Dealing With Difficult People: A Leader’s Guide

Finding a way forward. 

Some time ago, I was asked if I could help a leadership team learn how to deal with “difficult people”. I followed up by asking “What were you looking for the team to get better at doing exactly?” The answer is not entirely obvious. 

How do we deal with difficult people? It is a legitimate question of course and is one my students and participants repeatedly ask me about — along with how to deal with ‘toxic’ people (more on that later). 

Undoubtedly, some people are more frequently a big challenge to lead or manage for almost anyone. We know that there are employees and colleagues who require more effort to lead.  

However, what we may not know is that ‘difficulty’ may reflect the fact that many employees today are struggling with mental health issues. These would pose significant challenges for those they work with. In 2021, over a quarter of Canadians reported mental health symptoms, and roughly 1 in 10 reported needing professional help. Fortunately, though, emerging leaders are more likely than ever to see that mental health is health. The hope is that this awareness can lead to a more helpful characterization than ‘difficult’.  

But if it is decided that those who are suffering in this way are difficult, would this provide the psychological safety required to openly discuss mental health issues? The research on mental health stigma would indicate likely not. 

Anyone Can Be Difficult

Leaders who have leaned into authenticity know that we all can be difficult from time to time.  We are only human after all. Many otherwise amazing employees can at times pose challenges to leadership efforts. However, most are likely not inherently difficult. Most are likely, deep down, pretty good people. 

So why do authors and experts keep on advising leaders on how to deal with this increasingly nebulous band of difficult people? The term itself — difficult people — provides a frame (i.e., perspective or lens) that makes it easy for us to categorize and put people into boxes. Psychologists call this making dispositional attributions, and it can lead to errors in judgement and unfair and unhelpful frames and categorizations.  

New Frames Needed

If we want to lead successfully, perhaps what we see as “difficult” could be better framed. Maybe it could be seen as what I like to call “learning how to manage someone I have not yet learned about yet”. I have been suggesting that exact frame and observing how it helps leaders be more successful.  

The “frame” is a powerful metaphor for understanding and solving all kinds of leadership problems. Its origin lies in the early work of Mihaly Csikszentmihalyi and Jacob Getzels who noted that the biggest challenge to creative solutions is not the solutions themselves, but figuring out — or framing — the problem itself. 

Many other notable management theorists (e.g. Roger Martin, Chris Argyris, and others) as well as theorists in other fields like sociology (e.g., Erving Goffman), and psychology (e.g., Daniel Kahneman and Amos Tversky) have also studied how new frames bring new questions. And in turn, how new questions can yield novel perspectives and in turn, new solutions. 

“Most people define learning too narrowly as mere ‘problem-solving’, so they focus on identifying and correcting errors in the external environment. Solving problems is important. But if learning is to persist, managers and employees must also look inward. The need to reflect critically on their own behaviour, identify the ways they often inadvertently contribute to the organization’s problems, and then change how they act.” 

– Chris Argyris, “Teaching Smart People How to Learn”. hbr.org. June 1991 

What Does the Research Say?

An examination of the psychological research regarding the nature of a difficult person will be helpful here. There certainly is a widely accepted understanding of what we call difficult in personality psychology. The widely accepted Five Factor Model of personality (FFM) likely sees “difficult people” as those with lower levels of ‘agreeableness’. 

Personality researchers who have looked further into low agreeableness have identified a common characterization of a difficult personality, that being antagonism — or what is sometimes called argumentativeness or hostility. 

We all know someone we find to be antagonistic at work or in our families — they seem to always be ready to pick a fight. Anyone might find this behaviour annoying or displeasing but may not go so far as to believe that it constitutes a diagnostic personality pathology. 

This is unlikely statistically and we likely do not have the data, experience, education, or credentials to draw such an extreme conclusion. So, simply labelling the person who is exhibiting antagonistic behaviour as difficult won’t help you or the other person. 

A Way Forward

It is a good idea to change how the problem of “dealing with difficult people” is framed. Here are some reasons why: 

1) When difficulty is characterized as endemic to a person (i.e., “that person is difficult”), it cannot be simply fixed. Difficulty is not a broken thing in another person. 

2) This frame is judgmental at best and completely lacking in equanimity at worst. It limits our solution pretty much to things like tolerating another, or ‘dealing with’ a nuisance. Who are we to decide that someone else is near-universally “difficult” such that we can call them a “difficult person”? 

3) Modern psychological theory teaches that what we find difficult in someone is often a reflection of ourselves. A focus exclusively on the other won’t help. 

Framing (and reframing) compares a current state to an ideal state. In this case: 

• The current state (problem) = that person is difficult 
• The ideal state (goal) = they need to be less difficult 

A better frame could be: 

• The current state (problem) = I am not able to manage this person 
• The ideal state (goal) = I need to learn how to do better 

Now this could be workable. Not guaranteed successful (what is?), but workable. There are a host of well-known, self-development tools that could be helpful with this new frame. 

A leader could begin by acknowledging that they are having a difficult time and finding resources that they do not currently have to guide them. One example would be looking at one’s level of self-awareness and asking if one has the full picture of the challenges of the difficult person. Then, one could actively question their assumptions by asking: 

“How would I behave toward them if I was sympathetic rather than evaluative? Especially given that I don’t know — and may never know — their story.” 

“Could I slow down? Maybe I would work to find different words, plan myself more purposefully, and consider my approach more carefully.” 

I could also consider that I don’t know anything about the life experience, upbringing, struggles, or day-to-day challenges of this “difficult person”.  

When we are struggling, I imagine most would hope that their less-than-ideal behaviours would be understood by others. And struggle we will. 

How do we “deal with” that difficult person? How could we learn this as a skill? How can a leadership educator teach this to others? 

Like most leadership problems and issues, it serves us all to begin with a helpful frame. If the reason the team is failing is that a member is ‘toxic’, there is no discernable fix. If the reason the conflict happened is because a person is evil, there is little that is possible. 

For people leaders, if a person is framed as ‘difficult’, there is no way forward. There is an alternative though. To bring out the possible, we can change the frame. 

We can look at ourselves as well as the others. We can move to learning and growth. I know that won’t always work, but it’s got to be better than calling them ‘difficult’. 

“You are not a problem that needs solving.” 

– Eckhart Tolle