How to become a Customer Education Leader

April 11, 2022

How does the next generation of Customer Education leaders prepare for their roles? How can you become a Customer Education Leader? What can we, as the current leaders, do to prepare them? These meaty topics are close to our hearts, and Dave and Adam discussed them with Stephanie Pellegrino on CELab episode 77: The Next Generation of Customer Education Leaders.

If you want to become a Customer Education leader, this is a prime time: demand is outpacing supply for leaders who have “seen the movie” and been through several cycles building and leading teams. This means there are more opportunities for current CEd specialists to move into leadership roles.

But this isn’t easy today, as new leaders are expected to come up to speed quickly. It wasn’t easy for us either, when we were getting started. We grew into leadership positions at a time where there was very little information out there on how to run a Customer Education function in a SaaS business, especially one outside of more traditional Education Services.

Now there’s much more information out there: more books, podcasts, communities, and leaders working out loud and sharing their experience. But what these resources still won’t tell you is what you’re actually walking into as a CEd leader, or how to prepare to get into that position.

We’ve put together a few tips based on our discussion in the podcast, as well as our experience as Customer Education leaders.

Understand how your business works, not just the Customer Education craft.

There’s a lot of great information and resources out there on the crafts of instructional design and training/facilitation. And you need to get good at these skills to form a point of view and progress in your career.

But to become a Customer Education leader, you’ll need to tie those to business objectives. How do they help your business make money, save money, grow, or support key initiatives? The more effectively you can do that, measure it, and tell the story, the more successful you’ll be.

This means you can’t just be a domain expert in education: you need fluency in the business. You may be surprised how, as you get more senior, you spend less time on the actual craft of Customer Education. Sure, you’ll make some decisions that relate to instructional strategies, but you’ll be spending more of your time on people management, performance, budget, cross-functional negotiation, strategy and vision, and other things that aren’t directly related to the craft.

The more fluent you get in your business, the more you’ll understand what to prioritize and deprioritize. There are going to be many initiatives that seem like “shiny objects” that don’t actually deliver business results, and having a keener business sense will help you argue for the right prioritization.

There isn’t only one way up

As Steph mentions in episode 77, Customer Education is becoming “less flat” – by which she means there isn’t just one career ladder from specialist to functional leader. It’s not that you are a trainer, then a training manager, then a director. Increasingly we see management and leadership roles within CEd as training managers, instructional design managers, community and engagement managers, etc.

When you think about your growth path, you don’t necessarily need to focus purely on becoming a manager, then a director, etc.

You have more options than ever to broaden your skills – ex. moving from instructional design to facilitation to community management. When you think about career transitions, we recommend thinking both long-term and short-term. If your long-term goal is to be a Customer Education Leader with a broad scope, how can you get experience in more of the areas you’ll eventually be leading?

For example, if you’re eventually going to be leading a team that owns training, documentation, and community, you’ll likely be a stronger candidate if you’ve built and/or worked in each of these areas. You’ll also have more perspective and expertise coming into the role, since you’ve spent time working in each of these areas and developing your point of view.

People management isn’t the only way to lead

Many people dream of being a Customer Education leader, owning the entire function and managing people, and then once they get there they realize it’s not for them. If you get far more pleasure out of your craft (for example, being the best possible facilitator, instructional designer, or program manager) than you do from managing performance, finessing budgets, negotiating with stakeholders, and selling your vision, then maybe being a functional leader isn’t the most fulfilling path.

Our society conditions us to say if you’re not moving up then you’re not successful, but in reality, many people in this industry lead more fulfilling lives and find success in their careers in senior specialist positions that keep them close to the work. After all, it’s often the actual craft of Customer Education, Instructional Design, or Training that brought us into this field.

While you’ll certainly end up doing more coaching, mentoring, and cross-functional partnership as you get more senior, being a people manager isn’t the only way to do it. As Customer Education teams grow, so do opportunities for senior specialists who work on more complex projects but don’t take on the overhead of managing people. If this sounds like more of a fit for you, it’s worth exploring these types of “senior individual contributor” paths with your leadership. Even if they don’t exist at your company today, they often will be created for exceptional performers.

Seek context from your leaders

If you want to become a Customer Education leader, start thinking like one. To do this, it’s important to get context from your manager and leaders on why they’re making certain decisions, or prioritizing what they’re prioritizing.

Now, this one comes with a big asterisk: don’t do this in a way that makes you seem like you’re questioning all their decisions (unless you genuinely are questioning them!) or that you can’t function without complete context. Customer Education professionals are expected to operate in ambiguous environments without complete context, especially as they get more senior.

But if you can invite your manager to share more context on their decisions and considerations, it will help you start thinking in this way too. We find it helpful to be transparent about this: you’re asking for context because you want to be able to make these types of decisions more independently, too. When you become a Customer Education Leader, you’ll now have more frameworks and have seen these decisions modeled previously.

Often, this helps you find the balance between the “way it should be” and the “way it actually is” — in other words, balancing idealism and best practice with pragmatism.

Raise your hand, plant the seeds, look in the mirror

It’s not often that your leaders will tap you randomly to become a Customer Education Leader (though it does happen sometimes, especially in startups). It’s important to raise your hand and let your manager know that you want to grow in this direction, whether it’s a people manager, a senior individual contributor, or something else.

Often, when people think about career growth, they take a passive rather than active approach. They might look at their company’s career leveling guides as a checklist to complete in order to earn a promotion. We prefer to think of career growth as a portfolio, not a checklist. You’re gaining a series of experiences that will prepare you to work at the next level.

In addition to building your portfolio, keep having discussions, and don’t shy away from feedback. When you tell your manager where you want to go in your career, bring your own ideas for how to get there and be open to their ideas too. Often they have different context than you do about career progression at the organization.

Make sure to have continuous coaching conversations so that you’ll know you’re headed in the right direction, not just your annual performance review.

You’ll also want to ask for feedback – even tough feedback – to help you discover your blind spots. Often when we receive negative feedback, we go into cycles of denial and come up with objections to that feedback. This means that the feedback was hitting us in our blind spots; we simply weren’t aware that we were missing something or behaving in a way that was holding us back. Instead of shying away from this or trying to object to it, aim to internalize the feedback and act on it. The more conscious we are of our own blind spots, the stronger leaders we become.

Finally, keep asking yourself about the direction you’re headed in. As we mentioned, Customer Education leadership looks really different in practice than it does in theory. The job you thought you wanted might not be the best path for you in reality. Many people currently in leadership positions want to step out of them because it’s not right for their lives or energy levels. So keep in touch with yourself on what your growth actually looks like, not just what you think it will be like.

Inside or outside roles?

There are many paths to leadership, and not all of them involve moving up at your current company. As we mentioned earlier, lateral moves at your current company can help you gain broader exposure and challenge you in new ways. But we also want to acknowledge that often people gain leadership experience by moving to different companies. For instance, if you’re a high-performing specialist at an established company, this might enable you to get a leadership or management role at a smaller company. Or you might move into a “team-of-one” builder role that eventually evolves into functional leadership.

Again, be honest with yourself about what these roles will look and feel like. It can be lonely being the only Customer Education person at your company, and you’ll spend a lot of time selling the value of Customer Education. It can also be taxing to play both the leader and builder role.

Conversely, going into a management role can be difficult if you’ve never done it before. Most managers don’t get adequate preparation and training for their roles, even on the job, so it’s important to get a sense of what type of support you’ll have.

The more clear-eyed you are about making these types of moves, the better prepared you’ll be when you’re actually in them.

Build a support network

At CELab, we’re all about finding our people. As managers, we often didn’t have anyone to turn to in our companies about Customer Education best practices, so we “found the others.” You can do that too! Find other Customer Education leaders to talk to, and build a support network together. And if you’re in a people management or leadership position, you can even find other managers in the company to be your peer support network.

Together, that’s how we build the next generation of Customer Education leaders.

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