Harnessing the Power of Mentoring in Sales

Having interacted with sales managers and their teams quite often during my 25 years in the industry, I often recall what my husband always asks me after every training session.

He doesn’t ask about the performance of the sales executives, but rather, his question is, “How are the sales managers?” He understands that in business, the leader of the team sets the tone and can be the catalyst for success or failure.

As our industry changes and evolves, I believe the most impactful sales managers possess qualities that include an understanding of compliance requirements, the selection of technology partnerships that intimately understand the business model and workflow, and the ability to bring innovation to their customers.

In the future, successful sales teams should view their leaders not just as managers, but as mentors. A mentor is someone who helps individuals reach their full potential, which is precisely what we’re looking for in the future of business technology sales management. A new sales mentor leader must embody key components, such as building the right culture within the team. This means fostering an environment where helping each other succeed is more fulfilling than merely focusing on individual success.

During a recent Fourth of July party, I spoke with a young college senior who has an internship in technology cybersecurity sales. His team was having unproductive meetings several times a week, discussing matters without achieving tangible results. He suggested changing the business model to have one weekly meeting while maintaining online conversations about strategies, schedules and accomplishments. Management took his suggestion to heart and made the necessary changes, resulting in a more productive work environment.

When I asked the intern if he’d like to work in such an environment after college, he replied, “Absolutely. I felt valued.” This is the right type of culture to promote, in which sales mentor leaders value everyone’s opinions and promote positive interactions no matter the employee’s tenure.

Collaboration and team selling are also traits younger sales executives seek from their senior mentor management. Sending a young person to canvas the field alone all day may not yield the most productive results. I’ve seen sales teams go out in groups to penetrate specific territories for their colleagues, which leads to better outcomes, fosters collaboration and makes the experience more enjoyable for the sales reps. Additionally, it provides opportunities for real-time prospecting options.

It was also beneficial to follow up the territory blitz with a daily group prospecting session from 4–5 p.m. This allowed for immediate follow-up from the day’s efforts, and it also allowed each team to give positive feedback about their colleagues’ fieldwork, receive encouragement from their peers, learn about alternative business approaches, and receive motivation and compliments from their leader and mentor.

To further encourage teamwork and mentorship, you can begin using phone blitzes. In some of the dealerships I partner with, everyone calls to make appointments for one of their sales team members. This alleviates the pressure of prospecting when individuals aren’t doing it solely for themselves. I’ve seen sales leaders actively participate in phone blitzes by making real calls to prospects, sometimes succeeding in securing meetings. This showcases their willingness to do the work they ask of their team while also serving as a great mentoring opportunity. Here’s how you can set up your own phone blitzes:

Introduce and Describe the Calling Session (15 minutes)

  • Team members will call prospects as someone’s assistant and learn new ideas by listening to colleagues
    • Pick one or two industries to focus on
    • Team members should identify nuances of the prospect’s industry,compliance, workflow, cybersecurity needs, remote access and profitability goals
  • Managers should make a call to break the ice and create a team environment
    • If the first call ends in a voicemail, leave a message and make another call
  • Explain the evaluation forms so teams can deliver a summary of their findings
  • Teams will provide their calendars and make calls one after another
  • Each rep should have the opportunity to make at least 12 calls

Hold the Calling Session (90 minutes)

  • Start the clock and walk around to observe and comment on the participants’ phone skills
  • Ensure participants are focused on tasks, not bogged down in conversations with each other
  • Make written notes to refer to during the summary and close
  • In between calls, share positive points and what might be tweaked for better future results

Summary and Closing (15 minutes)

  • Allow time to present findings, giving each person one minute to explain:
    • What new vertical “meat” they discovered
    • What they learned from their partner that they’ll add to their strategy
    • What happened differently when they called as the “assistant”
    • What tweaks they’ll make based on constructive criticism received from their partner
  • Time sales reps so they stick to concise findings and prevent long-winded summaries
  • Ask for final comments
    • You could lead with a question such as “What’s one thing you learned from the exercise that your partner did well?
  • Present a motivating statement about sticking to higher-level conversations and mention the positives you observed
  • Collect evaluation forms so you can make copies (also make copies of your notes) and distribute to all participants

Mentoring isn’t just about imparting knowledge and skills; it involves understanding sales executives as individuals. You should schedule one-on-one meetings to discuss their business accomplishments and learn about their hobbies and interests outside of work. Additionally, you can contribute to a culture of continuous learning by fostering a sense of community within the sales team. This can be done through shared charitable work or organizing a monthly sales team book club, for example. By encouraging individual education and acknowledging small successes, sales mentors can motivate and empower the team to achieve bigger goals.

Younger sales executives are motivated not only by financial incentives, but also by a positive environment that includes the ability to gain experience, receive encouragement and achieve victories. Sales mentors can provide positive affirmations and recognize accomplishments such as net-new meetings, commitment to work, professionalism, teamwork and supportiveness. An inclusive approach in which sales executives can vote on these recognitions creates a nurturing, positive environment that fosters more opportunities, increased sales and reduced attrition. It also acknowledges the changing dynamics of the workforce, with a supportive mentoring environment playing a crucial role.

Another impactful idea for sales mentors is to create a positive, lasting impression on prospects after the first net-new meeting. This can be done by calling them to express your gratitude; these calls should be made the next day for maximum effectiveness and to maintain momentum.

To approach this, encourage sales executives to use the CRM system to input information about their meetings on the day the meeting occurs. Next, you’ll want to create a list for upper management of the net-new meetings conducted the prior day. Sales mentors should then call each prospect within 12-15 hours of the meeting and express appreciation.

Here’s a sample conversation to help guide you:

Receptionist: “ABC Law Firm, how may we help you?”
You: “Hello, my name is Kate Kingston from Kingston Technologies. I’m calling about the meeting your IT director, John Bellows, had yesterday with Mike Simms from my team. Could I speak with John, please?”
Prospect: “This is John.”
You: “Hi John, this is Kate Kingston from Kingston Technologies. I wanted to thank you for meeting with Mike Simms yesterday. Mike is part of my team, and he shared how much he enjoyed learning about your firm. We look forward to being a resource for you, and I wanted to express our gratitude for the opportunity. You’re certainly in good hands with Mike, and we’re all here to serve the firm.”

If the call goes to voicemail, here’s a slightly different sample:

“Hi John, my name is Kate Kingston from Kingston Technologies. I wanted to thank you for meeting with Mike Simms from my team yesterday. I spoke with Mike, and he was impressed with what he learned about your firm. We work as a team here, and everyone is looking forward to being a resource for you. Thank you for the opportunity and have a good day. Again, this is Kate Kingston from Kingston Technologies, and you can reach me at 646-831-5184.”

Incorporating this practice into your prospecting routine sets your dealership apart from the competition. By showing gratitude and personal attention to prospects, you build trust and emphasize your team-oriented approach. This initiative extends beyond the usual demo or closing stages, displaying a culture of mentoring and support. By testing the effectiveness of this additional step and analyzing its impact on proposal and closing rates, you can quantify the results.

We all see the evolution the imaging channel is facing. Sales managers and executives must find new ways to create a community inside their dealerships to help avoid attrition, keep the team motivated and support a culture of individual and team success. Test the changes you want to make at your dealership by taking some of the steps I’ve explained here. This will ensure that your sales management team is doing everything it can to mentor the new sales executives and learn what their needs are to make them more successful.

Kate Kingston
About the Author
KATE KINGSTON, president and founder of the Kingston Training Group, has been exclusively educating business technology sales executives on every type of prospect across 60-plus industries and how they proprietarily use technology for the last 20 years. This knowledge is the cornerstone of KTG’s prospecting training and empowers the sales executive to schedule more net new meetings at the C-level with a vertical focus through foot, phone, email, and social media to (money-back) guarantee at least a sustainable 50% increase in net new meetings so they can sell more hardware, software, document management, managed IT, MPS, MS, ECM, 3D, supplies, telecom, and mailing solutions across your entire salesforce. This results in a sales force that can recommend the right technology infrastructure solutions by enhancing their understanding of their prospect’s business creating more robust proposals and sales. Kingston is recognized as an authority on lead generation, recruiting new hires from a prospecting skill base prospective, and new business development. She is a sales-driven, energized communicator who uses humor, audience participation, proven techniques, handouts and real-time phone calls in her training sessions.