• Toby Sinclair

5 Questions That Inspire How I Lead

Judge a leader by their questions rather than by their answers.

- Toby Sinclair (Inspired by Voltaire)


5 Questions that inspire how I lead

Great leaders ask great questions.


They ask these questions most of themselves, not only the people they lead.


To become a coach-like leader, I have spent over 10,000hrs practising the art of asking questions.


In doing so, I have asked many of these of myself.


Here are 5 questions that have inspired how I lead:


  1. What’s the ONE Thing I can do, such that by doing it, everything else will be easier or unnecessary?

  2. What am I chasing? Antelope or field mice?

  3. If the worse case happens, how can I get back on track quickly?

  4. What is it that needs doing, that I know something about, that probably won’t happen, unless I take responsibility for it?

  5. What am I optimising for?


Here is why these questions work:


What’s the ONE Thing I can do, such that by doing it, everything else will be easier or unnecessary?

Inspired by Gary Keller - The One Thing.


I ask this question almost daily.


It works by focusing on subtraction rather than addition.


Less is often more.


What am I chasing? Antelope or field mice?

Inspired by Tim Ferris


I always have more problems than I can possibly solve.


It’s easy to chase the field mice. Small but easy problems.


I aim to find the courage to chase the antelope.


If the worse case happens, how can I get back on track quickly?

Inspired by Tim Ferris


Fear Setting is my favourite self-coaching tool.


It helps you recognise that our darkest fears


Are just stories in our minds.



What is it that needs doing, that I know something about, that probably won’t happen, unless I take responsibility for it?

Inspired by Buckminster Fuller


I’ve had this stuck on my monitor for the last 3 years.


I still don’t have a clear answer.


But I reflect on it daily.


What am I optimising for?

Inspired by Craig Larman


I mostly enjoyed Large Scale Scrum (LeSS) training for its focus on systems.


In particular, the optimising goal of adaptability.


I ask this question often.


It surfaces trade-offs and priorities.