10 Non-Obvious Things I’ve Learned as a “People Manager”

I kind of like this format, so, I’m going to keep going.

  1. Repeating yourself can often feel patronizing and immature but I’ve discovered that a lot of that is just my own insecurity — most folks forget things just as often as I do and we all need a bit more repetition in our lives. Framing things can really help, especially if you’re worried that people will think you’re an asshole for it (trust me, they don’t… or at least not nearly as often as you think and believe).
  2. How you say things is just as important (if not more important) than what you say. This is infinitely harder in the context of a fully-distributed company which means you have to work even harder at it. This is why repetition often matters as you are effectively reiterating the same thing but from multiple angles and from different vantages so as to capture and align your message with the most people. If it’s impossible to do it adequately then you’ll have to get in-person or at least on video chat.
  3. Your staff care a lot about the why behind your decision making, a lot more than you may initially believe. Solving this tension requires a lot more time than you often want to give (or can dedicate time) to explaining the context, history, and reasons behind the why. But, this is the only scalable way of communicating the principles that underpin the very culture of leadership you’re trying to build, promote, and scale. And if you don’t model this, then, your newly-minted leaders won’t do it either.
  4. The quality of a 1-on-1 is less about what is actually talked about and more about how both parties feel by the time you leave the engagement. It’s vastly better to inspire folks to action (and leave a lot of the decision making in their hands) than to give them a list of things you want them to accomplish (as well as the “how”).
  5. The frequency of a 1-on-1 is less important than the quality of a 1-on-1. We all know what it’s like to have lifeless (yet scheduled!) meetings with folks where both parties are manufacturing enthusiasm, energy, and interest. This goes without saying, but, you should “do” 1-on-1’s the way you want — don’t blindly adopt someone else’s model without first considering your own style, personality, and general proclivities.
  6. There are elements about one’s management style that are irreconcilable with how a well-run organization typically operates (i.e. best practice). Consequently, you’ll have to willingly and intentionally change your own behavior for the sake of your team and business. If this sounds too much to ask, then, you shouldn’t be a people manager as there’s no excuse and no room for a tyrant.
  7. But… there are also elements about one’s management style that are unique and powerful and deeply personally and impactful — you should lean heavily into these characteristics and behaviors and own them fully. For instance, my favorite 1-on-1’s are where we are walking and talking. I try to do these as often as I can and it’s just part of my “style”. And, as far as I can tell, no one has historically had a problem with this specific managerial behavior.
  8. Telling someone that they should bring you “problems plus solutions” is one of the most arrogant things you can do as a leader because some of the hardest problems that the team has to solve do not actually have a solution to them (yet)! If you demand both, simultaneously, you’ll never have anyone voice a real, authentic, and serious concern! That’s your bad and your loss.
  9. Managers have a lot of “quick outs” and opportunities to “punt” decision making for later, saying stuff like “Let me think about that…” when we really don’t need more time. It’s dishonest to punt a decision when it’s entirely possible to make an informed (but incomplete) decision that’s more than good enough. Using this technique is really, really good by the way.
  10. Silence is an intentional decision that you make and it’s one of the most powerful tools in your managerial toolbox. It’s also dangerous if you don’t use it wisely or well as you can use it as a weapon to harm or enforce or to defend and advance your mission. Oftentimes, our silence is unintentional but interpreted as the opposite — it’s important that you clarify and, probably repeat yourself a lot (see #1).

This is fun.

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