Over the years of owning and running a business I have read a lot of books, listened to a lot of podcasts and attended leadership conferences with a desire to get better. Like many small business owners this desire came from failing hard, landing on my face, and not wanting to feel that way again. If you own a business or are in charge of a team then learning to lead better will not only feel better and be more enjoyable, but you will be more successful at the work you are doing. One of the most difficult disciplines to learn has been the discipline of listening. I do not listen well. Just ask my family. Learning to listen better starts with asking questions, and then asking better questions. This requires time to yourself to think about the problem at hand.


Keith Cunningham in his book The Road Less Stupid, talks about a discipline that he does 2-3 times a week called ‘thinking time’. For myself I will find a quiet space, usually a meeting room in a coffee shop, or a rock on the side of Blodgett Peak, and write down thoughts on a whiteboard or in a small journal. I will start with a question related to a specific problem. Putting ideas and thoughts onto paper or on a whiteboard helps with clarity to see how things are working together. The more I do this discipline the better my decisions throughout the week. The weeks where I feel I do not have the time for this are definitely more stressful. Questions help bring me back to the purpose and reason behind an idea or business decision.


“I insist on a lot of time being spent thinking, almost every day, to just sit and think. That is very uncommon in American business. I read and think. So I do more reading and thinking, and make less impulse decisions than most people in business.” Warren Buffett


Dedicate time alone each week for your own thinking time. 


Ask the right question


“The most serious mistakes are not being made as a result of the wrong answers. The truly dangerous thing is asking the wrong question.” Peter Drucker


I am going to take this information straight from Keith’s book as he has clarified this well. 




A great question has three things.


  1. Helps identify the actual problem and not just the symptom that needs to be addressed.
  2. It simplifies the problem making it easier solve.
  3. It expands the number of possibilities to solve the problem.


When I am confronted with a gap or a problem it is rarely the case that the problem I perceive needs to be fixed or repaired. There is something else going on and the perceived problem is just a symptom.


Identifying a problem versus a symptom


Write down one of your 3 biggest problems.


Write down on a piece of paper one of the 3 biggest problems you are facing in your business. You might write down decreased patient or customer census as a problem. This, however, would not be a problem but a symptom. Most of the time we will write down a symptom when asked to do this exercise. I am overweight. My income is too low for my lifestyle. I do not have enough energy and am tired everyday. Failing to identify the underlying problem will cause us to build a solution or a process that is tactical and not strategic. A lot of companies throw money at getting another SEO company to improve their ranking on Google or start a new marketing campaign to boost customers. Failing to ask a better question and assuming the symptom is the problem can be very costly.


“The symptom is what indicates something is wrong, but it does not shed light on what is causing it to show up.” Keith Cunningham


3 Questions

  1. What are the possible reasons I am noticing this symptom?
  2. What isn’t happening that, if it did happen, would cause the symptom to disappear?
  3. What is happening that if stopped would cause the symptom to disappear?


As we know in medicine if we do not identify the underlying problem we tend to just manage symptoms. For myself treating my high blood pressure but ignoring my sleep apnea and lifestyle choices of diet and exercise is not a great ‘long term’ solution.


Asking better questions can…


  • Help us listen to our team and give us better information.
  • Help us identify a problem versus just a symptom.
  • Save us time by improving our solutions.
  • Prevent bad feelings through better clarity and understanding of our team’s needs and issues.
  • Save us money as a business by reducing the risk of mistakes.
  • Improve our practice of medicine by clarifying our patient goals and desires.


The take home


Set time apart each week to ‘think’.


Have a well thought out question that you can think on that will help clarify the problem and help create better solutions.


As you lead, ask good questions. Listening will improve your team dynamics.


Questions to ask


These questions are taken from The Road Less Stupid. This book is about avoiding the dumb mistakes that sabotage growth, profits and business success.


When starting a new project


What is the upside?

What is the downside or risks? What can go wrong? What is the cost of being wrong?

Can I live with the downside or negative consequences that could occur?


Your Business


What have I been ignoring about my business that needs to be corrected?

What areas of my business can be delegated to free me up to do other things that would add more value?

What is my desired outcome or goal?

What does success look like?

What is the obstacle or gap that is preventing me from achieving my outcome?

What is the plan that is our trail or road map to take us from where we are to where we want to be? Success!

What processes and resources need to be in place to execute our plan?

Who will help me execute the plan?