187. Difficult People at Work

About this Podcast

Ep. 187 – If you’ve ever been captivated by the challenges and dynamics of competitive reality shows like “Survivor,” “Squid Game,” or “Hell’s Kitchen,” you’ll find this week’s podcast episode particularly intriguing.

In the world of leadership, much like these reality TV competitions, the climb up the organizational hierarchy brings heightened challenges. Just as contestants face tougher trials and personalities clash under pressure, leaders encounter more complex problems and, inevitably, “difficult” people the further they get in the competition.

The real question isn’t IF you’ll encounter a challenging individual, but WHEN. Mastering the art of handling difficult people is not just a skill; it’s a career game-changer.

Whether it’s a challenging coworker, a demanding supervisor, or even a problematic direct report, we all encounter difficult people in our careers.

This episode provides valuable insights on how to navigate these situations, retain our power, maintain healthy relationships, and when it’s time to consider stepping away.

If you’ve ever felt stressed, drained, or frustrated by “difficult” people, this episode is a must-listen.

(And share it with any of your friends or co-workers who might be navigating a tricky work relationship right now.)

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Episode 187 Transcript:

Ramona Shaw [00:00:00]:

This is episode 187, and we’re gonna talk about difficult people at work, how to deal with it, how to navigate it, how to make the most of it, and when it’s time to step away or step aside. Here’s the question. How do you successfully transition into your 1st official leadership role, built the confidence and competence to lead your team successfully and establish yourself as a respected and trusted leader across the organization? That’s the question, and this show provides the answers. Welcome to The Manager Track podcast. I’m your host, Ramona Shaw, and I’m on a mission to create workplaces where work is not seen as a source of stress and dread, but as a source of contribution, connection, and fulfillment. And this transition starts with developing a new generation of leaders who know how to lead so everyone wins and grows. In the show, you learn how to think, communicate, and act asked to confident and competent leader you know you can be. Welcome to The Manager track podcast.

Ramona Shaw [00:01:00]:

This episode will release right after the Thanksgiving break in the US. So for those of you who did celebrate Thanksgiving in the US, I hope you had a good time with family, friends, loved ones, or just time to yourself to recover, rejuvenate, and spend some time outside of the office. I always enjoy this week quite a lot because no one’s really working. There’s a lot of people who are traveling, a lot of people who are out of office, and they are really shutting down for the Thanksgiving break. And it makes things quiet. It’s not the holidays yet, so, no. None of the holiday events and holiday things are on the horizon, at least not for me. And it always feels like a good time to take stock of, you know, how far have I come this year, what’s left to get done before the year ends.

Ramona Shaw [00:01:49]:

And so I’m very much into that mode of, oh my gosh. I have a long list of things I still wanna get done before we close out the year. I have some fun and exciting things come up in my personal life. I have some interesting and fun and things come up in my work life. And I wanna give it one last final sprint. Not to say that that’s the best way or the only way to go about it. But if you feel similarly, then we’re in the same boat, and you got a friend cheering you on and hoping you give it all you got so that once the holiday season starts, you are feeling really good to reflect back on the year and are proud of your achievements. As you often hear me talk about and I know we’re gonna get to the difficult people here in a moment.

Ramona Shaw [00:02:32]:

But if you’re a regular listener, then you probably have heard me talk about it being a lot more important to think about how you want to show up than to think about the result you want to achieve. So let’s take the podcast as an example. Instead of saying, I want to grow my audience or my subscriber list by an additional 10% before the year end, which I can’t control. I will instead focus on what will I do that then increases the chances that I actually achieve that end goal. So I really focus on all the things I are have 100% control over, all the behaviors, all the actions, the thought or the mindset that fuels those actions, that is 100% within me to choose every single day, every hour, every minute to show up and say, okay. On one hand, I’m gonna look at what are people actually wanna hear about. Difficult people is one of them. Talk about these things on the podcast in a somewhat unfiltered honest way, keeping it tactical and concise so that my listeners, most of them are pretty busy people, we’ll have a quick boost of information insights and hopefully ideas on how they can better show up at work.

Ramona Shaw [00:03:48]:

So those are the things that are a bit in my control. So what I do is put in my control. That’s what I really wanna focus on, and that then is what I will celebrate at the end of the year way more so than celebrating any outcome that I might have achieved that was outside of my control. So I will be proud if I did what I said I was going to do independent of whether or not that grew my audience. Just use the podcast here as example. And as I’m talking, I realized I could probably record another episode on goal setting, goal tracking and what actually provides us that sense of achievement and what we often do completely backwards, when it comes to goal setting and the expectations we have when we think about achieving those goals. That though is not gonna be an episode in on instead, I think I’m gonna just sprinkle this in into this episode as I just did, and the next few episodes that will release before year end. So stay tuned.

Ramona Shaw [00:04:47]:

Little cliffhanger there. Let’s talk about the difficult people at work, though. This is something that as I was recently reflecting on the most listened podcast episodes of 2023. My executive assistant, who is way more than executive assistants, to be honest, she said people really like or maybe better a better word would be to say seek out the episodes that evolve around difficult relationships, difficult people, difficult conversations. So I will provide you with a bit of a different perspective on this today. We will link in the show notes to all the past episodes that had to do with those difficult relationships or difficult conversations so you can catch them as well if you wanna either relisten or if you’ve never listened to them before. But what I wanted to talk to you about today is what can you do? Just like with the goals of the things that I might have in my list of goals that are not a 100% within my control, that takes away of some of my power, some of my focus because whether people will subscribe or listen to my podcast is not fully even in my control. The same is true with difficult people.

Ramona Shaw [00:06:03]:

The more that we try to think about how we can change their behavior, the more we give away our own power. Because we’re expecting and we will find satisfaction or that sense of, like, accomplishment or achievement, only when we see change in others. And whether or not someone else wants to change it’s not up to us. It’s up to them. And, actually, when it comes to behavioral change, behavioral change is pretty tough. By the way, I did a LinkedIn learning course, behavioral change. We should link to that in the show notes as well. I I’m plugging that in here as a product placement, I guess.

Ramona Shaw [00:06:41]:

So that’s 1. And behavioral change is hard. Changing trying to change someone else’s behavior is even harder, if not impossible. The other person really needs to understand that there’s an issue with a set behavior that they really want to change that behavior because they see the impact it has that they don’t wanna they don’t wanna create. And then they need to know how to change that behavior and the benefit that they will gain from having changed the behavior at the end of it. So that is a lot of work that they need to do that we can’t control. We can influence, but we can’t control it. So dead, what I wanna talk to you about today is what can you do? So all the things that you have that you have 100% control over.

Ramona Shaw [00:07:28]:

And I wanna start here. The so called the difficult people in air quotes are inevitable. We will all come across them at some point in our lives, if not over and over again. And if you have career ambitions and want to climb the ladder or have your own company or achieved something, in your field that is hard to do, you will have pushback at some point. And you will deal with people who have were driven by their egos, and hence, we call them difficult people, who are narcissists, who are, selfish, who are bullies, who have an inflated ego, and the list goes on. There is from a organizational perspective, the from a organizational structure, there’s a higher concentration of such people at the top and there are fewer people, so it’s less likely for you to be able to navigate around them. If you have a leadership team of 7 people, there’s likely someone on the leadership team who you perceive to be, again, air quote, difficult. And the sooner that you learn how to be and work with people that trigger you, that set you that you find rude or disrespectful, the easier it will be for the rest of your career to navigate such situations.

Ramona Shaw [00:08:52]:

Again, it’s inevitable. Sooner you learn it, the better for you. Now, of course, and I said this in the intro, it’s also to keep in mind that there’s a time for you to step away or walk away from such situations because it starts to negatively impact you. But let’s get to other things first. When you meet someone that you find difficult to read or difficult to interact with, answered the following questions. And, really, this should be the basics. This is the first thing to do. What do they want, and what do they like? Two crucial questions to ask yourself.

Ramona Shaw [00:09:30]:

What do they want and what do they like. And then you have to ask yourself, who or how do I want to be around them? For some people, you might say, I want to be a respect to person, I want to be assertive. I want to be loud or vocal around them. I want to be really clear on my boundaries around them. Or you could also say, I want to be someone easygoing, or I want to be casual around them or I want to be tolerant around them, or you I just wanna minimize the amount of interactions around them. Right. So whatever that is, decide for yourself who do you wanna be or how do you want to be. So after entering what do they want and what do they like, you ask yourself, who do you want to be? And then you ask 1 more question, how will I be most effective? So that is the basic set of questions you gotta ask yourself and get really clear on.

Ramona Shaw [00:10:41]:

Oftentimes, when I’m coaching clients around difficult people or difficult conversations, they’ve never really taken a moment to step back and say, okay. What do they really want? And they may say something to me like, well, they wanna have a successful department or they want to trim costs by 20% or they want to be the loudest in the room, they always wanted things to go their way, or they wanna mitigate all kinds of risks. Those are typical answers that I get. They’re all good answers. But don’t stop there. Stay with it for a moment. Why do they wanna mitigate all risks? What is it that they want to avoid, or what is it that they want to gain? Do they would they rather not lose, or would they rather win? When it’s when it’s about, cutting costs, why do they wanna cut costs? Why does this matter to them? And why now? Really get to the core of it, ask a lot of questions in your own mind to better understand their position. Do the same in what do they like? When do I see them happy? When do I see them work well with others? When do I see them at their best in terms of, like, their actual expertise or or how they show up.

Ramona Shaw [00:12:00]:

So those are things that they like. Maybe they have hobbies or other things that you wanna include there. So spanned your thinking on those 2 questions. Then get clear on how you want to show up because that will ground you and set the tone for who you are going to be in that relationship without, being reactive to them and let their reactiveness dictate however you show up. It should be your values, your principles, and a strategic play here of what do you think will work best with that person. And that ties right into that last question that I asked you to think about, which is how will I be most effective? What we don’t want to focus on is how comfortable you feel, what you would like to do that would make it the easiest or be the best case situation for you. That is less important here than to figure out how will you be the most effective. What do you need to do and not do in order to get the work done or for you to get their buy in or for you to have a relationship that where information flows 2 ways or you you can collaborate with, or a relationship where you’re not stressed all the time or reacting to them all the time.

Ramona Shaw [00:13:15]:

If that’s the end goal, how will you be most effective? K. So those are all things that you have to put on paper and not just think through it on your head, write it down. And every once in a while, when you feel challenged by that person or you’re confused of why they did what they did, pull up that document again. Read what you previously wrote. That’s why it’s really important that you write it down. And then add to it. Maybe ask more questions or add a question mark to something you said before that you’re now not sure, or add more observations with every interaction. Every time you speak to them, every time some challenge comes up, it’s a moment to learn more about them, capture it.

Ramona Shaw [00:13:57]:

Maybe also reading it will help you reframe or see the situation in a different light. As a caring and driven manager, I know you want to strengthen your leadership skills, advance your career, and lead a high performing engaged team. In. In order to do that, as a leader, you need to lead with a system, not by shooting from your hips or reacting to everyone else around you. To do so, you need to, first, learn what should go into a leadership system, and second, develop your own. Now the good news is that I teach you one must have part in your leadership system in a concise, actionable, and yet comprehensive course, focus on running successful 1 on 1 meetings with your diarched reports. It includes over 67 minutes of tactical leadership training plus a set of resources to make this as easy and immediately applicable for you as possible. You can either watch the video lessons or listen to it through a private podcast feed on your phone.

Ramona Shaw [00:14:59]:

You can get your hands on this course, which I want every single manager to have, for a nominal $19@ramonashaw.com/oneone. That’s 2 times the number one. You can check the show notes for the details or head on over to ramunashaw.com/oneone to get started right now. Now those are productive ways to engage in such a situation. What is not productive and yet what I see mo a lot of people do, you know and I’ve definitely fallen into that trap myself too because it’s a human way to behave. I’m less concerned with whether or not we’re doing it, but how fast, we notice that we’re doing it and get are able to get ourselves out of what I’m gonna call here a little bit of a a vicious cycle. So the vicious cycle that we can step into that makes work with difficult people harder than it needs to be, harder than it should be, is that we lock ourselves into the belief that we are working with a difficult person. So earlier, I kept saying, like, the quotation marks because I know that most of us will label such people as difficult people in our minds.

Ramona Shaw [00:16:12]:

The more that we say this is toxic, this person is difficult, I can’t believe they’re such a narcissist. They’re such a fool or they’re such a they’re so selfish or whatever word you use to describe them or the the relationship or the situation, the more you lock yourself into this story line. The language that you use is really powerful. The words that you repeat to yourself or in your head over and over again, they shape your way of making sense of reality. The words that you use and the associated ideas and concepts and ways of seeing and interpreting our experiences, make up our realities. So how you describe an experience, how you describe an interaction, the labels that you use, the concepts that float in your mind, the more you think about them, the more they create your reality, and and it will be their this self fulfilling prophecy. Because you’re now creating a structure of what the world is like, and your brain will naturally, that’s the way our brains are wired, will take all the information out there and see how it fits into the structure. It will not see the things that don’t fit into the fit into the structure or that would even contradict that the structure is what it is.

Ramona Shaw [00:17:42]:

This will be a fertile ground for all kinds of biases that we as humans are exposed to and affected by. So watch your words in how you talk about this person and this situation. Imagine you’re in the mountains in a house. You open the door. It’s a whole field full of fresh freshly fallen powdered snow, it comes up to your knees, and you see 2 cars on the parking lot. A really crappy Toyota Corolla and a brand new Lexus, let’s say, you wanna go to the Lexus, spread, every time you get upset, you stare at the Corolla, and you start with your feet walking towards the Corolla. And every time you think about this person being difficult, this situation being annoying, being toxic or whatever that might be, you’re walking towards the Toyota. And so the path from your house to the Toyota will become this beautifully paved path that’s really easy to walk on.

Ramona Shaw [00:18:43]:

So every time you get out of the house, your Lexus will soon be covered in snow. You won’t even see it, and the Toyota Corolla will be right there. The Lexus is still over there, and there’s maybe a few other cars right there too. There might be a Honda in there or a Volvo somewhere. But you’re walking towards a Toyota. And so all you start to see is open the house, the path to the Toyota. And that’s what you will continue to walk us. That’s all that is there and all that you see.

Ramona Shaw [00:19:10]:

So your words and the way that you describe to others, what’s going on may will feel good in the moment. But as the saying goes, it comes with a hangover. It won’t benefit you and the relationship in the long run. So be really mindful. And this is part of the skill that you have to develop in order to be effective in working with so called difficult people. The more that you buy into the story line, the harder the situation will be. It’ll be emotionally draining. You feel your energy drain.

Ramona Shaw [00:19:39]:

You feel more dressed in such situations, you likely also won’t show up at your best every time you’re interacting with them or they’re even just participating in a meeting. Your maybe your energy gets depleted or you get more nervous or whatever that may be. So you’re the one suffering from it. You’re the one who’s really taking the consequences. Because chances are that this other person doesn’t care at all, and they’re going about their day just fine, but you’re here the one navigate trying to navigate it and not feeling at your best. So your work here is fully twofold. 1, ask yourself these important questions we talked about in the beginning, and then to learn to control the narrative in your head about the situation or about this person. Be as factual as possible, identify any kind of story that you make up, interpretations that you have, things you take out of proportion.

Ramona Shaw [00:20:32]:

If you’re so far down that rabbit hole where you’re not sure what is real and what isn’t real, you can give the facts to a friend and say, what do you think about that? And if they say, I I I don’t know. It’s not a big deal happened to me before, you probably noticed that they’re not getting as triggered as you. So you have an emotional load that you carry with it. The fact is, hey. I sent them 5 emails, and they have not that they canceled the last 3 one on 1 meetings with me, someone else might say, like, yeah. They they might just be really busy. They might have something going on their personal life. I don’t know.

Ramona Shaw [00:21:05]:

I wouldn’t I wouldn’t just focus on what you do best. Let it go. Don’t worry about it. But for you, it might be such a, like, disrespectful behavior or feeling neglected, feeling devalued, whatever that may be, that’s the load that you carry. And the good news with that is you can also drop that load when you’re ready for it. So let me highlight this one more time. The skill for you to develop, and it’s if you wanna claim the ranks, the sooner that you do this, the better it’ll be for you. The more you’ll benefit is to be really mindful of the words that you use to describe this and who you talk to this about the path that you pave.

Ramona Shaw [00:21:45]:

Are you looking for a Honda or a Volvo somewhere in there? Are you or are you focused on the Lexus, or are you continuously walking to the Corolla and paving this beautiful path. Fully aware, I do this work myself too. This is easier said than done. And I have yet to meet a person who, maybe Dalai Lama and a few other boom really mastitis. Most of us, so called, like, normal people, this is likely a lifelong journey. We’ll get better at it over time, but we have to be really conscious about it. And I have a difficult relationship in my personal life or a difficult situation, I can see how, oh, it’d be so easy to walk to the Corolla, like, hold on a second. There’s gotta be Alexis.

Ramona Shaw [00:22:28]:

There’s gotta be a hundred and few other cars in between. Where are they? Let me stay open minded. Let me look for them. Let me try to walk to those cars, because I’m gonna like them better once I get there, versus defaulting to the Toyota. So we have to do this. This is deliberate work. It’s not automatic for most of us. When you aren’t able to do this, and these are in that mindset of, oh, this is really difficult.

Ramona Shaw [00:22:54]:

It’s really hard. You say if if you’re unable to do this, you likely miss out on opportunities. Opportunities to learn, opportunities for self reflection, and opportunities for personal growth. Because the growth and the that resilience mechanism that we all have built in, when we get triggered or, again, when we jump into that vicious cycle or on that vicious cycle, then that mechanism, that growth mechanism gets hijacked by by our threat and survival based systems. And and that survival based system and thinking process is supposed to be short term. So we can have a difficult interaction at this grocery store or on the freeway, and we get upset for a moment. That is okay. Right? We get triggered.

Ramona Shaw [00:23:41]:

We may curse for a second, but then we’re fine. It they’re intended to be short term. But when they’re long term and you’re in such situations and you can’t get out of it for weeks, months, some people years, that process, that hijacking will likely deplete your resources, and that’s when we start to feel either resentment and we disengage. We we may lose motivation to be there, we may get really angry and frustrated ourselves. Or we may lose confidence because we start to now doubt ourselves and whether or not we can actually live up to the job or we can handle it, or they may say things about us that we start a leaf. Also, the chances are high that we start to feel stressed out or overwhelmed or just anxious and sort of threat the Monday mornings because of such situations if they last for a long time. If you notice you’re in such a situation, new, even though even with what I just shared today here, you you’ve tried this or you will try this and it’s not getting any better. I, you know, highly recommend helping looking for help internally.

Ramona Shaw [00:24:51]:

Sometimes that is an HR department. Sometimes this is a supervisor or a trusted colleague. Watch out, though, with coworkers because that can backfire. So I’m being mindful here. If you if you have a friend that might be better, hire a coach, work with someone externally to walk through strategies and really lean into this opportunity that will help you not just in that one situation, but will help you in tricky situation, people people issues down the road as well. But seek that help. And if it that also isn’t available or doesn’t work, you have to have that tough conversation with yourself of how long am I willing and able to tolerate this, and then when am I stepping away? Some transitioning into a different department or role where you have less interaction or you’re not exposed to the situation or you’ll actually walk away. And I’ve shared this a few times here before.

Ramona Shaw [00:25:42]:

The the confidence that you built about yourself, that healthy level of confidence is a huge asset. And when you start to doubt yourself because of another person that you’re interacting with, and you start your your confidence erode, that is a warning sign. That there’s a red red flag. Hold on. This is gotta pay attention. Like, money flowing out of your bank account. You have to have that hard stop. It’s like, hold on.

Ramona Shaw [00:26:09]:

Where is this going? What are we doing here? This is not healthy. And some people who’ve been in difficult or what they would label toxic relationships for a long time. For some people, this takes a long time to rebuild that level of confidence, that they once had. This can easily be 6 to 12 months of work, of coaching, of sort of personal reflections of development or professional growth to get back into that space. So don’t take that lightly. But let’s end on a high note or on a hopeful note. The real prompt that I wanna provide here, and and I hope you pick this up is focus on the things that you can control. You’re way more served doing so.

Ramona Shaw [00:26:49]:

Ask yourself the questions, and then be mindful of the narrative in your head, the words that you use to talk about and think about this situation, and then decide from there what to do next. If you have follow-up questions, hit me up on LinkedIn or Instagram, see the show notes, or send me an email at contact at Ramona Shaw .com. If you’re interested in talking about your particular situation and you wanna engage or discuss what coaching could look like, scheduled, a strategy call will do that as well. These are good situations to leverage a coach and an external coach to help you navigate the current situation you’re dealing with, but also help you really build your own self awareness in such situations, help you understand the dynamic and help you build the skills that you’ll need to really leverage this as a learning opportunity and navigate it with greater ease in the future. So that’s the episode for today. If you’re in it to finish strong, go for it. If you’re ready to slow down and close out a year, good for you too. I hope, you’ll tune in again, though, next week with another episode of The Manager Track podcast.

Ramona Shaw [00:27:56]:

Bye for now. If you enjoyed this episode, then check out 2 other awesome resources to help you become a leader people love to work with. This includes my best selling book, the confident and competent new manager, which you can find on Amazon or at ramonasha.com/book, and a free training on how to successfully lead as a new manager. You check it out at ramona shaw.com/masterclass. These resources in a couple more, you’ll find in the show notes down below.


1. What are some strategies you can use to navigate and work with “difficult” people effectively?

2. How can focusing on what you can control, rather than trying to change others’ behavior, help in dealing with “difficult” people?

3. What are some signs that a “difficult” person or situation is negatively impacting your well-being or motivation at work?

4. Have you ever had to step away from a situation or role because of “difficult” people? What factors did you consider in making that decision?




Grab your copy of Ramona’s best-selling book ‘The Confident & Competent New Manager: How to Rapidly Rise to Success in Your First Leadership Role’: amzn.to/3TuOdcP

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Are you in your first manager role and don’t want to mess it up? Watch our FREE Masterclass and discover the 4 shifts to become a leader people love to work for: ramonashaw.com/masterclass

Don’t forget to invest time each week to increase your self-awareness, celebrate your wins, and learn from your mistakes. Your career grows only to the extent that you grow. Grab your Career Journal with leadership exercises and weekly reflections here: ramonashaw.com/shop

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