Your leadership will rise to the level and quality

of the questions you ask yourself.

It’s easy as leaders to find ourselves focused on asking questions that solve the problems immediately in front of us. However, it’s the big-picture questions that either shift how we lead entirely OR focus us on solving bigger, more strategic problems.

Below are 10 of the most penetrating questions I’ve asked top leaders to help them shake up their thinking. My encouragement to you is to pick the ONE question that cuts to your core most and carve out 15-20min to deeply think about it. You likely won’t have time now, but can prioritize the time later this week.

Here they are, in no particular order:

1. What is the biggest lie you’re telling yourself about your business right now – and what’s the cost of believing it?
   
   
2. If I forced you to cut your workweek in half, what would you focus on and what would you finally let go of? (either delegated or eliminated)
   
   
3. What’s the one decision you keep pushing off that, if made, would immediately create the most momentum for your business and your freedom?
   
   
4. If a world-class leader took over your role tomorrow, what’s the first major change they would make that you haven’t been willing to?
   
   
5. Are you leading a company or are you just managing its momentum? If the latter, what 3 things need to change immediately about how you’re currently leading?
   
   
6. How much time do you lose each week by addressing the same issues repeatedly because there’s no space to address the root causes?
   
   
7. What are you holding onto because it makes you feel valuable, needed, or in control, but in reality, it’s keeping you and your business stuck?
   
   
8. If your business were ten times its current size, what problems would you be solving at that level, and why aren’t you working on those problems now?
   
   
9. How much of your time is spent creating the future of your business versus managing the present – and what does that say about the legacy you’re actually building?
   
   
10. If your children or team adopted your current work habits and beliefs about success, would you be proud of the life they’d create or would you warn them to do things differently?

Which question made you feel most uncomfortable? – Let me know!

That’s probably the one you ought to spend some time with! 

Powerful questions are uncomfortable, but it’s in the discomfort that we grow.

Lean into it. Your team and your future self will thank you!