Unforced Errors Make Selling More Difficult For You

The salesperson was deep into the sales conversation with his prospective client. He was talking with the primary stakeholder within the company, and they were progressing towards a deal. At some point, he asked his contact how the company would typically procure a solution like the one he was offering. The contact described their process, mentioning that the CEO would sign off on the deal.

The salesperson, working hard to bring the deal in on his timeline, decided to go over the main contact’s head and had his Vice President of Sales reach out to the CEO directly by email, copying both the Account Executive and the main contact.

The VP’s note was polite. He started by introducing himself, even though he wasn’t involved with any of the prior conversations, then he summarized the AE’s solution and expressed how excited they were to be partnering with the client. He even offered to postpone the project’s start date until after the client’s peak season, while still honoring their Q3 prices (a 25% discount) and securing a spot with their onboarding team. Finally, he ended his email by asking the CEO if his AE could send a new copy of the order with a start date after Q4, “hoping this is a win” for the client’s business.

Going Over Their Head

Context matters: a good or desirable decision in some circumstances can be a big mistake in a similar scenario. In this case, the salesperson and his VP were on track to win the deal, right up to the point that the VP emailed the CEO. The solution they offered was a relatively simple software process with a price tag under $20,000. It was an important decision for the main stakeholder, but it didn’t come close to anything that would command the CEO’s time and attention. As a good leader, the CEO would have signed off on the deal. But he would also allow his manager to decide what he needed and what solution he preferred. The CEO would never see or use the solution, nor would he be willing to participate in a transactional decision, one with little downside risk.

There is nothing wrong with trying to pull revenue and results forward in time. There is, however, a lot wrong with being impatient in a deal that you’re highly likely to win in short order. By going directly to the CEO, the salesperson and VP betrayed their desperation to capture the revenue now, something the CEO recognized as weakness, and which eliminated their ability to negotiate effectively. The problem with believing that you need to compel a client to change now is that when there are no real consequences for waiting two weeks or even 90 days, your attempts to speed up your revenue can work against you.

The Unforced Error: Selling Over Email

There are too many people who think they can sell effectively over email, mistakenly believing that they can gain commitments using an asynchronous medium. But sending a sales email means taking yourself out of the very conversation you want to have with your prospective client, something that is especially true if you are a leader. In this case, the VP should have picked up the phone and called the CEO directly. He would have earned more respect and he would have given himself a chance to make a pitch. You make it difficult for C-Level executives to treat you like a peer when you send an email instead of picking up the phone and calling them directly. Because you don’t believe you deserve their time, neither will they.

On a phone call, the VP could have told a different story. He could have easily said that his company was decimated by the global pandemic and that it would help him if the CEO could pay for the solution now. He could have admitted that they were way off their goals, even though they were winning new clients, and asked what he could do to provide the prospective client even greater value. Alternatively, he could simply say that his company was working well with the manager, and that even though this deal probably doesn’t require the CEO’s time, he wanted to make sure the CEO had a contact who would ensure his team succeeds with the solution.

The warning here isn’t about going over your main contact’s head, per se. Sometimes you need to throw a Hail Mary pass into a crowd and see if you can’t win the game. But selling is hard enough without making unforced errors, mistakes that you could have easily avoided.