The First 2 Questions of Leadership


Leaders are inundated with complex projects, decisions, and conundrums every day. It’s a rapidly changing world. And in the midst of it, we’re faced with the daily task of delivering value in the marketplace while empowering people to be the best contributors they can be in the workplace. To navigate these complicated waters effectively, leaders need a mental model that guides their thinking and behavior. A meaningful and personal  leadership model helps us to be consistent in our behavior and anchors us to our most closely held beliefs and principles; this means that even when things are very difficult we can rely on our model to keep us grounded. When we have a model, we can nimbly adapt to problems and apply our skills in the most helpful way while remaining confident that we won’t betray our own leadership code.

How do we arrive at a model that works for us? It’s a continuous improvement process that requires a lot of thought-provoking and energizing work. It took years of reflection, practice, and studying for Doug to arrive at the ConantLeadership Flywheel – but it was well worth the effort. He can be confident that all of his actions are anchored in a self-sustaining (and transparent) circle of highly effective leadership principles. He can hold himself accountable to the model – and so can everybody else. It provides consistency and structure while facilitating integrity-laden leadership.

Leadership is an inside-out craft.

So while it’s certainly not a simple endeavor to develop a model, it is among the most worthwhile work you will do on your leadership journey — and it will pay immeasurable dividends in your ability to empower, inspire, influence, and contribute. While there are lots of exercises we must do on our journey to create our own, distinct model (and we won’t cover them all in this post) it’s important that we do some substantive reflection and inward-looking first. Leadership is an inside-out craft. Before we do anything else, we’ve got to answer some essential questions that will set us correctly on our path. There are 5 vital questions in total: 2 Questions of the Head, and 3 Questions of the Heart. In this post, we’ll talk about the very first two questions of leadership — the questions of the head.

Questions of the Head.

These questions will help illuminate and bring to the surface the insights that already lie within you — insights that you’ve gained, possibly without even being consciously aware of it, from the experiences you have already had as a leader. As you reflect on these, you’ll be surprised how much you have already learned about what drives people to perform. And you will be encouraged by your abundant capacity to leverage your insights to create superior performance. Most importantly, exploring these questions will help you better understand how to harness other people’s talent, energy, creativity, and commitment and transform that into optimal outcomes.

1. What makes people give the very best of themselves?

To begin thinking about this question, reflect on what motivates you. Were you most driven in your career when you were chasing a bonus or raise, when you were seeking the respect of a mentor or superior, or perhaps when you were perplexed and intrigued by an intricate problem that needed solving? Maybe you were most motivated in the wake of receiving some hard-won praise, or when you helped other members in your team reach or surpass a tough target. Of course, what motivates you may not be what motivates other people. Think about the other people on your team. When did you observe them being most invigorated by a challenge or most propelled to surpass expectations?

Similarly, think about times when you have seen the people with whom you work pulling away, becoming disengaged or detached. Do they respond poorly to too much pressure, to a fear of failure, or an absence of sufficiently challenging tasks? Write down everything that comes to mind. Good, bad, ugly, inspired, fantastic. Later, you’ll be able to synthesize all the nuggets of wisdom you’ve unearthed from your reflection into a cohesive model. But for now, try to summarize what you think drives people based on this exercise. If you were going to tell another leader how to engage people, what would your top piece of advice be?

2. What makes for ever stronger performance in an ever changing world?

This question goes beyond exploring the motivation behind performance (which is what the first question addresses) – and asks you to think about successful practices and tactics. What have you learned from achieving results in your career? What successes were you able to replicate? Were you ever part of a team that felt so in sync and so productive that good results came organically? If so, what created the magic? Try to identify specific actions or components that brought about desired results or superior performance throughout your career. Again, write everything down. It can be a stream of consciousness paragraph, a bulleted list, a pile of post-its, or even a spreadsheet — whatever best helps you to organize your thinking.

Now, think about the best-performing bosses, mentors, coaches, or colleagues you’ve observed on your leadership journey. The stars and standouts. How did they approach problem-solving, big projects, and lofty goals? How did they create momentum? What steps did they take to deliver results? In what ways were they able to get the job done in the here-and-now while setting the stage for the performance to continue in the long-run?

Were you ever part of a team that felt so in sync and so productive that good results came organically?

The final piece of this question is to conjure the cautionary tales you’ve witnessed. What bosses were lousy? How did they deflate or belittle people? How did they contribute to a toxic culture – or worse, how did they manage to dismantle a highly-functioning culture and reduce it to a stunted, low-performing, or highly political culture?

When you’ve written everything down, try to summarize what you’ve learned from this introspection into a few guidelines. Imagine that a new leader has asked you for some advice on what practices work for cultivating high performance. In a few sentences, based on this exercise, what would you tell them?

As you work through these questions, we’d love to hear from you. Drop any enlightening insights you uncover as you go through the exercise in the comments.

career, introspection, leadership development, leadership model, management, questions, reflection,
  • Beverley Powell

    Wow! This is a thought provoking article. Thank you.

    • DouglasConant

      @beverley_powell:disqus Thank you, Beverly! So glad to hear the post resonated.