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The big guide to One on Ones (1:1s) for Managers

This post is about One on Ones (1:1s). Specifically, we are talking about a weekly or biweekly scheduled meeting between a manager and a direct report.

Andy Grove, former CEO of Intel and author of the seminal High Output Management consider them some of the most valuable time you could spend as a manager:

Ninety minutes of your time can enhance the quality of your subordinate’s work for two weeks, or for some eighty-plus hours.

Ben Horowitz, half of the eponymous Andreessen Horowitz VC firm and author of The Hard Thing About Hard Things considered skipping 1:1s to be a fireable offense:

Me [Ben Horowitz]: Are you aware that your manager Tim has not met with any of his employees in the past six months?

Steve: No

Me: Now that you are aware, do you realize that there is no possible way for him to even be informed as to whether or not his organization is good or bad?

Steve: Yes

Me: In summary, you and Tim are preventing me from achieving my one and only goal. You have become a barrier blocking me from achieving my most important goal. As a result, if Tim doesn’t meet with each and every one of his employees in the next 24 hours, I will have no choice but to fire him and to fire you. Are we clear?

Steve: Crystal.

– from the the chapter “A Good Place to Work”, The Hard Thing about Hard Things

If you don’t think 1:1s are important, I hope to change your mind and/or help you do them better.

Why we do them

The main reason is that you as a manager are responsibile for making your direct reports excel and moving the needle on important outcomes. In order to do this, you have to know about your team. You can’t improve anyone’s work or career trajectory or fix any issues if you don’t know what is broken. And there are always things to work on.

There is a lot that manager should know about their reports. At a minimum: are they working on the right thing, how they are performing and are they happy. Here’s an extended list of some stuff (but not all!) that you should know off the top of your head for every direct report:

  • Do they feel safe?
  • Are they challenged? Are they learning?
  • Are they working on things that make a difference? Move the needle in some way on something important? Do they know why they are doing the work they do?
  • Are they over-performing? Under-performing? If so, do they know it?
  • What are their short/long term career goals? Are they achieving them? Do they know how to achieve them?
  • Are they struggling or frustrated? Are they a flight-risk?
  • What are they concerned about? What do they think is broken?

There are more. And you’ll never find out unless you talk to them on the regular. This is why you should be doing one on ones as a manager.

How do you find out the above? Communication.

Communication is Oxygen.

I don’t recall where I first heard that, but organizations that don’t communicate often stagnate and see an increase in toxicity.

The most succinct purpose of 1:1s I’ve ever heard came from an ex-military turned startup founder who phrased it like so:

We do 1:1s in order to: 1) Increase Communication and 2)Reduce Confusion

You don’t need an update on every topic/question listed above at every 1:1, but over the course of a quarter or so, you should hit most all of them.

As for reducing confusion, I mean reduce confusion on every topic: team organization, pricing models, fundraising, lotto tickets, giraffes, career tracks, whatever.

You should have an answer, be able to research an answer or point the person in a direction to get the answer themselves.

Tactical advice for better 1:1s

If you don’t see the value in 1:1s by this point, I’m probably not going to convince you. If you want to get better at doing 1:1s, you are in the right place.

Good practices

Address any confusion. This should be obvious. Explain away any points of confusion around any topic. Alternatively, do the research and get back to them or introduce them or point them to someone who can address the confusion.

Identify any blockers. Help address them if possible or give hints and let them solve it themselves if you want them to learn the lesson deeply.

You should be occasionally, but regularly talking about long term goals and career path. Ideally the 1:1 is a place to identify these gardens and tend to them. Check in and give feedback on how your people are trending relative to the medium and multi-year goals they’ve discussed.

Give effective feedback, timely and safely

This is one of the most important areas for a manager to be effective.

Positive feedback is easy to give, but also easy to forget to do. Negative feedback is hard to give and often procrastinated. Give both kinds of feedback regularly.

Ideally the feedback is effective. Usually this means the feedback is actionable in someway. What is the point of learning or actionable takeaway? If there is none, you’ve given them a zen koan, not effective feedback.

Positive feedback should be constructive, and ideally objective. “You’re doing a great job” or “Excellent work” is positive, but not really helpful. Be specific. Give examples, describe the positive outcomes that occurred and/or the negative outcomes that were prevented. Explain second or third order effects in detail: “Because you implemented that feature for customer A, customer success got a postive NPS score from that user. Marketing took that example and turned it into a case study which helped Sales close…”

Practice giving negative feedback so that you give it safely. You want your reports to learn and improve from the feedback you are giving them, as if it is a gift. This is hard! Very often an employee will slip into a defensive mindset and that’s not conducive to growth or improvement. The book Radical Candor by Kim Scott is based on this. For more on Psychological safety, checkout the seminal write up here or my take on how empathy and PS tie directly to high performing teams here.

Be present

Do whatever you can to limit distractions and interruptions. Often, this simply means turning off or putting away the laptop, phone, etc. Sometimes this means scheduling a quiet room instead of a walk in the park.

The important part is that you the manager are focusing 1000% on your direct report. This is their time. As much as possible Listen. Like a customer development interview, you should be listening the majority of the time.

If you are distracted because of some fire going on in Sales, DevOps or Customer Success or whereever, just reschedule.

Bad Signs in One on Ones

If your 1:1s are all about the weather or sports or fluff topics, something has gone wrong. A little bit is fine. You probably should be getting to know the people you work with better, but it should be the minority of discussion time.

If your 1:1 is mostly a status update, that’s a bad sign. There are other ways and mechanisms for this such as daily standups, chat/Slack/Teams, email, etc. An obvious exception is blockers or areas of concern where a direct report would like help from a manager. That’s totally fair game for a one on one.

As we mentioned above, If the manager is mostly talking, that’s a bad sign. While the responsibility of doing the 1:1s is on the manager, the purpose is to make the direct report awesome at their job. A manager should typically be prompting, listening and responding.

They should rarely be skipped. Rescheduling is fine. On a quiet week, you can even cut them short. But you should always do them.

Taking Notes

There are lots of ways to do this well. First, you should be taking notes. You want to be able to go back in time and see that their confusion is being reduced and they are making progress on short and long term goals.

I’ve been very successful with paper notebooks. By writing the date and reports name in the top margin, I can quickly thumb backwards in time. No special organization is required.

There are phone and web apps that are designed for 1:1s and some people use their companies document solution (google docs, etc) or even something like a private slack channel/DMs. I personally find that while a shared digital asset has it’s benefits (primarily, sharing the notes) the disadvantage of having the laptop or whatever open outweighs them. As mentioned up in the Good Practices, section, Be Present.

Venue

I prefer small conference rooms. It’s both easier to be present and take notes. Others like to go on walks or hit the coffee shop or cafeteria. In general, I tend to defer to what my reports prefer. As long as you are able to focus on your reports, venue shouldn’t matter much.

How often

Here’s a general guide on one on one cadence:

  • more frequent if they are your direct reports
  • Just let people know you exist? Less often works.
  • Coaching and feedback? More often is going to be better. C/F seems less important if you aren’t the direct supervisor.

As a manager or director, here’s where I start.

  • my boss: weekly or biweekly
  • my reports: biweekly
  • my reports’ reports: 1/month or once every other month
  • peers: if necessary, bi-, tri-weekly or monthly
  • everyone else: once/qtr

For any individual, the cadence can be increased or decreased depending on need. Do they need more support or are struggling in some way? more often. Do they run fairly autonomously and are happy? less often.

The important part is to not skip them. Reschedule, sure. But don’t skip them.

Prompts

Here are some of my most commonly used:

  • Aything on your mind?
  • What does not make sense?
  • Are you Learning?
  • Are you Enjoying?
  • What is one thing you’d like to tell me but you’ve been holding back?
  • Any Blockers?
  • What have we not talked about that we should be talking about?

And others I will sprinkle in as necessary or just for variety:

  • What are your priorities? What do you think should be your priorities?
  • Anything you are proud of?
  • What is most broken?
  • What bothers you or worries you the most?
  • What are your goals for the year?
  • What would you like to be learning about?
  • How can I support you?
  • How can I help you get to where you want to be?
  • What’s your plan for getting to where you want to be?
  • What have we not discussed that we should be discussing?
  • What is something you’d like feedback on?
  • Does the direction of the team/dept/company make sense?

Don’t forget to get some feedback for yourself every now and then:

  • Do you have any advice for me?
  • What have I done that doesn’t make sense?
  • What have I said or done that you are glad I did?
  • Is there any advice you have for anyone in the company you’d like to give? If so, why haven’t you given it?
  • Is there anything I could do or stop doing that would make it easier to work with me?

If you get generic answers like. Fine or Yes/No, silently count to ten and make them endure the silence to see if that draws out more candid answers. I’m surprised how often this works.

Lara Hogan has a nice list of prompts for your very first 1:1, which tends to lean towards getting to you know you, both personally and professionally.

After you build some comfort and safety, you can sometimes probe deeper:

  • What is something that people often misunderstand about you?
  • What is the lesson that took you the longest to learn and why?

Skip levels

These can be good for reducing confusion. Sometimes you can give a different perspective.

It’s very important that you don’t use skip levels to circumvent the normal hierarchy. You don’t want to a skip-level to be a mechanism where a report’s report can bypass or workaround a manager.

Wonderful 1:1s

I often summarize management as “Making people excel at doing important work.”

The work we do as professionals doesn’t often stay static. Most of the time, you can’t simply measure efficacy with quantitative numbers.

You have to do the people work of talking to your reports. Good one on ones are among the most effective and efficient ways to develop your people, influence outcomes and create safety.

I hope you have and host great 1:1s.



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