How Delivering Tough Feedback to a $500M Startup Star Strengthened Team Trust

Um, I had to deliver feedback, uh, to a peer of mine. About how my team members, you know, felt that um This fear was sort of telling them directly what to do. Um, and not necessarily respecting their expertise or, you know, seeking their feedback on the best way to do it, um. Uh, this happened, um, with a peer of mine who was also a director. Uh, this is now I'm in a different organization. I'm in Palo Alto with HP, and this person had sold the company for 500 million or so before they had come to HP, so they had a spectacular sparkling like exit success story behind them. Um, I delivered that feedback

them

They, they took a senior director level role, um, you know, the startup was probably 10 years ago, um, but they had like they had, um, done a lot of other assorted things before they got to the point where, you know, this kind of. Senior director role for them showed up. So I was,

yeah, it's, um, uh, it was an interesting decision. It also made it a little more challenging for me because I just finished my one year kind of business school thing and joined as a director, and I was like, well, this person clearly has a lot more experience than me. So, um, when I had to deliver this negative feedback after the team members that I hired saying, you know, you gotta talk to Chris, you know, he's sort of telling us what we need to be doing in sales enablement, and he's giving us all these playbooks from his last company, and we don't know how to like tell him that he's telling us how to do our jobs even though his job is actually something different. He's not responsible for sales enablement we are, so that was the context of like, you know, the feedback that I had to give, um. It wasn't very pretty initially, Brandon. I actually tried to go the orthodox route, so I said, let's do a Rasi, who's responsible, who's accountable? And he was like, absolutely, let's do a resi. So we go through a Rai and I realized that um. He, he doesn't wanna actually talk openly about what's happening here, which is that he's taking on all the responsible parts of the things that, you know, me and my team are supposed to be responsible for, um, so after two failed attempts at doing a essay in my third conversation, I said, uh, I'd love to just catch up with you over lunch, went, had lunch with them, and then found a 15 minute window where I delivered that feedback without mentioning names. I said, look, I have some feedback from the team. Um, it's very hard for them to do what they need to do because they feel that, um, there's, you know, you're specifically giving them, you know, play by play advice on what to do, and I wanted to get your feedback on it. So I posed it kind of as a question based on the observation I shared, um, you know, he, uh, eventually came around to saying that that's exactly what he was doing. Uh, and then he paused, and so I, it was a little awkward for me because I thought he was gonna be like, well, I, I hear your point. I don't think I'm gonna do it again. But it felt to me that he, he felt that he had the right, you know, he had the right, uh, approach in telling my team what to do. Um, so I persisted, you know, at this time, you know, it's, it's time to order your coffee or dessert, right? The meal's about over. I'm like I need some closure here in this conversation. So what I recommended to him was I said, look, um, you know, I'm a little concerned that we're gonna lose some team members if they don't feel that sense of autonomy in the role that they're doing, and, you know, I welcome your feedback, but, you know, I would propose that we do like a 2 hour workshop where we can get all the issues out, uh, about how we're doing sales enablement, get your feedback as well. Would you be open to a workshop? And he said, uh, yeah, I'd be, I'd be very open to it, and, you know, then this took us in a, in a slightly different direction, um, but, um, let me know if you have any questions, just giving you, I,

I think given that they had not responded to the RSI, which I've never had trouble with doing a RSI in general with any, you know, anyone in an organization, I realized I had to take a slightly unorthodox approach where rather than just building a wall, I said, you know, if this person has good ideas, let me get that sense of participation, but with my team feeling like they're peers in the conversation, um, I thought they, they took it well by at least being open to the workshop and once we did the workshop, I gotta tell you. It became clear to me that a lot of this was about style, you know, this person, um, had a certain way in which they felt they had the right answer, but when they were in a workshop setting, I realized that actually they were way more collaborative than, you know, the team gave them credit for and maybe, you know, my team needed a little bit of coaching as well about, you know, how do you deal with the high powered like senior director who thought that they were like the CEOO, right? Um, but, uh, yeah, overall we, we got the, we got the results, um. Two weeks ago, I learned this person passed, by the way, you know, they were at a golf course and they had a cardiac arrest and they died and um I, I was just, you know, reminded that it's really hard to Kind of know why someone does what they do, but it's interesting you're mentioning about their background. I was like, well, I literally just learned that this colleague of mine is gone.

I think the big thing I learned out of that was that there are people you encounter where um they, you know, they like you have to show a stop sign in a certain way, otherwise they're basically gonna keep doing what they're doing because that's what they were doing in their startup life. It was only 7 years later or 8 years later when I was in my startup life that I started getting a little bit more empathy for saying, you know what, I can see why this person like was maybe not the right fit for. That role at the time, but um uh But it took me some empathy on actually having experienced startup life to be like, OK, you know, you gotta take ownership, and sometimes that can hit its limits in a larger organization. Yeah,