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The Unexpected Quality Your Next Sales Enablement Leader Needs

Aug 21st, 2019

Question: What are the best two words a VP of Sales can hear from his or her sales enablement leader?   

Answer: “I disagree.”    

Seem strange to you? It’s absolutely true, and here’s why. 

Historically, when it came to sales and sales enablement/training working together, you had two very different archetypes:  

Vice President of Sales: A hard-charging, type-A, six-cups-of-coffee-before-10am executive with impressive VP of Sales hair. Doles out orders like a cantankerous drill sergeant.  

Head of Training: An over-eager professional who wants to do good work and make the sales team successful. Works tirelessly to deliver solid programs and works many late nights with little recognition. Hasn’t made it to the 6pm Pilates class in 3 quarters due to a never-ending to-do list. Has a hard time saying “no” — especially to the VP of Sales.  

What happens when you mix these two personalities together? Far too often, enablement professionals are far too deferential or even timid around sales leadership.

You want me to shadow every new AE’s first meeting? You got it! Redo the sales kickoff agenda two days before the event? No problem!

And therein lies the unhealthy dynamic which leads to poor decisions and inevitable failure. Heads of sales need leaders, not lap dogs, as internal partners.

That relationship dynamic should be a relic of the past. Sales leaders today should demand a head of enablement who has the respect, gravitas, and stature to disagree with them, because healthy debate and disagreement challenges both people to execute better.

Through my conversations with 300+ sales enablement professionals, the most successful and effective ones (at any level) are confident enough in their viewpoints to push back and ask challenging questions of senior leaders. When there are differing opinions, they (respectfully) fight for theirs.

When I speak to candidates who have failed, been fired, or in an untenable situation, 90% of the time it’s due to a poor relationship (or lack of any relationship) with their head of sales.

What can you do with this information?

  • If you’re a sales leader and you think you have an unhealthy dynamic with your enablement/training leader, let the person know that you expect them to speak up and encourage them to disagree with you. If you are genuinely encouraging of this and they still cannot find their voice, you may want to make a change. 
  • If you’re an enablement professional and you have a seat at the table, have an opinion – always. It should be a well-reasoned one and your own.  You will be wrong sometimes, and that’s okay. Remember: it’s better to be occasionally wrong than to always be “Switzerland.”

If you’re hiring a sales enablement leader, consider asking some version of the questions below of your candidates. Work hard to gauge the strength of their character.  If you’re mid-way through the interview and you hear the words “I disagree,” congratulations — you just might have found your next sales enablement leader.  

  • What’s an example of a time when you disagreed with your head of sales? What was the issue and how did you navigate the disagreement?
  • How have you established a dynamic with a head of sales to have a balanced flow of ideas and opinions?
  • When should you defer to a head of sales and when should you push back?

Dave Lichtman is the founder and CEO of Enablematch, a recruitment firm that specializes in sales enablement roles.

Want to learn more about what a great sales enablement leader looks like? Download Brainshark’s special report!