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On this episode of the Sales Gravy podcast, Jeb Blount (People Follow You) sits down with Leigh Cantrell and Rob Matura who are Regional Vice Presidents at Cigna to discuss the keys to leading multi-generational sales teams. It’s a fascinating conversation in which you’ll learn about the challenges and rewards of building sales teams from diverse age groups.

Challenges With Leading Multi-Generational Sales Team

Leading a multi-generational sales team can be challenging. The differences in values, work styles, communication preferences, and technological competencies will stretch you as a leader. These challenges include:

  1. Different work values: Different generations may have varying work ethics and priorities, making it difficult to align everyone towards common goals.
  2. Communication differences: Younger generations may prefer digital communication, while older generations may prefer face-to-face or phone conversations.
  3. Technological competency: Younger generations may be more familiar with technology and digital tools, while older generations may require additional training and support.
  4. Different learning styles: Different generations may have different preferences for how they learn and receive information, making it challenging to provide training and development opportunities that accommodate everyone.
  5. Resistance to change: Some team members may resist new technologies, processes, or ways of working that are introduced to the team.

To effectively lead a multi-generational sales team, you must adapt to these differences and foster collaboration, communication, and teamwork across generations.



The Strengths of Multi-Generational Sales Teams

The good news is that multi-generational sales teams bring a diverse range of skills, perspectives, and experiences to the table. This  leads to numerous strengths over teams that lack this level of diversity.

  1. Diversity of ideas: Team members from different generations can bring unique perspectives, experiences, and creative approaches to problem-solving and decision-making.
  2. Range of skills: Different generations bring different skill sets and competencies to the table, such as expertise in different technologies or a deep understanding of traditional sales techniques.
  3. Mentorship: Older team members can provide mentorship to younger team members, while younger team members can bring help their older team members embrace new ideas and tech.
  4. Flexibility: A multi-generational sales team can be more flexible and adaptable to changing market conditions, customer needs, and technological innovations.
  5. Increased customer understanding: Team members from different generations can help the team better understand and connect with customers from different age groups and backgrounds.

By leveraging the strengths of multi-generational sales teams, you will quickly increase sales and deliver better numbers.

Seven Keys to Leading and Coaching Multi-Generational Sales Teams

Leading a multi-generational sales team requires understanding and accommodating the differences and unique strengths of each generation. It can be rewarding, but it’s not easy.

Here are a few tips to effectively lead a multi-generational sales team:

  1. Communicate effectively: Use clear, concise, and consistent communication to ensure everyone understands their role, goals, and expectations.
  2. Provide opportunities for development: Offer ongoing training and professional development opportunities to help your team grow and meet their career aspirations.
  3. Foster a positive work environment: Encourage collaboration, teamwork, and open communication, and celebrate the successes of your team.
  4. Flexibility in work styles: Recognize and accommodate different work styles, preferences, and technological needs of each generation.
  5. Embrace diversity: Recognize and respect the diversity of backgrounds, perspectives, and experiences of each team member.
  6. Lead by example: Demonstrate the behaviors and values that you expect from your team, and maintain a positive and professional attitude at all times.
  7. Regular check-ins and feedback: Schedule regular one-on-one meetings to check in with each team member and provide constructive feedback.

By being proactive and mindful of the different needs of your team members, you can create a positive, productive, and successful sales team.

Better Hiring in an Evolving Sales Talent Landscape

One of the key benefits of hiring a multi-generational sales team is the diversity of skills. For example, older salespeople may have years of experience in traditional sales techniques, while younger salespeople may be more familiar with leveraging digital sales tools.

Leaders who are adept at leveraging this range of skills build more agile teams that are more responsive to changing market conditions and customer demands. Younger salespeople may bring fresh ideas and enthusiasm to the team, while veteran salespeople may bring a wealth of experience and knowledge. This combination of skills, perspectives, and energy is exactly why multi-generational teams are so strong.

This also leads to cross-generational coaching. The veterans provide guidance to younger salespeople, helping them to develop their skills. At the same time, younger salespeople can bring energy, helping to keep the team motivated and engaged.

Finally, being open to hiring multi-generational salespeople gives you access to a wider pool of candidates. This makes it easier to recruit and hire top talent. The more talented your sales team, the more likely you are to crush your competition.


Download our FREE 25-page Interview and Hiring Guide that teaches you exactly how to conduct more effective interviews and engage sales candidates in deeper and more authentic conversations that allow you to make better sales hiring decisions.

About the author

Jeb Blount

Jeb Blount is one of the most sought-after and transformative speakers in the world…

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