Summary: Around the world, leaders are tossing and turning, not because of poor mattresses, but because the weight of leadership in 2025 is heavier than ever. Here are the top issues robbing today’s leaders of sleep, and what to do about them.
Dear Dr. Sylvia,
I am the executive assistant to a highly creative and influential individual.
He has been showing up at the office with dark circles under his eyes and a slight slump in his shoulders.
I must admit, at first I wondered if he was having an affair, you know, Coldplay style.
I finally mentioned how tired he looked and asked if I could help.
With that, he started to talk (as if to himself) about tariffs, tensions, and troubles.
I would love some advice, or at least some ideas about how I can help him return to the bright-eyed individual I have worked with for the past five years.
Signed,
Curious Cathy
Top Leadership Concerns in Uncertain Times
Dear Curious Cathy,
I am delighted to hear your concern. It means you genuinely care about your boss and the work culture.
Let’s examine the challenges leaders are facing during this period of rapid change.
These sleepless nights aren’t just about hitting sales targets or pleasing shareholders. The modern leader faces a multitude of complex, interconnected, and relentless challenges.
Here are the top issues robbing today’s leaders of their sleep, along with some executive stress solutions.
The Talent Crisis: Finding, Keeping, and Inspiring People
The Great Resignation may have slowed, but the Great Restlessness is alive and kicking. Employees want flexibility, meaningful work, and leaders who walk the talk.
Why it’s a nightmare: Skilled people have options, and they’re not afraid to leave.
What helps: Build a culture where people feel seen, heard, and valued. That’s not HR-speaking, it’s a survival strategy.
Remember “Say What You Mean and Do What You Say”
Today’s workforce is more vigilant than in the past to hold leaders accountable.
As you stated in your question, consider the extreme worldwide response when the CEO of a company and the head of his HR team were caught on camera in a compromising hug.
Actions and words that align make a world of difference.
For example, recently, a coaching client of mine submitted his resignation to pursue a more promising career opportunity.
He was then counter-offered a step up to stay. The project manager promotion looked sizzling hot, and yes, he agreed to stay.
However, six months into the promise, it is not happening.
Lots more promises have tarnished his preference for the job.
As of this week, he submitted a non-negotiable resignation. In three weeks, he will be gone with the wind.
AI and Technological Whiplash
AI isn’t just a buzzword; it’s a business earthquake. The challenge isn’t just adopting new tech; it’s deciding which tech to adopt and how to keep teams (and ethics) in check.
Why it’s a nightmare: Move too slow, and you’re irrelevant. Move too fast, and you break things, sometimes trust.
What helps: Develop “tech fluency” in leadership, not just IT departments. Leaders who understand AI’s potential and pitfalls will sleep better.
Economic Volatility
Interest rates, inflation, and market swings are making strategic planning feel like a guessing game.
Why it’s a nightmare: The playbook from five years ago is now as useful as a floppy disk.
What helps: Focus on agility, shorter planning cycles, scenario mapping, and quick decision loops.
Burnout: Everyone’s Issue
Leaders aren’t just managing their teams’ stress; they’re drowning in their own.
Why it’s a nightmare: A burnt-out leader can’t inspire a thriving team.
What helps: Create systems that prioritize recovery as much as performance. No one wins when “running on empty” becomes the culture. More about this in my book Invisible Stress: It’s NOT What YOU Think.
Polarization and Conflict Management
Whether it’s politics, social issues, or generational divides, workplaces are microcosms of the larger societal tensions that exist.
Why it’s a nightmare: One poorly handled conversation can spiral into a PR disaster or a team implosion.
What helps: Invest in conflict resolution and communication skills. Leaders who navigate tension with grace gain loyalty and trust.
The “Invisible” Patterns That Keep Sabotaging Progress
This point is often ignored to the detriment of the entire organization. Many leaders don’t realize that the same behavioral patterns from their first family system, yes, the one they grew up in, show up in their organizations.
Why it’s a nightmare: Without awareness, leaders repeat old patterns that cause conflict, mistrust, and wasted time.
What helps: Learn to spot and complete these patterns before they repeat. (This is the heart of my work in Don’t Bring It To Work.)
The Real Sleeper Strategy: The truth? The leaders who sleep best aren’t the ones with the least challenges; they’re the ones with the most clarity.
Here’s the checklist for the new reality of leadership in 2025:
The talent crisis: Finding, keeping, and inspiring people.
AI whiplash: Move too slow, you’re irrelevant. Move too fast, and you break trust.
Economic volatility: Strategy now feels like guessing with better spreadsheets.
Polarization: Conflict management is no longer optional; it’s survival.
And the sneakiest one? Outdated, ingrained patterns showing up at work (yes, they do).
Here’s the truth:
The leaders who sleep best are those who know how to focus on what matters most and break the patterns that keep their teams stuck.
They know how to cut through the noise, focus on what matters most, and build trust in uncertain times.
The question isn’t “What’s keeping you up at night?”
The better question is: “What will you do about it tomorrow?”
To your success,
Sylvia Lafair
PS. Our coaches are available for a strategy session. Please email sylvia@ceoptions.com, and I will connect you with the perfect person.
