Before Selling, Ask 3 Questions

With tariffs, oil price volatility, and ongoing geopolitical tensions dominating the news cycle, many business owners are asking the same question: Is now a good time to sell? The answer depends far less on headlines than most owners assume.

A lot of people think that because of the things going on right now, it's a bad time to sell. But it's not necessarily those things in and of themselves that make it a bad time. Determining the right time is more complex than that.

Three things to align

Rather than focusing on headlines, owners should evaluate three specific factors before deciding to sell.

The perfect time to sell is when three things line up. The market is in good shape, your business is in good shape, and you personally are ready to exit. When all three are in place, that's the ideal moment. When they're not, the deciding factor usually comes down to readiness—yours.

There is one exception to the alignment rule: If you're miserable in your business, you should sell. Personal misery trumps everything else.

Three questions

Owners weighing whether the moment is right should ask three diagnostic questions:

1. Is your business in a state of decline, stability, or growth? Growth is the perfect situation for selling. Stable is less than perfect. Decline is not great.

2. Is the broader market buyer favorable or seller favorable? Am I selling my business in its current condition into an environment that is buyer or seller favorable or neutral?

3. How do you feel about running the business? When I wake up in the morning, am I energized to run my business? When I come home at night, am I excited to get away from it or eager to think about the day and celebrate the victories?

The third question is often the most overlooked, and the most important. Owners obsess over valuation and deal terms, but they underestimate the personal side of the equation. Many are blindsided by the loss of purpose and identity that follows an exit. That's why preparing yourself is just as critical as preparing your business. The grass may seem greener on the other side of the fence, but it's just as tough to mow.

Business owners have a significant purpose, one that can weigh even more heavily than family, hobbies, etc. When owners sell the business, they often lose that sense of mattering. To begin this conversation, it's important to determine where your strongest sense of purpose currently comes from.

Mark Herbick is the founder and CEO of Pursant, a middle-market advisory firm specializing in M&A, private capital market financing, transaction advisory services, financial leadership support, and business value enhancement consulting.