I bombed my first sales interview. Badly.

I bombed my first sales interview. Badly.

The kind of bomb where you know the interviewer is only continuing the conversation to be polite.

I was wearing an oversized "suit" I’d bought the day before at Kohl’s, sweating through it after driving 30 minutes in a car with broken AC and black leather seats in the middle of a Texas summer.

I couldn’t “sell this pen.” I fumbled every sales question they threw at me.

Think of me as the political equivalent of a technical nerd interviewing for an IT sales job. I knew the product of politics better than most pundits—walls of books at home, a political blog, talk radio junkie. But I was also introverted, a bit nerdy, and my answers were probably awkward.

Not exactly what you’d put on the target profile for your next top salesperson.

But I won the job on that technical expertise. The VP at the time thought my political nerdiness might be more of an asset than a liability in sales.

He was right.

Over the next decade, I channeled that passion for the product, learned the craft of sales, and went on a run: President’s Club multiple times, one of only two people to hit quota every single month for three consecutive years, and the highest revenue-per-call average on the national sales team.

Same introverted, nerdy guy. Nothing about my personality changed. I just learned the skill—and had deep conviction for what I was selling.

And that’s exactly what most business owners miss when they hire.

When most business owners hire a salesperson, they're drawn to the candidate who lights up the room. The one who's great in the interview, has endless energy for conversation, and seems like they could be anyone’s best friend in 30 seconds.

The extrovert.

And I get the logic. If sales requires networking, discovery calls, and building relationships—it makes sense to think the most outgoing person is going to close the most deals.

Surely extroverts make better salespeople than introverts, right?

But I've watched this assumption play out hundreds of times now, and it’s costing business owners a fortune.

Here's what I've observed: extroverts and introverts both have natural strengths in sales. But they also have blind spots—and it's the blind spots that kill deals.

Take a networking event. An extrovert walks in and thrives.

They talk to 30 people, hand out business cards, have great conversations, and walk out energized. The event itself felt productive because the act of connecting with people is inherently rewarding for them.

But here's where it gets tricky: the rewarding part and the productive part aren't always the same thing.

Having 30 conversations feels like a win. But if none of those conversations turned into a qualified opportunity with a clear next step—it was just activity.

An introvert at that same event is there on a mission. They're not particularly enjoying the small talk, so they're constantly filtering: Is this person a real business opportunity? If not, I need to move on. They may leave drained—but they leave with three qualified contacts and follow-ups already scheduled.

The same dynamic plays out in discovery calls. I've watched extroverted reps run out of time in meetings because they spent 20 minutes building rapport through personal conversation. Great for likability. Not great for uncovering whether there's a real problem to solve, budget to address it, or urgency to act.

Meanwhile, the introverted rep walks into the same call with a mental checklist: seven to ten things they need to walk out with. They're intentional, methodical, and they don't mistake a fun conversation for a qualified deal.

I'm not saying don't hire extroverts. Some of the best closers I've ever worked with were extroverts who learned discipline.

That's the key word: discipline.

An extrovert who builds discipline around their natural energy is a force. An introvert who leans into their systematic tendencies and doesn't let discomfort hold them back is equally dangerous.

The problem isn't personality type. The problem is when business owners hire based on energy in an interview instead of process in execution.

If you're hiring salespeople, stop asking yourself, "Do I like talking to this person?" and start asking:

Do they have a system for turning conversations into qualified opportunities?

Can they articulate the difference between activity and progress?

Do they measure success by outcomes or by effort?

Those questions work regardless of whether someone recharges at a cocktail party or on their couch.

Here's what I've come to believe after 25 years in sales: your best salesperson is the one who treats it like a craft—someone who studies it, practices intentionally, and iterates on what works.

That person might be the loudest one in the room. Or the quietest. That’s not the test of who’s going to close more deals.

But if you're consistently hiring for personality and wondering why your sales numbers are stuck—look at your hiring criteria. You may be hiring on assumptions that simply aren’t true.

Adios,

Ray

PS — I'd love to hear any questions or feedback you have. Drop me a comment here.