How to Win Over a Difficult Person

career coach career coaching difficult boss difficult person tech leader power lunch Jan 25, 2021

Transcript of the Video: 


I've got some really fun, tough love for you today. The topic today is ‘How to win over a difficult person’, whether that is a boss, a teammate, a coworker, a customer, even someone that you've worked with in the past that you're no longer working with, and kind of feeling a hangover effect from that. And it's impacting your job search or whatever your goals are right now. 


  • I'm going to give you a quick introduction if we haven't met yet.
  • We'll talk about what is a difficult person,
  • why are they difficult,
  • the impact of them being difficult, and then
  • three steps to win them over.

If we haven't met yet, my name is Melisa Liberman. I'm a career coach for tech leaders. And I am a former tech executive, I helped build a SaaS software company to a quarter of a billion-dollar exit. I love the software world. I love corporate America. And I am now a full-time coach and I have been a coach and a consultant for the last eight years, helping other tech leaders get what they want out of their career, just like I've been able to do in mind. So, with that, let's jump in and talk about today's topic. 

What is a “difficult” person?

For most of us, someone we're working with, usually, at least one difficult person, if not many, right? We encounter so many people that in our world, might be labeled as:

  • micromanager
  • someone who has beyond crazy unrealistic expectations.
  • Or maybe they're a backstabber,
  • or they're always defensive when you're trying to work with them,
  • or they just don't communicate at all and you end up kind of holding the bag at the end of the day.
  • Or maybe they agree with you, but have literally no intention of following through when they've agreed.
  • Or they could be someone who changes their mind a lot,
  • or someone who you see as making bad decisions is an apt,
  • someone who's never satisfied no matter what you do, how you do it, what techniques you try.

When I'm talking about a difficult person, those are the types of things that come to mind. So, before I move on, think about it for you.. What else what makes it difficult person?

What I'm not talking about today is:

  • someone who's engaging in some form of illegal behavior, like sexual harassment or
  • discrimination or
  • other types of illegal behavior.

I'm talking about someone who's labeled as a difficult person, because they're hard to get along with, hard to work with, hard to work for, etc. You never feel like you're doing the right thing where you can never get ahead with them.

Who’s Your Difficult Person? 

As we go through today's exercise, think of one person - there's no right or wrong here - just think of one person. It could be your mother-in-law, your boss, someone you manage, or a customer. Write them down, and then we'll go through some exercises here, after we talk a little bit more about what makes a person difficult. So now that you have your person in mind, I have so tough love for you.

Why Are They Difficult?

We mark those people as difficult because of the way we're interpreting their behavior. So, in other words, they're not intrinsically difficult. It's not their behavior that's making them difficult. It's our thoughts about how they behave, that makes them difficult in our mind, we make them difficult.

I want that to sink in a little bit, because the next point is really going to home in on this concept. We're the one who's making them difficult. It's not what they're doing. It's how we're interpreting what they're doing. And you might tell me, I'm crazy, you might be angry right now, but hear me out. Because this concept I struggled with, toward the end of my corporate career, it really, I cannot tell you more strongly how much time I wasted because I didn't understand this. And it made my life so much more difficult.

So, with that in mind, I would love to dive further into this concept of it's our own perception of the person, not the person themselves.

A really good way to look at it and kind of loosen up, perhaps, is to think about a time when you have two people do the same exact thing. One person is difficult in your mind, and one person is not difficult in your mind. And it might not just be you, right? The whole company might think they're difficult, but it's still a construct a mental construct, we've all labeled them with their difficult.

Think about a time when two people - one difficult one not difficult - missed a deadline or change their mind or gave really hard feedback.

How did you handle that? Generally, the answer to that question is the person who's a non-difficult person, you gave them a pass of some sort, you gave them the benefit of the doubt, right?

The non-difference is the difficult person, the person that you see is being difficult. You added that to your pile of evidence that they're difficult, and it just further increase ingrained in your mind that this person is a difficult person.

And I'm using the word view right now, there are many of you on here, and we're all doing this. I am calling all of us out collectively here, because I know how much impact positive impact seeing this can give for you. So ,when I say you, it might call you out specifically, but I'm telling you, everyone's doing this in some way form or fashion, whether it's our mother in law, or our, you know, CEO, or whomever it is.

What happens when you're thinking or labeling them as being difficult?

Like I said, as humans, we're scanning for evidence that we're right, by human nature, the way our brain works, we're scanning for evidence to prove ourselves that we're right. So, when we decide someone's difficult, then we're looking for all that evidence to make ourselves right, to show that show that they're difficult, and it ends up compounding it. And we end up believing they're difficult because we're finding all of that evidence, and it creates negative emotion for ourselves.

  • It makes us angry, right or
  • frustrated or
  • feeling obligated or
  • exasperated, that we're tricky.
  • I think I got it right, or hopeless.

And so it ends up creating a life that's difficult for us, right? It's not the difficult person, we've made things difficult for ourselves. 

So, with this negative emotion, we change the way that we interact with the person, which again makes our life more difficult. When we're thinking this person is difficult, I have all this proof. Other people even are saying this person is difficult. If we end up take taking actions or inactions by thinking that, then lead us to procrastinate right, or to avoid them or to complain about them. I will be completely honest with you, I know I can't even - I don't even want to add up the number of hours I probably wasted over a two-year period, complaining about the CFO of my old company and all of the bad behavior in ineptness that was occurring at the time. And there were a lot of CFOs at that company. So, you know, it's really, really a place where it becomes this kind of self-fulfilling, self-growing situation, right? You're making your own life more difficult by thinking the guy is difficult, or the person the girl is difficult, by then feeling so hopeless or angry or frustrated. And that causes you to avoid them or complain about them are overcompensates? And that then makes your own life more difficult. It is not the person who's difficult who's causing this.

What do we do? 

We can't change the difficult person where he's not even difficult, really, at the end of the day, it's our perception of him, right? So, what are we left with here? This seems like really bleak, a bleak information set of information I'm giving you but it's not I promise you.

 How can we neutralize, even win over the difficult person?

…even though we can't change them, by literally just three steps.

They very simple. They're not easy. In most cases.

  1. Recognizing this is our perception, it's our thought about the person is the label of the person, it's not the truth of the person, the black, you know, the all or nothing thinking.
  2. Acknowledging that we have control over our perception - we can decide how we want to perceive that person, do we want to think of them as difficult? And, therefore make it really hard to interact with them? Or do we want to look at it a different way to loosen some of that up, so we're not procrastinating? We're not avoiding, we're not spinning out of control and wasting so much time and energy, you know, just commiserating about the difficult person versus finding a productive, productive way to work with that person.
  3. Figure out from your place of knowing you have control over the situation to figure out how do you want to feel in that in working with them and interacting with them? And how do you want to show up with in that in that professional relationship, without blaming them without attributing your feelings or your actions or inactions to that label of them being difficult.

Let me give you a little bit more underneath this. Because again, like I said, it's a simple concept, but it's not easy to implement. Essentially, in a nutshell, in order to win over a difficult person, we essentially need to win over ourselves, we need to get out of the blame mode. And to see that this label of being difficult is not a fact, it's just a perception. And something that we've been building evidence for over time, because we had that perception. So, it seems even more real, and probably some people agree with us. But in order to get through this situation and make it more productive, and show up in the way that you want to which I assume is not avoiding procrastinating, blaming, commiserating all of the taking up so much of your energy for really no benefit. In order to get out of all of that mode, we have to get into a solution focus mode.

And this isn't about judging ourselves, like we shouldn't be doing this or that person shouldn't be this way. It's just literally about saying I have control over the situation, because of the way I'm looking at it. And I can get myself out of blaming that person and feeling like I have no control in the situation into more of a solution focus mode.

Does this mean I’m Condoning or Enabling?

Now, let me take a pause here. Because you might be saying, Melisa, this person is my superior or my customer and I don't have any control. My hands are tied. I definitely even if they're not my superior or my customer, I don't want to condone or enable this bad behavior. And I shouldn't have to be the one who has to change. They should have to be the one who has to change because they're the one who's difficult.

I will tell you again, I spent a lot of time in one of these thoughts if not all of them and it literally gives no result you are thinking that you're condoning their behavior or somehow punishing them.

You being angry - you know, all those feelings we talked about: angry, passive, aggressive, frustrated - doesn't fix or change them.

What does fix the situation and allows you to show up in the way that you want to show up is in a clear-headed way without judgment is by knowing that you have control over the way you're thinking of them, the way you're perceiving them the way you're labeling them, and freeing your mind up to have a clear headed solution without judgment. 

Example 1

I have a client who has a who came to me and said, I have a demanding, unpredictable CEO. His thoughts about the CEO are: he's crazy, he's disrespectful, he's unrealistic, he's unchanging, he's constantly being late to meetings, changing priorities, skipping meetings, scheduling meetings without any context - just all of this bad behavior, right? We could label him as this right? 

But having that label and having this idea that all of these things are in place, he's disrespectful, he's unrealistic, and leads literally to that client having no solution, or if you're in the same situation, having no solution, because it feels so unmoving. Right? So factual that is, that is maybe not the crazy part. But that is disrespectful.

And on top of it, he's the superior, right. So, it feels like I don't have any control. In this situation, I'm stuck, I either need to learn to live with it, or I need to find a new job. But instead, as we started peeling back the layers, we realized for that client and it could be for you, too, that he was actually enabling this crazy in a way, because he was feeling like this CEO, no matter what the CEO is difficult. And I have to live within his difficult rules in order to keep my job here. And what we realized is that was so many people pleasing going on from these thought processes about the CEO. When he started looking at it more objectively, from the sense of this is not an in movable situation, the CEO isn't difficult, and therefore I'm stuck. We were able to start asking so many better questions.

  • How was he contributing to the crazy? How was he literally dropping everything every time and answering the phone every time the CEO called? And was that really necessary? It turns out, it wasn't he thought it was absolutely necessary. We figured out it isn't difficult. And when he stopped doing that, he ended up getting so much more respect from the CEO. But his brain wasn't even able to go to that kind of solution or to that kind of concept, because he just felt like this was a difficult CEO a difficult person in a difficult situation on winnable situation.
  • What about this difficult behavior? The label of difficult behavior is truly impacting me, my client, versus what am I just thinking the CEO should do? And therefore, kind of making the problem harder, right? It turns out a lot of this stuff, this bad behavior, really didn't impact my client whatsoever. But he was getting so angry and so frustrated, and so feeling so helpless, because if he felt like the CEO should be working in a certain way, when we dropped all of that, that, that stuff's not impacting my client, my impacting my client’s team, and just focused on what can I what is impacting him? And what can you know, what are some solutions we could go through to to work this out with the CEO, the problem became so much smaller, much smaller, it wasn't a difficult person anymore that we were trying to solve. It was these three or four behaviors and interactions that needed to get adjusted. So again, getting out of the fixed mindset of this is a difficult person a difficult situation into a solution-oriented situation.

Example 2 

The time you may have this to where an employee agrees with the request you give them they say they're going to go do it. They're going to go have this conversation with a peer that they've had a conflict with. They're going to go deliver some batteries to a customer, they're going to do whatever, but then they never follow through. Whether this is an employee or a customer or a peer or a superior, it doesn't really matter, most of us can relate to this situation. The thought about this employee or whoever that person is, can be things like they're unreliable, they're disrespectful, they're never going to get it. There's no solution to this, they're a difficult person.

If you able to take a step back and say, they're not a difficult person, this is how I'm looking. The way I'm looking at this and perceiving it, is what's causing me to feel like it's a fixed situation that I can address. In order to look at this differently looking at it and saying, Okay, this isn't fixed, this isn't. This isn't a difficult person, you know, quote, unquote, opening your mind and saying,

  • How am I setting up the scenario where transparency isn't welcome? Maybe it isn't, because they're, quote unquote, difficult? Maybe it's because I'm not creating a situation where I'm welcoming transparency?
  • How can I be a better mentor to this employee? or How can I better open up a dialogue with this peer who keeps telling me they're going to do something but they're not? Or a customer? Where can I opening up your mind to say, where can I start adjusting the scenario? Where can I find solutions to work through this becomes so much more productive than just labeling them as difficult and feeling like there's nothing, we can do? 

Example 3

The scenario where a customer's constantly changing their mind. They're not even acknowledging it. They're like, “What are you talking about? I told you this all along”, and you're like, “No, I know, for a fact this is different.” Or they're adjusting the scope, or the time frame or the or the budget, and one of those three elements, but really not adjusting the overall right, if you change the scope, you need to change the timeframe, in most cases, right. These call these customers that are constantly changing their mind and just not budging, they, we will, it's so common to label them as difficult, or they're not trustworthy, or maybe they're inept. And it becomes this fixed situation where it feels like you have no solution. But if you can see that this is partially if this is all your interpretation of this customer, another person might go work with a customer, right and think they're amazing. It's your interpretation of the customer, which again, isn't you're not doing anything right or wrong. It's just human nature. But when you're interpreting them as inept or untrustworthy, it shuts down your ability to find solutions for the situation. So instead of thinking in that fixed away, look at it from the perspective of

  • how can you help the client remember that original commitments?
  • What do you impact? Again, that same question, as it said, on number one, what are you truly impacted by versus you just thinking they should operate a certain way in order to be trustworthy or qualified, and therefore forcing that solution, even though it is it doesn't even at the end of the day matter?

Those are three examples of how this concept works and how you can apply it in a way that allows it gives you really productive questions to ask yourself, that help you to find solutions to this problem situation, versus just labeling someone as difficult and kind of shutting down as a result.

In summary, the three steps to win over the difficult person, and I put the, you know, the summary is in a lot of ways a difficult person is you your thoughts about this other person, that's not them, they're not, you know, you can't go to the zoo and look at them and see a label there. The giraffe, the alligator, the difficult person, right? It's you are interpreting them as a difficult person. And I say it with love. We all are doing this. I've shared with you my own examples here.

  1. Recognizing that difficult label isn't a fact or fix, which is great news. Because that's what gives you control and power back in the situation. After you recognize that and see where you're seeing them as difficult is a perception is a label you've given them then move to step two,
  2. which is define how you really want to think and feel and act toward that person. Again, without them changing. The CEO is going to keep barging in. He's going to keep missing the meetings. The customers keep changing their mind without that person changing, how do you want to think and feel and act toward them. I was talking to a client the other day, and he was thinking about this person who was kind of in bucket number two would agree with him appear would agree with him and then never do what they agreed on. And he was feeling really, this feeling like he was untrustworthy, he was feeling discouraged, like, Who is this person I'm working with, I'm never gonna figure this out. And as we started working through step two, he wanted to feel connected to this person like he that they could work together. Again, he's never going to get to that point, if he thinks like, this guy is a difficult person and is never trustworthy, it causes him to shut down, and really just avoid the person at all costs, right? So as we started working through it, we realize he really wanted to feel connected to this person feel trusting of this person. And then that allowed us to start figuring out other ways of looking at this, like the questions I gave you in those three examples. Or some other questions you can ask yourself that I've given you here, which is, you know, let's just even assume that the some of the people are difficult, and we can't get past the point of this label. They're just difficult. Everyone agrees they feel difficult. What if that's true? What if you can't kind of nudge through this, like we've talked about on those past three examples? Then think about it just from another perspective to start with? How can this person benefit you? What can you control in this situation? What are the insecure? This is a this is a key right here? What about this person that you're labeling as difficult? Or things that you're actually insecure about yourself? What are you reflecting or putting on them? That's really all about you and your own insecurities? I could give you the entire tech leader power lunch on that topic alone.
  3. What skills can you develop at working with this person that will help you now in the future? And then if you master these skills? How would that change your relationship with that yourself with the difficult person that you've labeled and with others? This hopefully gives you a framework that you can use to approach the situation, whether it's a professional one or a personal one, and just start becoming less of an all or nothing thinking and into more of a, you know, a gray area? Nothing? is a factor fixed in the situation? That's difficult that you've labeled as difficult. There is a gray area and how can you start operating in that gray area, so that you're not showing up as, as avoiding the situation or procrastinating it or wanting to just escape the situation altogether? How can you use this situation to grow and to develop more skills, and to find ways to work with that individual in a more solution oriented way, versus in a fixed mindset way.

So, as I said at the beginning, this isn't, this isn't very simple, but it's not easy. But I will tell you from personal experience, I promise you that this worth work is worth it, whether it's a professional relationship, or a personal relationship, or all of the above.


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