Over the past two weeks, I've been messaging product professionals and leaders on LinkedIn with a simple question: "What's your biggest leadership challenge right now?" The response has been overwhelming—dozens of thoughtful replies from people across industries, company sizes, and experience levels.

What emerged from these conversations wasn't surprising, but it was illuminating in its consistency. The same challenges kept appearing in different words: delegation anxiety, managing up confusion, team dynamics frustration, and that persistent feeling of "I have no idea what I'm doing as a leader."

But first, let me tell you about an upcoming free webinar I'm hosting.

If you're dealing with executive burnout—or supporting leaders who are—I'm hosting a free 45-minute session on September 10th at 2 PM CT called "The Executive Burnout Recovery System." I'll share the three hidden signs of burnout that most leaders miss and the systematic approach I use to help executives recover their energy while actually improving team performance. You can register at https://fieldway.org/events/webinars/2025-09-10/burnout

Now, back to what I learned from all those LinkedIn conversations.

The Transition Nobody Prepared You For

The most consistent theme wasn't about specific skills or techniques. It was about the fundamental shift from being really good at building products to being responsible for building people. As one director put it: "I was promoted because I was excellent at shipping features. Now I'm expected to develop humans. No one taught me how."

This resonates with research showing that 60% of newly promoted managers fail to meet expectations in their first two years—not because they lack technical skills, but because the competencies that made them successful individual contributors are fundamentally different from those required to lead teams effectively.

Through these conversations, I identified five critical areas where newly promoted leaders consistently struggle:

1. Managing Up and Stakeholder Communication

I can explain technical decisions to engineers, but when I talk to executives, I feel like I'm speaking a different language.

This was mentioned by many who responded. The challenge isn't just translation; it's understanding what senior stakeholders need to know, when they need to know it, and how to influence outcomes when you don't have direct authority over decision-makers.

The technical leaders who succeed here learn to think like business leaders while maintaining their technical credibility. They become translators between technical realities and business needs, building trust through consistent follow-through rather than technical expertise alone.

2. Delegation and Team Development

I know I should delegate more, but it's faster if I just do it myself.

The math seems simple: training someone takes two hours, doing it yourself takes 30 minutes. But that math ignores the compound cost of continuing to do work others could handle.

The leaders who break through this work on what I call "development thinking. They measure success by their team's growing capabilities rather than their personal task completion, and they invest time upfront to create leverage later, eventually spending more time on strategic work that only they can do.

3. Impostor Syndrome and Confidence Building

Sometimes I feel like everyone's going to figure out that I don't actually know what I'm doing.

This appeared in about 20% of the conversations, often accompanied by anxiety about high-visibility presentations or strategic discussions. The technical background that brought them to leadership can actually make this worse—they're used to having clear, objective answers, but leadership decisions involve ambiguity and competing priorities.

The most effective approach I've seen combines acknowledging what you don't know (which builds trust) with decisive action on what you do know (which builds confidence). Leadership confidence grows through the accumulation of small wins rather than a sudden transformation.

4. Boundary Setting and Sustainable Practices

I'm working 60-hour weeks and my team is starting to do the same.

New leaders often try to handle both their leadership responsibilities and continue doing individual contributor work. This creates unsustainable patterns that eventually affect team performance and morale.

The solution requires both personal boundary setting and systematic delegation. Leaders need to model sustainable work patterns while building team capabilities that don't require their constant involvement.

5. Strategic vs. Tactical Thinking

I spend all my time fighting fires and never get to the strategic work I'm supposed to be doing.

Perhaps the most challenging shift is from executing tasks to thinking about systems. Individual contributors solve problems; leaders create conditions that prevent problems or enable others to solve them.

This requires a fundamental reframe from "what should I do?" to "what should the team be capable of doing?" and from "how do I solve this?" to "how do we build systems that handle this type of challenge?"

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Why This Matters Now

These aren't just individual career challenges—they're organizational imperatives. Research shows that 52% of Gen Z professionals actively avoid middle-management positions, creating a leadership capability crisis in many organizations. The people who successfully navigate this transition have significant competitive advantages.

Organizations with effective leadership development see teams that are 27% more likely to exceed goals and achieve 1.5 times higher performance rates. But most companies don't provide systematic support for this transition, leaving newly promoted leaders to figure it out through trial and error.

What's Coming Next

I'll be diving deeper into each of these five areas in upcoming newsletters, sharing specific frameworks and strategies that address the real challenges product leaders face. These won't be generic management theories—they'll be practical approaches tested with teams achieving 2-3x productivity improvements.

The research is clear: leadership development is a multi-year journey requiring both structured learning and experiential practice. But the right frameworks can accelerate development significantly, helping leaders avoid common pitfalls while building capabilities that create lasting impact.

Looking Forward

If you're navigating this transition yourself, you're not alone in feeling unprepared. Many leaders I spoke with shared moments of uncertainty, frustration, and that persistent question: "Am I doing this right?"

The answer is that leadership effectiveness develops through systematic practice, honest feedback, and willingness to serve others while you're still learning. The specific skills can be developed, the frameworks can be mastered, and the confidence can be built—but only through consistent application and reflection.

You're not just becoming a manager. You're becoming someone who multiplies the capabilities of others, creates opportunities for growth, and builds the kind of workplace culture that attracts and develops the best people.

That's work worth doing, and work that you can learn to do well.

Don't forget to register for the Executive Burnout Recovery System webinar on September 10th at 2 PM CT. Whether you're experiencing burnout yourself or supporting leaders who are, I'll share practical strategies for maintaining leadership effectiveness while recovering energy and focus.

Register at https://fieldway.org/events/webinars/2025-09-10/burnout

Until next time,

Matthew