08/25/2026
One of the leaders I was coaching kept postponing an important conversation with a member of his team.
Each time we met, he had a different reason.
"I'm still thinking about how to approach it."
"I want to gather a little more information."
"I just don't feel ready yet."
Finally, I asked him a simple question. "What are you waiting to feel?"
He smiled and said, "Confident." We assume confidence comes first. Then we act. But leadership rarely works that way.
Confidence isn't the prerequisite for courage. More often, it's the reward.T
Whenever you're facing a leadership challenge, don't ask:"Do I feel ready?" Instead ask:
• What's the first step I can take today?
• What's one conversation I've delayed long enough?
• What's one decision that needs my leadership—not more time?
Waiting feels productive because we're thinking. Sometimes preparation quietly becomes procrastination.
Not every delay is procrastination. Sometimes the best leaders pause to gather facts, regulate their emotions, or choose the right moment. But when waiting is driven by fear instead of wisdom, it rarely makes the conversation easier—it usually makes it harder.
I've never had a coaching client regret addressing an issue with honesty, respect, and preparation. I have had many regret waiting too long.
Leadership isn't built by avoiding uncomfortable moments. It's built by stepping into them.
Think about one leadership conversation you've been postponing. Don't rehearse it another week. Schedule it today.
Looking back over your career, when did taking one courageous step build more confidence than waiting ever could?
Leadership doesn't begin when you feel ready. It begins when you choose to act. Let's develop leaders with the confidence to take the next step. [email protected]
www.reynoldscoaching.org
Developing Leadership Success Through Thoughtful Coaching