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Dealing with Difficult Personalities at Work

Posted June 25, 2024

Hana Jacover, Leadership, Executive, and Performance Coach, joins our host, Camela Thompson, Go-To-Market Thought Leader, and B2B Insights Expert, in this episode of the Revenue Marketing Report. Hana shares how to take steps to align sales and marketing, spot a difficult personality, and know when to avoid conflict.

I was grinning earlier because both on the agency and internal sides, I’m sure you have had a lot of experience with our topic, which is dealing with difficult personalities. It is a bit of an art form.

“Oh yes. There are many, many different personalities. I’m grateful that I have had exposure to not only a variety of organizations, how they operate, what the team looks like, leadership style, and all of that. But specifically working with different personalities and having them be your client where you really have to understand who they are, their motivations on top of the organizational goals, culture and how things work at that level. I feel grateful to have had that exposure and be able to build my toolkit around it.”

It builds character. I have lots of character. We don’t need anymore characters. I am thinking of the topics that many B2B marketers have faced themselves when in a meeting with the sales leader and they’re pretty confrontational about what they feel marketing is doing for them. Maybe we could talk through the sales vs. marketing conflict.

“Yes, it’s funny! This was actually my expertise for a long time. I did a lot of lead management, a lot of facilitating around lead management, which at the end of the day is alignment between sales and marketing. The way that I look at this team relationship as well as the individual is common goals. Really understanding what the driver is, and what’s the common goal? What is the common goal of marketing? Where are the similarities? Where are the gaps and what are some of the definitions that are around that? Because even when you’ve got a goal, there are words that are being used that can be somewhat subjective.

“When we have these common goals, we also need to look at the language that we are using and we also need to look at the motivation. There are these layers. It’s not enough to create a goal that everyone agrees on. We have to understand, well, what does that word mean to you? What does that word mean to us? How do we build alignment around that? That is where I feel it starts, just an understanding of goals and motivators and how they’re seeing things.”

I love that you started there for so many reasons. I feel a lot of the conflict I’ve seen as a result of not getting on the same page about how to define what’s a lead.


It is such a simple thing but it’s not. It’s really not.

“Yes, it is not. You do have to sit down and this is why organizations would hire us since we would facilitate those conversations because there is conflict. And conflict, unless you have experience with it, is often viewed as a very negative thing and is often something where people lose their ability to regulate their emotions. That is where a lot of the ego comes into the room. That is where a lot of the butting heads come into the room.

“To have somebody come in and listen to the words that are being used. Put aside some of the emotions and actually listen to what is being said and who is hearing what and who isn’t hearing what, and then say, okay, here’s where we’re going to start. We are going to start by defining what is a lead. Okay, marketing, you tell me the exact steps someone goes through in your funnel. And then you tell me, what that handoff looks like exactly. Then, you tell me sales, what exactly you do after that.

“Just learning the landscape, which I think is a missed step in lots of situations. Hey sales leader, do you understand this process? Hey marketing leader, do you understand the process the lead actually goes through? Maybe that will help us come to some sort of alignment around, okay, here’s where a lead isn’t working, where this definition doesn’t make sense, or where this word doesn’t make sense, or where there is a gap.”

Yes. I have seen plenty of baggage get in the way of having clear unemotional conversations. Sometimes, if one of the team’s displaying good faith and communicating, we’re trying to improve this, and we really want your help. We want to collaborate on this. And they are still getting a lot of water cooler talk and saying one thing and doing another. Many times, that can be baggage from past experience, past leadership in that company, or past experience at other companies. This is a lot harder to deal with.

“Yes. Essentially, what Camela is describing is something I would run into in every client engagement. Part of the reason why I wanted to go into coaching is because you see this. You’re watching it and you know it has nothing to do with marketing. It has nothing to do with sales. It has everything to do with the individual and the way that they are showing up and the way that you’re processing things. The way they are communicating.

“For me, I was drawn to that part of things, which obviously led me into coaching. But Camela is right. It has everything in a lot of cases, or at least where I think people are challenged with conflict is they need to turn inward in those moments and separate what’s going on there, for me, and how am I showing up in this situation and am I bringing some things into this situation that aren’t serving the purpose that we all have that aren’t positively serving me? And breaking those things down is a difficult process to do. Some people also don’t have the awareness of that as well.”

Yes. It’s so hard to deal with that as an individual contributor who doesn’t have positional authority, I mean, at times, you should start with a conversation with them, but now and then, that isn’t the healthiest approach for you. Do we want to talk a little bit about knowing when to have a direct one-on-one with somebody vs. perhaps talking to their manager or my manager because I’m not sure how to handle this.

“Yes. I feel these are some definite red flags. Most people know what an abrasive leader or person looks like and if you start to understand what emotional regulation looks like, for example, you can see this play out. If you can see a pattern of someone who isn’t emotionally regulated, there’s nothing that you can really do. I mean you can bring your regulation and calm, which in those situations, if you’re an individual contributor, you are usually not calm. You are nervous and fearful. If you can bring your own emotional regulation, that is a great invitation for somebody else to be regulated. 

“There’s a theory about how when we’re regulated, it actually helps others become and stay regulated. However, it is not your job. It is unlikely that anything you say will change that individual’s behavior since if they’re activated they’re not hearing you. So many things happen when our brains are activated. We go into our fight-or-flight state. The way we operate changes. The way we receive information changes. The way we make decisions changes. If you can see if someone’s activated right now, then you can say this probably won’t be a productive conversation. Or they don’t seem activated, they seem calm and regulated. I feel they’re open to discussion. I know how they communicate, and you’ve to know how to communicate with them and, yeah, there might be an opportunity. But if you’re trying to bring them down in terms of activation and emotional response, if you’re trying to bring somebody down when they are activated, and you don’t have the skillset to do that, then it’s probably not in your best interest to have that conversation then and there.”

Yes. I like that Hana pointed that out because it is so easy to further escalate the situation with facial expressions and body language. You may not even be aware of what’s happening if you’re nervous or kind of scared. So shutting down the conversation is going to be productive. Let’s talk about this other time and figure out where a different way seems like a good approach. I have been in both of those scenarios where the conversation was fine and the conversation wasn’t fine.

“And again, you’re not in control of the other person’s emotions and their emotional regulation. It just goes to show why what works for yourself is important. The ability to stay regulated in those moments is the most important thing that you can do since it applies to all areas of your life, not just your job.”

And asking somebody what’s going on or why this is difficult for them, that’s not good to do at the moment all the time too. That is tough. self-awareness is hard when you’re activated.

“Yes. The problem in this scenario becomes if you don’t have a culture of continuous feedback, if you don’t have a culture where you are always giving feedback in the form of maybe 360 reviews or pulse checks, something like that, where people are getting a chance to observe how others perceive them, then it’s harder for them to see it since you want people to see what they can’t see.

“There are only so many ways that you can go about that in a way that again, doesn’t put you in the direct line of conflict and you don’t end up as collateral damage. There has to be a culture built around that. So you can go to your manager and say, hey, I’ve some feedback or this is the experience that I had, ect., etc. Yet, if there’s no process in place, then for your manager to share that feedback or for you to share that feedback anonymously and know that something is going to happen with it, then that’s right. It doesn’t really get you anywhere. I would say too that’s something, it’s a great question to ask when you’re doing interviews. It is a great question to understand what that process looks like. What does that feedback loop look like for people within my team and those outside of my team?”

And it is almost easier when they’re obvious about it and do it in front of everyone since there’s corroboration that it actually happened. Whereas when they’re saying one thing and then doing another in private, it’s so much harder to deal with. Hana, thank you so much!

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