How to Ask for Help Without Feeling Awkward
During a recent Office Hours, we discussed: “How do I ask for help without feeling weird about it?”
It’s a question that comes up often, especially from women. Asking for help can feel awkward, vulnerable, and a little icky, but I think we’re looking at it wrong.
A few days ago, I got an email from a student whose class I guest lectured in asking if I’d consider advising her for an entrepreneurship class. Her request was flawless. It was specific. It was respectful of my time. She clearly outlined the commitment and included context on why she contacted me.
Importantly, it wasn’t the first time I’d heard from her. She followed up with kind feedback after the talk I gave in her class. That small gesture made her memorable, and we had a message history.
Saying yes was easy.
Her email reminded me how much more comfortable these asks can be when we approach them with intention. So, if asking for help makes your skin crawl, here are three things to keep in mind:
1. People want to help
When someone asks you for help, do you get annoyed? Probably not. You either say yes, say no, or offer an alternative. That’s it.
So why do we assume the worst when the roles are reversed- that we’re somehow putting someone out or taking advantage?
I juggled running a venture-backed startup while trying to pass International Business in college. When I got invited to speak at the World Knowledge Forum in South Korea—the same day as a major midterm—I debated dropping the class. Instead, I took a breath and asked. I explained the opportunity, attached the email from the event organizer, and offered to take the exam early.
To my surprise, the professor was thrilled for me. He let me take the test when I got back. That exchange changed how I approached help: when you’re honest and clear, people are often happy to support you.
2. Be direct. People don’t want to guess how to help you.
The vaguer the ask, the more uncomfortable it feels.
“Let’s catch up” doesn’t mean anything. But “I’m exploring [X], and I’d love your thoughts—do you have 15 minutes next week?” is specific and respectful of the other person’s time.
This is true for introductions, too. Don’t ask, “Do you know anyone who can help me?” Ask:
“I saw you’re connected to [Name]. Would you be open to making a quick intro? I’ve drafted a short blurb you can forward to them.”
When you make the ask clear and easy to say yes (or no) to, you reduce the other person's mental load and boost your odds of getting help.
3. Connect Before You Ask
There’s a saying in startup circles: “If you want money, ask for advice. If you want advice, ask for money.” The idea is that warm connections matter. A warm intro rooted in real rapport is much more likely to get a yes.
One way to make asking for help feel less transactional (and therefore less icky) is to lead with generosity.
Even small “five-minute favors” (a term Adam Grant popularized) make a difference.
Connection can take many forms:
A compliment on a recent article or podcast
Sharing something relevant to their interests
A review for their book (hint, hint)
These five-minute favors can have a huge impact. It’s not because you’re playing some game but because they show that you care before you need something.
Most of us want to help, especially when the person asking is someone we know or like. The best asks feel like invitations to be part of something. If you start with intention and generosity, it won't feel awkward when it’s time to ask for help. It’ll feel like the next step in a relationship you’ve already been investing in.
🥳 Come to my audiobook release party! More info here!
🕜 Come to my free office hours! The next one is on 4/25 at 1:30 pm ET. More info here!
🚀 Need help with performance marketing or GTM strategy? Sign up to be notified when my new marketing course for entrepreneurs and small teams is available.
🔌 Or book a power hour
📖 Grab a copy of my book! Amazon | Barnes & Noble | Signed Copy