Three Founder Retreats, One Pattern This COO Can’t Unsee

I have attended three Collective 54 retreats in the last 7 months. I am not a founder – I am the COO of a boutique professional services firm.

For founders of growing firms, retreats like these may feel familiar. For most COOs and certainly for me, they do not. I have an unusual seat at your table and sit in your conversations as a bit of an outsider.

After three retreats, I have something to tell you.

Your problem is older than your firm, simpler than you think, and not yours alone.

What I Keep Hearing

Last week, a founder told me one of their leaders was struggling with resource management. They had described something similar to me at a previous retreat and tagged it as an “availability” problem.

Another founder said their sales team was not “hungry” enough. They then described an incentive structure that quietly rewarded comfort.

A third founder said they needed to hire more people because their team was stretched thin. They then revealed their billable utilization at the manager level (high!) and the junior staff level (low!).

Three different conversations, three different industries. The pattern was the same even though the underlying issues looked nothing alike.

Older Than Your Firm

Very little is new under the sun in business.

I’m a proud Gen Xer and have lived through some seismic shifts in my career. Yes, AI is real and reshaping how we work. I am leading a game-changing agentic AI rollout at my own firm right now. But in 2000, I was marketing online media players in a time when most people did not yet own a smartphone or even have broadband internet. I looked up the definition of “streaming” on my first day to make sure I had it right.

That dotcom went bust. I walked in one morning and found my desk and chair being loaded into an 18-wheeler. My boss told me I no longer had a job. That is what disruption looks like up close.

After that, I spent a decade at IBM. There, I sat through the post-9/11 rebuild. I was an enterprise account manager the year the iPhone came out. I threw away my Blackberry and hosted app parties with my colleagues during lunch, before we even really knew what an app was. I threw a big industry party for my clients when IBM Watson took out Ken Jennings and Brad Rutter on Jeopardy. Each of those was the unprecedented moment of its day.

Then came Accenture. I watched cloud rewrite enterprise IT. Now I am watching AI do its version of the same thing.

None of it killed business. All of it changed the speed.

I have two Gen Z sons, and my 17-year-old is an artist who absolutely hates AI. We banter about it at the dinner table. His reasons are good and interesting, and I take them seriously. But every generation gets its “this is unprecedented” moment, and it rarely is.

Simpler Than You Think

Founders often point at the visible thing. Operators look upstream at where ideas turn into action, and where translation breaks. You spend your day looking forward; I spend mine looking sideways and behind. That is why I sometimes hear your problem differently than you do.

The founder with the availability problem? The break was somewhere upstream of scheduling and more about setting cultural expectations. The founder with the unmotivated sales team? The incentive structure rewarded the wrong thing. The founder who needed more managers? They weren’t being intentional about setting a staffing mix for their projects.

In every case, the answer was simpler than the symptom suggested.

The fundamentals are still the fundamentals. What changed is the speed of the cycle. AI is turning the dial faster than the last shifts. But *faster* is not the same as *new*. Your reflexes have to be sharper.

Founders who feel stuck are often just running an old reflex at a new speed.

The fix is rarely as hard as you are making it.

Not Yours Alone

The answer usually involves someone other than you doing part of the work. You may not yet have that person. You may have them and not yet trust them. Either way, you are not supposed to do this alone.

This is the quiet thing Collective 54 does well.

I did not see the pattern after one retreat. I saw it after three. I sat through dinners and overheard hallway conversations. I watched one founder describe the same problem twice, in different words. You cannot compress that onto Slack, and you cannot build it on Zoom.

The (always!) amazing accommodations set a scene. People relax, drop their pitch, and start telling the truth about their firm. That is when the patterns emerge and the answers follow.

You do not have to figure this out alone.

What To Do With This

The next time you find yourself stuck on something at your firm, try describing the problem out loud to someone who is not a founder. An operator, a trusted #2, or a peer, preferably while sitting around a bonfire drinking wine and making s’mores (my favorite part of last week’s retreat).

Whatever it turns out to be, it is older than your firm. It is simpler than you think. And it is not yours alone.