The Good Stuff & the Hard Stuff About People Management
Managing for the first time is exciting…and terrifying. So if you’re wondering what to expect from leading a team, this post is for you.
Below is ‘the good stuff’ and ‘the hard stuff’, as I see it, about management. This originally was a Google Doc for first-time people leaders on my team, and it’s not all rainbows. I wanted to be honest about what the highs and lows have been for me, and what I wish I had known when I started managing people for the first time.
My hope is that this can help new managers put things in perspective as they happen, and navigate the weird, yet wonderful, world that is management.
The Good Stuff
1. Being a Conductor
Great managers are like orchestra conductors. Talented musicians make beautiful music as individuals, and even have solid jam sessions together, but when a good conductor brings them together, magic happens. In other words, the sum is greater than its parts. As a manager, there are moments every now and then when you stop and appreciate how uniquely talented your direct reports are, and it motivates you to help them drive even greater impact together by providing the right tune (mission, vision, guardrails, context, support, etc.) It’s hard but when it works, it’s incredibly rewarding to see your team drive meaningful impact, and even surprise themselves with what they’re capable of. It personally makes me excited to invest energy into things like vision-setting, kick-offs, quarterly kick-offs, priority memos, etc. because I see it as part of becoming a stronger conductor. I like that challenge.
2. Sweating the Small Stuff Less
I always assumed that managers had way more to worry about than individual contributors in a way that was unsustainable. As an individual contributor, I was always going at 100 MPH, pushing myself, working early and late, etc. and I remember thinking: How could I possibly do this well while also managing a team? And after about two years of managing at HubSpot, it hit me that the big stuff had become small stuff. It was taking up less space in my brain and bandwidth. For example, every now and then when I have 1:1s with my manager, I ask her for help on something I’m all worked up about or feel is really high-priority. She’ll calmly help me navigate it and make it seem very manageable. I love those moments because it puts things in perspective. As a C-level exec, her definition of a problem is different from mine as a Director. And my definition is different from that of my team. So if you’re worried about being able to manage it all, just know that over time, your perspective will shift for the better. Jeff Bezos said something in an article the other day that stuck with me: “None of the people who report to me should really be focused on the current quarter.” As a leader, you actually can’t afford to sweat the small stuff; that comforts me and helps me stay balanced.
3. Helping People Find Their “Thing”
A big part of managing is helping people unlock their potential. It sounds really corny and I don’t like the lack of humility around the idea that I’m meant to ‘help people be their best selves’ because I do believe that’s up to the individual. That said, it’s on us as managers to help people go from good to great, or great to excellent. The thing is, everyone is so different. Each of your direct reports will be completely unique in what gets them fired up, how they like feedback, what work makes them light up, what they procrastinate about, etc. It’s incredibly rewarding to put energy into adapting your style and really listening to, and intuiting, what people need to be successful and happy, and then seeing them become successful and happy. They’re in the driver’s seat and their hard work is what gets them there, but a great manager will open doors for them, spot opportunities they didn’t know they wanted, and help them hit their stride.
4. Cultivating a Team Culture
Every team has its own micro-culture, and you’re on the hook for shaping it and finding your team’s rhythm. I love that our team has its own little quirks, rituals, inside jokes, etc. and how different everyone is. Do I get imposter syndrome every 10 minutes that other teams are having more fun, that I’m too tough, that we should’ve made mood boards together, that I don’t do enough team events or ask enough fun questions in Slack, that I don’t send enough gifts or cards? Absolutely. But imposter syndrome is normal. One of my favorite parts about managing my team is that there is no other team like ours; everyone brings some unique flavor to the mix and as a manager, you’re responsible for making all the ingredients work together so that everyone feels included, engaged, valued, and heard. I like the creativity that goes into that and it keeps me up at night (in a good way).
5. Trying to Be the Manager You Wish You’d Had
Think about all the bad managers you ever had, and the things about their management style you didn’t like. Then don’t do those things. Some of the best advice I ever got was to learn from managers who I admire, as well as ones I don’t. I actually find it easier to focus on who I don’t want to be as a manager, than who I do. I oddly love the motivation that comes from that because it gives me specific things to work toward as I grow.
The Hard Stuff
1. Finding Time to Do Your Own Work and Think
I want to be available, accessible, and quick for my direct reports; I feel terrible when I can’t review something thoughtfully for 3 days because I know it bottlenecks people and makes it feel like that thing isn’t important. Often times, that means everything I need to do personally gets moved down the list, or interrupted to jump in and help, brainstorm, or review on Slack. This is why delegating is so important and something I’m working on, as is being ruthless about your calendar. If it’s not important, delete it or skip it. If it drains you to do all your 1–1s in one day, split them up, etc. You need to be ruthless with your time otherwise you’ll never get to focus on the bigger picture work that will actually help your team progress.
2. Doing Manager Logistics
The more direct reports you have, the more “stuff” there is to do. Expense reports, approvals, manager trainings, performance reviews, knowledge management, etc. It adds up, especially when it feels like an extracurricular thing taking you away from your core day-to-day. My advice is to go into management with the expectation that you’ll spend several hours a month on these things — if not more depending on the season. That way, when it pops up or you go down a rabbit hole on operations that you didn’t expect, you take it in stride (somewhat!)
3. Feeling Lonely
In the spirit of transparency and candor, management is lonely. I often feel like I’m on an island. You want to be the “cool mom” and part of the squad, but there’s always an invisible divide that separates manager from team. You’re the “boss” at the end of the day and naturally that can make you feel siloed. Not to mention, over the past 2 years, the role of manager has completely changed: we’ve needed to put our own emotions or burnout to the side so that we can create space and support for our teams. I’m not going to lie — it’s really hard and you’re going to feel like the world is on your shoulders sometimes. My advice here is to listen to yourself when you need a break, and to lean into other managers. I guarantee you, all managers feel this way and talking about it really helps, and no one ever judges anyone for feeling frustrated or needing help.
4. Managing Low Performance
The hardest part of managing is managing underperformance. Because there is no good or easy option; you can’t ignore it and accept mediocrity, but you also care about your directs as people and don’t want to have hard conversations. I will say, it gets easier with time. The first time I had to performance manage someone, it was the darkest 6 months at work for me ever — it was what I thought about when I woke up and when I went to bed. Then after that, it got a bit ‘better’, in the sense that I got more comfortable remembering it’s my job to give someone tough feedback, and potentially make a tough call, if they’re not making HubSpot or our team better. You need to do everything you can to help them get there and be fair and clear about expectations, but it’s your job as a manager to address underperformance head on. Remember, it’s not serving them if you ignore it either — that won’t help them grow. So remember to give yourself some grace, and to not blame yourself — every single manager ever has had to go through this. So, let’s help each other and be there for support, encouragement, pep talks, etc.
Our CEO Yamini Rangan says that “leadership is like a mountain without a top.” We will never be ‘finished’ figuring out management. This is a reflection of my experience to date, but I have many mistakes, hard lessons, and joys ahead of me. As do you. My advice is to get comfortable with being uncomfortable, lean on other managers, and most importantly, be kind to yourself. You can’t take care of a team if you aren’t taking care of you.
Lastly, you got this.
