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Resolve the roadblock, not the symptoms.

I had been working on the largest deal of my life for around eight months. It was between two Fortune 100 companies. My CEO had already discussed the deal with the other company’s CEO, and both were on board with the broad-brush strokes. Every week, I had my CEO and three VPs checking on its progress. For better or worse, I was in the spotlight. Everything was coming together until it fell apart.

I got an email. The customer, someone I considered a colleague, said ‘this isn’t happening’, went on to explain why, and then sincerely started to apologize, as he wanted to see it happen as much as I did. It was a disastrous situation. One that would stain my years’ results and probably my reputation for some time. I reached out to a good friend and asked for advice. I explained the situation and everything that was said. At the end, my friend paused and said ‘You know, the guy never said no. He just said it was not happening for XYZ reason.’ We got back on the phone together with the customer and asked a bunch of questions to try to understand the underlying reason why his decision makers no longer wanted to go forward.

After we understood the reason, I emailed our VPs and explained what was happening and what it took to fix the underlying issue. Once our CEO got word about the situation he instantly solved the customer’s underlying concern. The deal then closed six weeks later to my managers’ surprise.

This story is not about closing a deal. It is about working with other people and figuring out solutions. Here is what I learned:

  • When situations are marginal, it is often not because someone doesn’t want something to happen. It is often because someone does not know how to solve what they need to solve to move forward.
  • If you ask questions and figure out the underlying roadblock instead of the symptoms you might be able to remove the roadblock for both sides.
  • Ask for help when you need it and never be the only one holding the grenade when it goes off. Mistakes are not about the wrong outcome happening. Instead, mistakes are about mishandling a situation and rarely does it make sense to go it alone.

Every month I am presented with opportunities that seem unlikely. When I believe in something, I bet on the person I have been working with and will go to great lengths to help them solve the problems they are trying to solve. Not everything ends up materializing into a tangible result. I often do surprise people with partnerships, sales, and product innovations that others didn’t think would ever come together, though. Through the process, I also build trust and friendships that matter a whole lot more in the long run because people know that when things get sticky, I’ll stick it out.

My advice, double down when the situation is marginal and resolve the underlying roadblock.


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