Eng folks — does this sound familiar? A high-performing engineer on the team moves into a management role (often with a not-so-gentle nudge from leadership). After all, the team is growing quickly, and someone needs to take the helm. Who better than someone who’s already proven their technical chops?
But, by Marcel Weekes’ estimation, at least half the time those newly-minted engineering managers will leave their post, retreating back to the IC sphere. “If this was the failure rate of a service, we would do a postmortem on it and be concerned that the failure rate was so high. But in this case, we tend to just shrug it off and say, ‘Engineering management wasn’t for them.’ We don’t dig in further,” he laments.
Even some of the highest-performing orgs can fall victim to this common tripwire. As the VP of Engineering at Figma (and previous VP of Eng at Slack) Weekes has risen in the ranks from EM to Director to VP. Along the way, he’s seen plenty of well-meaning engineering managers falter, and he’s on a mission to change the narrative.
“One of my goals is for us as an industry to better support people who are making the transition from IC to EM and get to a much higher success rate — because we need exceptional engineering managers.”
Before we dive into his playbook, let’s first start with his definition of exceptional people management: having different tools in your toolbelt, and knowing when to use them.
Exceptional managers know how to deal with situational differences. They don't bring a single hammer to every problem in front of them. They assess the situation and then they look to their toolkit — or go find new tools — in order to motivate and support that individual.
“A nuance that’s often glossed over is that when you're managing a team, you are both managing a group of people and the dynamics that come with that, but also individuals on the team. You may have senior tech leads on the team, junior people, someone who's going through a tough time personally, someone who's disengaged right now, or someone who's learning a new tech stack. And each one of those requires a different level of expectation, support, and encouragement,” says Weekes.
In this exclusive interview with Weekes, he unpacks some of the key reasons why the IC-to-manager transition is particularly fraught for engineers. Next, he shares tips crafted for startup leaders and new managers to dodge each of these common potholes. While Weekes’ advice is tuned towards the engineering side of the dial, there are plenty of pointers that will resonate with folks across the org chart. Let’s dive in.
WHY IS ENGINEERING MANAGEMENT SO HARD TO GET RIGHT? COMMON POTHOLES & SUGGESTED DETOURS
Problem #1: The best-suited folks aren’t being elevated to management.
Whether the company is opening up a net-new management role or backfilling an existing one, often the first place to start before posting on LinkedIn is looking within the walls of the company. And what better place to begin the search than the senior engineering folks who are consistently your top performers? Their code is crisp, their technical knowledge is deep. They will surely chart the right course for the rest of the team to follow.
It’s an understandable instinct, admits Weekes. “There’s some pragmatism around being able to hold a high technical bar for the rest of the team and effectively short-circuit technical decisions that the rest of the team may be making — getting to the right answer as quickly as possible,” he says.
But this ignores the fact that there’s a vast sea of differences between technical skill and people leadership.
If you ask world-class, top 1% engineering managers where they would’ve ranked themselves as an engineer, they’ll almost universally say that they were pretty good software engineers, but not great.
That’s not to say that there’s no advantage to up-leveling folks who are already intimately familiar with your tech stack and have subject-matter expertise about your product — but it shouldn’t be the only criterion. Not only will these technical wizards be increasingly dissatisfied as their calendars book up and they move further and further away from the code base, but they also may not have the wider array of management skills needed to excel in the role.
“An exceptional manager excels across multiple axes. The simplest definition is they make their team a lot more effective — and there’s so much that goes into that. They ensure their team has all the resources it needs to predictably deliver high-quality work. They’re a great recruiter and retain top talent. They’re adept at building cross-functional relationships with their design and product counterparts. And they give their teams very clear direction on what’s most important to the business,” says Weekes.
Solution: Comb through motivations, not just pedigree.
So rather than starting by evaluating the prospective manager’s code commits, begin with motivations — are they more energized by solving people problems or technical problems?
“If someone gets the most energy from solving really thorny technical challenges, you want to support them in going down that tech lead path. But if someone gets the most energy from helping a group of people do something they couldn’t have done separately, then that’s someone who has the right motivation to go into a management role,” says Weekes.
How do you use this barometer if the engineer hasn’t been in a people management role before? Look for opportunities where they might have tested the management waters. “If they’re at the point in their career where they’re being considered for a management role, they've probably had some level of interaction with a summer intern or with a new college grad who's been hired onto the team. Dig in here — ask how that experience went, what did they enjoy about it, what did they not enjoy about it, and what would they do differently the next time?” says Weekes.
“If you get someone who’s fairly reflective about helping onboard or up-level someone and their contributions to the process, then you have an engineer who is showing signs of wanting to move towards a people-oriented role.”
And a team member who rattles off a list of frustrations with the summer intern is a red flag. “Someone who doesn’t take much accountability in terms of what they could have done differently, or didn’t feel rewarded by the process, that’s an initial sign that this is not a role that would be motivating to them.”
Problem #2: New managers fall into a spiral that never pulls them out of IC work.
Particularly at startups, which are growing at a fast and furious clip, adding in a new manager class is often done somewhat under duress. A team isn’t moving as quickly as they used to — they’re missing deadlines, and prioritization seems to be a mess. It’s time to bring in some extra management support. “The way this often plays out is that someone who’s an IC on a high-performing team will be asked to be the manager because it’s growing quickly and the team needs additional support – and probably has needed it for a while,” says Weekes.
Oftentimes you’ll go from being a high-performing individual contributor on Friday to being a manager of 4-5 people on Monday, without much structure or support around you.
“Suddenly, people find themselves doing a new job that they haven't been trained for, don't necessarily have the skills for, and the company isn’t at the stage where it’s put together any formal training to help get them up to speed,” he says.
Enter what he ominously terms the “new manager death spiral.” “The team might start to fall a bit behind on a deadline. And the manager, who had been one of the highest-performing folks on the team, jumps in to help unblock. So they return to what they know best, and think that by writing code they can help the team get out of a ditch,” says Weekes.
Before you know it, you’re back to where you started. “At this point, the team is back to not having a full-time manager because that person is stretched so thin — they’re partly trying to manage, and partly trying to be an individual contributor. And they’re not doing either one all that well.”
To make matters worse, Weekes finds that engineering teams tend to face an extra burden here. “Within your typical startup EDP org, the bulk of the staffing is on the engineering front. So you end up with a situation where most first-time design managers or product managers or other functions might move into supporting one or two or three people initially. But for engineering managers, the first time they make that transition from IC, they’re often jumping into a team that’s five or six — maybe even eight people.”
Solution: Set new managers up with a bit of extra cushion.
Folks typically associate manager training with week-long snooze-worthy seminars and awkward role-playing exercises. While your startup may not be at the point where it has a robust, HR-led manager training program you’d see at a 60K employee company, that’s no excuse to throw folks into open water without a buoy to keep them afloat.
So try something lower-lift but still effective: setting new managers up with a management mentor. “I want to leverage the experience of the folks around me so I don’t have to make those same mistakes. It’s a super accelerant to someone’s evolution as a manager to learn from other managers who have tread the path before,” says Weekes.
If you don't have a learning structure in place, you're just asking new managers to make every mistake themselves for the first time.
“You need someone who you can talk to about, for example, the right way to approach a difficult performance review conversation. Literally just having that discussion with someone who’s done it before makes you 10x more effective the first time you do it,” says Weekes. “Without that, it can feel really lonely as a manager because you don't have a peer cohort or a group of people you can rely on. We’re just making it unnecessarily difficult for folks.”
New managers shouldn’t have to clear every single management hurdle all on their own — so pair folks with a mentor who can share their own hard-won wisdom and advice. “Having a growth mindset is important — but we shouldn’t be putting folks into a heightened stressful situation every single week without the right support around them. That’s a recipe for someone self-selecting out of the management path. Give them a sounding board.”
Here’s an example of one of his own hard-won bits of management advice that Weekes imparts on newer managers for one of the most common tripwires: doling out feedback. “When you ask folks what they’d like more from their manager, the answer is almost always they want more feedback. I read it in just about every performance review of a manager that I cover.”
But when you talk to managers, there’s a disconnect — they feel they’re constantly delivering feedback. “My hot take here is that when managers gear up to deliver feedback, they may think about it in the shower that day. They write it down and prepare to very deftly deliver it in a 1:1. But the person receiving it does not think that they got feedback or that it was constructive or actionable,” says Weekes. “The reality is that we’re never as explicit as we think we are.”
So time and time again, Weekes has learned to cut closer to the quick. “As a manager, it’s almost painful to say, ‘I have some direct feedback from you.’ It may seem pedantic or, at some level, contrived,” he says.
It’s critical that we are very clear about positioning feedback as feedback. I want my direct reports to be able to leave the 1:1 and point to an exact sentence where they received feedback.
“I think one of the major reasons managers don’t get this explicit is because hearing the phrase ‘I have some feedback for you’ causes some folks to get defensive right away. So instead, we weave the feedback in among other things and now it’s watered down. It’s born from a place of trying to make people feel comfortable, but it has a very different effect — it makes people feel unsatisfied.”
It’s a snippet of advice he’s shared over and over again with newer engineering managers he mentors. “Once people have done this a few times, it becomes much more comfortable. But there’s a huge activation energy to doing it the first time. New managers should recognize they're not in this by themselves. There are people you can lean on to help you through that first pass of doing your first difficult conversation of type X or Y.”
Problem #3: Managing former peers can be just plain awkward.
Let’s go back to the example that Weekes sketched out for us early on — you go from being a high-performer on the team, working closely with your peers to ship code, bash bugs and hit your deadlines. Suddenly, the switch flips, and these folks you were in the trenches with just yesterday are now the direct reports you’re supposed to be leading. You’re now the one setting the deadlines, maintaining a high bar and providing constructive feedback.
Let’s face it — it can get awkward, fast.
“I always advise people in those situations to recognize that the awkwardness does exist and that both parties are aware of it. It's not something that's just in the back of your head — it is actually a thing. And as with most relationships, it's best if you actually talk about that openly upfront,” says Weekes.
And don’t necessarily view managing former peers as a hindrance to your leadership growth. “One of the first things to do if you're managing a team of people new to you is invest a lot of time building those relationships. If you've already got those relationships, it may require some adjustment in terms of how you interact with folks, but at least you're starting from a strong foundation.”
And in many cases, the transition from folks viewing their former peer as a manager might be more seamless than you think. “In my experience, it actually feels most different for the person who stepped into that management role. When this is done well, that leadership has been signaled to the team for a while, even when that person was still an IC. They recognized this person as a de facto leader. In the past as peers, they might have gone out for coffee to ask for help on something. Now they’re getting feedback in a performance review. It’s a different venue, the stakes feel very different, but at its core, it’s the same type of communication.”
Solution: Don’t shy away from setting expectations.
One of the trickiest bits for new managers (especially folks managing their former peers) to get right is around expectation-setting — but this is perhaps one of the most paramount. “An effective manager is going to set a high bar in terms of what the expectation is. There’s a strong appetite for members of every team to know what is expected of them and how best they can help,” he says.
Every business is in some type of challenge. They're trying to grow, expand, survive — and everyone on the team gets up every day and they want to contribute to that success. But we need to know what the expectations are in order to deliver on those outcomes.
“When you're talking to new managers, this can feel like a totally different muscle. You're being really explicit with people who maybe were your peers not that long ago: ‘Here's what I need you to do,’ or ‘Here's what is expected of you.’”
Weekes advises a three-step process for getting it right:
- Step One: Set the rules of the road. “In the first couple of 1:1s start putting together a written document. How does the report like to receive feedback? Are there things that trigger them? What are the things they want to do more of? What are their ambitions? Where do they feel they need to be pushed?” says Weekes. “Whether it's someone who is your former peer and your friend, or someone who you just met, that helps set the table for how this relationship will go. Invest the time upfront.”
- Step Two: Open up the lines of communication. When it comes to setting expectations — for example, assigning a deadline for an upcoming project — always make it a two-way dialogue. “Ask your team: ‘Is this an aggressive but reasonable goal? Is this something we can land?’ And it almost doesn't matter if the answer is yes or no, because what you're doing is opening up the space to have a further dialogue about it and dig in more. There should be a healthy tension with how much you want the team to stretch — if you're hitting your goals 80% or 90% of the time, in my estimation, that's probably too much. It's probably the case that you've not set them aggressively enough. And it's really important that managers have a direct conversation with their team because it's not going to be the last time that you're setting expectations and you'll want to get sort of more aligned every time you do it,” says Weekes.
- Step Three: Evaluate success by being a reporter. With the expectations set, the guidelines are in place to evaluate the team’s performance. Weekes has a particular approach here. “This is something that feels very different to new managers. I try to encourage them to look at this not as judging people, but rather as being the reporter of facts and presenting a mirror to people so that they can see how they executed. Provide as much fact-based evidence as you can to people about how they performed relative to expectations, and also be really clear about what the next set of expectations are.”
One last bit of advice Weekes imparts to new managers when it comes to setting expectations — allow space for bottoms-up exploration. “The best goal setting is around setting the right metrics to track, and then empowering the team to figure out the right levers to pull. It isn’t leadership telling the team, ‘This is how to do it.’ It’s leadership telling the team, ‘This is what's important and this is how you'll measure it. How you get there is within your purview.’”
When teams feel like they’re ticket-takers and follow a specific directive of how to build out a feature, you see it in the way the product is built. But if you localize the decision-making and feedback loop at the team level, knowing that you're aligned with the outcomes, you can iterate much more quickly.
WRAPPING UP: DON’T LET PROMO TRACKS GET FOLKS INTO MANAGEMENT FOR THE “WRONG REASONS”
To borrow a reality dating show trope, are folks venturing down the management path for the right or the wrong reasons? “That may not even be on them,” reminds Weekes. “It may be the structure of the company they operate within. In order to get a pay increase or to be recognized and valued by the company, they need to be on the management track.”
And so, despite being much more at home with their noise-canceling headphones on coding away uninterrupted, folks agree to take on a management role with their sights set on a pay bump and greater influence. Top of the list of these new manager complaints? Their calendar looks wildly different.
One of the biggest things that a lot of first-time managers talk about is losing control of their own calendar. All of a sudden, your day-to-day is run by a calendar instead of pull requests or feature tickets.
“Oftentimes as an IC you've got a couple meetings a day and you can slot in blocks of time where you get to do heads-down coding and cranking on the work that you really enjoy doing. But as a manager, meetings are the currency of the realm. You spend a lot of time as an information broker, getting information, disseminating information, making decisions — and that happens in meetings,” says Weekes.
So be very candid with folks considering the manager path about the challenges of the role and what they’re giving up — it might just save the whole team a world of headaches. “Ultimately, management is a hard job and not without challenges. So if you get into it for the wrong reasons and you’re not motivated by the problems you need to solve, the difficulty of the job will increase exponentially.”
To go back to the kernel of the problem here, folks (often rightly) assume that in order to grow their influence and their career at a company, their value is measured in their number of direct reports. As a company, it’s vital to carve out career tracks for folks who want to be deep-diving ICs and technical subject matter experts, without devoting their time to solving people problems. So, for starters, consider how you’re rewarding people on each track, with ladder rungs and promotion tracks that don’t rely on building out a team.
And disseminate decision-making across the team — not just concentrated (and thus, bottlenecked) at the engineering manager level. “You want the manager setting up the frameworks and processes and the environment in which people can make decisions as close to the problem as possible. And in that case, you’ll have senior engineers across the board making decisions,” says Weekes.
That doesn’t mean these decisions happen without review. “But a high-performing technical leader (not just a people leader) can be providing that review layer as well. Chances are, they will be more engaged and happy in their role if they aren’t dealing with some of the things that they consider the ‘people manager tax.’"