Coaching: Common dilemmas rob business owners of sleep


Readers of this column and my coaching clients teach me a slew of valuable lessons. One of the most valuable is this: people at the top of any organization can get stuck in a dilemma.

There are a handful of these “stuck” situations that crop up at least once in every CEO’s career. These are the situations that plague you when you’re trying to rest your head on the pillow and slide into a refreshing long sleep. They sneak up on you when you’re out golfing on a beautiful day. They may bring out the worst in you. You find yourself snapping at employees, forgetting way too much critical stuff, thinking about numbing your brain with a couple martinis on the way home.

A fulfilling and energizing part of coaching involves helping clients emerge from all that obsessive thinking and move into a problem-solving mode. Together, we shift into exploring possibilities and tapping into the creativity that got crowded out by the old worry bug. Worry inflates like a float in the Macy’s Thanksgiving Day parade. It is a huge waste of the imagination and loves to torture us with worst-case scenarios.

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These worrisome situations are so prevalent among entrepreneurs, that I’ve been encouraged to write a book about the dilemma-busting work I do with clients. And I need your help.

I want to know the banes of your life as a business leader. What kinds of problems follow you home? What situations reduce the smart, confident you into gnashing your teeth and talking to yourself? What happens in your organization to make you think of selling the whole shebang and getting a job as a greeter at Wal-Mart?

Here are some of the tough situations that I hear about repeatedly:

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• Serious conflict between senior managers.

• Inspiring a sleepy sales force.

• Keeping up with technology enough to evaluate your IT department.

• Attracting staff to your vision.

• Clearing out the B-minus and C employees.

• Dealing with the loneliness at the top.

• Planning for your own exit.

• Having a life outside of work.

• Knowing what to tell the rank and file and what to keep to yourself.

A daunting list – and it must be seen as part of the big picture of running a business, most of which is fulfilling and fun to those of us who consider ourselves born entrepreneurs. Business owners cope well with big challenges every day. We must like that part of the job. However, the situations I’ve listed usually hang around and bug entrepreneurs for many days and weeks. Can’t solve them in a 15-minute meeting, can’t delegate them, and can’t ignore them without serious consequences. 

My book will include stories about these stubborn challenges, and creative ways to untangle them. You may have other situations that belong on the list. You may have your own stories of emerging from the horns of entrepreneurial dilemmas. What is the toughest part of your life as a leader? If you choose to send me contributions for this work in process, you can be sure nothing identifying you or your company would ever appear without your express permission.

Often, readers will send me e-mails with interesting stories from their own experience, stories that connect with one of my columns they’ve just read. I’m so grateful for that connection, and now am inviting correspondence about your biggest challenges – ones still bugging you as well as ones you’ve resolved. And, how you did it!

Along with that request I send my heartfelt wishes for a prosperous and meaningful New Year. 

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