One Click Too Soon: A Leadership Lesson from an Email Mistake
One Click Too Soon: A Leadership Lesson from an Email Mistake
It Happened in a Blink
I hit “Send” on a half-written draft.
Not unusual in the rush of work—except this one went to the Board of Directors of a major public company.
I remember the moment vividly. My stomach dropped. I stared at the screen in disbelief. How did this happen? Why didn’t I double-check the recipient? Why wasn’t the draft saved first?
I called IT immediately, hoping for a miracle.
"Sorry," they said, "we can’t recall emails once they’re delivered."
So I waited. For a fallout. For questions. For embarrassment.
But… nothing happened.
No replies. No acknowledgments. Not even a “Did you mean to send this?”
Just silence.
When Silence Teaches the Loudest Lesson
Though the incident passed quietly, I couldn’t stop thinking about it. It was a reminder that small things can have big consequences—or, in this case, a lucky escape. But next time, I might not be so lucky.
So, I turned the embarrassment into a system. I started a checklist for myself. Not just for emails—but for all critical actions.
Because what started as a simple “oops” turned into something deeper:
A leadership mindset shift about how we design our actions, anticipate risk, and bounce back from mistakes.
3 Leadership Lessons Hidden in One Mistake
1. Process Before Panic: Build Systems
That day taught me to never trust convenience tools blindly.
Autofill is a timesaver—until it betrays you. I double check aliases that look similar carefully.
Now, I never enter names in the “To,” “Cc,” or “Bcc” fields until I’m ready to hit send. And I rarely use “Bcc”. Send me a note if you want to know why.
Instead, I follow a mini-process:
Draft first, names later.
Preview the message.
Breathe. Then send.
It’s basic, but it works. And it prevents a repeat of that moment.
Leadership Insight: When something goes wrong, ask—What quick system could prevent this from happening again? Then build that into your workflow.
2. Regulate the Spiral: Pause, Don’t Panic
I spiraled fast after hitting send. I imagined public embarrassment. I saw worst-case headlines in my mind.
But in reality? It wasn’t a big deal.
Nothing happened. No harm done. Most likely, no one even opened the message.
That silence showed me something powerful:
Panic often comes from our own minds, not the actual outcome.
Yes, mistakes hurt. But emotional recovery is a skill.
These days, I pause, breathe, and ask: What’s the actual impact here?
As leaders, we need to stay centered—not just for ourselves, but for our teams watching how we respond.
3. Mistakes Happen: Learn Loudly, Not Quietly
The biggest mistake would’ve been to ignore the mistake.
Instead, I turned it into a teachable moment—for myself, and now for others.
I’ve shared this story in coaching sessions, in team meetings, and now, here. Because the most unforgettable lessons often come from the moments we wish we could forget.
Leadership isn’t about never messing up. It’s about what you do next.
And if you can build a better habit from the misstep? That’s leadership growth in action.
From Accidental Email to Intentional Practice
Here’s what my personal checklist looks like now—feel free to adapt it:
✅ No recipient until the end
Leave the “To,” “Cc,” and “Bcc” lines blank until the message is completely ready.
This prevents accidental sends and gives your brain a natural pause before committing.
✅ Watch the autofill
Outlook and Gmail love to help—but we can choose the wrong alias or name which looks similar. Always confirm carefully.
✅ Don’t rely on "Undo"
Not all email systems let you recall a message or the time window is too short. And even if they do, people may already have read it.
✅ Pause before pressing Send
Literally sit back. Take a breath. Read it once with fresh eyes. You'll be amazed at what you notice.
✅ Never send important messages when emotional
Angry? Anxious? Tired? Draft it and walk away. Come back with a clear head.
How This Applies Beyond Email
This story may be about an email, but the lessons reach far beyond your inbox.
Here’s how the same principles apply across your leadership work:
What Would’ve Helped Me Back Then?
In hindsight, I wish I had done two things:
Used a drafting tool outside email for email recipient list
If an email needs to be sent to multiple people, I create the list outside of email first.Had a checklist for high-stakes comms
No one teaches this stuff in school. But we should.
So here’s a printable prompt to stick near your laptop:
📝 Before You Hit Send: A Manager’s Mini-Checklist
Is the message clear, respectful, and complete?
Are the recipients correct—and necessary?
Is this the right time and tone?
Have I waited at least 5 minutes after drafting?
Do I really want to send this now?
If not, pause and revise.
Final Thought: Mistakes Don’t Define You—Your Systems Do
That one mistaken email could have made me fearful.
Instead, I chose to build a habit.
And that habit made me a more thoughtful leader.
You can do the same—whether it’s with email, meetings, delegation, or decisions.
Build the process. Calm the panic. Learn the lesson.
And when you do slip? Don’t hide the story.
Share it. Someone else might just need it.
What About You?
What’s the most unforgettable mistake you’ve made at work?
How did you bounce back?
👇 Share in the comments or send me a message—your story might help someone else avoid the same trap.
