You Might Be a Bosshole® IF: You Outsource the Tough Stuff
Leadership requires courage, especially when facing difficult conversations. We've all witnessed leaders who eagerly claim credit for successes while mysteriously disappearing when tough news needs delivery. This avoidance creates a leadership vacuum that everyone notices but few dare mention - until now! Let's look at this trait that could reveal You Might Be a Bosshole®...
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The Bosshole® Chronicles
"You Might Be a Bosshole IF: You Outsource the Tough Stuff"
Original Publish Date: 4/15/2025
Hosts: John Broer and Sara Best
John Broer: Okay, let's be honest. Nobody likes delivering bad news or having difficult conversations, but if you're a manager, in order to avoid the Bosshole Zone, you've absolutely got to learn how to deliver and have those tough conversations. Well, in this episode of "You Might Be a Bosshole IF,” Sara and I are going to talk about having those tough conversations. If Sara and I are going to talk about having those tough conversations, The Bosshole Chronicles are brought to you by Real Good Ventures, the talent optimization firm helping organizations diagnose their most critical people and execution issues with world-class analytics. Make sure to check out all the resources in the show notes and be sure to follow us and share your feedback. Enjoy today's episode. Well, it's time for another installment of You Might Be a Bosshole IF I'm joined by none other than Sara Best, my good friend and business partner. Sarah tell us you might be a Bosshole if what.
Sara Best: You might be a Bosshole, John, if you delegate, outsource or otherwise avoid the messy and uncomfortable and difficult parts of leadership.
JB: Oh, okay, okay so the tough stuff.
SB: The tough stuff.
JB: Okay, so what does that include? Let's talk about it. What are some examples of that?
SB: Outsources either giving people feedback, delivering bad news, having uncomfortable conversations because they just don't want to rock the boat or they don't want to be put in a compromising position. They don't want to feel uncomfortable.
JB: This is pretty relevant because we've had some recent examples, and I actually was on the receiving end of this one time. There was a CEO and there was somebody that reported directly to the CEO and they needed to be off-boarded. They were being let go and he would not do it. He made my colleague and me take care of that and it was like dude, this is a peer of mine for all intents and purposes and you're asking us to terminate this person when you should be doing it. That's the tough stuff. That's what you're talking about there, right?
SB: Yeah, it is. I think about so many things when I consider the highest level leader having discomfort and really being afraid, if you will, or unwilling to engage in the more difficult stuff. Patrick Lencioni in his book "The Motive would say that's a reward-centered leader. A reward-centered leader is more focused on control and status and recognition and happy to outsource the difficult, messy and uncomfortable things like candor, honesty, asking tough questions, giving people tough feedback, making decisions about moving people in and out of positions and cowering from that.
JB: And.
SB: I know there's- I mean, we're messy, fallible, amazing human creatures and, for a lot of reasons, most people, including myself, I don't think we want to engage in this difficult, tense conversation, but the reality is you can't outsource that stuff, no.
JB: You can't.
SB: So in a responsibility-centered kind of leadership, you recognize that it's your duty, there's a sense of service. Like, this is my responsibility to do this, to have this conversation, to make sure I address this challenge that everybody knows about and the fallout I mean I think we've all been a part of the fallout when that doesn't happen and that particular leader loses trust and respect and credibility. Patrick Lencioni, I heard him on a maybe it was a podcast or a video some number of years ago and he said it's like the emperor with no clothes. Everyone knows they're timid, afraid, unwilling to, yet you know they kind of show up like they're not.
JB: Yes, absolutely. The words that come to mind are courage and cowardice, and I know those may those may be kind of harsh, but the responsibility-centered leader has to build that and develop that courage to be able to have those difficult conversations. It's always fun to tell somebody when they're doing great or deliver great news. It has to be proportionate to your capacity to deliver the hard news as well, and I remember having to do that as early in my career as a newly minted manager. I hated that, but I also really, and I had a good mentor who said John, this is part and parcel of the role. You have to learn how to do this, and I didn't like it. But, boy, I tell you what, once I figured out how to do it in a kind way, in a thoughtful and transparent way, it became easier. It's still not fun, but you cannot demonstrate that cowardice and offload it or delegate it to somebody else.
SB: Well, you're right, John. It's a hard truth that if you don't model accountability and addressing things and having difficult conversations, you cannot expect others, especially your leaders, to do that. It's just inappropriate. I think about Dr Travis Bradbury's work and his research around emotional intelligence. He uncovered that the higher you go in an organization, the less emotional intelligence there is, and we would suggest that emotional intelligence, skills and abilities are what support leaders in the idea of having difficult conversations et cetera, delivering bad news. But the reason being, once you get past the manager level in an organization and managers are still generally people-focused, it becomes more about results and there's kind of a bias toward behavioral patterns in that role.
Leaders who are action-oriented, autonomous, independent. So that's one challenge is it's a certain kind of person that usually fits the bill the higher you go a maverick, a captain. The other part of it is they don't get a lot of feedback. So the higher you go in an organization, the less likely it is that people are going to give you honest feedback or there isn't an automatic mechanism for that. So it kind of supports this idea that we have people that aren't equipped to continue a legacy of leading from a responsibility-centered motive versus this reward-centered motive. They're actually rewarded for being cutthroat, for getting out there, for getting results, so it makes a lot of sense. But boy, the impact on people, John. It makes it so hard for the people who are showing up and trying to do their best work.
JB: Yeah, yeah. So, Sara, let me ask you this. It sounds like for our listeners that may be thinking okay on that scale. Am I a reward-centered or responsibility-centered leader?
SB: Yeah.
JB: For those that are a little worried, it's like, oh, maybe I'm more on the reward side. I like all the good stuff and I avoid the bad stuff. Yeah.
SB: Number one sounds like self-awareness is absolutely critical EQ for sure. So where would, where would you point them if they said Sara, please help me, I'm desperate. He has created very simple, reliable, practical frameworks that if? Embraced really embraced can equip a leader to do a. So that's one thing. Yeah, definitely boost your self-awareness. Take an EQ assessment. See what capacities are supporting your leadership currently. Are there strengths you need to leverage or are there some skills that, with a little bit of effort, you could easily enhance and use more often?
JB: And I'm going to go back to something you said about feedback. We talk about feedback being the oxygen of engagement. Seek out feedback from your people. We talk a lot about that and asking those vulnerable questions about how am I helping you, but how am I holding you back. Vulnerable questions about you know how am I helping you, but how am I holding you back. And are there things that I'm avoiding as a leader that actually I need to consider? That would actually help you, but those types of questions.
SB: Well, and I think that's safe to say If you're a responsibility-centered leader, you're going to embrace this idea, hopefully that you need to ask people for feedback, because they're probably not going to give it to you.
And you need to make it safe for them to give you honest feedback. Part of the thing that would make that easier for leaders would be to say hey, so-and-so. I noticed the other day that I had a real tone in my voice and I felt frustrated and uncomfortable and I needed to come back to you and just apologize and let you know that I noticed that that happened and I understand now why I was in that state of mind. I've worked on that. Is there any feedback, any additional feedback you might have for me, cause I know that when I express things in that way, I have that tone. It tends to suck the energy out of the room. Is there anything else I should be thinking about?
JB: Yeah, that's powerful. That's good. And you made me think of something else. It was another "You Might Be a Bosshole If episode with Karen and we talked about feedback. So go back and listen to that one as well. Karen gave some great perspective. Sarah, thank you for this. This was very powerful and, I think, pretty relevant to a lot of managers out there.
SB: Amen, let's go and we'll see you next time on "You Might Be a Bosshole If.
JB: Thanks very much for checking out this episode of the Bosshole Chronicles. It was so good to have you here, and if you have your own bosshole story that you want to share with the Bosshole Transformation Nation, just reach out. You can email us at mystory@thebossholechronicles.com. Again, mystory@thebossholechronicles.com, we'll see you next time.