Is it Time You Gave Up? A Leadership Coaching Case

The owner of a big printing shop had been preparing to sell his company for months. He had a dream to retire and be philanthropist, giving back in gratitude for his good life. When he came close to the date to put out the offer, he kept coming up with dramas at work he needed to fix. Then we he asked to reschedule our coaching session, I asked for five minutes of his time.

First, I reflected to him what I saw happening in the past month, that little problems where escalating into disasters and he was uncovering issues that were never bothersome before. He asked me if I thought he was making up stories.

“No.” I said, “but I do think you are going out of your way to find difficulties that need your attention.” I let my words sink in before I said, “You don’t have to sell your business if you don’t want to.”

After a long silence, I said, “Which would make you feel relieved, signing to sell or tearing up the contract?”

He said the thought of selling made him feel sad.

I asked, “What’s the loss?”

He said his employees were like family and he didn’t like the idea of leaving them behind.

“Are you willing to live with the loss to meet the philanthropy goal you set for yourself when you sell the business?”

After a long pause he said, “No, I don’t want the loss. And maybe I can start on my goal in a smaller way. But am I wrong to say I don’t want to sell? What will people think of me? I’m selfish and wishy washy?”

“Which is worse, having people think you can’t make up your mind or not seeing your work family every day?”

“But what will everyone say?”

“Sounds as if you are letting your fear of judgement get in the way of your happiness.”

“But what will I tell them, the people at work who have been prepping for me to leave?”

“What was the reason you told me that made you reconsider selling?”

“I like the people I work with. They are like family. I guess I’ll tell them that.”

He decided to end his search for a buyer.

Some goals are good to hold onto no matter what. Some seem to be good when you create them but then don’t inspire you later on. And then there are the goals you think you are supposed to do based on what other people have said you should be doing but don’t align with your core values. Blindly marching forward with your goals because you think you have to do what you said could leave you with more regrets than joys.

Whether you are making career goals, business decisions, or life choices, the moment you make a decision you should also create criteria to evaluate if you should stay on the path or not in the future. Once on the path, your fears of how others might judge you can get in the way, keeping you from changing your mind when your procrastination is signaling it is time to reassess your goal. A good checklist will keep you from separating your desires from your fears.

When you make a decision, write down:

  1. Why did I make the decision?
  2. What outcome do I expect? Why is this outcome important to me?
  3. What am I leaving behind? Is what I want to achieve worth the loss?
  4. What have I learned about myself in pursuit of my goal? What else have I learned that I didn’t know when I made my decision?
  5. What will I gain by sticking to my plan now?
  6. What might I regret by sticking to my plan?

Keep the questions close and set an appointment with yourself to review them monthly for long term plans and weekly for more short-term goals. Answer the questions honestly. Is it more important to save face or to be happy? Living with people’s negative judgments of you is generally short lived, especially if you are clear why you have changed course. Living with regret lasts forever.

2 thoughts on “Is it Time You Gave Up? A Leadership Coaching Case”

  1. As a financial and retirement planner, this story was very poignant to me. I help people with the “numbers” part of decisions like retirement or selling a business but what is often even harder for them is the emotional piece. These questions you pose will help me help my clients with these types of decisions – thank you!

    1. Marcia Reynolds

      Glad to help Melissa. Emotions always impact logic. You have to clear the way first before the “pros and cons” conversation makes sense.

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