The Real Obstacle to Leadership Success and How to Overcome It
What’s the Number-One Obstacle to Successful Leadership?
* Excerpt from Larry Jacobson’s keynote filmed live at the INFOSYS SAP Leadership Forum in New York (co-sponsored by AWS)
Ask any room of executives, and you’ll hear a chorus of answers:
“Poor communication!”
“Lack of confidence”
“Managing change in this environment”
These are real, formidable challenges that trip up even the most seasoned leaders.
But in my 30+ years as a CEO and later coaching leaders across industries, I’ve discovered something surprising: there’s one obstacle that underlies all of these challenges, one silent brake that keeps brilliant leaders stuck in their comfort zones, second-guessing decisions, and playing it safe when bold action is needed.
That obstacle is fear.
Yes, fear. Not the kind that makes you run from a burning building, but the subtle, persistent kind that whispers in your ear during a board presentation, that tightens your chest when you’re about to make a big call, that keeps you awake at three in the morning replaying conversations and questioning your judgment.
Here’s what most leadership advice gets wrong: they tell you to “overcome your fear” or “push through it” or “be brave.” As if fear is something you can simply eliminate with enough willpower or positive thinking. But after decades of navigating my own fears—and watching hundreds of leaders wrestle with theirs—I’ve learned something counterintuitive.
Fear isn’t the enemy. In fact, when you learn to recognize it, accept it, and channel it, fear becomes one of your most powerful leadership tools.
Let me tell you what I mean.
When Fear Shows Up Uninvited
I’ll never forget standing on the deck of a small sailboat, leaving the Golden Gate Bridge behind me and heading into the vast Pacific Ocean. The sea was running at 30 feet—massive walls of water that made our vessel feel like a toy. My palms were drenched, my heart was hammering so hard I could feel it in my throat, my eyes darted constantly to scan for the next wave.
I’d left behind a secure CEO position, a steady income, an established identity. Everything that had defined me for decades was receding into the distance with that bridge. And the fear? It was absolutely overwhelming.
But here’s what I learned in that moment: those physical sensations—the racing heart, the sweaty palms, the heightened alertness—weren’t signs that something was wrong. They were my body’s natural alarm system doing exactly what it was designed to do: sharpening my focus, flooding me with adrenaline, preparing me to perform at my absolute best.
The same thing happens in boardrooms and high-stakes meetings. That knot in your stomach before a crucial presentation? That’s not weakness. That’s your focus-engine warming up.
The Two-Step Method That Changes Everything
Most leaders I work with spend enormous energy trying to suppress or hide their fear. They see it as unprofessional, as a sign they’re not cut out for leadership. But this approach backfires spectacularly. When you fight fear, it grows stronger. When you pretend it’s not there, it leaks out in ways you can’t control—through micromanaging, through analysis paralysis, through missed opportunities.
What if, instead, you worked with fear?
Step One: Simply Notice
The first step is beautifully simple: notice that you’re afraid. Not in a judgmental way, but with curiosity.
When that familiar tightness hits your chest before a difficult conversation, pause for just a moment. Mentally label what you’re experiencing: “My hands are clenched. My breathing is shallow. My thoughts are racing. That’s fear showing up.”
This small act of naming takes fear out of the realm of the unknown and makes it manageable. You’re not having a breakdown; you’re having a completely natural human response to something that matters to you.
Step Two: Make Fear Your Co-Pilot
Recognition alone isn’t enough. The real transformation happens when you accept the fear and decide to use it.
Here’s what this looks like in practice: Instead of telling yourself “I shouldn’t be nervous about this,” try saying, “I see you, fear. I know you’re here to sharpen my attention. Thank you for that. Now, let’s get to work.”
Reframe fear’s purpose. It’s not trying to sabotage you—it’s trying to focus you, to make you alert, to ensure you bring your A-game. Tell yourself: “This nervous energy is going to make me sharper, more present, more precise in this moment.”
When you do this, something remarkable happens: the fear doesn’t disappear, but it stops calling the shots. It becomes a passenger in your car, not the driver. You stay in control.
I’ve watched this play out hundreds of times with leaders I coach. A CFO preparing for a contentious board meeting. A founder about to deliver feedback to a co-founder. A VP deciding whether to champion an unpopular but necessary change. When they stop fighting the fear and start channeling it, their performance transforms.
The Worry Trap
Fear has a less productive cousin: worry. And if you’re like most leaders I know, you’ve spent countless hours trapped in worry’s vicious cycle.
Will the product launch succeed? What if the team doesn’t hit targets? Did I make the wrong hire? Should I have said that differently in the meeting?
Here’s the truth about worry: it’s a complete waste of your mental energy.
I learned this the hard way, burning midnight oil on my sailboat voyage, churning through scenarios that might never happen, exhausting myself with contingencies for contingencies. Finally, I developed a simple three-question filter that has saved me countless sleepless nights:
- Do I actually have a problem? If no, there’s nothing to worry about. Move on.
- Can I do something about it? If yes, stop worrying and start doing. Take action.
- If I can’t do anything, does worrying help? The answer is always no—so focus on acceptance instead.
This framework sounds simple, but it’s revolutionary. When you catch yourself spiraling into worry, run through these three questions. You’ll discover that most of what consumes your mental bandwidth falls into the “worrying changes nothing” category.
Leaders who eliminate needless worry free up enormous mental capacity for what actually matters: strategic thinking, creative problem-solving, genuine connection with their teams. The result? More clarity, faster execution, and a much calmer presence that others can lean on.
Risk Is Where the Magic Happens
Here’s where fear and leadership intersect in the most powerful way: risk.
Without risk, there’s no real accomplishment. Every significant achievement in your career—and in your life—required you to step into uncertainty. To leave the dock, even when you couldn’t see the destination.
But most leaders I meet have developed an uneasy relationship with risk. They’ve learned to play it safe, to opt for the known over the unknown, to choose comfort over growth. And fear is usually what keeps them there.
The sailing metaphor is apt: you can’t explore new waters if you never cast off the dock lines. You can stay tied up, where it’s safe and predictable. But you’ll also stay exactly where you are.
I’ve seen leaders transform their entire organizations when they finally embraced calculated risk:
- The CEO who restructured her entire leadership team despite the short-term disruption, because she knew the current structure couldn’t deliver the next phase of growth
- The founder who walked away from a profitable but soul-crushing business model to pursue something more meaningful, even though it meant starting over
- The VP who championed an unconventional product idea that everyone else dismissed, and turned it into the company’s biggest revenue driver
None of these moves felt comfortable. All of them triggered intense fear. But in every case, the leader recognized that the bigger risk was staying put.
How to Calculate Risk (Not Eliminate It)
Here’s what I tell the leaders I coach: risk isn’t reckless. It’s calculated.
There’s a huge difference between:
- Taking a blind leap versus assessing potential downsides and preparing contingencies
- Being impulsive versus being decisive after gathering the relevant information
- Betting the farm versus making a strategic investment in growth
Think about risk on a spectrum:
Low-risk moves might include trying a new meeting format, delegating a task you usually keep to yourself, or pitching an unconventional idea in a brainstorming session. These are your training ground. When performance feels stagnant, small calculated risks build momentum and remind you that change doesn’t have to be catastrophic.
Medium-risk moves might involve launching a new product line, restructuring a team, or significantly changing your go-to-market strategy. Take these when data shows your current path isn’t delivering. These risks force innovation and prevent the complacency that kills companies.
High-risk moves might include pivoting your entire business model, leaving a secure position for an opportunity with much higher upside, or making a major market expansion. Take these when your vision is crystal clear but your comfort zone is too tight. These are the moves that can unlock transformative growth—but only when you’ve done your homework.
The key is this: assess the downside, prepare for what could go wrong, and then move forward with confidence. Don’t let fear masquerade as prudence. Sometimes the most “prudent” choice is actually the most fearful one in disguise.
Practice Your Way to Confidence
Just as athletes train their muscles, leaders must train their relationship with fear and risk.
Start small. This week, identify one low-stakes risk you can take. Maybe it’s:
- Having a difficult conversation you’ve been avoiding
- Delegating something you usually micromanage
- Admitting “I don’t know” in a meeting instead of bluffing
- Proposing an idea you’re afraid might sound naive
Then pay attention to what happens. In most cases, you’ll discover that the fear was disproportionate to the actual risk. The conversation went better than expected. The person you delegated to rose to the challenge. Admitting uncertainty made you more human and trustworthy, not less competent.
Celebrate both the successes and the lessons learned. Over time, your brain rewires itself to view risk as a normal part of the workflow, not a threat to be avoided at all costs.
This is how you build leadership muscle. Not by eliminating fear, but by getting comfortable operating alongside it.
What I Wish I’d Known Earlier
Looking back on my journey—from those early CEO days when I thought leadership meant having all the answers, through that terrifying but transformative voyage across the Pacific, to now coaching leaders through their own crossroads—I wish someone had told me this:
Fear is inevitable. It comes with the territory of leadership. Every decision that matters, every change that creates value, every goal worth pursuing will trigger it.
But fear doesn’t have to be a barrier. It can be a signal that you’re onto something important, that you’re at the edge of your comfort zone where real growth happens.
The leaders who make the biggest impact aren’t the ones who feel no fear. They’re the ones who feel the fear, recognize it for what it is, and move forward anyway. They use that nervous energy to sharpen their focus. They channel it into decisive action. They step out of the comfort zone and sail confidently into the unknown.
And here’s what they discover: the most intimidating seas often lead to the most rewarding horizons.
Your Turn
So here’s my challenge to you: What’s one fear you’ll name and embrace this week? What’s one calculated risk you’ll take?
Don’t wait until you feel ready. Don’t wait until the fear goes away. It won’t.
Start from where you are, with what you have. Notice the fear. Accept it. Channel it. Take the risk.
The journey to exceptional leadership begins the moment you decide to move forward—fear and all.
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