The best salespeople have expensive hobbies

I gave my “Sales 101 for entrepreneurs” lecture to the entrepreneurs at DreamIT Ventures in Philadelphia last week.  If you aren’t familiar with them, its a TechStars / Y-Combinator style incubator that helps launch great companies on a shoe-string.  It does so by providing a great environment and access to top notch mentors and experienced VC’s and entrepreneurs.  I was honored to be one of their speakers this year.

During my presentation, one of the entreprenuers asked me a great question:  What should I look for when I’m hiring a sales candidate?

My immediate response was, “The first and most important quality that I look for in a salesperson is that they have expensive hobbies.”  Of course, this evoked quite a bit of laughter, but then I started to explain my rationale.

Most people will tell you that when you hire a salesperson, you should look for confidence, persuasiveness, an extensive rolodex, the persistence of a 2 year old , and intelligence.  I say, yes all of those things are great (although I am not a believer in the rolodex-theory), but you are talking to salespeople.  We are not normal.  By nature, we are trained at the core to manipulate conversations, control the direction of conversations, get you to feel good about what we are saying, and convince you that the things you are looking for are not what you are looking for – but you are instead looking for the things that are good in us.  Our job is to close you – to get the deal done.

OK – so how do you find a good person, knowing that every person you talk to is trained to make you think they are a good salesperson even if they really aren’t.

I look for two basic qualifiers if I’m going to be thinking about this person further:

First, I look for expensive LEGAL hobbies.  (Obviously, I do not mean an expensive cocaine or heronie habit.)   I mean skiing, scuba, spa, golf, biking, expensive watch collections, expensive purse collections, etc.  These are things you can usually find out in the banter that happens even before the interview starts.  Expensive hobbies speak to two things:

  1. They have had some success before that allowed them to even partake in these hobbies
  2. They have motivation to repeat that success in order to continue with those hobbies.

You need to sense a passion for that hobby.  I don’t mean just skiing, but someone that has decided that they need to ski every mountain around Lake Tahoe more than once, and at least once on every continent that has skiing.  I don’t mean someone that enjoys biking, I mean someone that describes the bike they own (or REALLY want to own)  as having automatic transmission, disc brakes and made of titanium.  Its that type of passion for the hobby, that typically tells me that this someone who is driven, focused, and squarely thinking about cash in their pocket at nearly every turn.  The more this salesperson wants to do that hobby, the more she/he going to be thinking about closing.  This is of course, good for you.  The more your sales person makes… the more your company makes... the higher your valuation is… the closer you are to a great exit or break-even.

Second, a great salesperson will start building his/her pitch in the interview.   They may not get your product or the product direction correctly, but as they hear you talk about the product, they should come back at you with suggestions on how to pitch the product, or “have you tried this approach” questions.  These suggestions may be WAY off your corporate mission but that’s OK.  What you should take from this is that you have someone that knows how to listen, and is willing to take what he/she hears and be creative to find a solution.  The salesperson that is building his/her pitch the minute he starts hearing about the product is already thinking about how he/she can close deals.  This is the key to the entire thought process.  A salesperson that is thinking about a solution that leads to a close is the salesperson you want on your sales force.

As simplistic and as unconventional as these suggestions are, they are typically methods that have worked for me in finding great salespeople.  Of course, you should continue to look deeper into their background, sales tactic, etc. to see if its a match for your company culture, etc. but I follow these two simple rules to at least do a first pass at them.

Now to go plan that Tahoe trip….