August 6, 2026 //

Matt Andersen sat down with Authority Magazine to talk about what effective succession planning actually looks like and why most owners start it years too late.

Intro:

Most business owners think of succession planning as something that happens near the end. A document, a lawyer, a handoff.

Matt Andersen, CEO of Westlake Securities, sees it differently. In a recent interview with Authority Magazine, he makes the case that succession planning is inseparable from growth planning — an ongoing discipline, not a finish-line event. And the companies that treat it that way don’t just transition more gracefully. They’re worth more along the way.

The full interview is worth reading. Here are the parts we keep coming back to:

The problem most owners don’t see until it costs them

Andersen calls it founder dependency: a business built around one person’s relationships, judgment, and institutional knowledge. It’s common in the middle market, and it’s one of the most value-destructive patterns he encounters.

The cost usually shows up at the worst possible moment. He describes a company that came to market with strong financials and a real position in its space — and then buyers started asking about the leadership team. The answers were thin. Everything ran through the founder. That key-person concentration became a significant drag on value in the process, and it was entirely preventable.

The irony he points to: building leadership depth years earlier wouldn’t have just made the succession plan stronger. It would have made the business more valuable and more scalable long before a transaction was ever on the table.

This is the same dynamic we work through with owners in transaction readiness (the gap between what a business is worth today and what it could be worth with two or three years of deliberate preparation).

The five things:

1. Begin with the end in mind.

Start with clarity about the destination — what the organization should look like after the transition, and which values and standards need to survive it. Andersen describes working with a founder whose business had grown from $50M to $100M in revenue. The founder’s instinct was to focus on the financial outcome. Once the conversation shifted from *what can we get for it* to *what do we want this to become, and who carries it forward*, the entire process changed. Better outcome, and a better legacy.

2. Build leadership depth long before you need it.

The biggest mistake is waiting until a transition is imminent to develop the next layer of leadership. By then the options are narrow and the pressure is high. Identify high-potential people early, give them real ownership of real outcomes, and let them develop on a timeline that isn’t dictated by a deal.

3. Delegate with intention.

You can’t develop successors without genuinely letting go — transferring outcomes, not just tasks. Andersen describes a mid-market founder who stepped back from day-to-day operations and handed real ownership to his leadership team. Uncomfortable at first, for everyone. Within a year, people who had been order-takers were making strategic calls and owning the results. The business accelerated, and when transition time came, the bench was ready.

4. Make it cultural, not a boardroom conversation.

Succession planning that lives only at the top is fragile. Every manager is a potential successor to someone; every individual contributor is a potential manager. When talent development is built into the operating rhythm — accountability conversations, structured feedback, visible advancement paths — succession stops being an event and becomes a culture.

5. Address the emotional dimension honestly.

This is the one nobody talks about. For founders especially, succession can feel like loss, and unacknowledged, that weight causes leaders to delay or quietly undermine the process they started. Andersen describes a founder who’d built his company over nearly three decades and kept finding reasons to slow things down. The real issue turned out to be identity — the business wasn’t what he did, it was who he was. Reframing the conversation around legacy and what came next, rather than what he was leaving behind, unlocked one of the most graceful transitions Andersen has been part of.

Why this matters right now

The leaders and organizations who achieve the most, Andersen notes, aren’t necessarily the most talented — they’re the most consistent. That consistency is exactly what succession planning demands, and exactly what’s in short supply when a transition gets compressed into a few pressured months.

It’s also why timing matters more than it used to. A generation of founder-owned businesses is approaching transition at the same time, which means more companies competing for the same buyer attention. Owners who’ve built leadership depth will stand apart from those who haven’t. We wrote more about that dynamic in our piece on the Silver Tsunami.

Read the full interview here in Authority Magazine, August 2026

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Matt Andersen is CEO of Westlake Securities and the author of Completing the Deal and Intentional Growth. He speaks regularly to CEO and founder audiences — details on our Speaker Series page.

If succession or transition planning is on your horizon, our Intentional Liquidity and Sell-Side Advisory] teams work with owners years before a process begins. Start a conversation.