I have a friend who dropped the most epic response during a job interview, and I still think about it years later.

He was interviewing at Raffles Institute for a role, and someone from the interview committee hit him with a tough question. His previous stint at NUS School of Medicine was short, so they pressed: “What will make you leave us?”

His response was legendary: “The day I leave Raffles Institute is the day I realize my boss doesn’t have the spine to make hard decisions.”

Mic drop. 🎤

That line has stuck with me because it captures something fundamental about leadership that most people dance around. We talk about “toxic bosses” and “bad management,” but we rarely cut to the heart of what makes a leader truly destructive: their complete inability to make the tough calls when it matters.

I was reminded of this recently during multiple discussions with a prospective company in the recruitment space. Their business was struggling - brand perception issues, evolving consumer needs, and a market that wasn’t doing them any favors. For the longest time, they’d been marketing in the B2C space, bringing on more candidates. But here’s the thing about job boards: candidates are just the bait. The real fish are the companies that pay for services through job ad credits.

They had a mandate to close certain accounts because big names were no longer using them. I suggested quick interventions such as networking sessions with Talent Acquisition teams, roundtables with heads of TA to get back in the game and show how they’d evolved from what they were a decade ago.

It took about two months to get back to me. The short answer? No. Their intervention? More brute force tactics that had already proven ineffective. As if their KPI was on amount saved, not revenue made.

Hard decisions avoided. Again.

Look, I get it. You’re probably reading this because you recognise the pattern. You’ve been there - waiting for direction that never comes, watching opportunities slip away because nobody wants to make the call, dealing with the chaos that comes from leadership that’s more concerned with looking good than actually leading.

The truth is, these aren’t just “challenging work environments.” They’re career killers. And once you know how to spot them, you can start making better choices about where you invest your time and energy.

Red Flags You Need to Watch For

Interview Red Flags

Experts say the biggest sign of a toxic boss is how they behave during interviews - “It’s their first impression, so they should be on their best behaviour.” If they’re already showing cracks, imagine what they’re like when nobody’s watching.

I have another friend who experienced this firsthand during an interview at an HR certification body. He was asked to prepare a presentation on what he would do to salvage a struggling product line. Reasonable request, right? Except during his presentation, the CEO constantly interrupted him with “this will not work,” “that will not work,” shooting down every single suggestion before he could even finish explaining his reasoning.

Think about that for a moment. They asked him to solve a problem, then made it impossible for him to present his solution. If this is how they treat someone they’re trying to impress during an interview, imagine how they handle dissenting opinions from actual employees.

Watch for interviewers who show up late, seem unprepared, dismiss your questions, or (like this CEO) ask for your input only to immediately shut it down. If they can’t respect your time or ideas during the courtship phase, what makes you think they’ll respect them when you’re actually working for them?

Decision Paralysis in Action

The chronically indecisive boss who can’t provide direction, leaving employees unsure of expectations, is a walking red flag. These are the leaders who need three committees to decide on office coffee, who demand endless data to avoid making any choice, who turn every decision into a six-month analysis project.

I know this intimately because I lived it at my former job. There was a committee for EVERYTHING. I’m not exaggerating - every single decision, no matter how trivial, had to go through some committee or another. The amount of time we spent prepping for these meetings, taking minutes, setting up all these feel-good gatherings that carried zero accountability was absolutely ridiculous.

It got so bad that I literally had to move a motion to shut one of these committees down during my time there. Think about that. I had to use the committee system to kill a committee because it was such a monumental waste of everyone’s time.

You know you’re dealing with this when projects die in committee rooms while competitors move ahead. It’s not caution. It’s cowardice dressed up as thoroughness. And while they’re analysing everything to death, your career is stagnating because nobody can make decisions about resources, promotions, or strategic direction.

Gut-Feel Decision Making (Ignoring Data Altogether)

On the flip side, you have leaders who swing to the opposite extreme - making major decisions based purely on gut instinct while completely ignoring available data. This isn’t intuitive leadership; it’s reckless ego masquerading as decisiveness.

These bosses will dismiss market research, ignore customer feedback, and override expert recommendations because they “have a feeling” about something. They’ll launch products nobody wants, pursue strategies that data clearly shows won’t work, and double down on personal hunches even when the numbers scream otherwise.

The irony? These leaders often pride themselves on being “decisive” and “action-oriented,” but they’re actually just as spineless as the committee-creators. They’re too afraid to face what the data might tell them, so they choose wilful ignorance instead of informed decision-making.

Both extremes (analysis paralysis and data-ignoring gut decisions) stem from the same fundamental weakness: the inability to make tough, informed choices when it matters most.

Blame-Shifting Behaviors

In toxic workplaces, mistakes quickly become grounds for blame, creating an atmosphere where everyone’s just looking to cover themselves. The spineless boss perfects this art form. They’ll take credit for wins and deflect responsibility for failures faster than you can say “quarterly review.”

These leaders create cultures where innovation dies because nobody wants to risk being the scapegoat for the next failed initiative. You’ll notice they’re mysteriously absent when tough conversations need to happen, but front and center when there’s recognition to be claimed.

The “Brute Force” Mentality

This is where my recruitment platform story becomes universal. How many bosses have you seen who, when faced with poor results, decide the solution is to do more of the same thing that’s already failing? They ignore expert advice, dismiss market feedback, and double down on strategies that haven’t worked in years.

It’s not persistence. It’s stubborn refusal to acknowledge reality. And you’re the one who has to execute these doomed strategies while they congratulate themselves on their “consistency.”

Why This Matters to YOUR Career

Here’s what nobody talks about: career stagnation under weak leadership isn’t just annoying. It’s career suicide. When your boss can’t make decisions about resources, promotions, or strategic direction, you’re not just working for a bad manager; you’re working in a dead-end situation.

You’re constantly second-guessing yourself, trying to read tea leaves about what your boss actually wants, and dealing with the chaos that comes from inconsistent direction. Meanwhile, your skills aren’t developing because there’s no clear path forward, no vision to work toward, and no leader willing to advocate for their team when it matters.

The personal stress is real too. You know something’s wrong, but you start wondering if maybe you’re the problem. Maybe you’re not understanding the “bigger picture.” Maybe you need to be more patient with the process.

Let me save you some time: you’re not crazy. If you’re seeing these patterns, trust your instincts.

What You Can Actually Do About It

Document the patterns. Not for HR complaints, but for your own clarity. When you can see the decision-avoidance pattern clearly, you stop taking it personally and start planning strategically.

Build relationships elsewhere. If your boss can’t provide direction, find mentors who can. Network with leaders in other departments or companies who actually know how to lead.

Develop your skills independently. Don’t wait for your boss to invest in your development. Take courses, attend conferences, build expertise that isn’t dependent on their approval or vision.

Plan your exit strategy. Not necessarily to leave immediately, but to have options when the inevitable happens. Because companies led by spineless leaders don’t just stagnate. They eventually collapse.

Set boundaries on your time and energy. Don’t let their inability to make decisions become your emergency. You can’t fix their leadership problems, but you can protect yourself from becoming collateral damage.

The Bottom Line

My friend’s interview response was brilliant because it identified the real problem: leaders who can’t lead. These aren’t just “difficult bosses” or “challenging work environments.” They’re career killers masquerading as management.

The good news? Once you can spot the red flags, you can avoid them. Even better, you can make strategic choices about your career that don’t depend on other people’s ability to make tough decisions.

Your time and talent are too valuable to waste on leaders who don’t have the spine to actually lead. Trust your instincts, document the patterns, and start building a career strategy that puts you in control.

If you prefer to stop depending on other people’s decision-making abilities, check out my book “No More Bosses” on Amazon. Because the only spine that matters is your own.

Have your own stories about spineless leadership? I’d love to hear them. The best way to deal with these situations is to learn from each other’s experiences.

🎧 Podcast

Join ​⁠Shawn Lim as he opens up about his transformative journey from being arrested as a teenager to becoming a successful content creator and podcaster.

Discover why he prefers the term 'content creator' over 'influencer' and learn about his platform, Human Algorithm, which aims to promote authenticity in the age of AI.

In this eye-opening podcast, Shawn shares deeply personal stories for his neurodiverse daughter and offers insights on how to navigate life's struggles while staying true to oneself.

Don't miss this compelling conversation filled with valuable lessons on vulnerability, authenticity, and the art of being human.

This episode is brought to you by Deel, the all-in-one platform simplifying global team management with payroll, HR, IT, and compliance solutions, trusted by over 35,000 businesses worldwide. Learn more at ⁠deel.com/adriantan⁠.

Adrian Tan
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