The Secrets of a Successful CS Mentorship Program

Annie Dean is the CEO and CoFounder of RecastSuccess and a founding member of Vitally’s Success Network.

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I owe much of my career success to mentorship. 

When I was in the retail-wholesale industry, my first mentor, Patty Kampmann, taught me how to deliver delightful customer experiences and measure customer satisfaction. And as I moved into the tech and Customer Success world, Patty helped me identify transferable skills and experiences that contributed to my success in my new role. 

Mentorship has also given me lifelong friends like my co-founder, Michi Hu Pezeshki, who has helped me build RecastSuccess into a successful global organization that includes a network of about 200 volunteer mentors.

But it’s not just individuals who benefit from mentorships. Businesses reap the rewards through cost-effective learner development, shorter ramp-up time, and improved employee performance. That’s why I’m convinced that organizations looking to create high-performing Customer teams must invest in mentorship. 

In this article, I’ll share my exact recipe for creating a successful Customer Success mentorship program. 

1. Set Expectations Early

There are three main things to think about as you set expectations for your mentorship program. 

How Much Time Will This Take?  

It’s really important to be clear on how much of a commitment is needed on both sides to make the mentorship work. That way, everyone plans their schedules accordingly. It’s very discouraging when one person cancels or pulls a no-show repeatedly. 

Of course, there’s room for flexibility. Over time, participants can reduce or expand the allocated time depending on what’s happening in their lives. But it’s good practice to have a set cadence on the calendar from the beginning to guide everyone. In our case, mentorship meet-ups happen once a month.

Where Will the Mentorship Sessions Take Place?  

You also need to decide whether these meetings happen in person or virtually. If you can meet in person to establish the relationship, I think that's ideal. Face-to-face relationships are always going to be deeper than the ones that are strictly virtual, but I know that doesn't always pan out. 

For example, I live near Yosemite, and there are no other CS professionals here. That means if I want to mentor (or be mentored), it must happen virtually. Our mentorship program at RecastSuccess is virtual and caters to people in 38 different states. 

What Will People Talk About? 

Ideally, the mentee should guide every conversation. This means they must come prepared with a loose agenda focused on what they need help with. 

I would say don't make it all business, though. Mentors should get to know the other person as a well-rounded human being. Having the context of what's going on in your mentee’s life makes your advice more impactful. 

Ideally, the mentor should also have some interesting questions in their back pocket in case the agenda isn't enough to take up the whole time or the CSM wasn't prepared. These questions should pique your mentee’s curiosity and encourage them to think critically about their career.  

2. Set a Timeline

The truth is there are no hard and fast rules for setting a mentorship time frame. 

I’ve seen people have the same mentor for 20 years and counting. I’ve also seen people have specific mentors for different seasons of their careers. In my case, I prefer the latter because it’s easier to work towards a specific goal and hold each other accountable. 

Our mentorship program at RecastSuccess runs for a year — usually the mentee’s first year on the job as a Customer Success professional. The mentor’s role here is to help them find their feet. Once they have more skin in the game, their needs typically change. 

At that point, they might be looking for advice on how to get promoted and move into CS leadership. Some mentors don’t have experience in these areas, so they can’t offer much help or advice. They’re better off focusing on their zone of genius, which is helping beginner CSMs get a solid footing in the field. 

3. Make It Inclusive 

One of the biggest mistakes people make with mentorship is restricting it to a particular group of people. 

And it’s not like they do this intentionally. What typically happens is that the individuals who feel most comfortable raising their hands to be mentees tend to share the same demographic characteristics as those who’ve signed up to be mentors. So, it’s like a chain reaction. If you’re not careful, you might end up locking out underrepresented people who really need these mentorship opportunities. 

My advice is to create equal opportunities for people from diverse backgrounds to participate in mentorships, especially for underrepresented individuals. It isn't enough to have them as mentees; encourage them to mentor other people as well. I think you can deliver a lot of value by pairing people from different backgrounds and experiences as mentor-mentee within your organization.

4. Guide First-Timers Through the Process

Understand that not everyone comes from a background where they learned how to ask for help. Take people from Ivy League schools, for example — mentorship is a core part of their educational experience. 

But it’s unlikely that everyone on your team is an Ivy League graduate. In fact, I reckon that the people who often need mentorship the most may not come from such a background. That’s why it’s really important to provide structured guidance on how to ask for a mentor in the first place. 

Having go-resources that teach people what to expect from a mentorship program, the kind of questions they should ask or avoid, and generally how to approach their mentors takes some of the fear out of the process. That way, they are more likely to raise their hands to participate in the mentorship program.

5. Encourage Mentees to Pay It Forward 

Ultimately, what makes many mentorship programs successful is the willingness to pay it forward. It really makes a difference when people spare an hour or two every month to give back to the mentorship program they benefited from. 

In my experience, many past mentees don’t volunteer as mentors because they feel like they don’t have it all figured out. But the truth is, mentorship isn’t about perfection — it’s about making another person’s journey a little easier. Think about it this way: when you share your experiences and mistakes with somebody else, they won't have to go through the heartache that you did. 

If you feel like you don't have it all figured out and you’ll make a ton of mistakes, then you are the most valuable possible mentor out there.

Wrapping Up: Prioritize Genuine Personal Connections 

Like dating, Customer Success mentorship is all about finding and nurturing the right connections. Two people might look like a good match on paper but not hit it off in person, and that’s okay. Don’t try to force things. 

A mentor should be someone you enjoy spending time with. That’s why I always advise people to do a test run first. See how that first conversation goes and how you both feel about the relationship before committing fully.

Most importantly, don’t be afraid to advocate for yourself. Someone might be an all-around amazing person but not a good fit for you. That’s totally fine. Speak up — a good mentorship program will listen and help you find your person. 

That’s it from me! I’d love to chat more with anyone who’s building or scaling a CS mentorship program. Feel free to connect with me via LinkedIn anytime!

Enjoyed reading this? Check out other CS leadership articles from Vitally’s Success Network

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