Why leapfrogging IT is the fastest way to kill a deal
From the Other Side of the Desk

There’s a surefire way to go from “potential vendor” to “never call again” — and that’s bypassing the IT department and going straight to our leadership.

It’s not bold. It’s not strategic.
It’s disrespectful.

Here’s What Happened

I once had a vendor cold call me multiple times. Each time, I made it clear: We’re not interested. I was polite, firm, and professional.

Then one day, my boss called and said, "Hey, come over for a minute".
I walked into the conference room and there they were — that same vendor, sitting at the table with a big smile and a pitch deck.

They had gone around me.
Over my head.
Straight to my leadership.

Now, not only was I forced to sit through yet another pitch I had already declined — but I had to do it in front of my boss, who had no idea we’d already said no a dozen times.

It goes without saying that vendor went on my mental 'do not buy' list.

Why This Doesn’t Work

Let me be perfectly clear:
Going over IT’s head doesn’t increase your odds of a sale.
If anything, it ensures the opposite.

Local government CIOs and IT directors are not gatekeepers — we’re strategic advisors to leadership. And when someone tries to cut us out, it raises red flags:

• Are you trying to hide something?

• Do you not understand how procurement works?

• Will you do this every time there’s a conflict?

You don’t earn influence by undermining trust.
You don’t win projects by playing political games.
You win by building relationships — the right way.

Takeaway for Vendors

Want to sell into government IT? Here’s the golden rule:

Respect the process. Respect the org chart. Respect the people who actually use your product.

Because if you go around us to get your foot in the door, don’t be surprised when it’s the last door we ever open for you.