I made the CTO look stupid (and lost $227K)

I lost a $227K deal because I made the CTO look stupid.

This was (obviously) not my plan. But... my whole pitch was built on how much better my product was than the system they were already running.

Slide after slide, I laid out everything that system couldn't do, everywhere it fell short, every reason it was holding them back.

Here's what I didn't know walking in: their CTO had championed that system. He'd helped design it, pushed to get it approved, implemented it, and kept it alive for years.

And there I was standing in front of his team explaining, point by point, why the thing he'd spent years of his career on was the problem.

He was polite. The deal died after that. 

What I wish I would have known then: 

Every system you're trying to replace has an author. And the author is almost always in the room.

Someone chose the incumbent. Someone fought for the budget and the renewals. Someone put their name on it and has been owning it since. When you say "this system is broken/outdated/inefficient" that person doesn't hear a product critique. They hear "you were wrong, and now everyone knows.

A person defending their reputation will never be able to see or hear you clearly. They see a referendum on their judgment. (They will win that referendum. It's their house.)

So now, when I help teams displace an incumbent, here's what we do differently:

1. Find the author before you pitch. Ask your champion: "Who originally brought in the current system?" Now you know who you need on your side.
   
   

2. Make the old decision look smart for its time. "That was the right call for what you needed then" hands the author an out. The situation changed, not their judgment.
   
   

3. Sell the change in the world, not the flaw in the system. The company grew. The market moved. The requirements got heavier. The system didn't fail, it just wasn't built for where they are now. Same outcome, completely different feeling in the room.
   
   

4. Let the author co-own the upgrade. Make them the person who spotted the next move, not the one who got caught backing the old one. People support what they get to be the hero of.
   
   

5. Never win the technical argument at the cost of the human one. Being right in the room and losing the deal is still losing.
   
   

None of this means softening your product or pretending the incumbent is fine. You can be completely clear about why you're better. You just take into account the human element (which exists whether you acknowledge it or not). 

Try this week: before your next pitch against an incumbent, find out who chose it.

One question to your champion: "Who originally brought in the current system?" Then build your pitch so that person can say yes without admitting they were wrong.

I learned this one the expensive way, I hope you don’t have to! 

Hit reply and tell me: have you ever lost a deal you should have won because of one person in the room?