Before It’s Too Late
The When, Why, and How of Impactful Colleague 1:1s
One-on-one meetings (1:1s) are pretty common in the corporate world. And for 1:1s with colleagues (neither your manager, nor your direct report), I think Product folks can accomplish a lot with little effort, by using the right strategy. Unlike manager-employee 1:1s, these meetings offer unique opportunities for cross-functional collaboration, knowledge sharing, and network building within the organization.
During my years in Product at both a Fortune-100 company as well as startups, I’ve had a full spectrum of experiences in this regard — from wondering how to tactfully put an end to recurring 1:1s that were unproductive, to wishing I’d done a 1:1 with a colleague months earlier.
As always, the right thing for you to do will depend on your context. But in general, I’ve found that the rule of thumb for successful 1:1s is this:
Early, not often.
The When
I always try to get a 1:1 scheduled with everyone I’ll be working with in my role, as early as possible. If I’m joining a new team, my first order of business is to compile a running list of colleagues I need to meet and kick off a working relationship with. At some point in the first couple weeks, I’ll aim to find 20 minutes on the calendar to meet with each of them — my immediate partners (engineers, designers, etc.), my peers in Product, and any other partners and stakeholders I think I’m likely to be working with on any frequency.
When someone new joins the company or moves to a team that I work with regularly, I aim to do the same with them.
And for the majority of my colleagues, that first 1:1 may be our last. My default is to not set up recurring 1:1s, except in cases where it’s obviously productive. This typically includes 1–2 key partners from each function — folks who I will be collaborating with often. This may be a lead/principal engineer or engineering manager, a designer or design lead/manager, my Product peer from any other team whose work needs to stay in sync with mine, etc.
For everyone else, I won’t set up a recurring 1:1, unless I find some compelling cause to make it a regular thing. But I will absolutely meet with them once, as soon after I/they join the team as is practical.
There is a ton of value in an initial 1:1 with any partner or stakeholder, and the sooner the better — as I’ll explain later. But it’s much better to add an ad hoc meeting to the calendar when there’s something important to discuss, than to keep a recurring session on the calendar just in case. Just-in-case standing meetings often become mostly wasted time. That’s true for almost all colleagues, except for those that are the most critical partners for my product or area.
The Why
In general, the first 1:1 breaks the ice. When you need to contact them to ask a question or see them in a meeting, it won’t be awkward, because you’re already acquainted. It’s never easier to break the ice than the first couple weeks that one of you is in your role. And it’s also the perfect time to set the tone for the relationship.
My goals for the first 1:1 with each colleague are these:
Make sure they know that I'm not a jerk and am here to help
Make sure they'll feel safe collaborating with me
Make sure that our first 1:1 conversation isn't when some issue or conflict arises — so we'll have some relational capital to help when it does
For the last of those goals to resonate, you need to keep in mind that hard situations at work will inevitably come, tensions will inevitably rise, and there will eventually be some form of conflict with someone(s).
If you’ve never really had 1:1 time with someone during peacetime, it’s hard to try to build a functional relationship with someone on the fly, once you’re facing wartime. So, the last thing I want is for our first 1:1 conversation to be me needing to inform them of some crisis or apologize for a mistake I’ve made. That’s a hard way to introduce yourself!
1:1s don’t need to feel “productive” to be a great investment of your work time. I think Stephen Covey was the first to advise that when it comes to people, slow is fast, and fast is slow. This is so true and so important — in all areas of life.
Relationships outside of work help to illustrate the validity of this advice. If I only talk to my kids when there is family or household business to discuss, it’s going to be painful every time I tell them they need to get to bed or turn off the TV. I have to build and maintain a healthy relationship with them interpersonally, if I want to earn the right to bring them news they don’t like. Otherwise, I’ll be seen as the annoying stranger who does nothing but break up the fun!
And the same is true for someone I work with: if the only time they hear from me is when I tell them we have a problem or an urgent deadline, I’ll feel to them like a harmful intruder in their life — but if we have good will built up already, they’ll feel like we are on the same team, facing a shared challenge.
The How
During my initial 1:1 with each new colleague, I do general get-to-know-you stuff, like asking how long they've been at the company, on the team, etc. I’ll ask about what they do for fun, where they grew up, or whatever else happens to come up. It’s useful for our working relationship to build a personal rapport in this way, and there’s always a chance of finding a genuine friend at work.
I met two of my best friends in my initial 1:1 with each of them, when I joined their team, and we’ve remained close for years after we stopped working together — so there’s always some possibility that the new connection goes beyond just fostering an effective working relationship.
During the initial 1:1, I also focus on level-setting on the following points, to prepare us for an effective working relationship:
Valuing Their Expertise: I acknowledge their unique skills and expertise, emphasizing my appreciation for their input. This is tailored to their role, highlighting that I welcome thoughts and feedback on a broad range of topics, even those outside their typical scope. This is particularly relevant when engaging with engineers and designers.
Encouraging Open Feedback: I stress the importance of their feedback in shaping my work. Quick and direct feedback is crucial for me to learn and adapt. I assure them that all feedback is welcomed and will be received positively.
Gathering Contextual Insights: Understanding the broader context of the product and team is invaluable. I ask for any insights into the organization's culture and ways of working, to help me integrate effectively and discern how I can best be effective in this context.
Supporting Their Role and the Team: I inquire about how I can best support them and the team, especially from their perspective. This is an opportunity for forward-looking collaboration, particularly if I'm new to the team or if they are joining my existing team.
Cross-Functional Product Insight: For designers and engineers, I clarify my role in decision-making on the Product side. While I may make the final calls, collaboration and collective input are key. I explain why I’ll rarely use the term "requirements"; instead, I’ll focus on collaboratively determining the best project scope and shape of features. My approach involves valuing their input and being open to discussions — even pushback — on project plans, to ensure that we collectively build the best product we can.
If you want to keep some cadence of 1:1s with colleagues who are not critical to stay close with for work you’re collaborating on, Donut bot for Slack and MS Teams (or any way to accomplish the same effect) is nice for setting up less frequent 1:1s with team members or folks from the broader org, to give the less-work-focused face time with various folks. Donut allows you to schedule a single 1:1 each week, and it will handle pairing you up with one of the colleagues who have opted in. Rather than a weekly or monthly recurring meeting with each person, you’ll be matched with one person each week — which is a much more manageable time commitment (though you can opt out on any given week) and still gives a chance for some time to meet colleagues and socialize. I’ve found it especially useful in a remote-work environment, where there’s no opportunity to bump into coworkers in the kitchen or as you pass their desk on your way back from lunch.
Impactful 1:1s with Partners & Stakeholders
I think people enjoy working with folks they feel like they know and have a decent relationship with (not full-on friends in all cases, but friendly and acquainted). When it comes to non-manager 1:1s, a little goes a long way, and the earlier the better: early, not often. Get off on the right foot, set the right tone for the relationship, and be ready for whatever comes up in the future.
I’ve shared my own list of goals and points I want to communicate to my colleagues early on, but it may not be the right fit for you. What goals do you have for your first 1:1 with colleagues?
Whatever they are, accomplish them early, and you’ll be glad you did.