We’re in the process of interviewing sales candidates. When I started ranting about the mistakes they were making, Emily said she was “so glad” she didn’t have to interview with me. She was being sarcastic, I think, but we all laughed heartily. Except I was only laughing on the outside.
Before I get into that, let me explain where I’m coming from. It’s always important to hire strong people, but early on in a start-up it is absolutely critical. Think of it this way. If you are employee number three and you are not adding meaningful value, 33% of the company is not pulling its weight. If you are employee number 30 and you are not adding meaningful value, it’s only 3% of the company that isn’t pulling its weight.
There’s no hard and fast number where the need to hire strong people eases from critical to important, but this salesperson will be our 10th employee. That’s 10% of the company by bodies, and hopefully more like 33% of the company by sales production. Still critical, by my way of thinking.
Now that you know why it’s critical for Tim to make a strong hire, let’s talk about how the process is going. We’ve interviewed seven people so far. Some of them weren’t even qualified. That’s not the candidate’s fault – the recruiting firm is putting them forward as qualified candidates. But even acknowledging that the recruiting firm should take some of the blame, the candidates themselves are stumbling on the basics.
- Do your homework. FFS, read our website. Skim our social media pages. Know what you’re being asked to sell and to whom. Heck, go crazy and read up on our competition, think about the objections we probably get and how you’d overcome them. If you skip the homework, don’t be surprised when you fail the test.
- Bring your people skills. This one really surprises me because good interviewing skills go hand-in-hand with good sales skills. Be upbeat, have a plan, be a good listener, give straightforward answers, be prepared with good questions, don’t ask stupid questions. Holy slap-hand-on-forehead, please don’t ask stupid questions! Did you really just ask in your first interview if you can renegotiate the compensation? Or if you’re expected to work overtime?
- Highlight your strengths. Don’t just tell me you’re a good salesperson, tell me what makes you a good salesperson. Here’s a novel thought. Sell yourself the way you’d sell Simplifya. What’s your value proposition? Tell me how I should think of you relative to the other sales candidates, all of whom think they are good salespeople too. How will you close the deal?
My expectations are super high, I get it. I respect Emily’s opinion enough that I felt badly for the candidates. But then I thought, screw that, I don’t feel badly for them at all! In fact, they should be thanking me. Without me, one of them might have been hired only to later be fired by Tim because their poor performance in the interview translated directly to poor performance in the field. Better to not be hired than fired for sucking. You’re effing welcome. [drops mic]
Emily, I have no doubt you would have sailed through an interview with me. I cannot see you making any of the rookie mistakes above. And Dave, you obviously did sail through an interview with me. It wasn’t that hard, was it? Don’t answer that. Rhetorical question.
My point is these candidates are making it way too easy to say no, and that’s an especially bad trait for a sales person!
And really, my expectations are very reasonable. For talented people. Who are good fits for the job. And can demonstrate it in an interview. Without sounding like an ass. While drinking a beer. Okay, I guess my expectations are sort of high. 🙂

Ha! Great post, Rick!
Great article Rick! You should really think about, if not a book, then writing short stories. The way you write reminds me very much of David Sedaris’ work.
A Simplifya classic.