7 Signs You're About to Fail as a Leader

Read time: 6 minutes

Hey, welcome back.

Last week, we explored how feeling truly valued transforms our relationship with work and meaning.

​You can read that (and all past issues, here).

By the way, if you're finding these insights helpful, I've started collecting all these tools, resources, and one-sheets in the ever-growing 'Science of Success' vault. Check it out here for additional materials on today's topic and more.

Today, I want to dive into something that's been weighing on my mind lately:

The warning signs of leadership failure that we often ignore until it's too late.

The Invisible Crisis

Leadership failure rarely happens overnight. Like a slow gas leak, it's often odorless and invisible until something catastrophic happens.

I've learned this the hard way. In my first company, I didn't realize I was failing as a leader until half my team had mentally checked out and our growth had flatlined. The signs were there for months, but I wasn't paying attention.

What's most dangerous is that leadership failure doesn't announce itself with sirens and flashing lights. Instead, it whispers through subtle shifts in team dynamics, quiet disengagement, and the slow erosion of trust.

Let me walk you through the warning signs I've learned to recognize – both from my own failures and from working with countless founders through Heights and Secret Leaders.

1. The Silence That Speaks Volumes

When your best people stop challenging you, it's not harmony – it's hospice care for your team culture.

Think of healthy pushback like your organization's immune system. When it stops fighting, it's not because everything's perfect – it's because the body has given up.

I remember leading a meeting where I proposed a major strategic shift, and everyone just nodded along. Later, I discovered multiple team members had serious concerns but didn't feel safe expressing them. By the time I realized my mistake, we'd wasted three months and significant resources on a flawed direction.

The most dangerous feedback isn't negative – it's absent.

2. The Echo Chamber Effect

Yes-people aren't teammates; they're mirrors reflecting what you want to hear rather than what you need to know.

This happens subtly. You don't explicitly ask for agreement, but you unconsciously reward it while punishing dissent through your reactions. Soon, your team learns to tell you what makes you happy rather than what's true.

It's like developing an immunity to reality – comforting in the short term, but potentially fatal to your organization in the long run.

3. The Last to Know Syndrome

Suppose you're consistently surprised by problems that everyone else seems aware of. In that case, you've become informationally isolated – the leadership equivalent of being stranded on an island while your team watches from the mainland.

I once had a client whose team created an entire shadow communication system to work around him because bringing problems to his attention had become so unpleasant. By the time issues reached him, they had metastasized from manageable concerns into full-blown crises.

Information flows toward safety. If it's not flowing toward you, you've become unsafe.

4. The Talent Exodus (Visible and Invisible)

People don't leave bad jobs; they leave environments where they can't grow, contribute meaningfully, or feel valued.

The visible exodus is obvious – resignations and departures. But the invisible exodus happens first and is more damaging: your best people mentally check out while still showing up physically.

They're still at their desks, but their passion, creativity, and discretionary effort have already left the building.

Watch for the energy shift. When someone who used to light up during brainstorming sessions starts staring at their laptop, their body is present, but their spirit has already resigned.

5. The Activity-Results Disconnect

If your team is working harder than ever but accomplishing less, you're experiencing organizational friction – the leadership equivalent of a car engine overheating while barely moving forward.

This often happens when leaders confuse motion with progress. Meetings multiply, emails proliferate, projects expand – but meaningful outcomes diminish.

It's like watching someone furiously pedling a stationary bike and wondering why they're not getting anywhere. The energy expenditure is real, but the direction is missing.

6. The Optics Obsession

When you find yourself making decisions based on how they'll look rather than the impact they'll have, you've fallen into the appearance trap.

This manifests in various ways: elaborate presentations that mask weak strategies, performative leadership behaviours that don't translate to meaningful action, or decisions that prioritize short-term optics over long-term health.

It's like focusing on the packaging while ignoring the quality of what's inside – eventually, people open the box and discover the truth.

7. The Contagion of Burnout

Leadership burnout isn't just a personal issue; it's a communicable condition that spreads throughout your organization.

When you're exhausted and overwhelmed, you make poorer decisions, have less emotional bandwidth for your team, and unconsciously signal that unsustainable work patterns are expected.

Your team doesn't just observe your burnout – they inherit it.

I learned this lesson when a team member reflected back to me in her resignation: "I realized I was becoming as stressed and unhealthy as you appeared to be, and I didn't want that for my life." Her words hit me like a bucket of ice water.

The Deeper Truth

These seven warning signs share a common root: a disconnection between the leader and the human reality of their organization.

Leadership, at its core, isn't about strategy, vision, or execution – though these matter. It's about creating environments where people can bring their full humanity to work and channel it toward shared purpose.

When we fail as leaders, we're not usually failing at the technical aspects of leadership. We're failing at the human connection that makes the technical aspects work.

The Path Forward

If you recognized yourself in any of these warning signs, know that you're not alone. Every leader I respect has faced these challenges. What separates great leaders from failed ones isn't the absence of these issues – it's the courage to address them before they become terminal.

Here are three practices that have helped me turn around leadership failure:

1. Create psychological safety ruthlessly. Make it dramatically clear that honest feedback – especially uncomfortable truths – is not just welcome but essential. React to bad news with gratitude, not frustration.
2. Measure engagement, not just performance. Regularly ask, "How energized are you by our work?" alongside "Are you hitting your targets?" The first question predicts the future; the second only tells you about the past.
3. Make your self-care non-negotiable. Your physical, mental, and emotional health isn't selfish – it's a strategic priority for your organization. Leaders who sacrifice their well-being aren't martyrs; they're creating organizational liabilities.

A Question to Carry Forward

As you move into your week, I invite you to sit with this question:

Which of these warning signs resonates most deeply with your current leadership situation, and what single change might begin to address it?

Don't try to fix everything at once. Leadership renewal, like leadership failure, happens one step at a time.

Until Thursday,

Dan

P.S. If you're recognizing signs of leadership struggle, know that awareness is the hardest step. I'd love to hear which warning sign hit closest to home for you, and what you're considering doing about it.

SOS (Science of Success) Curated:

LinkedIn of the week: How to Reset Your Dopamine and Rewire Your Brain.​

Podcast of the week: Emergency debate on the future of the UK​

My Tweet of the week: The richest people in 2026 will be ordinary people who master one skill​

Military Leadership Principles Create Stronger Boards

A fascinating new study from Harvard has identified an unexpected source of accountability in corporate governance: military experience.

Researchers analysed 865 U.S.-listed manufacturing firms between 2010 and 2020 and found that boards with directors who have military backgrounds are significantly more decisive in addressing CEO underperformance, often making the tough call to dismiss underperforming CEOs when necessary.

The study reveals that many CEOs face little real accountability when their companies underperform, largely because they wield considerable influence over their boards. However, directors with military experience bring three crucial accountability principles to boardrooms:

1. Clear performance standards with measurable metrics
2. Regular, candid performance evaluations
3. Decisive action when standards aren't met

These military-derived principles create a framework for CEO accountability that transcends personal relationships and political considerations.

The implications are clear: regardless of whether your board includes veterans, implementing these military-inspired accountability practices could significantly strengthen leadership oversight and organizational performance.

This research underscores a critical truth about leadership: accountability isn't punishment—it's the foundation of excellence.

Is this the man who could end the global credit card crisis? In this explosive episode of Secret Leaders, we sit down with Philip Belamant, the visionary founder of Zilch — the UK fintech unicorn that’s rewriting the rules of credit, debt, and how we pay. Most people know Zilch as a "Buy Now, Pay Later" app — but it’s way more than that. It’s an interest-free payment model that flips the credit card industry on its head… all while quietly becoming 27x more effective than Google Ads. What we cover:

• Why credit card debt is a trap — and how Zilch is helping people escape it
• The shocking truth: The average UK citizen takes 16 years to pay off a credit card
• How Zilch funds 0% interest payments without hurting consumers
• The new payment system that could replace traditional credit
• What it takes to fight against billion-dollar legacy lenders
• Why Zilch's advertising model funds debt relief — and beats Google in the process
• The UK’s role in the global fintech revolution

Forget "boys don't cry" – discover what happens when men reject outdated stereotypes and embrace a more complete vision of leadership, fatherhood, and success.

​Listen now​

Until next week - smash your success,

Dan

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1-1 Coaching with Dan

In my goal to help more entrepreneurs/people who are looking to level up their careers, I've just started taking 1-1 consulting calls (only 1 a week)

Why book a call? Some of my expertise/success:

I've built 5 startups. 1 win, 1 fail, and 3 still going.

E-Commerce: Heights — with revenue over $15M a year.

Community: Foundrs, one of the UK's top founder communities

Podcasting: Leaders Media - bootstrapped media company that makes the UK's top business podcasts, Secret Leaders, with over 50M downloads.

Health/Mental Health: Managed to overcome burnout, insomnia, depression & anxiety in pursuit of success as I talk about in my interview with Steven Bartlett on Diary of a CEO​

Angel Investing: I've invested in over 90 startups

Coached & Mentored: Certified coach & done lots of mentoring

Personal Brand: Have grown to 178k on LinkedIn and X (Twitter) in the past 12 months

So if you're interested in booking a session with me to talk all things business or building a personal brand, book for 30-minutes or 45-minutes. (limited spots).

Science of Success Vault

I'm building a vault of valuable tools, resources, and one sheets that I hope help you succeed.

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Want to take your success (even more) seriously? 👇​
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