September 21, 2023

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Home & Commercial Expert

The 5 Tollgates of Selling Up-Part 1

“He’s clueless,” Alan said to his peer, Tracy as they walked out of the meeting.

Alan had gone into his presentation to his VP, Amir thinking it was in the bag. What in his mind should have been a slam dunk turned out to be 30 minutes of inquisition-like questions, debating of assumptions, and skepticism of his solution, all followed by a “We’re not going to do this.”

“I just can’t believe how out of touch he is,” Alan continued. “The solution is as plain as the nose on his face, and he can’t see beyond his own incompetence!”

Tracy was quiet as the two walked and Alan continued to sputter. After a few minutes, Alan couldn’t help but notice Tracy’s silence.

“What do you think?” Alan asked.

“How about we go in the conference room and chat,” Tracy said.

“Sure.” Alan had always respected Tracy’s judgment and how she commanded the respect of not just peers and followers, but also her management. The two went into the conference room, Alan shut the door, and they sat.

“Alan, you’re incredibly bright and very passionate about your work.”

“But… ” Alan said, waiting for the other shoe to drop.

“You haven’t yet mastered how to sell up.”

“Sell up?”

“That’s right.”


Let’s leave Alan and Tracy’s conference room chat for a minute. In my professional career I’ve had many opportunities to sell an idea to an exec. Sometimes I was successful in getting my idea sold, while other times I failed quite miserably. As I progressed in my career and sat more on the other side of the table, sometimes I bought what was being sold and sometimes I put the kibosh on it. Getting experience in both roles helped me better understand what both the exec and the person selling an idea go through and the barriers that can bog things down. I’ve locked on what I call “five tollgates” an exec goes through when being sold an idea. In full transparency, I did not do extensive research on the tollgates other than talking with several other execs about their points of view and corroborating it with my own experiences. What I have seen though, is a greater success rate in selling an idea when I create content that gets me through each tollgate in my pitch.

To explain the first tollgate, let’s go back to Alan and Tracy.


“What’s selling up?” Alan asked.

“In my experience there are five tollgates an exec has to make it through before he or she will buy into an idea and take action. Let me ask you a question, is this the first interaction you’ve had with Amir?”

“It is.”

Tracy smiled. “That explains things.”

Alan gave her a puzzled look. “What do you mean?”

“You never made it through the first tollgate.”

“What’s the first tollgate?”

“You never established credibility,” Tracy said.

“I didn’t?”

“No. In my experience, execs have to see you as credible before they’re willing to listen further. If you don’t have credibility with the exec and haven’t taken steps to establish it, you’ll likely not make it through the tollgate.”


Selling up tollgate 1: I believe you’re credible

An exec wants to know that you speak from an informed position on your idea. If you already have a reputation for being credible, you’ll likely have a low or nonexistent barrier to making it through this tollgate. If you’re an unknown entity with no preceding reputation, having good facts and data to demonstrate you know what you’re talking about will help you. The difficulty comes if you have a preceding perception as not being credible. While many execs will give people an opportunity to recover from a negative perception, they still will likely have a higher barrier that you will need to break through if you hope to make it through the tollgate.

If you already have a reputation for being credible, don’t worry about spending a lot of time convincing someone you should be listened to. If you’re an unknown like Alan or have a negative credibility reputation, then you’ve got to spend time with facts and data convincing the exec you should be listened to. A good tip that you haven’t broken through the tollgate is either getting repeatedly challenging questions about your idea or getting no reaction at all. This second one is tougher because the exec could just be politely letting you get through your spiel taking as little time as possible. The best sign that you’ve made it through the tollgate is getting a couple of questions that you respond to directly and candidly, with the exec acknowledging your answers and showing engagement in what you have to say.

The bottom line to making it through the tollgate is to get a good understanding of where you stand with the exec. If you’re a known and respected entity, then do a bit of show-and-tell that demonstrates you’ve done your homework. If you’re an unknown or clawing up from a deficit position, then you may need to place more focus on establishing your credibility before the exec will hear you out. If you’re not sure where you stand, talk to someone who knows you and has some exposure to the exec and have them coach you. It may seem like a bit of work up front but if done well can make all the difference in how your idea is received.

See The Five Tollgates of Selling UpPart 2.