Getting your Trinity Audio player ready...

What 539 Executive Conversations Taught Me in 2025

Last year, I had 539 one-on-one calls with founders and executives of boutique professional services firms. From QBRs to onboardings to sales conversations and diagnostic readouts.

After that many conversations, one lesson stands out above the rest: the firms that thrived in 2025 were bold, and the firms that struggled played it safe.

The Barbell Pattern

We saw a clear split throughout the year. On one end, firms reported 20%, 30%, even 50%+ growth. On the other end, firms struggled extensively as their legacy models stopped working.

The struggling firms often had similar symptoms. Delivery costs had crept up. EBITDA/Profit was flat or negative. Some increased sales and marketing spend hoping to grow their way out. Others had accumulated overhead that made sense years ago but no longer fit. They often knew something needed to change, but hesitated or resisted.

The firms that grew had one major characteristic that stood out. They were bold. They adapted, pivoted, and experimented (especially with AI). They tried, failed, and tried again. They figured out how to make themselves and their teams more efficient. They acted before they had all the answers.

Where the Conversations Went

Five topics came up over and over again:

  1. How do we improve them? How are other firms using AI, even in simple ways, to make their teams more efficient?
  2. How do we generate more leads, referrals, and pipeline? What’s working for other firms right now?
  3. Founder Bottleneck. How do I remove myself as the constraint? How do I replicate myself and my team so we can scale? How do I work on the business instead of just in it?
  4. Who are we, what problems do we solve, and for who? How do we pick a niche and own it? We have a saying: “the riches are in the niches.” That couldn’t be more true than it is today.
  5. Is now the right time to sell? What do buyers want? For firms doing well, the market is hot and buyers are looking.

Drinking Our Own Champagne

At Collective 54 in general, we hear from hundreds of leaders and firms every year. That means we see what’s working, what’s not, and where the market is headed. It also means we need to hold ourselves to the same standard.

We kept telling members to get more efficient, experiment, and move fast. So we asked ourselves if we were doing the same.

The answer was: not enough.

So we started experimenting with AI throughout 2025. It started simple: call recordings, transcripts, and using AI to cut call prep and follow-up time for calls from 15-20 minutes down to 3-5 minutes. Small wins that added up.

But the bigger unlocks came when we embedded AI into our actual workflows. We built our own tools, assistants, and agents to help us analyze data, build account plans, and surface insights we might’ve overlooked. AI has better memory than we do. It can uncover gaps that stay hidden when you’re moving fast. It provides recommendations we wouldn’t have thought to ask for.

Two big unlocks for us: hyper personalization and hyper segmentation. AI lets us tailor how we engage with each prospect and member at a level that wasn’t possible before. It also helps us segment in smarter ways so we can provide more value in a timely way.

Our diagnostic onboarding is another good example. We have an assessment for new members that used to take about three hours to analyze, diagnose, prescribe solutions, build the deck, and prepare for delivery. Now it takes 30 minutes, and the insights are honestly better than my manual work. It frees me to focus on verifying the analysis, tailoring recommendations, and preparing for the conversation.

We’re using AI to help us think more strategically, make better financial decisions, and serve members in ways we couldn’t before.

What Didn’t Work

There’s a lot of noise right now with AI showing up everywhere in everything. It can feel overwhelming, and it’s definitely not a silver bullet.

We tried to do too much too fast. We attempted to connect systems that didn’t want to talk to each other and overcomplicated things in the process. We also realized that pivoting into this new era requires better communication and clarity.

If you’re feeling overwhelmed by the AI hype, you’re not alone. Start with the tedious, repetitive, low-value work and figure out how to hand it off to the machine. One task or use case at a time. Be intentional about it.

The Bet for 2026

We’re betting that AI is here to stay and that everyone’s role needs to evolve.

The shift we keep thinking about is that we’re becoming editors instead of creators. The machine generates the first draft, the analysis, the assembly. We refine, verify, and add what only humans can add.

In an ideal state, AI handles 80% of the tasks and leaves humans to do the things only humans can do: build trust, nurture relationships, exercise judgment, and make decisions that matter.

The Takeaway

Be bold.

Now is not the time to sit back and rely on the old ways of doing business. Things are changing, and we need to change with them.

The firms that thrived in 2025 didn’t wait for permission. They experimented, found ways to do more with the same team, made hard calls, and figured out how to increase output without increasing headcount.

The firms that struggled often had the same information but didn’t act on it.