Even Great Leaders Make Mistakes

Over the years, I’ve had the privilege of working with some truly exceptional leaders—smart, driven, and well-intentioned.

And yet... even the best communicators occasionally step in it.

Here are two real-life examples I often share in my keynotes:

Your boss says, “Please have that report to me by the end of the week.”

You hear: “Finish the report by Friday at 5:00 p.m. Got it.”

What your boss meant was: “I need the report on my desk Friday at 9:00 a.m. so I can review it before the weekend.”

You say to a colleague, “When you have a moment, can you prepare the agenda for tomorrow’s meeting?”

They hear: “This task isn’t urgent; I’ll get to it later in the day.”

What you meant was: “Please do this now, because I should have done this three days ago and this is the second time this month I dropped the ball and I can’t afford to be fired because my credit card bill is due in two days and I have to buy groceries so please pretty please do it now so I can send it out and get input from other departments.”

When I ask if this sounds familiar, people laugh, nod, and shout “YES!”—because we’ve all been there.

Clear and concise communication isn’t just a “nice to have”—it’s how leaders build trust, create alignment, and drive results. Here are three common mistakes even good leaders make (and how to avoid them):

• Assuming understanding: Just because you said it doesn’t mean they got it. Try the technique called “looping for understanding”—briefly restate the key points of a conversation to ensure mutual understanding. It sounds like this: “What I heard you say is that you would like the report on your desk by Friday at 9:00 a.m.—is that right?”

• Overloading messages: Too much information muddies the message, so keep it simple. Think less “War and Peace,” more “Post-it Note.” Each paragraph should be—

  • 1 main thought

  • 2–3 short sentences

  • 4–5 lines max

• Avoiding hard conversations: Delaying the difficult often makes it worse. Shift from a mindset of conflict avoidance to one of productive conflict resolution, and think of these conversations as “learning conversations,” not “difficult conversations.”

Great communication takes intention, and the best leaders learn from their mistakes.

What’s one message you need to clarify this week?