Most people are taught early in their careers to measure success by personal output. Ship faster, hit targets, stay visible, and opportunities will follow. That’s the implied bargain of the professional ladder: the harder and smarter you work, the better your trajectory. But in reality, your career path isn’t shaped solely by your own performance. It is equally shaped—sometimes more so—by the competence of the person managing you. If that manager knows how to unlock growth, shield you from chaos, and give you leverage within the organization, your impact compounds. If they can’t, no amount of individual effort will fully offset the drag. Yet very few workers make a deliberate habit of evaluating their managers. They take it on faith that leadership knows what it’s doing, or they focus so intently on their own performance that they never notice when the bottleneck isn’t them—it’s above them.
The absence of this evaluation creates a blind spot that can cost years. In a high-growth startup or scaling company, those years are often the most valuable, because the work you do and the skills you acquire during that window define your market value for the next decade. A weak manager can leave you spinning on low-impact tasks, blocked by organizational politics, or caught in constant reactivity that erodes your ability to build a clear portfolio of wins. The damage isn’t always obvious in the moment. You may feel busy, even overworked, and assume that pace equals progress. But there’s a difference between being fully occupied and actually advancing your capabilities or career prospects. The distinction often comes down to the systems your manager builds—or fails to build—around you.
The problem begins with how managers are often chosen in growth environments. Startups promote high-performing individual contributors into leadership roles without giving them any training in management. On paper, it makes sense. They know the product, they’ve shipped under pressure, they have credibility within the team. But leading isn’t just “more work” on top of what they’ve done before. It’s a fundamentally different operating system. It requires translating strategy into clear priorities, allocating resources where they will produce the highest return, removing blockers, and providing feedback that actually changes the way people work for the better. These are distinct skills, and without them, even the most capable former contributor can become a bottleneck. When that happens, the cracks show quickly: priorities shift constantly without explanation; the manager overcommits themselves to every meeting and decision, becoming a source of delays; feedback comes only during annual reviews, if at all; crises dictate the calendar rather than proactive planning.
For the person working under that manager, the effect is cumulative. Weeks spent waiting for direction turn into months without meaningful progress. Misaligned goals waste cycles on initiatives that leadership never actually backs. The team’s energy is consumed by putting out fires instead of building momentum. What’s more, these symptoms are often masked by false positive signals that convince you everything is fine. You may have a friendly rapport with your manager, which feels reassuring but doesn’t necessarily translate into career advancement. You might see them constantly busy and assume that busyness means they are effective leaders. Or you notice their proximity to influential people in the company and believe that influence will automatically benefit you. These indicators are comforting but misleading. They say little about whether your manager is creating the conditions for your growth.
Evaluating your manager is not about grading their personality or deciding whether you like them. It’s about collecting operational intelligence on a critical variable in your career: whether the person above you is amplifying your impact or quietly limiting it. To do that without getting pulled into politics or emotion, you need to focus on observable outcomes rather than subjective impressions. One way to think about this is through four key lenses: clarity, velocity, development, and leverage. Clarity asks whether you have a consistent understanding of how your work connects to the company’s objectives. Velocity looks at whether your manager removes blockers faster than they appear or creates new ones through indecision. Development measures whether you receive feedback that measurably improves your output and capabilities. Leverage examines whether your manager has the influence or operational capital to secure the resources, support, or cross-team cooperation you need to succeed. Run this assessment on a regular cadence—quarterly works well—because trends over time reveal more than isolated incidents.
The reason most people never run this kind of evaluation comes down to two barriers. The first is cultural. There’s an ingrained discomfort with the idea of “judging” your boss, as if doing so is disloyal or presumptuous. Many workers fear it will be interpreted as arrogance or subversion. The second is structural. Without a framework, evaluating a manager becomes an emotional exercise, reduced to “I like them” or “I don’t.” That kind of binary thinking isn’t useful for making strategic career decisions. A structured approach, anchored in tangible outputs like clarity and velocity, bypasses both barriers. It keeps the evaluation grounded in the actual results of your working relationship rather than feelings about the person’s style or personality.
Once you’ve made an honest assessment, you may find your manager is strong in most areas, and you’re in a high-leverage position to grow. But if you see consistent weakness in two or more of those lenses, you face a decision. You can compensate for the gaps by stepping into responsibilities they’re not handling. That might mean hunting down strategic context yourself if clarity is lacking, or building direct relationships with other teams if your manager struggles to get you resources. This approach keeps your performance strong but diverts energy from skill-building to gap-filling, which can be draining over time. You can also attempt to influence your manager upward, nudging them toward better behaviors by making it easier for them to do the right thing. That could involve bringing pre-framed decisions instead of open problems, suggesting regular check-ins to create a feedback rhythm, or packaging wins in a way that makes them look good to their own leaders. If neither compensation nor influence changes the trajectory after a defined period—two quarters is a reasonable limit—the third option is to exit and find a role under a stronger manager. Staying put out of misplaced loyalty or inertia is the career equivalent of letting a leaky pipe flood your house because you like the plumber.
This isn’t just an employee issue. If you are a founder or senior executive, the same diagnostic applies, only in reverse. Every weak manager in your organization is a bottleneck for multiple people. That bottleneck quietly erodes retention, creativity, and execution velocity. I’ve seen companies stall not because their product failed but because the middle management layer couldn’t translate strategy into consistent momentum. The founder saw interpersonal conflicts or missed targets as isolated events rather than as symptoms of systemic weakness in managerial capacity. When you evaluate managers in your organization, you’re not checking for charisma or culture fit—you’re measuring whether the people under them are shipping faster, learning faster, and gaining autonomy over time. If that’s not happening, you have an operational problem, not just a personnel one.
For workers, reframing the question from “Do I like my boss?” to “Am I more valuable to the market because of the last six months under this person?” changes everything. That shift makes it clear that evaluating your manager is not about personal grievance or office politics. It’s about operational due diligence. In a scaling company, the wrong manager doesn’t just slow you down; they create a compounding drag on your career trajectory. The cost isn’t just missed opportunities—it’s the erosion of your competitive edge in the market.
Evaluating your manager, then, becomes part of your career maintenance cycle, just like updating your portfolio or refreshing your skills. You’re not doing it to undermine anyone. You’re doing it to ensure you are positioned to grow in ways that align with your long-term goals. If the results are strong, you double down, knowing you’re in a system that works. If the results are weak, you take proactive steps—compensate, influence, or exit—before the damage compounds. And if you’re in a leadership position yourself, you use the same criteria to evaluate the managers you’ve appointed, because their effectiveness will multiply or diminish the entire organization’s output.
In the end, careers are built in systems. Some of those systems are designed by you, and some are designed by the people above you. The more you understand about how those systems operate, the better your chances of steering your career toward the outcomes you want. That’s why evaluating your manager isn’t a rebellious act—it’s a professional one. In fast-moving companies, loyalty to a failing manager isn’t a virtue; it’s an unnecessary constraint. The real loyalty should be to your own growth, your own capacity, and the systems that make both possible.
A company will always have more levers to pull than you can see from your desk. Strategy shifts, funding pressures, political alliances—these are currents you can’t fully control. But the relationship with your manager sits at the point where those currents hit your day-to-day work. If that point of contact is solid, you can navigate almost anything. If it’s weak, you’ll spend your energy compensating for turbulence you didn’t create and can’t fix from your position. That’s why the smartest operators treat evaluating their manager as non-negotiable. They run the diagnostic, they watch the trends, and they act before the system turns against them. Because in the calculus of a career, the person you work for is often the strongest multiplier—or the heaviest anchor—you’ll ever have.
WhatsApp
Instagram
Threads
