Doubts Instead of Quick Decisions

​

I used to lead from certainty.
Now I’m learning what it means to lead while staying in doubt.

Years ago, I secretly enjoyed comments like these from business leaders:

“When you speak, everything changes for me. So I don’t speak to you very often!”
“I feel you are so persuasive, I have to do what you say, or else.”
“You’re intimidating; you make pronouncements and you’re never in doubt.”

I’m not proud of those years when decisions felt easy, when I was undeniably, even insufferably, “never in doubt.”

Back then I sorted decisions cleanly into: success or failure, worthy or unworthy, on track or off. Every situation demanded a verdict. I decided quickly because I’d “been there before,” and because indecision felt like wasted time.

I’d say out loud, “Let’s choose a path and keep it moving!”
What I’d say inside was different: “Shut down the messy hesitations!”

Doubt used to feel like rats under my cabin floorboards. They had the run of the place. They were invasive, impossible to ignore, and I worked hard over a couple of winters to barricade them out.

But over time, actually seven decades of living, I’ve learned something: the goal isn’t to barricade contradictions out. It’s to make room for them without letting them run rampant. The rats were like the unanswered questions, the perspectives I didn’t have patience for yet.

What finally changed wasn’t a single failure, but a slow recognition that my certainty was often louder than the whisper of doubt. Doubt is now keeping me from leaping too quickly to decisions. I’m learning to hold contradictions without one cancelling the other. I can be strong in my convictions and still genuinely curious about yours.

The right dose of doubt now protects me from offering clients single, simplistic strategies, or mistaking confidence for clarity. Letting colleagues know I have doubts makes it safer for them to question my decisions. And in doing so, they often improve my thinking.

This is close to what John Keats called “Negative Capability”. The capacity to sit in uncertainty without rushing to a verdict.

For me, as a leader, that now looks like:
• holding questions longer,
• resisting being impressive in my certainty, and
• making space for ambiguity before deciding.

Doubt is a healthy hesitance. Hesitating and not rushing decisions is slowly making me a wiser, gentler leader.

How does “either/or” decision making show up in your work?
What gets lost when you don’t leave room for doubt?

This is the last of four posts on how I'm trying to think or live between: “either-or”; “black-white”. Let’s discuss it together. MS Teams, Fri, Feb 6 at 7:00 AM.

Send me a message and I’ll send you the log in details.

I would love to connect with you on LinkedIn or Facebook​

​

See you next week,

Grayson

Did someone forward you this email? Get weekly reflections straight to your inbox by subscribing to The Compassionate Competitor.

Want to share this issue via text, social media, or email? Just copy and paste this link:

[ARCHIVE URL GOES HERE]