Perhaps the most important questions in any enterprise sales campaign.  Early in my career I learned the hard way the cost of getting this question wrong.

I was running a major deal, the biggest of my year. It was very competitive, but we felt quietly confident.  We had the CIO covered. We had his peers and directs covered.

But I’d 𝗺𝗶𝘀𝘀𝗲𝗱 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴.

There was an individual contributor in IT named Eric. He was two managers below the CIO.
Brilliant, a bit awkward, not part of the formal evaluation. We’d met him once or twice and didn’t think much of it.

What I didn’t know was that this was the third company where he and the CIO had worked together (don’t judge me – there was no LinkedIn in those days 😱). The CIO wasn’t deeply technical, and Eric had become his go-to person for anything with technical risk. A low key but trusted adviser.

So at the end of a tight evaluation process, when the CIO had to make a call, he asked Eric.

And Eric didn’t recommend us.

Maybe a competitor got to him. Maybe he just preferred a different approach. We never found out. What I do know is that they won the deal and I lost it, and missing this critical relationship was a big part of why.

So, when mapping power the org chart matters. It tells you who owns the decision and who carries the formal authority. You can’t ignore that.  But it’s not enough.

The real risk lies in the things you don’t know yet. The hidden relationships. The people with history and trust that aren’t showing up in your stakeholder map. The confidant a leader leans on when the stakes are high.

Most sellers understand the idea of “informal influence.” The trap is thinking you’ve already found all of it.

In my case, I’d done a good job mapping the obvious power in the deal. I just missed the one relationship that ended up mattering most. And that was enough to sink it.

So take your time. Ask more questions. Look for the connections that aren’t on the chart. Always assume there are gaps in your view. Because all it takes is one unseen line of influence to change the outcome.

Tough lesson. One I never forgot.