Hey CEO, What is Keeping You Up At Night? And a more important question

In my coaching practice I often rely on a set of questions that I have formulated to help my executive coaching clients to build greater self-awareness.  My coaching approach is focused on helping leaders to heighten their self-awareness, and then to translate that awareness into better performance.  Over time, the questions I have been asking have evolved and insights gained have led me to create new follow up questions.

A topic that I like to probe with executives relates to delegation and how they are empowering their direct reports and sharing responsibility.  I find that there is a clear dichotomy between enterprise clients and SMB clients in terms of the burden placed upon the CEO and senior team.  In enterprise clients the c-suite leaders tend to insulate themselves from accountability, whereas in SMB companies the CEO or c-suite executives carry the full burden of responsibility for organizational performance.

Sleepless executive

Sleepless executive

When coaching CEOs and c-suite team members one of my go to questions is: “What keeps you up at night?”  The question helps me to understand the pressure points in their businesses and how they are handling the stress associated with those pressure points.  The answers are often surprising.  While I get the traditional concerns around financial results, customer satisfaction and other metrics driven indicators, it is the team dynamics, talent issues, corporate culture and people related issues that tend to keep executives awake at night more than the results.  I think this is a good thing.  My philosophy has always been that if you take good care of your people and you have the right people working on the right things your customer satisfaction and financial results will be good.

While “What keeps you up at night?”  is a powerful questions that provides important insights, the follow up question tends to yield even more important data.  That question is: “Does what keeps you up at night also keep your direct reports and other key employees up at night?”  If the answer is no, then the CEO or executive leader is not sharing the burden appropriately.  The hero CEO approach seldom works.  The job of a senior executive is to identify the challenges and opportunities and then empower his/her teams to solve for them.  Effective leaders share their concerns with their teams and ask for help in solving for them.  Leading an organization needs to be a team sport.  If the team all understand the issues and priorities they can most effectively solve things together.

What I have found is that too many CEOs make the issues that keep them up at night their problems rather than those of the organization.  If you are in a position of leadership, ask yourself these two important questions?

  1. What keeps you up at night?

  2. Do the things that keep you up at night keep your direct reports up at night too?

If the answer to #2 is no, then you should probe deeper as to why you have not engaged your direct reports in solving for the issues. 

I coach several executives from high growth venture backed organizations and my experience in these organizations is that the CEOs are overwhelmed with the responsibility riding on their shoulders.  As they learn to lean into the issue and engage their teams in solving the challenges, it frees them up to tackle opportunities and spend their time more effectively. Executives must learn to ask for help and to reach down into the organization for expertise. Solving problems by bubbling them up to the c-suite is not a scalable approach. Companies end up with bottlenecks and issues when every decision requires executive team input.

If you are a CEO or senior executive and find yourself awake in the middle of the night worrying about work issues, commit to engaging others in addressing those issues tomorrow morning, roll over and try to get a good night sleep. A good night sleep is critical to boosting individual performance. Sweet dreams!