Human Skills 008 - Helping New Managers
with Kyle Jaster
How does someone decide to go and study how to be a better manager? For Kyle Jaster, COO of Harvie, it happened because he had gotten into management for what he describes as ego purposes, and then discovered that he was a very bad manager. That realization led him to a path of deliberate study and practice, reading everything from books on management to biographies, and working with a variety of mentors.
This interview was so full of good stuff I struggled to pull out a single theme to focus on for the newsletter, but in the end I chose his recommendations for new managers. Great concrete tactics, a solid starter template, and a mindset shift that has already changed the way I think about my work.
If you have time, you should really watch/listen to the whole interview because there's so much more there, but if not enjoy the advice below for new managers.
What do you teach new managers?
I've managed 20 or 30 people directly who have built their own teams. I've done a lot, especially with Harvie, where we have a lot of people who are kind of like coming from a warehouse context or where they're really going from zero to "I have to manage people". We've built kind of a pretty solid setup for them. And there's a couple main components.
The first one is that, I think the foundation of any good manager-manager relationship is trust, and that you basically cannot get anything done until you are starting to build trust with one another. And so that means having a shared vocabulary, figuring out what that is.
I think a really important thing early on is to understand why somebody is working here and where they wanna be. So doing that explicitly, just like saying, "hey, I'm your new manager. I wanna understand like, what do you like about this job? What do you wanna get out of it? And how can I be helpful to you in your long-term career, whether you're here or somewhere else?"
Write that down. Somewhere, put a note, so that anytime you're talking to somebody who you're managing, if you remember this person wants to run their own business someday, or this person really is here because they want clarity of their role, and they want to be able to work from nine to five exactly, and they want to do a very good job at that, and that's it. Whatever it is that motivates them or gets them up in the morning, you want to be able to speak to that when you're asking things of them. I think that's really important and really makes life a lot easier and costs nothing to do.
I think 360 feedback, making sure that you're not waiting six months to learn how people are thinking about their job and also they're not waiting six months to learn about how you're thinking about their job is really important. So everywhere that I've ever done coaching with clients or in companies that I've run or departments that I've run, we always have a 360 component of a one-on-one.
So, what am I doing well? For me now, what I ask is, "what do you like about what I've been doing lately? And what do you wish I was doing differently?" And I'll answer that for you and you answer it for me. And in that way you always have that kind of feedback between one another.
But if you have those three things... and then you have clear goals and clear areas of responsibility. And clear goals means like you want to achieve X by X date, it's measurable, right? Not like "you're doing a good job" is not a clear goal. "You have achieved this thing" is a clear goal.
Once you have a clear goal and the responsibilities, what are they actually responsible for, what do they not have to be responsible for. That's really the other kind of key component. But if you have those five things, you're in really good shape.
What do you see new managers struggling with?
Setting clear goals can be really difficult. It's difficult to set a key result at any level of a company, but especially if you haven't had practice with it, I think people really struggle with that. And so one thing that we've done that helps is set, in onboarding for standardized rules set a "hey in your first week you should have achieved X, by your third week you should have achieved Y, by your sixth week you should achieve Z" and if you have those things that helps a new manager set up "Oh, right, we can check in on these goals" and while they're doing that they can start figuring out what's the goal they want this person to do as they're coming into the role. That's helpful.
Areas of responsibility, I think HR has to really help a new manager on a lot of that stuff for it to be well done. It's more important for a new manager to be able to explain it well than to come up with it.
As a new manager, one thing to keep in mind is, your job has completely changed and you're probably going to feel a bit lost and that's normal. A lot of people who do a great job as an individual contributor, when they take on a management role, they're suddenly in a place where if they're doing the work, they're failing. They need to be handing that work to somebody and then helping them understand it and that is I think deeply uncomfortable. Particularly for the kind of type-a people who tend to end up being managers, they struggle with that. There's definitely feeling a sense of like being lost or not knowing what it is that the work entails when you don't have a work product at the end of the day can be hard.
One way that we try to help people combat that, or that I've tried to help people combat that, is to say kind of like, "what are the three things that you need to do this week that make you a good manager?" And it can't be a hundred item list anymore, it's gotta be two or three things that you're really gonna get done. So that's kind of helpful, in your one-on-one with a new manager or as a new manager prepping for your one-on-one, saying, okay, what's really going to move the needle for me this week?
Are there any key mindset changes you share with new managers?
There's an emotional experience that I've seen. I saw it in myself and I've seen it in a lot of people and I especially see it in new managers. I'll describe what happened to me and what made me have this realization.
When I was working at Noodle, I was having these massive mood swings in the course of a day. I was like, "oh my gosh, I've got everything figured out, I'm the best." And then I was like, "I know nothing and I'm useless and I suck."
And there was a period where it was happening in one week and then it just got to the point and you see it where it's like every day, every hour, I don't know what the hell is going on. And I was thinking about this a lot. Like it was like really fucking me. And I was thinking about my life on the x-axis and how my emotional experience was shooting up and then dropping down and shooting up and dropping down and shooting up and dropping down. It's like this crazy sine wave.
And at some point, I was thinking about it and I realized that the problem was the way I was looking at this was that I was looking at it from outside of the experience, and saying just measuring the emotional experience, and not what I was looking at that gave me the emotional experience.
And so suddenly I realized that actually what was happening was I'm climbing a mountain of knowledge. I'm learning all of these things, and when I feel like I'm at the bottom of something, it's because I'm looking up at the mountain of knowledge I have to climb to get to the next thing I want to get to. And when I feel awesome, it's because I'm looking down at the mountain of knowledge I've just acquired to get to somewhere.
And so the thing that I talk about with a lot of people on my team is like, when you're having that emotional change, it's like, "Are we looking up the mountain or are we looking down the mountain right now?"
Nothing has changed within the day that should make you either amazing or terrible. It's just which direction are you looking. For me it helped me become like, "oh, when I feel bad, it's because I actually just learned what I need to do next." And that's the next piece that I need to climb. And that became very motivating for me, whereas before I was just feeling really kind of lost at the same time.
Recommended Resources
Note: These recommendations are straight from Kyle in his voice
Favorite books for new managers
How to Win Friends & Influence People (Dale Carnegie Books). - Everyone thinks this book is about manipulating people. It isn't. You already know everything in this book, but it gives you techniques for understanding and doing the right thing as you develop new relationships.
The Checklist Manifesto - This book explains in great detail how simplifying processes results in better outcomes. I think about it whenever something is getting complicated.
For someone starting to scale up a team
Measure What Matters or Traction - Both are good models for setting and tracking goals with a team, and helpful in thinking through how to organize collective effort.
Scaling Up Excellence - Concrete examples and actionable ideas on how to manage growth, with a focus on culture.