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Leading a Four Generation Sales Team w/ Kelly Riggs [Episode 482]

Every generation has its differences – what do you do when you are asked to lead a team across four of them?

Kelly Riggs, Creator of the Business Locker Room, author of Quit Whining and Start Selling, speaker, podcaster, and Co-Founder of Counter Mentors, joins me on this episode.


Kelly describes Counter Mentors, founded with his son Robby. A counter mentor brings the values of Millennials to Boomers in the workplace. The goal is an environment where both generations thrive, using the wisdom and skills of each.

Between Boomers and Millennials are Gen X; after Millennials are Gen Z. Silent Generation members are still going strong In some companies, for five generations in one office.

Gen Z grew up in the 2008 economic downturn, so they care about economic security. They are more entrepreneurial than Millennials.

Over a year ago, Millennials became the largest population of the workforce. Boomers are retiring. Gen X are not ready to retire.

Digital kids entering the workplace suddenly had to learn interpersonal skills. Millennials and Boomers both want respect, but their definitions of it differ. Millennials want their bosses to earn their respect, but respect goes both ways.

Boomers need to approach Millennials from a leading position, but not from an authoritarian position. Be tolerant of questions, and be willing to explain the reasons. Don’t categorize any generation as being problematic.

Millennials don’t see the Boomers as the revolutionary youth they were in the 1960s and 1970s. The generations have some commonalities. Each generation was raised differently. Each can be effective in the workplace, working together.

In many companies Millennials are in leadership over Boomers. Leadership is harder than they thought! But they can do it.

Millennials may see Boomers as hypocritical. People leaving an organization leave because of the people they work for. People promoted to leadership have not been trained as leaders. They become micromanagers, and drive people away.

Management is not the same as leadership. The role of a manager is largely administrative. They know the administration, and the CRM, but not the key aspects of leadership. They have not learned to coach.

Invest money in training sales leaders, or pay the price in missed quotas and turnover. ‘Calls per day’ does not relate to identifying the right contacts to call.

Kelly learned his processes from the books of the masters. A coach needs to see each salesperson, with their strengths and skillsets, and guide them in those directions.

The Sales Enablement Podcast with Andy Paul was formerly Accelerate! with Andy Paul.