36 Questions Which Lead Leaders

“Judge a man by his questions rather than his answers.” Voltaire
Written by Chris Stricklin on Jan 10, 2019
36 Questions Which Lead Leaders

Leadership is not about having the right answers, it is the ability to ask the correct questions. It is a compilation of lived and learned experiences, the experiential education which bounds your way of thinking and does not define a rulebook.



As a new senior leader, each member of your organization is wondering three things when you arrive at the organization:

Who are you?

What are you going to change?

How do you affect me?

As you evolve into the new leadership role you have accepted, you must continue to develop yourself and ensure the future of your organization. Instead of trying to have all the right answers, instead ask the right questions.

Do you think at your boss’ boss level and above to advise and lead the enterprise?

Do you help the boss develop a consistent decision process and message?

Do you mentor the masses and groom the individuals?

Are you developing your replacement?

Have you established a permitted or permissive environment?

Are your actions and reactions consistently right of center?

Do you manage resistance to encourage positive change?

Do you segregate complexity?

Do your meetings adhere to the ‘what, so what, now what’ logic and flow?

Do you challenge the assumptions limiting your organization?

What is the position of our enterprise?

What is our starting point? Strengths? Weaknesses? Opportunities? Threats?

Who are we?

What do we offer that is unique?

What does success look like?

Do all teammates understand and internalize our mission and vision?

What are our priorities or key actions to permit success?

What activities do we focus our efforts on?

What should we not do?

What should we stop doing?

How do we allocate our resources (money, assets, people, time)?

How do we determine success?

Are we focused on the correct metrics?

What is holding you, your team, your individuals back?

When employees refer to the company, do they use ‘us’ or ‘they’?

Does each change we make decrease the time required, increase efficiency, improve structure or increase simplicity?

Is each level of leader empowered to make appropriate decisions to affect their span of control?

Is each employee empowered to improve their process or area of expertise?

Is each decision maker using the clearest lens possible to make decisions?

Are we aware of the biases we naturally possess with regard to decision making?

Each time we are asked to make a decision, do you ask ‘why do I have to answer this question instead of you’ and push it to the lowest level possible?

Do you allow power to corrupt?

Simply answer these 36 questions honestly and frequently and you will ensure you, your followers and your organization are evolving and maturing.

And, finally, always ask yourself...
Do you ask the right questions or think you have all the answers? 


By Chris Stricklin

Chris “Elroy” Stricklin is an award-winning leadership author, a highly sought after motivational keynote speaker and a Combat-Proven Senior Military leader retiring after 23 years which culminated with CEO-Level leadership of a 7,000-person strong, $7B worldwide organization. During this time, he was responsible for 11,383 personnel, $323M Payroll, $160M Contracts, Creation of 1,891 jobs and local economic impact of $566M.