The Painful Truth About Management: What They Don't Tell You in Leadership Books

You thought management would be about vision boards and strategic planning. Maybe some inspiring one-on-ones where you'd mentor brilliant engineers toward career breakthroughs. You pictured yourself as the calm orchestrator, making thoughtful decisions while your team executed flawlessly.

Then you got promoted.

Now you're debugging people instead of code. Your calendar looks like a distributed denial-of-service attack. And that production outage at 2 AM? It's your phone that rings first, even though you haven't touched the deployment pipeline in months.

Welcome to the reality of management in the tech industry. It’s messier than your worst legacy codebase, more unpredictable than JavaScript, and twice as likely to keep you up at night. In my work at Kendoo, where I help startups and engineering teams through software development consulting and technology leadership mentoring, I encounter these realities every day. Here's what they don't tell you in those glossy leadership books.

Not Everyone Will Like Your Decisions

You finally get budget approval for two new hires. The team has been pushing for more resources for months. You'd expect a celebration, right?

Wrong.

The backend team wanted senior engineers. The frontend team lobbied for junior developers they could mentor. DevOps wanted site reliability engineers. Everyone had opinions about the hiring bar, the interview process, and whether to prioritize domain expertise or cultural fit.

You make the call: one mid-level full-stack developer and one senior backend engineer. Backend is cautiously optimistic. Frontend feels ignored. DevOps thinks you don't understand the infrastructure challenges.

As a manager, every choice you make affects people. Some will disagree, some will be frustrated. It's part of the role. You can't expect everyone to support every move.

You can't optimize for everyone's happiness function simultaneously. The sooner you accept this, the sooner you can focus on making decisions that serve the broader mission, not individual preferences.

This is precisely why I guide clients in startup tech strategy and engineering leadership consulting, helping them align tough decisions with business goals while keeping teams motivated.

Boundaries Are with Many People

You thought setting boundaries would be about managing down and telling people no when they ask for impossible deadlines or scope creep. But boundaries flow in all directions.

Your VP wants daily updates on the microservices migration. Your product manager keeps pulling developers into "quick" meetings without notice. Your peer in the data team keeps requesting engineering cycles for their pet project. Your direct reports expect you to shield them from all organizational chaos while somehow keeping them informed of relevant changes.

You're a firewall, rate limiter, and load balancer all at once. And sometimes you have to drop packets.

You'll need to set limits not only with employees, but also with your own managers, clients, and stakeholders. Boundaries are part of leadership, and they must be clear before they're crossed.

Learning to say "no" upward is more complicated than saying it downward. Your manager has power over your career. But protecting your team's focus is part of the job. It's not about being difficult; it's about being strategic with everyone's most precious resource: attention.

In my work with clients at Kendoo, we often focus on building effective tech teams by learning to protect attention, improve engineering processes, and maintain clarity across stakeholders.

Learn to Live with Guilt

When I mentor tech leads and managers, I remind them that guilt is not weakness; it’s the weight of responsibility. Learning to carry it is part of growing into leadership.

Imagine that budget cuts were decided by leadership, resulting in a 20% reduction across the engineering department. You spent weeks analyzing team composition, project priorities, and individual contributions. You made spreadsheets. You lost sleep. You crafted the most thoughtful, data-driven decision possible.

Lisa had to go.

She was a solid contributor, but junior compared to others. Her projects weren't on the critical path. The math was straightforward. But she was also supporting her parents, had just bought a house, and loved working on the team.

You made the correct business decision. You followed the process. You provided generous severance and helped with job placement. You did everything by the book.

And you still feel sick about it.

Some decisions will never feel entirely fair. Someone will end up paying the price. The guilt doesn't disappear; you learn to carry it as part of the job.

Management involves making decisions with incomplete information that affect the lives of real people. Sometimes there is no entirely fair choice. The guilt doesn't go away. You learn to carry it. To let it inform future decisions without paralyzing you.

Don’t Try to Avoid Conflicts

Two of your best engineers disagree fundamentally about the architecture for a critical new service. Jake wants microservices. Scalable, maintainable, future-proof. Maria wants a monolith. Simpler, faster to build, easier to debug.

Both are right. Both are wrong.

Your first instinct might be to find a compromise. Split the difference. Keep everyone happy. But compromise often leads to the worst of both worlds: a distributed monolith that's neither scalable nor simple.

Instead, you facilitate the conflict. Create space for both sides to present their cases. Ask challenging questions about timelines, team skills, and long-term maintenance. Let the tension surface the real trade-offs.

Conflicting interests are everywhere in management. Trying to keep constant harmony often just postpones the clash and makes it harder when it finally comes.

Good decisions often emerge from productive conflict, not from avoiding it. Your job isn't to prevent disagreements; it's to ensure they happen constructively and lead to clarity.

Your Success Is Seen in the Team

Remember when bugs were logical? Input A plus condition B equals predictable crash C. Your GitHub contributions are now flat lines. Your last meaningful commit was three months ago. That algorithm you've been wanting to optimize? Someone else will have to do it.

This hit me during a quarterly review when I realized I couldn't point to a single feature I'd built. Instead, I was talking about team velocity improvements and reduced on-call incidents. My manager nodded approvingly, but part of me felt like a fraud.

Your achievements will be judged by what the team delivers. The real challenge is not doing everything yourself, but guiding others to succeed.

Your individual contributions become invisible. The features you used to ship? Now you're measured by what eight other people deliver. That quick fix you could have coded in an hour? You have to wait for someone else to prioritize it, understand it, and implement it their way.

It's scaling yourself horizontally, rather than vertically. And it's harder to measure.

When There's a Problem, It's on You

Your team ships a new feature. It passes testing, but once it reaches production, users start reporting unexpected issues. Tom, the engineer who built it, can’t reproduce the problem. Real usage patterns don’t behave like the test scenarios.

Here’s the painful truth about management: fault and responsibility are not the same thing. Tom may have missed something in his implementation, but you approved the design, the testing plan, and the release strategy. You didn’t catch that the testing scenarios weren’t comprehensive enough.

It doesn’t matter who introduced the bug. As a manager, you are accountable. You’re the one who must handle it, stand by it, and own the outcome.

The review will focus on improving the process, not assigning blame. But when leadership asks what went wrong, you’re the one explaining it. When users complain, you’re responsible for delivering the fix. The responsibility always flows upward, even when the work flows down.

That’s the kind of moment I often unpack with the startups and engineering managers I work with at Kendoo, not as theory, but as lived reality. These aren’t abstract leadership lessons; they’re situations that shape how teams grow, how processes evolve, and how managers become leaders.

Where Your Real Impact Shows Up

The truth is, management changes what impact looks like. You stop counting commits and start noticing how decisions ripple through people. Sometimes it feels invisible, sometimes it feels thankless, but it always scales far beyond what you could do alone.

I observe this shift frequently when working with teams and managers at Kendoo. They expect tools or frameworks, but what really matters is learning to carry the responsibility, make the hard calls, and create space where others can do their best work.

It’s not about glossy leadership theories. It’s about the messy, late-night moments when you realize your job is no longer fixing the bug yourself, but making sure the team has what it takes to fix it better tomorrow.

That’s the multiplier. That’s the work.