What’s Really Holding Your Team Back?
We’d like to share a real case study from a recent 1-hour executive coaching session led by Steve Longan, Coach & Director of Research and Development here at Rewire.
What began as a conversation about time management turned into a revealing look at delegation, leadership margin, and the trap of urgency. This lightly edited exchange — shared with permission — offers insights too valuable not to pass along.
When Growth Becomes a Grind
Dom is the founder of a successful service business. Ten years in, they’ve built something real — blue-chip clients, a strong team, and even a pending acquisition.
But in our session, Dom doesn’t look proud. He looks tired.
Dom: “I’m way overcommitted. I’m carrying too much of the load. I either work late or slow down the team because they’re waiting on me. I can’t be the bottleneck, so I just keep pushing.”
Steve: “Because that’s how the company works best?”
Dom: “Obviously not.”
Steve: “But that’s what’s worked for you so far?”
Dom: “Hmmm… actually, yeah. When I started, I didn’t ask whether something was in my job description. Of course it was—it all was. Contractors helped. Then employees. But I was still maxed out…”
Steve: “So you’ve built success on a foundation of taking it all on. Some might call that overcommitting — but it’s gotten results.”
The Pattern Beneath the Pressure
What we uncovered wasn’t just a time management issue — it was a deeply wired success pattern.
Dom: “But I keep doing it even when it’s miserable. Why?”
Steve: “Because it’s worked. Overcommitting may feel like your success strategy. Letting go might feel like letting go of what made you successful.”
Dom nodded. And then I asked:
Steve: “How’s that going to work when Grove - the competitor you’re acquiring - joins the team next year?
Dom: “[Expletive] This isn’t going to work. Not like this.”
Growth Requires Letting Go
Dom: “This next jump is too big. I’ve made incremental jumps before. This isn’t that.”
Steve: “What was one of the first things you delegated when you started?”
Dom: “Billing.”
Steve: “You couldn’t do it?”
Dom: “I could. I just hated it. Took too much time.”
That’s the point.
Delegation doesn’t start with capacity — it starts with clarity. Just because you can do something doesn’t mean you should.
👉 You can delegate more than you think.
👉 You don’t need a full-blown crisis to start.
The Real Question
Dom was listing out all the major things he takes on as part of his role. But, given that we don’t have unlimited time in a session, I cut in with:
Steve: “Let’s not start with everything in the company that needs doing. That’s been exhausting since day one. What is the work that only you can do? The work that, if you focused on it, would have the biggest impact?”
That opened up a string of insights for Dom. He realized:
💡 He was doing work that wasn’t his to do anymore
💡 He had been delegating reactively — only when overwhelmed and not consistently enough
💡 He was bottlenecking because urgent ≠ important
🌟 And that was Dom’s breakthrough.
Urgency Masquerading as Importance
We revisited the classic Eisenhower Matrix: Urgent vs. Important.
Most bottlenecks live in Quadrant 3 — tasks that are urgent but not truly important. They feel like fire drills, but they aren’t strategic. Recognizing the difference frees up real leadership space.
Why Margin Matters
The final insight landed as Dom reflected on what it really means to lead:
“The organization is always going to throw things at me I didn’t anticipate. If I don’t have margin, I have no capacity to deal with the unexpected.”
Exactly.
‼️Margin isn’t a luxury. It’s what makes real leadership possible. And you don’t get margin by working harder — you get it by letting go of the work that no longer belongs to you.
Your Turn
Dom’s insights may not be yours. But the question that helped him might help you too.
🤔 What is the work that is uniquely yours to do?
🤔 What work, if you focused on it, would have the biggest impact on your company?
This question:
✔️ Unclogs hidden bottlenecks
✔️ Eases the grip of overcommitment
✔️ Helps you re-center in the role your company needs from you now
We’d love to hear what it opens up for you. Drop me a line to connect on this topic.
Ready to get out of your own way?
If you're feeling overcommitted, bottlenecked, or stuck in the grind of doing it all (like Dom) — you're not alone. We help leaders like you identify what’s truly theirs to do, delegate more effectively, and build the margin needed to lead well.
If that sounds like you, schedule a free consultation with Jason Abell, President of Rewire.
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Written by: Steve Longan, Director of Coach Training Programs
