In this YouTube conversation, AM Jazzy asks how to communicate with people who are difficult to work with, such as customers, bosses, or team members. Stephen responds by emphasizing three core mindsets: (1) putting yourself in the other person's shoes to understand their wants and motivations; (2) recognizing that personality differences are natural and tolerating them, while seeking mentorship or an independent perspective when the relationship becomes strained; and (3) being honest, vulnerable, and direct about the issues, "getting the moose on the table" to surface problems and break them down. Evan adds a fourth mindset: taking full personal responsibility for the interaction, avoiding the habit of labeling others as "difficult" which shifts blame away from yourself. He argues that assuming responsibility and approaching the conversation with the intent to navigate it successfully leads to better outcomes. The dialogue blends behavioral‑psychology insights with practical advice for entrepreneurs and team members, encouraging empathy, open dialogue, mentorship, and self‑accountability as the keys to effective communication with challenging colleagues or customers.
AM Jazzy 96. How do we communicate with people who are difficult to work with when we have to? Ooh, what do you think?
Wow. Yeah, that's diff— and now, God, there's loads of behavioral psychology on this. And I guess, hey, AM Jazzy, it sounds like it's an environment with customers. I'll be honest, I've I never find them hard to communicate, especially we talk about social media. It sounds like when you get in the situation, it might not be for you guys, but if you've got a relationship that's a bit prickly with your boss or something like that, then that is a position that can be a bit feisty. So I think it comes back to some of the basics Evan's touched on, is number one, we kind of have to put ourselves at the center of the conversation and put ourselves in their shoes and then ask ourselves, you know, what is it they want and why are they kind of behaving the way they are? Because normally, you know, things are pretty logical. And then the other thing that's, you know, touching on all the sort of behavioral psychology stuff is, you know, reality is the beauty of the world is everybody's got a different personality. And the reality is different personality types, some get on with each other, Some want to go to a Blue Jays game, you know, all the time, and they want to hang out and drink beer. Some people don't want to do that. Some people want to listen to music. Some people want to read books. And therefore, you know, I just think we've got to accept that one of the beauties in life is we're totally different. And I think the tolerance of that is definitely good. Now, if it all gets tough, you know, I think that there's loads of stuff you can do. In terms of go to a mentor, ask someone sort of independent, kind of, this is happening, this is a situation. It could be with a customer, it could be with one of your work colleagues, someone who works for you as an entrepreneur. And particularly if you're an entrepreneur and you're asking someone in the team to do something and it's kind of not landing or it's poor quality or they're letting customers down, I can understand that hurts. And then because what we said before, it's very personal. You know, it's very personal. You guys sacrifice a lot. You work long hours, you pursue your dreams, and you want everybody to pull the same level of weight as you do in terms of, you know, that idea that you're trying to get to market. So there's other ways to help. So I'd go for some mentorship. And then ultimately, if you kind of work out what is the kind of clock that's ticking within the person that's been challenging, I'd always advocate being honest with people and say, you know, I don't think there's anything— there's someone, someone taught me once, you know, there's probably no bad people around. It's just sometimes the behaviors really upset us. And I think if you sat down with someone and said, look, you know, person, for whatever reason, kind of, we're not getting on. I kind of think broadly we want the same things. I want to build this company. I want to, I want to be the next Google. I want everybody in the company to follow this dream. Let's just be honest with each other. What's not clicking? What's not working? Because, you know, I'm not perfect. I think this is where you can use a bit of sort of self-deprecation and show a bit of vulnerability. I'm not perfect, but, you know, what is it that's kind of getting in the way here? Because we all want the same things, but we're bumping into each other. So what can we do to just, you know, surface it, as they say in Canada? Get that moose on the table, get that moose on the table, and then we, we can break it into a thousand pieces and we can consume it and sort it out and move on. Yeah, I don't know, Evan, how it is?
There it is again, that, that customization to the audience. I love it. Um, I mean, I agree with everything Stephen's saying. I almost want to just kind of copy and paste, and like, I would encourage you guys to watch that clip back again. Those three points he made were really good. The only thing I would add to it is I go into every situation trying to take full responsibility. And I think if you abdicate responsibility is when you start to lose in all situations. But here, as an example, as soon as you label somebody difficult, you're saying it's, it's their fault, right? It's their problem. They're the one who's hard to deal with. They're difficult. And that reduces some of the responsibility on you. To navigate the situation. Where if you just play back that last piece Stephen was talking about is that, look, everybody's a human being. There's no bad people. They just have different circumstances, different upbringings, different values. And if you take the responsibility to say, I want to navigate this, I want to make it a success, put it on yourself to figure it out, then just going in with that different mindset I think can really help you have more success in the conversation. On top of, Everything else you've been talking about, getting the mentor, trying to understand them, put yourself in their shoes. It was really great. See, I think I might have to watch back that answer too. I'm gonna bookmark that one. I like that one. That was really good.
