It could have been as simple as: “I want to have a good working relationship with you, but it feels like something is getting in the way. Can you help me understand what that might be, and what we can do about it?”
Honest. Direct, not softened. Curious, not accusatory. An invitation to improve together, not an assignment of ownership or blame.
But we never had that conversation, because I didn’t have the courage to start it.
Today I do. And I would.
I spent a long time wishing I knew how to have hard conversations. Now I get to be the person who helps others find that courage.
Feedback, conflict, fractured relationships. That’s where many of the leaders I work with get stuck. These are leaders with high emotional intelligence who excel in their areas of expertise, but struggle when it comes time to broach something they believe will be hard.
We explore what’s holding them back and what they’re afraid of. We get to the root of it, then strategize how to address it productively.
And when they go have the conversation, we check in at our next session. More often than not, it goes far better than they expected. Not always—sometimes it goes sideways. But when it goes well, it brings relief, resolution, and improved relationships.
All of that drives better results.
That leader I couldn’t reach? That was nearly 15 years ago. And it was only in the past week that I realized I missed an opportunity.
I give myself some grace. And I use what I’ve learned to help other leaders avoid the same mistake.
What’s the hard conversation you’re avoiding? And if you have it, what might be possible?
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