The manager problem that won't go away with Melinda Wolfe, former CHRO, Bloomberg, Pearson, and GLG.

"We're asking more of managers with fewer resources," notes Wolfe. Recent economic shifts have refocused companies on performance, and that's not sustainable without better support.  

Managers are now expected to be player-coaches: deliver results, develop people, and lead through volatility. When those moments go wrong, the costs ripple: broken trust, bad decisions, legal exposure, or disengaged teams.

Melinda Wolfe, a longtime CHRO at companies like Bloomberg, Pearson, and GLG, has seen the pattern repeat. She now coaches executives and advises organizations on building people-first cultures, and believes we're entering a moment of opportunity. In a recent conversation with Alexei Dunaway, Founder and CEO of Pinnacle, she shared why this challenge persists, how company culture shapes AI adoption, and what it takes to build momentum and trust around AI-powered solutions.

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Why manager training keeps falling short

Wolfe calls it the “permafrost layer”: mid-level management where momentum often stalls. “We’ve tried to fix it in so many ways,” she says, “classroom learning, strategic HR business partners, better senior role models. But none of it meets the moment managers actually need help.”

That’s the crux of the issue: traditional training targets the 10% of learning that happens formally, rather than the 70% that occurs on the job. Managers rarely need help in a workshop—they need it when preparing for a tough 1:1 or in the middle of a team conflict. When those moments go wrong, the costs ripple: broken trust, bad decisions, legal exposure, or disengaged teams.

AI-enabled coaching tools, if designed well, can meet that moment. They offer managers guidance in context, not just content. As Wolfe puts it: “It makes it easier not to make mistakes. And it gives you frameworks to think through problems before you act.”

Culture makes or breaks adoption

Why haven’t more companies jumped in? Culture, Wolfe argues, plays a decisive role.

She compares her time at Bloomberg—private, tech-forward, insular—with Pearson, a massive global education company, and GLG, a millennial-heavy firm with a startup feel. “Some companies are eager to experiment. Others wait until their existing platforms catch up. It depends on the company’s DNA.”

That DNA matters for AI adoption, too. Startups may move fast but lack guardrails. Large enterprises are often better resourced, yet slower to act. Wolfe’s advice: don’t wait for perfect alignment, start where the need is highest. “When it comes to helping first-time or mid-level managers, the risk of doing nothing can be just as high as the risk of trying something new.”

Why AI for managers matters more than ever

Too often, AI pilots prioritize analytics or recruiting—functions that feel safer or more mature. But Wolfe believes manager coaching is a more urgent use case. Not only is the pain point clear and widespread, but AI’s value is immediate. She suggests that if  we can finally democratize coaching, make it specific, timely, and integrated into real workflows, we solve one of the most chronic issues in the modern workplace.

How to bring others along

Wolfe’s playbook for internal buy-in is pragmatic:

1. Make the business case. Use survey data, internal feedback, and performance trends to show why manager enablement matters. “Everyone knows it’s a problem. You just have to prove it’s also a priority.”
   
2. Partner with IT early. Understand their concerns: data privacy, integration, and risk. They’ll be your best allies if they’re brought in, not surprised.
   
3. Anticipate objections. Be ready for skepticism. “You need to know what the naysayers will say and be equipped with answers.”
   
4. Run demos with senior leaders. Let them experience the value firsthand. It’s the fastest way to move people from curious to convinced.
   
5. Create traction from the inside. Start small, with a team or department that’s eager to experiment. Use their success to fuel broader adoption.
   

Final word: Start where it matters most

Wolfe is clear: now is the time to act. “If we have an innovation right now, then it’s incumbent upon us as HR leaders to show our companies an economic and effective way to help managers.”

She’s particularly energized by solutions like Pinnacle—tools that give managers real-time support and coaching in the flow of work, not just abstract advice after the fact. “We haven’t had the people power to provide this level of guidance. Now we finally do and it’s scalable.”

For organizations tempted to wait on incumbent vendors to catch up, she offers a warning: “It’s almost like throwing good money after bad. Why settle for a subpar add-on when a purpose-built solution is already driving value?”

The bottom line? Leaders don’t need to wait until everything is figured out. Trying something small, specific, and impactful is often the smartest move.