We all want to build and lead high-performance teams, but where do you start? And how do you keep the momentum going over months and even years? On many tech teams, a cornerstone of building a strong team is the one-on-one meeting. It’s an important opportunity to connect with a manager or direct report, (or even a peer). One-on-ones are a chance to get honest about what has you excited or frustrated; it’s a chance to clarify goals and priorities; it’s a way to build rapport and trust.
Given that one-on-one meetings are such a valuable opportunity, it’s odd that so many managers simply wing it or don’t do them at all. All too often, people go into a one-on-one with little idea of what they want to cover and why. In this post, we team up with Brian Bell of DataRobot and Jason Evanish of Lighthouse to curate some one-on-one best practices that help engineering teams perform well.
As a manager, Brian Bell has his work cut out for him. He’s an engineer and data scientist at DataRobot, managing a team of 17 other engineers who are located across the US and Ukraine. Despite the hard work that comes with managing so many people, Brian clearly enjoys the work, and it sounds like he’s quite good at it. Brian’s approach to management hinges on a few key principles: transparency, aligned motivations, and effective guard rails. He shares his perspective on running a high-performance team by applying these principles to each and every one-on-one meeting.
Jason Evanish, CEO of Lighthouse, spends his time thinking about how to facilitate better one-on-ones. His team builds a product that helps people manage their teams better. Jason notes that all too often, people use one-on-ones for status updates. They talk solely about projects, leaving no time for the less tactical – but very important – topics related to personal needs and development.
Jason shares his thoughts on how to balance different priorities during one-on-ones and how to make sure managers have the right training. Given his company’s focus on developing better managers, Jason has seen how thousands of leaders and teams approach one-on-ones. He offers insight into what works and what doesn’t, as well as advice his team has curated from some of the best managers and leaders in the world of business and tech.
Establish a Cadence
Let’s start with the basics. Jason underscores the value of scheduling one-on-one meetings well in advance. This creates predictability and also fosters a sense of trust. Even showing that you follow through on your one-on-ones demonstrates that you care:
“With how busy work is for everyone, if you don’t at least have a placeholder, it’s very hard to keep a rhythm and thus build trust with your team that you value these discussions and will be sticking with them.”
Brian is similarly bullish on holding one-on-ones every week, at least once a week. With certain people, it’ll sometimes be two one-on-ones per week if the person is spearheading something critical or needs additional support. When he does two in one week with the same person, he tries to carve out specific focus for each:
“One meeting is all about ‘how are you doing, how is work going?’ I want to know if the person is feeling productive, feeling behind, what they’re looking for with a project. The other is for talking shop: what’s going on with the project.”
Brian believes it’s good to keep a wall between those two topics. A project might be going well, but the person might be struggling in terms of morale or mindset. This struggle can get overlooked if the project is trucking along. Brian recognizes that the people on his team are in it for the long haul. Less important is the progress on a given, individual sprint; more important is how that person feels about coming to work every day.
Even if he’s only meeting with someone once per week, he tries to carve out time for more personal topics. He wants a regular check on whether people feel motivated and excited about what they’re doing. This meeting cadence lets him keep a finger on the pulse of how each person is faring, personally and professionally.
Jason points out that a regular cadence also helps foster accountability. People know in advance when they can circle back on a topic:
“By scheduling the next one, you increase the value of the current meeting; you both know when you’ll meet again and revisit the topics you discussed. This helps ensure momentum and accountability meeting to meeting.”
If you haven’t already done so, put a recurring time on the calendar for one-on-ones. Commit to following through, and if you must cancel or reschedule, do so in advance. Check in with your teammates about whether that day or time of day works well for them.
Transparency and Trust
Trust is often established by both listening well and sharing. There’s a time for both, and the key is striking the right balance. Jason believes most leaders could spend more time practicing their listening skills. Good listening can help develop trust between colleagues.
“This means asking more questions and creating space for your team member to speak. Learn to ask “what” and “how” questions, create space through intentional pausing, and ask good follow up questions to be a more effective listener.”
Jason cites one of his favorite quotes on listening, from the CEO of SoulCycle in a NY Times interview:
Brian points out that one-on-ones can be a good chance to build trust in another way: it’s a chance to share intel with others. He believes in sharing as much info as possible with the team. When he’s in a management meeting and hears about a new priority or useful data point, he’s quick to ask if he can share with his team. He knows that good decisions often come from having relevant context:
“There’s nothing more frustrating than knowing things are happening, but having no idea why. Just saying ‘we’re doing it’ is unhelpful.” Fighting for transparency will get you a lot of loyalty on the team. If you can’t be honest, they’ll never trust you again.”
This trust is the cornerstone of his commitment to empowering his team to make good decisions. Brian believes that if you’re hiring the right people and training them well, you shouldn’t micromanage.
His most important job is to hire well, train well, and trust others. He likes to think of a manager as a multiplier effect on other people’s success: help them they can focus on what they’re doing and build skills.
Before your one-on-ones, think about what information you might possess that your direct reports do not. Jot these items down, so you don’t forget to share that information. Doing this on a regular basis helps your team see that you’ve got their backs.
Personal and Professional Goal Alignment
Jason believes in establishing a common understanding of what team members want to accomplish, professionally. For managers who don’t know where to begin, he shares some ideas. The questions Jason suggests can help spark conversations that build trust and create a shared understanding about employees’ goals. Some proportion of one-on-one meetings should touch on an individual’s professional goals.
Brian also strives to balance his focus on company goals and individual goals. During one-on-ones, he digs into people’s motivations: what are they looking to achieve in the short-term, medium-term, and long-term? What are they hoping to do, personally and professionally? When personal and company goals are well aligned, that’s where the magic happens. When a team member is motivated by a project or opportunity, he or she is more likely to perform well.
He believes that strategic planning must dovetail with the needs of the team. The choice of an individual’s focus or project, the project team lead, the people on the team: these are all critical to get right.
“People become engineers because they like hard problems, and that’s also why they’re at a startup. They’re there in part because they get to build more interesting things. If you realize this is what they came for, you spend more time considering who’s on what projects and why are they there.”
If you can’t find an answer from why they might be interested from a growth or technical challenge perspective, then watch out. This might signal that goals are misaligned. Consider whether you can ask a team member to work on something else, something that better aligns motivations.
Make a note to yourself to have some of these deeper conversations at least a few times a year. Consider adding reminders to your private calendar, so that you make time for conversations that, while maybe not urgent, are certainly important.
Set Effective Guard Rails
Even when motivations are well aligned, team members also benefit from guardrails to help guide their decisions and behavior. Guardrails also ensure there’s consistency across team members and projects. For instance, Brian invests significant time with each new team member, teaching him or her how to write great technical specifications:
“You want them to spell out the right things: timing, risks, alternatives, probability of success….if you invest the time in writing great specs, it pays off.”
Brian also tries to establish guardrails in terms of timing. He acknowledges that it can be easy to lose track of time and suggests being upfront about hard stops at the outset. If both people are aware of time limits, there’s motivation to cover the most important things up front. It creates a shared sense of urgency.
He also suggests being aware of how long different people take to “warm up”. Some people might get right down to business, while other teammates might not voice their needs until 30 minutes into a meeting. Adjust meeting lengths, based on track record, and tailor them to each individual. The best managers adjust the way they communicate, based on the person’s personality and habits.
Jason advises that one on one meetings should be at least 30 minutes long. Ideally, they’re a bit longer, in case the prior meeting runs late. He references Andy Grove’s notion of “zingers”. These are intense topics, brought up with little warning or time.
Andy Grove warns about zingers in his book, High Output Management. If something sensitive comes up, most managers want time to dig in. But too often, there’s insufficient time to respond appropriately. Jason suggests budgeting more time and ending early if need be:
“Most people do not feel comfortable dropping a bomb in a meeting in the first 5 minutes, so scheduling more time ensures you can both warm up a bit and get comfortable before bringing up a difficult subject. ”
Set (and follow through on) at least 30 minutes for your one-on-ones. Be vigilant about the time, and don’t wait until the last moment to probe into what else might be on your team members’ minds. You might even consider pinpointing all the items to cover in advance, so that you can hone in on the ones that could be “zingers.”
One of the biggest risks with one-on-ones is failing to keep track of action items. Doing what you say you’ll do creates trust and a sense of accountability. It demonstrates that you’ve heard them and shows you value the person’s needs and concerns.
“I take notes, and it’s really important to do that, even if we’re in a coffee shop or going on a walk. Don’t be afraid to say, ‘hold on, I want to take a note.”
Jason offers some tips for taking notes in a polite way, no matter where you are or what constraints exist. For example, the notebook approach works well in coffee shops or situations where you don’t want technology to interfere with your rapport. Split-screen note-taking, on the other hand, works quite well when meeting with remote employees. He shares other great tips on the when and how of note-taking.
Brian suggests sharing these notes afterward to further encourage accountability. He then holds himself accountable to make sure he’s removing bottlenecks for those around him:
“Do the little things that “un-bottleneck” other people. Don’t focus on your inbox for 25 min when five people need you to do some five-minute tasks to get them unstuck. They’re trying to play their awesome role on the team. It’s really important that you’re looking out for their well being, which is demonstrated by actions, not just words.”
This documentation and creation of accountability also ensure that the important (but perhaps not urgent) things get done. Too often, the urgent can take over. Documenting needs, concerns, and follow-up items can help create space for the important things that might otherwise go overlooked.
This one is straightforward: take note of everything you say you’ll do, and do it. There’s no shortcut on this. Holding yourself accountable to your team will pay off in trust, loyalty, and good work; make the time to do this right.
Rolling Out a New One-on-One Format
If you do want to adopt some of these best practices, think about how you want to roll them out to your team. Some employees get spooked by any sort of change. They may question what was wrong with the previous approach. Some may feel discomfort at the new routine.
Help people gain confidence in your approach by explaining how the new format aims to better align people’s needs and the company’s goals. Share your interest in getting the most out of one-on-one time. Communicate with everyone on the team that you’re trying these new processes, and encourage feedback.
There’s no single one-size-fits-all method for running great one-on-ones. Brian notes that he’s gotten to this level of sophistication through trial and error. Jason suggests starting simple before graduating to some of these more pro-level techniques. Experiment with some of these best practices, and see what works for your team. Please share your feedback on what has worked well for you.
The Five Pillars of Great One-on-Ones
- Build and commit to a regular cadence
- Embrace and foster transparency and trust
- Continuously seek to align personal and professional goals
- Set guardrails that will keep your meetings on track
- Hold yourself and your teammates accountable
Want help putting these good one-on-one habits into practice and to learn more of them? Jason’s company, Lighthouse, can help you. Learn how and get a 21-day free trial at https://tettra.getlighthouse.