There’s a special place in hell for those who kick down and kiss up…

Perhaps given her background, or that we had discussed her radical candor framework in Touchy-Feely, or just how confident and charismatic she was, I felt an energy in the room and a connection to Kim Scott right away. As someone from outside the Valley, and the seeming “happy clappy” attitude to work here, I was already quite bought in to the idea of Radical Candor and the idea that we all go in to work for a purpose (and often a fiduciary duty) that extends beyond the easier and more immediate consideration of being liked and keeping everyone happy

A couple of ideas in Kim’s talk were quite striking to me, even beyond just the surface level exhortation to candor, and I’m still not fully clear on how to process some of these. I did try to come up with analogies or examples from the past or just some illustrations as she went along to kind of support or detract from the debate in my mind as she talked, but would be interested in broader perspectives:

1. “Obnoxious aggression” is a better strategy than “ruinous empathy” in a work relationship, if one cannot reach radical candor: I would like to believe this is true for the person being given the feedback (and the broader team), and looking back, I definitely have learned more from bosses or clients who have been aggressive rather than bosses who have been nice to the point of being essentially unable to manage a team efficiently (for example, teams that work all night or don’t actually get a project done because a manager was “too nice” to call out problems in time before they became REALLY BIG problems). I wonder though, if you were the individual in question, how it would serve you in the short and long term, and I wonder if there are illustrations of how it works out. The closest I can come to thinking of such cultures are firms that are almost known as “where not to go to work” and that have high turnover, and so while I would like to believe that directness is always the best path (preferably with, but else even without, “personal caring”), I question that it is true
2. I identified very strongly with the point on a special place in hell for those who “kiss up and kick down” and I think few things in life make me as angry as an in-authentically “nice” person. Given this, I also tend to be the person who will kick up perhaps more often than necessary, and felt a strong connection when she mentioned her story on calling out Larry Page’s supposed values misalignment. To me, it served as a good reminder to be a little more reined in even with radical candor, and a very good demonstration of having lost out on the “care personally” axis in her 2D approach

During Kim’s talk I was also reminded of an old manager (lets call her Sarah), on only my second project at work, who was extremely demanding of me. Part of the problem was that the manager on my first project (who was new at the time) had been easy-going and so I was not up to Sarah’s standards. She was exceedingly blunt about it, and would return work that was not up to her standards with a “re-do” and told me I was not a good enough problem solver and not committed enough to be at that firm. For the first couple of weeks, I was absolutely miserable, mortified every time Sarah gave me feedback, and mostly just wanted to quit. However, she would also sit down with me on a daily basis and try to get me to understand the right way and correct every “mistake” I’d made. I realized slowly that Sarah helped me become really good at the job. She was so blunt and so demanding that virtually every project after that felt easier, and I really learned to take critical feedback and manage my emotions while doing it. I also realized with time that Sarah always had my back: she did not care about being liked, but she did care about doing the right thing, being transparent and being very fair, which to her meant doing the best possible work for our clients and challenging her team to the maximum, being critical in person but making her people look good when they were not in the room. She became one of my closest confidantes and mentors, and now she’s one of the first people I see whenever I am back in New York

I personally feel that Sarah’s way is the right way (and I emailed her right after class to let her know I was thinking of her in the context of radical candor and that I missed working with her). I saw, not right away, but soon enough, how much she actually cared for the things that mattered. I also know she had a very loyal contingent of colleagues at work, and the people who took the time to know her absolutely adored her. I do wonder though what would have happened if I had not been somewhat persistent in trying to work through Sarah’s challenges. This makes me wonder whether starting off gentler and then getting to direct challenge is a better strategy, but it is also perhaps a more “disingenuous” strategy. And so I guess I don’t know the answer, perhaps it is understanding how much the person in question can take of a direct challenge? I’d love to know how others feel on this.