Who It’s For: Entrepreneurs, Senior Business Leaders, Managers, Sales Professionals, Female Leaders, and R&D, Innovation, DEI, and Other Critical Teams
Why Smart Leaders Still Struggle With Confidence (and the Coaching Fix That Works)
Confidence isn’t automatic at the executive level. Here’s how to reclaim it.
When you reach the executive level, everyone assumes you’ve got it all figured out. You’ve proven yourself, you’ve earned the title, and you’ve built a track record of success.
But here’s the truth I hear from my clients all the time: even the smartest, most capable leaders still struggle with confidence.
And it’s not because they’re not good enough. It’s because leadership comes with pressure, politics, and high-stakes conversations that no one really trains you for.
The higher you rise, the lonelier it can feel.
You’re expected to have answers, to inspire your team, and to influence decision-makers.
Yet inside, you may be second-guessing yourself or wondering if your voice carries the weight it should.
The good news? You’re not alone. And it’s not a permanent state... It’s a skill you can strengthen with the right kind of support.
Why Confidence Slips (Even at the Top)
If you’ve ever felt like your confidence wavers in moments that matter most, you’re not broken.
You’re human.
Here are some of the most common scenarios where even senior leaders feel their confidence dip:
- The Boardroom Freeze: You walk into a high-stakes meeting with ideas that could shift strategy. But as the conversation speeds up, you hesitate. Your throat tightens, and by the time you gather the courage to speak, the moment has passed.
- Presentation Pressure: You’ve prepared for weeks to deliver a keynote, town hall, panel, or client pitch. But as the spotlight hits, your inner critic starts whispering: “What if I mess this up?”
- Pushback Fatigue: You know you’ll face tough questions or resistance from stakeholders. Instead of leaning in, you find yourself shrinking back, hoping to avoid conflict.
- The Recognition Gap: You’re putting in long hours, solving big problems, and leading teams... but the recognition (and compensation) doesn’t reflect your value. You start to wonder: “Am I not showing up bold enough?”
These situations are everyday among the leaders and entrepreneurs I coach.
The truth is, you can have years of experience and still feel uncertain about your voice, your presence, or your ability to influence in the moments that matter most.
The Hidden Cost of “Powering Through”
Many leaders tell me they’ve spent years trying to “power or push through” these moments. They tell themselves: If I just work harder, prepare more, or wait longer, my confidence will catch up.
But here’s the problem: confidence doesn’t automatically come with more experience or time in the role. In fact, the higher you climb, the more the stakes increase... and so does the pressure.
When you rely only on grit, three things often happen:
- Exhaustion sets in. You burn energy preparing and over-preparing, but it still doesn’t feel enough.
- Opportunities slip away. You hold back your best ideas or hesitate to apply for the next-level role.
- Isolation grows. You feel like you can’t admit these struggles to peers or superiors, so you carry the weight alone.
I know this because I’ve been there myself. Earlier in my career, I was the only woman in a conference room full of male leaders. I had ideas that could have changed how the team worked... but when it came time to speak, my body resisted. I felt my face flush, my throat tighten, and the words never came out. I drove home in tears, wondering why I couldn’t just “speak with ease.”
That experience is why I do the work I do now, because leaders deserve tools and support. A safe space to talk through a situation, and actually practice saying what they need to say out loud so they feel comfortable speaking up when the time is right.
That's my secret sauce in my coaching; we actually create space during every coaching session to roleplay.
I learned the hard way that we can't just map out what we want to say in our heads and think about how we want to say it. And then have the conversation or give the presentation.
We need to walk and talk and start speaking it.
I give you real space to play and embody your message so you can call people to action each time you speak.
The Coaching Fix That Works
This is where executive coaching changes the game. It’s not about telling you what to do... It’s about equipping you to step into every room, every conversation, and every decision with more confidence, calmness, and clarity.
When we work together, I help you:
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Find and refine your leadership voice so you can communicate with clarity and confidence, even when it feels hard.
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Build an authentic presence that allows you to be unapologetically you... without trying to be someone you’re not.
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Navigate daring conversations with confidence, so you can lead your team and influence decision-makers.
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Develop strategies for balance so you’re not just performing, but actually leading with energy and focus.
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Create a leadership plan aligned with your goals and values, so your career growth feels intentional, not reactive.
A Real Client Story
One of my clients, Sandy, came to me stuck in this exact cycle. She was a senior executive who had been avoiding a difficult conversation with a key team member for months. She worried it would create conflict and damage the trust they had build with each other.
In our coaching, we reframed it as what I call a daring conversation... an opportunity to lead with empathy and honesty instead of fear. We role-played, prepared, and practiced the messaging until she felt at ease and confident.
The result? She went into that conversation with clarity and calm. Not only did it go better than she imagined. It actually strengthened her relationship with the team member. She walked away with more trust, more respect, and more confidence in herself as a leader.
That’s the ripple effect of matching Strategy + Roleplay in coaching. When you show up differently, your team and your organization feel it too.
The Research Behind It
According to the Manchester Review, coaching can improve leadership effectiveness by over 60%.
Leaders who invest in coaching report higher performance, better decision-making, and stronger relationships at work.
It’s no coincidence that many of the world’s most influential CEOs, executives, and entrepreneurs all have coaches behind the scenes (I have a coach, too).
They know leadership isn’t about doing it alone... It’s about having the right support to step fully into your leadership.
You Don’t Have to Figure It Out Alone
Here’s the truth: confidence at the executive level isn’t about faking it until you make it. It’s about building the skills, strategies, and mindset that allow you to show up authentically and powerfully in every room you walk into.
You don’t need to wait years hoping it will “click.” You can start building that confidence now.
If you’re an entrepreneur, senior, or rising leader who’s ready to lead with more confidence, clarity, and impact, I’d love to support you.
✨Ready to Own Your Story and Attract Your Dream Clients?✨
If you’re ready to stop second-guessing your message and start using storytelling as a powerful tool to connect, inspire, and sell—then I’d love to invite you to my It’s Time to Own Your Story: Mini-Course.
In this self-paced course, you’ll learn how to:
✔️ Identify the key moments in your story that captivate your audience.
✔️ Share your story in a way that builds trust and positions you as the go-to expert.
✔️ Use storytelling across your website, social media, and sales conversations to attract and convert more clients.
Plus, you’ll get a
step-by-step workbook and
personal feedback on your brand story—so you can start sharing with confidence.
Hey There!
I'm Darlene
As a mother, wife, connector, and dream builder, I’m Darlene Hawley, the founder of DarleneHawley.com and an Executive Leadership & Businesss Coach dedicated to empowering leaders like you.
My passion lies in helping ambitious professionals cultivate their unique leadership style while crafting an authentic and impactful personal brand. Through my coaching, we’ll work together to build a solid foundation that not only inspires your team but also drives results and growth within your organization.
Since 2007, I have been committed to guiding leaders and entrepreneurs in launching and scaling their businesses with confidence and clarity.
Today, I focus on supporting women in reaching their leadership goals and living their dream lives—all while balancing the joys of raising my family and creating meaningful memories each day.
Together, we’ll transform your challenges into opportunities, allowing you to lead with authenticity and inspire those around you.
