Advice is scarce, and opening up feels risky.
When I first became a CEO, I was thrilled at the prospect of leading a company, making big decisions, and guiding my team toward success. But something I didn’t expect was the crushing loneliness that came with the role. Suddenly, every tough decision, every setback, every moment of self-doubt felt like it was mine to bear alone. I had no peers to turn to, no space to vent, and no real outlet to process the pressures of leadership.
I remember one particular day when I had to make a difficult decision to run a redundancy program, and to let go a number of people, some of whom had been with the company from the start. It weighed heavily on me. While the decision was the right one for the business, it felt personal, and I had no one to talk to about the emotional toll it was taking. How could I open up to my team about this? They relied on me to stay composed and confident. As much as I wanted to, I couldn’t talk to my board about it either – what if they saw it as a sign of weakness? So, I kept it to myself, as I had with so many other challenges.
This is the reality for so many CEOs. Vulnerability feels like a liability. We avoid sharing our struggles, sidestep hard conversations, and carry the weight of the job in silence. But here’s the truth: isolation doesn’t make us stronger leaders – it just erodes our ability to lead effectively.
That’s why I’m launching this daily series: 100 CEO Challenges. Each post will highlight one of the many trials we face as leaders, most drawn from my own experiences. My hope is to break down the walls we’ve built around ourselves and create a space for honest conversations. Because no matter how alone we feel, we’re not the only ones navigating these struggles.
Does today’s challenge resonate with you? Have you felt the sting of isolation as a leader? Share your thoughts in the comments, or if you’d like to talk privately, feel free to DM me.
And if you’re ready to reflect on your journey – or explore how Purple Infinity, in partnership with Vistage, can help you find the support and guidance you need – reach out anytime. Together, we can tackle these challenges head-on…
The CEO alone bears the weight of being the ultimate responsibility owner for decisions and outcomes.
And some decisions can be incredibly difficult.
In my first CEO role, I led a satellite company operating two spacecraft that covered two-thirds of the planet. Tucked away among the sand dunes of the Arabian desert stood our state-of-the- art satellite control center. One day, I got called to get there urgently, as disaster had struck. Our primary satellite, responsible for roughly 80% of our revenue, lost its pointing. In plain terms, it was no longer facing the right direction, triggering a 55-hour outage and a very real risk of losing it forever.
We attempted several lower-risk recovery methods. All failed. We attempted several lower-risk recovery methods. All failed. The next option was to try an elaborate maneuver that was deemed to be a high-risk one: success would restore control and consequently mission-critical services; failure could mean losing the satellite altogether or extending the outage, deepening the strain on the business. Boeing, our supplier, and my exceptional team carefully laid out scenarios and probabilities. The Board offered moral support. But the ultimate “go/no-go” call rested with me alone.
Making that call meant digesting enormous amounts of technical data, weighing probabilities, reading the human dynamics, emotions, and psyche behind the recommendations, and managing the psychological pressure on the team. It was neither simple nor comfortable, but leadership demands decisive action.
I said “go.” We succeeded. The story ends well.
Does today’s challenge resonate with you? Do you feel the weight of having to make the right calls? Share your thoughts in the comments, or if you’d like to talk privately, feel free to DM me.
And if you’re ready to reflect on your journey – or explore how Purple Infinity, in partnership with Vistage, can help you find the support and guidance you need – reach out anytime. Together, we can tackle these challenges head-on…
CEO spends considerable time and effort aligning team members and different stakeholders.
As a CEO, have you ever felt like your main job was simply translating and relaying messages between team members? You find yourself asking:
1) “Have you checked in with Joe about this?”
2) “Did you call Melissa to confirm?”
3) “Can you and Frank work it out and only loop me in if you can’t agree?”
I wasn’t leading strategy or solving high-stakes problems – I was acting as a human switchboard, passing messages between people who could have spoken directly to each other.
The frustration wasn’t just the time it took. It was the extra mental cycles spent on work that shouldn’t have landed on my desk in the first place. Talented people were relying on me to align them when they should have been aligning themselves.
It made me ask: Why does this happen? What stops smart, capable teammates from having the conversations they need, in full and without hesitation?
Every company talks about values, and many work hard to define a handful that capture their culture and vision. If I could only pick one for my teams, it would be alignment. Without it, execution slows, tensions rise, and the CEO becomes a bottleneck. With it, teams move faster, make better decisions, and the CEO can focus on the work that truly matters.
Does today’s challenge strike a chord? Drop a comment or send me a message.
Ready to tackle your own challenges head-on? Let’s talk about how Purple Infinity, in partnership with Vistage, can help you navigate with clarity and confidence.
CEO struggles to switch off the “CEO mode” when leaving the office and getting home.
I won’t say too much on this one – for obvious reasons. Let’s just say you’ll know it’s happening when a familiar voice at home reminds you: “You’re not the CEO here!”.
Does today’s challenge strike a chord? Drop a comment or send me a message.
Ready to tackle your own challenges head-on? Let’s talk about how Purple Infinity, in partnership with Vistage, can help you navigate with clarity and confidence.
CEO may be the only one who understands that resources are limited and need to be allocated across competing priorities.
The joy of budget season... As CEO, one of the most valuable instincts you develop is the ability to sniff out the “fudge factor” in budget requests. Every year, the ritual repeats: department heads ask for more; more resources, more headcount, more share of the pie. The problem? That pie isn’t getting any bigger. Every extra slice for one team means a smaller one for another, yet somehow, no matter how senior the leader is, this reality rarely registers.
Your job is to see the big picture: to decide what’s reasonable, set priorities, allocate fairly, and still secure buy-in from those whose requests will inevitably be trimmed.
Sometimes, though, you have to go full detective – digging into the numbers, probing the real reasons behind inflated asks. Often, it’s not malice, but inefficiency: a team structure that bleeds resources, or a leader avoiding tough performance conversations.
And there you are again, knee-deep in the weeds, working in the business when you’d much rather be working on it.
Does today’s challenge resonate with you? Do you feel the weight of having to make the right calls? Share your thoughts in the comments, or if you’d like to talk privately, feel free to DM me.
And if you’re ready to reflect on your journey – or explore how Purple Infinity, in partnership with Vistage, can help you find the support and guidance you need – reach out anytime. Together, we can tackle these challenges head-on…
At times, the CEO seems to be only one with a high level of ownership, only one to turn off lights before leaving office.
Ever feel like you’re the only one who truly cares?
The one who slides chairs back into place after a meeting… picks up and secures confidential documents left behind… or turns off the lights at night so energy isn’t wasted?
If you own the business, that may come with the territory. But if you’re a hired CEO, just like your colleagues are hired executives, why does it so often feel like you’re the only one carrying the mantle of ownership?
Is it fair to equate small lapses (like not tidying up or forgetting the details) with a deeper lack of engagement? Or do these little things point to a larger gap in how connected the team feels to the company’s purpose?
The real challenge isn’t just frustration over these small moments; it’s figuring out how to instill a true sense of ownership across the team, a key to elevating performance. How do you help people care for the business as if it were theirs?
Does today’s challenge strike a chord? Drop a comment or send me a message.
Ready to tackle your own challenges head-on? Let’s talk about how Purple Infinity, in partnership with Vistage, can help you navigate with clarity and confidence.
Fundraising is one of the most demanding tests of a CEO – emotionally, mentally, and physically.
At some point, nearly every CEO will face it. Whether it’s raising capital to keep the lights on or scaling the business to the next level, road shows become unavoidable. The pace is grueling: back-to-back presentations, endless Q&A, difficult negotiations, and the constant pressure to deliver a flawless performance.
On these stages, there’s no hiding. The CEO is the show. You’re expected to read the room, catch subtle cues, deliver the right messages, and negotiate a favorable outcome. The stakes couldn’t be higher, and there’s no room for error. The CEO’s performance has to be at its best.
I remember one road show where the investor consisted of a consortium of seven companies and banks. My three-person team and I faced an audience of around seventy decision-makers and influencers. Every question, every challenge, every objection had to be answered convincingly, and ultimately, it fell on me to steer and deliver the outcome.
Your team’s support matters, but the weight of success rests squarely on the CEO’s shoulders. That means you need to show up as more than a leader: you must be an excellent presenter, a great listener, a top salesperson, a strategist, a negotiator, and have the confidence and the stamina to repeat for hours and days, and with numerous investors, until the money is raised.
Does today’s challenge resonate with you? Do you feel the weight of having to make the right calls? Share your thoughts in the comments, or if you’d like to talk privately, feel free to DM me.
And if you’re ready to reflect on your journey – or explore how Purple Infinity, in partnership with Vistage, can help you find the support and guidance you need – reach out anytime. Together, we can tackle these challenges head-on…
The CEO has to navigate and manage the occasional and expected public relations crisis.
At some point, nearly every CEO will face it. Whether it’s raising capital to keep the lights on or Every CEO, sooner or later, will face a public relations crisis. It’s not a matter of if, it’s a matter of when.
Marketing may manage the details, but the responsibility – the decisions, the tone, the credibility – falls squarely on the CEO. And often, the CEO must become the chief spokesperson. (Unless, of course, the CEO is the crisis – as we saw recently with that infamous rock concert incident.)
In my first CEO role, very early in my tenure, I got a call that tested this reality. It was the Editor- in-Chief of a major global television news outlet. No team around me. No Board. No communications experts. Just me, my phone, and the weight of my company’s reputation.
Here’s how the conversation went:
Man: “Hello, can I speak to Samer Halawi? The CEO?”
Me: “Speaking.”
Man: “I am the editor-in-chief for [xxx]. I am calling to let you know that we are going to go on
the air in an hour and mention that your company is affiliated with the [yyy] regime.”
Me: “Why are you saying that?”
Man: “I know you are because the communications equipment that your company supplies us is
not working over that country.”
Me (thinking quickly): “Oh I see, well are you calling me as a customer or as a journalist?”
Man: “Why does it matter??”
Me: “Cause if you’re calling as a customer, I will have to transfer you to customer care.”
Man (groaning): “I am calling you right now as a journalist who wants to know what’s going on.”
Me: “Fair enough. The reason your equipment is not working is not because we are in any way affiliated with any government, but rather because that government is interfering with our signal,
and it’s affecting the network, and a complete outage in that area…..”
Man: “Well I am not buying that. I will go on the air anyway and stick to my story.”
Me: “I hope you don’t. If you do, I will have to go myself on the air on your competitor’s network
and explain why your story is completely flawed.”
As soon as I hung up, I knew our prior strategy of avoiding public discussion was no longer viable. We had to confront it, and fast. Within minutes, I called a friend (the editor-in-chief of the competing network), secured a live slot, rushed to the studio, and went on air before the first outlet could run their piece.
There, I explained the facts: we were the target of an interference attack, and we were urging the relevant authorities to help us restore our mission-critical services that saved and improved lives.
If you’re a CEO, your crisis moment will come. The only question is: will you be ready to handle it?
Does today’s challenge strike a chord? Drop a comment or send me a message. Ready to tackle your own challenges head-on? Let’s talk about how Purple Infinity, in partnership with Vistage, can help you navigate with clarity and confidence.
Being at the top is not only lonely but also deprives the CEO of the natural workplace camaraderie.
In my junior year of high school, I enrolled in a double program, taking on the French curriculum alongside the national coursework. It meant moving into a new class with the school’s top students and nearly doubling my workload. But the hardest part wasn’t the extra work. It was looking out the window, watching my friends (who did not enroll in that additional program) laugh and play on the playground, while I sat inside alone, wrestling with new challenges.
Years later, when I became a CEO, I realized that “lonely at the top” feels much the same. It’s not only that you can’t always share what’s on your mind with your team or your Board – it’s also that, as CEO, you stand apart. Where others can lean on peers, form camaraderie, and bond freely, you must maintain a certain distance. It felt like being back in that classroom, watching from the window.
As CEO, you are always being observed, judged, and emulated. You carry the persona of the CEO wherever you go, often at the expense of your own lighter side – the instinct to joke, to relax, to simply be yourself. The role can strip away the fun of day-to-day connections with colleagues you genuinely enjoy. While others might share a laugh in meetings or head for drinks after work, you hold back. That freedom – the simple luxury of belonging – becomes one of the heaviest costs of leadership.
Does today’s challenge resonate with you? Do you feel the weight of having to make the right calls? Share your thoughts in the comments, or if you’d like to talk privately, feel free to DM me.
And if you’re ready to reflect on your journey – or explore how Purple Infinity, in partnership with Vistage, can help you find the support and guidance you need – reach out anytime. Together, we can tackle these challenges head-on…
For any CEO, few responsibilities feel heavier than letting people go.
“You are fired.” Those three words carry such a negative connotation. You first get exposed to them in movies perhaps, sometimes they are whispered at home, or with friends, and when you join the workforce, there’s a chance you’ve witnessed or experienced them directly. At some point in your career, if you rise to senior leadership, you move from hearing those words to having to say them.
Firing is never easy. It’s painful to hear, and often even harder to say. Why? Because you know firsthand the sting it leaves – and that awareness triggers one of the most powerful emotions a leader can feel: guilt.
But as CEO, you can’t lead solely from emotion. You must separate empathy from necessity, balancing compassion with the logic of what’s best for the company and its broader community. Shareholders, employees who remain, and the long-term survival of the organization depend on those decisions.
Otherwise, you would simply not be fulfilling the responsibilities entrusted upon you by the shareholders.
What makes it even harder is when the people you must let go are good, kind, hardworking individuals, parents with families to feed, or colleagues who may struggle to find another role. That’s when the weight feels heaviest. Yet leadership demands that you face it head-on, accept the responsibility, and execute with clarity and fairness.
Terminations will never stop being painful. But to do the job well, a CEO must find the discipline to carry that weight without being crushed by it.
Does today’s challenge strike a chord? Drop a comment or send me a message. Ready to tackle your own challenges head-on? Let’s talk about how Purple Infinity, in partnership with Vistage, can help you navigate with clarity and confidence.
Being CEO means managing not only down but also up — and the stakes couldn’t be higher.
The Board of Directors holds the ultimate authority: approving critical decisions, determining executive compensation, and even deciding your continuity as CEO. Success depends on building the right relationship with the Board – a balancing act of sometimes competing priorities. On one hand, you must keep them informed; on the other, you can’t let Board prep consume all your time. You must enforce governance, align the Board with your leadership team, and ensure that approvals are processed quickly. That requires bulletproof proposals – crafted with an owner’s mindset –that leave little room for rejection. I always told my team that our KPI for a successful Board meeting is one where 100% of our proposals are accepted. Anything less falls on our shoulders.
And then there’s the human factor: personalities and dynamics that make every Board unique. In my first CEO role, I had 11 highly accomplished directors. Their mutual respect was so strong that no one wanted to disagree, which stalled decision-making. Navigating that required careful orchestration to drive consensus. In another role, each director came with very different motivations, making alignment across the Board, and with the management team, extremely challenging.
Does this challenge resonate with you? Do you feel the weight of managing the Board while making the right calls for your business? Share your thoughts in the comments, or DM me if you’d prefer a private conversation.
And if you’re ready to reflect on your journey, or explore how Purple Infinity, in partnership with Vistage, can help you find the support and perspective you need, reach out anytime. Together, we’ll tackle these challenges head-on.
Every CEO will face tough supplier situations more than once, and they often require decisive, value-driven calls.
Early in my first CEO assignment, I had to confront onehead-on. We were counting on a supplier to deliver a satellite terminal thatwould launch our maritime business. The market was ready, the company was inturnaround mode, and we urgently needed revenue.
But when I joined, I discovered the supplier had skipped keytesting and the product didn’t meet specifications. I had to make a hard callto reject their push to launch, despite the delay it caused us.
Months later, when the terminal was finally market-ready,their CEO called me in. Instead of celebrating, he delivered an ultimatum: theywould only launch if we paid them more cash up front. He knew how badly weneeded this product and tried to strong-arm us.
I listened carefully, explored alternatives, and evenoffered them a share of service revenues; a win-win tied to performance. Herefused. He only wanted immediate payment.
At that moment, it wasn’t just a financial decision, it was a moral one. This was not a partner we could trust. No matter how desperate we were, I couldn’t let the company be held hostage. So, I surprised him, stood up, and walked away.
That very day, we engaged another supplier—one with a very different culture—and struck a deal to accelerate development of an alternative product, with more upside for them based on speed to market.
In the end, the first supplier’s gamble backfired. They were left with warehouses full of useless inventory. Their short-term greed cost them the long-term relationship. Meanwhile, our company gained a partner aligned with our values, and our team gained clarity about the kind of culture we wanted to build.
The lesson? Doing the right thing may feel costly in the moment, but it pays off in trust, culture, and resilience.
Does today’s challenge strike a chord? Drop a comment orsend me a message.
Ready to tackle your own challenges head-on? Let’s talk about how Purple Infinity, in partnership with Vistage, can help you navigate with clarity and confidence.