Leveraging Leadership

Listener Question: How to Handle a Boss Who Won’t Listen

• Emily Sander • Season 1 • Episode 176

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Emily answers a question from someone struggling to work with a new boss at a family-owned business who ignores process, oversells services, and doesn't value their input. She shares practical advice on "increment training"—giving the boss positive feedback for following the right process and building small wins over time. Emily tells her own story about working with a difficult, charismatic sales leader and highlights the importance of meeting halfway, using patience, and looking for ways to turn friction into teamwork.


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Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want. 

 

Time Stamps:

01:11 Challenges with the New Boss
02:38 Possible Reasons for the Boss's Behavior
06:12 Training the Boss Incrementally
07:27 Personal Story: Handling a Similar Situation
13:53 Conclusion and Final Advice

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We have another listener question that was emailed in, and by the way, this makes my day when I get a email that says, Hey, can you do this for one of the episodes? So if you have any questions that are top of mind for you or something you're actually going through that you want an episode on, then please, please, please feel free to email me at emily@nextlevel.coach, and I will certainly do an episode on your topic. But here's the question the person has asked to remain anonymous, which I will absolutely honor. But here is the question. Hey Emily. I am at a family owned business that's been around for close to 45 years. I've been here 19 of those. I started on the sales team and worked my way up, and now I basically run point on everything, internal sales ops, actual sales team, fulfillment, commissions, contracting, the whole deal. If something needs to happen, it usually runs through me. Here's the thing, my boss is now the founder's son. He's honestly a great sales guy. I'll give him that. He can work a room charm, a crowd close deals with his buddies over beers and golf, but he sells stuff we don't actually do. Or he oversells things that could be done, but not the way he's pitching it. And then the stuff hits the fan from me and my team, and we try to make it all work. I've tried bringing him into process conversations. I've showed him how these missteps are slowing us down, confusing customers and making it harder to scale. He brushes it off like I'm overthinking it, and the part that really gets me, I'll bring up an idea and he'll straight up say, that's not an idea. Then one of his boys will bring up the exact same thing and suddenly it's genius. It's exhausting. Do, do, do. He also says stuff like, you don't talk to me. You don't listen. Which is crazy because I've worked my butt off for this company. I know every piece of this business. His dad, the original founder, and I had a great relationship. He respected me. He listened to me and he ran the business. Well, this guy. Has been here 18 months and he's more about spotlight and schmoozing and doesn't see the value in what I bring, even though he keeps piling more and more on my plate. So I guess my question is how do I get through to someone like that? Okay. First of all, I hear you. I feel you. I have been in similar situations and I have seen this happen. This is a thing, so this is a legit thing, and you're not alone. One of the things that might be happening here, just as a backdrop, is he might be threatened by you and how much you know. And what I mean by that is I'm not sure of the situation with his dad and, the son, but you said the dad was the original founder and he ran a pretty, tight ship. So I'm assuming that the founder, like, knew all the ins and outs of the business and he was in it from the beginning and everything organically grew up around him and the business matured. I'm not sure where the sun was in this process, so I'm not sure if the sun was involved in the company or if he was off doing something else and he was just brought in closer to the company more recently in the last year and a half. But it might be the sun doesn't know a lot about the business and if you put yourself in his shoes, it could be embarrassing. It could be a little embarrassing, like He thinks that he should know more. He thinks that other people think that he should know more. He's been put in charge and he probably knows that it's because he's the guy's son and they probably have the same name. And so like there's all that dynamic going on where I don't know, like I actually don't know the most about my own business and my dad did. So there's that whole dynamic that you should be aware of. Maybe it's a different situation. Maybe it's a totally different dynamic. maybe the son's been involved for the whole time and that's just how he is and maybe he's been promoted to more of an official role in the last 18 months'cause the data is stepping back. I don't know. But that's just something I wanna throw out there because I've seen this happen, in similar situations where that's a thing and sometimes it doesn't clock, it doesn't register for the other person. So I just wanted to get that out there. Just in case it's a thing. The second part of this. So what to do, what I've found to be helpful in these situations with these types of people is to compliment them on the things they do well. So you said he's legitimately a good salesperson, like he can schmooze, he builds rapport, he has connections, he has network. I. That's huge. That is an advantage for a company and every company needs effective salespeople. So if that's one of his strengths and one of his areas of strengths, then compliment him on that sincerely. The other thing you want to highlight and give kudos around and talk him up about is when he does things that helps the company and the team. So when he does do things that it's like, okay, here is the proper handoff to my delivery teams. Here's the way you contract things. Here's the template you use, here's the language we wanna use, and all these things. When he does that, and maybe it's like once out of a hundred times. The one time he does that, throw massive kudos at him, highlight the fact that he did it. Say, Hey, this was amazing. Here's what happened because of it. And you can do it on one-on-one calls. You can do it on group calls in front of people. You can do it in front of the customer, you can send him emails, you can send him text messages, whatever. Gets through to him, and it might be more than one of those things, but highlight the fact that here's like what we need to have happen and you did a good job. Like thank you for when you did this. And that is kind of like patting him on the head and like puffing up a little bit. But he might not understand what you're talking about, which might seem strange to you. And it might be like he can't possibly not know. Sometimes they don't know, sometimes they don't get it until it's like, oh. This is the thing. Okay, we're not, this is the thing you do, and that's what they like. Okay. That's what needs to happen. Got it. I think then they'll forget again. Then they might do it a couple more times. Great job. Like, thank you so much for getting this contract in this way. Thank you for using the template. We streamline that and we're already deploying the customer. Okay. When I do that thing, things go well. Okay. When I do that thing, they like that. Okay, so it might take that, what you're doing in this process is you're training him in increments. You're training him in increments over time. Would it be easier if you sat him down and it sounds like you have going, here's the process, here's the overall like workflow. Here's my chart, here's where you fit in the process, here's the handoff points and you gotta do it this way. And he is like, oh, got it. And thank you for showing me the whole picture. Now it makes sense. Now I'm gonna do those things. That would be much easier. That would be great for everyone. Some people can do that. Some people like that. Some people that just, they don't get that, or that's not how they learn or they're just not willing to do it at that point. And so it might take this incremental process over time, over a long period of time that they finally get it. And or there's enough pain along the way where it's, okay, we, I have an unhappy customer. That's my buddy. That's my friend I played golf with, and now I have to explain and like internally, like people are squawking at me. Like, okay, fine. It might take a few of those to get it back on. On track and be like, okay, I do it this way, things go smoothly. I do it this way. Internal teams are happy. I do it this way. Revenue grows faster. I do it this way. My commission is bigger, like over and over and over again. And you just highlight those different points all across the process. I'll tell you a quick story. I had a similar situation to this early in my career. So there was a founder, he was one of our co-founders, and he. Had a healthy ego. He wanted to stay in the business, a lot of elements and forces were saying, you can't be in the business. But he remained on the sales side because like this individual you're describing, he could sell anything to anyone at any time. He was just like, it was like a God given gift. He had charisma and charm like. Oozing out of him. It didn't hurt. He looked like George Clooney's brother, and it didn't hurt. He had these like amazing blue eyes that just kind of sucked you in against your will. It was weird, like it was a weird thing with men and women. He just had these eyes and he could, when he turned it on, man, you were kind of helpless. He had that thing where. He could make you feel like the center of the universe and like, so important and so good about yourself. It was, it was very odd. But similar to your boss, he sold stuff like we didn't have. And I was like, bill, I'll call him Bill. Like, bill, you know, we don't have that. You've been yelled at for that many times. Stop doing that shit like please. And at this point. The board was getting after him and the board was saying like, if you keep doing this, like we will have no choice but to remove you from the company. Like you're causing so much churn on our customers and so much churn on our internal teams. Like, this is your last chance. And we went to a conference and we were meeting with this large prospect and we kind of, grabbed the leader of this company for the prospect and then our CEO and I. Went outside and we sat at a table outside. And I remember Bill, we were walking to the table. He kind of pulled outta the chair for me to sit in and he like, gestured for me to sit here. And I was like, okay. Like whatever. Maybe a gentlemanly, gestured. Haven't seen you done this before. But cool. And Bill sat across from me. And then the CEO sat to my right and the prospect sat to my left and Bill kept his sunglasses on, which was a little bit strange'cause normally he liked to show off his eyes'cause he knew the effect it had on people. But it was a sunny day. So it was like, okay, whatever. Not a huge deal. I. And we were talking. We were talking, we were talking, and we got to the point about, the onboarding process. So this prospect was well along in the sales process and they just wanted to hear about like, what, like you said, it's a smooth delivery. You said it's a smooth onboarding process. It's not gonna create a lot of thrash on my team. I don't want a lot of downtime between, systems. How fast can you get us ramped up? And so Bill started answering this and the CEO and I were like. Here we go. This is where Bill gets off the rails and goes off the reservation sometimes. Let's see what he is gonna do. Like please do a good job so the board isn't gonna freak out and, and fire you. And he said a few kind of overarching sentences and descriptions and he paused. And then he kept going and then he paused and then he got into like the detailed area where he was like, Emily would be the best person to talk about this.'cause I was in charge of that team. And so I said a little bit and he kind of, subtly and very nicely like redirected the conversation like, Hey Emily, you know, let's talk about this part of the. Process. And I was like, oh, okay. Because he knew what was important to this prospect was this one part of the process, not the part that I was used to talking about. And I was like, okay, I'm gonna talk about this part. No problem. Great. And then I kicked it back over to Bill and he said a few things paused and I was like, oh God. And he said a few more things. I was like, Nope, nope, nope, nope, nope. And so I suddenly did like a. A head shake, just very subtle, not obvious, just like, Nope, nope, nope. And he stopped and then he said something else and I was like, yes. Like, thank you. Okay. Yes. And like kind of relief on my face. And he kept talking and he kept talking. And then did that same thing where he like went down one. Rabbit hole in one vein of thought. And I was like, no. Like, no. So I kind of did a shake and he stopped and he rerouted. And then I saw you are looking at me through your sunglasses, so your head is pointed toward the prospect, but your eyes are looking at me and you're picking up my cues.'cause you don't wanna get it wrong and you wanna get this part right. And so I was like. Oh, okay. Got it. So I would do these little like, kind of like motions, kind of like, Nope. Yep, yes. Smile like, mm-hmm. Like look down, like, Nope, not quite. And then he would kick it back over to me. For some parts, I would answer some about the onboarding delivery process. Our CEO would chime in and we all kind of like all three of us. From our company kind of understood what was happening and we were giving each other clues about kind of where we wanted to go with the conversation. And I was like, oh, cool. And afterward the prospect got up, shook hands and left. And Bill came up to me and just said, you know, I, I liked how you did that subtle, you know, head shake or head nod. And I was like, uh, thank you. You're welcome. No problem. Okay. And then he just walked away. I was like, please don't get fired from the board'cause then you'll be mad. But that was something where. Similar to this situation, we had to find our way about things, and I remember that meeting we had, that outdoor meeting we had, because after that, things were a little bit different between Bill and the teams. I. I don't wanna try to like overplay that where like, this was like the watershed moment and everything was fine and we were best friends. That was not the case. But we did have like a level of understanding where, you know, now we can communicate. And now he knows that he can come to me with questions. I'm not gonna embarrass him. I'm just gonna like, subtly kind of do little motions to him on calls. And he brought me on more sales calls after that just to kind of like subtly, you know, guide him in the right direction. And I had to get used to the fact that he's selling this stuff and he would say things where it's like. Like, okay, that's very salesy. I thought of it as smarmy and it was like, okay, it's not technically wrong. like, I wouldn't say it like that, but you're making it sound like amazing and like the best possible version of this thing it could possibly be. And that's your job and that is your job. And I had to like sit there and be fine with that and be glad about that. It's not technically wrong, it's maybe pushing the envelope in certain places, but we can still deliver to that. And I had to get used to like just hearing that over and over, like let him do his thing. Let him be charming. Let him ooze, charisma. Let me watch this process happen over and over again where people like wanna be mad at him and want to not buy things from him, and then he convinces them to do it and I'm like, wow. So we had to kind of find our way about that. But we got there and it, wasn't, again, best friends, but we got to the point where like we understood. How to do it and we did it. So all to say this person, your new boss is new to the organization. They might be like trying to learn about the business the best they can. And they have this person who like knows every single thing. It's like, oh my gosh. Like that can be threatening or unsettling or just like, uh, I don't wanna deal with that. Some people like to assert their authority over that. Well, like, you know, guess what? I am who I am and I have, you know, the name on the building, so I'm just gonna. Push this stuff through. So think about your delivery. How you deliver information, how it's gonna land best for this person. Do think about it from their shoes if you can. I know it's like, sometimes it's, it's like I don't wanna sympathize with you, but sometimes like, oh, okay. No, actually that is kind of a tough spot to be in. Okay, let me try to meet you halfway and go about it. That way they have to come meet you a little bit of the way as well. So it's not you doing everything for them, but meet'em halfway, see what happens, and then compliment them for the. The legitimate strengths they bring to the table and compliment them when they follow the process and do things the right way and hand off things the right way. and then try to find like a common ground and a common language. And the thing that you're looking for is the switch of. We're kind of against each other or we're butting heads all the time, or this is someone I always have to fight through to get deals through, like just a pain in the butt when I work hard to sell this stuff and I'm talking to my friends and then I have to jam it through and it's just so painful. Go from that to. I have an ally over there. I kind of gotta toe the line. I gotta walk the line on my end,'cause they're gonna keep me to it. But if I have a question, I can go to'em. If I do a little misstep, they're not gonna jump down my throat. They're gonna redirect it. they tell me, they kinda let me know when I'm going in the right direction or doing the right types of things. I'm picking that up as I go along. Things are getting better and over time it'll be to the point where like, okay, he might go, I do it this way. Things are streamlined. I do it this way and revenue happens sooner. I do it this way and my commission gets paid out sooner. I do it this way and internal teams don't yell at me, and so over time you find the way to do that. So hopefully that helps. I know this is a tough situation and I've been in situations like that and I've seen people in situations like that, and there are moments where it's not fun. I fully appreciate that part of it. Hopefully some of these things are things you can apply and try out, and hopefully they work for you and over time as this person gets settled in and as they figure out, okay, here's how we're gonna operate together, you find that kind of dance you can do or your, your allies in this together where you each bring something to the table and it actually compliments the other person. All right, so thank you so much for your question and again, if anyone else is listening and has a question, then feel free to email me. I love answering listener questions. It's very fun. And, uh, you can shoot me an email at Emily at Next Level Coach, and I'll catch you next time on Leveraging Leadership. I.