The challenge of leading

Work is not about being busy.  We can all do that.  Work is about making a difference.

As Steve Jobs said : “We’re here to put a dent in the universe”.  It doesn’t have to be a big dent every day, but wouldn’t it be good to see more impact from your efforts, and to feel like you are more of your real self at work, not just constantly under pressure?

Here’s what I’ve found is a useful way to think about making that happen.

The work of a leader essentially boils down to two things:

  • running the business – operating and refining things as they are;
  • changing the business – evolving and transforming things for the future.

Changing something while you are running it is messy.  People are involved, and they bring excitement, distraction, uncertainty, and tension.  If we can deal with those, we manage the tangibles of any change relatively well (the strategy, structure, systems, etc).  But we don’t get benefits from the tangible stuff until people work differently.  The thing that makes the dent in the universe is not the restructure or the digital strategy.  It’s people making new sense of it together and starting to work in new ways.  Including you.

That’s the triangular challenge of leading:

  • you need to change the business while operating the business
  • you need people to change how they operate while delivering results
  • you need to change yourself while leading

Psychologists tell us this transition from the old to the new takes effort because we like the speed and confidence that comes from using familiar solutions.  Shifting that means pausing slightly, so we can get confused in a useful way:

  • releasing our grip on what has made sense so far
  • starting to make new sense of what we want instead
  • exploring and experimenting to find out how to bring it to life

There’s a simple basis to starting this well.  The art and craft of asking smart questions.  They get you through the confusion.

“We can’t be creative if we refuse to be confused. Change always starts with confusion; cherished interpretations must dissolve to make way for what’s new.”
Margaret J. Wheatley

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.

What I do

My name is Alan Arnett.  I’m a seasoned thinking partner and coach for leaders who want to make a difference when life gets messy.  I show you how to navigate complex situations, connect people, and create new options for yourself, even under pressure.

Contact me to ask about:

Informal chats to discuss the challenge of leading in messy times

Coaching packages to help you learn the art and craft of smart questions

Tailored interventions to accelerate the impact of key priorities
(e.g. restructures, mergers, collaborations, innovation, technology)

Events, workshops or talks for large groups.

You can connect with me using the links to Twitter or LinkedIn below, or email me using my first name at this web domain.

“All change, even very large and powerful change, begins when a few people start talking with one another about something they care about.”
Margaret J. Wheatley

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