A CEO mid-year assessment

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 the mid-year point of 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 definitely not the case.

So, as your business continues on 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 sharp’ish 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)


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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.

Reach out to connect whenever you’d like to. I’m always happy to have engage in a conversation that might help to flesh out your answers to any of the above provocations.



I’m headed to the USA with my kids for two weeks, but I’ll keep the CEO Sundays coming. It’s a large but mostly passive audience that I write to so it’s not always easy to understand how helpful I’m being, but I certainly hope I am and that your CEO practice is benefitting from my writing. Feel free to share feedback if you think it might enhance your experience of my work.

Take care,


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My weekly missive, CEO Sundays, is published at 5pm every Sunday evening. The writings cover CEO topics exclusively: how-to’s; thought starters; leadership insights; reflection opportunities; research.

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