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Home » How to ask the “very scary questions” in a cold email
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How to ask the “very scary questions” in a cold email

adminBy adminNovember 20, 2025No Comments3 Mins Read
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Five years ago, Carly Valancy, inspired by Molly Beck’s book Reach Out, set out to reach 100 new people in 100 days.

The challenge has created “incredible opportunities” in her career, from new jobs to mentor relationships, says Valancy, co-founder of growth consultancy Momentum Growth.

Valancey, 30, is repeating the 100-day challenge this year and sharing her skills through her networking strategy collective, Reach Out Party.

Her goal, she says, is to make the process of building new connections less scary.

“Reaching out has a very compounding effect, and the more you do it, the better you’ll be at communicating who you are and what you want,” she says.

Here’s Valancey’s advice on what to say when reaching out to someone new:

What to include in your message

Valancy’s most important rule is that each networking message must be “specific, generous, and honest.”

To qualify as specific, “it has to be a message that only you can send and only they can receive,” she says. It’s important to show that you are paying attention to the work they are doing.

The generous message includes what Valancy calls a “gift.”

“This could be anything from a specific compliment to a book recommendation, or any way you can help that person’s career or connections you can make,” she says. “Think, ‘How can I serve their job instead of mine?'”

Finally, “honesty really speaks to me,” Valancy says. “Whether it’s sharing your fears (reaching out) or sharing where you really are at this moment in your life.”

“These things are really powerful for building meaningful connections,” she says.

How to ask without being shy

Above all, make sure your message has a clear purpose, says Valancy.

When Valancy reaches out to potential clients for her consulting business, she says, her goal is “very clear” to see if they’re a good fit to work together.

It can be intimidating to ask strangers for meetings, introductions, and favors, but one of Valancy’s key networking principles is to “ask without shame.”

“Early in my career, I would really reach out to people without asking at all, or very shyly, like, ‘I guess you don’t have time for this,'” she says.

As she gained experience, she became more confident in expressing what she wanted openly. If you do take the plunge and reach out to someone, she says, you might want to ask the “big, scary questions.”

Valancey finds this thinking exercise helpful. “What would I say if I knew they would be willing to say yes?”

Even if you get a rejection or no response at all, it’s good practice for your next message, Valancy says. “The more questions you ask, the more you can refine and shape what you actually want.”

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