Guideline - One on One

Goals of 1:1

The goal of these meetings is to form the core of the relationship between managers and their direct reports. It’s especially useful with creative people, where management isn't about telling people what to do.

One-on-one meetings are the platform to build trust and rapport in a manager-report relationship to make teamwork effective. The idea is that you both give up time to sit down together every week and talk about whatever your member of staff wants to.

Always remember; the one-on-one meeting belongs to your report. As a manager, you have an opportunity to steer the discussion in a particular direction and to help your reports solve their problems. It’s also a great opportunity to work on career development with your engineers.

Ideal Frequency

There are different approaches to this, but We recommend you hold one-on-one meetings weekly. A regular, predictable cadence is essential, so your employee knows that you’ll make time for them.

It’s okay to not fill a whole hour; if you do it weekly, sometimes it'll only last 20 minutes, because there isn’t a lot to discuss. You both build up things you want to talk about with time, then you have an opportunity to discuss them, and the cycle repeats.

You can talk outside meetings too, as you likely do. The one-on-one meetings are about creating a private space, which is essential for many topics.

Preparation

Mixing it up

A template implies that you say the same things every time. We don’t have a template; We have a bag of different topics we can pull from. You can mix up a lot of questions for every meeting with different prompts to switch in and out.

Bring Specific Notes

It’s a great idea to take notes over the week and to bring them to the meeting. They can be observations about the dynamics in the team; they can be specific to your report or to any question that comes up. When it comes to engineers, you may ask questions about design or architecture; both are good topics of conversation.

Discuss career development

You should also mix in career development. The focus shouldn’t be on a performance review, but on asking how your team member is doing and what they're working on. You should try to learn if it’s in line with where they want to go and with what they'd like to try in the future.

Share information to learn

The information flow can go from the manager to the report as well. You can discuss topics that are interesting and ones that your report doesn’t know about. You can get their input and share insight from the management level.

Keep it friendly

Don’t forget, it’s a friendly conversation, so ask about how they are, what they've been up to recently, what they were doing on the weekend. You’re building rapport and trust, as well as discussing topics closely or loosely related to their jobs.

The bottom line is, use a wide spectrum of questions, and pull out a different mix every week.

Handling Challenging Personalities

  • The quiet type

    • Understanding that they don’t like to share thoughts and feelings helped me with them. This way, We could talk to them knowing it’s not that they don't want to talk to me; it’s just their personality.

    We have to prepare more for one-on-one meetings with them and bring more prompted questions. We also know if we cover everything with them, and there's nothing left to talk about, they’re happy with that.

    I encourage you to be open with your reports if you notice this and say, “We never seem to use the full hour, but it doesn't feel like there’s a lot left out every week. Is it okay, or is there something you may be hesitant to share?” These people on my team are usually fine.

  • The venting type

    • We need to dig deeper into the person

    We need to think, “How can we turn this negativity around into something positive?” Most likely that person didn’t even realize they'd been doing this. In this case addressing the problem head-on made it possible to start working towards a solution.

Documenting 1:1

The meeting note is a shared document. Create a private Google doc between you and your direct report. Only you and your report can see it and no one else. Keep a rolling meeting agenda in it, and encourage your reports to add anything to it at any time. This document collects information over the course of the week, open it up 15 minutes before the meeting to prepare. Read through it with your direct report, put the topics in order, and work through the list. As we're talking, the bullet points end up with actions we assign to ourselves, and we make sure we get them done.

It also serves as an archive of every one-on-one meeting you've had. You can check back anytime and see what you talked about. You can see the last time you spoke about a topic, like career development.

Critical Feedback at 1:1

One-on-ones are a frequent feedback opportunity

Give both positive and negative feedback. You can refine the way you deliver feedback if you read the book called Radical Candor by Kim Scott. It's about how to give critique and praise in a constructive, meaningful and honest way.

You want to get your relationship to a point where you can give negative feedback to each other without any hard feelings. It’s not about attacking anyone as a person; it’s about challenging ideas and behaviors. One-on-one meetings are a frequent opportunity to give positive and negative feedback.

The manager should always specifically ask for feedback too, for example:

  • Is there anything I could do better?
  • Have I been doing something recently that could have been better for you?

Give warning before a constructive feedback

We don’t want to give negative feedback as a complete surprise, but writing a long, painful monologue about how everything's wrong is a bad idea. We should default to writing an action item of the wider topic or a specific interaction or meeting we want to give constructive feedback about.

Then they enter the meeting knowing what topic we’ll discuss. This way, We have a chance to bring up positive and negative elements too, rather than spend half an hour heavily critiquing my team member.

Giving them an idea about what’s coming is helpful.

Common Mistakes

  • Turning one-on-ones into status updates

    • You shouldn’t allow your one-on-one meeting to turn into a status update. You can discuss what you’ve been up to recently, but going over daily tasks and avoiding topics like career development is a common mistake. This makes the meetings boring and unproductive, since you don’t learn anything new.

    All the information about tasks is available on your Jira or Trello board, so it’s redundant to discuss in person. A one-on-one meeting isn’t about making sure your direct reports are doing their jobs.

    You can easily tell if you’re doing it wrong. If you’re bored in one-on-one meetings, you need better material. When you’re discussing work-related topics, take whatever they're working on and look for things around the edge that make the conversation interesting.

  • Giving space for too much venting

    • Sometimes you end up with a report who vents at you all the time. You sit down with them every time knowing they’ll go on for an hour about how things are annoying, bad, take too long, or how they don’t like someone. When this happens, you need to intervene; otherwise, it’ll keep going indefinitely.

    Remember; venting to your manager is fine. Sometimes people get frustrated and need to blow off steam in a private setting. You should support this.

    If it becomes a recurring thing though, it's your duty as a manager to turn this into constructive energy. In this situation, you rarely have anything to say; you're just listening to a frustrated person. Sometimes you try to turn the conversation in a positive direction, but they just vent more, and you end up getting frustrated yourself.

    You should talk to these people about how to solve their problems and about how to engage with a negative situation to make it better.

  • Not involving outside help when necessary

    • In time you get to know your team members closely. Everybody goes through challenging periods. As their manager, you can help them with many things, but there are issues you aren't qualified to help with.

    You can’t fix mental health issues, medical issues, or personal things going on in their lives that affect their work. The fact that people bring them to you shows that they trust you, which is good news. At the same time, it makes you feel discomfortable because you can't help.

    This is the time you bring in outside assistance. It may be from your HR team, maybe you can use another employee benefit, or refer them somewhere.

    Being a manager doesn't make you a therapist. All you can do is recognize the situation and involve outside support. There is no training for this, but you can usually pick up on it based on your instincts.

1:1 with new team member

There's an exercise for this, called contracting, which people learned in management training. You write a contract between the two of you the first time you have a on- on-one meeting together. There are five questions to go through:

  1. Strengths and weaknesses

    2. Which areas would you like the most support with?

    It’s about figuring out what elements of their role they think you could help the most as a manager. It’s useful to set your focus areas about them.

  2. Feedback preferences

    3. How would you like to receive feedback and support?

    This is about finding out whether they like receiving feedback in the moment or if they prefer to sit down privately. They may prefer written or spoken feedback, and you can explore this area further.

  3. Potential challenges

    4. What challenges could there be for the two of you working together?

    You may be in different time zones, or you rarely meet in person. This question may cover a lot of things, including personality differences. An introverted person working with an extroverted may seem like a problem.

  4. Red flags

    5. What may be the signs the relationship is not working?

    It’s about trying to figure out the signs you can pick up on if things are going wrong, so you can try to get them back on track. For example, an employee may start giving brief answers when they get frustrated, or they may become quiet.

  5. Confidentiality agreement

    6. How confidential is the content of the one-on-one meetings?

    This sounds like a silly question because it's all confidential, but there are edge cases.

    If you mention someone making a decision they’re not sure about in a one-on-one meeting, am I allowed to talk to them about it? If I do, can I say that you raised the topic? Alternatively, everything can be treated confidential by default, and I’ll always ask for permission before doing something like this.

    This gives you a structured way of exploring deep things without making it difficult. You’ll both have it in writing, so it also serves as a reference point.

1:1 Questions and Topics

  • Talk about work with the quiet types

    • When it comes to less talkative engineering team members, We like to get up to speed with what they're working on. You can discuss if they’re learning something new, a project they're about to start, or a new piece of architecture they're designing. If you find a team member is quiet but loves engineering, you can start from there and build trust slowly.

    In this case, you don’t have to focus on the edge topics of their work, but talk about what they're working on directly. If they're designing a new part of the system, get them to draw it on a whiteboard and talk it over together. You can do this regardless of what they're working on; the point is to understand their way of thinking.

    You can read about the area they’re working on and share articles with them. It’s about bringing the conversation to them. This way you can ask questions and provide praise and critique.

    One-on-one meetings are about building relationships over time, and this is a way to extract opportunities to do it.

  • Bring whatever topic your report is comfortable with

    • People are driven by different goals.

    Some of my team members love to talk about career development, they can go for an hour about what they’re aiming for this year, where they want to be in three years, and what their dream is. Others talk about what they want to do, their ideas, or specific things they want to learn. The same question may stop different people in their tracks, and they have no answer.

    The questions you should bring to a one-on-one meeting should be about what that person is interested in. Then you can pull on that thread and build the discussion around it.

1:1 with individual contributor vs managers

The structure and the process are the same. The level of abstraction is different.

Individual contributors have a clearly defined job. You know what you can help them with and what their situation with their team is.

Engineering managers represent a team, so a one-on-one with them is not only about them. Their personal development and skills are one part of the equation. They’re also responsible for a team, their development and their skills.

Managers are a multi-layered diagram.

Talk to managers about their teams

A one-on-one meeting with an engineering manager is often about the team’s output, challenges, opportunities, and what can be improved for them. Starting from there, you can pick up on threads and move on to discuss a particular person.

It could be about the team leader's relationship with a team member, like a software engineer or designer. You need to navigate around their challenges and find ways to help them. The range of issues an engineering manager can be exposed to is much broader.

Use a coaching strategy on managers

Your engineering managers have a better view on their teams, because they’re working with them directly. You should focus less on the specifics, and turn it into a coaching relationship instead. The idea is to explore where they are, and to keep asking questions that lead them to think about the solution.

You can coach anybody. It’s a good idea with managers, because it’s a more abstract technique for a more abstract problem.

Preparing Engineering Managers to Run 1:1

Shared resources

We have an inside document with a dump of interesting one-on-one questions, and every engineering manager throws their questions in there. Any of our managers can look at it or add to it.

Make your culture do the work

If your engineering culture supports one-on-one meetings and everyone has them, you don’t have a lot to teach, because everyone learns through being part of the company’s daily life.

How Direct Report Should Prepare for 1:1

Take note of whatever topic comes to mind

We use a shared document with my reports to record our topics of discussion. The idea is that they capture any question or topic they’d like to discuss. That is usually enough preparation.

Bring your proactivity

As your team members get more comfortable talking to you, it becomes less about what they're working on and more about things like the company’s direction. Our reports tend to be curious about the company strategy, new HR policies, or new architectural matters. Then you can tell they’re at a good place with the company, as they absorb what's going on around them, and they explore it with you.

Finding out what's going on in your manager's brain can open up doors for you, because they might ask you for help, even if it’s just picking your brain on something. Taking on more responsibility could lead to promotions.

So be inquisitive, and be there to help your manager.