S06 E01: How upskilling boosts careers, culture & engagement in 2026
Why upskilling is the defining HR challenge of 2026
According to Gallup’s 2024 State of the Global Workplace, only 23% of employees globally are engaged at work — a figure that has barely moved despite billions spent on learning programs. The problem is not budget. It is design.
Shari Chernack, Chief People Officer at Isaacson, Miller, argues that most upskilling programs fail because they are built for an imaginary median employee rather than the real person doing the work. In this episode, she introduces the Learning & Performance Flywheel — a framework connecting real-time listening directly to learning decisions.
Why most learning programs fail to move the employee engagement needle
Chernack identifies three failure modes that organizations consistently underestimate:
Failure Mode 1: Organizational agenda over employee growth. Programs built around what the organization wants employees to know — rather than what employees need to grow — register as inauthentic. When that misalignment is visible, disengagement follows.
“A lot of learning programs are designed around what the organization wants employees to know, not around what employees actually want to learn or what they feel they need to grow.”
Failure Mode 2: The median employee myth. Programs built for an average employee miss the actual person in the seat. Personalization is not a luxury — it is the baseline requirement for relevance.
Failure Mode 3: The sugar rush effect. High-energy training events produce enthusiasm that fades on return to routine work. This breeds cynicism — employees approach future learning with skepticism before it even begins.
The fix is not better program design. It is a different philosophy: continuous, employee-led learning connected to visible career outcomes — supported by real-time employee listening that surfaces needs before they become disengagement signals.
How employee-led development funds transform engagement and ownership
Isaacson, Miller runs two separate development funds — an approach Chernack credits to the organization’s culture, not her own initiative:
Any learning the employee finds valuable — regardless of whether it connects directly to their current role. Employee chooses.
Job-related certifications and degree programs. Managers and L&D offer guidance, but the final decision belongs to the individual.
“That shift in ownership makes a significant difference in how people experience learning. This is a true empowerment opportunity that fully benefits the employee.”
Isaacson, Miller also enables group learning — teams can pool individual allocations to take courses together. Shared learning sustains new behaviors through peer reinforcement long after the course ends, directly countering the sugar rush effect.
The Learning & Performance Flywheel: Shari Chernack’s framework for CHROs in 2026
In most organizations, learning and performance management run in parallel without informing each other. Learning is assigned based on organizational priorities. Performance feedback arrives too infrequently — often annually — to shape any development decision.
Chernack’s answer is the Learning & Performance Flywheel — the most important move she believes CHROs must make in 2026. The flywheel closes the gap between what employees experience at work and what they are being taught.
The flywheel changes how performance management is experienced. When performance discussions happen continuously — without the stakes and formality of an annual review — they become a natural part of working life. For CHROs building this infrastructure, continuous listening tools are the foundational investment. The flywheel cannot operate without real-time data.
How real-time listening and AI sentiment make upskilling personal and inclusive
Annual surveys are snapshots. By the time the data is collected and analyzed, it can already feel dated — especially when employee needs are shifting due to AI adoption or organizational change. Listening must happen through multiple channels on an ongoing basis.
Chernack draws a clear distinction: employees must feel genuinely heard, not tracked and monitored. Listening mechanisms that feel like surveillance create suspicion — the opposite of the psychological safety needed for honest developmental dialogue.
“When organizations get listening right, they can respond in developmentally appropriate ways in something closer to real time. That is when upskilling starts to feel like it is connected to someone’s feedback — that needs are being addressed as they are surfaced.”
At Isaacson, Miller, learning and tradecraft is one of four pillars in the organization’s ongoing listening process. Development quality is monitored continuously as a barometer of organizational health — not reviewed once a year.
Chernack describes two orientations effective learning infrastructure must serve:
Actively seeking specific skills, self-directing with minimal prompting. Needs access to a wide menu, not a prescribed course.
Time-constrained, needing learning brought to them in concise, accessible formats — a 30-minute session or an asynchronous watch-at-2x clip.
Measuring cultural health through upskilling initiatives
An organization that invests in development is communicating something specific: it wants people to stay and grow, not just perform a function until something changes. That signal shapes culture.
When Chernack describes learning and tradecraft as a barometer of organizational health, she points to something measurable: the degree to which employees see a credible connection between their development and their future at the organization. When a career ladder has clear skill expectations at each level and performance feedback is timely, employees experience a confirmation of intent.
Chernack is explicit on one point: the goal is not to boost engagement scores. Scores are a reflection of how the organization is performing. Focus on genuinely supporting people — real learning investments, real-time listening, development connected to career outcomes — and the data follows.
What you’ll learn from this episode
Key insights from Shari Chernack
Learning programs are designed around what the organization wants employees to know, not around what employees actually want to learn or feel they need to grow. So people can sometimes see that a program exists primarily to serve the company’s agenda — and that can lead them to disengage.
Why L&D Programs FailThat shift in ownership makes a significant difference in how people experience learning — this is a true empowerment opportunity that fully benefits the employee.
Employee OwnershipEmployees shouldn’t feel like they’re being tracked and monitored versus being genuinely heard — because that creates suspicion and a fear of surveillance.
Real-Time ListeningThe relationship between a person and their development is very personal. If we fully automated it, we’d lose a lot of the nuance and dialogue that drives great development conversations.
AI in Development
Full Episode Transcript
CultureClubX S06 E01 · Shari Chernack & Darcy Mehta · 29 minutes
Frequently asked questions
Common questions about upskilling, employee engagement, and the Learning & Performance Flywheel — answered based on insights from this episode.
Most learning programs fail because they are designed around what the organization wants employees to know, rather than what employees actually want to learn or feel they need to grow. Programs built for an imaginary average employee miss the actual person in the seat. When learning feels like a company agenda rather than a personal benefit, employees disengage. The third failure mode is the “sugar rush” effect — high-energy training that fades as soon as employees return to their routines, breeding cynicism about future learning opportunities.
The Learning and Performance Flywheel is a framework coined by Shari Chernack, CPO at Isaacson, Miller. It describes a continuous cycle in which real-time performance feedback directly informs learning decisions, and learning outcomes directly inform performance conversations. In most organizations, learning and performance management operate in parallel without informing each other. The flywheel closes this gap — so upskilling is driven by live data on what employees actually need, and performance feedback becomes a natural, ongoing dialogue rather than a dreaded annual event.
Real-time listening through multiple channels — pulse surveys, manager dialogue, digital tools — allows organizations to surface employee needs as they arise, not six months later via an annual survey. When employees see that their feedback directly shapes available learning opportunities, upskilling feels connected to their voice and reality. The key caution is ensuring employees feel genuinely heard rather than tracked and monitored, which creates suspicion. Organizations must design listening mechanisms that match their cultural context and that feel safe and responsive, not surveilled.
Effective organizations create a clear line of sight between learning and career advancement through visible career ladders with skill expectations at each level, and by embedding learning and tradecraft as explicit dimensions of their ongoing listening process. At Isaacson, Miller, learning is one of four pillars in the company’s listening framework — making it a measurable barometer of organizational health rather than a nice-to-have. When employees see that the organization is paying attention to their growth and using that data to improve, it signals genuine commitment.
No. While AI can add tools and guidance to the learning process, fully automating development decisions risks losing the nuance and dialogue that drive great development conversations. As Shari Chernack states, the relationship between a person and their development is very personal. High-touch organizations that keep humans in the loop — especially around individual career growth — preserve the trust and contextual intelligence that AI cannot replicate. AI should enhance the learning infrastructure, not remove the human from the loop.