A Leader’s most critical role is ensuring that those they lead
are having the most courageous conversations possible.

One of the core guiding principles of courageous leadership is that you are always evolving the team. No matter what problems you are trying to solve or goals you are attempting to reach, there is ALWAYS a parallel agenda of building, strengthening and supporting a highly productive and creative team culture.

Confident leaders don’t concern themselves
with being the smartest person in the room,
just the most present and attentive.

It is not the leader’s primary function to generate the best ideas. A leader’s most important role is to create the culture and environment where courageous conversations, daring ideas, ingenious collaborations, healthy conflicts and bold actions can take root, grow and thrive.

I’ve been facilitating team and leadership development programs now for almost 30 years. And in that work I have guided thousands of teams through experiential activities where they get to work together to generate solutions to problems. It is exceptionally rare that I come across a team that will purposefully choose a leader to hold themselves somewhat apart from the “problem solving” aspect of the activity and instead take on the role of creating and maintaining an environment within which the team can do their best work.

It is the quality of the conversations being held
that has the biggest impact over the quality and creativity of the results.

Consider the leader to be akin to the conductor of an orchestra. Without the conductor the performance of the even the most dedicated and passionate of symphony musicians just wouldn’t be as brilliant.  It is the quantity of music they play or how loudly or even how passionately.  It is the grace, synergy, attentiveness and fluidity with which they crete their music that makes the difference.  And that ability to be graceful is held and supported by the leader.

The leader holds the Mountaintop Perspective.

It is often a good idea to have the lead on a project be the person who’s nose isn’t buried in the details. This allows the leader to keep an mountaintop perspective on how the team is working together and how the progress being made is aligning with the overall objective while others dive into the gritty details of the project.

Teams often mistakenly think that the person with the best idea about how to solve a problem or the most creative thinker should be the leader of a project. Then when that person get’s so focused on the task and swimming in the details the team is left without a leader who can truly see the big picture. Don’t shackle your most creative thinkers with the need to be both in it all and above it all at the same time.

Hold space for Courageous Conversations and let innovative results
you might never have imagined blow you away.

Poet and philosopher, David Whyte speaks to the idea that rather than focusing solely on finding solutions and making the changes that you think need to happen, it is far more powerful to simply create the opportunity to have the most courageous conversations you can have.

When we focus not so much on finding solutions but instead focus primarily on creating the conditions where courageous conversations can occur, then far more bold and innovative solutions that we might never have imagined will instead find us.

This is a practice that takes the discipline of a truly courageous leader. A faith needs to be employed here. A faith in your team and a faith in what can reveal itself when you set the stage for people interact at a deeper level of intimacy and courage.

The additional benefit to this concept, beyond yielding more imaginative ideas, is that your team feels the faith that you have placed in them. They rise to the challenge with courage, accountability, responsibility and the ability to handle the most difficult of encounters. They grow, evolve and become stronger individuals and a stronger team. Bonus! You achieve outrageous results while simultaneously strengthening your team.

Leaders ask questions that others can’t see to ask.

When everyone else is deeply invested in the task, the leader is the one who who’s paying more attention to the process. She is the one who has the discipline to step back and listen and observe. She is the one who, from this leadership perspective, can “feel” how the team is progressing and how effectively they are working together. When she does this, she can see very clearly what questions need to be asked to keep the team in alignment with their greatest strengths and abilities.

“You can tell whether a man is clever
by his answers.
You can tell whether a man is wise
by his questions.”
~ Egyptian Author, Naguib Mahfouz



Critical questions might include:

  • Has everyone had an opportunity to contribute?
  • Did you all hear what Joe just said? It is a critical point he makes.
  • Are we asking the right questions?
  • Have we explored enough ideas or are we chasing the first idea that sounded plausible?
  • Make a plan (And then ask more questions)
  • ALWAYS ask – Is everyone clear what our plan is?
  • Is everyone clear what their role is?
  • Set clear actions with clear timelines.
  • What are the exact actions that need to be taken to implement our plan or ideas?
  • Who is taking lead on these actions?
  • When can the team expect this action to be completed?
  • What will that action step actually look like?

Core Actions:

  • Create time and opportunity for the right people to collaborate.
    • This won’t always happen on it’s own within a time pressured environment.
  • Hold meetings in a space conducive to open dialogue and creative expression.
    • Consider lighting, windows, temperature, privacy, open space, tools for capturing the outcomes of the creative process.
  • No matter how small the task or scope of the meeting, choose a leader to facilitate the process. Some call this a process monitor, but this is more important than that. You are choosing someone who is going to LEAD you through the journey of your meeting.
  • Educate your team in the art of engaging in healthy conflict.
  • Educate your team in the art of innovative collaboration.
  • Ensure that your team really knows each other and has developed a powerful sense of Team Viscosity.

These are just a few initial guidelines and considerations for the Courageous Leader. There is a lot more to explore. The well is deep and the opportunities are profoundly rich when leaders can keep an eye on the big picture while others relish in the engaging details of making the magic happen.

Chess Edwards and his team are ready to support you and your teams as you achieve the highest levels of Courageous Leadership and deliver Outrageous Results!