My Favorite Business Coaching Questions (Part I)

I have wanted to be a coach ever since I was 16 years old. In high school, I wasn’t talented enough to play varsity sports, so I decided to do the next best thing… coach. I volunteered to coach little league basketball and baseball. It was a ball!

Not long after that I thought maybe that I wanted to start a career as an athletic coach. My school, Tulane University, had a teacher/coach degree program. Perfect, I thought.

My father thought otherwise. He suggested that I could come home to Miami and attend a local community college and get that education. He said that he was paying too much for tuition at a prestigious private school for me to graduate with a teaching degree. There went my coaching career, at least for the time being.

Flash forward to today. I have been coaching CEO’s and small business owners for almost twenty years. Thousands of them. Funny how things turn out…

Over this time period, I’ve had great training as a coach and have read lots of books. As a result, I have assembled a powerful collection of coaching questions. I will share some with you this month and the remainder next month.

As a small business owner/executive, you are a coach by default. If you have employees, one of your most important responsibilities is to coach your team members to achieve desirable results. Even beyond your own employees, you will find yourself coaching clients, vendors, and friends. In the TED talk I have included in this month’s newsletter, Dr. Atul Gawane makes a compelling case for both the need to coach and the need to be coached.

I hope you enjoy and benefit from using the following coaching questions.

1. “What if you did know?”
Sometimes I will ask a client a question and the response will be “I don’t know”. While the client may not know the exact answer, I am fairly certain that he has at least a good guess. So I will then ask this question as a follow-up and will almost always get a good answer.

2. “Would you rehire that employee?”
The decision to retain or fire an employee is a tough one for any CEO. Sometimes the executive takes an inordinate amount of time to make this decision whether it is a performance issue or a behavioral problem. This question I find helps the executive make the decision in the context of whether she would rehire the same employee sometime in the future. FYI, the answer is usually “no”.

3. “It’s a year from now and your decision has turned out terribly. What went wrong?”
Hopefully most of your decisions go right. When we are considering the outcomes of our decisions we typically focus on the positive. This question forces us to consider the negative consequences of a bad decision and what possible miscalculations might have contributed to that now bad decision.

4. “How do your core values speak to this decision?”
Strategic decision-making is difficult. Whether it is a hiring/firing decision, a capital allocation decision, or maybe a key marketing decision; these decisions are tough for any executive. They are even tougher without the assistance of a set of written core values. The core values serve as a filter or a “north star” for each of these decisions. As an example, if one of your company’s core values is “integrity” and one of your employees is caught stealing; you now have a pretty easy decision. Applying your core values to your decisions make those decisions much easier.

5. “What is your blind spot on this decision?”
Many car wrecks are caused by blind spots. I can’t see that car coming up on my right passenger side until it is too late. Bam! Likewise, every small business owner has blind spots. Information or data or experiences that we can’t see or think of at the time of a decision. Posing this question, the coach is asking the executive to consider what those blind spots might be. What information are you missing that would make this decision easier?

Next month I will share the remaining five questions. Have fun trying these out in the meantime.