248. The Illusion of Letting Go

The CEO Help Desk from Run Like Clockwork

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After coaching Ben and Cody from Five Star Interpreting, Adrienne and Emily are back to debrief the conversation — and dig into what it really takes to evolve from a hands-on founder to a strategic leader.

If you’ve stepped out of the doing but still find yourself making all the decisions, this debrief will hit home.

Here’s what we cover: ✅ The illusion of being “out of the weeds” — and why decision fatigue proves otherwise ✅ How to train your team to spot problems and solve them ✅ Letting go of control… without letting go of clarity ✅ Navigating leadership with a co-founder who sees the world differently ✅ Why self-awareness and communication tools (like the Enneagram) are game-changers

This is an honest, behind-the-scenes reflection on what it takes to truly design your business — so that the right people are solving the right problems at the right time.

Plus, we unpack the metaphor of bikes vs. race cars — and why growth speed can look different even when the destination is the same.

Top 5 Takeaways:

You're Not Out Until You're Unnecessary – If every decision still needs your input, you’re not free yet.
Build Problem-Solvers, Not Just Task-Doers – Your team needs the skills and autonomy to act before they ask.
Shared Vision = Smoother Roads – When co-founders stay aligned, everything else moves faster.
The Enneagram Reveals More Than You Think – Understanding motivation helps reduce conflict and build trust.
Compassion Over Control – Assume your partner is on your side, even when you disagree about the path forward.

Read the transcript here

Chapters:

00:56 – Why “not doing” isn’t the same as “not deciding” 04:42 – Team autonomy starts with training and trust 08:14 – The dashboard difference: measuring + interpreting data 13:00 – Getting team leads to own problems and solutions 17:22 – Working with opposite strengths + communication styles 23:05 – How the Enneagram shifted their partnership 27:36 – Bikes vs. race cars: the real pace of progress 32:04 – Final takeaways + what this means for your business

Connect with Adrienne: @adriennedorisonLearn more about Run Like Clockwork: www.runlikeclockwork.com

252 episodes

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