The Leader’s Dilemma: Discernment in Complexity

In today’s newsletter, I want to take you on a journey—part fable, part analysis, part reflection—into a situation I’ve seen far too often. Maybe you’ve been here too.

Three people. Three roles. Three levels of power.

At the top, the Leader.

Somewhere beneath them, the Accused.

And then the Complainant.

The power here can be obvious—a role, a title, the org chart. But it can also be subtle: gender, personal influence, financial leverage, social capital. A Complainant makes the Leader aware of concerns they have about the Accused’s behaviour. And the Leader now carries the weight of response.

I’ve been in this triangle from different perspectives. I’ve watched leaders wrestle with it, worked on cases shaped by it, and years ago researched it for my Master’s thesis. Back then, I focused on naming the challenge and unpacking the many complexities a Leader must discern. Since then, when I share it, I tend to get one of three responses: a knowing nod, a personal story, or the inevitable question—So what’s a Leader to do?

There’s no single answer. But over the years I’ve picked up a few helpful insights that can shed light on all three perspectives.

The truth is, it’s rarely simple. Relationships skew our perceptions. The Accused aren’t always the villains we imagine. Leaders can get stuck—and the way they respond shapes the outcome for everyone. Yet, when handled well, these moments can also become opportunities for growth and change.

In this series, we’ll explore the dilemma from multiple angles. We’ll notice what’s often overlooked. We’ll consider what’s truly at stake. And we’ll reflect on how the journey itself can grow our antifragility and make us more resilient.

Clive

Clive moved around like a ghost. A company he had once felt deeply aligned with—connected to and passionate about—was shifting towards a disillusionment. He couldn’t quite pinpoint when it had happened. There were some key moments, but the colour seems to have faded slowly over time. He feels like he’s done everything he can to change his undesirable circumstances, but with his supervisor, Deya, it feels like he’s hit a wall.

He can’t quite distill it to one thing, in fact, it’s quite tricky to grasp. It’s taken him months to come to terms with the patterns himself. He’s not even sure when it first started, but something shifted in him when his boss shared a new idea from Deya. Clive was taken aback—not because he disliked the idea, but because it was his.

Assuming it was a misunderstanding, he went to Deya to ask her why she hadn’t given him credit. She said she had no idea what he was talking about.

It all went downhill from there. Deya talked over people in meetings, managed Clive with shame when he made mistakes, and she didn’t create any space for Clive to name what he was experiencing. Clive has tried to ignore it, but he’s realizing he might not be the only one that feels this way. Others from the team are starting to bristle, and Clive wonders if he should say something. When he finally raised a few patterns with her, she looked at him like he had three heads—defending herself and explaining away each situation. She seemed unaware of her impact and uninterested in change.

Deya

Deya had promised herself this job would be different. No one would see her as weak. In past roles she’d been overlooked, talked down to, second-guessed. Not here. Here, she’d be decisive. Bring bold ideas. Hold people to high standards.

When Clive approached her, she was blindsided. She didn’t remember the idea he was talking about—maybe it came up in a brainstorm, maybe she thought of it on her own. Either way, it seemed petty. Now, things felt tense, and she certainly didn’t have time to babysit egos.

Grant

When Clive came to Grant about Deya’s behaviour, he was caught off guard. He encouraged Clive to talk to Deya directly, but it seems as though he’s tried that with no success.

Overseeing Deya, Grant observed that she had always been professional and competent—exactly the kind of leader who got results. She’s also taken a lot off his plate. It was true that Grant hadn’t overlapped with her a ton, but he hadn’t seen anything close to what Clive was describing.

Still, Grant had noticed a change in Clive. He wasn’t himself, and he worried this would start to effect team morale.

Honestly, it would be much easier if they could just deal with it without Grant needing to be involved at all, but it seemed past that point. Like it or not, this was now Grant’s problem.

The Leader’s Dilemma

When a leader is faced with this complexity, a number of relevant questions might stir:

Who gets to decide what behaviour is harmful?

What if I don’t see the situation the same way?

How do I get clarity on the concerns?

What do I do?

These questions, among many others, can fill your mind and there are no easy answers. There’s no easy formula. In fact, you don’t want one—every situation is unique. What leaders need are more tools of discernment.

Many people who have felt negatively impacted from one person’s behaviour get to a place where they feel helpless. In this scenario, it’s Clive fulfilling the role of the Complainant. The Complainant tries to address it themselves, but are met with defensiveness from the Accused (Deya). Sometimes the Complainant gets an acknowledgement, but nothing changes. Their concerns may feel appeased, but only for a moment and then the patterns of behaviour continue.

The Accused holds some form of power over the Complainant—formal or informal. And now the Complainant seeks support from someone with authority over the Accused.

This is where the Leader steps in—not only responsible for people in their charge, but also shaping the culture of the whole organization.

The Complexity

Any Leader who has been put into this position, knows that nothing about this scenario is straightforward. The negative reported behaviours often fall outside of clear rules, laws, or any definitive measurement for that matter. They might violate your organizational values, but then even that’s subjective. Not the values themselves, but who’s experience of this person “counts” in determining how to respond?

The behaviour in question is typically patterned over a period of time. It’s not responding to one incident, but a series of incidents that have persisted. Which gives you more data points, but it also makes the concerns somewhat elusive. There isn’t one particular incident that is serious enough to take action, which allows the Accused to explain away and provide excuses for any example that is provided. It’s the culmination of the behaviours that is to be measured and responded to. But this in and of itself presents a problem—to notice the issue it can takes months, maybe even years, and at this point the damage is often so far gone, that by the time it gets to the Leader it’s that much more intractable and complex.

A Common Misstep

Grant listens to Clive and is empathetic.

He asks if Clive has brought his concerns to Deya, and is surprised to learn how Deya responded. Grant thinks to himself, that seems unlike her.

Clive is hopeful, now that Grant sees and understands, things will finally change.

When Grant follows up with Clive the following week, Clive’s enthusiasm wanes.

Relieved, Grant reports back:

Deya didn’t intend to have this effect on you! She truly didn’t mean it. She said that it’s all a misunderstanding.

But Clive is deflated. Without ownership or clarity on what needs to change, he doesn’t believe anything will. Clive thinks to himself, does Grant think all of Deya’s behaviours are just forgiven? Are they in the past and I’m expected to just move forward?

In the month since Clive talked to Deya, there was a bit of reprieve, but only because he was walking on eggshells. And she was probably holding her breath. What evidence do we have that anything will change?

What’s Going on for the Leader

It’s at this point where the Leader can lose the plot. Good intentions are part of the equation, but if you truly want to know how your organizational culture is being impacted, you have to note the impacts.

When this behaviour is brought to the attention of the Leader a few things may happen for them.

Often, the Leader hasn’t experienced the same behaviour themselves. They may even admire the Accused’s competence. Because they are in a position over this individual, the power differential is in the Leader’s favour. Naturally, they give them the benefit of the doubt.

But this still poses a dilemma for the Leader because while they may not share the same opinion of the Complainant, if they trust the Complainant, then if what they are saying is true, that presents a problem for the Leader. They cannot willfully blind themselves to the reality that they are now aware of, and tasked with responding to.

If the Leader does nothing, they could not only lose the Complainant, but allowing the negative behaviours of the Accused to continue will also have an impact on the broader culture of the organization.

So who holds the truth? And what are our options? What is the Leader to do?

Shift from Referee to Gardener

Leaders often feel the pressure to act like referees—making quick calls about who’s right and who’s wrong, often with incomplete information. This snap-judgment mode carries the burden of instant certainty when there’s much to unpack and consider.

A more helpful analogy would be for a Leader to adopt the role of a gardener.

Gardeners consider the whole ecosystem. They assess symptoms, trace root causes, and decide when to leave things be, add nutrients, or do some pruning. They make decisions for the long-term health of the garden.

Faced with a complaint, the Leader’s question shifts from “Who’s right?” to “What needs to happen, and what information is needed to discern the way forward?

Rather than going to quick answers, Leaders can hold the tension by initiating a process of discovery.

We’ll pause here for now, and we’ll come back to this dilemma and exploring some of the elements a Leader can discern.

In the meantime, I’m curious—have you experienced this dilemma? What resonates? What were some of the complexities you faced?