I talk to people every day who are trying to improve their career situation. Some are sharp and self-aware. Some are rusty but coachable.
And then there are a handful who quietly tank the process without even knowing they did it. Talented people—just sending the wrong signals.
If you’re reading this, you probably don’t do these things. But it’s still worth knowing what interviewers actually register, especially in software sales or customer success roles. Because you don’t get second chances in the interview game.
We met at a noisy Starbucks in San Francisco. I was hiring for a fast-growing SaaS company and wanted to talk to “Larry” about it. (Is anyone even named Larry anymore?) The conversation started out fine. He was smart, had the right experience, and had a quick mind.
Near the end, he decided to play a little game.
I was caffeinated, so I went with it. He started quizzing me on U.S. state capitals. No idea why. He kept a tally of my score and seemed to enjoy it when I missed answers. It felt like he was testing me, maybe looking for a little confrontational energy. I shrugged it off.
Later, I set up an interview for him with my client, who was a sharp, recently exited founder building his next company. The interview went well, until it didn’t.
At one point, my client mentioned the valuation of a company. Larry decided to challenge it. He pulled out some quick market cap math to prove it was wrong. My client, a financial expert, didn’t appreciate being corrected mid-interview by someone trying to get the job.
Things got awkward fast. Feedback wasn’t great.
Reflecting on it later, I realized Larry might struggle to get along with others. Maybe he needed to challenge people before he respected them. Maybe he was in the wrong profession. Maybe he’s a litigator now.
Interviewers aren’t looking to spar with you.
They’re trying to understand how you think, how you handle people, and how you approach problems. If your first instinct is to challenge the question, correct the phrasing, or critique how “most companies do it,” it doesn’t come off as smart. It comes off as risky.
Being right is not the point. Being easy to work with is.
When someone asks, “What are you looking for in your next role?” and you launch into your entire work history or a long tangent about compensation, it reads as scattered.
Answer the question. Then stop. Clarity and precision are underrated.
If you lead a team, this is especially important to watch out for. You’re used to advising, directing, and talking. Your team listens because they have to. The interviewer doesn’t.
Talking about your old boss, your company, or the market with a “this place is toxic” tone sends a signal. Everyone has stories. But if your lens defaults to blame, people worry you’ll bring that same energy to their team.
No one wants to hire someone who blames pricing, the product, leadership, their comp plan, their territory, their boss. You can be honest without being bitter. How you talk about the past tells them how you’ll handle the future.
Confidence is great. Entitlement isn’t.
If you start with ultimatums like “I need remote and a VP title or I’m out” before they’ve even decided they’re interested, you’re done.
Strong candidates ask sharp questions. They know their value. They collaborate until it’s the right time to negotiate.
Some of the highest earners I know reinforce their value through the entire process. They stay focused on what they bring to the table. They show, they don’t demand.
Interviews aren’t the place to itemize your full list of career wounds. Be real but keep it contained.
If you start venting about how undervalued you were or start quoting embarrassing things your boss said, it puts the interviewer in the role of caretaker, not decision-maker.
You can say something like, “I was ready for a more structured team, but the company wasn’t set up that way.” That’s enough.
Most candidates are qualified. What separates them is how they show up in the room. And once that impression is formed, it’s hard to change.
