Hire Weirdos to Create Outstanding Sales Teams

This post is not sugar-coated for political correctness or HR appropriateness. I work in the real world where prejudice, biases and unfair employment practices abound. Instead of pretending they don’t exist, so let’s deal with them head on.

I’ve built outstanding sales teams by following a few simple hiring principles:

  1. Hire weirdos.
  2. Hire people for their strengths.
  3. Build teams with diverse skills sets.

Hire weirdos.  Like me, and maybe some of you, weirdos don’t fit the typical Inside Sales Rep mold of most companies. This list below contains some common complaints about weirdos.

  • Introverted
  • Socially awkward
  • Too technical (or not technical enough)
  • Lacking sales skills
  • Too old (or young)
  • Overqualified (or under qualified)
  • Out of workforce too long
  • Too Black (Brown, Arabic, Asian, ethnic)
  • Not a “team player”
  • Too new to the company (or been with the company too long)
  • Gay (or too effeminate or too masculine)
  • Ugly (or short or fat)
  • Rumored to sleep around (or too straight laced)
  • Drinks too much (or doesn’t drink)
  • Has a criminal record
  • Too intellectual (or too dumb)
  • No degree (or wrong major)
  • Has family issues
  • Single (or married)
  • Has kids
  • Lives with parents
  • Been unemployed for too long

I have been implicitly or explicitly told to disqualify candidates from inside sales positions for each of the reasons above. However, I’ve got a soft spot for the underdog. I also owe the numerous mentors who gave me a shot when I didn’t fit the ideal profile. Plus I’m obstinate when I think I’m right.

Weirdos are quite aware they do not fit in. They’ve been passed over for promotions, given vague directions in performance reviews and are generally treated like outcasts.

When I hire I am looking for results. Period.

I want reps who will work hard to develop themselves, who will be honest with me and who will make the team around them better. If they do this, I can teach them sales skills, forecasting and our product lines.

Here’s what I look for when evaluating a candidate:

  1. Attitude and drive. Why do you want this job? What have you done to prepare for this opportunity? What will you do if hired to get up to speed?
  2. Aptitude/experience.  I’m looking for examples of the traits I need for role like determination, transferable skills from other roles, self directed etc. Sales experience in my industry is a plus but not a hard requirement.
  3. Character. This is tough to ferret out in an interview. It’s one of the reasons I like to promote from within the company because I can observe a person’s behavior over time to get an idea of their character. I like to see how they treat others and how they handle failure.

I’ve found that us weirdos are always grateful to be given a chance. We will work harder than everyone else to prove ourselves. We also tend to help others around us more, because we’ve been there in need of help. As an added bonus, weirdos often break sales records.

They will become the most loyal members of your team.

Here are 3 real-life examples from my teams.

The Wiz. The Wiz was in a customer servicy renewals sales role for over 5 years. He was perceived as argumentative with management, often didn’t make eye contact when speaking, swallowed his words a bit and had an accent.  He also was the only person I ever met who wore a cravat and a cabbie hat.

I was building a new inside team to sell a highly complex hardware product and invited the Wiz to interview. Why? Because I’d watched him work for a year in renewals. He was a bulldog when it came to digging up opportunities to cross sell new products to his customers. I also listened when he confronted management about new policies and programs that were being launched.  He wasn’t combative, he was passionate about his business and was unafraid to take a stand.  I figured I could coach him up on the softer skills and that he’d be an asset to our team.

At the end of his 1st month, his Field Sales teammates came to me and begged me to fire him. They called him “Mumbles” and told me he couldn’t pitch the product. They couldn’t believe I had hired him. I sat with him in 1-on-1s and spent many hours on the floor coaching him on telephone sales, how to listen for buying signals, pipeline management etc.  I told him that HE was responsible for learning this new product and that I’d taken a chance hiring him because I knew he could crush this role.  I also told him he was no longer allowed to sit down when on the phone. I made him stand up so he’d quit shrinking into his chair. This seemed to help him project his voice. (Plus it’s how I generated energy whenever I was pitching by phone).

1 year later, The Wiz had delivered over 200% to quota. The same Field Sales rep who had asked me to fire “Mumbles” called me and said, “I know you’re doing planning for next year…whatever you do pleeeease don’t take the Wiz off of our team.”.   The Wiz crushed his quotas for a few years and then was promoted into a different role.

Mr. Not a Team Player. Mr. NTP had left my company a few years earlier and wanted to return. I knew him as a sales rep who loved technology but who had difficulty with the softer skills of consultative selling. He was a cowboy who struggled with working in a team selling environment preferring to work solo. He also could check off another half dozen of the traits listed earlier. Neither my boss nor HR wanted me to rehire him.

I needed a strong willed technical rep for this position who could hold his own with an equally obstinate field sales rep. My inside rep also need to be a prospecting machine because the territory had been suffering from a lack of pipeline. I sat Mr. NTP down and explained in very clear terms that I had high expectations for him. If he joined my team, he would have to set the example for the team. In exchange, I’d spend as much time as needed each week coaching him on the softer skills that he needed. Probably the most helpful thing I did for him was let him meet with me whenever he felt his temper was going to blow. At first this was several times a week, but over time he became a model for the not only my team, but other teams on the sales floor.

Plus, he blew out his number for the next 4 quarters while getting us into a bunch of new target accounts.

The Mom was someone I hired for an Inside Sales role after she had taken a decade off of work to raise her kids. She had experience selling software but it was during the late 90’s dot com boom. She was about 20 years older than our typical hire. When I interviewed her, she sold me on her hustle, enthusiasm and how she planned to learn our technology and sales processes. I knew she could sell. She was also extremely competitive and determined to prove herself as not “over the hill”.

The first few months were rough. When she spoke to customers, she was a natural. But her product knowledge and lack of PC skills was brutal. She really struggled with Salesforce, email blasts and trying to sound technical on the phone. About 6 weeks in, I told her, “I need you to calm down and take control. Stop trying to be the technical salesperson and use your communication skills to have a conversation with the prospect about their business. If you get them talking, you will crush this.  I hired you because you know how to sell. Now you need to execute. If you cannot, I’m going to let you go before the end of the quarter. “

Well she crushed it. She learned to use conversation to qualify new prospects and then loop in her Sales Engineer for the technical discussions. She leaned on Sales Ops to develop templates and systems to make email prospecting and Salesforce documentation simpler. Plus she worked her ass off making more calls than anyone else on the team. In her first year, she was the #1 or #2 rep every quarter.

I’ve got dozens of stories like these. From the laid off tech worker to the rep struggling with serious health issues to the woman with the “bad reputation” and the college dropout.  My teams have always included at least a few weirdos.

I consider it a privilege to have had them on my teams.


If you want some help building your sales team or improving sales, contact me here. I’d love to hear from you. 

If you liked this article, please forward it to a friend, send me a note, comment, or like it on LinkedIn. 

Want more like this? Subscribe to receive new articles each week via email



Leave a Reply

Your email address will not be published. Required fields are marked *