Why Most Owners Start Succession Planning Backwards

This is Part 1 of a three-part series distilling George Hartman's Owner Playbook succession session. This part covers why most owners approach succession in the wrong order, how much runway changes your strategy, and the four dimensions of readiness. Part 2 covers the business, financial, and personal readiness diagnostic in depth. Part 3 covers finding a successor and making the handoff work.

George Hartman has spent more than 50 years in financial services — as an advisor, a national dealer CEO, and for the last three decades, a coach to hundreds of advisors working through some part of a business transition. He closed FindBob's Owner Playbook summer series with a premise that runs against how most owners actually approach succession: the deal is the last chapter of the story, not the first.

Most owners start at the wrong end

When practice owners begin thinking about succession, Hartman's experience is that the first question is almost always "what's my business worth?" — followed immediately by who's buying, how they'll get paid, and what the tax consequences look like. Those are legitimate questions. They just come far too early.

A strong succession plan, in his framing, follows a different order: first build a business that can operate and retain value without depending entirely on you; then get yourself ready, financially and personally, for a future where you're no longer in control of everything; then identify or develop the right successor; then deliberately transfer trust, relationships, and authority — and only then does the transaction itself happen. Most owners start at the transaction and work backwards. It can still produce a sale. It doesn't reliably produce a successful succession, which Hartman defines as a good outcome for you, your clients, your team, and your successor all at once.

Time is the resource that gives you options

How much runway you have changes what kind of planning actually makes sense. Ten to twenty years out, Hartman calls this the "inspiration" stage — there's time to be strategic: build enterprise value, reduce dependency on yourself, develop younger talent, strengthen systems. Five to ten years out, it shifts to "perspiration" — more tactical and intentional work on your financial needs, your role during and after the transition, and whether an internal successor is realistic. Three to five years out is "desperation": decisions about your successor, deal structure, and timing all become urgent, and it's also the danger zone — by some research, roughly half of first succession attempts run into serious trouble or fail outright, which can cut an already-short timeline in half. And one to two years out, Hartman only half-jokingly calls "hallucination," because you can't manufacture a trusted successor overnight, remove twenty years of founder dependency in a few months, or build an enduring team culture before a deal closes.

Four dimensions of readiness — and a weak one drags down the rest

Hartman breaks succession readiness into four areas. Business readiness asks whether what you've built is actually transferable — can clients, staff, revenue, and service quality survive a change in ownership. Financial readiness asks whether you know how much money is actually enough, and whether you're quietly counting on the sale price to make the numbers work. Successor readiness asks whether there's someone capable of owning and leading what you've spent decades building, and whether clients have had time to trust them. And personal readiness — the one Hartman spent the most time on — asks whether you're truly ready to let go of the identity, structure, and status the business provides.

Weakness in any one area constrains the others. A highly profitable business with no one ready to take it over isn't succession-ready. A great successor and a strong deal don't help if you keep moving the finish line emotionally. The transaction itself doesn't fix these gaps — it just exposes them.

Continued in Part 2: a closer look at business, financial, and personal readiness — including the hidden cost of founder dependency, why your real number might surprise you, and why "ready to sell" isn't the same as "ready to leave."