When we were kids, we feared monsters under our beds, missing dessert, or our parents seeing that we hadn’t cleaned our rooms.
No one cared about falling off their bike, scraping a knee, or making fun of themselves.
As adults, one of the scariest words is “failure” – and many of us avoid it at all costs. Have you ever tried something new, let’s say a sport, but when you weren’t great at it on the first try, you just quit? I sure have. Because failing, especially in public, feels unbearable.
But if we had acted this way as kids, we wouldn’t be able to write, walk, or even talk. A toddler falls a hundred times before grabbing a table and pulling themselves up to take the first step. So why are we so afraid to fall now that we're adults?
It usually stems from understandable – and very human – fears, like:
- We’re afraid of what others might think of us
- We feel embarrassed, vulnerable, and frustrated when things don’t click right away
- Or our inner critic charges at us the moment we aren’t perfect
But failing is an inevitable part of life. And it’s often the best way to learn. And nowhere is this more true than in management, where failing, every day, is practically part of the job.
The daily balancing act
Here’s the truth, I don’t think you can be a good manager without failing.
Not because you’re bad at your job, but because you're caught in constant contradictions. You can picture your responsibilities like a Venn diagram with three circles:
- Your team
- Your stakeholders
- And yourself
But the overlap in the middle is missing – because you’re constantly stretching, and something always ends up outside your reach.
Everyone has expectations of you, and inevitably, you’ll fail someone. There is no way to keep everybody happy all of the time. Trying to do so is a fruitless task.
Instead of resisting failure, it’s more helpful to recognize the patterns. Let’s look at how failure tends to show up in each direction.
1. Your team
Imagine this, your stakeholders push for new AI features in the app you’ve been building. They want it live within a quarter. But you know this isn’t plug-and-play – it’ll take time to make it genuinely useful, not just a flashy add-on.
You break the news to your team, telling them: “Hey, we’re doing this now. We don’t have a year or even six months. We need to deliver this in three.”
They’re frustrated. They’d rather work on something else, like improving the search experience – something they were excited about and already invested in.
To your team, it might feel like you failed them because you didn't advocate strongly enough. You’ve changed direction, taken away something they cared about, and replaced it with pressure.
But that's what you do in management. You don’t get to let your team chase a project forever. You set constraints. You balance autonomy and direction. Constraints are uncomfortable, but they’re also what turn ideas into deliverables.
You might always be the bad guy in somebody’s story that day. And you have to learn to live with that, without it stopping you from doing what’s necessary.
2. Your stakeholders
In general, most stakeholders push for:
- Increasing profits
- Reducing costs
- And developing new features to stay ahead of the competition
One way you can fail them is by pushing back too hard against their requests. Of course, you can push back a little for the sake of your team or if their requests are unreasonable, but you don’t want to cross a certain line where you become unprofitable.
For example, delivering new features a few months later might seem like a small thing. But it can have a butterfly effect. The company may not secure the next investment round, or users may start drifting to a competitor. There’s usually a reason they asked for something this quarter, not next.
Sometimes, leadership asks for things that just don’t line up with technical reality. Saying “no” outright can sound defensive or inflexible. But saying yes to everything risks setting your team up to fail – or burning them out in the process.
There’s a better middle ground. You might say: “We can’t deliver all of that by the end of the quarter – but we could start with X. Here’s what’s realistic. Here’s what we’d need to trade off.”
Proposing a phased implementation helps people stay grounded in reality without making them feel dismissed. You’re not rejecting their goals, you’re showing them how you’ll get there.
3. Yourself
When it comes to these three areas, failing yourself is the easiest.
Usually, managers do this by not paying attention to their own needs. They try to balance the team and stakeholders and end up paying the price themselves.
When pressure comes from both sides – stakeholders wanting more, and your team pushing back – it’s tempting to hold it together with brute force:
- You stop delegating
- You take on more work yourself
- You stay late to finish up work that no one sees
- You carry the emotional labor of the two other groups
- And you slowly start dropping your own needs
You tell yourself: “Just for this sprint. Just until we ship. Just until we hire a new person.” But, before long, you're exhausted, anxious, and unable to think clearly. Because you’ve spent all your time protecting everyone else and left nothing for yourself.
This kind of failure isn’t as obvious as a missed deadline. It’s more subtle and slowly creeps in. Which means it can be more dangerous.
It’s why learning how to fail can actually benefit you. Maybe you let a stakeholder feel a bit frustrated. Maybe your team doesn’t get their perfect roadmap. But you preserve your capacity to lead another day.
Get comfortable with failure
Not all failure is equal.
Some failures are just mistakes, like forgetting to follow up on an email. You learn, adjust, and move on. But other failures feel heavier:
- You say yes to too much
- You disappoint someone
- Or you drop the ball, not because you weren’t trying, but because the load was just too much
The difference isn’t always what happened. It’s how you carry it.
Getting comfortable with failure doesn’t mean becoming careless. It means learning which failures are part of the process, and which ones signal that something needs to change.
Sometimes, that comfort comes with time. Other times, it comes with perspective – knowing that a small failure now might be the very thing that keeps you from a bigger one later.
The more experience you gain, the better you get at choosing your trade-offs. And living with the consequences.
Short story: failure is inevitable, so use it to your advantage
As an engineering manager, you operate in constant tension between your team’s needs, stakeholders’ expectations, and your own capacity.
No matter how hard you try, you’ll fail in one of those areas, nearly every day. It’s not because you’re careless. But because it’s just the push and pull of the role.
Success in this role comes from getting comfortable with failure and learning to navigate the trade-offs that come with it. Instead of avoiding failure altogether, aim for balance:
- For your team: For example, say your team hates working on small, unexciting features. You ask them to work on them for a few months, but you give them space to recover with projects that light them up.
- Stakeholders: You fail your stakeholders slightly when you push back on timelines. But you trade that delay for long-term quality and sustainable delivery.
- For yourself: You fail yourself when you take on too much. But you learn to delegate, delegate, delegate! It’s the best antidote to failing yourself. And the best way to give your team ownership of their work. You don’t have to sacrifice your well-being just to have everything under control.
You’ll still cross the red line sometimes. We all do. The key is not to avoid failure altogether, but to fail in smaller, smarter ways – on purpose.
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Originally published on Medium.com