Ep 243: Coaching a Leader Stuck Between a Chaotic Boss and a Frustrated Team

In this episode of The Coaching Table on the Humanergy Leadership Podcast, coaches David Wheatley and Lance Satterthwaite work through a real scenario from a leader caught between a reactive C-suite and a frustrated team. Our scenarios are either submitted directly or found in the wild on public forums. The coaches explore what conversations this leader may need to have, how to calibrate expectations using CIMA, and when it's worth asking the harder question about organizational fit. Tools and frameworks mentioned are available at humanergy.com.

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Transcript

Hey, I'm Mimi, and this is The Coaching Table, brought to you by Humanergy. We've been doing leadership development and coaching work since 2000, and this series is just an extension of that. In each episode, we'll bring a real leadership situation to the table and we're going to let our coaches work it in real time. There's no prep and no script. It's just honest coaching. Our scenarios come from different places. Sometimes they're sent in and sometimes there's something we found out in the wild on a public platform.

Either way, they're real enough to matter and messy enough to be worth talking through. If you've got a scenario, go ahead and submit it on the podcast page of our website at humanergy.com and we'll handle it with care.

Hey everybody, welcome to The Coaching Table. I've got coaches with me today who between them have been doing this work for a long time. We've got David Wheatley, co-founder of Humanergy, and Lance Satterthwaite, longtime coach at Humanergy of 19 years. Thank you both for the time and for being here. Before we jump in, is there anything you want to share with our listeners about how you are approaching this? David, you can go first if you'd like.

David Wheatley: I guess I have to try and live up to my title of Chief Question Asker.

Mimi: Great. Lance?

Lance Satterthwaite: I think the approach really is effectively listen, occasionally summarize to make sure we understand, and then building on what David just said, ask really good questions, and then maybe at some point offer some perspective to be helpful.

Mimi: Great. All right, I'm going to jump into the scenario.

Lance: All right.

Mimi: "Our C-suites are all notoriously bad at structure. They are reactive people that operate strictly on a last-minute basis. They get an idea, then you have to drop what you're doing and get it done now. It's a very 'frat house' energy, and I manage a team of creatives at this company and the work we do takes time.

I know my team likes structure and wants to plan ahead, but I'm constantly being thrown curveballs by my bosses. And oftentimes those curveballs are delivered over my head and straight to my team. I'm struggling to build a system when the system above me is incompatible, and my team is often blaming me for the lack of organization, despite knowing full well that it's not my fault.

Anyone have advice? Approaching my boss or CEO is kind of out of the question here since he is the culprit. He's older and he's stuck in his ways."

David: Wow. So if I were to summarize that, it's somebody who feels a bit stuck in the middle and the leadership, the C-suite and the boss, is chaotic and they're trying to put structure in place for their team but keep being bypassed.

Lance: So one question that's on my mind. I know this person just said, hey, my boss won't change, been around a long time. I am just curious, if they want this person to do something different, what kind of conversations have they had? Or in what ways are they convinced this person will not change?

David: I'm guessing you're not going to answer for them, Mimi, is that right?

Mimi: I can't. Nope, this is definitely a bounce-ideas-off-of-each-other situation. I think Lance is right, though. Is that actually out of the question to approach the boss? Is that a fact that we know? Is that a belief or just a fact? And I guess we don't know that. And probably that person doesn't know it either.

David: So I guess I'd build on that a little bit, because my rule is I only work with the person in the room. And so I would want to know what this individual has tried, what they've done, what sets up the feelings about what they can and can't share, where's all that coming from, and what's the data behind it. Which kind of builds on what Lance is saying.

Lance: And I think, just following that one thread, there are a set of people where it's like they just wish people would mind-read and know, "I want more from you." That's like, how would you ever expect somebody else to change if at least you haven't put it in front of them? And again, maybe they have already and they've been shut down or that kind of thing.

But I think it's a worthwhile thought process to explore, which is, are you sort of expecting your boss to understand this chaotic nature and lack of proactivity that they create and how frustrating it is and the real impact of that? Or have you at least tried to explain that to the person? Because I think there are a lot of people where it's like, "I didn't even know my behavior was having that kind of impact."

And it's worthwhile to have that Green Path kind of conversation, carrying on this direct conversation to at least inform that person of both the behavior and the impact that's happening.

David: Green Path, the caring and direct conversation. I don't know about you, Lance, but how many times have you heard something like this and asked the individual, "Well, have you talked to them about it?" And they've said no, but they have spent three days coming up with conspiracy theories as to why it will be bad and what's going on and why they've got it in for me.

And so if the challenge is, "I don't know how to go talk to my boss about a behavior that they're exhibiting that's negatively impacting my ability to be successful," then part of our work should be helping them overcome whatever the obstacles are to that conversation.

So first question might be, how often do you meet with your boss and have a one-on-one conversation?

Lance: And another one, sticking with the same thought process, is just that some people, when you ask the question, "Have you talked with your boss about that?" they may say, "I did, and I did a year ago and nothing was done about it. So why would I try again?"

And so sometimes it's actually giving people a level of either motivation or at least understanding that talking about it once may not have actually made an impact. Or in what way did you talk about it? And so really, I think helping get somebody prepared for that conversation and saying, "What is the best way I'm approaching it?" And to at least believe that one and done may not be the right approach.

And again, we talked about, you know, there's productive, which is, "I tried once." There's transformative, which is, "I'm going to keep trying and I'm going to keep trying in multiple ways and multiple forums to attempt to influence a person."

David: Which goes back to that. If I'm working with the person in the room and they say, "Well, I keep asking but I'm not getting the answer I want," my challenge is, well, ask the question differently. And so let's look at the question and see if we can ask it in a different way that gets more clarity.

I think the other aspect that comes to mind as I think through the scenario is what's the dynamic between the C-suite and this employee? There's a lack of trust or a lack of belief or a lack of buy-in, because if they're taking things around them directly to their team and the team's then throwing them under the bus, there's some level of dynamic going on there that is a little unusual. So that would be another thread worthy of pulling: what's causing that.

Lance: And you're saying, David, the dynamic between C-suite and that person. And again, if you take it, there's in some ways three levels, three layers that are being talked about here. The C-suite, this person at their level that's caught in between, and then the direct reports or the teams below.

And again, I think just another thought process is, what is the right meeting and communication structure? All the way flowing from C-suite to that mid-management level to the employee level, and what does that look like? Beyond what is the right meeting communication structure, which is how does information flow down to those levels, but how does information also flow back up? I think it's an important question for people to just think about: what are our means and mechanisms, almost our structure, for being able to make that happen.

David: But this person's in the middle, so it's hard for them to drive that or ask that question, especially if they're not comfortable or confident asking the questions of their supervisor anyway. Then there's multiple threads, and one of them is to start with: what's stopping you from having the conversation that you know you need to have with your boss?

So I think that's the first piece. The second piece is this idea of what's going on with the dynamic. Has something happened that has undermined you, that people are going around you? Do people see you as resistant when you ask those things? Is there a breakdown in the chain of command? Is there structural issues that are inherently broken that are driving a different kind of behavior to the one that you might want or your team wants?

My thought pattern goes into, what's the size of this organization? Have they just gone through a step change in size? As organizations grow, they get to certain points where they structurally have to adapt.

You go from being a mom-and-pop to being a little organization, then you go from a little organization to being a slightly larger one. If the practice has been that the C-suite has been having direct conversations with people further down the chain because it was a smaller organization and now the organization's grown and they're still having those conversations, then that's something that needs to be addressed because they need to be creating the structure for those conversations rather than having them.

It'd be like if I started a business with you two and we were doing a bit of everything and then we got to 150 employees and I was still talking to the people on the floor about what they should be doing and how they should be doing it. That's probably crushing a whole bunch of folks in between us and seen as inappropriate if I was the CEO, for example.

So three things: what's them, the dynamic, and then what's the structure.

Lance: I think another potential thread to explore in this whole scenario is, so this person is like, "Hey, they're being not proactive and last minute and constantly changing." There's at least a thread to explore, which is, what is some of the root cause of that? Is it because new information is constantly entering the system and people have to adapt and change so quickly?

And so it's like, "Hey, we couldn't have predicted X, Y, or Z." And now, because that's a reality we're facing, that's what's happening. So is it a lack of good planning on the person's behalf, or is it a different reality?

I mention that because I think there are some times where people are almost so rigid and inflexible, they need everything planned out. The reality of life is it's not that way. It's not that simple. Not everything can be planned out. New information enters the system quite often. And then it's just a matter of, what sort of things can we actually control and have some influence on in terms of being proactive? But what kinds of things could we never predict that come our way that we actually do have to react and respond to?

So I do think understanding more around the root cause of what causes this reactivity and last-minute changes would be important to understand.

David: Which gets to the idea of, is there something, what's the industry? Is it an agile type of development industry where, to Lance's point, we need quick turnaround, quick reaction? We need to flatten it so that communication is strong. And is this individual somebody who wants the structure, the discipline, the one step, two step, three step, four step? In which case, you have to question whether it's a fit in the organization.

Now the other side of that could be that the fit is there because the structure for the execution of it down the line probably is very valuable. But if they're working with a lot of entrepreneurial thinkers, that's going to be a clash until they align those two things.

It's a bit like in the EOS process, they have a visionary and an implementer. And if you don't get alignment between those two, you can get confusion. If the visionary is trying to implement, they're not necessarily the right person to do it. If you're asking the implementer to come up with a vision, they're not necessarily the right fit either. So we need to get the right seat and make sure we understand what their role is and what their function is to drive the process along.

Lance: The other part I think about is what's inherent in people's personalities, right? Whether it's DiSC or Myers-Briggs or any of that. There are just some natural personality fits for people. And to understand really at all levels, the C-suite, that mid-manager, the direct report employee level, what are the various personalities?

Sometimes that has the ability to help normalize things, almost like, "Hey, we're different and we have different needs. It doesn't mean it's good or bad." So what are the personality types and how can you use that information to either understand the differences or even use some of that diversity in personality to work best as a team?

David: Yeah, there's a tool I was working on yesterday. We have this concept, a Quick Start Guide, which goes with "What Great Teams Do Great." So the first question in the setup box of "What Great Teams Do Great" is: Who are we? Do we know who's at the table and what you're bringing? Which I think is what Lance is alluding to, that do we understand the different dynamics of the characters that are part of this team?

And then you look at different ways of looking at the world. One of the ones I was thinking through yesterday is synchronous versus asynchronous. "I prefer hopping on a quick call to talk about it" versus "Send me a message so that I can digest it in my own time and then I'll reply." Understanding what the needs are from each different person on the team helps us then make that a better fit.

Lions versus wolves was another one that came out. Lions being the idea that they are much sharper in the morning, get things going in the morning. The wolves wait until the afternoon before they get energized. Those two are potentially going to clash.

And so to Lance's point, it'd be interesting to have this individual think about where they sit on some of these characteristics. And then how would they assess their colleagues on these? And what aha moments come from just looking at a set of simple dichotomies and saying, "I can see some natural tensions there."

You know, I prefer the heat, Lance prefers the cold. So if you asked us to work together, we'd probably have to find spring or fall in order for it to work. So we've got to look at all the different dynamics and make sure that we understand them and can manage them.

Lance does prefer cold, as we all know.

Mimi: So I have a question. There's this team blame dynamic. The team knows that the chaos comes from above, but still holds the person responsible. I'm just curious how you would think about that coming from someone, right? Because that might not be the full picture. So how would you pull on that thread?

Lance: Earlier, David mentioned the idea of the dynamics around trust. And so sometimes if I hear this idea of, "Hey, now this manager is being blamed for what's happening," despite the fact that they may even know it's coming from above, at least one thought I'd have is: what is the real trust and credibility that that person has with the team outside of just this issue?

Because sometimes I find there are multiple things going on there that create trust and credibility issues. And now it's like this one issue is sort of the lightning rod or the scapegoat of all these other dynamics. So I think it's just worth understanding overall: is that the only concern that this team has about this manager, or are there lots of things going on there that need to be understood and explored?

David: Yeah, it makes me think of one of the do's in the 50 Do's, which is about having the conversation the right way. And the don't is basically telling your team, "I don't believe in this, but we've just got to do it." And the do is about having the conversation up, which takes us back to the first point we made. We need to be willing to have the conversation with the C-suite, the supervisor, to say, "Hey, what's happening here? What's going on? How do I get more clarity?"

What are our expectations, and what's the differential between the structure and the flexibility, so that then I can share that with my team and set the team up for success? So if we're saying we're going to be 60% structure but 40% very rapid flexibility, then let's understand that at the next level down so that's part of the expectation.

I think one of the challenges it sounds like here is the C-suite saying 60% flexibility and this individual saying 90% structure. And they've built a team that likes the structure. And so when this flexibility comes down, we're speaking different languages and that creates frustration.

So the core of everything here is: do we have alignment? Are we sure we all understand what's really happening? And that would be the question to this individual. Have you had the chat with your supervisor? Have you got alignment? Have you thought about things like, what's the amount of structure versus flexibility that we need to operate on in order for us to be successful? And how do I get that down to my team?

So really, the coaching is helping this individual with the conversations that they need to have. And if they feel like they've already had it, how do we have that again? And if we've had it multiple times and the person at the top has said, "No, we're a hundred percent flexible and your structure gets in the way," then maybe that's a different message and the conversation goes down a completely different path.

Lance: I also think, and this could be at all three levels, Mimi, you're talking about that dynamic between the team blaming the manager. I think whether it's in the manager's eyes or even in the team's eyes, calibration, the idea of what we call CIMA. What do I control in this situation? What do I influence, or who or what do I influence? How can I mitigate or prepare more for the negative impacts of this? And then what do I just have to come to accept?

And I think that is true really at all three levels. If you're not properly calibrated, you're going to be more emotional and probably either find yourself overly frustrated or overly helpless. And neither one of those is a great approach for dealing with challenges. So then it's like, well, go through those questions, calibrate well so that you can try and be as effective as you can be in that situation. That's true for the employees, that's true of the manager, that's true of the C-suite.

David: So then if they came back, Lance, and said they were calibrated, they've got those things in place, they're trying their best, they've had the right conversations, they're still not getting anywhere, and it was also in Mimi's brief that the CEO is the ultimate culprit and it's a frat house energy, then the next question is: is there a point where we help somebody off the bus?

Lance: Which I think goes to your point of fit. Whether it's the dynamics of the organization or just the scope and the role of the job, people do have to find what fits best for them long-term. And sometimes it's like, you try and frame things up of, potentially you're in this situation as a learning opportunity. What can you learn while you stay in it?

And then part two is, if you are this unhappy because of the dynamics or because of the fit, maybe it's worth just thinking about what else would be a better fit for you. And I think sometimes the coaching does have to go there.

Okay, if you're that unhappy in this situation, actually one of the things you literally can control is updating your resume and at least exploring what else is out there, or at least what else is there at the organization that might even be a better fit.

David: Yeah, it's kind of like saying, what are the things that make you happy and energized at work? And let's list them off and then let's measure them against what you currently have. And if that's distinctly lacking, then have we tried to adjust and have we tried to fit? Then it might be a matter of, well, let's look for an organization that provides you with more of these attributes so that you can bring your best.

Because I think that's the first part of the frustration in Mimi's brief, is "I'm not able to bring my best structured work to the team because of this." And that can be incredibly frustrating, demoralizing.

So first thing is have lots of conversations, get clarity upwards, make sure we've got an understanding of what the organization is. And once you've done all that work and it's still not making progress, then get the individual to list off what makes them energized at work and measure it against what's currently there. And then leave a long pause as they recognize the fact that this might not be the ideal workplace for them.

Mimi: So one other thing that I noticed in the description is just that there's definitely a bubbling over of frustration. And that creates a lot of those Red Path behaviors that we like to talk about. So I'm wondering about your thoughts around that in this scenario.

Lance: And you're saying, Mimi, the frustrations of the manager, frustrations of the employees, everybody?

Mimi: The manager that wrote the scenario, the person that's asking for the help. There's clearly a lot of bubbling up of frustration that's going on. And it's triggered them to say things like "frat house" energy and "I'm constantly being thrown curveballs." There's just obviously a level of exasperation there, and what happens when folks get to that level?

Lance: Yeah. I think a part of the handling of the frustration is their own, for lack of a better word, stress management technique. If we use the phrase "straws that break the camel's back," it's not the straw, it's the load. And so they have to manage essentially their own frustration levels. Whether it's through talking it out with people or exercising or listening to music or whatever it is that helps them sort of lighten their own load.

And I think the other part of frustration level is sometimes people amplify their own frustration based on their expectations. I always think about, like, a doctor. If two people make an appointment with a doctor at 10 o'clock, if one thinks they're going to see the doctor at 10 o'clock, by 10:15 they're completely frustrated. If somebody else is like, "Hey, if I get to see the doctor by 10:30, that would be great," by 10:15 they're still cool, calm, and collected. And that had nothing to do with the doctor. That actually had everything to do with their own expectations.

And so for this particular person, I do think you have to get inside their mind and say, what are your real expectations? And there may be some unrealistic expectations there, or inflexible and rigid expectations, where they're setting themselves up to become more frustrated just because of what's inside their head. So I think at times, at least exploring that is super helpful for people.

David: That drives back to what Lance shared earlier, CIMA, that calibration tool. And the reason we calibrate tools is to make sure we can trust them. So CIMA is the tool to make sure I can trust my thinking. So do I stop to create that calibration and check in on those things?

And then you brought up the Red Path, Green Path, which is available at the tools section of humanergy.com for those that aren't familiar. The Red Path, Green Path, if you're feeling some of the Red Path behaviors, the avoidance, the anger, defensiveness, all of those things that bubble up, then the drive is to double down on the Green Path.

And I think you could look at the Green Path and say it's a pretty good summary of what Lance and I have been sharing. But the first thing is, do we understand? Have we listened enough to understand what's really happening? And then there's a bullet that does a heavy lift, which is engage, align, learn, and coordinate. The engage bit, we've been saying, "Hey, you've got to talk to people and make sure you're aligned." So let's do the engagement and let's get the alignment so then we can learn and we can coordinate coming forward.

And as Lance made the point earlier, it might be that the supervisor has never had this feedback and says, "Wow, that's great. I really appreciate that. We need to realign. We need to coordinate differently as we move forward. We need to create a better plan as we go."

But every time I feel that Red Path bubbling, it's a reminder to double down, well, first CIMA and calibrate myself, and then double down on the Green Path and make sure I'm listening to understand, I'm engaging, I'm aligning, I'm learning, and coordinating.

Lance: I think maybe even in your follow-up question, the way they're framing this around some absolutes of "never" and "always." Just even bringing some awareness to them. It's like, yes, you're certainly frustrated, that comes across in that message. And how does that get conveyed or communicated?

What does that look like in a real workplace? Sometimes people are griping about it behind the scenes, again not taking it directly. It's like helping somebody just to recognize, are you on the Red Path yourself, either in your thinking or behavior? And is it time to change it? Again, the time to change it is all the stuff that David just talked about. What sort of conversations, and with whom, and how do you want to go about approaching those? That's all a part of that Green Path.

David: And there's some subtleties in that as well. Even thinking about, to Lance's point, how are you approaching it? What's your attitude when you're having that conversation? How's that coming across?

I had a great coaching session recently with somebody, and we were looking at the difference between saying "why" and saying "what's causing that." And it was kind of fascinating because as she was working through it, her expression, her whole physiology with "why" was more kind of pointed, a little bit more aggressive and expectant. And then when she went to "well, what's causing that?" it was a whole lot more open and curious.

So just thinking about what is it about you when you go into these conversations that is creating any kind of impact, that means people are working around you, that people aren't giving you all the information, that people aren't giving you the clarity. And so setting this individual up to be able to go in and have that conversation and stay on the Green Path while they're having that conversation with their supervisor and the CEO, I think is what this coaching session is about. Now we understand where we need to have the alignment. How do we help this individual have that in a way that they come away feeling good about, and having understood how they might be very different in character to the people that they're talking to and approaching how they're talking to them?

Mimi: Any other threads that you guys are feeling like you want to pull on in this?

Lance: My only other thought is, in this scenario, we're talking about a person first starting with being centered themselves so that then they can effectively deal with what's going on, both essentially upstream from them as well as downstream. And so as a part of this whole coaching process, I think there's actually a real, if they appreciate and enjoy structure, there's a way of trying to help them create a structure, which is:

There's three elements that we're talking about here. Number one is how do you manage yourself and the way you are thinking about this? Number two, how are you going to have those upstream conversations with your supervisor or who you believe is causing it? And then part three is managing your team's perception where you're being blamed for this reactive dynamic. What are you going to do there?

So I actually think there's a lot of meat that you can put on the bones here for this person, because they like so much structure, and just say, all right, here are your three avenues and here are essentially your actions coming out of that in each of those three areas.

David: There's another place, as you posed that last question there, Mimi, that it would be interesting to know who we're sat in front of exactly. So usually in our coaching engagements, we have a bit of an understanding of who that is. And the language of "frat house energy" in my mind has a different take if I'm sat in front of a man or a woman. And so then it gets into what does that mean for each of those individuals differently and potentially the gender difference that goes on with that language.

But I'll leave the therapy to my therapy friend Lance.

Mimi: Well, I'll give you this last moment to give it another thought if there's anything else you want to unpack or share with our listeners.

Lance: My one last thought is sometimes I find in coaching, if we don't understand the size of the problem for this particular person, it's like, hey, on a scale of 1 to 10, how big of a deal is it? Are you coming right now because this is a mildly annoying problem and you just want to vent and talk through it? Or is this like, you know what, if this doesn't change, I'm about ready to quit my job?

I think trying to scale and understand the size of the problem, as well as at times helping the person put the size of the problem into perspective, is important. It's like, yes, I understand this is frustrating, it's annoying, it's difficult. And in the challenges that you experience in life, how big or small is this in comparison? Because I think that shapes some of the coaching that we do with a person.

And my own experience in coaching is sometimes people just want a place to vent and then they just move on. You thought it was a really big problem. So I think just trying to understand that is super helpful.

David: Yeah. And I just point people to a few places. One of them is episode 106 of the Humanergy Leadership Podcast, which is actually our very own Lance Satterthwaite talking about CIMA in some more detail. That would be the first step, that CIMA calibration. There's a lot on the podcast about Green Path.

And I echo what Lance just said: let's just make sure we understand what's the level of this conversation. And then at the end of the coaching conversation, we've got a clear next step as to what they want to do in terms of getting clarity and alignment with the right people.

Mimi: Great. Well, Lance and David, thank you both so much for your time today. That is our show, everyone. And if anything from today's conversation got you thinking, that is kind of the point.

If your organization could use this kind of thinking in real time, that's what we're here for. Head to humanergy.com to learn more about our coaching and our leadership development work. You can learn more about David and Lance on the website on their bio pages. And if you've got a leadership situation that you'd like us to work through on a future episode, go ahead and submit that on our website on the podcast page. We'll keep it anonymous and keep it real, and we'll take it from there. Thanks, everybody.

David: Thanks, Mimi. Thanks, Lance.

Lance: Thank you.