Issue 004 | October 27, 2026

The Conversation Nobody Wants to Have

THE BRIEF

When I was working in Hong Kong, we were building a regional operation that hadn’t existed in quite the same way before. We were figuring things out as we went, testing approaches, making adjustments, and learning what worked across markets that were very different from one another.

This was around 2013 and 2014, when digital marketing was evolving rapidly. The markets we managed were developing digital behaviors and platforms that looked quite different from those in the West. That created exciting opportunities to approach things differently, but it also meant we could make mistakes very quickly, in an environment where those mistakes would be visible.

One of our early decisions was who should lead the digital work. We hired someone locally because we recognized that understanding the market was essential. We needed expertise grounded in the realities of the region, not simply someone who could replicate what had worked in the United States.

It was a reasonable decision. But in our focus on finding the right person, we overlooked something fundamental.

We hadn’t clearly established who owned the communication, who was responsible for writing it, and who had final approval.

As the work progressed, those unanswered questions began creating friction. Different people had different responsibilities, expertise, and expectations. The digital function understood the local landscape. Brand leadership had responsibilities for protecting the brand and its messaging. Both perspectives mattered.

But we hadn’t defined how those responsibilities were supposed to work together.

Instead of spending our energy learning, experimenting, and moving the business forward, we found ourselves dealing with disagreements about who had the authority to approve copy.

Looking back, what stands out isn’t that we had disagreements. We were operating in a changing environment, and disagreement was inevitable.

What stands out is how difficult it was to have the conversations that could have helped us establish a better way of working.

THE COST OF WHAT GOES UNSAID

When something isn’t working, it’s tempting to focus on the people involved.

We might conclude that someone is overstepping, refusing to collaborate, or making decisions that aren’t theirs to make.

And sometimes those concerns are legitimate.

But before we decide that someone is the problem, we should ask whether the organization has created the conditions for people to work together effectively.

In Hong Kong, we were navigating different areas of expertise, competing priorities, and responsibilities that hadn’t been clearly defined. Those were real operational challenges. Communication alone couldn’t resolve them.

But communication was essential to identifying what needed to change.

We needed conversations about decision rights, responsibilities, and how the process should work. Instead, too much of our attention went toward managing the friction that resulted from not having those conversations.

This is something I think leaders encounter more often than we realize.

A team struggles with repeated delays, so people begin questioning one another’s commitment. Two departments disagree about a decision, and the conversation becomes about who has more authority. Someone pushes back on a request, and others interpret it as a lack of collaboration.

Sometimes the underlying issue is a person’s behavior. Sometimes it’s a resource constraint, a competing business priority, or a process that was never clearly established.

The challenge is that we don’t always stop to find out.

And when we avoid the difficult conversation, we can end up assigning blame before we’ve understood the problem.

DIRECT DOESN’T HAVE TO MEAN HARSH

I think one reason leaders hesitate to raise difficult concerns is that they associate directness with confrontation.

They worry about challenging someone else’s authority, damaging a relationship, or creating tension between people who still need to work together.

Those concerns are understandable, particularly in cross-functional environments where nobody has complete authority over everything that needs to happen.

But there is a difference between challenging a person and challenging a way of working.

Imagine approaching a colleague and saying, “You keep making decisions that aren’t yours to make.”

The concern may be real, but the statement immediately puts the other person in a position of defending their actions.

Now consider a different approach:

“We seem to have different understandings of who has final approval over this work. It’s creating delays, and I think we need to establish a process that reflects both the local expertise and the brand responsibilities. Can we work through how those decisions should be made?”

The second approach doesn’t avoid the disagreement. It names it.

But instead of assuming that one person is the problem, it identifies what needs clarification and invites the other person to help establish a solution.

That’s the distinction I wish I had understood more clearly earlier in my career.

Having a difficult conversation doesn’t mean walking into the room ready to prove that you’re right. It means being willing to name what isn’t working, understand the different perspectives involved, and propose a way forward.

You can acknowledge someone else’s expertise without abandoning your own responsibilities.

You can challenge an existing process without attacking the people operating within it.

And you can be clear about what needs to change without pretending you already know everything about why the problem exists.

Of course, not every difficult conversation will lead to agreement. Some decisions require a leader to establish authority, resolve competing priorities, or make a call that not everyone supports.

But even then, the conversation becomes more productive when people understand what is being decided, why it matters, and how they are expected to work together.

TRY THIS

The next time you find yourself frustrated by a recurring issue, resist the temptation to begin with what someone else is doing wrong.

Before having the conversation, consider three questions.

1. What have I actually observed?

Separate the facts from your interpretation.

“We’ve had three disagreements about who approves the final communication” is different from “Nobody respects my authority.”

The first gives you something concrete to discuss. The second assumes you understand the other person’s intentions.

2. Why does this matter?

Identify the impact on the work.

Are decisions being delayed? Are people duplicating effort? Are unclear responsibilities creating unnecessary revisions? Is the team spending time resolving internal disagreements instead of serving the customer?

When you explain the business consequence, you help move the conversation beyond individual frustration.

3. What do I still need to understand?

Consider the other person’s perspective before deciding what the solution should be.

What responsibility are they trying to fulfill? What information or expertise do they have that you might be overlooking? Is the issue a disagreement about priorities, or has the organization simply failed to establish who decides?

Then use what you’ve learned to propose a way forward.

That last step matters.

The objective isn’t simply to raise the concern and hope someone else fixes it. It’s to help turn the conversation into a decision about what should happen differently.

You might say, “Here’s what I’m seeing, here’s how it’s affecting our work, and here’s what I propose we clarify. What am I missing?”

It’s a different starting point from blame, and a more useful one for making progress.

THE CONVERSATION WORTH HAVING

When I think back to that experience in Hong Kong, I don’t think the answer was to eliminate disagreement. We were working across markets, functions, and areas of expertise that were changing rapidly. Different perspectives were part of what made the work valuable.

What we needed was a clearer way to bring those perspectives together and make decisions.

Had we established those conversations earlier, we might have spent less time debating approval responsibilities and more time learning from the market, improving our work, and moving forward.

That’s one of the lessons I’ve carried with me about leadership.

The ability to communicate effectively isn’t just about presenting ideas well or explaining decisions clearly. It’s also about recognizing when an uncomfortable conversation needs to happen and having the judgment to approach it constructively.

Think about a recurring frustration in your own work.

Is the problem really the person you’ve been frustrated with? Or is there a responsibility, expectation, decision, or process that nobody has clearly addressed?

And if that conversation hasn’t happened yet, what would it look like to initiate it with facts, curiosity, and a proposed way forward?

Sometimes the conversation nobody wants to have is the one that allows everyone to stop working around the problem and start addressing it.

Until next time,

Natasha ​
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