How to reach out to someone (when you're not sure what to say)

Every once in a while, someone reaches out after a workshop or session and asks me for a copy of something I mentioned. Recently, it was a guide on how to approach a senior person—like a CTO—and ask them for advice or mentorship.

Honestly? I get it.

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Reaching out to someone you admire can feel like trying to text your crush without sounding desperate.

You don't want to ramble, but you don't want to sound like a robot either.

You want to sound like you. Human. Genuine. Not someone who googled “professional networking email” and panicked.

The good news? It’s not actually that complicated. You just need a few Wing People moves up your sleeve.

First: get your head in the right place

Before you even open LinkedIn or your inbox, take a breath and remind yourself:

• Make it about them, not you.
• Be clear and specific about why you’re reaching out.
• Keep it casual at the start. You’re opening a door, not proposing marriage.
• Respect their time. Offer something light and easy.
• Always say thank you. Always.

Most people are flattered when someone notices their work. Seriously.
No one gets to the top alone. Everyone remembers what it was like to wonder what the heck they were doing.

When in doubt, follow this formula

Admiration + specificity + clear ask + gratitude.

Example:

"I really admire how you’ve built your career at [Company]. I’m exploring a similar path and would love to hear your advice. Would you be open to a quick coffee or call when it works for you? I’d really appreciate it."

Simple. Honest. Easy to say yes to.

Message templates you can use

Here are a few plug-and-play scripts depending on what you're reaching out about.

Career advice and mentorship

Reaching out to an experienced professional you sort of know

Hi [Name],

I’m exploring my next career move, and you immediately came to mind. I’ve always respected how you’ve navigated your career at [Company/Industry].

If you’d be open to it, I’d love to buy you a coffee (or a virtual one) and get your advice on my next steps.

Thanks so much,
[Your Name]

Asking a peer for advice

Hi [Name],

Even though we’re at a similar stage in our careers, you’re someone whose opinion I really respect. I’m thinking about my next move and would love to hear your perspective if you have a few minutes to chat.

Thanks,
[Your Name]

Asking someone to be a mentor

Hi [Name],

I’ve been reflecting on my next career moves, and you immediately came to mind. The way you’ve built your career and leadership style is something I really admire.

I know you’re busy, but I wanted to ask if you’d be open to a casual mentoring relationship—something low-pressure like an occasional coffee chat. I’d be honoured to learn from you.

Thanks so much for considering it,
[Your Name]

Getting to know someone better (no big agenda)

Casual “you seem interesting” connection

Hi [Name],

I’ve come across your work a few times and just wanted to reach out. You seem like someone who’s doing really cool things in [industry/community].

If you’re ever up for a casual coffee chat, I’d love to hear more about what you’re working on and swap stories.

Thanks,
[Your Name]

Following up after meeting at an event

Hi [Name],

It was great meeting you at [Event]! I really enjoyed our conversation about [topic].

Would you be up for a coffee sometime to continue the conversation? I’d love to hear more about what you’re working on and see if there’s any way I can support you.

Thanks,
[Your Name]

Exploring solopreneurship or career pivots

Reaching out for solopreneur advice

Hi [Name],

I’m starting to explore the idea of going out on my own and building something as a solopreneur. I know you’ve walked this path already, and I really admire how you’ve done it.

Would you be open to sharing a little bit about your journey? I’d love to hear any lessons you wish you knew when you were starting out.

Thanks so much,
[Your Name]

Looking to connect with other founders/builders

Hi [Name],

I’m in the early stages of building something new and trying to learn from people who have walked a similar path. I’ve been following your journey and really admire how you’ve grown [Project/Business].

Would you be open to a coffee or a quick call? I’d love to hear about your experience and share a little about what I’m working on too.

Thanks,
[Your Name]

How to make it about giving, not just taking

This is the Wing People difference.
Real relationships are built on mutual value, not just transactions.

Here’s how to show up with a "give" mentality:

• Ask how you can support them too. Even if it’s small, it matters.
• Offer to introduce them to someone useful if you can.
• Share an article, event, or opportunity they might like.
• Follow up with a thank you—and tell them something specific you learned.
• If you end up building a relationship, be generous with your support later too.

Example of offering value back in a message:

Hi [Name],

I really appreciate you taking the time to chat with me.
If there’s ever anything I can do to support you—whether it’s sharing a project you’re working on, introducing you to someone, or just cheering you on—please let me know.

Thanks again,
[Your Name]

Wing People tips to make your message land

• Start with a real compliment. Not fake, not generic.
• Be clear and respectful. Tell them why you’re reaching out and what you’re hoping for.
• Make it easy for them to say yes. Keep it light. No giant commitments.
• Be human. Write like you would actually talk if you bumped into them at a coffee shop.
• Always follow up with genuine gratitude. Always.

If you’re feeling stuck, here are some prompts to help

Before you send your message, ask yourself:

• What is it about this person that makes me want to reach out?
• What’s one specific thing I want to learn, explore, or share with them?
• How can I make this feel light, genuine, and not transactional?
• How would I say this if we were grabbing coffee together right now?

Then just... send it.

Final pep talk

Reaching out isn’t about being perfect. It’s about being real.
It’s about showing up as a human being with curiosity, admiration, and respect.
People can tell the difference. And they appreciate it more than you think.

You’ve got this.

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(and if you ever need a Wing Person in your corner, you know where to find me.)

Happy connecting,

Shaena

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