The engineering leader's guide to upgrading one-on-ones

Updated on Feb 5, 2023 | Read time: ~ 20 minutes

One of the open secrets to succeeding as engineering managers is building strong personal connections within our teams. Buzzwords like empathy, vulnerability, encouragement and engagement are used and reused for a reason--they’re important components of effective interpersonal relationships.

Yet collecting all the right components of quality leadership doesn’t itself build a quality team. Management is like a box of Legos: you have to be thoughtful in how you assemble them if you want to end up with the result you’re after. In a leadership context, gathering the right people that work well together is foundational to success and regular 1:1s are a powerful means to both understanding and nurturing that kind of healthy team.  

This guide will walk you through the fundamentals of 1:1s, the research that underlines why we should leverage them and a few frameworks for fine-tuning and evolving your approach to these essential meetings.

The reasons for having 1:1s are as diverse as the engineering organizations where they take place. They are preventative maintenance, check-ins on the health of a team and a safe space to vent or ask questions about work issues. A good way to look at 1:1s is an unscripted chance at open-ended conversation and an avenue where individual contributors can be heard. 

In a field that recognizes engineers should have their unnecessary meeting time minimized and their creative time made sacred, 1:1s are the type of meeting that’s gone from being highly unusual in the ’80s to becoming a manager’s de facto activity. So, when managers or contributors have a distaste for 1:1s, odds are the meetings aren’t being utilized to their capacity. They’ve become a chore rather than an opportunity. 

If holding 1:1s has become a painful or anxiety inducing process, it could be time to revisit the foundational steps to opening up this critical opportunity for dialog.

It’s hard to figure out what motivates people at work. Fortunately, we can look to results of an exhaustive research project culled from the Gallup global database of 10 million employee and manager interviews, as described in 12: The Elements of Great Managing.

The data from thousands of interviews revealed which aspects of work most effectively explained employees’ productivity and motivation in any field. These twelve elements of great managing encapsulate the core agreements—implicit or explicit—between employees and their managers.

And a full third of those elements relate to caring about your team members as individuals with aspirations and desires:

• Element #5 – My supervisor, or someone at work, seems to care about me as a person

• Element #6 – There is someone at work who encourages my development

• Element #11 – In the last six months, someone at work has talked to me about my progress

• Element #12 – This last year, I have had opportunities at work to learn and grow

Ultimately, good managers invest in and grow their people. It’s the campsite rule of managing: A great manager leaves you better than they found you. That’s not something that can be accomplished with lip service. It needs to be bolstered with consistent and meaningful action. This action starts with 1:1s.

We understand that managers of effective engineering teams don’t have their hands in the nitty-gritty of the code. The most impactful part of a manager’s role is clearing obstacles so the team’s job is easier, rather than providing feedback on specific details in projects. But engineers also need to hear feedback from their managers to feel satisfied in their jobs.

In fact, fifty percent of “high performers” report that they expect a 1:1 with their managers at least monthly. The same study found that less than half of those same high-performing employees (the top 40% of respondents, based on self-reported data about their most recent performance appraisal) are satisfied with their jobs.

In other words, regular 1:1s establish a cadence of communication, which in turn helps keep engineers engaged.

Of course, managers can and should provide feedback outside of 1:1s as well. But 1:1s offer certain benefits that most daily stand-ups, annual performance reviews and real-time feedback can’t usually provide:

• Fosters bottom-up and lateral communication and limits top-down communication

• Creates conversations that extend beyond a sprint, allowing for long-term context

• Offers a safe space to talk openly about the workplace, individual performance, team dynamics, product vision and an engineer’s future

• Enables a communication practice field, where the quality and quantity of information shared increases 

• Provides more ongoing value than intermittent forms of communication and review

Makes performance reviews easier because managers and engineers can work through constructive feedback throughout the course of the year

The relationship between a leader and an engineer is just that—a relationship—and like all healthy relationships, it thrives on communication. Building sound relationships comes from leaders truly getting to know the people on the team, so individuals are comfortable raising concerns and asking for help.

It can be admittedly difficult to know whether team members are bubbling up blockers as they face them. In a recent interview, Facebook’s VP of Product Design Julie Zhuo shared the questions she asks herself to assess the level of trust between her and her team:

• Are there other instances of this person struggling, in need of help and talking to me about it?

• In 1:1s, does the person give in-depth and vulnerable assessments of what’s going on, or is the response always simple, like “Things are fine”?

The answers to these questions, Zhuo says, will guide managers to an understanding of how much time and improvement their relationships with engineers require to be truly trusting and authentic.

Here’s the thing: mutual trust is an end goal in and of itself, and it also leads to happier, more beneficial, longer-lasting working relationships. After all, employees don’t leave companies—they leave their bosses. So if there’s one ultimate reason why 1:1s matter, it’s that regular, personal, attentive communication between a manager and an engineer keeps everyone engaged, invested and happy at work.

While there isn’t a one-size-fits-all approach to 1:1s, there are approaches to designing and implementing these meetings that can be successfully adopted in most environments. 

Kevin Hoffman, author of Meeting Design: For Managers, Makers, and Everyone, discussed how he applies design thinking to all meetings—including individual ones. Hoffman said, “more and more organizations are essentially taking the scientific method and applying it to design shipping—design thinking, as it’s commonly known. Learn something, come up with a theory, build a strategy, measure if it achieves your goal or not and then iterate. The same approach can also be applied to how we run meetings.”

In other words, 1:1s can be thought of as ever-evolving experiments. Hoffman has just one rule: their format should always serve the attendees, rather than the facilitators. 

“If we think about designing a user experience, we’re designing a user experience for the user. We’re not designing a user experience for the designer,” he said. “The meeting experience should be designed for the attendees who need to make the decisions. They shouldn’t necessarily be designed for management.”

Across the board with engineering leaders, the crux of a successful culture of 1:1s is consistency.

Many managers schedule 1:1s during the same block of time on the same day of the week to create a predictable rhythm. It’s often hard to find a mutually available block of time on short notice, so it’s also helpful to pre-schedule 1:1s six months in advance or as a recurring-with-no-end meeting. 

Experiment with 1:1 duration

The duration of 1:1s is much more negotiable than their cadence. Cases can be made for holding 1:1s that last 30 minutes, 45 minutes, even 90 minutes. Kevin Hoffman suggests establishing 1:1 times that allow both managers and engineers to use that time most constructively.

Let’s say that a typical engineer and a typical manager hold a weekly 30-minute 1:1, for a total of two hours each month. Rather than divide that time equally between weeks, Hoffman experimented with different durations of time for each 1:1. After some time, he said he ultimately found the greatest impact for his own team with meeting semi-monthly rather than weekly: he’d hold a 90-minute meeting one week, then two weeks later, hold a 30-minute meeting.

“For the 90-minute meetings, I wanted my reports to come to the table with a complex problem, and we’d work on solving it together,” he said. “We’d whiteboard it, we’d explore it, we’d try to map the problem out, whatever kind of conversation we wanted to have.” The half-hour meetings, then, became more traditional 1:1s, focused on personal growth, career development and individual experiences in the organization.

Hoffman discovered something else, too: his alternative format worked remarkably well for those engineers who were self-guided, didn’t need or want feedback on day-in/day-out tasks, or were generally established in their roles or even getting closer to promotions.

“For them, it was a really good format, because they knew when they got their ninety-minute meeting, they could really dive into something,” Hoffman says. “I was supporting them in a way that was focused on the larger problems that they might not have had experience solving, but I maybe did.”

Yet for people who were new to their roles—either new to the organization or the career, or freshly promoted into a new position—this format didn’t work very well. For those people, Hoffman found that a 45-minute weekly worked best, working down to a 30-minute weekly, then transitioning them into the 90/30 split.

In short, managers have to experiment to find out what works best for them and for their reports. It’s easy enough to find other managers’ strategies for creative inspiration online and among peers—and we encourage discovering what others have tried. But what works for one engineer (or one manager) isn’t a guaranteed success for another. The freedom to play with the format allows both participants to find what works—and to shift it when it could work better.

Avoid canceling 1:1s, and minimize rescheduling

Regularly canceling 1:1s with engineers can send the message that their managers don’t value listening to them. It certainly signals that their managers don’t prioritize it. 

Of course, 1:1s needs to be rescheduled on occasion because of life or work responsibilities on either the engineer’s or the manager’s plate. When that happens, managers can still demonstrate the importance of meeting with an engineer by aiming to reschedule for the same day, or as close to it as possible. Skipping 1:1s altogether sets a slippery precedent—and giving in to the feeling of “we don’t have much to discuss this week, so let’s forego this meeting” negates the importance of consistency in establishing a healthy cadence.

Granted, 1:1s are not routinely urgent. But outside of true emergencies, a team’s engineers are generally their manager’s top concern. Holding 1:1s sacred is the chance to prove that.

Since 1:1s are truly two-way streets, it’s important for both the manager and the engineer to prepare for them. These meetings are opportunities for deep dives into engineer experiences, goals and perspectives. Preparation allows both parties to jump right in instead of spending precious one-on-one time finding their footing. 

Here are some strategies for preparing effectively for both long-running and first-time 1:1s.

Take and review notes from previous 1:1s

In practice, the preparation for the next 1:1 starts during the previous one, particularly for managers who consistently take notes throughout and after each meeting.

Documenting the discussions that take place during a 1:1 is a wise practice for both participants. In fact, it’s often beneficial to share those notes with one another so that any discrepancies or misunderstandings can be caught before they extrapolate. After all, this is the engineers’ meeting—everything about it should be accessible to them. The notes aren’t secret; they’re for both people. For managers, note-taking also shows: 

• Signals they are paying attention to what they’re hearing

• Improves retention of what they learned

• Helps keep track of commitments they’ve made

• Provides a reference when it's time for a quarterly or annual performance review

• Illustrates the progress of conversations and relationships over time

And, of course, these notes provide managers with an immediate reference point for which threads to pick back up during the next 1:1.

Taking notes, and keeping a feedback log of the conversations held with engineers, aids with both the week-to-week cadence of meetings and the much higher-level view of an engineer’s career. Keeping track of what was discussed and when it happened offers managers a resource for establishing a cadence of themes. 

For example, during each 1:1, a manager is likely to ask some form of “How are you?” Conscientious notes will remind both the developer and the engineer to follow up this time on last time’s feelings. If an engineer is working toward a promotion, however, that’s not likely to become a weekly conversation. But it’s important for leaders to keep those high-level yet infrequent threads from being lost for far too long. Documentation of those conversations will help both parties to bring up the topic more regularly—they can even schedule time, say, monthly or bi-weekly to check in on it. 

Draft an agenda beforehand, and encourage engineers to do the same

These individual meetings with engineers are very personal. But that does not mean they are casual. Most managers would prepare materials and gather their thoughts before sitting down with the C-suite leaders. And 1:1s can have a greater impact when both the manager and the engineer draft an agenda for them.

These agendas could be jointly crafted on a shared document, or each person could draft their own. They needn’t be overly detailed or customized. After all, the 1:1 is largely a chance for an engineer to talk and a manager to listen—so a manager’s agenda is seldom a prescription for what they will discuss.

Rather, a manager’s agenda is more of a set of conversation-starters and conversation-deepeners. If engineers come without much to share, or don’t yet feel comfortable or skilled at crafting agendas, a manager can still be ready to open meaningful conversations. If your team member comes prepared, this is their time, so let ‘em rip. Their agendas largely drive the actual meeting. The more curious and empathetic a manager is to their team member’s thoughts, the greater the likelihood of the meeting being productive. 

But whoever’s agenda guides the meeting, the mere existence of one will help managers waste less time figuring out what to discuss and more time digging into what matters to their engineers.

Get to know each other—it’s never too late

Whether a duo has been conducting 1:1s the same way for years, or it’s their first-ever, it’s never too late to start getting to know each other. In fact, preparing a 1:1 with the attitude of understanding each other is a great way to improve a manager/engineer relationship, according to Lara Hogan, Engineering Leadership Coach and Consultant at Wherewithall.

“A little while ago, I shared ... a list of questions that you might want to ask the first time you have a one-on-one with someone. If you’ve missed that window, don’t worry. You can ask these questions anytime,” Hogan said. 

She recommends learning:

1. What makes the individual grumpy, and how to know when they’re grumpy, 

2. How your report prefers feedback and recognition

3. The person’s goals and needs (from you, from their team, etc.). 

“You don’t need to know these things today,” she said, “but you’re probably going to need to know in the future. You don’t want to find out how someone prefers to receive feedback, once it’s time to give them feedback.”

Year-end reviews are a typical requirement in the business world, but these meetings take the broadest possible strokes when looking at how an engineer contributed to the team, and to their own career goals. Effective 1:1s can fill in the lines between those brushstrokes by adding context with consistent reflection on quick wins, long-term projects and the other nuances that make up the engineer’s work and life. 

Set and discuss goals

Setting goals is part of every business, and 1:1s are a great way to help your team track toward those goals. While it’s important to let the team member guide the conversation, it’s helpful for both parties to map out what’s coming down the project pipeline, where it ties to the greater business objectives and how the engineer intends to accomplish the tasks. 

Talking regularly about goals and objectives gives the leader an opportunity to help course correct if something is not on track, or step in to their engineer’s aid if they’re hitting roadblocks. This also offers a space for the engineer to talk about their progress and how they feel about it. 

Lean on data when discussing progress

Regularly leveraging relevant, meaningful data in 1:1s can provide both managers and engineers with objective insights into their sprint-by-sprint experiences and their long-term career growth goals. 

Part of the process is a quantitative review—what exactly is going on. The other part is qualitative, where the goal is to understand the why behind the patterns and activities exhibited in an engineer’s output. 

Using analytics about the development process helps managers get the full picture of the what—so they can move beyond using 1:1s as status updates. Getting to the why creates more targeted conversations. It helps both participants identify the reasons behind blockers in the development process, rather than just fixing individual trouble spots. And, it can provide different insights into the higher-level conversations about career trajectories and personal growth.

Ultimately, data reports should help leaders rely less on pure hunches and assumptions, and be less susceptible to being swayed by unconscious biases. They should give managers a starting point and conduit to ask their engineers even better questions and have healthier and more productive discussions.

Ideally, most 1:1 meetings will feel uplifting, constructive and forward-looking. After all, the idea of these sit-downs is to improve the relationship between managers and engineers and advance the engineers’ careers and skills. But the skies aren’t always clear, and managers need to be ready to manage in the tough times. (And since we’re all human, guess what? Every 1:1 might be taking place during tough times, one way or another.)

Turn to the “feedback equation” for when work isn’t going well

When work is not going well for an individual on a team, it can be challenging to know how to approach that situation as a manager. Managers can turn to the classic three-part “feedback equation” when they find themselves in these conversations:

1. Can the difficulty be described as if it was recorded on a video camera? This is another way of framing how objective and observable the behavior is. Late deliverables are one example: they are demonstrably, observably late. However, an engineer “saying something stupid” is subjective. Effective feedback is grounded in objectivity.
   
   

1. What is the impact of the behavior? When a deliverable is late, the impact is that the team doesn’t ship on time, and the organization loses money. Again, objectivity lends itself to effective feedback. If managers cannot identify the negative impact of an engineer’s work, the feedback may not be worth giving—yet they can still examine it further to understand whether they were simply bothered by it, or whether the behavior is indeed consequential.
    

1. Ask an open question. Giving people command statements, like “Show up on time,” doesn’t help them feel heard. The manager/engineer relationship really can be a partnership, where the former is supporting the latter. So instead of instructing engineers how to behave differently, managers can make the scenario more collaborative by asking such questions as “How can we address this?” or “What can I do to support you in changing this behavior?”

These three considerations can help managers wrangle their concerns over an engineer’s work into a less worrisome feedback delivery session.

Assess how engineers need to release—and handle it appropriately

Even with a thorough preparation before a 1:1, managers don’t always know how it’s going to go. Heck, they never know with certainty how it’s going to go. Michael Lopp, the author of Managing Humans, uses a triage method called The Update, The Vent, and The Disaster to assess what state of mind his engineers are in during a potentially unproductive 1:1—and how he needs to handle it.

Lopp starts every 1:1 by asking one simple question: "How are you?" This question is more personal than “How’s it going?” and gets more quickly to the truth of an engineer’s experience. How engineers answer that question helps Lopp understand their mood, which (if it is not particularly constructive) is how he then categorizes their 1:1 into one of the following buckets:

1. The Update (“Everything seems fine! Let’s just do a status update.”): These are not good uses of 1:1 time. Listen for something that is driving their list of updates and explore it with them. If that fails try: 

   1. Have 3 prepared points from notes from you made in preparation for the meeting

   2. Run a mini performance review based upon the engineer’s last 1:1

   3. Switch to your current disaster to take their mind off what is driving status updates

2. The Vent (“I need to unleash on something at work.”): This is a mental release and you should listen to, but not solve the problem, comfort or redirect. When their vent concludes, try to: 

   1. Triage by unpacking the problem and move toward a solution

3. The Disaster (“I’m on the attack.”): The engineer appears to be looking for a fight, so prepare by locking up emotional reactions and avoiding escalating the situation with these steps:

   1. Defuse by not contributing to the disaster and letting the emotion pass

   2. Let it happen by not letting yourself respond with a negative reaction

   3. Reserve judgement upon the engineer as everyone is capable of these emotions and in many cases aren’t themselves during the disaster

Most 1:1s will naturally tend toward being in The Update category, unless the manager and the participant have established a healthy cadence of in-depth 1:1s. The Vent may happen semi-regularly, and it can ultimately open doors to productive progress. But when it devolves into The Disaster, that’s one of the most challenging moments a manager can face in a 1:1. Because it’s just gotten personal. The manager is suddenly on the receiving end of a barrage. 

The best thing managers can do in that moment is weather the storm without escalating it. The Disaster is a sign that the relationship here is not healthy, and likely has not been for some time. Once The Disaster has cooled, however, it’s time to start developing a stronger foundation, starting over from the beginning of this guide.

Acknowledge everyone’s limits in a crisis, even your own

In a recent interview, Lara Hogan discussed managing through crisis—whether that’s chaos within the company, struggles in an individual’s personal life, or events happening outside the company that affected people’s spirits and stability. In any of these scenarios, a manager won’t be able to see the full picture of what’s going on in people’s lives. “Every person is a universe,” Hogan said. “We’re bringing our full selves to work.” 

But managers can support their teams and create a safe workplace by focusing on clarity. In Managering in Terrible Times, Hogan writes, “The easier and clearer you can make processes like taking time off, or how the company can support individuals, or your expectations of their work, the easier the load will be for those affected.”

This philosophy extends to 1:1s, as well. If an ongoing manager/engineer relationship has succeeded in building trust and vulnerability, then both people can feel safe voicing when they can show up fully—and when they can’t. “There are times when you are not going to be a helpful, healthy person at work,” Hogan said. “I strive to build my relationships with my direct report in such a way that when I’m crumbling, I can tell them and it’s safe.”

Just as time spent preparing is necessary for a constructive 1:1, so time spent concluding pays similar dividends. Here are some considerations for ways to wrap up 1:1s that enable them to have their full impact:

• Ask open-ended questions before concluding. Questions such as “What did you want to talk about that we didn’t cover?” pave the way for ideas that didn’t make it onto the agenda—and these can often be what was most on the engineer’s mind all along.
  
  

• Schedule buffer time for each 1:1. If managers have to hustle their engineers out the door the moment a 1:1 ends because the next engineer is waiting in the hall, many productive conversations will be nipped just as it starts to blossom. Out of respect for their own time, managers can’t let every 1:1 run on willy-nilly all day long. But by leaving a small buffer on the calendar after each 1:1, powerful conversations will get the chance to resolve.
  
  

• Recap and discuss next steps. Taking notes allows managers and engineers to tackle the action items they’ve documented. As part of concluding a meeting, managers can confirm deadlines and clarify any actions. Do the engineers know what your next steps are? Do they know their own? Do you need to set milestones for larger action items?
  
  

• Document the meeting and share the notes. David Lynch, an engineering manager at Intercom, recommends sending notes after the meeting in order to crystalize and confirm both parties’ understanding of important takeaways, offer engineers the chance to clarify and ensure both people know what to expect next. Furthermore, followup communication affords engineers the chance to voice appreciation for their engineers’ candor, vulnerability and growth.

The time spent in a 1:1 may be only 30 or 45 or 90 minutes every week or two, but the responsibilities and the rapport are ongoing. The relationship of 1:1s is cyclical, and while a meeting might end, the true nature of the one-on-one never does. That’s the beauty of constructing healthy, ever-evolving, ever-growing 1:1s as essential components of a healthy, ever-evolving, ever-growing team.