Harald’s Curious Corner

Across these conversations with Dave Derington, John Leh, Debbie Smith, Courtney Sembler, Kristine Kukich, Dan Braithwaite, Melissa Kruminas, Clea Mahoney, and Vicky Kennedy, one question kept resurfacing for me: what actually makes customer education matter?

In this wrap-up, I’m reflecting on where the season kept landing. Again and again, the conversation drifted back to the same tension: customer education is full of things that look promising on the surface yet leave the real problem untouched. What stayed with me is the gap between motion and meaningful change. The teams making a genuine difference are not the ones chasing more for the sake of more. They are the ones staying close to the business problem, taking foundations seriously, paying attention to what changes in practice, and treating AI as something that needs judgement rather than blind enthusiasm.

I’m also taking the podcast in a slightly different direction from here. Instead of building around longer story arcs, Harald’s Curious Corner will open up to more standalone conversations, which gives me more room to follow the most interesting people and ideas across learning, enablement, and customer education.

Some curious takeaways:
  • Start with the business problem, not the surface-level fix
  • AI adds value when the foundations are already strong
  • Real progress shows up in outcomes, not activity

Episode highlights:
(00:00) Welcome to Harald’s Curious Corner
(00:55) The tension between activity and real progress
(02:15) Solving the real problem before reaching for more
(04:22) AI as a tool, not a rescue plan
(07:57) Measurement that reaches business impact
(12:04) Building customer education around what actually works
(14:28) Speed, clarity, and the pressure to do more
(19:46) Looking back on the season and looking ahead

A look back at this arc:
Dave Derington’s Journey From Music to Customer Education: https://youtu.be/K8WSyVmuug4 
How to Tie Learning to Revenue: https://youtu.be/hNfQW7G_4XM 
What Great Customer Education Looks Like at Scale: https://youtu.be/7G5GZkCH_EM
How HubSpot Academy Revolutionized Customer Education: https://youtu.be/Jau6asUxEKY
Customer Education Metrics That Actually Impact Revenue: https://youtu.be/I39ghnpdTkw
Why Customer Education Needs Strategy First: https://youtu.be/7zALcAUrzvw

Connect with the guests:
Dave Derington on LinkedIn: https://www.linkedin.com/in/derington/ 
John Leh on LinkedIn: https://www.linkedin.com/in/johnleh/ 
Debbie Smith on LinkedIn: https://www.linkedin.com/in/debbiecareysmith/ 
Courtney Sembler on LinkedIn: https://www.linkedin.com/in/courtney-sembler/ 
Kristine Kukich on LinkedIn: https://www.linkedin.com/in/kristinekukich/ 
Dan Braithwaite on LinkedIn: https://www.linkedin.com/in/danjamesbraithwaite/ 
Melissa Kruminas on LinkedIn: https://www.linkedin.com/in/melissa-kruminas/ 
Clea Mahoney on LinkedIn: https://www.linkedin.com/in/cleamahoney/ 
Vicky Kennedy on LinkedIn: https://www.linkedin.com/in/vickykennedy/ 

Follow me on the following sites:
Harald Overaa on LinkedIn: https://www.linkedin.com/in/haraldovera/ 
Subscribe to Harald’s Newsletter: https://www.linkedin.com/newsletters/6901795950403186688/ 

What is Harald’s Curious Corner?

Harald’s Curious Corner is where curiosity meets connection.

Harald chases that question with a guest, gathers perspectives from voices across the industry, and then steps back to reflect on what it all means. The show unfolds like a story arc, part exploration, part roundtable, part reflection, blending imagination with analysis.

The result: trusted insights, meaningful conversations, and forward-looking takeaways that shine a light on where learning is headed next.