There are no guarantees in selling a company, except one — it won’t be a smooth process. Like running a marathon, selling a business is a long, often arduous, always challenging endeavor. All of that hard work is often rewarded; for marathoners, it might be a new personal record (PR), and for owners, financial gain or the achievement of another key objective. Nonetheless, like a runner, undertaking the sale of a business definitely requires the owner to have stamina, and to go into the process with eyes wide open, knowing that there will be bumps and bruises (and potentially breathless moments!) along the way.

That said, there are some common situations that almost always arise during a sale that will likely make the owner question whether or not they are making the “right” decision in selling their company. As such, it is important for owners to watch out for these stamina-sappers, but also understand that they are often temporary, and very common. With that in mind, owners should be prepared to have their endurance tested throughout the sale process, but also recognize that with a great deal of patience, confidence, and self-awareness, they will be able to go the distance and finish the marathon, i.e., complete a successful sale.

Marker #1 – 5K: The seller typically wonders if they have what it takes to follow through with a sale.
At some point during the transaction, a seller may feel anxious, become wary of the potential buyer, encounter difficulties with compiling the necessary documentation, and negotiations may be fraught with challenges and complexities. At this point, it is important for owners to tap into their stamina reserves and keep the finish line, aka their objectives, in their sights, but also proceed with caution if the conditions of the deal seem less than ideal.

Marker #2 – 5 Miles: The owner thinks the deal is moving too fast or too slow.
When selling a company, patience is a virtue. However, the owner may be “itching” to get the deal done so they can retire, move on to their next venture, pursue other interests or spend time with family. By the same token, they may feel that the transaction is moving faster than which they are comfortable, causing undue anxiety and stress. Like a marathoner, it is important to keep a consistent pace.

Marker #3 – 10K: The seller’s perception may not match reality.
It goes without saying that all deals terms should be in writing. However, there may still be an opportunity for miscommunication between the buyer and seller regarding perceived terms of the transaction. Thus, it is always better to ask for clarification during the negotiations than to live with regret at the closing or after the closing due to a misunderstanding that could have been solved through well-intentioned communication.

Marker #4 – 15K: It is common for the seller to question if they have negotiated a fair price and terms for their company.
A sizable portion of the owner’s net worth may be tied up in the business. As such, the sale of a company is not only a financial transaction, it is a personal one. Thus, the owner may believe that their company is worth “x”, while a potential buyer may think that it is worth “y”. However, owners who have undertaken proper preparations ( in advance of the sale, i.e., financial planning, determining fair market value, accounting preparations, etc., are more likely to be confident about their company’s valuation, which may help to mitigate some of their “worries” during the sale process.

Marker #5 – 13.1 Miles: The owner gets angry at their business advisor or the buyer.
Emotions run high during a sale, and it can be challenging for the owner to keep their feelings in check and bear in mind that cooler heads prevail, especially in moments when they feel like the deal is not going their way.

Marker #6 – 15 Miles: Someone who is not fully informed about the transaction starts advising the owner.
An outsider swoops in, flexes their “opinion muscles,” and suddenly, the owner goes into a tailspin. The owner questions the price and terms while forgetting that the person who is offering the “advice” is not actually “in the know” about the transaction. Here again, a level head and wise, informed counsel can keep the seller on an even pace to get the deal done.

Marker #7 – 20 Miles: At some point in the transaction, the owner will think that they are being taken advantage of.
Selling a business that has become such an integral part of their day-to-day life can be an emotional experience—almost like losing a family member. However, owners cannot let their emotions alienate a prospective buyer or dictate the terms of the transaction. On the contrary, owners must try to be as objective as possible while keeping their emotions out of their decision-making, before, during and after the sale.

Marker #8 – 20 – 26.2 Miles: The owner gets deal fatigue.
Every marathon runner fears that point in a race called “the wall” — when a runner’s physical and mental stamina are tested nearly beyond their limits. How a runner handles “the wall” can make or break their marathon time and whether or not they even finish the race. Owners may experience a similar point of fatigue when selling their company. The sale process is lengthy, and tests the owner’s endurance and stamina, along with their ability to “keep their head in the game.” When the owner hits “the wall” during the sale, it is important to keep their eyes on the prize and muster the patience and tenacity to see the deal through to the closing.

Inevitably, these eight challenges almost always occur during the sale process. However, sellers should remember that selling a business is indeed a marathon, not a sprint (or even a 10K). It requires a hefty dose of patience, an uncanny ability to silence self-doubt (or a trusted advisor who can serve as an ad-hoc therapist), and serious stamina to cross the finish line and get to a successful close. Like running a marathon, a company sale is not easy, nor is it for the faint of heart. That said, once the most grueling milestones are in the seller’s rear view mirror, the effort is totally worth it.