Red Flags in Delegation

“I’m at my wit's end.” That was the conclusion of a text message that broke my heart a little bit. when a friend and fellow business owner showed it to me the other day.

Their team member sent it to them, expressing exasperation at the state of unfinished tasks in the business where they were waiting on an answer or action from the owner.

Seeing it bummed me out for both of them because it was neither person’s fault per se (though we can all take responsibility, of course). As I say in Free Time, business stress is a systems problem.

Today I’m sharing the signal flares to look out for indicating that something needs to change, with ways to communicate (and delegate) to stop the stressful pile-up languishing on your desk.

🌟 Key Takeaways: The Burdensome B’s

• Bored: You no longer enjoy the work (same goes for your team members)
• Bottlenecked: Team members are frustrated from waiting for you; you are frustrated that there’s a growing pile at your desk.
• Burned out: You are starting to resent the work, your team, even your clients. Every communication starts to feel like a paper cut.
• Buried by bureaucracy: You are no longer operating in your Zone of Genius because you are so bogged down by tasks that fall into your zones of incompetence, competence, or even excellence (the zone that Hendricks’ says has most risk of lulling you to sleep).

📝 Permission

Stop doing things that you're not even good at—that you dread, that drain you, that you procrastinate on. You also have full permission to stop trying to be somebody you’re not—even if that means a “business owner who is equally brilliant at big, creative thinking and administravia.”

✅ Do (or Delegate) This Next

Keep a piece of paper at your desk (or digital can work): note where you are in your zone of incompetence, competence, excellence, and genius.

🔗 Resources Mentioned

• Articles: The Hendricks Institute—More Happiness and Success Than You Thought Possible (PDF), HBR—Who’s Got the Monkey?
• Video: Read and Grow’s How to Overcome Your Upper Limit Problem and enter the Zone of Genius, Gay Hendricks on Upper Limit Problem — the only problem we need to solve
• Free Time Templates: Delegation Task Tracker, sample job descriptions, and the EOS Quarterly Planning Template

📚 Books Mentioned

• The Big Leap by Gay Hendricks
• Traction and Rocket Fuel by Gino Wickman
• The One Minute Manager Meets the Monkey by Ken Blanchard and William Onken, Jr.
• Team Habits by Charlie Gilkey
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Gay Hendricks’ podcast: The Big Leap
• Free Time: 086: The Cyrano Strategy for Delegating Important Comms, 054: Ten T's of Successful Delegating, 006: Going Pro on Podcasting with Jordan Harbinger

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