Steering the Ship: Mapping Leadership and Goal-Setting for Customer Education Image

Steering the Ship: Mapping Leadership and Goal-Setting for Customer Education

We’re starting 2024 with a new webinar series jam-packed with best practices and strategic insights proven to help customer education teams get their programs off the ground

We’ve had two sessions so far, both featuring Lila Meyer, Director of Global Education Services at Gainsight and special guest Kristine Kukich, Principal Owner of the Training Sherpa, joined the latter to dive into how she sets customer education goals.

Here are some of our favorite takeaways from those webinars, along with some additional insights to ensure you lay a sturdy foundation for your customer education program.

The Art of Customer Education: Appointing the Right Leader 

Former White House Chief of Staff Erskine Bowles once said, “Leadership is the key to 99% of all successful efforts.” While he wasn’t talking about customer education or starting an academy, he certainly could have been. There’s nothing more important to your customer education program’s short- and long-term success than appointing the right leader.

Luckily, appointing the right leader doesn’t have to require a long-winded hire process—here’s how I’d think about it. 

Look Internally First

Although I don’t want to discourage you from looking externally for your team lead, I bet you have someone internally who’s already embracing a customer-educating mindset. 

Whether that person works in Customer Success, Support, Product, or somewhere in between, I can guarantee that someone, somewhere, has pinpointed a gap in the customer journey that education can fill. For example, maybe a C.S.M. is recording Loom videos for new customers to help with onboarding, or a support rep is making an F.A.Q. doc based on the most common tickets. 

Not only will an internal hire speed up the process and get your academy live faster, but because you’re appointing someone with existing knowledge of your business, product, and customer needs, you’ll likely find yourself on the fast track to real business results. 

Find these people and then narrow down the list by asking them some pointed questions:

  • How would you align customer education to greater business objectives? 
  • Do you have experience leading and motivating a new team? 
  • Do you have any knowledge of course creation and delivery, i.e., have you used a learning management system (L.M.S.)
  • Can you turn complex topics and features into easy-to-understand chunks of knowledge? 
  • Can you pivot quickly and operate under pressure to maintain leadership buy-in?


The list goes on, but your goal remains the same: Find someone passionate about helping your customers and ask them questions that give you a glimpse into how they’ll approach your program. 

Looking Externally? Here’s What to Consider 

If you look externally for a leader—which is fine—there are a few considerations to keep in mind to ensure you’re hiring the right person. 

  1. Clearly Define the Role: Set very clear expectations and goals to make it crystal clear what the leadership role entails. The last thing you want is surprises (for you or the new leader).
  2. Focus on Culture: Hard skills are key to successful leadership, but if the person isn’t aligned culturally with the overall business and learning objectives, you’re up a creek without a paddle.
  3. Be Thoughtful About Onboarding: Bring your new leader up to speed on everything related to your company, including the product, customer success processes, existing educational initiatives, and culture. 

Building a Foundation with Realistic Goals

I could start and end this section with one sentence—set S.M.A.R.T. goals—and leave it at that, but that seems too easy. But in all seriousness, don’t overthink your goals. Instead, pinpoint where you can have the most significant impact right now—that’s your goal(s). 

For example, is your Support team drowning in tickets about a specific feature? Do your C.S.M.s need help onboarding an influx of new customers? Is your product team less than thrilled about adopting a new feature? 

Find those glaring holes and pour your resources into solving a few. Kukich suggests setting three at a time. “It’s three large initiatives, most likely segmented into components, that I can take through quarterly. That can lead to actionable and measurable items for the team,” Kristine continued, “Think at a size that allows you to work hard and smart so that you can show value and get return on whatever you’re deciding to build.”

How do you know which goals to start with? A feasibility and impact analysis will help. Take your potential goals and rank them on a graph similar to the one below. Once you have everything plotted on the graph, start with the goals with high user value and low organizational effort (in the top-right quadrant). Those are your goals to start. 

Then rinse and repeat with another goal, and before long, you’ll have a multi-faceted customer education program that’s tackling a ton of business challenges and serving a variety of customer segments. 

Remember: You can’t solve everyone’s problems on day one. Part of being a good leader is balancing expectations with reality. Be smart about your goals, identify where you can make the biggest impact, introduce them to the company…and hold everyone accountable. 

American editor and journalist Herbert SwopeI said it well: “I cannot give you the formula for success, but I can give you the formula for failure, which is: Try to please everybody.”

Empowering Your Customer Education Leader

Your customer education team is sailing into uncharted waters. There will be plenty of success but an equal amount of failure, learnings, and pivots along the way—and that’s fine. I’d go as far as to say if you’re not making mistakes, you’re not pushing the boundaries enough.

The success of your customer education program rests heavily on empowering your team to make these mistakes and learn. There can’t be any walking on eggshells. Teams, especially with new leaders, must feel comfortable thinking outside the box, experimenting with new tactics, and iterating as they go. That’s the only way to achieve customer education success in 2024 and beyond. 

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