How to Interview Sales Reps – Building your bullshit Filter

In case you’re reading this because you’re hiring for sales, and your idea of a great salesman is DJ Trump, then stop reading here. I got nothing for you. 

“WTF? The dude’s clearly a genius salesman – he sold the whole country the idea that he’s who they need!” 

Exactly. The only commodity Trump has ever been able to sell – himself. He is exactly the rooster you’re trying to weed out of your interview process. 

Bear with me…

The Hardest Job in Business

“The hardest job in business” I always call hiring sales reps, only half-jokingly. 

In my experience, there is a large pool of people out there who have perfected just one skill – how to act like a rock star sales rep in an interview situation. 

In other words – how to sell themselves to an electorate of one.

Don’t get played. The wasted cash you will pay out in recruitment costs and base salary before discovering the truth and setting them free again isn’t even the real damage. It’s the opportunity cost – The sales you could have booked in that period if you’d been able to identify a principled, hard-working, skilled sales rep the first time. 

How can I avoid being Trumped?

Interviewing is the worst method for choosing a sales rep. But if I can’t rely on personal observation or a recommendation from someone I trust, I’m stuck with it. I can’t give a sales rep a coding challenge like I can when hiring engineers. I sometimes introduce a role-play sales call, but its often counter-productive because it plays straight into the hands of the talented play-actor. 

The Meta-Interview

Here’s the recipe for my current disinfectant I use to cleanse my shortlist. 

Don’t listen to them, watch them. Look and listen for clues that they may be playing a role. Take them out of their comfort zone – be creative here. Watch how they react to unexpected, left-field questions. Ignore what they’re saying – their sales pitch, no matter how compelling. They are undoubtedly just telling you what you want to hear. 

How hard are they trying?

I usually learn about 5x more from the questions a candidate asks than from the answers they give. 

  • Do they ask thoughtful, original, knowledgeable, questions?
  • Do they consider your answers and ask follow-up questions for clarification or to get more details? 
  • Or do their questions seem rehearsed, stock questions?
  • Or do they not ask questions at all until you ask them if they have any? 
  • How well did they get to know you and your needs, goals, and priorities by the end of the interview? 

After the Interview

Give them some homework on your business or market to research for the 2nd interview.

Don’t call them back after the interview.

  • Do they follow up after the interview? How – by email or phone?
  • When they chase up multiple times, do you feel awkward or can they relax you? Do you feel pleased to see their number come up on your phone or does your heart sink?
  • How do they react to objections?
  • How do they take disappointment? To being brushed off?
  • Do they wait for you to call them, or give up, or start to sound disgruntled at not being courted? 
  • Or can they maintain an amiable, professional demeanor and see it as an opportunity to take the initiative and manage the remainder of the process?

What I’m Looking For

During all of this, I’m trying to determine where they rate on the factors that I’ve found to be key indicators of sales success:

1. Integrity

This is #1. Without a pass here, Do not pass Go. 

Any indications that they have a moral “gray zone” when trying to close sales is a flashing red light. If this comes out in an interview situation where they are presenting the best version of themselves, I guarantee it will become an issue in practice. I have zero tolerance for such players, as I also have for people who think I’m being naive because all Sales involves some lying. It doesn’t.  

2. Workrate

Are they going to do the hard yards? The 300 dials they may need to make every day, to get 30 productive calls a week, to secure 5 meetings a week, to get 5 POs a month, to make quota. 

Do they want to come work hard for you? Why? How do you tell?

Here, the only relevant data is: What evidence have you seen or heard that they have done this in the past? 

Or do they exude entitlement? Perhaps project that they feel they’d be a star signing for you? 

Workrate is my #2 factor. It’s often overlooked entirely when I’ve watched others interviewing for sales roles. The experience, the style, the market knowledge – none of it matters if they don’t have this. 

3. Empathy

Ignore any feeling that they connected with you, that can be achieved using grooming techniques. We’re all susceptible to flattery and mirroring. 

Look instead for evidence of the productive use of empathy:

Do they ask lots of good questions?

Did they find out your buying criteria?

Did they find out what results your other sales reps are getting?

Did they influence your priorities toward key strengths they’ve highlighted needing in their career?

Are they persistent without becoming irritating, pushy, or whiny?

4. Experience selling into your target market

Having this experience is more useful than not having it, but I find its vastly overrated as a predictor of performance, and can seduce you into missing out on a great candidate who has been selling in a different vertical. 

5. Skills and techniques

These can be learned, so they are useful, but at the bottom of my list. 

I know I can take someone who ranks highest on criteria #1 to #3, because they can quickly learn or expand on #4 and #5

Red herrings – Things often valued that are not worth a fuck

Relationships, or the size of their “Rolodex” (ask your Grandad)

Every sales rep with several years of experience in your target market will hold up their extensive contacts and deep relationships as their USP. It sounds superficially compelling – “ooh, look, we’d get a sales rep and a load of hot new leads!”)  In the last 20-odd years I can’t recall a single case where a new sales rep closed a deal with a customer they had brought along in their address book. This isn’t how Sales really works. 

He/she “…looks the part”, “…has gravitas” or “…is a heavy hitter”.

These depressingly common phrases are usually a subconscious bias for “…looks like me/…looks like people who play businessmen I’ve seen on TV/…is a good-looking white male”. Fuck that shit. Call it out if you ever hear it. 

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