Timing a sale is a personal decision, but the pattern across hundreds of practices is consistent. The best outcomes — for the owner, the staff, and the clients — happen when a sale is planned two to five years in advance, not decided in a single frustrated weekend after tax season.
Four signals it is time to start the conversation
- The next busy season feels heavier, not lighter. When the workload stops feeling manageable and starts feeling like something to survive, the firm is telling you something about capacity and succession.
- Key staff are approaching their own transitions. A senior manager who is five years from retirement is a very different asset than one who is fifteen years out. Buyers price this.
- You are declining work you would have taken five years ago. That is fine — but every decline is quiet revenue erosion, and eroding revenue is a valuation issue as much as a lifestyle one.
- You have stopped investing in the firm. No new hires, no software upgrades, no rate increases. All rational choices for someone winding down — and all things buyers notice and discount for.
Three traps that cost owners real money
- Waiting for "one more good year." The last two years of an under-invested practice are often the years when revenue quality degrades most. Selling from strength almost always beats selling from fatigue.
- Assuming a successor will emerge. Internal succession is possible but rare, and it usually needs to be engineered years in advance — with a real buy-in path, real training, and real capital planning.
- Waiting for the "perfect" market. Market timing at a national level moves multiples modestly. The quality of your own firm at the moment of sale moves them far more. Focus on what you control.
What "starting the conversation" actually means
Starting does not mean listing, disclosing, or committing to anything. It means having one private conversation with someone who can help you understand what your firm looks like from a buyer's perspective — where the value is strong, where it is fragile, and what a realistic timeline could look like. Most owners we speak to are not ready to sell today; they are ready to think clearly about what a good sale would require, so that the eventual decision is on their terms.
The two-to-five-year window
The right amount of runway for most firms is two to five years. That window is long enough to shore up the value drivers that matter — client concentration, staff depth, workflow maturity — and short enough that the plan does not lose momentum. Any less and you are optimizing for a fast exit; any more and the plan tends to drift.