Ep #46: How to Deal with Difficult People

The Joyful Practice for Women Lawyers with Paula Price | How to Deal with Difficult People

Difficult people; we’ve all got them in our lives. They’re our colleagues, acquaintances, or even family and friends outside of law, and it’s an experience that isn’t unique to just legal professionals. But while running into challenging situations where we have to deal with difficult people is a normal part of our professional lives, it doesn’t have to be as painful or frustrating as it is right now. 


In a legal environment where there are high stakes, high profile deals, and clients’ livelihoods on the line, it’s no surprise your relationships become heightened and difficult. Whether you feel like you don’t have reliable support, your boss is a bully, or you’re intimidated by opposing counsel, my objective this week is to help you strategize and come up with new, more sustainable ways to deal with difficult people.


Listen in this week as I delve into what dealing with difficult people can look like, and how to address challenging relationships in a more empowering way to see opportunities for growth. The truth is you have the power to transform difficult relationships into ones you enjoy, and I’m offering my tips for starting to make this shift. 


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What You’ll Learn from this Episode:
  • The various shapes and forms of dealing with difficult people that we experience.
  • How you might be attempting to deal with difficult people. 
  • What you miss out on when you employ short-term fixes for dealing with difficult people. 
  • How we decide someone is a difficult person. 
  • What it looks like to take your power back in a difficult relationship. 
  • How to approach dealing with difficult people from a longer-term perspective. 
  • The strategies and skills I’ve learned from dealing with difficult people in my life. 


Listen to the Full Episode:

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Full Episode Transcript:

You’re listening to The Joyful Practice for Women Lawyers Podcast episode number 46.

Welcome to The Joyful Practice for Women Lawyers Podcast. I’m your host Paula Price, lawyer turned certified executive coach. This podcast was created to empower women lawyers just like you to create a life and practice you love. Join me every week for a break from the hustle so we can focus on you, what you truly want, and how you can create it.

If you’re over the overwhelm, done with putting out fires, and ready to create a life and practice that brings you more joy, you’re in the right place. Ready for today’s episode? Let’s dive in.

Hello my friends. Welcome back to the podcast. I hope you are having an amazing week. Wherever you are, however this podcast finds you, whether you’re going for a walk or you’re doing the dishes or you’re just relaxing and enjoying a podcast. It’s such an honor and a pleasure to be connecting with you today. I hope that you are just having a great time. I am excited to bring today’s topic to you. Difficult people. We all have them in our lives. It’s a topic that comes up quite a bit. I’ve got some tips for you.

Before I do that, I just wanted to give a special shout out to one of our podcast listeners. Her name is Rachel. I’ve had the pleasure of exchanging emails with Rachel, and she is lovely. She left a review the other day, and I just saw it because I was looking up some of the previous podcast episodes that I would like to refer to today and I saw her note. So I’m just going to read what you wrote.

She said, “Everyone should be listening to this podcast.” Here’s her comment. This is a review on iTunes I believe. “Paula has a unique way of simplifying things, and she constantly provides practical solutions to dealing with struggles everyone goes through but no one really talks about. This podcast is gold. Thanks, Paula, for the consistency and for constantly trying to break strongholds on people’s minds. I found the podcast really helpful. I’m so grateful for the gift of you and this podcast, Paula. Well done. I’m so proud of you and how far this podcast has come. “

I wanted to say thank you to Rachel, a true genuine from the heart shout out. I feel like being able to connect with you every week is an honor. The way I see it, we are all on the same page. We are all growing together. It means so much to me that we are able to connect in this way. If there’s anyone else out there who’s listening who is minded to leave a review, please go ahead and do that. I would love to hear from you.

I’d love to hear how this podcast is having an impact on you in your practice, in your life, and to hear what kind of changes you’re making because of what you’re learning, because of what you’re learning here on the podcast. But perhaps more importantly because of what you’re learning about yourself.

So today, we’re going to be talking about how to deal with difficult people. This comes up a lot in a legal practice. It comes up in your everyday life, of course, but it has a unique twist when you’re working at a law firm, for example, or at an organization as a lawyer. It may look a certain way. So today what we’re going to do is delve into what the problem can look like. We’re going to then go into how to address the problem using a framework that I offered in an earlier podcast, which is the framework of looking at your practice through the lens of the four pillars of a joyful practice.

So if you have not already listened, I go into detail in Episode 35 about the four pillars of joyful practice. They are mindset, alignment, process, and growth. Those are the four pillars. I’ll get into that in more detail later in this episode. But the idea here is to really take a step back and look at the challenges that are posed by dealing with difficult people through those different lenses. I think doing that will have a real impact on how you see the challenges you’re facing, how you approach them, the strategies that you engage in, and ultimately how you grow from those challenges.

So let’s jump into that today. I’m excited. Are you excited? Difficult people. Let’s get started. So first of all, what does the problem look like? If you are in a situation where you’re dealing with difficult people, and I’m really talking here about your workplace, but it can come up obviously in other places in your personal life. It can be challenges that you may be having with your family members or friends or just people that are in your life.

So I would invite you to use this framework as well for difficult relationships that are outside of the work context. But here, we’re really gonna be focused on what it looks like at work.

So what kind of difficult personalities might show up? Difficult bosses. You know those bosses who maybe have really high demands that they place on you, maybe they don’t really understand. You have difficulty communicating with them. Things seem to get lost in translation.

There are multiple ways that you may have difficult boss relationships. It may even be that they’re not necessarily difficult in an unpleasant way, but they’re difficult in a way that there just seems to be a lack of cohesion in the dialogue that you have with them. So in your mind, it’s a difficult relationship. They are a difficult person for you to deal with.

Another common example is opposing counsel. This comes up a lot, particularly among litigators, but I believe it’s also possible for solicitors. Again, I’ve never really practiced as a solicitor. So I don’t really know what that dynamic looks like. Although I have heard that when negotiating contracts that you can have real points of contention, and that the challenges arise as they would in a more litigious situation.

So what I’ve experienced and what I have witnessed and conversations I’ve had with clients when it comes to opposing counsel, those relationships can be really challenging. You might feel like that person on the other side of the file is really nitpicking your work. They are trying to one up you. They are trying to gain the better position, and they are. That is their job to do that. So those are relationships that may be really difficult for you to manage.

Another case where this might come up is workplace bullies. We’re not really going into today about what harassment looks like in the workplace, what bullies look like, what it is like to be in a toxic work environment. Although, I do have a guest coming up in a few weeks. I think we will be able to get into some of those topics. So stay tuned.

But here what I’m really talking about is when you feel like others that you’re working with aren’t on your side, that they are potentially trying to undermine you, and you now need to deal with them in some way. They are difficult for you to deal with. Maybe they’re making it difficult for you to do your job. They are maybe talking about you to others in a way that is not a true reflection of what’s really going on. It can take all sorts of different shapes.

It may be that you have clients who you find difficult to work with. It maybe that they’re particularly demanding of you. It may be that they speak to you in a way that you don’t find to be respectful. It may be that they don’t respect the boundaries that you’re trying to establish. Maybe that they are asking for things that are unreasonable and then getting upset when you’re not able to provide those things. So that can be another area where you have difficulty.

You may have those emails that come in from certain clients. I know I’ve had that experience where you see the name in your inbox, and that feeling of dread just washes over you because you realize you’re going to have to have an interaction with somebody who typically is difficult for you to deal with.

Another area where you may find you have difficult relationships or people are difficult in the workplace may be support. So it may be these are members of your admin team who are there to support you and your work. It may be that these are lawyers who are more junior than you who are not necessarily performing in the way that you would like them to. So you’re delegating work, and the work isn’t coming back the way that you would like it to come back.

So you may find it difficult to work with these individuals. It’s not so much that they are bristly or hard. It’s more that it’s just difficult to work with them because you’re not really having your needs met.

Now, I described these problems in the context of legal professionals, but it isn’t something that is unique to legal professionals. I think we all have friends, acquaintances, colleagues outside of law, and we know that people are people. We’re going to run into challenging situations. It is a normal part of professional life.

However, in a legal environment, particularly in a law firm or other situation where you have high stakes, files ongoing. Maybe it’s high stakes litigation. Maybe these are high profile deals. These are situations where someone’s livelihood is at stake. Their family relationships are at stake. Their financial health is at stake. When you’re dealing with these situations where there’s a lot of pressure, then the relationships that you have may become heightened.

So you might imagine that client that we’re talking about where their expectations may be really hard to manage, and maybe they’re involved in a really contentious estate dispute. It may be really difficult for you to deal with them.

So some of the strategies that we’re talking about today I’m hoping will help you in your approach to those difficult situations because the reality is people are people. As long as we’re active agents in the world and we’re not living in a total bubble, which for some of us has actually been somewhat doable over the past two and a half years. But unless you’re living in a total bubble, you are going to be engaging with others. So the objective here is really to help you strategize and come up with new ways to deal with those difficult relationships.

Now, what you may be doing presently to deal with difficult people, I mean often we’ll just try to avoid them. So maybe you’re avoiding conversations with your boss or difficult clients. It may be that you’re overcompensating to try to please people. I think we’ve all been in that situation where we have that person who’s just really hard to please. So we’re literally turning cartwheels to make them happy. Sometimes it works, but in the long run, it rarely does.

It may be that we’re doing other people’s work for them. So, again, this kind of looks back at that relationship you might have with people who are there to support you. Whether it’s your staff that’s there to support you, whether it’s other lawyers who are there to support you. You may find that rather than have this really difficult direction with them, you’d rather just do it yourself. It may be that you find you are tolerating behavior from other people that really is not acceptable to you.

You may also reach that point where you start to blame yourself. I mean, it may be that you’re working with somebody where you always leave conversations with that person just feeling down about yourself. Maybe you start to think that it’s your fault. That this is something that you’ve created.

It may also be that you spend time complaining about it. So you may not complain to that person, the person who you find to be difficult, but maybe you’re complaining to your friends, to your family, to your partner, to whoever it is that you happen to be conversing with.

The trouble there with all of these things that you may be doing currently to deal with the problem is that they offer temporary relief. So there’s relief and being able to say to somebody, this is what just happened. Maybe they take your side and you feel good for a little bit, but it doesn’t solve the problem, right? Maybe you avoid difficult people, but eventually you’re going to have to come face to face. Maybe you’re overcompensating to try to please people, but ultimately you’re burning yourself out, and it’s just not sustainable.

What can happen if you try these sort of short term solutions is you end up feeling exhausted. You may feel frustrated, and you’re wasting energy on things that are not really moving you forward instead of spending your energy on productive things. Relationships that you would like to build. You know, you may be so busy managing the difficult relationships that you’re ignoring the potential relationships with individuals who can really lift you up.

If you’re avoiding dealing with the person, then you may also be missing out on the opportunity to build the skills that would help you cope with the difficult relationships, cope with the difficult people, or build the courage to change the environment. Maybe it’s stepping away from that relationship, whatever that might look like. If it’s an employer, for example, it may be relocating to a different job. It may be switching departments. If it’s a client, it may be finding a way to no longer work with that particular individual. If it’s staff, it may be finding a way to rearrange your working arrangements so that you’ve got people that are more reliable.

I mean, there’s all sorts of opportunities for growth. We’re going to talk about that. But what I’m trying to get at here is depending on what you’re trying right now, if it’s a short term fix, it may not be resolving the problem for the long run. That’s why it’s so important for us to think about how you can approach this from a longer term perspective.

So what we’re looking at today is how to deal with difficult people from the perspective of the four pillars of a joyful practice. As I mentioned, those four pillars are mindset, alignment, process, and growth. I’m going to go through each of those starting with mindset.

So let’s take a step back and think about something that we’ve talked about before on this podcast, which is the relationship between your thoughts, your feelings, and the actions that you take. This is a relationship that is well established in the domains of cognitive behavioral therapy. I’m not a therapist, but I think this is a concept that is helpful. So we’re going to talk about it and how it relates to the dealings that you have with difficult people.

So let’s start with how you feel when you are around people who you consider to be difficult. Often we know that somebody is a difficult person or we decide that somebody is a difficult person based on a feeling, right. I could have started with the thoughts here, but I think actually the feeling is really what drives us.

So if you think about a difficult boss, for example, and maybe you have a boss currently or in your past where you had a label for them as being a difficult boss. What is it that you felt when you were around that person?

Some of the feelings that I have come up with in response to this are scared. Maybe you feel fearful around that person. Maybe you feel undervalued. Maybe every time you’re around them, you somehow feel incompetent. Or maybe they make you feel like you’re overlooked. Like you don’t really matter. Maybe you feel undervalued? I think I mentioned that when twice.

Opposing counsel, right? What is it that makes opposing counsel difficult? I know I’ve been in situations where I’ve had opposing counsel who I don’t find to be all that difficult. We have managed to resolve files or even dispute files without me thinking of that person as difficult. Whereas I’ve had lawyers who I’ve found to be very difficult.

There’s one lawyer who comes to mind when I was a very junior lawyer. I think it was one of my very first files that I ever had where I was a lawyer. I was no longer a student. I was a lawyer. This particular lawyer, we’ll call him John Smith, was really hard on me. He was much more senior than me. He was definitely trying to intimidate me.

I just remember every interaction that I had with him he used as an opportunity to get really aggressive. He used really harsh language. He got off on a soapbox and told me how terrible our case was. It turned into a bit of a funny story in the end. This isn’t going to sound good, but he was acting—It was a personal injury file, and sadly, his client passed away. In relation to that particular claim, it meant that 99% of her claim also disappeared with her passing. It didn’t stop him from relentlessly pursuing the case.

I had this colleague at the time who was helping me out. He was a bit more senior to me. He used to come into my office, and he’d be like, “Ooh I am John Smith, the lawyer for dead people. I channel my energies through the ether.” Or whatever it was. As I’m saying this, I really hope that this does not rub anybody the wrong way. I really don’t mean it to. It was just kind of comic relief in an otherwise very stressful situation.

What ultimately happened was this particular lawyer, John Smith, did abandon the claim. I think he finally decided after we kept defending that it was no longer worth it for him to keep trying to press us to capitulate and do something.

So I tell the story because, at the time, every time I would see John Smith’s name in my email, I was intimidated. I felt like a little bit scared that this guy knows more than me. He’s been around way longer than I have been. I was a brand new call.

I guess I tell that story because there may be lawyers that you’re working with where you feel that right. They are way more senior than you are. They are pulling out all the stops, and you assume on some level that they must know what they’re doing because they’ve been around for so long. That can lead to a characterization on your part that they are difficult.

So what are the feelings you might have? Well, maybe it’s you feel a fear around them. Maybe you feel dread every time you see their name in your inbox. Maybe you feel self-doubt. Maybe you feel like maybe you’re missing something. That never feels good.

So workplace bullies, how do you feel around them? I mean, have you ever been in a situation where somebody who’s supposed to be on your team—I mean, it’s one thing for opposing counsel to be coming at you. I mean, in some ways, that is their job, right? They are there to defend their clients or protect their clients’ interests. So you expect that on some level from them. Versus colleagues who ostensibly are on your side. What happens when you start receiving that kind of behavior from them?

That might make you feel frustrated. It might make you feel angry. I mean, it might make you feel betrayed. But ultimately here what I’m driving at is what is the feeling that you get around that person? We’re going to look at that more closely.

A couple other examples, competitive colleagues. Maybe you have colleagues who aren’t necessarily bullies, but they’re really competitive. You know they’re out there comparing themselves to you, and maybe you feel unsafe around them. Maybe you feel threatened. Maybe you feel insecure because you feel you can’t trust them the way that you’d like to.

How do demanding clients make you feel? Maybe they make you feel guilty that you’re not chained to your desk 24/7 to make sure that you’re doing exactly what they are asking of you the moment that they ask you to do it. Maybe you feel fearful that you’re not meeting their expectations. Maybe you lack confidence. Maybe you want to say something and you don’t say anything. So you start to feel like maybe there’s something wrong with you. That you’re not able to assert yourself the way that you want to.

Maybe feel vulnerable. Maybe you feel like you need to please the person in order to be successful in your job. If you’re not pleasing them, then they may go somewhere else. So that might be a feeling that you have around them.

Finally, the last example that I had given was this idea of support staff, or lawyers who are there to support you who are not holding up their end of the bargain as far as you’re concerned. How does that make you feel? It might make you feel frustrated or angry or dismissive even or annoyed.

So once you’ve identified the feeling that you have in relation to the difficult person, let’s look at what thoughts are driving those feelings. Again, this goes back to that model of looking at how your thoughts influence your feelings which influence your actions. When it comes to this exercise what’s so helpful about it is that your thoughts are often unregulated, right?

We, as humans, have a lot of thoughts that simply shows up in our minds. You know there are thousands of thoughts that will show up every day. Our job is to become conscious of what those thoughts are and mindful and intentional about the ones that we choose to think and believe and the ones that we may challenge, much like a court of law, right. We don’t go into court and make the assumption that whatever it is that we say to a judge is true. You need to show up with the evidence and the facts, and the evidence that supports the facts that you are asserting.

The same is true here. We may accept that what our minds offer us as thoughts are true, but when you really get down to it, they may not be true at all. So anyhow, let’s be more disciplined about where we’re thinking. Let’s look at how the feelings that we talked about just moments ago are driven by your thoughts.

So if you have a difficult boss, for example, who makes you feel incompetent, maybe you would think to get there. Maybe you think that that person thinks that you’re incompetent. You might think that your boss, because of the way that they speak to you, because of the way that they look at you, because of the markups they make on a draft that you wrote. You may think that they think that you’re incompetent.

In a previous episode, I talked about thought distortions. If you look up thought distortions, you’ll come up with a list. I think there’s about a dozen or so the classic distortions. One of them is mind reading, right? You might think you know what somebody else is thinking, and you don’t. So here’s an example of that, where you think you know what your boss is thinking, when actually that’s not what they’re thinking at all.

Other examples. If you’re working on a file and opposing counsel are particularly difficult, maybe the feeling that you have is self-doubt. Maybe the thought that fuels that is they know more than me, right? So if I go back to that example of John Smith, I felt self-doubt thinking he knows more than me. He’s been around way longer than I have. So that caused me to feel doubt in myself. Maybe you have files like that, too.

So right now, we’re really just getting awareness of what is it that you are thinking to make you feel that way. Again, going back to that example, maybe John Smith did know more than me, but I also knew something. I knew that his claim had pretty much evaporated. So regardless of the actions that he was taking, he was taking them in relation to a file where he effectively had almost no claim left. I think I mentioned this already, but ultimately, he abandoned that claim. So again, you may think they know more than you, but in fact, they don’t.

So another example, a demanding client. You may feel vulnerable dealing with that person because you feel like I have to do everything. Or you think I have to do everything that they’re asking me to do, or else they’re gonna find somebody else. So that thought leaves that feeling of vulnerability.

Going to the example of unreliable support. Maybe you feel annoyed. The thought that you have is they’re not listening to me. So I would really invite you to get granular about the way that you’re thinking about the difficult people in your workplace, or your clients or whoever these people are. I would also encourage you to listen to the podcast episode that I recorded about blind spots. It’s episode number 28.

The reason that I would encourage you to listen to it is because sometimes we see things, and yet we don’t see them. So we might see something in somebody else, and it turns out that that’s something that we actually see in ourselves. It’s a challenge that we have ourselves. So it can be a really interesting learning exercise as you’re thinking about others and the challenges you’re having with them. Sometimes it’s a reflection of something that we’re actually having a challenge with in regard to ourself.

So it may be that you think that your boss thinks that you’re incompetent, but really you think that you’re incompetent. The beauty in understanding that that’s what you’re thinking is that then you can deal with that thought, right? Because we decided that that thought may or may not be true. Well, let’s look at what the evidence is because chances are if that’s a thought that’s floating in your mind and it’s causing you stress and anxiety, we can unpack that thought and prove that you’re actually not incompetent. So that’s just an example. I’d recommend listening to that podcast episode.

Now, another element I wanted to highlight here just in relation to how you’re thinking about people generally is that there’s this really wonderful paradigm. It’s called the Drama Triangle, and I’m not going to explain it in full. It’s a concept that was developed by Dr. Stephen Karpman.

What he does is he takes the Drama Triangle. There are three actors in that triangle. There’s the victim, the rescuer, and the perpetrator. Here I’m really just going to talk about the victim, but we all know what that looks like, right. Where you see yourself and you describe yourself at the effect of somebody else’s conduct. It’s a very unpowerful place to be.

Versus the triangle where you are removing yourself away from the drama into one of empowerment. In that paradigm, you have the victim becomes the creator, the rescuer becomes the coach, and the perpetrator becomes the challenger. So here what I would like you to bear in mind is that we’re going to move you away from a victim to a creator. Instead of the person who is vulnerable to the world around them, you become the creator. You take responsibility, and you take your power back. It’s such a stronger place for you to be.

So we’ve talked about your feelings in relation to difficult people. We’ve talked about the thoughts that give rise to those feelings. Now we’re going to talk about the actions. What actions are you taking based on the thoughts and feelings you have about a particular person?

So if you have a boss, for example, who you’re scared of, or opposing counsel who you find intimidating, you may avoid that person. You have to ask yourself if that action is giving you the result that you want to create.

Similarly, if you have somebody who you perceive to think that you are incompetent, you may find yourself making more mistakes around that person. It may be that if you’re frustrated, you may find that there’s somebody that you are delegating work to, and it’s not coming back the way that you want. Instead of having a conversation with that person, you’re venting to somebody else.

So here, I would just invite you to think about how your thoughts and feelings are driving your actions. And whether or not there’s leverage there for you to become more conscious of how you’re thinking about the situation, and more deliberate about the actions that you want to take.

So when you get on top of your mindset, which is that first pillar, you’re taking a look at how you’re thinking about the person. This gives you an opportunity to understand yourself better. It gives you an opportunity to challenge and potentially reframe some of the thoughts and beliefs that you have about that person, about that situation. It gives you an opportunity to move intentionally from the victim role into the creator role.

When you do these things, you can then decide on your strategy from a place of clear headedness. You’re no longer sort of muddled in your thinking by not thinking on purpose and by not really identifying the emotions that are maybe getting in the way or the thoughts that are creating those emotions in the first place.

So once you get through that first pillar of mindset, you’re going to be looking at alignment. This section is a little bit briefer than the last one. I think the mindset is really key. That is when you start looking at how your broader goals are driving the container that they are creating for the relationship or the difficult person that you are dealing with. So we’re gonna look at alignment in a few different ways.

Number one is—Sorry before I go there, I also just wanted to highlight that alignment is one of the key pieces in creating a practice that you love. It’s important in your professional life, in your personal life, when you can align your actions with your goals and your values, that is when you get to that place of life or work feeling easy. I mean it’s still effort, but it feels good. You get into that state of flow. You don’t feel like you’re constantly pulled in different directions.

So here when you look at alignment and you look at the people in your life in relation to alignment, number one is to take a step back and look at what your broader goals are. Where does that person fit within that context? If it’s a boss that is maybe difficult for you to work with, what are your real goals for your work? Where does that relationship fit in here? How are you going to align your thinking, align yourself, so that the objective, like your greater objective gets larger in your view than the difficulty of that particular relationship?

If you’re, for example, working on a file, and opposing counsel is really difficult, what is it about that file that is important to you? How can you adjust your thinking so that the objective, that greater goal, becomes larger from your perspective, and that difficult relationship becomes smaller?

Another way of looking at alignment is to think about how you and the difficult person are in alignment. What is it that the two of you have in common? How are you going to leverage that, not only for the objective long term, but in your relationship with that person?

Finally, how are you not aligned with that person? So it may be that there are differences you have with that person. When you identify how you are not aligned, that might give you data that you can use to make other decisions.

So that’s the alignment piece is you really want to look at how that person plays into the bigger picture. I did a podcast episode, episode number nine, it’s all about integrity. We talk about alignment there. If that’s something that you want to give more thought to in terms of your own practice, in terms of how aligned you are, I recommend going back to that podcast episode and giving it a listen.

So the third pillar is process. Process is probably the piece that attracted you to this podcast episode. So hopefully, it’s a benefit to have more than just process. Hopefully, it’s exciting to you that we’re at this stage, right. This is more the how to.

So once you’ve wrapped your mind around the problem and how you want to deal with it, the person. Once you’ve seen how alignment fits in here, how this relationship is aligned with your greater goal, how managing this relationship serves your greater objective, serves your client’s greater objectives, then we look at process.

Here’s where I just wanted to offer a few tips and pointers. So, again, going back to when I was a junior lawyer. I had a very—I guess you would call him a difficult lawyer to work with. I really liked him. So I don’t like to call him difficult. But I remember going to his office one day talking about a file and having him send me away. “Go away. Come back when you’ve done all these things.” He gave me a bit of a laundry list of things that I should be thinking about.

Of course, I went away and did all of those things and then I went back. It wasn’t just that one interaction that mattered. What mattered was I developed a process. I developed strategies. I developed systems and ways, and I then knew that if I ever wanted to talk to him about anything that I had better do my homework before going to talk to him. So I learned how to prepare for conversations with a difficult person.

There have been many difficult people in my life who I’ve had the pleasure and benefit of learning from. I will tell you every time you engage with somebody who you consider to be difficult, it is a learning opportunity. We’ll talk about that a little bit more when we get to growth. But here are some of the takeaways that I’ve learned from dealing with difficult people, particularly in a professional context.

So number one is I like to have an agenda. If I’m going into a conversation with a client or somebody that I work with who may be, I use air quotes, difficult from my perspective, I like to know exactly how that conversation is going to go. I want to be prepared. So I will create an agenda for myself.

If it’s a more formal meeting, then maybe that agenda gets circulated, but it doesn’t have to be right. Really the roadmap is yours. The idea here is to get all your thoughts down on paper to organize them in a way that the conversation is going to go smoothly.

You want to know who your audience is. So in the case I just mentioned, right, where I’m dealing with particular lawyer. He’s given me a laundry list of questions. I know that before meeting with him that I should have answers to those questions. Depending on who you’re working with, depending on what it is that you’re asking of them or the reason for the meeting, then you may have a different list of questions.

The idea there is to know them, to know what’s important to them, and to tailor the agenda to their interests. It’s like going to court and speaking to a judge and knowing that a judge like things done a certain way. You want to do that for them. You want to do that for individuals who you may consider to be difficult to deal with.

I would encourage timing your meetings with people who you consider to be difficult in a very strategic way. If you work in the same office, it might be obvious. If their door is closed and you see them kind of rushing in there and not looking at their best, then that’s probably not the best time to knock on their door and ask them a question or talk to them about something that is not urgent. If it’s urgent, you may have to do it anyways.

If you don’t work with them, you may not have the benefit of knowing that. In our remote or hybrid setting, it may be that you need to schedule an appointment. So this may be something you’re doing already. But I recommend being strategic in terms of when you talk to them. I recommend you know picking a time of day that you think they’re going to be in a reasonably good mood.

Also, give them time. Don’t leave things to the last minute. That might be tempting because you’re dreading the conversation. Don’t do that. Give yourself the benefit of time and give them the benefit of time too. Because remember, you are on the same side, more likely than not. Then finally, I have set appointment here. So that’s kind of a follow up on that. It’s picking the timing and setting an appointment, if that’s what makes sense in your particular working arrangement.

Again, if you’re working in an office and maybe the practice is to drop by people’s offices, you may find that that’s not something that they’re very responsive to. So you might actually want to send them an email in advance, ask them when it would be a suitable time, give them a time estimate, if you can. You know, I think this is going to take 10 or 15 minutes. You want to set it up so that there’s minimal surprises for them. They can get used to the idea that you’re going to be having a conversation. It’s going to take X amount of time. They can then fit you in.

Another strategy is once you’ve had the conversation with somebody, and this could be somebody that you work with, it could be opposing counsel, it could be a client, it could be somebody who you’re delegating work to, is to send a confirmatory email. Now, whether or not you do this depends on what you’re confirming. Sometimes if it’s opposing counsel, you’re just wanting to create a somewhat self-serving record of a conversation or give them an opportunity to say, “No, that’s actually not what we discussed.”

If it’s somebody that you’re giving instructions to, you might just want them to have that additional layer of clarity. If it’s somebody that you’re receiving instructions from, maybe it’s a client, maybe it’s not a lawyer. You may just want to confirm in writing that that’s what happened. You may do that as a practice regardless with everybody. It’s a good practice to have. You always have your written record.

But if you’re not in that practice or there certain things you’re not doing that for that you think actually, maybe I will start doing that. Then that is another way to deal with people who are difficult, particularly if it’s somebody who may change their—Or over time, their perception of a conversation may seem different, or you’ve had situations in the past where they’ve changed their instructions, etc.

So we’ve talked about how you approach the meeting, what you do after the meeting. Another suggestion I have is knowing what you want ahead of time. So in British Columbia if you go to the Court of Appeal, you need to set up your factum in a way that you’ve got the issues laid out nice and clean. It’s basically a yes or no question. Can you reduce the ask of your conversation to that level of granularity so that you’re making it simple for that person to decide, right?

When you go in with a laundry list of things that are going on and it’s really opaque, they don’t really understand what you’re asking for. It can be difficult and frustrating for them to even understand what the problem is. So by digesting the matters beforehand, by giving some fairly granular questions, you actually make it easier for that person to tell you what they want or make a decision about how to proceed.

Same is true for clients whether it’s somebody—In my mind’s eye, I’m thinking of difficult conversations with colleagues, difficult conversations with lawyers, difficult conversations with your clients. So think about how to narrow it down. It may be that the question that you ask gets changed, right? Maybe you have a conversation. Maybe there’s a discussion about what the real issue is, and it’s not exactly the way that you had framed it. But having framed it initially at least gives you that starting point so that you can work from there.

Then finally, I have a couple of points is number one, how do you want to feel in that conversation. This is something that I’ve just really learned of more recently since becoming a coach, which is to focus on the energy that I want to bring to the conversation. I recorded a podcast episode about that. It’s episode number 15. It’s elegant approaches to difficult conversations.

So what is the energy you want to bring to that conversation? You get to be intentional about that. Is it confidence? Is it curiosity? Is it a cooperativeness? Whatever that looks like for you. I would invite you to think about that energy and then work your way backwards. We talked about the feelings and thoughts. What are the thoughts you need to have about yourself, about the conversation, about the other person to generate that energy?

So if it’s confidence, you might need to think I’ve prepared extremely well for this. I know what I’m talking about. I’m the right person for this, etc. Another thing you might be thinking is, we are on the same team. They are going to help me. They are going to be interested to learn. Whatever it is, I would just encourage you to be intentional about how you show up for that conversation. Again, there’s a whole podcast episode about that if you want to go into that further.

Then finally, how do you want the other person to feel? There’s a wonderful expression. I believe it’s Maya Angelou who said it, which is people will rarely remember what you say, but they will always remember how you make them feel. So much like we go into these conversations or we’ve started this discussion by thinking of the difficult people in your workplace and how they make you feel, well how do you make them feel?

So I’d invite you to think about how it is that you want them to feel about you. You want them to maybe trust you. So what do you need to do to establish trust with them, right? Show up on time, do what you say you’re going to do, deliver a quality of work product that they can depend on, all those things. So think about that. What is it that you want them to feel? How are you going to help create that?

So that’s number three, process. Those are some tips. Just to review, preparing ahead of time, confirming an email after the fact, get really granular about what the ask is going to be, what the result of the conversation is going to be. Preparing yourself in terms of how you want to show up energetically, and then finally, how do you want the other person to feel?

That moves us to the fourth pillar, which is growth. There’s another wonderful expression. I don’t know who to attribute this one to you, but there’s that idea that when the student is ready, the teacher will appear. So when you have these individuals in your life, how are they teachers for you?

There’s a couple of ways that you may learn and grow from the challenges that you have with difficult people. On the one hand, there’s growth that can happen within the relationship itself. So you decide to stay in the relationship, maybe you have to, maybe you choose to, and you’re going to learn skills and strategies to better manage relationship with that person. Or there’s the option of leaving that relationship. That, I would say, also brings up an opportunity for growth.

So one analogy that I’ll just offer up here is let’s say you have a sweet tooth. When there’s chocolate in the house, you find yourself being called into the cupboard with the chocolate. There are two ways you may manage this.

Number one is you might choose to not buy the chocolate in the first place and allow it into the house right. You’re altering your environment so that you don’t need to deal with that challenge. So that is similar to, for example, ending a relationship with somebody or changing the environment in which you work so that you’re not dealing with a particular person.

In that case, what you’re learning is growth that occurs by ending a relationship. So it may be leaving a situation that isn’t working for you, an area or organization where you won’t advance. I recorded a podcast episode last week which is all about moving past the rut of good enough.

It may be that you’re in an environment where you have a boss who doesn’t really see you at your full potential. It’s good enough, but you want to leave. There’s a risk that comes along with leaving what is familiar, even if you don’t like that situation. So if you choose to leave a relationship, if you choose to leave a workplace, there’s growth that will come with that because now you are facing the other side. You’re facing the unknown.

Now, the other option that we talked about is keeping the sweets in the house. Right? You buy the chocolate. You put it in the cupboard. Now your work is learning how to live in a house. Let’s say you don’t want to eat chocolate. How are you going to think about it? How are you going to manage yourself in a way that you’re not eating it if that’s your goal? I don’t know. Maybe it’s not your goal. So silly. Well, it’s not a silly example because I think it’s one that is relatable. I know I’ve been there.

But so how are you gonna deal with that? That leads to growth within the relationship. So instead of saying, “Okay, I’m just going to remove myself from that situation.” You’re keeping yourself in that situation, but you are doing the work that you need to do not to be affected by it. So if you find somebody to be very difficult, how can you do the work so that you no longer feel like that is a difficult person?

Maybe you’ve had that experience already where you’ve managed to turn a relationship that was really difficult and challenging into one that you really liked. So you might already have skills and strategies that you’ve used that have been effective for you. Because chances are you’ve learned how to grow in that relationship.

What might that look like? It might mean setting boundaries. It might mean getting really good at having difficult conversations, where you voice what your needs are in a way that is constructive, in a way that gets you closer to the results that you want. It may also be that that growth is how you show up in conversation. So you learn how to be decisive ahead of time in terms of how you want that conversation to go, and then show up for that. That takes a lot of courage.

It may also be that you have improved your relationship with yourself. So going back to what I said earlier about blind spots. How sometimes we think it’s the other person that is causing our discomfort, but really, it’s the thoughts that we have about ourselves that are really the true source of the problem. Maybe you find that in working out that relationship with somebody who you consider to be difficult, what you’re really doing is mending the relationship that you have with yourself.

Maybe if, you know, going back to that example of incompetence. You think somebody thinks you’re incompetent. Really, it’s you that thinks you’re incompetent. But then you’re able to overcome that and say well, no, that’s just a distorted thought. It’s not true. I just keep defaulting to that thinking, and I’m not going to do that to myself anymore. So it may be that its relationship with yourself.

So there’s different ways you can grow here. What I would invite you to think about is regardless of what path you choose to take with that person, and maybe you’re doing both right. Maybe you mend the relationship, and then you still decide to move on. But really, where is the growth here? If you’re the student, and they’re the teacher, what are you learning? Because chances are you’re going to be learning something that is of value to you that you can carry forward.

So in summary, the four different pillars of the joyful practice and how that relates to dealing with difficult people is number one mindset. So let’s step out of the victim mentality and become more conscious of how we’re thinking and feeling about those people and the actions that we’re taking as a result.

The second is alignment. So that’s really taking a step back, looking at what is really important to you, and deciding from that perspective where this relationship fits in to that equation. And how thinking about alignment can help you in deciding on your strategy and put more emphasis on the outcomes than on the difficulty of that relationship.

The third is process. So again, what are the strategies that you might engage in in having difficult conversations. So that’s going back to being prepared and being conscious of how you show up and how you want them to feel when they interact with you. Then finally, growth. How will you go through your dealings and learn to grow from them? Whether it’s within that relationship within the context of dealing with difficult people or if it’s in the context of deciding how you’re going to disconnect from them.

So the reason this will work is that you’re approaching the problem from multiple angles. What you might find is you’re thinking about this work in relation to one single person. But chances are, if you have certain challenges with one person, they’re also showing up other individuals.  So fixing one relationship actually has the effect of fixing multiple relationships.

It works because you get to take your power back. You’re no longer in this victim mode. You are now the creator. It helps you see the bigger picture and understand where this person, where this difficult relationship fits in. It gives you a chance to develop your own strategies for dealing with difficult people. As I mentioned before, I’ve developed strategies, and they continue to come in handy. I’m no longer in a law firm, but I’m human. I have relationships with individuals who I sometimes find to be difficult. So now I’ve got some strategies to deal with them.

You grow. And as you grow, it becomes easier for you to manage and deal with difficult people. You start to see the purpose and the lesson behind the difficulty as opposed to seeing the difficulty as something that is just problematic for you, that is inconvenient for you. You can see where the learning is.

Now, there are a few skills that you will need to do this work. Number one is you’re going to need to focus on creating change for yourself. So you’re going to need to be the initiator here to identify the people that you think are difficult, the areas where you can grow.

You’re going to need to be willing to give up the role of victim. It can be really satisfying to go and talk to somebody and tell them that the person you’re dealing with was, you know, so out of line and in the wrong, and they agree with you and you feel validated. I get it. That feels really good, but it doesn’t solve any problems. So what you’re going to start doing here is taking 100% responsibility. That will help you make actual change as opposed to that temporary band-aid solution of feeling good in the moment.

You’ll need to be persistent. As I’ve talked about before in the podcast, we are creating a joyful practice. It’s something that evolves over time. It’s not a one and done approach. So you’ll need to continue to work on difficult relationships. Lucky for you, lucky for all of us, we’re humans. We’re going to encounter different personalities as long as we are alive on this planet.

Finally, courage. I talk about this often in the podcast, but it’s that courage to go ahead and try things and have difficult conversations and see what happens. What will happen over time when you do this is you will develop more confidence in yourself and your ability to deal with difficult people. You’ll show yourself what you could handle, right. Your skills that maybe you didn’t even know you had.

You’ll start to feel more powerful and free even because you’re no longer stuck in a state of dread, where your feelings are dependent on the person that you’re dealing with. You’ll have a lot more agency and control over how those interactions go. Finally, what you may start to notice is that the people around you may seem less difficult.

So this, my friends, is today’s podcast episode. This week’s podcast episode. Thank you for staying with me. I realize this was quite a long episode. I hope these tips are helpful for you. I hope they help you navigate some of the difficult relationships that you have, helped you deal with people who are difficult.

If you’d like to chat about this more or you would like to work through this with me, I would absolutely welcome you contacting me. You can do that on LinkedIn, by email, through the website. You are welcome to find me. I continue to do one to one coaching, and I would love to hear from you.

So with that, I’m going to say goodbye. Thank you again for joining me, and I wish all of you a wonderful week and look forward to reconnecting again soon. Bye for now.

If you enjoyed today’s show and don’t want to miss an episode, subscribe, and follow the show wherever you listen to your podcasts. If you haven’t already, please leave a rating and review. Your feedback will help me create a podcast that’s tailored to your needs and goes straight to the heart of what matters to you. For instructions on how to subscribe, rate, and review the podcast, visit www.thejoyfulpractice.com/podcastlaunch. See you next time.

Thank you for listening to this episode of The Joyful Practice for Women Lawyers podcast. If you want more information, visit www.thejoyfulpractice.com. See you next week.

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