The Square Peg Month: Notes From a Leadership Transition

In the past six weeks, I’ve taken on leadership responsibility for six new publications created by two different pairs of retiring founders and publishers.

The business models could not be more different. One is a digital magazine and newsletter. The others are printed publications. Their revenue structures, production rhythms and day-to-day mechanics have almost nothing in common.

And yet, the challenges I’m experiencing across all of them are strikingly similar.

That’s because this isn’t about format or medium.

It’s about this moment in time, when deeply engaged founders step back and new leadership steps in.

Across these organizations, I’ve found myself navigating the same tensions again and again:

• Systems being mistaken for control

• Informal communication obscuring decision-making

• Heroic individuals compensating for underbuilt processes

• Boards and founders still operating as executors rather than governors

After a month of feeling like a square peg, I’m clear on something important: This isn’t a personal fit problem. It’s a structural one.

Scene One: The Tool That Was Never About the Tool

Early on, I suggested using Asana to manage story budgets and workflow.

Not to control editorial content.
Not to rewrite headlines.
Not to meddle in reporting.

Just to replace a growing constellation of spreadsheets, emails and one-off conversations with a shared system so everyone could see what was happening and plan accordingly.

The response from five editors was generally accepting, but there was an undercurrent of discomfort and resistance. The spreadsheets have worked for years, they reasoned. Why change? And why is a shared system where everyone has visibility necessary?

This time, the subtext was unmistakable: I don’t know you, and you feel like a threat to editorial independence.

What’s Actually Happening

This wasn’t about Asana. It was about authority transfer.

Founder-led organizations often run on trust, proximity and shared history. Decisions happen in phone calls. Context lives in people’s heads. Accountability is relational, not documented.

When new leadership introduces systems, even neutral ones, those systems can feel like surveillance or loss of control. In newsrooms especially, where editorial independence is rightly sacred, structure itself can feel suspect.

The outcome if unaddressed:

• Tools become symbolic battlegrounds

• Leaders become emotional shock absorbers

• Editorial independence gets conflated with operational opacity

Scene Two: The Conversations I Can’t See

Across multiple publications, I’ve had the same experience: realizing I’m missing large portions of the organization’s life.

Decisions seem to have already been discussed. Relationships are already active. Communication rhythms exist, but no one can quite articulate them.

Who talks to whom every week?
About what?
How often does the board engage between meetings?
When does editorial loop into operations and when doesn’t it?

I ask to observe before changing anything. That has always been my approach.

But observation becomes nearly impossible when so much happens one-on-one via calls and texts.

What’s Actually Happening

This is communication opacity, and it’s structural, not personal.

Informal communication feels efficient in small organizations. During leadership transitions, it becomes destabilizing.

For a new executive leader, it creates an impossible bind:

• You’re accountable for outcomes

• Without access to inputs

• And judged on decisions you didn’t witness being made

The outcome if unaddressed:

• Frustration mislabeled as “fit issues”

• Leaders burning time reconstructing context

• Trust strained not by intent, but by invisibility

Scene Three: The Brilliant, Exhausted Operator

Every one of these organizations has someone holding the center.

The person who knows how everything actually works.
The one who builds workarounds when systems fall short.
The one who never quite gets to stop.

We pay for tools that should make work easier. Instead, bespoke manual processes emerge to compensate for their limits. The work gets done. The organization survives. The cost is hidden.

Seeing this pattern repeat across very different publications has been sobering.

What’s Actually Happening

This is hero culture masquerading as competence.

Founder-led organizations often survive because extraordinary people compensate for underbuilt systems. It feels scrappy. It feels noble. It’s actually fragile.

The outcome if unaddressed:

• Burnout

• Knowledge trapped in one person’s head

• Organizational paralysis if that person steps away

The fix isn’t gratitude. It’s design.

Scene Four: When Questions Don’t Land

In a board discussion hosted at someone’s home, I asked an open-ended question about meetings and time commitments. I wanted to hear how each board member thought about their weekly involvement, not to schedule anything yet, but to understand working styles and expectations.

The conversation immediately pivoted to locking down meeting dates.

Reasonable. Practical. Also not the question I asked.

I left without the information I needed and with a growing realization that we were operating with very different assumptions about what leadership conversations are for.

What’s Actually Happening

This is a clash between diagnostic mode and execution mode.

Founders and longtime operators are used to solving immediately. New executive leaders need to map the terrain first.

Neither is wrong. But without explicit agreement, both feel blocked.

The outcome if unaddressed:

• Inquiry mistaken for resistance

• Decisions made without shared understanding

• Leaders talking past one another

Why I See This So Quickly

This pattern recognition isn’t accidental.

Before moving into media leadership, I spent 20 years as a technology management consultant for companies like Microsoft, Baxter Pharma and Slalom. I was brought in when organizations felt slower than they should, more stressful than they needed to be or overly dependent on heroic individuals holding systems together with duct tape and goodwill.

My job was to quickly identify operational friction like manual workarounds and duplicated effort, then design systems of work, communication and technology to fix them.

The goal was never efficiency for efficiency’s sake.

The goal was fewer stressed-out people, clear accountability, transparent governance and repeatable processes that didn’t bottleneck around one exhausted human being.

Some of my favorite work was inside Microsoft itself, where over six years I built internal support newsrooms for major products. I studied where information broke down, how employees searched for answers, what frustrated them and how tools failed them. I designed systems that made information work for people instead of people working for the tools.

Those newsrooms were fully digital and distributed, with weekly publishing cadences, built-in reader feedback loops and surge staffing for emergency communications. When a product shipped a fatal bug, the newsroom didn’t panic. It published. It’s the tech version of when a storm comes to town.

That work trained my eye. When systems strain, I notice.

This Moment Isn’t About Fit. It’s About Transition.

After seeing the same dynamics across six very different publications, I’m clear on one thing.

This isn’t about personal fit. It’s about whether organizations truly want to move from founder-centric operation to sustainable governance.

That shift requires:

• Communication visibility by default

• Clear separation between editorial independence and operational accountability

• Systems that protect people instead of relying on them

• Boards that govern rather than operate

These aren’t failures. They’re growing pains. But they don’t resolve on goodwill alone.

They resolve through explicit agreements.

The Outcome I’m Working Toward

What I’m advocating for across all six publications is simple, even if it’s uncomfortable:

• Systems as care, not control

• Transparency so trust doesn’t have to carry everything

• Fewer heroic workarounds, more sustainable design

• Leadership clarity so people can do their jobs without fear or friction

Good journalism depends on strong institutions, not just strong individuals.

And strong institutions are built not in moments of harmony, but in moments where we slow down, name what’s actually happening and choose structures that let everyone do their best work without burning out or battling shadows.

If you’ve ever stepped into leadership during a transition and wondered whether the friction was you, I see you.

Sometimes the square peg isn’t the problem. Sometimes the hole just hasn’t been reshaped yet.