My Worst Sales Call Ever

It was all my fault  — I earned it — and what I learned the hard way.

The Punch

“I’m not going to play that game with you. Tell me what you do or I’m heading back to the office.”

That was the CIO’s “red” line — before we’d even ordered lunch.
My confident plan? Gone. My jaw? On the floor. And somewhere in my head, Mike Tyson’s voice rang out: “Everyone has a plan until they get punched in the face.”

The Setup

A friend of mine — a golfing buddy and the senior leader at a Fortune 50 company — had pulled strings to get me a meeting with their Chief Information Officer. Big deal. High stakes. Perfect opportunity.

I was selling in a tough sector: mainframe IT and applications management. The company was a market leader with a challenging culture; however, my immediate team? Smart, fun, good at what we did, and always trying to be better. I’d been learning about consultative selling and was eager to try a people-first approach: talk about the person, not the product. Build rapport, ask thoughtful questions, and earn a second meeting — the ultimate sales win.

I brought my technical “wingman” along, dressed to impress, and felt ready to own the room. The lunch was at my club, my friend was there to show their endorsement, and I was sure this was going to be the start of something big.

The Crash

After a quick pleasantry, the CIO hit me with:

“Well, I’m here since you’re a pal of [my boss], and [they’ve] been bugging me to take this meeting forever.”

I tried to smile it off and opened with my big “consultative” question:

“What are you working on now, and what’s keeping you up at night?”

Silence. Then the knockout punch:

“I’m not going to play that game with you. Tell me what you do or I’m heading back to the office.”

Stunned, I froze. My wingman jumped in, skillfully explaining our product line while I sat there mentally counting down the minutes, hoping the valet hadn’t lost my car keys. My friend looked embarrassed. Lunch ended without further humiliation — but also without any hope of a follow-up.

Where I Blew It

Looking back, I can see the fatal flaws:

• I flattered myself that the referral gave me leverage.
• I didn’t pre-qualify or prepare for the conversation.
• I leaned too hard on my wingman instead of owning the discussion.

What I Learned

🦛 Do your homework — Research the company, the role, and the person in detail. No matter where the referral comes from, act like you don’t know a thing about the client.  Do your due diligence both at the organization, persona and person level. 

🦛 Pre-qualify — Have a short call with the prospect ahead of time to align expectations. I don’t know if the CIO would’ve agreed to a prep call, and you don’t know unless you ask for one.

🦛 Prep your questions — Write them down and make sure they serve the prospect first. My first question should have been along the lines of “What is the best way to make this time spent together most worthwhile for you?…

🦛 Control the room — Avoid extra attendees who might stifle candid conversation. If possible, respectfully ask your referrer not to attend. This provides a much better environment for candid conversation. 

🦛 Know your stuff — Be confident enough in your own expertise to lead without a “crutch.” Know enough about what you provide so you don’t need to bring the subject matter wingman with you for these high level connections.  (Plenty of time for the “SME” later) Trust me, as a coach, you can learn so much more and connect at a much deeper level. This will at minimum, establish trust, which helps get another meeting. 

Your Turn

Think about your last important meeting.

• What would you do differently?
• What did you forget?
• What would you like to forget?

And most importantly — did you check in with the prospect at the end to confirm you met their goals for the meeting? (This is the biggest miss I see from sales professionals today)

To close out your curiosity, there was no second call. Mistakes happen. Forgive yourself. Learn. And be ready for anything — so you can quickly pivot, get back on track with the right questions, keep your dignity, and avoid leaving lunch with a metaphorical black eye. Oh yeah, Hippos love dignity. 🦛

If you’re navigating change in business or life — especially the messy, high-pressure kind — let’s talk. Coaching through complexity is my specialty. Here’s where to start.