Sales Coaching Collision – Old School Meets New School

By David Szen on Jul 19, 2016

4 Minute Estimated Read Time

At a recent workshop I engaged in a conversation involving three parties, each from a different generation. Representing Generation X, I approached a Baby Boomer Sales Manager and a Millennial Seller discussing the ideal amount of activities required to fill out a “robust” pipeline. It quickly became clear that the Manager did not feel that the Seller was getting in front of enough prospects. This seemed to be exacerbated by the fact that the Seller continued to adamantly define her position that her networking and research would eventually pay off in a way that aggressively canvasing a market would not. It was clear that she very much believed in the idea of quality over quantity.

There are a few important details to understand that will provide context to this situation.  The Millennial Sales Rep was responsible for selling to middle market companies - companies with less than $100 million in annual revenue within various markets.  These are fairly lean target companies where a traditional approach to reaching decision makers can typically be used.

From the perspective of the Baby Boomer Sales Manager, the Millennial Seller was not working hard enough to get her foot in the door. Even once she had gained access, the Manager didn’t feel as though she was being aggressive enough in getting higher and wider within the organization.

From the perspective of the Millennial Seller, she did not want to waste time making cold calls when she could do good research and target the right decision makers at the right companies. Her approach was laser focused, and the concept of throwing darts just to meet meeting counts seemed like a waste of time and effort.  Additionally, she felt uncomfortable with how pushy the whole process felt as she tried to gain a foothold within organizations that she ultimately deemed to “not be a good fit.” 

I quickly realized that we were headed for a collision. On the one hand, we had a Millennial Seller who had a certain expectation of what it meant to be in Sales; she had never been taught how to engage a prospect without feeling pushy.  On the other hand, we had a Baby Boomer Sales Manager who was only focused on the numbers and not on building the skills required to do the job. The Millennial Seller may have, at one point, contemplated a long-term career in sales but now was very seriously reconsidering if this was the best fit based on her style and needs. 

The Baby Boomer Sales Manager’s frustration over activity levels clouded his ability to see the great coaching opportunity right in front of him.  The old school “numbers game” philosophy on prospecting collided with the new school challenge of an untrained, yet eager-to-prove-something, Millennial Seller.  The reality is that both of them were right – but for very different reasons.

In order to remedy the situation, each school, old and new, needed to accept the reality of what they were collectively trying to achieve.  Why?  Because the Millennial Seller could learn that Sales can be a lucrative and fulfilling career, while the Baby Boomer Sales Manager could teach the critical skills that are necessary based on his experience and may even learn something new along the way.

Here are some great ways to break through the opposing schools of thought and drive results.

  1. It’s all About the Math – The Millennial Sales Rep and the Baby Boomer Manager have an aligned need – to increase sales. Attain the right numbers of suspects, prospects, appointments, opportunities and activities in order to drive eventual results. Illustrate the math that proves the results and set expectations accordingly.
  2. Set Realistic Expectations – Setting the bar high enough to push the Millennial Sales Rep is a good idea. Setting the bar too high will be discouraging and create a demotivated Seller.
  3. Be OK with Being Proven Wrong – Allow the Millennial Sales Rep to explore the variables that define what it means to be a more qualified target. She clearly believes that quality over quantity is a much more efficient approach. Until proven, she should be required to hit activity targets but give her the flexibility to shatter the status quo of activity generation and proper pipeline management.
  4. Hold Frequent Check-ins – The Millennial Sales Rep is going to appreciate an open dialogue so that performance can be assessed along the way and tweaks made as necessary. A once-a-month “check-in” will feel like a slow death to a Millennial Sales Rep. These conversations can be informal or formal but will need to happen frequently.
  5. Establish Peer Coaching – The Millennial Sales Rep may benefit from gaining the perspectives of others who have been successful. In some cases, however, having the Seller talk to a more experienced Seller may hinder the process more than help. They want to learn from people in the same situations – and age group – and they don’t want to feel judged.  Encourage peer networking and collaboration – many Millennials prefer to learn this way.
  6. Observe and Recommend – The Millennial Seller may need skill development on prospecting and early phase selling. This means that the Boomer Sales Manager needs to invest time listening, observing and assessing what needs to be coached.  The Sales Manager can’t expect results if the skills are not in place.

We expect that the clash between the old school and the new school will continue to plague many sales organizations.  With that being said, there is a huge opportunity for organizations that are able to harness the eagerness associated with this next generation. With a bit of flexibility and a desire to help set realistic expectations, Managers have the ability to form a new generation of sellers. We have seen on many occasions that these Sellers are passionate, and most feel a strong desire to prove their value. If given the autonomy to prove their perspectives, they will either shatter the status quo or learn valuable lessons along the way. Seems like a win-win to me.

Multigenerational Sales Team Pocket Guide

For more reading on generational impacts in B2B sales, see our book The Multigenerational Sales Team, as well as these related articles:

David Szen

Written by David Szen

David Szen is a contributing author for Symmetrics Group and a sales effectiveness expert. Having delivered numerous sales and leadership training programs for companies across industries, David understands the nuances that can impact sales team performance. David explored generational impacts on sales team effectiveness and co-authored the book The Multigenerational Sales Team with Symmetrics Group's founder Warren Shiver.

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