Who It’s For: Entrepreneurs, Senior Business Leaders, Managers, Sales Professionals, Female Leaders, and R&D, Innovation, DEI, and Other Critical Teams
How to Ask Your Company to Pay for Executive Leadership Coaching (and Why It’s Worth It)
Darlene Hawley
Want your company to pay for executive leadership coaching? Learn how to ask with clarity and confidence, plus a sample email script to get the conversation started.
When I was first promoted into leadership, there was no formal training program or structured support. My manager mentored me as best they could, but the company didn’t offer any real leadership development. I was serving, observing, and learning as I went.
I remember sitting in meetings, unsure how to speak up… even when I had ideas that could truly make a difference. I was nervous to give feedback, and I was leading my friends. I was working hard, but inside I felt like I was winging it and struggling to feel like I could get their buy-in.
Back then, I didn’t even know executive coaching existed.
Now, having supported hundreds of leaders and entrepreneurs over the years, I see just how powerful it is to have someone walk beside you... to help you see your blind spots, find your voice, and lead with confidence.
And here’s something a lot of people don’t realize:
you don’t always have to pay for it yourself. Many organizations have budgets to support leadership development, you just have to ask.
If you’re ready to grow, here’s how to confidently ask your company to support you in getting the coaching you need.
1. Start with Your “Why”
Before you make the request, get clear on why you want coaching. What are you working toward? What challenges are you navigating?
Maybe you want to…
- Lead your team more effectively
- Show up with confidence in high-stakes meetings
- Position yourself for a promotion
- Communicate with clarity and presence
- Be invite to speak at conferences or be a guest on a panel
- Learn how to have hard conversations with less anxiety
- Position yourself as a thought leader in your industry
The more specific you can be, the easier it is for your organization to see the value in supporting you. This also helps you advocate for yourself without second-guessing.
2. Show How It Connects to the Company’s Goals
Coaching isn't just about you (though you're 100% worth it). It also benefits your team, your department, and your organization.
You can say things like:
“I want to strengthen my communication skills so I can lead my team more effectively.”
“I’ve noticed some challenges with cross-functional collaboration, and I’d like support navigating that.”
“I’m preparing to take on a bigger leadership role, and I want to make sure I’m showing up with confidence and clarity.”
In my work, I’ve helped clients increase team performance, navigate conflict, improve presentations, build more inclusive teams, and lead initiatives that create real impact. Your growth is your company’s gain.
3. Do Your Research First
Check to see if your organization has professional development funds or a leadership training budget. You might:
- Review the employee handbook or intranet
- Ask HR or your direct manager what’s available
- Talk to a colleague who has received external coaching or attended a leadership retreat
Even if there’s no formal policy, many companies have discretionary budgets. You’d be surprised how often the answer is yes when you make a clear, thoughtful request.
4. Make the Ask with Confidence
Once you’ve done your prep, make the ask. Keep it professional, future-focused, and aligned with your goals and the company’s goals.
Here’s a simple script you can use (tweak to fit your voice and goals):
Email Template
Subject: Executive Coaching Request
Hi [Manager/HR Name],
(Start with a personal sentence or two.)
I’ve been reflecting on ways I can grow as a leader and continue contributing at a higher level. One area I’d like to focus on is [insert your focus: e.g., communication, executive presence, team leadership].
I’ve identified an executive coach who supports professionals like me with developing stronger leadership skills, navigating career growth, and showing up with more clarity and confidence. I believe working with a coach will help me grow faster and more intentionally, and ultimately be an even stronger asset to the team.
I’m wondering if there’s a professional development budget that could support this? I’d love to chat and share more about how this aligns with my goals and the organization’s priorities.
Thanks so much for considering,
[Your Name]
5. Have a Plan B
Not every company says yes. That doesn’t mean you don’t deserve support.
If your request is declined or funding isn’t available or even put on hold at the moment, I want to gently encourage you to invest in yourself. You don’t need to wait for permission to grow.
I’ve had clients pay out-of-pocket for 1:1 coaching or a VIP Day because they knew the clarity, confidence, and tools they’d gain would serve them for years to come... not just in their current role, but in everything they build next.
You’re Worth the Investment
Whether you’re climbing the leadership ladder, navigating a big transition, or simply ready to feel more confident and aligned in your role... you don’t have to figure it out alone.
Your growth benefits everyone around you. Don’t be afraid to ask for support.
And if you’d like help having this conversation (you know your girl loves to role play) or want to explore coaching together, I’m here. I work with executive women, rising leaders, and heart-centered entrepreneurs who are ready to step into the next chapter of their career with clarity, presence, and power.
You’ve got this. And you don’t have to do it alone.
Schedule a quick 30-minute strategy call, and let's see how I can best support you in reaching your goal.
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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.
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I was facilitating a one-day Speak Up & Influence team-building experiential training when I noticed her sitting quietly in the back of the room. She participated, but never fully spoke her mind, staying just under the radar, what I like to call "playing it safe". After one of the vocal empowerment activities, I walked over and said, “You know, the way you just helped your group reframe that challenge? That’s leadership. And I don’t think anyone’s told you lately... but you have a really powerful presence when you speak.” She blinked, stunned. Then smiled...a BIG cheesy grin. “Wow. I… don’t think anyone’s ever said that to me,” she said. “I thought I was just rambling.” That moment changed her energy and how she showed up the rest of the day. She spoke up more. She leaned in. She took more space. By the end of the day, she was laughing with her colleagues and, dare I say, being Bold and having FUN. That’s the power of being seen. Not liked. Not evaluated. Not coached. Witnessed. Witnessing Is Deeper Than Praise Recognition isn’t just about saying “good job.” It’s about creating space for people to feel seen in the room. And as an executive leadership coach, trainer, and speaker, I believe this is one of the most powerful tools we have. It’s part of why I teach the Step into Your Moxie® Vocal Empowerment Framework to help people speak with confidence and presence, And to help them feel safe enough to show up as unapologetically as themselves. The framework includes: Naming the Inner Critic Creating Psychological Safety Clarifying the Message Owning Presence Moving People to Take Action But none of that sticks if we don’t feel witnessed. The Real Role of Recognition in Leadership Recognition is not limited to annual performance reviews. It’s being in the moment with someone. It’s telling the truth of what you see... and helping them see it too. When we recognize someone for who they are, not just what they do, it creates: Trust Confidence Belonging Momentum It tells them, “You matter. Right now. Just as you are.” And for many people, that’s enough to shift everything. How Vocal Empowerment Starts with Being Seen I’ve worked with countless leaders who don’t need help with strategy... they need to be reminded they have a voice worth sharing. Their ideas aren’t the problem. Their presence is stifled by years of not being heard. And when someone finally says, “I see you. I hear you. I believe you have something valuable to say,”... they rise to the occasion. That’s what witnessing does. That’s what coaching is. And that’s what powerful leadership should include. My Truth About Leadership + Visibility I believe every single person deserves to be put in a position where they are the leader. But leadership is not one-size-fits-all. It’s not about being the loudest or most polished. It’s about being thoughtful about the right kind of visibility... and showing up unapologetically as yourself. We need more leaders who understand this. Who witness others without fixing them. Who show people what’s possible by being real, not rehearsed. How does it feel when someone truly witnesses you... not just your performance, but your presence? And who in your world could use that kind of recognition right now? Say it. Share it. Watch them light up. Try This: A Visibility Icebreaker That Builds Trust Here’s a simple, powerful exercise I love using to open workshops, team meetings, or small groups: Two Truths and a Lie: Leadership Edition Each person shares: Two true things about how they lead, speak, or show up One “lie” they used to believe about themselves Example: ✔ I’m a clear communicator ✔ I make people feel safe when I lead ✖ I’m not good at public speaking (← the old lie) This twist brings visibility and vulnerability together... without putting anyone on the spot. It allows people to own their growth and shift their inner critic by speaking it out loud. Try it. Let me know how it goes with your next team meeting. Coming Next in Part 4: Crafting Connection: Simple Rituals to Help You and Your Team Feel Seen Because being witnessed isn’t a one-time act. It’s a culture. It’s a practice. And it starts with you.
We’ve never been more connected... and never felt so unseen. With a few taps, we can join a Zoom room, drop into a DM, or post something vulnerable for hundreds of people to witness. But there's a disconnect. And in a tech-driven world where everything moves fast and engagement is measured in emoji reactions… are we truly connecting... or just being consumed? “To be recognised, you have to be seen, you have to be heard – and that requires a witnessing that can’t happen in two-second increments.” —— Allison J Pugh in her article The Unseen in Aeon Magazine You can post every day and still feel invisible. You can be in a dozen Slack channels and still feel isolated. You can have 10k followers and feel like no one is really paying attention. Because we’ve built a world where connection is constant... but deep roots are rare. The Pace of Tech vs. the Slowness of Being Seen We scroll fast. We skim emails. We record meetings and never rewatch them. But being seen takes time. It requires presence. Stillness. The very things today’s digital culture works against. And when you’re constantly “on”, but rarely witnessed... it’s easy to feel like you’re disappearing in plain sight. This is especially true for entrepreneurs and leaders. We’re told to post, share, create, show up, stay visible… and yet, we’re rewarded for comments, not true connection. That’s the tension we’re living in... and the one we need to name. Why I Don’t Create for Social (and What I Do Instead) Let’s get honest, social media isn’t the main event... it’s the after-party. The first time someone finds me isn’t on LinkedIn. It’s at a speaking event, on a podcast, or through a referral. Then they follow me on social. Then they join my newsletter. Social media isn’t where I get discovered. It’s where I nurture relationships that already exist. That’s why I don’t create for the algorithm... I write for my community. I share my heart through emails and long-form blog or video content. Then I repurpose it on social... not to “go viral,” but to stay connected. And here’s the magic part: Some of my clients? They’ve been on my list for 6+ years. Never replied to a post. Never commented. And one day... they book a call. Because they’ve been listening the whole time. They were waiting for the right moment.... not the right reel. When Tech Makes You Feel Small But even with that perspective, I still feel it. That sting when you pour your heart into a post and it gets 3 likes. That feeling after a Zoom room full of “great people!”… but the coffee chat that follows doesn't convert to referrals or business. That’s what the fast pace of our digital world does. It makes us visible... but not witnessed. It makes us accessible... but nothing deeper becomes of it. You can have the right lighting, captions, camera angle... and still feel like no one’s really seeing the person behind the post. The Shift: From Performance to Presence The solution isn’t more hustle or noise. It’s more presence. So, if you're feeling invisible right now, even while showing up “everywhere,” hit pause and take a breath. Ask yourself: Am I sharing because I have to, or from a place of inspiration? Am I connecting, or just posting to stay in the feed? Who am I hoping will really see me? Then, choose one way to show up differently this week. Call someone instead of commenting. Write the post that feels inspiring, not strategic. Or close the laptop and go be with real people, even when it feels uncomfortable. Because yes, people are watching... even if they’re silent. But more importantly, you deserve to feel connected, even when tech feels like it's sucking your soul.
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