9 Steps to Establish a Successful Sales Mentorship Program

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Alex Mackenzie
Alex Mackenzie


Sales mentorship programs' value is multifaceted — these kinds of initiatives can help accelerate recent hires' development, provide veteran reps with leadership experience, and bolster a sales org's long-term success. That said, structuring and implementing one of these programs is much easier said than done.

Here, we'll review why sales mentorship programs are so effective, get a solid sales mentorship outline, and go over the steps you need to take to implement one of your own. Let's dive in.

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Sales Mentoring: What's in it for the mentor?

Several top sales organizations implement mentorship programs for a number of reasons — namely to ramp new salespeople and groom senior reps for leadership roles. They're valuable arrangements that can help both mentors and mentees grow.

That said, participating in one of these programs can be tough on the seasoned sales reps who assume mentor roles — taking on one of these positions means piling additional responsibilities onto their existing workload.

So if you're a veteran rep considering participating in a mentorship program, you should know the long-term benefits one of these roles can pose for your professional development and the success of your sales org. These include:

Knowledge and Skill Development

The best mentors are committed to the organization and want to give back to junior reps by sharpening their skills through training. They also see the value in acting as a resource to put context behind each sales interaction as their mentees gain experience.

The most obvious benefit of a mentorship program might be how it impacts the organization's bottom line. By putting one of these programs in place, leadership is actively investing in a sales team's development. And as a senior sales rep, you stand to gain from your team collectively developing — at least indirectly.

Beyond that, helping a new team member hone their skills, you can get a refresher on your role's fundamentals — keeping your own skills that much sharper. As Roman philosopher Seneca put it, "While we teach, we learn." In other words, the process of explaining something to someone else increases your competency as well.

Increasing Engagement

Implementing a mentorship program at your company increases employee engagement — especially when new reps are first onboarding. New hires tend to excel at companies faster when they have someone to reliably show them the ropes, and mentors often find their work more meaningful when they get to impart their knowledge and expertise to mentees. In turn, all parties involved become more engaged.

Improved Morale

Everyone knows that sales is challenging — particularly when prospect after prospect is saying "no." Consistent rejection can naturally take a toll on morale, feeding into a nasty cycle of underperformance. Sales mentorship programs give both mentors and mentees the opportunity to break away from it for a little while and focus on what needs to be done to make it go right.

Leadership Development

Aside from being more engaged with the organization, mentorship provides mentors with the space to develop leadership skills in the workplace — making for more engaged senior reps in the short-term and more effective leaders, down the line.

Mentorship Program Outline

sales mentorship program outline for more effective sales mentorship

1. Identify primary goals.

When constructing an effective mentorship program, you need to start with a firm understanding of what you want mentors and mentees to gain from it. Set solid primary goals.

Are you trying to minimize turnover? Improve overall activity? Increase engagement from all parties involved? Pin down what you want to see from your ideal program, and use that insight to shape how you structure yours.

2. Agree on meeting cadence.

Once you know what you want out of your program, you need to establish an appropriate meeting cadence that allows your mentors and mentees to connect consistently — without commanding too much time out of their day-to-days.

The cadence you land on will depend on your sales org's needs and how involved you want your program to be. Once or twice a week — with the flexibility for mentors and mentees to book some time on each other's calendars — will probably be enough. But if you feel like that cadence is insufficient or excessive, you can experiment with other schedules.

3. Align on expectations.

Once you have your goals identified and an appropriate meeting cadence set, you need to set certain parameters for how the mentorship program is going to function. Will mentors be expected to regularly put agendas in place? Who is going to set meeting times? Will mentees have homework?

Ask all of these questions and more when constructing your mentorship program. You want to have some degree of consistency across these arrangements — setting baseline expectations and ensuring that your mentors and mentees abide by them are central components of a productive mentorship program.

4. Define how you'll measure success.

You can't know if your program is effective if you have no concept of what "effective" is supposed to look like. Look at the goals you set before implementing your program, and determine hard metrics that can help you gauge whether you've achieved them.

Those might be related to activity, pipeline development, broader morale, revenue generation, or any other improvements you'd like to see in how your sales org operates. Assign relevant KPIs to those goals, and measure how they either improve or stall after your mentorship program has run its course.

1. Incentivize mentorship.

Shocking as this might sound, mentorship programs can't exist without mentors — and assuming one of these roles is rarely convenient. Mentors are essentially taking on extra work when they sign up for these kinds of programs, so if you want to maximize your pool of potential mentors, you might need to sweeten the pot.

Let them know enrolling in your mentorship program is an opportunity to demonstrate leadership — one that won't go unnoticed or unappreciated. Make it understood that successfully fulfilling one of these roles could factor into compensation or promotion decisions. One way or another, add a little oomph to the opportunity that can make it that much more appealing.

2. Have a "kick-off" meeting.

Once a mentor and mentee have been connected, arrange a face-to-face conversation between them — along with the manager who oversees their broader team. Management should raise some key questions to get the other parties talking about the program. Those could include:

  • "Where do you see yourself in two years? 10 years?"
  • "Do you have a plan to get there?"
  • "How do you learn best?"
  • "What day and time do you prefer to meet each week?"

Questions like these are both disarming and practical. For one, they give mentors and mentees some space to get to know each other in a professional context. They also offer perspective on how both parties communicate and set the stage for effective goal setting.

3. Clearly define roles and responsibilities for mentor and mentee.

"What's in it for me?" This answer needs to be clearly defined in the vetting process for pairing two reps together. If you match people arbitrarily, the relationship won't help either one. It's crucial to have the manager involved in pairing the two employees. A new rep that is having trouble with the team's CRM and a senior rep who wants to pursue a career in sales ops would be one perfect scenario.

4. Build a playbook.

Create a tangible playbook you can print out and stick to a calendar. Just like a good workout guide, having measurable, regularly spaced milestones leads to faster progress. It's easy for reps to get tied up with customers — but a weekly face-to-face should take place regardless of how busy either rep is.

The playbook should be assembled by the manager overseeing the program with the support and feedback of the first few participants. This is a work in progress but should become a fixed asset after the first few iterations. A successful playbook includes a checklist that builds skills in the order that reps will need them. Identify which skills are needed on day one versus day 90, and write your playbook to fit.

For example, if the role is predominantly outbound, start with calling scripts, email templates, and competitive intelligence — as your reps will need to book appointments before product demos. The mentor can then join the first few meetings with customers to demonstrate how to run an initial discovery call.

5. Share best practices.

Sponsor a monthly lunch for all the mentors to show your appreciation for their help, as well as facilitate discussion about what is working and what's not. Make sure there is a specific topic for each meeting. Ask mentors where their mentees are currently falling short in the sales process or which types of questions they're hearing across the board.

Once the team identifies two to three common themes, focus on those for the month. You don't want mentees to become overwhelmed. These meetings also help identify areas that need helpful content from the sales enablement team, so future reps won't need to look to their mentors for answers.

6. Plan an exit strategy.

New reps must "graduate" at some point, or they will never stop leaning on senior reps. Depending on your sales cycle and the amount of coaching required, these weekly meetings should last a minimum of six to nine months. The time necessary to become fully independent varies for every organization, so use a presentation or quarterly business review.

7. Measure and quantify value.

Know your key metrics before you implement a mentorship program so it's clear if the investment is paying off. You should measure:

  • Activity (phone calls, emails, meetings)
  • Pipeline development (new opportunities created, proposals)
  • Revenue (deals closed, time to close, ACV)

You'll also be able to see if mentees are making progress through milestones like the moment where the new rep goes from asking questions to answering them. These are hard to quantify but easy to understand when you see them firsthand.

Most reps tend to rely on "just-in-time learning," also known as, "I have gotten a question for the first time, I'm going to hit my mute button and ask the salesperson sitting next to me." If the program is working, there should be a point where the rookie rep can answer 99% of those on their own.

8. Showcase small victories.

The continued success of the program depends on continually highlighting its wins. For instance, ask an executive to tell the story of a great team accomplishment at an all-hands meeting.

You want your veteran reps to feel recognized by management. The new reps on your team should be excited to work with people capable of getting them ramped up quickly.

If you have an internal wiki, use it to recognize people. This provides a repository of the program that people can tie their names to.

9. Make room for feedback.

You can only get so much out of your mentorship program in the long run if you don't gauge whether it's working for everyone involved. That's why you need to give mentors and mentees the space to offer feedback — both on how their counterparts are performing and the program itself.

Make sure both parties feel comfortable voicing both praise and frustration with how the partnership is going. Hear everyone out, and try to remain impartial. Also, be open and receptive to concerns about elements of the program like meeting cadence, expectations, and rigor.

If you neglect this step, you're selling your program short. Structuring an effective sales mentorship arrangement is an ongoing process. There's almost always room for improvement, so listen to what both mentors and mentees have to say, and incorporate their feedback — especially if multiple participants raise the same issues.

Sales mentorship programs have tremendous potential to aid the professional development of everyone involved — all while offering a big-time boost to a sales org's operations. But putting together and sustaining a successful one can be tricky, and if you mismanage yours, mentorship can seem like more of a chore than a valuable learning experience.

Still, you want your reps to build relationships that will last their entire careers, learn from one another, and ultimately grow both personally and professionally — an effective sales mentorship program can do all that and more.

Editor's note: This post was originally published in February 2017 and has been updated for comprehensiveness.



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