OVERVIEW

Host: Kristy McCann Flynn, CEO and Co-founder of SkillCycle

Upskiling, re-skilling, cross-skilling, and any other type of skilling initiative your organization undertakes relies on one thing. Just one. And the ability to assess your company’s readiness for the future of work is the first step toward a comprehensive strategy that drives growth across your employee lifecycle.

Fear, AI, and Why Now Is the Moment 

(00:02:40 – 00:04:23)

A lot of people see AI as a replacement. I see AI as an enablement tool. Yes, there will be some job loss, but mostly in the tactical, repetitive work HR is bogged down with today.

The biggest thing to remember: AI is a mirror of us.

• If we don’t have the skills → AI won’t have them
• If we’re biased → AI will be biased
• If we struggle with communication or collaboration → AI will too

Now more than ever we have to embed an ever-learning mindset across the entire employee lifecycle.

Shifting HR from Cost Center to Revenue Driver 

(00:04:23 – 00:07:02)

I’ve been in HR a long time, and this is our opportunity to stop being seen as operators and start being seen as revenue drivers.

Turnover is baked into most budgets. If you had 20% turnover last year, that cost is already in this year’s plan. Even reducing turnover by 5% can save (or redirect) millions that can fund real learning.

If only 50% of your organization has the skills to do their job well, you’re only ever going to get 50% return.

Real-World Example: Constant Contact Turnaround 

(00:07:02 – 00:09:35)

At Constant Contact we had ridiculous churn in sales, customer support, and technical roles — close to 40% turnover and average tenure around six months.

We took a step back, looked at the data (engagement surveys, performance management, manager feedback), and the top gaps were always: communication, collaboration, and change management.

We invested ~$250K in targeted coaching and development. Result?

• Turnover dropped dramatically
• Average tenure went to over 1.5 years
• We exceeded revenue goals by millions
• Ramp time for new salespeople dropped from 6 months to ~4 months

That $250K investment turned into multi-million-dollar returns — and HR went from cost center to revenue driver.

The Evergreen Change Plan I’ve Used My Entire Career 

(00:09:35 – 00:12:07)

Here’s the step-by-step framework I use for any major change (upskilling programs, reorgs, acquisitions, etc.):

1. Diagnose the need (look at the data — turnover cost, revenue missed because of skill gaps)
2. Collect input, especially from middle managers
3. Create “What’s in it for me?” buy-in with employees
4. Build an informal change team (middle managers + engaged employees)
5. Secure executive sponsorship with hard numbers
6. Define clear success outcomes
7. Communicate constantly and connect development directly to roles/goals
8. Celebrate early wins and expand
9. Make it evergreen — apply the cycle to onboarding, promotions, new managers, everything

Pearson Education Example: From Crisis to Culture Shift

(00:16:40 – 00:19:02)

At Pearson we were shifting from publishing to e-learning overnight, acquiring 12 companies, constant reorgs. We had great plans but zero employee buy-in.

We finally stepped back, brought in coaches focused on the exact gaps the data showed, and started connecting development to real goals and roles.

Once people saw the personal benefit and the revenue impact, resistance melted and we started getting 2-3× returns on the investment.

Handling Resistance — The Stoplight Framework 

(00:30:09 – 00:33:11)

Think of your people as a stoplight:

• Green = growth mindset, ready to go (rare)
• Yellow = unsure, too many unknowns (most people)
• Red = fixed mindset, resistant (have the hard conversation — if they won’t turn green, they may need to go)

Example: A high-performing sales leader hitting goals but burning through people left and right. When we added up the true cost (turnover, rehiring, lost productivity), he was actually costing the company millions more than the revenue he brought in. Data made the conversation undeniable.

Q&A Highlights 

(00:35:59 – end)

How do you actually get budget and executive buy-in?

Show them the money. Speak dollars, not “engagement.” Start small (sales/CS usually), deliver quick wins, then expand.

How did you fund the $250K with millions in turnover cost?

I went line-by-line through the budget: killed unused systems, reclaimed HR dollars sitting in other leaders’ budgets (recruiting, tuition reimbursement barely used, even $10K allocated for stamps!), and reallocated.

How do you get middle-manager buy-in when they don’t control budget?

Middle managers are desperate for help. They’re overwhelmed and know their teams are suffering. Position them as change champions — give them the tools so they stop running around with their heads cut off.

Anything we should do to prepare for more AI in HR?

Skill your people first. AI is a mirror. If your people lack communication, collaboration, or critical thinking, AI will just amplify the mess. Build the human foundation first.