After a small break, I'm starting a new mini-series of posts around one-on-one meetings. For a long time, I “free-styled” my one-on-ones without an agenda or structure before realizing that it’s not an optimal or effective use of anyone’s time. Being purposeful and intentional in one-on-one meetings has been a game changer for me, and I want to share a few ideas that have worked.
First off, I like to bucket one-on-one meetings in a few broad categories. Bucketing your one-on-ones allows you to use different colors on your calendar, prepare accordingly, and prioritize in situations where you're double-booked.
Upward
At larger tech companies, these are one-on-one meetings with people hierarchically above you. Most commonly, it's with your direct manager, but it could also be a skip-level with someone else in your chain of management. It could also be with senior leaders of adjacent cross-functional orgs. At a startup, it could be with the co-founder.
Lateral
These are with engineering manager peers in your org and those in cross-functional teams like product, design, marketing, etc.
Supporting
These are meetings with individuals on teams that you support directly and indirectly. One-on-ones with individuals that report to you directly may have a more operational angle than skip-level one-on-ones. As an engineering manager, this will probably be your largest bucket.
Over the next few posts, I plan on diving deeper into each of these buckets, starting today with —
Upward One-on-ones
Jumping straight to it, a few points you want to make sure you hit, and a couple of things you should steer clear when it comes to these.
Represent your team and yourself
When it comes to one-on-ones with your chain of management, the most significant difference between being an individual contributor vs. a manager is that managers represent their teams in addition to themselves. It's essential to make sure that both elements surface regularly in your upward one-on-ones.
You don't want to be spending all of your time discussing your team's work/culture/priorities and never get to how you are doing at your job (or the other way round).
Ask for strategic insights
Senior leaders have access to more strategic information than you do, and they're willing to share it! All you have to do is ask, and you'll be surprised how much information you can get. It's mutually beneficial, after all — the more you know how your work fits into the broader strategy, the more engaged you are.
This strategic insight that you glean can help you anticipate upcoming work, prepare for hiring, and ensure your teams have the right skills to deliver over longer time horizons.
Talk operational ideas
This one is more applicable to one-on-ones with your direct manager (but you can also use it with others). Bringing an immediate issue to get coached or getting into a discussion with your manager on the best approach to navigate a situation can be a great thing.
Not only do you get a different perspective on the matter, but it's also an excellent opportunity to get to know your manager's or co-founder's leadership philosophy and management style.
Receive feedback
Make sure you cover this at least once every couple of months. Most managers are in the habit of giving frequent feedback, and it's also ok to ask for feedback if you feel like it's been a while.
Feedback received from upward one-on-ones is some of the most valuable feedback you'll get, so it's essential to act on it and follow up.
Avoid desk-side chats
If it's something that you can stop by your manager's desk (pre-pandemic) and talk while in earshot of those sitting nearby or something that you can discuss in a Slack channel with > 5 people — it's desk-side chatter.
Examples of desk-side chats include specific discussions about technology, process, and delivery schedules. However, topics like personnel issues, hiring plans, or delivery risks are well-suited to bring up at a one-on-one.
It's suboptimal to spend higher-bandwidth one-on-one time for desk-side topics or, worse, status updates. Reserve your upward one-one-one time for speaking candidly about more profound issues.
What’s Next
The following posts will dive deeper into other kinds of one-on-ones, so stay tuned!