Sales Bosses are representative of Sales 1.0: hire, train and manage to a quota. Fair exchange of money for work done.


Sales Leaders are representative of Sales 2.0: engage the sales person through personal connection and professional job satisfaction. Adapt one’s leadership style for the individual and treat them the way they need to be treated to harness their unique capabilities.


Great sales people are competitive and emotional; it is what makes them great. Logical management tactics (activity standards, closing ratios, pipeline) are no longer sufficient. Emotional management strategies (personal connection, tailored coaching, qualitative measures) take precedence. Like buyers, sales people have access to more information. A bad day or bad week can now result in a real time search for other options on LinkedIn or Facebook. Winners want to win; when they dont feel they are winning internally and externally they will look for a venue that can provide this.


Here are 4 trends from CSOs that are leading the way in this transformation:


  1. Risk Taking–Sales Boss says “we have never done that before; lets stick with what has worked”. Sales Leader says “fail forward and take calculcated risks to achieve the objective”. Promote a culture that celebrates failure. If people are not seeking failure by trying new things, your organization is not optimized. You are playing not to lose vs. playing to win.
  2. Creativity— Sales Boss says “just follow the playbook and you will be successful” Sales Leader says “push back and generate new ideas to serve the customers”. Teresa Amabile’s work at Harvard has continued to emphasize creative opportunity as a key lever in employee engagement.
  3. New Capability Acquistion–Sales Boss says “come to work, make your number, get paid and be happy”. Sales Leader says “new capability acquisition is the best predictor of future income”. And so the coach goes, the team goes. The best sales leaders we see are educating and investing in themselves. Leaders are teachers and teachers need constant education. You will never have an ‘A’ player leave and say “you over invested in me and taught me to much”.
  4. Progress–Sales Boss says “if you make your number, you are doing a good job”. Sales Leader says “quota is a lagging indicator and the number one leading indicator is daily progress”. Most sales people spend at least 65% of their day working. Nobody wants to run in place for more than half of their day. If people are making incremental progress they feel rewarded. This translates into feeling good about oneself and staying engaged over long periods of time.


Call To Action

Start your next sales meeting or employee 1 on 1 and ask your team how often they feel about the four points above. Don’t censor the conversation.  It might feel counterintuitive to do this; which is exactly why you should. It starts with you. Good luck!


Matt Sharrers

Studies and works with the top 1% of B2B sales and marketing leaders who generate above average revenue growth for their companies.

Matt is arguably one of the industry’s most connected, and physically fit, sales leaders. He “lives in the field.” As a result, he is the foremost expert in the art of separating fact from fiction as it relates to revenue growth best practices. Because of Matt’s unique access to the best sales talent, private equity investors tend to turn to him first when they need to hire remarkable leaders to unlock trapped growth inside of their portfolio companies. Matt’s recent engagements include work commissioned by private equity leaders Permira, TPG, Bain Capital and Hellman & Friedman.


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