Onboarding 101: How Not to Sink Your New CSMs

Onboarding 101: How Not to Sink Your New CSMs

I've learned that a bad onboarding experience can sour a new employee's experience.

I vividly recall multiple times when my team and I were excited by a new hire coming on board - only to see our new CSM struggle mightily because the onboarding process didn't prepare them adequately for their role.

This, in turn, created a lot of downstream effects: higher turnover among new CSMs, decreased morale, strained relationships with customers, and a general sense of frustration among new team members and the existing team.

Fortunately, I've learned from my past mistakes. I now see onboarding as less of a checklist to be run through quickly and more as a real foundation for a new CSM’s long-term success and experience.

Here are some of the more impactful mistakes I've made.

Hopefully, you can learn from them.


Why You Should Care:

Onboarding Customer Success Managers (CSMs) is a critical phase that can make or break their experience and impact the team. Poor onboarding can lead to high turnover, low morale, and strained customer relationships.

Common Pitfalls of CSM Onboarding:

  • Rushing Engagements: Don't quickly push new CSMs into customer interactions.
  • Team Exclusion: Involve the existing team in the onboarding process for peer insights.
  • Static Plans: Avoid "one-size-fits-all" onboarding plans; be open to feedback and updates.
  • Lack of Mentorship: Ensure vital mentorship programs to guide new hires.

Big Takeaway:

Create a dynamic, inclusive, continuously improving onboarding process for long-term CSM success.

Scheduling Customer Engagements Too Soon

There may be a temptation to engage new CSMs with customers immediately, especially if they have experience as a CSM at other companies.

This mistake can hurt you – and your new employee – in the long run.

You never want to throw them into the pool's deep end when they're not ready to swim. In some cases, I've had to manage a CSM's book of business while they are up to speed. It's well worth it.

New CSMs that engage with customers too quickly can get frustrated, make mistakes because of their lack of knowledge, and inadvertently harm customer relationships. Having them engage with customers too quickly is not worth it.

Not Engaging the Team in Onboarding

Many managers – especially new ones – may feel that creating and executing the onboarding process falls solely on their shoulders. This is a mistake I’ve made in the past, and it has affected my new employees in a couple of ways.

First, if the new CSM isn’t actively engaging with the rest of the team, they won’t learn what the job is like from a peer perspective. CSMs who are “in the trenches,” so to speak, will have more insights into the role and the team’s best practices than you will as the manager.

The second reason this is a bad idea is because it doesn’t leverage the power of your team’s good ideas and insight. Collectively, your team has more knowledge and insight about the role than you do as the manager. If the team can provide input and help coach and mentor the new employee, they’ll feel more of a sense of ownership.

Below are a few ways I’ve gotten existing team members involved in onboarding. I’ll also share some techniques other organizations have used, which may inspire your thoughts.

How I Involve the Team in the Onboarding Process

🤝 Onboarding Buddy

I pair each new CSM with a more experienced team member for mentoring and advice. This doesn’t replace my role as the team manager - this strategy focuses more on peer-to-peer interaction. A more experienced CSM can help new team members understand the “why” of our processes and share some of the institutional wisdom that most employees know but isn’t written down anywhere.

📝 Joint Cheat Sheet

Like most companies, we use industry- or company-specific terms and acronyms. It can be frustrating for a new employee not to understand what others are discussing. I created a document we call “acronym soup” to list all these terms and their meanings. All team members update this doc regularly to keep it fresh and relevant.

👥 Peer Job Shadowing

Towards the end of the onboarding process, a new CSM begins sitting in on calls and meetings with customers. They’ll participate in sales calls, technical calls with our professional services team, and calls with other CSMs. This allows them to see how we interact with our customers.

📊 Onboarding Debriefs

After completing each new CSM’s onboarding, I debrief the entire team. We look at what worked and didn’t work in the process, areas where we could use more (or less) content, and so on. I typically ask the newest team member to take the lead in updating the existing onboarding plan, as their experience will still be fresh in their minds.

Additional ideas you can try out:

  • Peer-Led Workshops: Allow existing team members to conduct mini-workshops on specific topics they excel in.
  • Lunch and Learns: Schedule regular "Lunch and Learn" sessions where team members can share knowledge and experiences.
  • Group Project: Assign a small project that the new hire can work on with a team, fostering collaboration and hands-on learning.
  • 'Day in the Life' Presentations: Existing team members can present a "Day in the Life" overview, sharing their daily tasks and challenges.
  • Interactive Scenarios: Use role-playing or simulations to allow new hires to interact with existing team members in controlled settings.
  • Feedback Loops: Create a system where existing team members can provide ongoing feedback during onboarding and vice versa.
  • Team-Building Activities: Incorporate team-building exercises that require new and existing team members to work together.
  • Mentorship Circles: Instead of one-on-one mentorship, create small circles that include new hires and various team members.

By implementing some of these creative strategies, managers can improve the onboarding process and foster a sense of community and shared responsibility within the team.

Having a Static Adoption Plan

When I started building onboarding plans for new team members, I assumed they were "one-and-done" documents. I'd develop and roll them out and then change them if we had a new product or process a team member needed to know.

I got pretty consistent feedback from my new team members that the onboarding process was good, but modules "x," "y," and "z" needed to be changed. It was always the same modules mentioned. Why? Because I never incorporated the feedback!

Boy, have I changed!

Now, when I hire a new CSM, the most immediate previous hire is instrumental in helping update and tweak the onboarding plan. We have open and honest conversations about what worked, what didn't, and which sections or topics need to be added to the plan.

We have a much better onboarding plan and an improved experience for each new employee. An additional benefit is that the existing CSMs feel ownership in the onboarding process and, as such, are more likely to accept and excel as a mentor - which leads to my next point.

Neglecting Strong Mentorship

I mentioned the idea of mentorship earlier in this article and wanted to get back to it. In the past, I've made the mistake of not focusing on a strong mentoring relationship. Not doing so can create a poor onboarding experience for your new hire and may lead to premature attrition because they don't feel comfortable in the group.

In many cases – myself included – managers ask a senior team member to be a mentor for a new employee with no structure or guidance. It's very likely your Sr. CSM will get distracted by customer engagements and fighting fires, and so may not spend as much time as they should with the new team member.

Ideally, a mentor should be more than just a friendly person for your new CSM to go to. That's part of it, but the best mentors do more. Good mentors help shape the new employee's onboarding. They should help with the creation of the new hire's onboarding plan. Having the mentor cover some topics in a one-to-one interactive style is also a good idea.

Mentors should also schedule weekly check-ins with the new hire. The mentor can use these calls to answer new team members' questions about what they've learned or experienced. Perhaps more importantly, the mentor can help the new CSM feel at home.

Every company has its own culture, customs, and history. A mentor can help explain this to their new colleague to help them feel comfortable and welcome in an intimidating environment.

Final Thoughts

I mentioned at the beginning that I’ve made many mistakes in onboarding. True - but my goal is never to repeat a mistake.

As you start formalizing and revising your onboarding process, remember that you’re never really “done” with the process. It will always require tweaks and tunes along the way. Hopefully, the points above have helped you think about how to get your onboarding program started…or how to take it to the next level.

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