The art and craft

Leading in messy times starts with smart questions, because they are how you create clarity and focus.

Something like this:


  • What’s the challenge here? (problem/need/opportunity)
  • If we solved it, what would success look like?
  • How might we get there, and what’s the first step?


  • In that context, what’s the challenge for how we work?
  • If we solved it, what would success look like for us?
  • How might we get there, and what’s our first step?


  • In this context, what’s the challenge for me?
  • If I solved it, what would success look like for me?
  • How might I get there, and what’s my first step?

As you see, it’s just three questions, targeted at three different aspects of the system.  When we hit problems, it’s usually because we are focusing on some parts at the expense of others.  That happens when we get busy, distracted and pressured, and don’t have a simple, systematic way to refocus.  The idea is not to mechanically define answers to all 9 questions and create a plan.  (Although they do help make plans more robust).  The idea is to learn to use these in everyday conversations, to adapt and adjust when life isn’t paying attention to your plans.

I’ve explored multiple models of leadership, decision making, change, design, problem solving, creativity, psychology, innovation and a whole lot more.  The same core principles of using smart questions to drive useful progress keep showing up.

And in case you are wondering, these are all learnable skills.  They work because we all do elements of this already on our good days.  We just find it harder under pressure, because of some annoying glitches in our programming (ask me about biases, conflict and stress responses).  It helps to get more deliberate and practise more.  I’ve been practising a long time, so I’ve found some short cuts you might be interested in, and some tools to make it easier.