How Do I Deal with a Difficult Boss? | Coaching Real Leaders

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0:52I'm Muriel Wilkins and this is Coaching Real Leaders, part of the HBR Podcast Network. I'm a longtime executive coach who works with highly successful leaders who've hit a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them so that hopefully they can lead with a little more ease. I typically work with clients over the course of several months, but on this show, we have a one-time coaching meeting focusing on a specific leadership challenge they're facing.

1:27Today's guest is someone we'll call Benjamin to protect his confidentiality. He's been mission-driven for a long time and has a real interest in helping people. Really, it was in college. I would see a lot of pictures up of different, you know, humanitarian aid things internationally. And it would actually, like, I would almost get stomach pain just thinking about the need out there in the world. You know, people especially without access to resources or that were struggling. Finally, I literally quit school to go and jump in. Just kind of didn't look back and eventually had to go back to school.

2:04But it was just kind of just a passion thing for people out there that were struggling. Benjamin has spent the bulk of his career so far working internationally with humanitarian focused organizations. He moved his way up to middle management and recently landed his first senior leadership role at a nonprofit. But I was itching to get back to like really helping people in a direct way. I heard about this nonprofit up in here where I am now, mainly helping people in recovery. And I just fell in love with the mission and then the founder. She wouldn't take no for an answer. It was a huge step up for me because I was kind of like middle management with very little kind of impact in the overall organization.

2:51And lo and behold, there's a medium sized but growing nonprofit bringing me on as the executive director, supposedly taking over for the founder. And so I love the mission. I love the model. And so those are the things I jumped in. I said, let's do this. But yeah, a lot has just gone really downhill. Benjamin reached out because while he's excited about his new role and has all this passion for the job and the people it serves, he's running into some trouble dealing with the founder of the organization. So I started by asking him to share a bit more about how things have gone downhill for him.

3:35the founder of the organization that brought me on she was going to move on after a while when i got in she just you know really encouraging but we had one employee and it's funny because the founder told me that this employee was taking advantage of the organization not showing up to work, not supporting her role. But then when I would step in, the founder would then change her mind. So there's that part. And then just the micromanaging of the founder. There's just some like real hardcore, like really adding complexity to the issue. I came in, like I told you with this full full steam ahead. You know, they weren't quantifying goals.

4:23They weren't even looking at outcomes, outputs, anything. And I was like, well, let's do this. Let's, you know, quantify stuff. Let's set up goals. But she would come in afterwards and then question that in front of all the employees behind my back. And then the employees just wouldn't know what to do. I went to the board. This episode is brought to you by Palmolive. Family time isn't just the big moments. It's weeknight dinners, sitting around the table, everyone talking all at once. So when the plates are empty and the sink is full, use Palmolive Ultra. Palmolive's most powerful formula removes up to 99.9 % of grease, leaving your dishes sparkling clean.

5:06And the new convenient pump makes cleaning even easier, so you can spend less time tackling dishes and more time together. Shop now at palmolive.com. Propel Fitness Water with Gatorade electrolytes, zero sugar and vitamins. Propel hydrates better than water to help you get the most out of your workout and get back to your best self. What propels you? Propel with Gatorade electrolytes. Okay, so there is a board. There is a board. I went to the board. I had been trying so hard. I've been trying so hard to be direct. and I remembered one of your podcasts Muriel you talked about there was somebody that they were struggling because they kept leaving an organization every time they didn't feel valued or they didn't feel like it was novel I was like I don't want to be that person you talked about being resilient and I'm like I'm not going to be that person that that is not resilient I did every like I direct conversations finally I went to the board and their response was we know and so now I'm just like, like things are just so complex.

6:13They're just this cycle with this founder. I just don't feel like it's about the mission anymore. I feel like it's more about the founder trying to keep the organization the same, you know, not impact more people. And I'm like, looking to move elsewhere, but it just breaks my heart. And I feel like maybe a failure and I don't want this to happen again. Now I'm like job applications everywhere. How do I stop this sort of thing from happening? Is there something wrong with me? Okay. So there's a lot there, right? And so I first want to acknowledge what it sounds like is a pretty challenging situation that you find yourself in you moved to join an organization that seemed like one where you were very aligned with the mission and then you join and it's kind of like you know the wizard of oz you pull back the curtain and it's, oh, not quite what I thought it would be, right?

7:26So I think there's that element. And then there's the other element that, at least in my experience, coaching people who have stepped in and worked with founders, sometimes it can be tricky, right? If those relationships aren't sort of explicitly, consciously constructed or contracted for from the get-go. Like really tricky in any situation and it has to be carefully transitioned. So I just want to acknowledge just from a baseline standpoint, this isn't sort of, oh, what do you mean? Like you're just dealing with management 101 issues. I want to calibrate. It's not like, like, I just want to calibrate that you're, you know, you sort of walked into what you thought was a 5k race and instead of you're running a marathon.

8:22Okay. That actually happened to a friend of mine. Oh my gosh. We both went to a race. I was doing the half marathon. She was doing the 5k, but then she took the wrong turn. She missed the turn and ended up running a whole half marathon. Right. Oh my gosh. But she did it. So, but at some point she figured out that's what she was doing. And I think for you, I'm bringing this up because I want you to ground in the reality of it. The reality of it is it's not a sort of baseline, regular, you know, management 101 type of thing. Okay. And then the other thing you mentioned is around resilience, right?

9:01And is this a reflection of whether you have the resilience to deal with something like this? You know, there's a thin line between resilience and just being plain old stubborn.

9:18So we want to make sure you're operating on the right side of things. OK? That's great. OK. So what is it that you want to have happen? What would make you feel like? Propel Fitness Water with Gatorade electrolytes, zero sugar and vitamins. Propel hydrates better than water to help you get the most out of your workout and get back to your best self. What propels you? Propel with Gatorade Electrolytes. When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications and more.

9:58Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs. You have some form of positive outcomes for you coming out of this conversation. Man, I just want to learn from this and then come into something else, maybe be able to find. I would just love a healthy team, like how to look for a better fit, because like you noted, this organization was a great fit for me.

10:41You know, it, it leaned on past experience and a passion of mine with the mission, but it's just not being heard. And I just like, I should have seen it. You know, you feel like you should have seen red flags, like, Oh, that's something you gotta watch out for or like i need to nip this in the bud i guess the question is how do you look for a better situation yeah yeah okay i get it you know and you mentioned before like kind of the feeling uh a little bit of well i don't know if it's a little bit you know a failure and how do you keep this from happening which inherent in the question of how do you keep this from happening you know I I hear an assumption in there that you could have kept this from happening yeah and I don't know like could you have kept this from happening that's a hard question I mean you know obviously I've learned if there is a founder involved you know to be very cautious if not you know insistent that they maybe step away for a time but you know it just didn't seem like this was going to be a problem at the beginning because we were so in sync it seemed you know and plus that would have been a probably seemed inappropriate and offensive at the time to be like i'll come in but you need to leave or something like that Mm hmm.

12:13Mm hmm. OK. So I don't know. Yeah, you don't. Exactly. You don't know. You don't know. I mean, you know, Benjamin, what's amazing to me here is like you have spent your whole career working with people in the most vulnerable of situations. And if any of those folks came to you and said, hey, I should have kept this from happening, right? Like, I should have kept myself from falling into this situation of poverty or finding myself homeless or what would you say to them? that is such a great question well i would tell them that yesterday is yesterday that we didn't all have a fair shake and that there's a big opportunity for them to use this in their story moving forward you know actually as a story of overcoming great challenges that it can inspire many people like them.

13:24Great. So a story of overcoming challenges. Now, here's the thing. I'm hearing your side of it, okay? I don't have the founder in front of me to be able to say, okay, what's the deal? What did Benjamin do, not do? So I am fully cognizant that there are many, many sides to every situation. And again, I'm not saying there's a right or a wrong side. I'm saying there are many sides, right? And so the situation you find yourself in is co-created. It's like the weather, you know, when we wake up one day and, you know, what we're experiencing now on the West Coast and they have all this, you know, cold weather and snow and all this stuff.

14:06And you're like, what happened? Well, you know, it's a combination of factors that just happened to all meet at that particular time. That. Propel Fitness Water with Gatorade electrolytes, zero sugar, and vitamins. Propel hydrates better than water to help you get the most out of your workout and get back to your best self. What propels you? Propel with Gatorade electrolytes. When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications, and more.

14:43Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs. We're a long time in the making. OK. And so, yes, you brought your piece of the weather. She brought hers, both of which were a long time in the making. and now you're in this situation. Okay. So I'm not absolving anyone from their part of it. Everybody has a part of it. Could you have asked other questions that maybe would have given you a clue?

15:27Could you have done some other due diligence on this person that maybe could have given you a clue? Could you have not taken that job? Yeah, there's a lot of could have, would have, right? But you didn't and you're here. And so I think just like you said, you would say to some of the folks that you work with, you know, what is your story going to be? What is the story that you want to write in terms of overcoming this challenge moving forward? So when I ask you that, what is the story you want to write? Well, one thing I've learned is not to over-idealize how an organization should work, kind of seeing that organizations have a little bit of family in them, especially if they've been standing a while.

16:14There's like some baked in relational things that are pretty complex. And I think that I came to this with a framework that didn't allow for that. So I would love to learn from that in the future to be able to not come in so much like a wrecking ball of like, let's do this. We're all on the same page, right? Let's go out there. Let's measure the impact. And I would love for that to be a lesson that I could learn to go in and be more of a student of not just how it works, but relationally how things are. Well, let's sort of use, you know, this situation as a laboratory for that. What do you think you could have done that would have made you more of a student early on to understand not just how the organization works in terms of its delivery model, but also, you know, relationally how it operates?

17:06What could you have done that's different than what you did do? Yeah, I think one of the things I could have done is, and this is what I'm seeing from a lot of executive directors, is you get put in and it's all on you. It's like you're like a catch-all for all of the to-do lists. And so a lot of times I see we just jump in and I just jumped in and it was about me and my performance, transforming the organization and moving along the calendar. And a lot of that is the board. And even the founder herself was telling me, we need to do this and this and this, but to be able to stop for a second and not be such an individual performer, and not be so focused on what I bring in and having really nice board reports, you know, instead being like, well, let's hold on a second.

18:00Like, and not just getting to know people on a relational to have a relationship with me, but also, you know, examining how they interact with each other and just kind of get a feeling, you know, I would love to learn that skill to like see how they mesh together so I can respect it. Yeah. Well, I love that you used the word student, right? And so when you think about what makes an effective student, what is it that enables somebody to be an effective student? What skills are they using? Wow, that's great. I think there has to be a sense of humility. There's something to learn, you know, because you're actually trying to learn and you're trying to study and listen and just have a sense of anticipation that there is something to be learned.

18:53And that's kind of the opposite of the individual performer. Like, I'm going to get these numbers and I'm going to blow the socks of the board. This episode is brought to you by Palmolive. Family time isn't just the big moments. It's weeknight dinners, sitting around the table, everyone talking all at once. So when the plates are empty and the sink is full, use Palmolive Ultra. Palmolive's most powerful formula removes up to 99.9 % of grease, leaving your dishes sparkling clean. And the new convenient pump makes cleaning even easier, so you can spend less time tackling dishes and more time together.

19:28Shop now at palmolive.com. Propel Fitness Water. With Gatorade electrolytes, zero sugar, and vitamins, Propel hydrates better than water to help you get the most out of your workout. and get back to your best self. What propels you? Propel with Gatorade Electrolytes. The board even criticized me. They said, there's nothing in your board report that's vulnerable. Like, where's the section of how you're struggling? I'm like, I didn't think I was supposed to tell you guys where I was struggling, you know? Yeah, I mean, look, I think you, you know, I think you hit the nail on the head, right? Like, it's actually a balance, right?

20:03If you think about someone being an effective student, You know, I have kids who are in school, you know, and well, what does it mean? They do need to do the work. Like, it's not like, you know, you have homework, so it's not like, oh, no work. You have to do the work, which it sounds like you were great at that. You jumped right in to do the work. But then there's this piece of like, you're also there to learn something. You know, as you said, there's an anticipation to learn, which means that I actually believe I have something to learn. If you don't believe you have something to learn, you have left the station of being a student a long time ago.

20:41OK. And how do you learn? You learn by doing and you learn also by listening and by asking questions. so to your charge for yourself around how can i come in as a leader and both deliver and be a student so that i can pick up on the relational aspects and you know the delivery aspects i don't know you tell me like how much time did you spend listening and asking questions when you first came on board you know it was from a different perspective it was more like how can I personally form a relationship with people rather than how these things work. And I'm really, I kind of, I came in with a bias because I came in and they hadn't been very effective in a lot of areas.

21:34So I'm realizing that I assumed that they kind of weren't as good at their job or something. You know what I mean? Like, I assume that there were some inherent problems. And so now that you're talking, it's helping me see that I automatically assumed that it wasn't going to be helpful to study their relationships or how they were doing things, because obviously they weren't doing it like really, really well. And so let's just like move forward.

22:07A big part of what happens in coaching is self-reflection. You get an increased sense of self-awareness, which is critical before anyone can move to action. While Benjamin was eager to get some tips on how to deal with the issues he's facing, it was important that he see what his contribution has been to the situation. His ability and willingness to take a hard look at his own behaviors set the stage for a more productive coaching session. He finds himself in a situation that many people face at one time or another throughout their career. the experience of taking a job feeling like it's the perfect fit and having things go a different way.

22:45Benjamin came into the role with a lot of expectations, looking to show that he could do a great job in this leadership position and move the organization in a certain direction. His frustration at things not going the way he had envisioned is understandable, but it's also holding him hostage. By turning the focus on what he can do differently moving forward, it would allow him to regain some of his footing. Let's jump back in as I ask Benjamin how he can leverage his past experiences to strengthen how he approaches his leadership today, especially as it pertains to his team.

23:22To me, what's coming up as you're talking, Benjamin, is like, I think that there's such a comparison to the direct impact work that you've done as a humanitarian, right? And you mentioned that you've worked with people in recovery. And so when you work with people in recovery or you work with people in, again, very vulnerable situation, survival situation from a humanitarian standpoint, what is the mindset that you go in with in order to really be able to support them? that is a great comparison because you definitely would not go in thinking well obviously what you've done in the past hasn't worked so we're just gonna plow through your recovery and yeah I personally don't have that perspective about someone in recovery I have the most respect for their bravery and you know it's a cycle it's not always linear their progress and so but I didn't come to that, send with my own employees or the people I worked with, you know, it was not respectful of the efforts they had in the past.

24:28So that is really a great insight. So if you came in, right, let's say it's day one here or day one at your next place, and you approach it from what seems to be a pretty authentic leadership approach that you have, You've just applied it in one area and not so much in another. What would be the difference in terms of how you approach your employees? Well, I would be curious, you know, about their own goals and their own frustrations and their own, you know, what's worked well for them in the past, what's not working so well. I would just, you know, be more of a student of, yeah, how they felt in the organization, how their relationships were, and yeah, to build that community and not be so hyper-focused on performance and on things that seem impressive on a balance sheet or on a P &L.

25:32Okay. Again, it is a balance, right? Like, yes, you want to do all that. And at some point you need to deliver as well. OK. And I'm curious, what is it that you feel because you mentioned it a few times, sort of this you were very driven to perform, to show the value? Like, what is it that drove you to lean on that side of it more, that bias that you said versus the let me also learn and meet folks where they are? you know, to be honest, a lot of it was just that this was, like I said, one of the biggest leadership roles I've had. And I did have people even in my own family that were doubtful, you know, that I could handle such a large role overseeing so many things.

26:26And then even just showing kind of like an ROI for my wife and my kids, you know, like I moved them. It's funny, Like I just really needed it to work and I really needed to be able to show something for it. And now it's not working, but it's like, like, I just really. Yeah, I just wanted to prove that I could do it, you know. Yeah. You wanted to prove that you could do it. Mm-hmm. Which I don't think, if we go back to the beginning of our conversation, proving that you could do this doesn't sound to me like that was the mission you were drawn to. Mm-hmm. Yeah. And yet, that's what you made your mission.

27:19So true. Yeah. So I think there's this question here, right, around moving forward. Mm-hmm. being really clear about what your mission is, you know, and then staying aligned to that. And by the way, if look, sometimes your mission is going to be I need to prove that I can do this, you know, right? Like, I need to prove to myself that I can present something or, you know, run a race or whatever it is. Okay, fine. Then align your actions with that. But when there's dissonance, when you're saying, hey, here's the mission I'm here to serve. But really, there's this whole other mission that you're serving.

28:01Things don't add up. Yeah, I can definitely see that. It definitely started with a narrative of it's kind of like that hero's journey, right? Versus what the real mission that drew me out here was, which was to help people. And I can see how those can distract one from the other. and so I don't want to go into another place like a wrecking ball with it all being about what I can accomplish. So you're still at your current organization, right? Yes. Okay. So I think there's a bit of like, for the time that you have there, how can you make it work for you? because have you decided definitely definitely you're leaving i'm maybe 70 on leaving but there i'm not 100 no yeah okay and i'm neither here nor there right like it's whatever you want at this point in terms of what that looks like but for the time being for today you're there until you get to 100 % that you're leaving or you get to 100 % that you're staying, that decision will come one day.

29:17So my question to you is, while you're there, what would it look like for you to lead in a way that is fully aligned to the mission that you originally came with? Yeah. In spite of this founder that you're dealing with? well it would make it less about how frustrated i am it makes sense now why like i'm just completely frustrated about not being able to achieve goals you know because in my heart it has been about me achieving goals and it would be more about how do i learn from the people i work with about how it's going for them just really focus on the mission while still trying to get help somehow and accomplishing these goals that have gotten very, very complex.

30:14And so at a tactical level, at a concrete level, like what would that look like for you tomorrow if you went in with that mindset? Well, it would look like spending time with the people I work with beyond the founder and beyond the program director. and just, I know this isn't concrete, but falling in love again with what we get to do and just really focusing on the mission standpoint of how we're doing, spending more time with the people that we serve, probably bringing that mindset going forward. And Benjamin, that doesn't mean that you need to be in denial around the reality of the founder, right?

30:58That's not what I'm suggesting at all. This is not like, oh, you know, just use positive thinking and think about the good stuff and forget the bad stuff. That's not what this is at all. This is about finding your anchor during the storm. You are there right now. And so why are you there right now? What is going to be your purpose during this very difficult time? What is going to hold you there in a way that doesn't suck you up in this feeling of frustration that you've had? Where can you find your calm? Because it's clear you have found the frustration. yeah so i think you were at a place of like where do you find your calm where do you find the part that's going to continue to drive you you know it's almost like um coming back to home base like what's your home base that's so good you know and it sounds like it's something that's been a common thread for you your whole profession which is helping people and now it's not just helping people in terms of, you know, the folks that you serve, but also helping people within your organization, your employees, your teams, et cetera, wherever you might be able to.