248. The Illusion of Letting Go

The CEO Help Desk from Run Like Clockwork

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