What Keeps You Awake At Night? (Part I)



In my conversations with leaders about the pressures that they face, it’s common to hear those burning issues described as “the things that keep me awake at night.” I get it. As an entrepreneur, CEO or senior leader there’s a lot of responsibility resting on one's shoulders - from business development to team development, from product innovation to process innovation, from customer engagement to employee engagement. With burnout and mental health challenges becoming a hot topic for senior leaders, there’s a critical change in the way that we lead that would address any barriers to sustained leadership effectiveness.


At the beginning of this year, I participated in a 3-day leadership conference in Lubbock, Texas. The conference was attended by CEOs and their senior leadership teams and covered many fundamental areas, including building a purpose-driven business, aligning culture around a clear set of values and leadership styles. I noticed, as I read the bios of the various speakers, that one of the breakout speakers described himself and his wife as the “Stewards” of their family-run company. I was immediately drawn to that description and had a great conversation with the speaker later that day. I couldn’t help but wonder, what would happen if more CEOs and senior executives saw themselves simply as stewards, responsible for doing their absolute best to look after, grow and nurture someone else’s assets, even if it was in fact a business that they had founded or co-founded?


The answer is that they will sleep more soundly. After all, when you’ve done your absolute best to serve others, when you recognise that your ego or reputation isn’t at stake because you’re not playing that game, when you know that you’ve got nothing to hide and your conscience is clear because you’re committed to acting ethically, at the end of the day, when all is said and done, those leaders who apply the principle of stewardship can sleep like a baby and get up the next day ready to play at a level that very few dare to reach.


Many years ago, I came across a model by Steve Siebold describing the different levels at which people live, think and play the game of life. I think it’s so relevant for leaders (and complements this principle) that I like to use this model with those I train and coach to show what separates the best leaders from the rest.


  1. The first level is – playing not to lose – this is where, as a leader, we’re more dominated by the fear of failure or the fear of not performing well. We do what we do simply to avoid the consequences. It gets us some traction at least.

  2. The next level is – playing to cruise – this is where we’re all about staying under the radar. Still very much a fear-based approach to leading and playing the game of life. Some would describe this as operating at the level of mediocrity.

  3. The third level is – playing to improve – we’re really beginning to switch gears here. As leaders, we’re thinking that we can actually accomplish more than we thought. We might even be better than people said we were. 

  4. The fourth level is – playing to compete – this is where we’re really focused on being the best. We see our peers as competition. A lot of driven and ‘high-performing’ leaders operate at this level. This level is about having strong beliefs and confidence in our capabilities, but we’re still driven by fear and ego. It’s still about what we can achieve. It’s still about protecting our reputation. It’s still about making a name for ourselves. When we lead at this level, we get a lot done but we can also cause a lot of damage to our organisations and the people around us because we’re highly competent, often very intelligent and have a big ego – a very toxic combination.

  5. The fifth level is – playing to win – this is the level where we’re no longer competing with others but competing against ourselves and are focused on achieving and being our personal best every single day. I actually prefer to think of this fifth level as “playing to contribute, to serve, to give,” because,at this level, we’re about learning, growing, contributing, expressing ourselves and running our best race. We’re more attuned to the needs of others and excel at bringing out the best in those around us for the common good of the organisation. We have no need to feel afraid of what others might think or say, because we’re no longer playing that game.

This is why leaders who operate at this level can sleep soundly at night and are way more resilient than their counterparts who operate at other levels.


So, how can you start to operate at this level? How do you apply the principle of stewardship?


More on that in Part II coming soon...


#resilience #character #coreleader

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