I've managed quite a few teams at this point ranging from interns to other executives. I've found that periodic 1:1s (one-on-ones) are a helpful habit for:

Building effective relationships
Candid feedback and helping people grow
Keeping a pulse on the organization

What are 1:1s?

For the context of this blog post, 1:1s are a time for you and your manager (or you and your direct report) to meet one-on-one to discuss work, career, and life. They are a time for you to ask questions, get feedback, and discuss your goals. They are a time for you and your manager to get to know each other, understand your work, and help you grow.

Benefits of 1:1s

Candor and Trust

One of the best benefits of having 1:1s is developing candor with your directs. Once you achieve this, you can really see what's on their mind and what concerns them. They're also more likely to share earlier ideas that might not be fully formed and ready for a broader group.

Big picture questions in 1:1s can be simple curiosity or early tells that something else is amiss. If someone on your team is asking about the company's mission or why a project is a priority, before answering, I'd suggest asking them what they think is the answer and then fill in the gaps.

Keep in mind that whenever one person has a question about the project/team/company, it's likely that others on the team have the same question or similar doubts. As I go through my 1:1s, I take private notes as well to see if there are any themes that should be addressed at the next all hands meeting.

Some questions that have been asked in 1:1s:

Why are we working on XYZ and not working on ABC now?
What is the company's mission?
What is the team's mission?
How am I doing in my role?
What are the next steps for my career?
I feel like I'm not excited about my job. What should I do?
I used to be really interested in Foo, but I haven't been doing it lately. What should I do?
What are you (my manager) working on?

Some of these questions also yield an opportunity to make sure thoughts are clearly written somewhere so they can be shared more broadly. If there's an existing artifact (e.g. Value Prop, Mission Statement, Spec), review it/update it and share it with your direct. If there isn't an existing document, create one (or ask if they'd like to create one) and include the thoughts discussed in the 1:1. Notion, Coda, & Google Docs are all great places for longer-form content like this to live. Then you can draw attention to it via an All Hands or sharing a link via Slack/Discord/email.

Pairing

Pairing is where you spend time with your direct to help them do a specific task. Pair-programming, reviewing a PR, coauthoring a spec, putting together a model in a spreadsheet are all examples of hands-on pairing.

Sometimes people just need to talk through a problem. But I've found that pairing is a great way to get in touch with the current challenge someone is facing.

I firmly believe that managers should periodically walk a mile in the shoes of their directs. Sometimes there is friction in getting started that you weren't aware of. This could result in investments in tooling, documentation, content templates, process improvements, training, or just provisioning access to something that already exists.

Sometimes there's a skills gap. I have helped countless PMs, engineers, and analysts extract insights via SQL.

Soliciting feedback for yourself

1:1s are a great time to get feedback about how you could be a better manager. I would encourage you to ask your directs questions like the following:

How can I be a better manager?
What else could help you succeed in this role?
Are there any blockers that I can help remove?
Is there anything I've done or said in recently that seemed questionable? Confusing? Incorrect?

Practical tips for 1:1s

First 1:1s

For your first few 1:1s with someone, you should try to understand what motivates (and demotivates) them. As a manager, you can use this to help steer projects their way that align to their broader interests. I like to ask the following questions:

What are you most/least excited about in your role?
If you look back in 1 year, what would you want to have learned/accomplished? (How about 3 years? 5 years?)
What are your biggest concerns in your role?
Outside of work, what do you find yourself gravitate toward? What gives you energy?
What do you see as the biggest opportunities for the company?
What are some of your concerns for the company?

Scheduling

Figure out a good time and frequency to meet and what the impact could be. I tend to schedule my 1:1s mid-week or later in the week. I've found that:

Meeting in the beginning of the week could help set the stage for what people should focus on that week. This is great when in an execution mode or ramping up a new team member. If there's already a weekly kickoff, the 1:1 can feel somewhat redundant or take people out of execution mode. Make sure the 1:1 is a complement, or schedule on a different day.
Meeting near the end of the week tends to give people time to reflect on bigger picture thoughts over the weekend.
If there's already a meeting heavy day, consider adding the 1:1 to that day. Batching meetings back-to-back can really help free up other contiguous blocks of time on other days for focus time. The downside of this is that the feedback given in a 1:1 could be drowned out by the flurry of activity from the rest of the day.

Tools

All you really need is a shared document that you can both see and contribute to during and outside the meeting (Notion / Google Docs works just fine). I put a blurb like this at the top of my docs to let my directs know that this is their meeting, and they should make the most of it:

Every 2 weeks, you will have 1 hour with me to discuss whatever you want to discuss 1-on-1. This meeting should be driven by you and not me. From time-to-time, I may have a high-priority topic that we will discuss first and I will always have topics as a backup if you do not have enough to fill the hour. For putting together the agenda, I'd suggest starting with high-level/open-ended discussions and to save any in-the-weeds discussions for afterwards. This meeting should almost never be canceled unless due to sickness/travel.

I also have a section called Hopper at the top where we can put topics that we want to discuss in the future. You can also move topics here that weren't covered from previous 1:1s, but are still relevant and should be revisited in a future 1:1.

In 2022, one of the members of my team suggested we use a tool called Range. I personally felt it was a bit heavy-handed for 1:1s, but it is an extremely useful tool to replace/augment the Daily Standup. Range does have some fun controls and content for doing ice-breakers if that doesn't come naturally to you.

Kickoff / Ice-breaker

A big part of work for me is enjoying time with people that I spend years of my life working with. So as part of that, I want to get to know them and have them get to know me. So I like to start each meeting by discussing something non-work related. It could be a hobby, an upcoming trip, something that happened over the weekend, a side project, something trending on Twitter, etc. This helps my directs and I to get to know each other better. Over time this builds a level of familiarity, trust, and transparency that makes working together more enjoyable and productive.

Review Agenda

After the ice-breaker, brainstorm topics together and write down specifically what you want to cover in the shared doc. This helps prioritize and structure the 1:1. Ideally we start with bigger picture questions and finish with clear action items.

In-person > Video > Audio

I've found that in-person 1:1s are the most effective for building bonds. I had one manager who did a walk-and-talk 1:1. I enjoyed our walks from the Presidio to the Wave Organ in San Francisco. The only downside was that it was difficult to take meaningful notes.

Video 1:1s are the next best thing because you can see facial expressions and provide/accept non-verbal cues like nodding or shaking your head to provide feedback with interrupting.

Downsides of 1:1

Usefulness decays over time

1:1s are more helpful for people who are newer to the role. If you are new to a team or to a new manager, 1:1s are helpful to get a lay of the land and to have a consistent place to ask any question.

If this is your first role (internship, straight out of college, brand new to an industry or function), weekly 1:1s can be very helpful to get you up to speed on what you should be delivering and on what cadence.

If you've been in a role for a while at the same company with the same manager, there is less value in weekly 1:1s and you should consider bi-weekly or monthly.

It's still a meeting

There are some downsides to 1:1s. They're still meetings, after all. If you go off on a tangent every 1:1 and don't talk about high value topics, it will become a routine that is loathed.

If they are in-person or conversation-focused, there needs to be time given for notes to be taken and action items to be accounted for.

They are not highly leveraged. The discussion in a 1:1 is inherently limited to 2 people unless someone distills conversation into a shareable artifact.

Frequently Asked Questions

How frequently should I have 1:1s?

If you have 5 or fewer direct reports, I've found that weekly or bi-weekly 1:1s for my directs are about the right frequency.

If somebody is new to a team, weekly 1:1s can be very helpful to unblock them as well as leverage their fresh eyes and see what they see before they're assimilated into your team's culture.

For any of my skip-level reports, meeting with them monthly seems to be about right. This gives me a sense to see how teammates in Client Success or Sales are feeling about the quality of the product, the team's velocity, and surface any concerns about their side of the business. If you're in a product role, often times meeting with someone from a different department will give you keen insights into what pain points exist and how they could be solved with a product improvements.

What if my manager doesn't want to have 1:1s?

Find out why. If they don't want to have 1:1s, it's likely because they don't see the value in them. If you can't convince them, then you'll have to find a way to get the mentorship/guidance/open forum you need from other sources.

Any additional resources?

Sample ice breaker questions: https://github.com/joelparkerhenderson/icebreaker-questions