When Is the Right Time to Sell a Business? Three Questions Owners Should Ask

Photo by Ivan S, Pexels

With tariffs, energy-price volatility and geopolitical tensions creating uncertainty across the economy, business owners considering an exit may be wondering whether now is the right time to sell. But Mark Herbick, founder and CEO of middle-market advisory firm Pursant LLC, says the answer has less to do with economic headlines than with the condition of the business and the owner.

Herbick argues that the ideal time to sell comes when three factors align: the market is favorable, the business is performing well and the owner is personally ready to leave.

For owners trying to determine whether those conditions exist, Herbick recommends starting with three questions.

Is the business growing, stable or declining?

A growing company is generally in the strongest position to attract buyers, while a stable business may present a more neutral opportunity. A declining business, meanwhile, can be more difficult to sell on favorable terms.

That makes timing particularly important. Owners who wait until performance deteriorates may find themselves negotiating from a weaker position.

What kind of market are you selling into?

Economic conditions still matter, but Herbick says owners should consider whether the current environment favors buyers or sellers rather than simply reacting to the latest economic headline.

Tariffs, oil prices and geopolitical events can influence transactions, but they do not necessarily determine whether an individual company is ready for a successful sale. The business’s financial performance, industry conditions and buyer demand can ultimately matter more.

Are you personally ready to leave?

This may be the most important question of all.

Business owners often spend years preparing their companies for sale, focusing on valuation, financials and deal terms. Herbick says they can overlook the personal consequences of walking away from something that has occupied much of their lives.

For many entrepreneurs, their company represents more than a source of income. It can provide identity, structure, relationships and a sense of purpose. Selling can create an unexpected void once those responsibilities disappear.

Herbick works with clients to examine where they currently find their strongest sense of purpose, using a 15-question evaluation as a starting point for that conversation.

There is also one circumstance in which Herbick says waiting for the perfect market may not make sense: when an owner is deeply unhappy running the business.

Ultimately, Herbick’s approach suggests that selling a company is not simply a financial decision. Market conditions and business performance matter, but personal readiness can be just as important when determining whether it is truly time to walk away.