Specialists Versus Generalists

About this Video:

Selling a business isn’t just a financial transaction , it’s a personal transition. In this video, Josh shares a real story about a business owner who backed out of a sale just 10 days before closing because he wasn’t prepared for what life would look like afterward.

It’s a powerful lesson about the difference between specialists and generalists. Specialists are essential for executing complex deals, but they often focus narrowly on the transaction itself. Generalists bring the broader perspective — helping business owners think through identity, purpose, and life after the business.

When both work together, deals close and transitions succeed. When they don’t, even six-figure commissions and months of work can collapse at the last minute.

If you’re considering selling your business, this conversation might change how you prepare for the next chapter.

Transcription:

Here’s something that haunts me, a business owner I’ve been working with for six months to decide to sell his company. He hired a top M and A advisor, impressive track record, you know, the whole package.

First meeting, I explained my role. I helped with the transition side, the identity piece, making sure he’s prepared for life after the business.

The M and A advisor nodded along, but I could see the dismissiveness. The second meeting, I wasn’t even invited. I reached out. I think it would be really valuable for me to stay in the loop. The advisor cut me off. Josh, we need to keep things simple. Let’s just focus on getting this deal done and then you can work with them on whatever comes next.

Translation, stay away from my client, so I back off. The deal progressed terms were negotiated. Everything was moving towards closing. Then 10 days before closing my phone rang the owner in full panic mode.

I can’t do this. I don’t know what I’m gonna do after. Who am I if I’m not running this company?

I’ve been so focused on the deal. I never thought about my life after.

You can’t build a vision for your next chapter in an emergency phone call. 10 days before closing, he pulled out the deal. The M and A advisor lost their commission. Six figures gone. The buyer was pissed. The owner stayed stuck, and.

Everybody lost, and here’s what kills me. It didn’t have to happen this way. This is the difference between specialists and generalists. Specialists are essential when you need someone who knows how to structure a business sale. You want the person who’s done it hundreds of times.

But specialists see the world through a very specific lens, and sometimes that narrow focus means they miss the bigger picture.

That’s what generalists bring. We see the 10,000 foot view. We understand how different pieces connect. Think of it this way, a surgeon performs a procedure flawlessly, but your general practitioner helps you understand what life looks like after surgery, what rehab you’ll need, how this connects to everything else.

You know, both matter, but they matter in different ways. Here’s what makes a good generalist. We’re insatiably curious about how things connect. We’re constantly asking what are the second and third order effects that nobody’s talking about. We’re committed to lifelong learning, always reading, always talking to people in different fields.

Always trying to see what specialists might miss, and we’re actively looking around corners what’s coming that nobody’s prepared for. The M and A advisor was focused on closing the deal. They weren’t looking around the corner of the identity crisis that was coming. That advisor could have kept me involved.

We could have worked parallel tracks. By closing, the owner would’ve been stepping into a void. The deal would’ve closed, the advisor would’ve gotten their commission. Instead, their territorial protective disc costs them six figures.

You know, I’ve also seen it work beautifully. Another M and A advisor called me early in the process.

Josh, I can handle the transaction side, but I need someone to work with ‘em on the transition side.

So while they structured the deal, I worked with the owner on reinvention. What did he care about beyond business? You know, he’d always wanted to teach. What relationships needed attention. Well, he told me his marriage and his kids definitely needed attention.

So by closing, he was ready, psychologically ready.

Six months later, he was teaching entrepreneurship, had taken his wife on a month long trip and was having regular dinners with his kids.

Everybody won.

Here’s what this means for you. Get the best specialist you can find. These people are crucial, but also get a thinking partner who sees the bigger picture, and don’t let your specialist talk you out of the generalist when they say, let’s not complicate the things.

That’s exactly when you need both working together. Start the reinvention process way before you need it. Don’t wait until 10 days before closing to ask yourself what comes after.

Because here’s what I know. The specialists who are confident enough to recognize where their expertise ends, those are the ones whose deals actually close.

The ones who fight to keep generalists out, they’re the ones explaining why the deal they spent six months on, fell apart at the last minute.

You know, life’s too complicated to navigate major transitions without the right kind of help. And the right kind of help isn’t just one or the other. It’s both.

So what’s been your experience with specialists and generalists? Why don’t you know, let me know in the comments below. Oh, and by the way, thanks a lot for stopping by. I hope to see you back here really soon.