EP 34: Why Understanding Learner Pain Points Is Key to L&D Success

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In our latest episode of Learning Matters, I had the chance to sit down with Dasha Crosby, Learning Director at US Bank. With over 15 years of experience in human capital management, talent strategy, and process improvement, not to mention a handful of awards in HR leadership, Dasha brought a wealth of knowledge and a refreshing perspective to our conversation.

Here’s a look at some of the biggest takeaways from our discussion.

It All Starts with Understanding Pain Points

When asked about what strategy matters most in learning and development today, Dasha didn’t hesitate: “It’s all about understanding the learner’s pain points,” she said.

Too often, learning programs miss the mark because they don’t dive deep enough into the barriers learners are facing. It’s not just about hearing “I don’t have time”, it’s about asking why learners feel that way. Is it leadership expectations? Competing priorities? Systemic obstacles?

Addressing root causes, not just symptoms, is where true strategic design begins.

Communicating the Value of Learning

One of the biggest lessons Dasha learned early in her career was that believing in the value of learning isn’t enough; you have to communicate that value in a way your audience understands.

It’s about meeting people where they are:

  • Business partners want to know how learning drives strategy and revenue.
  • Learners want to understand how it impacts their growth and success.

Learning isn’t a “check the box” activity. It’s a journey. And the more we can align learning initiatives to what matters most to stakeholders, the more impact we’ll see.

Building Learning Experiences: It’s a Team Sport

During the analysis and design phases, Dasha emphasized that crafting effective learning experiences is never a solo effort.

While many people think they can “just teach” because they know the content, true learning design is a science.

Instructional designers, facilitators, consultants, data analysts: it takes a village to create experiences that truly engage learners. And that collaborative spirit is what elevates training from good to great.

Measuring ROI: Data with a Human Touch

Of course, at the end of the day, stakeholders want to see results.

Measuring ROI in learning isn’t just about attendance numbers or quiz scores, it’s about setting clear goals from the start, tying them directly to business outcomes, and having access to the right data to measure success.

Dasha also highlighted the importance of storytelling with data; putting a face to the numbers. “It’s not just metrics; it’s about showing the human impact,” she shared, nodding to inspirations like Brené Brown.

AI, VR, and the Future of Learning

Looking ahead, Dasha is excited about the role of AI in speeding up content delivery, personalizing learning experiences, and taking administrative burdens off learning teams so they can focus on strategy and innovation.

She also sees huge potential in VR and AR to create immersive, culturally rich learning environments giving learners the ability to step into someone else’s shoes or experience another culture firsthand, all from their own homes.

But with new technologies comes a familiar challenge: fear. “Change is hard,” Dasha acknowledged. “But if we lean into curiosity instead of resisting, we can make our work, and the learner experience, even better.”

Accessibility: Building for Everyone

Throughout our conversation, accessibility came up time and time again.
Creating great learning means making sure everyone can participate regardless of their abilities, environment, or background.

From offering closed captions to ensuring quiet spaces for focused learning, Dasha reminded us that true inclusion happens when we think about all learners at every stage of development.

A Personal Mission Rooted in Community

Dasha’s passion for education is deeply personal.Growing up in Akron, Ohio, surrounded by a multicultural family and a strong community spirit, she learned early the value of hard work, resilience, and empathy.

Her journey into learning and development started in the mortgage industry; getting so good at her job that someone asked her to start training others. Seeing people grow in their careers because of skills they learned was addictive, she said, and it’s what drives her to this day.

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