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7 Steps to Establish a Successful Sales Mentorship Program

I will always be a believer in sales mentorship programs. Early in my career, the hands-on training I received from my mentors taught me more than any other experience. I can remember deals at every company I’ve worked for that I simply wouldn’t have closed without help. Applying these learnings to subsequent deals enabled me to win them on my own — and in a much smaller time frame. Eventually, I took those learnings and taught them to sales reps I was mentoring.

As I’ve seen firsthand, mentorship programs accelerate the learning and promotion processes on a sales team. In fact, studies show that mentorship programs lead to increased salaries, quicker time to promotion, and higher retention rates.

But what’s in it for the mentor?

Sales Mentoring: What’s in It for You (the Mentor)?

Many top sales organizations use mentorship programs to both ramp new salespeople and groom senior reps for leadership roles. At the same time, it’s a lot of work for the mentor who could be spending their efforts closing new business. 

Sales mentors must keep in mind the long-term benefits to the organization, including: 

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 and also being a resource to put context behind each sales interaction as the reps gain experience.

The obvious benefit of a mentorship program, then, is that the organization is actively investing in the development of the sales team, which benefits the bottom line. As a mentor, you stand to benefit (in myriad ways) from working with an organization that is seeing the effects of this on the bottom line. 

But that’s a more indirect benefit of being a sales mentor. 

Another benefit is that, by honing the skills of a new team member, you get a refresher on the fundamentals of the role, which can serve to sharpen your knowledge and skills also. After all, according to the Roman philosopher Seneca, “While we teach, we learn.” In other words, the process of explaining something to someone else increases your competency as well.

Increasing Engagement

Instituting a mentorship program in your company increases employee engagement, especially if implemented when the employee is first onboarding with your organization. Great training sets the relationship off right.

In fact, individuals with mentors tend to excel in companies faster than employees without mentors, and the majority of mentors report their job as being more meaningful (Brad Johnson). As a result, both mentor and mentee become more engaged.

Improved Morale

Everyone knows that sales is challenging, particularly when prospect after prospect is saying “no.” This can have a negative impact on morale, which in turn feeds into a nasty cycle because sales teams with low morale do not perform as well. 

Sales mentorship gives both mentor and mentee 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 ability to develop leadership skills in the workplace, which are important in sales, particularly when it comes to motivating team members to accomplish more. 

It takes preparation for an organization and the mentors within it to reap the benefits described above. Unfortunately, many well-intentioned mentorship programs lack proper strategies and planning.

You can avoid the pitfalls by following these steps to establish a successful sales mentorship in your organization.

1. Have a “kick-off” meeting.

Hold a face-to-face conversation between the mentor, mentee, and the manager that oversees the team. The manager should introduce some questions to get the two employees talking about the program.

  • “Where do you see yourself in two years? 10 years?”
  • “Do you have a plan to get there?”
  • “How do you learn best?” (Trial and error, visual, reading, just-in-time learning, etc.)
  • “What day and time do you prefer to meet each week?”
  • “What’s your favorite coffee shop or local restaurant for walk and chats?”

These questions enable the mentor and mentee to establish goals to work toward and find a mutually beneficial discussion style.

2. 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.

I am also a big fan of splitting the first few commission checks between the mentor and mentee. Most likely the new rep is on some type of ramp, and witnessing a deal from first touch to close will take a lot of energy. If you don’t reward the senior rep financially, they tend to act more like a coach than a player, which leads to a slower deal time and less involvement in the negotiation (an area in which the new rep has the most to learn). The closing cadence takes a lot of practice, and the more exposure the junior rep receives to wins and losses, the more accurately they will be able to diagnose deals down the road.

3. 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 sales role is strictly inbound, you might want to start with training on chat, your CRM, and the product. 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.

In addition, don’t assume new salespeople will understand your acronyms and how to use the technology available. I once had to train one of my BDRs on Gmail, while another one needed help with WebEx. (Fortunately, these experiences taught me how to hire and keep great business development reps.)

4. 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.

5. 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.

At a QBR, for example, ask the new rep to showcase their business plan and learnings in front of their peers. Let the team ask questions after the presentation, which will make it relatively easy to tell if a newer rep is ready to step up and rely on their mentor less often. As an added benefit, this is a good opportunity for everyone to learn — not just the mentee.

6. Measure and quantify value.

Know your key metrics before you implement a mentorship program so it’s clear if the investment is paying off.

What to 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 first hand.

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.

7. 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 name to. We use Tettra here at Drafted to keep the team updated on key wins and losses.

There is a compelling case for investing in a mentorship program for sales teams — but if mismanaged it will be a chore instead of a fun learning experience. At the end of the day, you want your reps to build relationships that will last their entire careers.

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