Real Leaders

A Few Uncomfortable Questions Every CEO Should Ask Themselves

Before strategy, before innovation, before profitability, before talent management, before acquisitions, and before revenue growth, there are two questions a CEO answers (mostly implicitly, unfortunately — my hope is that this piece encourages you to answer them explicitly):

1. What is my ambition for my business?

2. How hard will I strive to achieve ‘optimal’?

These questions shape every choice a CEO makes. They determine what you want for yourself and what you want for your business — a trajectory of sorts. And once this trajectory has been established, your choices follow suit.

A mildly motivated CEO will produce a middling strategy. A highly motivated CEO will produce a remarkable talent plan. A CEO of low motivation won’t care about innovation and the journey to producing a stand-out product or service.

Most CEOs I work with initially are fairly flat regarding these choices, until they become awake to the possibilities in front of them. Once this awakening takes place, the CEO role looks different — more compelling, more interesting, more alive, more enticing — and  true, sustainable business performance follows shortly thereafter.

Observing CEOs undergo this transformation is a beautiful thing for me — a privilege that never loses its luster and which deeply sustains my work and the energy I have for what I do. It’s a change in course that brings about a wide array of changes in their lives: more energy, more optimism, more curiosity, more purpose, more creativity. Even the quality of their marriage seems to benefit, as one example of many unforeseen upsides. Health, too. Financial well-being, obviously. More inspired parenting.

Being a CEO is an opportunity to turbo-charge an entire existence — this is the extent of the opportunity. Check your ambition. Explore what’s possible. A better way likely awaits you.

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Face Up to Your Truth

I’ve heard the phrase “… this year has been a lot harder than I expected …” from more than a few CEOs of late.

As such, it might be worth taking a few minutes to ask some sound questions at this point in 2022. Remember that your businesses are alive, evolving, fluid things. As much as we’d like to see them as walking a linear path that we, as CEOs, have full control over, that is not the case. So, as your business continues its (hopefully) merry way, consider these questions and see what emerges. They are not soft-ball questions, but rather ones that sometimes we might prefer to avoid. As ever, despite their sharpish nature, they are shared in the spirit of care, support, and enablement:

  • What did not play out as you expected it to, and where did your hypothesis go wrong?
  • What is the true, holistic health of your business right now?
  • What truth about your business, or about yourself, might you be avoiding?
  • What bias is in play that might be skewing your objectivity when it comes to big decisions?· 
  • What is your business calling on you to become as the CEO? (changes, growth, what to let go of, what to mitigate about yourself)

None of the above questions will likely have ready answers. And, in fact, one or two might not even be relevant right now. But at least one will have meat on its bones that warrants inquiry. I hope they are helpful.

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