“This is a big price tag,” Rhonda said as she looked through Tom’s proposal.

Tom didn’t expect the resistance he was getting from Rhonda, his organization’s vice president. Tom had just been promoted to manager of a small team and was in it to make a splash in the organization. He unveiled a bold proposal to implement new enterprise software that would replace an existing system that had been in place for several years.

“Yes, it’s a high price, but this is leading-edge technology that will help propel us into the future. Our current system uses old technology that will be obsolete. Now is the time to act.”

“But what we have is working and stable,” Rhonda said.

Tom’s frustration grew with Rhonda’s resistance. “Yes, today it’s working, but what about tomorrow?” Tom asked.

Rhonda looked at her watch. “Tom, we’re just about at time. Let me give you a bit of coaching.” Rhonda was big on cultivating her staff and used situations like this as teachable moments.

“Um, OK,” Tom said.

“I love your passion and creativity. Those attributes will serve you well as you progress in your career. Do you want to know where you missed the mark on this proposal?”


“You presented a solution without a problem.”

“Well, I… ” Tom stammered as he flipped through his slides.

Rhonda stood up. “It’s not there, Tom. If you want to sell on a solution you’ve got to clearly articulate the problem you’re trying to solve. Give it some thought, OK?”

“I will. Thanks, Rhonda.”

“Take care,” Rhonda said as she left the room.

Selling up tollgate 2: I acknowledge the problem

Once you’ve made it through tollgate 1, I believe you’re credible, you now have to convince the exec that a problem exists. This is where objective facts and data take center stage. The key here is balance. If you come off like the black and white opening scene in an infomercial with a person feigning utter disgust while trying to peel a potato, then you’re going to be viewed as jaded and will undercut your own credibility.

Also key to explaining the problem is articulating the consequences of not addressing the problem. When an exec not only understand what the problem is but also has a clear picture of the tangible consequences of not addressing it, you’ve accomplished both explaining what the problem is but why it’s important to address.

So what about if what you’re trying to sell isn’t a problem that needs fixing but an opportunity that needs to be seized upon? The approach is no different. Support the opportunity with objective facts and data and explain the consequence in terms of what happens if the opportunity isn’t pursued.

As with tollgate 1, look for positive engagement from the exec. Confrontation on the problem statement could mean you haven’t convinced the exec there’s a problem, and silence on the exec’s part could be a sign of disinterest.


Execs live in a world of problems to solve, and constantly have to decide which problems to pursue and which to leave on the back burner. If you want your exec to take action, you have to convince him or her that there’s not only a problem, but it’s one worth pursuing. Next time you propose a solution take the deliberate step to clearly articulate the problem you’re trying to solve.

We’ve gone through two tollgates thus far:

Next up is part 3 of The 5 Tollgates of Selling Up.

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