I sat in on a session at the Kitchen Cabinet Manufacturers Association conference led by Lee Roberts, Partner and Managing Director at Creative Planning Business Services. He talked about the businesses that fail because of three predictable patterns he's watched play out a thousand times.
He called them "The Three Sins." I thought at first he was being overly dramatic. He wasn't. In this blog, I'll list them out, plus offer additional takeaways.
Sins and takeaways: tips for small to mid-sized business owners
The best intentions don't always produce the best outcome. Here's where a lot of companies get themselves into trouble.
Sin #1: The founder is still one of the top producers
Whether you're $3M or $30M, if the person at the top of the org chart is also closing the biggest deals, building the biggest projects, or carrying the biggest accounts — that's the bottleneck. Producing and leading are both full-time jobs. You can't do both well at the same time.
Confession: I've been guilty of this.
Most CEOs I know in my peer group are, too. It's hard when you're small but mighty — it's the comfortable place to default to. And I know it caps the company.
Sin #2: We promote our best producer to manager
We take the person who is fantastic at the work, and we hand them a team. Then we wonder why they struggle. Doing the work and recruiting, training, developing, and coaching people are completely different skill sets. What usually happens: you lose a great producer.
Sin #3: We promote them to manager and still expect them to do their old job
We give someone the manager title, the manager headcount, the manager problems — and then we keep their old quota or workload on their plate. You've set them up to underperform at both jobs.
This one hits me to the core. It happens to us. We try to adjust the billable workload to accommodate, but it's not perfect. And honestly, I think leaders need some level of being in the work to keep their pencils sharp. Lee would fight me to the end on that. He's probably right. But it's a lot easier to fully separate the two when you're a giant company with endless means. For most of us in privately held businesses, the truth is messier.
His unlock — and the line I keep coming back to:
"My job was not to grow revenue. It was to grow revenue-producing people."
That reframe matters. If you're a CEO trying to grow with smaller teams and tighter budgets — which most of us are heading into 2026 — you cannot out-hustle your way to the next level. You have to build people who can produce at the level you used to produce. The companies that figure this out compound. The ones that don't stay stuck.
I've actually had this conversation recently with one of my key leaders. She's been wrestling with feeling like she isn't doing or producing enough. We've been talking through what success actually looks like in her role — that leadership is about removing burdens and enabling her team to do more, better. She even wrote herself a mantra to remind herself of that. I'm watching her grow into it in real time, and it's a great reminder that the version of "productive" that got someone to a leadership seat is not the version that keeps them there.
The one habit that separates top performers
Lee has been studying high-performing CEOs for 20+ years. He said the single thing he's seen that separates them from everyone else isn't a skill. It's a habit.
Do what you say you're going to do.
Skills you do sometimes. Habits you do every time. The most impactful leaders he's worked with — across every industry — are the ones who follow through on the words they speak, especially the words they speak to themselves. He framed it as the highest form of self-respect a leader can model and the cleanest cultural signal a company can send.
It sounds basic. It is basic. And almost nobody actually does it consistently.
The three questions he asks every employee:
- What do you want more control of?
- How do you feel about our progress?
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What do you see the future being?
I'm adding these to my own 1:1 agenda. They get past surface-level "everything's fine" and into where someone is actually stuck or motivated.
What I'm taking back to my team
A few execution-ready commitments coming out of this:
I need to audit my own time against the three sins. Where am I still producing? Where have I promoted someone without giving them what they need to actually manage?
I need to run the three questions with my leadership team this quarter, then cascade down.
If you run a privately held business — whether you're a founder, a CEO, a department head, or a leader on a leadership team — these patterns are probably playing out in your org right now.
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