The best negotiators don’t rely on tactics. They rely on diagnosis, value creation, and discipline.
Over the past 25 years, I’ve had the opportunity to observe hundreds of negotiations across industries, companies, and deal sizes. Some involved multimillion-dollar contracts. Others were much smaller. Some ended with strong agreements that benefited both parties. Others deteriorated into battles over price.
When I was in my thirties, I never imagined I would be where I am today. I’m rebuilding my firm from the ground up, at sixty, around artificial intelligence. If you had told me back then that this is how my career would go, I’m not sure I would have believed you.
As founders build consulting and professional services firms, many eventually run into the same frustrating reality: the business is growing, but everything still runs through them.
We all know the rule: Nothing AI produces goes out the door without human review. The human in the loop isn’t optional – it’s literally how you avoid getting sued or losing clients.
But when was the last time you optimized that human’s ability to perform at their absolute best?
In Collective 54, we are growing, scaling and exiting our firms. Closing that final deal is a milestone. But capturing the value behind it is the real test that the deal was a good one.
Once the paperwork is signed, leadership has to integrate two organizations quickly, protect revenue, retain key talent and convert the deal thesis into operating results.
Many businesses point AI at the wrong target. They intend use it to trim costs and speed up the back office. Faster emails, cleaner reports, a little less headcount. That work is fine, but it does not make your firm worth that much more than it is today. A savvy acquirer can create cost savings pretty easily. What they cannot readily recreate is what you build on purpose to solve a specific problem, to meet a niche need. There is the shift worth making. Stop using AI to do your old work cheaper. Start using it to do work no one else can.
Early in my career, a client came to us with an idea nobody knew how to execute. My manager looked at it and said she didn’t have the time, but if I wanted to take it, it was mine.
The hardest conversation I watch founders walk into is the one where they finally decide to sell the firm they spent twenty years building. They have real revenue, a name people respect, a roster of good clients, and they expect an offer that reflects all of it. Then the buyer finishes diligence and the number comes back at a fraction of what they were picturing, or no real offer comes at all.
What the U.S. Army’s Workforce Study Reveals About the Future of Knowledge Work and What Business Leaders Should Do About It. The Question Most Companies Are Getting Wrong
Early in my career, I made a classic mistake. A coworker and I shared a stakeholder that was on the spacey side with a leisurely response time. We’d also share some stories and laughs related to this individual’s atypical antics. There was this one time that I got a reply from said stakeholder to an email I’d nearly forgotten sending. A reply which arrived almost a full month later.
