By Jean Santos, President, Business Consulting Resources
Succession Installment 3… or maybe 4?)
It’s been a while since my last update on our succession journey, and so much has happened that I’ve lost track of which chapter we’re on. In any case, here’s where I am right now.
This process is nothing short of an emotional rollercoaster. I find myself experiencing it all:
Frustration.
I catch myself asking why things are—or aren’t—happening. Sometimes it feels petty, like figuring out Kyler’s working hours when he’s balancing Honolulu clients, Los Angeles time zones, and travel schedules. Other times it’s bigger—like when I notice “reverse delegating” back to me, or when he doesn’t immediately step in on a project we’re both on. My natural instinct is to just do it (get it done, move on). I know I contribute to this dynamic too.
Fear.
This is always humming in the background. The biggest fear? Whether we’re transferring and building the right skills—especially in business development and sales. Kyler isn’t the only one who needs this, and it’s a skill that is mission critical for the future. Ken, who has always been our strongest rainmaker, is doing an incredible job mentoring the rising generation. And I still ask myself: did Kyler make the right decision leaving his corporate job? Would he be happier there? Or is this exactly where he’s meant to be?
Expectations.
Not exactly an emotion, and at the same time definitely tangled up in all the others. So much of my frustration stems from mismatched expectations. Are the rising gens ready to make the sacrifices needed to grow the company, push the team, monitor financials closely, and make tough decisions? By nature, I’m a high-dominance, results-driven person—and I’ve always been willing to sacrifice myself to get results. The rising gens… not so much. And that’s a real tension.
Delight and Pride.
It’s not all challenges. Far from it. I’m proud when the rising gens deliver strong work that I know will move the needle for clients. When they walk into tough meetings prepared and confident. When they present at conferences and shine. In those moments, you can’t wipe the smile off my face. More of this, please!
Confusion.
This shows up when fear takes over and I spiral into worst-case scenarios about the future. On a good day, I counter with solutions and options. On a bad day… I wonder why we’re even doing this.
What helps me stay grounded is the support system we’ve built. We work with a family business consultant (individually and as a group), and yes, therapy too. Having the courage to have hard conversations—even if not as often as we should—has been invaluable.
The good news: we’re on track with our plan for Ken and me to shift our focus in the company. We still have plenty to work through, and all of us are committed to doing the work. I truly believe—in both my head and my heart— that this succession journey for all its ups and downs is a success.
