The future of work demands a powerful blend of technical expertise and human-centered skills that appeal to the five generations in the workforce. This isn’t just professional development—it’s a strategic business advantage driving real bottom-line results. No one is better positioned than the middle manager to not only start development conversations with their teams but offer them continuous learning opportunities.

In this episode, Jen is joined by Michelle Westfort, Chief Product Officer at InStride, who believes the smartest organizations are weaving education into the fabric of their culture, not just offering it as a program or benefit.

Michelle Westfort is a globally recognized leader in post-secondary education with over 20 years of experience. An integral member of InStride since its inception in 2019, she brings a bold sense of innovation to drive successful programs and partnerships derived from a humble immigrant family upbringing. 

In this conversation, Michelle shares how combining technical and human-centric skills is creating a competitive advantage in the workplace. She busts the stereotype that older workers are resistant to learning— and shares what learning opportunities they’re actively pursuing. Michelle offers a way for middle managers to prioritize continuous learning among their team, regardless of generation, and shares how a reverse mentorship programs was a hit with one of their clients.

The business impact is clear: when managers prioritize development, people feel valued, teams perform better, and companies retain their institutional knowledge. Listen in for simple strategies any middle manager can implement tomorrow to start building a team that’s continuously learning.

Actionable Tips for Middle Managers

1. Ask your team members: “What’s the one skill you’ve always wanted to develop?”
2. Create a safe space where people feel comfortable admitting what they don’t know
3. Role model continuous learning by sharing what you’re learning yourself
4. Consider implementing a reverse mentorship program where team members teach each other skills
5. Have regular career conversations with all team members, regardless of their career stage

Links Mentioned

• Instride – Michelle’s company that helps organizations build strategic education programs
• LinkedIn – Connect with Michelle on LinkedIn

Guest Bio

Michelle Westfort, Chief Product Officer at InStride, is a globally recognized leader in post secondary education with over 20 years of experience. An integral member of InStride since its inception in 2019, she brings a bold sense of innovation to drive successful programs and partnerships derived from a humble immigrant family upbringing. 

Her career has centered around unlocking access to education from high school launch programs to adult career pathways and from digital transformations to workforce skilling. Her work has spanned marketing, business development, program design, and strategy at mission-centric organizations such as The Learning House (acquired by Wiley NYSE: WLY), Pivot, Navias (ASX:NVT) and Education Management Corporation.