Sales Training Shouldn’t Be Dogmatic, Is Yours?

As I began building my first sales team from scratch at Felix in 2011 there was one thing that I wanted to make absolutely sure: I gave my reps every possible tool they needed to be successful.

I had a product that I knew very well how to sell. I also had a repeatable script that worked, clear product market fit, knew where to prospect the best leads and how to prioritize, and I’d been able to clearly train up other reps to do the same.

I slowly began to hire groups of 7, 10 and later 15 sales reps at a time and built up a large SMB floor. I made sure that I did all the hard work for my new reps, so they could step onto the floor and immediately be successful.

The old method

When new reps came in, I ran them through a rigorous training process that gave them all the product market and competitive information they would need to know. They had a script they were to learn cold and use for at least their first ~50 sales (after which they could stray slightly if they were so inclined). I supplied them with A+ leads, ranked them appropriately in their CRM and forbid from prospecting outside of their assigned leads to not waste time or duplicate territories.

Throughout their tenures, we had weekly and at times daily training where their managers or I would walk through group sales lessons/strategies, or listen to calls (“game film” as I called it) to dissect what was going well and what needed improvement in order to address those issues.

The result: we built a very successful sales floor. We had a machine that could take a rep from 0 experience and have them selling ~30 sales / month within 60 days. We had a sales team of 70 where the average rep on the floor was hitting around 2 sales a day, blowing away our competition.

Process vs. Creativity

But there was a problem that was becoming clear as we grew; the onus for innovation and improvement lay solely on my shoulders. In working so hard to make everything turn-key for my reps, I essentially killed the team’s entrepreneurship. If I didn’t tell them to do it, they didn’t need to know.

In fact, the system I had built indirectly “punished” reps for not staying inside the lines of the process we built, which I thought was for their own good. Thus, unless I explicitly gave a new direction, it didn’t happen. I foolishly trained and treated my managers similarly.

Moses Breaking Commandments MetaphorBy the time I had a team of 70 people behind me I was no longer able touch everything and be the single force driving change. I could not understand why people were not willing to take charge, try new things and help drive things forward.

Eventually, I realized the problem and worked to foster a spirit of entrepreneurship on the team, but at this point it was not easy. I had hired smart, creative people but I wasn’t getting the most out of them. I needed to relax many of my rules, which first led to some chaos, but later proved to be the right move. Upon digging in I found that my team was indeed unsatisfied with the old processes and ways. It was a job, and they could do it well, but it left them creatively uninspired.

Do’s and don’ts that I learned in the process


  • Create hard and fast rules / a process that everyone must follow
  • Incentivize effort metrics (sales is the only thing that matters)
  • Box reps into an exact script
  • Have the reps simply recreate YOUR process.
  • Underestimate the value of hands-on feedback sessions
  • Define set lead sources the reps can’t control
  • Stand in the way of reps failing (encourage failing fast and learning from mistakes)


  • Visibly and publicly track effort metrics (calls/meetings/demos). I suggest extremely visible scoreboards
  • Guide key talking points / value props reps should include in their pitches
  • Spend much time on Sales 101: How to think about closing; how to think about asking the right questions
  • Have rigorous “Game film” feedback sessions: guiding feedback on real-time sales calls or recordings.
  • Teach more to the psychology of sales than process. “Why rather than how
  • Incentivize pushing the limits

A new, semi-autonomous team

When I began building my next team, at Foursquare, I knew this lesson well. This time I consciously left some holes in the material. Even though I thought I knew better, I often left it up to the reps to learn the hard way. Rather than give them all of the answers, I worked to guide them to figure things out for themselves, course correcting when necessary.

Our training meetings were more of a socratic seminar, focused on asking the right questions, rather than lecturing. My team at Foursquare became better sellers, we were able to navigate in and out of many complex challenges and product changes and my reps were better suited to take major steps in their career–my ultimate goal.

I guess the moral of the story is one that I’ve known and lived by for some time: moderation in all things. Too much of anything, even a good thing like sales training, can often turn out badly. I’m cognizant of this now as I build my teams for the future based on this principle.

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