How to ask for help

If leading with generosity is the best way to build your network, what do you do when you actually want something from someone? How do you reconcile being generous with being needy? I need help all the time. In the last week alone, I’ve asked for and received help on starting a new project at work, analyzing European data privacy rules, and reviewing the first 80 pages of my upcoming book. Many of the responses were from people I’ve never met.

Here are 5 things I keep in mind when I ask for help.

Get to know them first

Before you ask someone for help, do all you can to get to know them first. Look for them online and offer them the universal gifts of recognition and appreciation. Read what they’ve written. Follow them. Like their content. Offer a comment.

For example, if you’re an entrepreneur, you would surely benefit from the advice of Fred Wilson, perhaps the most notable venture capitalist in NYC. He’s so busy, though, that he’d likely never see your email or your offer to have coffee.

But you can read his blog and get to know him that way. Over 10 million people have visited Fred Wilson’s blog. But only 10,000 have commented. Only 1,000 have contributed in campaigns for And even fewer people regularly participate in online discussions in what he calls the community.

Who would Fred be more likely to help, someone who hasn’t bothered to read what he’s already offered or someone who’s made the effort to be part of his community? Before I’d approach him for help, I’d try to get closer to him in other ways.

Frame it as a contribution

Empathy, empathy, empathy. As you’re writing that email or LinkedIn request, imagine yourself reading it and asking What’s in it for me? Here’s a story from Tim Grahl, who helps authors market their books:

“Two authors recently emailed me for the first time. The subject line of the first read “Let’s meet.” The email shared the author’s struggle marketing his book and a request for a phone call so he could “pick my brain” about what he was doing wrong and how to fix it.

The subject line of the second email read, “Interview.” The email was a request to interview me for his podcast so that he could share my advice to educate his listeners and promote my business.

Which one do you think got a response from me?”

Coffee and brain-picking aren’t incredibly attractive offers. Before you ask for help, spend time figuring out how the other person can gain something too. It might take some creative thinking on your part, but it will help you stand out and get better results.

Be the 8-foot bride

Amanda PalmerVulnerability can be a gift, too, when presented in the right way. Amanda Palmer delivered a beautiful presentation about this in her TED talk “The art of asking.” One of her first jobs was standing on a crate dressed as a bride with a hat or can in front of her for donations. Those who gave money were treated with deep eye contact and a flower.

Later, as a struggling musician, she needed places to stay as well as food or equipment. She let fans know where she’d be and what she needed. The people giving got something in return: the chance to connect with her and be part of her journey. Her vulnerability made that possible. She felt strongly that “You don’t make people pay for music. You let them.” Her gifts didn’t appeal to everyone, of course. But when she asked for money on Kickstarter to launch a new album, 25,000 individuals donated a total of more than $1.2 million.

I think of the 8-foot bride when I ask people for help with my book or when I imagine selling it in the future. Most people will walk by. Some will stop and pick up a copy. Some might love it. I need to accept that my gift isn’t for everyone and ensure my requests feel more like an invitation than an imposition.

Don’t be a badger

When you’re vulnerable and people don’t respond, it can sting a bit. You might naturally feel rejected and that feeling can lead to bad behavior. I haven’t heard from you. Did you get my last email?!

Tim Grahl has more good advice for people seeking help from others.

“When you're in outreach mode, revoke your right to be offended. You’re not always going to get the answer you want. People are going to turn you down or just ignore you from time to time. That’s a part of the game; that’s a part of life. When you don’t get a favorable response, take a breath and move forward. Keep looking for ways to help people. Assume the best of people.”

When the people I’m coaching don’t get a response, we practice Tim’s advice. We assume the best of people - they’re simply busy or have some other legitimate reason - and we focus on what else we can do to be helpful. That mindset ensures your requests don’t feel like burdens and makes it much more likely people will respond favorably in the future.

Say thank you

Despite its simplicity, a sincere “thank you” is still a rare and cherished gift. When’s the last time you received a hand-written thank you note? Or a personal email describing the positive impact of your generosity? Or a public thank you on social media calling out your contributions?

You can turn your thank you into a special gift by making it personal or public. It costs you nothing but can be the thing that transforms a transaction into a meaningful connection. When people I’ve never met offer me appreciation for something I’ve done or written, I can’t help but feel especially connected to them and willing to help them even more.

When I get help, I try to think of meaningful ways to say thank you. More than 30 people are now reading the first two parts of Working Out Loud. Several people read the 80 pages in a few days, offering me everything from line edits to suggestions on flow and style. All of it valuable. All of it generous. For them and for all of you reading this, I offer my version of Amanda Palmer’s deep eye contact and a flower.

Asking someone for something is a normal and natural thing to do. Go ahead. When you present your request in the right way, asking for help can be its own special kind of gift.


p.s. Part III of Working Out Loud includes techniques, exercises, and stories that will help you work out loud towards a specific purpose.

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