April 25, 2017

Lessons Learned From 7 Encounters With Sales Leaders

Some people, by their actions, teach us what not to do as much as what to do.

really stupid business leaders

Sales leadership isn’t always the most effective it could be. Often times, B2B companies are focused on making sure the reps are good at doing their job, at the expense of making sure sales leadership knows how to do theirs.

Here are a few examples, real life, from my past, that might shed some light on the mistakes your own sales leaders might be making.


In a quarterly review for a multi-billion dollar software company, my VP asked us to reveal our forecast.  Most of us were pressured by the need to deliver our commit, the number we knew with 100% certainty we would deliver that quarter. One of the reps, when it was his turn, did 2 things that I will never forget:

  1. He gave a forecast of $500,000 when his pipeline in total was less than $400,000.
  2. He said that one of his deals was surely going to come in BUT that he wasn’t able to get the prospect to return his calls.

Sadly, while this rep was particularly stupid in is approach, this was not a singular instance of an innacurate forecast delivered as a result of moronic quarterly commit policies.  The company missed its earnings targets and took a huge hit to it’s stock price.

Lesson – Don’t pressure your reps into providing forecasts that are not reliable.  Create a sales culture based on reality so that reps don’t feel pressured into giving bogus numbers and saying stupid things like a deal is coming in when a prospect has gone underwater.

Cause vs. Correlation

One of my all time favorite encounters with stupidity happened while working for a small SaaS company.  The EVP of Sales determined, in his infinite wisdom, that a “Champion Letter” was a sales activity that resulted in the highest level of forecast accuracy and volume of deals closed.  For those that don’t know what a “Champion Letter” is, read Customer Centric Selling – but only the part about Champion Letters.  The rest of the book is relatively useless.

Basically, a “Champion Letter” is a follow up letter written to a prospect summarizing the results of a face to face meeting.  I stress, summarizing the results of a face to face meeting.  Why do I stress this?  Well, the face to face meeting was the actual metric that was directly contributed to a good forecast and the achievement of quota.  Sadly, each week, we had an actual “Champion Letter” QUOTA.  The results, instead of focusing on face to face meetings, reps faked “Champion Letters” to achieve the “Champion Letter” Quota.  When quarterly reviews were conducted the EVP was stumped as to the cause of such bad performance against revenue quota when all the activity quotas he set were being met.

Lesson – Make sure you are not contributing to the inefficiency of your sales team by not understanding the difference between cause and correlation.  Additionally, make sure you don’t higher senior sales leaders that use stupid formulas to mask hidden incompetence.


I once had a meeting with an EVP of Sales to discuss a sales strategy I had created allowing Reps to use private video hosting to stop selling blind.  We opened up the meeting by me asking him to tell me more about his sales team.  He told me that the reps on his squad were amongst the best he had ever come across in his years in sales.  The words he used to describe his team were “Tier One A Players”.  When I asked him how he was going to enhance their performance in the coming year, he indicated that he had contracted with a sales trainer.  The sales trainer’s primary goal was to help the team of “Tier One A Players” learn how to construct emails that clearly stated value. 

Lesson – Don’t spend money fixing a training problem that is most likely a recruiting problem.  Hire sales people that have basic reading and writing skills and spend your training dollars teaching them to understand why customers buy your stuff.

Cold Calling

This story comes from the exact same discussion and exact same EVP as revealed in the story above.  When I asked him what the number one problem was with his team of “Tier One A Players”, he responded that they were not cold calling enough.  Having waited about 20 minutes to respond, I pointed to the phone on his desk and asked him if he answers it when people call.  His exact response, “I never answer that phone. I don’t even know why it’s on my desk.

cold calling doesnt work resized 600

Lesson – If you are an executive that doesn’t answer the phone, chances are you are not in a unique fraternity.  While I do believe Cold Calling has its place, and does work in certain circumstances when done correctly, it really is an outdated strategy and one that should be replaced with more cost-effective marketing and sales strategies.


I worked for a very large software company and covered an industry vertical that resulted in literally every consultant that downloaded a whitepaper from our site and in my region getting passed along to me as a sales lead.  The result was that I missed a real lead because it got lost in a sea of leads that were really not leads.   It got back to the CEO that I missed the real lead.  He conducted an investigation that forced me to reveal to my General Manager why I had missed the real lead.  My answer was not only logical, it was the truth.  I was getting inundated with too many false leads.  The CEO’s answer, very simply, we need to hire more sales reps to handle all the leads.

Lesson – Don’t pay marketing for lead quantity.  Pay marketing for lead quality.  You’ll save yourself a boat load of money by not hiring sales reps to cover leads that don’t exist to pursue a market that doesn’t exist.


One of the absolute best software sales reps I knew applied for a job at a very large software company.  The job was for a Regional Mid Market Account Executive with a focus on the manufacturing vertical.  He was conceivably the most qualified person for the job that existed in the states that make up New England.  Not only that, he was good friends with the hiring VP.  He never made it past go.  Why?  He failed the test put together by the recruiting organization. 

Lesson – Hire talent NOT exam results from exams that measure all the wrong things. 

Customer Referrals

It should come as no surprise to business leaders that referrals are one of the best sources of new business.  Even knowing this fact, most do a terrible job making the referral process more systematic.  I had a call with a director of marketing and a sales manager for a young company.  They wanted to learn more about my sales strategy using private video hosting and how I could help them prospect more effectively.  Very quickly I determined my program was not a good fit.  I played along for a few more minutes and asked if they currently had customers.  They said yes, hundreds.  I said do you have a reference/referral program in place.  Both answered confidently, NOPE, not yet. 

Lesson – Before hiring the folks that are going to lead your marketing and sales team make sure they have their priorities in order.  Make sure they know that focusing on your current customer base and make them all Net Promoters will work wonders in solving many of your current prospecting problems.  If you don’t know what a Net Promoter is, google it. You probably have Net Promoters and don’t even know it.


I know I may come across as bitter in this article. The truth is, I am bitter. I am bitter because I had to endure over 9 years of hell at the hands of people who were paid a crap load of money to have a clue.

In the end, while articles of this type might turn you off due to my sarcastic tone, what I am sincerely trying to tell you is this. Sales leadership matters. If it is done well, your sales organization will soar.



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