Dealing With Difficult People at Work: Stoic Strategies by Greg Sadler

As editor of Stoicism Today, each year I ask those who spoke or gave a workshop at the main Stoicon or at one of the Stoicon-X events to provide a piece for our readership, the vast majority of whom cannot attend these events.  Just to put it into perspective, the attendees at Stoicon number in the hundreds.  A big Stoicon-X event might get a hundred.  By contrast most of our blog posts here get tens – and occasionally, hundreds – of thousands of reads.  So when our presenters and organizers are good enough to supply transcripts or summaries  of their talks, workshops, or other activities, I’m very happy to set them here in Stoicism Today.
As a fairly recent addition (joining officially in 2016) to the Modern Stoicism team, I have also  greatly enjoyed participating in Stoicon 2016 and 2017 (and in Stoicon-X Toronto 2017).  At both of those Stoicons, I provided one of the workshops during the breakout sessions.  Accordingly, after having asked many of our speakers to make their own contributions here in Stoicism Today, it is about time for me to put in the work required to add my own piece here about my 2017 Stoicon workshop, “Dealing With Difficult People at Work:  Stoic Strategies”.
If you’d like to see a videorecording of that workshop session, you can do so here.

Structure and Motivation of the Workshop

When Donald Robertson proposed “Stoicism at Work” as the theme for Stoicon 2017, I knew exactly what I wanted to focus on for the workshop.  There are a lot of challenges, irritants, and obstacles that arise within the context of modern work.  Some of the most difficult stem from our interactions and relationships with other people.  I’ve certainly dealt with – sometimes successfully, sometimes less so! – many difficult people in my own career.  And many of my own clients come to me troubled by how to handle these sorts of workplace issues.
I should mention that in its original design, the workshop was a team presentation, with my wife and partner, Andi Sciacca, as my co-presenter.  We designed the workshop together, and had planned to deliver it that way as well.  Unfortunately, due to some health matters at the time, she wasn’t cleared to fly to Toronto.  Given Andi’s qualifications, work-experience, and talents (which would require another blog post to outline), the workshop attendees perhaps got the proverbial short end of the stick with just me presenting!
Clearly difficult people at work was good topic to center upon in workshop format. After all, Stoic philosophy is practical, and should be providing help for people struggling with life-issues. I’d written a post in the series we ran leading up to Stoicon 2017, “Dealing With The Unduly Demanding In the Workplace,” addressing one particular type of “difficult person” – drawing in part on personal experience – and I was looking forward to discussing additional aspects of the workshop with the conference-goers.  As it turned out, the workshop was a big draw.  The room was packed with participants, and they brought some excellent questions, observations, and stories to the session!
The workshop was 90 minutes long, ranged over a lot of material, and included a number of side-discussions, so I am just going to summarize it here, talking about some portions in a bit more detail.
We originally divided the workshop up into the following activities:

  • Discussion – challenges for the Stoic and Stoicism in the workplace
  • Exercise – what main challenges are you encountering?
  • Presentation – several common types of difficult people in workplaces
  • Exercise – your top three difficult persons
  • Presentation – useful Stoic practices within situations involving difficult people
  • Presentation – useful Stoic practices before and after situations involving difficult people
  • Role-Playing Exercises – using Stoic strategies
  • Time Dedicated to Q&A and Discussion

The role-playing exercises would have required both Andi and I, so they were dropped from the actual workshop as delivered.  As it turned out, each part of the workshop drew us into a good bit of discussion, so we used all the time allotted even without those exercises.
The discussions were particularly engaging, I would say, for several reasons.  First, work and the people of the workplace are matters practically everyone can relate to.  As far as I know, there weren’t any participants in the workshop who didn’t already have considerable experience stemming from their working life.  Second, aggravations, challenges, and difficulties in the workplace are practically speaking, if not infinite, certainly vast in both quantity and type!  So there was a lot of “raw material” that we could apply Stoic principles and practices to, and that leads into the third reason.  As it turns out, although the ancient Stoics have no contact with or awareness of  the modern workplace – how could they? – they actually say quite a lot that turns out to be quite useful in dealing with difficult people.

Some Challenges in Applying Stoicism in the Workplace

Before launching into the workshop proper, I thought it could be useful to pause and consider a few common challenges that can arise when we are attempting to apply our Stoic practices and principles to the workplace environment.  The goal was not to attempt resolving these – there was definitely not enough time for that! – but just to highlight them so that they were out in the open.  Each of these probably merits a good bit of further discussion later on and elsewhere.
The first of these has to do with “indifferents” – adiaphora, in Greek – those things that, strictly speaking don’t have moral value in themselves, whether positive or negative.  At first glance, it can seem as if nearly everything that goes on, motivates people, or has some place, in the modern workplace is really some type of indifferent from the Stoic perspective.  Money, perks, positions, reputation, products and services, even the proverbial “bottom line”.  We can ask ourselves how Stoic we being if we focus on those sorts of matters.  An initial answer might be “not at all,” and we might then feel as if we ought to withdraw our attention or care from those.
A closely connected second matter – really another way of looking at those same things – is that those indifferents are also “externals,” and strictly speaking seem to be things that lie outside of our control, our power, or our business, if you like (all three of those are decent ways to translate Epictetus’ “ouk ep humon” in the dichotomy of control passages).  So should practitioners of Stoicism allow themselves to become concerned about those things outside of the scope of our agency?
Third, turning to one matter that clearly is up to us, and has intrinsic moral value – whether or not we develop and display the virtues – how do we translate these into the workplace?  Can we really make it all about virtue?  Or expanding and unpacking it a bit, should we make it all about our duties, or fulfilling our roles?
Fourth, if we make virtues, duties, and roles central in how we approach the workplace – and particularly our fellow human beings in the workplace – aren’t we setting ourselves up for exploitation  by others in that workplace?  Do we put ourselves at a disadvantage by being too understanding or accommodating, by fulfilling our duties, even if others don’t reciprocate?
To raise a fifth concern, justice is one of the four virtues for the Stoics.  And there can be a lot of things in the workplace that either seem or actually are unjust.  To what extent are we called upon, if we want to practice Stoicism, to say something or do something about the injustices we run across?
A sixth difficulty almost goes without saying – but it can be easy to forget, especially for people starting out in practicing Stoicism.  The other people in in any given workplace are very likely not going to be Stoics. It is possible that you might find some allies or supporters, but often you’ll find people motivated in all sorts of other ways, many of which are going to be quite at odds with Stoicism. And quite a few of them will turn out to be difficult people for the would-be-Stoic!

A Partial Typology of Difficult People

When it comes to general types of people – classifying them along the lines of their characteristic behavior, motivations, choices, priorities, emotional responses, or practical reasoning – there are a vast variety.  Really, that’s not a surprise, when you consider how adaptable human beings are, and how many different things we take an interest in, or orient ourselves by.  You can run into all sorts in the workplace.
Some of them definitely fall into the broad category of “difficult people”.  That is a relational and also a relative term.  People are more or less difficult, and they are difficult for or to some people, and not to others.  I provided what is admittedly only a partial listing sorting out a number of different kinds of troublesome people – I’m sure others can contribute many other additional overlooked categories to this enumeration!  Here are those that I brought up as classes of people who make the workplace difficult, some of which we discussed in the workshop:

  • Chronically negative people
  • Drama kings and queens
  • Bullies, sadists, and abusers
  • Unduly demanding people
  • People with annoying traits or habits
  • Disorganized, unprepared, and flakey
  • Greedy, self-centered, and exploitative
  • Contentious and argumentative people
  • Status-obsessed and overly competitive
  • Entitled, unmotivated, and lazy people
  • The incompetent and uncoachable
  • Over-social, hyper-sharing, and gossipy
  • Passive-aggressive and victims
  • Rageaholics, over-sensitive, and other angry
  • Back-stabbers and promise-breakers
  • Bad influences and enablers
  • Controllers, corallers, and “team-builders”

I should point out a few things about these categories.  First, although I have given them what I hope are fairly clear and suggestive names, each could use a bit of explanation (which in interests of space, I won’t attempt here).  Second, some of them might overlap or bland into each other, in two ways.  They might intersect to some degree conceptually.  and of course, in real live persons, any given human being might fit into multiple categories.  Third, you can find difficult people who can be rightly placed in these rubrics at any level of a company, organization, or institution.  They might be a boss, an executive, a manager, an employee, a customer, a vendor, a supplier, even a temp.
From a Stoic perspective the question isn’t whether such people exist.  It isn’t even whether labeling them in these ways is somehow wrong, or unfair, or offensive – read around in Marcus, Epictetus, and Seneca, and see how many people they are willing to label along similar lines!  The real question is how we can deal with those difficult people in productive and positive ways.  What resources does Stoicism afford us?

Useful Stoic Practices In Dealing With The Difficult

A good portion of the workshop was devoted to precisely that question.  What practices can we draw upon from Stoicism that will enable us to better handle situations involving difficult people in the workplace?  I broke those practices down into two sets – those to use within situations, and those better used before or after situations.  We had a good bit of discussion about some of these, as you’ll find when watching the recording of the workshop session.
Here are some of the useful practices that can be used within situations, with some brief explanations:

  • Dealing with appearances as such – not immediately giving assent to impressions or appearances that present themselves to you, but instead seeing them in proper perspective.
  • Deconstructing things into their parts – taking matters you find troubling, provocative of negative emotions, or appealing to your desires, and reminding yourself of what they really are.
  • Distinguishing what is or isn’t in your control – employing and reminding yourself of the dichotomy of control, and as best you can dissociating your desires and aversions from those that are not in your control.
  • Picking things up by the right handle – choosing how you frame the matters that you encounter in ways that you will be able to effectively deal with those matters, for instance by focusing upon your own duties and roles.
  • Understanding others without excusing – realizing that people think, feel, talk, and act as they do because that seems good or reasonable to them, even if it isn’t, and even if it is dead wrong.
  • Reminding self of values and costs of things – these costs include, for example, what it takes for you to be undisturbed by what would otherwise set you off.
  • Focusing on bigger-picture perspective – reminding yourself that if you step away from your personalized perspective things and people will not seem as important or as disturbing.
  • Sticking up for what is right in right ways – using the virtues as a guide, restricting excesses and properly orienting the stands that one feels compelled to take.

Here are some of the others that can be used before and after situations:

  • Examining your own desires and aversions – this sort of honest self-scrutiny allows you to really grasp what motivates you.  Those motivations might be healthy and rightly directed, or they might need some work on your part, if you are finding yourself overly invested in what you could look at as indifferents.
  • Reminding yourself you deal with people – before and after you wind up in difficult situations, you can remind yourself of precisely that truth, that you are dealing with actual human beings who have their own histories, habits, relationships.  These are rarely people as you would want them to be.
  • Working to gradually change your habits – generally they ways in which we think and feel are in part products of habits we have developed.  In dealing with difficult people, we may have already developed bad habits that continue to make those situations difficult for us
  • Engaging in negative visualization – both as a regular practice, and before going into a situation that you know will likely involve difficulty, you can imagine what might occur in that situation, consider whether it is likely to be as bad as you fear, and think about what resources you have to deal with it.
  • Reminding yourself of larger part-wholes – as human beings, from the Stoic perspective, we are all parts of larger wholes, just as the organs of our body are parts of a greater whole.  Taking that perspective can help us see others and ourselves as involved in something bigger.
  • Spending some time with the virtuous – especially when dealing with difficult people, we need to involve ourselves with people who provide us with positive interactions.  This can be done in person, through various media, or even virtually when we read and place ourselves in conversation with Stoic authors.
  • Tracking and reflecting on how you do – engaging in some daily reflection and self-scrutiny, whether just mentally or in journaling, allows you not just to track your progress.  It also can help you to gradually gain insights about additional things you might need to focus on.
  • Taking joy in your progress and successes – this I think is particularly important, not least since you are likely not going to get much of this from others.  Stoicism views positive emotions like joy as good for us, and feeling genuine happiness when we succeed or make progress helps keep us engaged in doing that more and more.

Gregory Sadler is the Editor of the Stoicism Today blog.  He is also the president and founder of ReasonIO, a company established to put philosophy into practice, providing tutorial, coaching, and philosophical counseling services, and producing educational resources.  He has created over 100 videos on Stoic philosophy, regularly speaks and provides workshops on Stoicism, and is currently working on several book projects.

12 thoughts on Dealing With Difficult People at Work: Stoic Strategies by Greg Sadler

  1. Lucy says:

    Wonderful advice Greg! Just emailed it off to my son in DC. Thanks so much!

  2. David says:

    Greg, thanks for this very helpful guidance on difficult people in the workplace.
    In the context of the #MeToo movement, we might want to add the sexually aggressive and the sexually alluring to the typology.
    I’ll leave it to others to suggest steps for dealing with the former, though the first and best line of action could be to report the problem to those in authority wherever and whenever possible.
    As for someone who might be sexually attracted to a co-worker or staff member and fearful of committing an infraction, the following entry from the list of useful Stoic practices seems advisable: “Deconstructing things into their parts – taking matters you find troubling, provocative of negative emotions, or appealing to your desires, and reminding yourself of what they really are.”
    I’d add only that it might be necessary to consider the attractive person in a way that emphasizes physical and personal attributes that are not so wonderful or remarkable, sort of in the same way that Marcus Aurelius encourages himself to view sumptuous meals as dead animals. I can attest first hand that this method really works. No matter how good looking or charismatic the other person might seem, she or he is full of faults. And taking them on board can change your perspective to something more sane.

  3. Robert says:

    Very useful article!

  4. Nicely done, Greg! I believe I have encountered most of the difficult “types” in your list–if not in my profession of psychiatry, then in my academic departments!
    Best regards,

  5. JohnF says:

    Very good subject. During my career in law enforcement I came across many demanding, emotional supervisors who were nothing but bullies. I would use the Stoic philosophy in that I reminded my self there are certain things in my control, certain are not. Also the perception these people had on you was something I couldn’t change. I just did my job well and recorded everything that happened. After a while I got a reputation as a loner but I slept better at night.

  6. Bob Mark says:

    Very useful and applicable not just to the workplace. Thanks

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