Working with Difficult Personalities Without Losing Yourself as a Leader

Over the years, I’ve learned the hard way that I can’t “nice” my way out of every difficult interaction. It’s rare, but some people are beyond the reach of a good-faith effort. In those cases, I have to adjust my approach — or risk creating more problems for my team, my institution, and myself. That’s a hard pill to swallow.

Higher education is inherently relational. Most of us come into this work because we care about people — our students and our colleagues. But not all people are easy to care for.

Not every difficult interaction means someone is a “difficult person.” People have bad days. But sometimes what we’re experiencing is part of a pattern — behavior that is chronically problematic, and at times described as “toxic” or “narcissistic.”

For me, the hardest moments are when those patterns challenge my values. The issue isn’t just that difficult personalities exist — it’s that they test how we lead.

Why Working with Difficult Personalities Is So Hard for Heart-Led Leaders

Heart-led leadership prioritizes compassion, dignity, and relational care and tends to value relationships. It helps create environments where people feel psychologically safe, supported, and empowered to realize their potential. But that same inclination — to prioritize kindness and avoid harm — can also put leaders at risk.

When these leaders are working with particularly difficult personalities, they are more vulnerable to over-accommodating, avoiding conflict, and in some cases, interpreting intentional harm as a simple “misunderstanding.” Worse, when leaders forget that niceness is not the same as kindness and when they prioritize their desire to be liked over the obligation to make hard decisions, they can slip into distorted judgment and might delay necessary action.

Staying Grounded and Empathetic

So, how do we remain compassionate, authentic, empathetic, and kind when working with people who are persistently difficult — or even harmful?

To get to the answer, it might be helpful to first draw from psychological literature to understand the more problematic personalities out there. Understanding the pattern does not mean excusing it; it allows us to respond strategically.

Psychologists often point to three personality patterns that can be especially challenging in the workplace:

Narcissism – entitlement, grandiosity, and fragile self-esteem Machiavellianism – manipulation and strategic self-interest Psychopathy (subclinical) – low empathy and comfort with harm

They are often described colloquially as “toxic” and, in combination, they are collectively known by psychologists as the dark triad.

It’s important to note that these traits exist on a spectrum. Most people may show some of these tendencies at times — especially under stress. Occasionally, difficult behavior is quite manageable, but persistent patterns and clear impact can be daunting to navigate.

According to Ramani Durvasula, Ph.D. — clinical psychologist, author, and expert on narcissism and high-conflict relationships — the majority of people who have narcissistic traits do not have an actual psychiatric disorder (e.g. narcissistic personality disorder). While clinical diagnoses are relatively rare, narcissistic traits are far more common in everyday interactions.

Specifically, the behavior is characterized by key patterns-lack of empathy, entitlement, grandiosity, superficiality, arrogance, admiration seeking, difficulties with emotional regulation, a propensity to envy, and difficulties with self-esteem regulation. Building a relationship with difficult personalities such as these is challenging because they can be immune to kindness.

But the good news is that psychologists have advice for navigating these relationships, and much of the advice suggests a pathway that is rooted in compassion and care — for both the difficult personality and for oneself. Below are some strategies gleaned from psychologists and tailored to the heart-led leader.

Boundaries are not a betrayal of heart-led leadership — they are an expression of it.

The most important advice is to emphasize boundaries and self-preservation. You can express care for someone without giving them unlimited access to your time, energy, or emotional bandwidth.

The key, then, becomes managing your expectations, setting healthy boundaries, and enforcing them. Identify your hard lines and enforce them. Do not make excuses for their behaviors, or your own, and do not compromise your values. Do not engage when you don’t need to. You can limit your exposure. Remind yourself that your tolerance for toxic behavior is not unlimited.

We can stick to kindness but lean into boundaries. Our commitment to care includes protecting others from harm, and we re-commit to holding others accountable.

For heart-led leaders, this might feel like giving up on a person. It might feel like giving up hope. As Durvasula reminds us, this is not about giving up hope but reframing it: “It’s more like a re-rendering of hope. It’s re-writing that hope in a way that’s less about trying to run around in circles and trying to please one person, but really embedding it in your larger version of being again, a compassionate person yourself.”

Lead the Interaction, even if the person won’t be led.

Difficult people will resist your efforts to bring them into the fold. You can’t change this person, but you can always structure your interactions with them. Lean into your inclination to shape norms in your organization with a leadership style that is clear and consistent. Your interactions with difficult people necessitate clarity and consistency. You can set agendas and, more importantly, stick to them. In 1:1 and in group or team meetings, do not hesitate to interrupt unproductive behavior, confidently and calmly. Do your best to call out harm, name the impact in a way that does not escalate emotion. Try using phrases such as: “I want to make sure this conversation stays focused on…” “That approach isn’t going to work for this team…”

Leverage that collective support — tap into your network.

Cash in on all that capital you have built by developing trusting, collaborative, and collegial relationships across campus. Remember that leadership is not an individual survival exercise. Difficult personalities thrive in isolation and ambiguity; talk to your mentors and trusted colleagues. Share your challenges and bounce ideas off each other. Share context and patterns — not gossip. Stick to observable behaviors and avoid over-interpreting intent. Talk to your team about your goals for establishing and reinforcing healthy norms, without throwing this particular person under the bus. You might be surprised by the extent to which your team can help you reinforce positive norms.

Know when the most ethical choice is to cut ties.

At some point, you have to acknowledge your emotional and psychological limits. Not all relationships can be repaired or transformed. You will need to consider ending the relationship and official forms of distancing this person from your team and from yourself. Hold to your values and integrity, and be reassured that creating distance (by reassigning this person or parting ways completely) is not failure. It is tough love, and an act of compassion.

Ultimately, kind leaders should not be endlessly accommodating, especially with particularly difficult people. It is about being principled — so that even in the presence of difficult personalities, you do not lose your clarity, your boundaries, or your sense of who you are.