The Missing One-on-One

Many new managers define 1:1 meetings as something like “a regular opportunity for a manager and their direct report to check in.” That’s a fine starting point but it misses out on a significant learning opportunity for leaders of all skill levels: the peer one-on-one.

Used effectively, these conversations can be a catalyst of growth for you and your organization.

What is it and why does it matter?

Let’s start with a totally incomplete list of what an effective manager covers in a typical 1:1

  • Challenges and how to get past them
  • Giving and receiving feedback
  • Expectation setting
  • Strategic planning beyond the day-to-day
  • Career growth

When you’re still a full-time maker, limiting these conversations to you and your manager is very effective. Your manager has a high degree of impact on your challenges and context on your work.

This degrades as your scope grows within your organization. Your manager’s context decreases as they delegate more and more to you. The onus for solutions falls increasingly on your shoulders just as your key ally is less able to help.

If this sounds familiar, you need a peer one-on-one. These are periodic checkins with the closest person you have to a peer. In a large organization that might be an actual organizational peer. In a smaller organizations that might be a senior engineer on another team, a manager in another department, or a management coach.

“What Do I Talk About?”

This is easily the most common question when I suggest these checkins. The answer might seem counterintuitive, but it’s the exact same list of topics I outlined for “normal” one-on-one meetings.

While your peer might not have the same context and assistance that your manager can provide, there’s a few other benefits that your manager can’t provide so easily.

The biggest is that these meetings can be a safe space for a variety of topics you may not feel comfortable bringing to even the most supportive managers. This might include getting feedback on half-baked ideas or asking “how would you solve this” questions of your peer. If you share the same manager, these peers can be an invaluable asset in helping you understand your manager and “manage up” to them.

Peer one-on-ones have also addressed one of my biggest challenges of leadership: finding safe opportunities to vent. Leadership can be a lonely and isolating job - it’s inappropriate to vent to your direct reports and it can be dangerous to vent too much to your own manager. This leads to keeping your frustrations and challenges bottled up. This allows them to build over time into major problems for you and your team. Peer one-on-ones create the space to talk about these frustrations with someone who understands (and perhaps even shares them.)

Your first one-on-one

Starting these checkins can be intimidating - you have to make yourself vulnerable to a coworker in a way which feels like asking someone out on that first date. Just like that though, the best way to ask someone is just to ask them.

Until you’ve had enough of these meetings to find your rhythm, it can feel a little awkward at first. Push through that - learning to be vulnerable as a leader is a huge skill that pays dividends over the long-term.

Just like all one-on-one meetings, the cadence and structure will vary as you find what works. Having these conversations offsite can help reinforce the idea of a safe space separate from work, but find what works for you.

An example

When I moved into director-level management at Braintree, I did so with one other person, Pedro. We started these checkins out of necessity as we each went through the journey of figuring out what our jobs actually were.

Pedro and I kept these meetings long past the point where we understood our new roles. They became opportunities to get feedback on our plans, discuss performance issues in our organization, and sanity check reactions from our teams or stakeholders. Without intending it, these meetings were catalysts for each of us.

It also had other unexpected benefits. When a crisis came up in Pedro’s organization while he was on paternity leave and his manager out, I had the context from these conversations to drop everything and cover for him for a week. This would have been a rough transition for all involved if we hadn’t been spending an hour every other week comparing notes.

These checkins aren’t just for peers in the traditional sense as well. I’m a huge fan of these 1:1’s with my product partners as well. At Reverb, these checkins helped Engineering & Product stay aligned and keep our people unified as one product delivery team.

Get started!

I hope this has convinced you to start these checkins of your own. If you have any questions or concerns about finding the right partner or starting these conversations, let me know in the comments below. If you have additional tips or insights from these checkins, I’d love to hear about that as well!

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