Earlier this week, I met with a small group of HR directors, business owners, and economic development folks. Someone shared a story that perfectly captures the foundational skills gap we're facing.

A company was trying to schedule an interview with a Gen Z candidate. To make it convenient, they sent a Calendly link so the candidate could pick any time that worked for them.

The response? A harsh message saying essentially: "I'm not your secretary. I refuse to take my time to schedule a time that works for you."

The millennial interviewer was stunned. From their perspective, they were being gracious—letting the candidate choose instead of imposing a specific time. From the candidate's perspective, they were being asked to do administrative work that wasn't their job.

Both people thought they were in the right.

Here's what made it worse: this wasn't a values mismatch or a generational complaint. This was a qualified candidate who genuinely didn't understand professional norms around scheduling. Nobody had ever taught them that "pick a time that works for you" is a courtesy, not a burden.

The candidate didn't get the interview.

Someone at the table asked: "How can they not know this stuff?"

Silence.

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The Gap Everyone Sees (And No One Fixes)

Here's what I'm seeing across multiple contexts:

Employers are consistently observing gaps in conflict resolution, team leadership, and basic professional communication. These aren't occasional edge cases; it's endemic. And as you know, foundational skills make the difference between someone who can do the work and someone who can lead the work.

In my research for a workforce development article (coming out in the Springfield Business Journal soon), I found data showing AI is eliminating entry-level positions that used to teach these skills. The traditional path—start at the bottom, learn from mistakes, get promoted—is collapsing. Companies now expect people to show up on day one with leadership skills they never had a chance to develop.

And in conversations with product professionals like you, I hear constant frustration: "I know what needs to happen, but I can't get my team to execute." "My boss keeps overriding my decisions." "I'm spending half my time in meetings trying to get alignment."

These aren't technical problems. They're people problems.

What Makes This Hard

The Calendly story isn't really about Gen Z versus Millennials. It's about what happens when foundational professional skills aren't taught systematically.

The candidate probably wasn't trying to be difficult. They genuinely didn't know that scheduling flexibility is standard professional courtesy. Nobody taught them. And now they lost an opportunity because of a skill gap they didn't even know they had.

This is happening across the board. The term "soft skills" is terrible because it makes crucial capabilities sound optional, like they're personality traits you either have or don't.

That's not how this works.

Understanding professional norms, reading workplace context, navigating organizational dynamics—these aren't personality traits. They're learnable skills with specific patterns you can practice. Same with conflict resolution, delegation, and giving feedback that actually changes behavior.

But here's the catch: many product professionals never get systematic training in these areas because:

Your degree didn't include it. You learned marketing, or algorithms, or data structures, not how to navigate organizational politics or handle a team member who's underperforming.

Your first few jobs didn't teach it. You were heads-down coding or managing projects, not dealing with complex interpersonal dynamics. And even if you were, nobody showed you the frameworks that make it manageable.

Your promotion didn't come with instructions. One day, you're an individual contributor. The next, you're responsible for people. Good luck figuring it out.

The traditional learning path—make mistakes, eventually figure it out—works. Eventually. But it's expensive. Both for you (career damage from avoidable failures) and your team (constant churn and dysfunction while you learn). And even that traditional path is disappearing for recent graduates.

The Coaching Gap

After that meeting, I kept thinking about the question someone raised: how do we coach younger people to enter the workforce in a healthy manner?

The traditional answer—"learn through experience"—doesn't work anymore. Entry-level positions that used to teach these skills are disappearing. AI is eliminating the work that trained people. Companies now expect day-one readiness for skills people never had a chance to develop.

And here's the harder truth: we can't wait for universities to add this to their curriculum. By the time they do, another generation will have missed it.

The solution has to be more direct. When someone joins your team or enters the workforce:

Name the unwritten rules explicitly. Don't assume they know that Calendly links are courtesy, not admin work. Or that "let's circle back" means "no." Or that disagreeing in a meeting requires specific framing to avoid seeming combative. These aren't obvious. They're learned.

Treat professional norms like technical skills. "Here's how we handle scheduling conflicts in a professional setting" is as teachable as "here's how we handle merge conflicts in Git." Neither is intuitive. Both have patterns.

Provide the framework before the failure. That Gen Z candidate never got the chance to learn. They just lost the opportunity. Better approach: "When someone sends you a Calendly link, that's them being flexible. Pick a time and send a confirmation. Here's why this norm exists."

At the Tech Council meeting, employers mentioned gaps in conflict resolution, handling feedback without defensiveness, and basic professional communication. One person even mentioned hygiene—which sounds trivial until you realize nobody taught that person workplace norms.

These aren't "nice to have" skills. They're make-or-break. And the gap isn't getting smaller—it's accelerating as the traditional learning path collapses.

The Framework Approach

Here's what actually works: treating these "soft skills" like any other technical capability.

When you learned to code, you didn't just "figure it out through experience." You learned systematic approaches. Design patterns. Best practices. Frameworks that gave you starting points instead of forcing you to reinvent everything.

Leadership works the same way.

Conflict resolution isn't "be nice and hope it works out." It's a specific process:

• Separate the problem from the people

• Identify underlying interests, not just surface positions

• Generate options before evaluating solutions

• Use objective criteria to make decisions

Delegation isn't "dump work on other people." It's a systematic approach:

• Match task complexity to skill level

• Provide context, not just instructions

• Define clear success criteria upfront

• Build in checkpoints without micromanaging

Difficult conversations aren't about being naturally charismatic. They're about preparation:

• Clarify what you want to accomplish

• Anticipate their perspective and concerns

• Plan your opening statement

• Practice responses to likely reactions

These are learnable systems. Not personality traits.

Monday Morning Action

Next time someone on your team frustrates you, pause before reacting.

Ask yourself: "Do they lack the skill to do this, or do I lack the skill to explain/delegate/coach it properly?"

Sometimes, it's the second one.

We blame people for not reading our minds about what we actually need. We get frustrated when they can't navigate organizational dynamics we never explained. We expect them to know things we never taught them.

That's not their failure. It's ours.

The good news? Once you treat leadership as a learnable skill instead of a personality requirement, you can actually get better at it. Systematically. Measurably.

You just need the frameworks.

I'm working on something that addresses this gap directly—systematic training in the foundational skills that product professionals need but rarely get taught. More on that soon.

For now: pick one leadership challenge you're facing this week. Instead of hoping it resolves itself, treat it like a technical problem. Break it down. Identify the specific skill you're missing. Find a framework.

And reply to tell me what skill you chose to work on. I'm genuinely curious what gaps you're experiencing most.

Cheers,

Matthew Stublefield

P.S. The article I mentioned about workforce development and AI's impact will be in the Springfield Business Journal in a couple of weeks. I'll share a link when it's out. The data on how fast this is changing is sobering—students graduating this year face a job market that looks nothing like the one three years ago.

P.P.S. Speaking of treating leadership challenges like technical problems: if you've got a difficult boss conversation coming up, don't wing it. Check out that AI practice partner where you can rehearse your approach systematically—test different framings, anticipate responses, and refine your message. You'll also have an opportunity to tell me about your situation, and I'll send you a personalized video. It's the framework approach, applied to your actual conversation. $17. https://fieldway.org/conflictgpt