A while back I wrote about how to have 1:1s with your individual contributors, but today I want to talk about how to have 1:1s with your boss. Back when you were an individual contributor, 1:1s would have been pretty simple. Your boss asks you about wins, blockers, professional development, you answer, you get some feedback, and then you bring up any other things you wanted to cover. As a manager, things change.

Focus on pushing information

You’re the manager. Your boss is a manager of managers, and thinking longer term, bigger picture, and not as deeply in the weeds on those day-to-day bread-and-butter tasks your team is dealing with. It’s entirely possible that they don’t know what the most valuable information you can give them is. So unlike an individual contributor 1:1 meeting, you have to take the lead and relay the most important information to your boss.

How the team is driving value

Since your last 1:1, what activities have happened on your team that relate to driving new revenue or improving customer retention? For the curation department, we can contribute to new revenue through new features and datasets that could appeal to new companies or new teams within companies that are already customers.

To improve customer retention, the easiest things we can do are to improve data quality or improve the speed at which updates get to users.

A more complicated way to retain customers involves working across PODs. In those cases, we provide our expertise with the data or how we anticipate users would want to interact with the data, to developers working on the interface to suggest additional ways to add functionality on top of the data we already have. Ideally this work also comes with customer validation, but that’s for a future post.

Initiatives you and the team are driving

Once your objectives are set for the quarter, it’s important to keep senior leadership updated on how your team is working towards those objectives. What tasks are your team working on to move towards the objective? What do those tasks build up to, or what are the milestones along the way to achieve the objective? Once the rough skeleton of the work to be done is known, push more updates to senior leadership to make sure you haven’t drifted away from the shared understanding of what the objective is, or that you haven’t accidentally increased the scope of the work unreasonably beyond what was originally agreed upon.

For example, I missed a good portion of the most recent quarterly planning, because I was away for 2 weeks getting married. When I came back, I worked with my team to get caught up on what I missed, what the objectives were, and what tasks we were doing in the next 2 weeks to move towards the objective. In my exhaustion and lack of context, I was struggling to see how the initial tasks in the quarter would build up to achieving our objective. So we got our POD together and planned out a few milestones along the path from the start of the quarter to achieving our objective. In my next 1:1 with my boss, I relayed the fact that we had planned milestones and that I could keep him updated on our progress towards the objective, in relation to the milestones, week to week. This way we would be able to quickly determine if we were drifting off course or that we had changed the scope of work.

Now not every initiative your team is driving contribute directly to increased revenue and customer retention. There can also be work to improve team morale and culture, like feedback week, improving processes, onboarding, etc.

Advocate for your team

Highlight people on your team

Every chance I get, I try to update my boss on some of the impressive things my team has done. One person is learning software development in their spare time, one person is learning product management, one person is an expert on processes and went from not knowing how to code, to vibe coding a spreadsheet that tracks all of our teams metrics. I keep my boss updated on these things.

I want our team’s value to be visible beyond what’s written in their job descriptions. Because we put such a strong emphasis on professional development, we’re all completely different employees today than we were 6 months ago. Our job descriptions were written even further back than that. By highlighting what my team is doing, it’s easier to advocate for more professional development opportunities. It’s easier to approve an expense for someone taking a course, which could lead to a raise or title change.

For something like learning to code, there’s typically a big up front investment of time and effort before someone is effective enough to start actually contributing to software development or where it’s worth the opportunity cost of another developer mentoring them. If I can highlight what they’re learning or what they’ve created, it’s a lot easier to justify a little bit of developer time to push their skills to the next level.

Raise concerns about performance issues

If you ever have concerns about someone’s performance, the 1:1 is the place to bring it up with your boss. But you should also consider earlier signals. Maybe there’s someone on your team where you just don’t have a good vibe with. Now, I’m not saying that’s enough of a reason to let someone go, but it is a signal you should listen to. In a 1:1 with your boss, you could bring up this feeling early, and challenge it together. Maybe it does speak to a performance issue, maybe a communication issue, or maybe it’s just a difference in style. Either way, the 1:1 with your boss is a great place to bounce ideas off of someone to get to the root of a potential issue.

I know in my case, I’ve left that feeling linger for too long, and it’s lead to some complicated situations down the line.

Coordinate cross-team resources

Aside from larger meetings with the product leaders at the company, or individual chats with other POD leaders, talking with your boss is also a great way to coordinate cross-team resources. Individually, the POD leaders are very agreeable and will accommodate a lot of my requests for resources. In product leadership meetings, we can connect the resource requests back to overall strategy. But when I talk to my boss about cross-team resources in a 1:1, we can connect the request to strategy and decide if it makes sense long before I commit to making the request publicly with the rest of product leadership. It’s very similar to what I said about Active Commitment and getting practice committing to a course of action in a safe environment.

Team goals

Eventually, I want everyone on my team to be a master at using AI tools. We’ve already learned so much and accelerated a lot of processes through the addition of AI for some very simple tasks. My boss is aware of this, but I also want to keep pressing the point that we’re investing in building skills in this area for the long term. By keeping it top of mind, I can continue to push for more advancement opportunities for individuals. A rising tide lifts all boats, so by advancing individual and team goals, I can also raise the bar for the whole team in terms of opportunities and compensation over the long term.

Don’t forget to advocate for yourself

Every now and then I’ll tuck in some advocacy for myself at the end of a 1:1. Now if I can be a little bit mercenary for a minute, one of the goals I’m working on for myself is to move from the title of Manager to Senior Manager and eventually Director. So based on the sorts of updates I push to my boss in 1:1s, I ask for feedback around what kind of outcomes they would like to see from me to show that I’m ready for that transition.

With any title change, it also depends on the organizational need, budget, and a number of other factors. But focusing on what I can control, I want to get feedback on whether or not I’m ready, not necessarily whether or not the rest of the stars have aligned. As long as I know that I’m on track, I can keep learning and growing without worrying about wasted effort on misaligned goals.

Wrapping up

In 1:1s with your boss, you want to take the lead to push information to them, rather than having them pull information out of you. Focus on how your team is driving value for the business, the initiatives that are being pushed forward, advocate for your team (highlight contributions, and raise concerns), talk about the direction of the team long term, and don’t forget to get feedback for yourself to get yourself ready for the next steps of your career.