Skills Chat: In Person – NYC reflections

Last week’s dinner in NYC was a powerful reminder of why we do this work.

We kicked off the evening by asking everyone to introduce themselves as humans, not by job title. This wasn’t just an icebreaker. It was personal. Skill Collective was born out of a redundancy, and I remember how disorienting it was to feel like I’d lost my identity overnight. We often default to introducing ourselves by what we do professionally, as if our role is who we are. But the truth is, we’re so much more than that. We’re parents, friends, mentors. We’re defined by our values, our character, our passions, not our LinkedIn headline.

That framing set the tone for the evening.

To introduce the theme, I shared the story of a neighbour who discovered pools of water mysteriously forming downstairs in their brand-new home. At first, they assumed a leaky pipe or rising damp. But after months of confusion, the root cause emerged: the builders had forgotten to install the waterproof membrane on top of the foundations. The only fix? Demolish the house, lay the membrane, and rebuild from the ground up.

It’s a true story, but also a powerful metaphor for many organisations we work with. They’ve built beautiful architectures: HR systems, org charts, new operating models. But without foundational alignment around skills, data, and purpose, the cracks start to show. The systems look solid on the surface, but they’re leaking impact.

As part of the dinner, we introduced a simple game to guide the discussion. For each course, there was a bowl of question cards at the centre of the table, each one tied to a different theme:

• What’s actually going wrong

• How to fix the stuff under the surface

• How to finally get impact from all that investment

Each bowl was meant to spark a new round of conversation with each course. But in the end, we never made it past the first one.

The first question from the “What’s actually going wrong” bowl set the tone:

“If your CEO asked for proof that your skills strategy was working, what would you show, and what would you hope they didn’t ask about?”

It unlocked a raw, honest conversation about ROI. Not the buzzword kind, but the real, gritty tension of trying to demonstrate tangible value from skills work. The consensus? Most are struggling to measure impact in a way that matters to the C-suite.

The conversation reminded me of a critical truth. ROI only exists in relation to purpose. And in an enterprise context, that purpose has to be anchored in business objectives – what the CEO and leadership team are trying to accomplish over the next one to five years.

Here’s why that matters.

Business objectives, like growing market share, reducing time to market, or entering a new customer segment, drive business strategy. That strategy then informs workforce strategy: who you need, what they need to be able to do, and how you get them there. And that’s where skills initiatives come in.

The most successful organisations we’ve seen don’t just build a skills strategy. They build one that’s deliberately entangled with business value. That means asking questions like:

• What are the CEO’s top three priorities over the next 12 to 36 months?

• What workforce capabilities are critical to achieving those priorities

• Are we building those skills internally, buying them externally, or redeploying what we already have?

Let’s say the CEO has a clear business objective: increase market share by 3 percent in the next fiscal year.

• Business strategy: Launch two new product lines aimed at underserved markets.
• Workforce strategy: This might mean accelerating innovation cycles, reducing product development lead times, or expanding go-to-market teams.
• Skills strategy: Now you’re at a decision point. Do we upskill the existing product teams to move faster and build differently? Or do we need to recruit a new cohort of product talent with experience in rapid prototyping, design thinking, or niche market knowledge?

From here, the skills initiative becomes clearly accountable to that business goal, whether through learning pathways, strategic hiring, talent redeployment, or internal mobility programs.

So when the CEO asks for proof the skills strategy is working, your answer becomes:

NYC was our first Skills Chat: In Person, and it won’t be the last.

We’re already looking ahead to the next one, with more honest conversations, sharper questions, and new cities on the list.

Stay tuned. More to come soon.