Treat Every Sales Rep Differently

I Don’t Treat All My Reps the Same.

I’ve written about how important it is to always be recruiting for All Stars, to hire weirdos, and how to interview to build teams with diverse skill sets.

Today I want to talk about how I treat each of my employees differently by focusing on their strengths and by not rewarding everyone equally.


Focusing on Strengths

When I was first promoted into management, I didn’t know how to be a good manager so I read a bunch of books to see what others recommended. One was “First Break All the Rules: What the World’s Greatest Managers Do Differently” by Marcus Buckingham and Curt Coffman. I chose this book because the title appealed to my inner contrarian.

This book introduced me to the concept of managing by amplifying strengths vs. working on weaknesses.

Upon reflection, this idea made sense. Up until that point I had always focused on becoming a better employee by working to improve my own weaknesses. As a new manager, I was attempting to do the same with the reps on my sales team.

After reading this book, I began to realize that the reason I had been successful throughout my career was because I had leveraged my strengths.  I was self-directed, ambitious, a fast learner, a good listener, adept at applying technology to solve business problems, and had a bias for action. My weaknesses included public speaking, social/business networking and data analysis. I could now see how doubling down on my strengths enabled me to quickly move up the ranks from sales to management. I also realized that despite having worried about and worked on my public speaking and networking skills for several years, I’d barely improved in these areas.

It was a relief to make a deliberate decision to continue to push forward doing what I did best and to stop trying to improve my weaknesses.


I next thought about the reps on my sales team.

  • The Hustler was our team’s #1 sales rep. He was a stereotypical career field salesman. He would take customers out to golf, for drinks, invite them to dinner at his house, and would become friends with them. At trade shows and events he was a natural – making introductions, meeting new people, and having a great time. He had a limited understanding of our technology, but would somehow always manage to pull someone more savvy in to help anytime he needed to “talk tech” with his customer. The Hustler was very money motivated. He avoided paperwork, technical discussions, and the office when possible.
  • The Consultant was my favorite rep. I had promoted him from Inside Sales to Field Sales and was grooming him as my future replacement in management. He used a consultative sales approach similar to mine. He would present a logical businesses case backed by solid technical reasoning. I could put him in any business situation and have confidence he would deliver. The Consultant was highly motivated to move up in the company. He liked being given extra responsibility and being seen as a leader on the team.
  • The Storyteller had been the Top Rep on our Consumer Sales team and had been promoted onto my B2B Sales team several months earlier. In Consumer Sales, his customers loved him. Most were computer novices who were just getting online for the first time. They’d talk with him about kids, cooking, art, and movies. He’d ease their worries about technology, would show them how to use email, and made them very comfortable buying from him. He was also a highly focused and organized volume seller. His days were booked with calls, opportunities and fielding many referrals. The Storyteller was a people person. He wanted everyone to like him and enjoyed being recognized as the Top  Rep.

Obviously (in retrospect) everyone on my team had different skills and motivations. As a new manager I hadn’t realized the importance of taking these into consideration.  Instead I tried to manage everyone exactly the same way – the way that I liked to be managed. And I tried to teach them to sell the same way – the way that I liked to sell.

I was not being an effective manager. This was frustrating everyone on my team.

  • In training sessions and team meetings, The Hustler grew bored immediately. He would get this glazed look in his eyes and start yawning, which in turn made me angry. He also wandered into work late, took extended lunches, and I suspected he was skipping out early on Fridays to play golf while the rest of us worked late in the office.
  • The Consultant was frustrated that The Hustler outsold him every Quarter. He said, “How can The Hustler be beating me? He’s shows up late, is out of the office all the time and doesn’t even understand our technology that well!”
  • The Storyteller just couldn’t grasp Commercial sales. He didn’t understand our product positioning, he struggled to speak coherently about our technology, and he wasn’t adept at pulling in resources to help. The other reps didn’t respect him and complained that he was “not cut out for our team”.

I decided to try a new approach by focusing on maximizing & amplifying the strengths of each rep. We’d work on their weakness just enough to bring them up to the minimally acceptable level. 

I met with each rep to come up with a plan.


With The Hustler, we focused on leveraging his relationships. His mission was to discover when startups were being funded, learn when budgets were expanding at his existing accounts, and to work his connections for introductions to other target prospects. He even leveraged his network of contacts to get “inside information” to help us win opportunities the other reps were working.

To address his need for technical pre-sales help, I teamed him up with a dedicated Sales Engineer. The Sales Engineer presented at technical meetings, did white boards, answered technical questions, and designed solutions for the Hustler to sell.

I also stopped hassling the Hustler about his office hours. As long as he delivered over quota, he’d have full autonomy to control his schedule.

The results were extraordinary. The Hustler exceeded quota every quarter for the next 2 years and closed 3 record setting deals. He was in the office less, but when he was there he was an active participant with our team or he was working though the specifics of closing a deal.

He thrived under this approach.


With the Consultant,  we focused on moving him from a pure sales role into a team lead role with both sales and management responsibilities. I started including him in management meetings, asked him to lead part of our weekly sales team meeting and assigned him to mentor our new hire. Since he was taking on these additional responsibilities, I increased his base salary and reduced his quota to less than the other reps.

He did so well with this, that when we created a new team to sell into Enterprise, he joined it as the Team Leader.


With the StoryTeller, I realized I had made a mistake promoting him into a position where he could not succeed. This is a common mistake that is discussed in First Break All the Rules.

We had a long talk. The Storyteller was earning less money, felt like a failure, and was stressed out all the time. He said dropping from Top Rep to the Worst Rep crushed his morale. What made this even worse was he felt like there was no way out of this predicament. He was trying his best but just not getting it.

I pointed out how successful he’d been in Consumer Sales.  I explained how the skills that worked so well for him there didn’t transfer over to B2B Sales. I told him that our company needed people like him in Consumer sales and that he wouldn’t be looked at as a failure if he returned there. In fact, it was my failure for promoting him into this position where he was a bad fit.  Reluctantly, he agreed to return to Consumer Sales. Within a few weeks, he was the Top Rep once again and was happy he’d made the change.


As for myself, I made a conscious decision to focus on my strengths as well.  My first priority was to expand our team. This this time I deliberately sought people who weren’t like me but brought diverse, complementary skills to fill in where we had weaknesses.

  • I hired a former Pizza Shop owner, who became a strong sales rep but more importantly, taught me how to interview by digging for examples, numbers and details.
  • I hired a former elementary school teacher who was highly-organized and data driven. She researched, evaluated, and implemented our first CRM supporting across 25 employees across a multi-state territory so that we could manage our pipeline and forecast accurately.
  • I hired an aggressive, hungry, cold calling rep to bang out prospecting calls and set appointments for our senior reps so they could focus on Consultative Selling and less cold prospecting.

For the next several years, I accepted that I wasn’t going to become a great public speaker, that my social networking skills would remain minimally acceptable, and that I would get the highest return by focusing on my strengths.

Initially these strengths were hiring the right people and teaching them how to sell effectively. Over time, my focus expanded to to building and managing high-velocity Inside Sales organizations.

I never did get much better at networking and I still don’t really enjoy business social events. However, for the past 20 years, I’ve I hired people who excel at this and leverage their strengths instead.

As for public speaking, years later I made a concentrated effort to improve here because it was such a key area for me in senior leadership roles. I have definitely improved past the minimally acceptable level.  I’d like to think my audiences have appreciated my efforts. At the very least, they aren’t yawning and tuning out as much.


I Don’t Reward Everyone Equally

Some people value money, some value recognition, some want time, some want flexibility, some value autonomy and others prefer well defined tasks. How do I know what someone values?  I ask them. I listen to them. I observe them.

Here are some examples:

  • The Super Technical Guy became our team’s hardware specialist. Anytime we launched a new product or feature, he was assigned to learn the product, train our reps and then be our in-house go to guy for tech questions.
  • The Hard Charging Frat Boys were assigned to Hunting Roles because they simply were not turned off by “No”.  They also were our unofficial Happy Hour hour organizers so I gave them a a weekly expense budget and let them run it as they saw fit.
  • The Money Motivated rep worked his way up to a Closer role and was never promoted into management. He loved the money and self-sufficiency this provided.
  • The Father with 3 little kids was able to arrive later than everyone else and work through lunch so he could drop his kids off at school in the morning.
  • The Night School Student was able to take off early on Wednesdays so he could get to class on time and worked a flexible schedule when finals came around.
  • The Mother was able to work from home when her kids were sick. (I’ll be doing a full post on Working from Home and Remote Employees soon.)
  • The Rapper was assigned to cover the West Coast because he worked clubs late so getting in to our East Coast office around 11AM was ideal.
  • Many Reps were given quota relief, extra help, or time off when going through family difficulties like deaths, illnesses and other crises.
  • My Entire Inside Sales Team was allowed to leave early every Friday for a year.  This team delivered over and above every quarter. By late Friday our customers had gone home, the reps were fried, and everyone would be catching up on administrative work. I am confident that giving them an hour off a week paid for itself 10x when they stayed late to close deals, worked all night at end of quarters, and scrambled when we needed to cover big deals that slipped out.

Although this has been a long post, it all comes back to applying 2 simple concepts that I apply when treating every employee differently:

  1. Focus On and Amplify Strengths (and don’t work on weaknesses)
  2. Don’t Reward Everyone Equally

If you’ve been frustrated trying to change your sales reps or if your sales team is not generating the revenues you need, applying these concepts might change your success rate or even shift your entire management approach.

It did for me.

Happy Selling.

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