One-to-ones: essential to building trust, one conversation at a time

One of the most important tools I discovered in the management toolbox are one-to-ones (or 1:1s, or 1-to-1s, or… whatever you call a regular, frequent and structured discussion with teammates)

Although they seem innocuous, they yield the most power regarding the relationship between manager and team contributors, but also between any pair of individuals that have close work duties.

They are a bit daunting at first as a manager because you need to “lead” them, and if not carefully planned for, they can become useless, awkward, or overlooked.
Preparing doesn’t mean having a plan for each one of them but at least have a strategy of the goals to reach overall.

So first, what are 1:1s?

frequent (weekly/biweekly) meetings between 2 people who work together closely with an agenda focused on the relationship and growth of the parties.

In the context of Engineering Management, the most obvious one stands between the manager and each team member. Even though they can be profitable in other situations I’ll focus on the former use case.

Goal

1:1s should not be about status reporting. Even if that kind of discussion slips in, which is totally fine, this is never the goal.

If all 1:1s are spent discussing the progression of a feature, or the status of the next release before the customer launch, they are wasted. Instead, use those events as guides to focus on what your teammate can do better, how they can influence better outcomes, be less of a bottleneck, communicate better with other teams, etc…

Agile methodologies and other product/software development processes have also better ceremonies for status reporting.
1:1s are about individuals first, their pain points, their ideas, their wishes, their mistakes or flaws, and how to execute it all to grow careers, groups, and teams.

If there is a framework like OKR in place in the company, that could be used to frame some discussions, although I’d not rely only on that. Achieving objectives is important for growth, but growth is often about more than only a few quarterly objectives.

Make it safe

What is shared in 1:1s can be personal and sometimes difficult to say or hear. To build trust, what’s shared there should stay in the 1:1 framework.
Whether it’s improvement feedback, some personal situation, or some frustration, to build trust you need to listen and keep it private first. Then offer help and support depending on the situation.

That’s how the trust will be tested by individual contributors.

Coaching and development

That’s one of the most important aspects, which is also a difficult one, especially as a junior manager.

Coaching is about helping people grow in their careers and their lives. The most obvious is of course the promotion opportunities within the companies. But it’s not limited to that. Even without promotion opportunities, there are opportunities to grow:

• Experts in a particular technology can become better individuals by improving their soft skills, or broaden their technology knowledge (the T-shape concept for skills).
• Awesome team members can become better programmers by improving their test suits, or updating their technical skills on a particular framework.
• Great programmers can learn more about the team and the product by running some of the Agile ceremonies.
• Some individuals might have the preconceived idea that management is the only path to grow, while the reality is that management is a different job. Helping them understand that will help them make a more informed decision.
• Also, some individuals might be looking for opportunities that don’t exist in the company. As a manager and a coach, this is also important to identify and even help them find it elsewhere if necessary!
• Sharing feedback: coming from teammates, or the management, “negative” feedback is always difficult to hear or give. 1:1s are the perfect place to train that skill in both directions.
• Learning about other teams’ jobs is critical to understand the company. With the manager’s network and knowledge, contributors can have access to other teams more easily and that should be encouraged.

Rules

Below are my own rules for my 1:1s. There are probably others but I found these are the most important so far.

• Make it a priority, a habit, and an important ceremony. be on time, don’t replan them unless the meeting room is on fire.
• Don’t force any content or agenda, don’t force any answer. Some individuals don’t like sharing or have more difficulties giving feedback. Work on that first: show them trust and make it a safe place, then use some of the tools below to help it.
• Make it a safe place. What’s told in the 1:1 stays in the 1:1 unless for the part that explicitly needed to be shared. By default, what’s said stays private.
• Act on what you say you will act on. If you’re not sure you can help, say that you will try to help, and actually try and give honest and transparent feedback. That’s a critical piece of building trust. Showing your limits, but showing you’re engaged.
• Make it your report’s meeting. Maybe one of the most paradoxical parts, is that the meeting’s agenda, ideally, is given by your report. The manager's role is enabling and putting the framework in place, but the agenda should usually be controlled by the report: what’s on their mind, their pain points, their feedback, their questions to the manager.

Tools

During 1:1s, tools or frameworks like OKRs can be used to guide conversations. You should also focus on giving and receiving good feedback. (which is easier said than done)

But outside of larger frameworks or feedback, the tools below can be useful to use to guide some discussions and build trust.

Listening first

Guide the conversation, set up the framework, then listen. That’s the primary tool.

You should spend more time listening than talking if the meeting goes well.

Take notes also. Remember what they said about their next holidays, about their problem with person X or Z, or about that wish to learn about a specific technology.
Notes of past 1:1s are the first thing to read before the next one.

Chit-chat

Talking about pets, weather, holidays destinations, passions or hobbies is important. It’s usually best left around the coffee machine, but I believe it has its place during 1:1s. Especially in a remote work setup.

Chit-chat makes you know who is the person in front of you. What is their family situation? What are their passions? What do they do in their free time? Do they have any free time at all? Do you have common interests?

Those topics are going to give you hints on important events and problems in the future, such as why a usually great contributor is suddenly passing under the radar because he’s going through a difficult divorce, or whether they are likely to quit in the coming months to pursue other life goals…

Chit-chat is a great way to build trust one small brick at a time, but this should not be forced. Some people don’t like chit-chat and don’t want to talk about topics not related to work at work. This is fine. Just guide the conversation, but stop when they stop.
Although if you don’t like chit-chatting, that can be more problematic but not necessary a blocker. Remember management is mostly about humans, and you need to connect with humans. You don’t have to chat for hours, but asking a few questions about people’s life is going to bring you closer. Try it at least.

Work discussion vs. personal growth.

Work items are easier to fall back on when discussing between colleagues. Things like status reporting, “what about ticket XYZ”, or feature ABC, etc…
Day-to-day work is sometimes useful to just get started and is sometimes linked to actual issues or opportunities that could arise for them. But once again it’s not the end goal. If your report starts with that, listen then use work discussion as an introduction, ice breaker, or to funnel the discussion into something more meaningful for the report’s growth.

Ice breakers and conversations starters

With people who you don’t know yet, or if you’re only starting as an Engineering Manager, it can feel daunting to launch some discussions. below are some conversation starters that I used to get started on some interesting topics that can give you insights about the team, and the things that flew below your manager’s radar.

They can be used when you have time or if you run out of discussion topics. (To have a more complete answer, use the silence accordingly after asking those questions…)

1. Are you afraid of anything at work?
2. Do you feel you’re learning things? Are you bored?
3. Have you seen something recently and thought to yourself “I wish we’d done that”?
4. Is there something we should measure in the company that we currently don’t?
5. Is there any part of the company you wish you were able to interact with more?
6. Is there an area outside your current role where you feel you could be contributing?
7. Is there anyone at the company you wish you could work closer to?
8. Have you seen someone here do great work that’s gone unnoticed?
9. Are there things you don’t know about the company that you feel you should know?

The power of silence

For negotiators, I read silence is a tool. For 1:1s, I found it’s also a good one, although you need to be ready for the awkwardness.

Used at the right time, or after the right question, silence can force people to open to fill the void. Silence is difficult to handle. But a small awkward silence can bring you much further than hours of chit-chat. It makes people think, it makes people wonder what you want to hear to get out of this slightly uncomfortable situation.

A few tips I had for myself to handle silence:

• Use it once in a while only, when you feel you’re getting nowhere with the discussion, or stay on the surface of an important topic.
• Get the timing right. Using silence after asking them if their pet recovered from its latest surgery is not going to bring you anywhere.
• Repeat in your head: “I will not talk first” as long as possible, or give yourself a threshold and count seconds silently. If it lasts more than 30–60s, the person you have in front of you is pretty tough!

Silence also reminds you to listen, and stop talking. Which is important in 1:1s as a manager.

Built in quiet times, stressed in difficult times

As I could witness, 1:1s feel the most useless — and sometimes even a complete waste of time — during the quiet and easy times, when everything seems to go right and everyone is happy.

They actually show their unique utility when things start to smell “funny”. When conflicts arise, when the company goes through a difficult time, when special events happen that put stress on the team.

If done right during quiet time, trust will build up. And when chaos comes, this trust will be one of the most powerful tools to keep the team together. You’ll have a unique and personalized way to talk with each individual about the current situation, to understand how it’s affecting them. And they’ll all have a safe and personal place to talk about concerns and give you honest feedback.

Don’t skip 1:1s when things are going all good unless your report asks for it. Keep that schedule, connect, and in the worst case, it will take a few minutes of your week and add a few trust credits to the balance. Which is a good deal as a manager.