The Ultimate One-on-One Meeting Guide: Beat the Awkwardness

The Ultimate One-on-One Meeting Guide: Beat the Awkwardness - Interview with James Stanier, SVP of Engineering, Brandwatch

You know that awkward silence in one-on-one meetings, no matter which side you'd been on. You're not sure where to take the discussion in this semi-informal meeting, so you're just suffering in silence.

Don’t worry, it’s not just you.

It’s every engineering manager and engineering leader ever.

This leads to a lot of pressure when you're running one-on-ones. Until you gain experience it’s not obvious at all how to approach them, what tone to use, and what topics to discuss. Yet running effective one-on-one meetings has become a basic requirement to be able to call yourself a good manager.

How do you get the basics right without jumping in at the deep end completely unprepared, and embracing the pain until you improve?

Get good at running one-on-one meetings using the experience of James Stanier, SVP of Engineering at Brandwatch, and author of Become an Effective Software Engineering Manager. The interview is from the Level-up Engineering podcast, hosted by Karolina Toth.

We’re covering:

• The goal of a one-on-one meeting
• The ideal frequency of one-on-one meetings
• One-on-one preparation tips for engineering managers
• Mix it up
• Discuss career development
• Share more to learn more
• Keep it friendly
• Handling challenging personalities
• The quiet type
• The venting type
• Documenting your one-on-one meetings
• Critical feedback at one-on-ones
• One-on-ones are a regular feedback opportunity
• Give warning before critical feedback
• Common mistakes of engineering managers
• Turning one-on-ones into status updates
• Giving space for too much venting
• Not involving outside help when necessary
• The number of direct reports you can handle doing one-on-ones with
• Walking versus sitting one-on-one meeting
• Doing a one-on-one with a new team member
1. Strengths and weaknesses
2. Feedback preferences
3. Potential challenges
4. Red flags
5. Confidentiality agreement
• One-on-one meetings questions and topics
• Talk about work with the quiet types
• Bring whatever topic your report is comfortable with
• Doing one-on-ones with individual contributors vs managers
• Use a coaching strategy on managers
• Talk to managers about their teams beyond themselves
• Preparing engineering managers to run one-on-ones
• Training and workshops
• Shared resources
• Make your culture do the work
• When to start doing one-on-ones
• How direct reports should prepare for one-on-ones
• Take note of whatever topic comes to mind
• Bring your proactivity
• Bonus advice
• Integrate one-on-ones into your culture
• Use peer one-on-ones to build your network
• About James Stanier

What is the goal of a one-on-one meeting?

One-on-one meetings have different names written in different forms, like one-to-one, 1-on-1, one on one, 1-1 or even 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.

How often do you have one-on-one meetings?

There are different approaches to this, but I 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.

How do you prepare for one-on-one meetings as an engineering manager? Do you use a one-on-one meeting template?

Keep mixing it up

A template implies that you say the same things every time. I don’t have a template; I have a bag of different topics I 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.

Common challenging personalities at one-on-one meetings for engineering managers

The quiet type

I’ve had many quiet people as a direct report. Understanding that they don’t like to share thoughts and feelings helped me with them. This way, I could talk to them knowing it’s not that they don't want to talk to me; it’s just their personality.

I have to prepare more for one-on-one meetings with them and bring more prompted questions. I 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

I’ve dealt with employees who were venting all the time. I’m a good listener, but it can backfire when I run into these people. The first time I had a direct report do this early in my management career, I had no idea what to do.

Many weeks went by until I finally said, “How can we turn this negativity around into something positive?” It turned out 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.

How do you document your one-on-one meetings?

The meeting note is a shared document.

I create a private Google doc between myself and my direct report. Only we can see it and no one else. We keep a rolling meeting agenda in it, and I encourage my reports to add anything to it at any time.

This document collects information over the course of the week, and I open it up 15 minutes before the meeting to prepare. We both read through it, 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.

Do you give negative feedback at one-on-one meetings?

One-on-ones are a frequent feedback opportunity

I 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

I 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. I tend to write an action item of the wider topic or a specific interaction or meeting I want to give constructive feedback about.

Then they enter the meeting knowing what topic we’ll discuss. This way, I 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.

What are the common mistakes in one-on-one meetings for engineering managers?

You can avoid the common mistakes reliably by listening to your gut feelings. They always give you red flags.

Status updates bore you

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.

Constant venting makes you frustrated

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.

Personal or mental health issues make you discomfortable

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.

How many direct reports can you handle doing one-on-one meetings with weekly?

In my experience, if you have more than seven or eight direct reports, it's starting to get too much. Ending up with more direct reports than that tends to be an organizational problem. You may need to promote middle managers to support you.

I currently have six direct reports, and the maximum I’ve had is ten, which was too much. If you're spending an hour every week with each of your direct reports, it takes seven hours with seven people. That’s a full day.

If you add in prep time for each one-on-one meeting and follow-up, it takes a big chunk of your week just to go through the one-on-one cycle. On top of this, you have a lot of work to do.

I say five to seven direct reports is the sweet spot with weekly one-on-one meetings.

What setting do you need for one-on-one meetings? Do you prefer walking or sitting one-on-ones?

A private setting is the baseline

Currently, we’re working remotely due to COVID-19, so we’re using private Zoom rooms.

The default setting is a private room, and the trust you bring with yourself. That's what matters. A place where no one else can hear you allows both of you to talk about whatever you want to.

People sometimes go to coffee shops, and that's fine. It’s more interesting than sitting in a random room, but it's tricky, because you don't always feel comfortable talking around strangers.

There's a nice coffee shop near our office in Brighton, and our people started going there for one-on-one meetings. Suddenly, so many of us were there regularly, that you couldn't have a private conversation because colleagues were sitting just a few seats away.

Sitting down is the standard

I prefer to do one-on-one meetings sitting down, but a walking one-on-one is an option too.

Walking meetings are more adventurous, but they can be distracting for both of you. It also makes taking notes a pain, so you have to remember everything you’ve discussed, and write it down as soon as you return to the office. In a meeting room, you can take notes easily.

You could also ride a bike, but then you’ll only be able to talk so much. I also tend to lose the ability to keep track of the discussion effectively.

How do you use one-on-one meetings to build trust with a new team member?

There's an exercise for this, called contracting, which I 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

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

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

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

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

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.

What questions do you bring to a one-on-one meeting?

Talk about work with quiet people

When it comes to less talkative engineering team members, I 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.

Talk to everyone about whatever they’re 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.

What’s the difference between one-on-one meetings with engineers and one-on-ones with engineering 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 coaching strategies with engineering 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 engineers or managers; you can coach anybody. It’s a good idea with managers, because it’s a more abstract technique for a more abstract problem.

How do you train engineering managers to run their own one-on-one meetings?

All the managers who have been direct reports to me have been at the company for a long time. We’ve all learned by doing it.

Training and workshops

I’ve held training sessions for engineering managers about doing one-on-ones. Similarly, I’ve held insider workshops about delegation and other aspects of engineering leadership. I explain the basic processes of the shared document, booking time in the calendar, pros and cons for different environments, and so on.

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.

The company culture does 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.

When I joined Brandwatch, one-on-ones were awkward, because no one had done them before. In this case, it's worth doing a formal workshop or training. There are good resources online as well.

When did you know you need to run regular one-on-one meetings at Brandwatch?

It became necessary as we grew

It came with scaling our engineering department and creating a more formal management structure. When I joined the company, everyone reported to the CTO. In reality, people just walked in and did their jobs, which is fine as long as you’re small.

As you keep hiring engineers, not everyone can report to the CTO forever. No one can handle 50 direct reports. So we formed teams, appointed engineering managers, and that brought performance reviews, career ladders, one-on-one meetings and more.

This was the time I transitioned to engineering management. I read a lot to get myself up to speed, but there were fewer resources tailored for engineering leadership.

The first one-on-one meetings I had with my team were awful. I had no idea what to talk about, and I was in a room with employees I didn’t know too well for an hour. There was a lot of silence and awkwardness.

In time, I built up my bag of questions, and it became natural. As you build a relationship with your direct reports, you start looking forward to it.

Outside expectations

There is also outside pressure: the employees you hire expect their managers to make time for them. Every good company does one-on-one meetings, so you should too. I loved going down the rabbit hole reading everything there is about one-on-ones to extract the good parts and bringing them to the company.

Weekly one-on-one meetings aren’t forced; our managers can do them as frequently as they want. We expect every manager to do them, and our basic recommendation is to schedule these meetings weekly.

What do you recommend for employees to get ready for one-on-one meetings with their manager?

Taking notes is all you need

I 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 with you

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. My 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.

This is what I do with my manager, Brandwatch’s CTO. I look for every opportunity to ask questions about what’s happening with the company.

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.

Bonus advice

Integrate one-on-ones into your culture

Aim to develop a company culture where everyone sees these one-on-one meetings and the relationships they build as essential. Receiving support from other managers and your peers to make the process better is great. Our shared list of questions every manager contributes to is an example of this.

Once you successfully integrate one-on-one meetings into your company's everyday life, employee performance and employee engagement will be noticeably higher.

Use one-on-ones to build your network

We don't limit one-on-one meetings to teams and their managers. You can do skip level one-on-ones, and you can talk to anybody in the organization. If you become comfortable at doing one-on-ones with your team, you can book a recurring meeting with a peer or with anyone at any part of the organization as well.

Build relationships and build your network through one-on-ones. Find out what's going on in other parts of the company. It’ll pay off when you need to get things done or when you need to find out information in the future.

About James Stanier

James’s passions are technology, management and leadership. He loves building things, and building people; this is why he recently wrote a book called Become an Effective Software Engineering Manager.

He’s currently SVP of Engineering at Brandwatch, and he is a passionate dog owner and runner on the side.