Why Entrepreneurs Should Master The Art of Asking


This post was originally published on NOEW.org. New Orleans Entrepreneur Week is an annual festival celebrating entrepreneurship and innovation in New Orleans. 

I’ve been a big fan of Amanda Palmer and The Dresden Dolls for at least a decade. As Amanda has branched out from the music business, I continue to be impressed with her work. Her TED Talk moved me, and she made history by kickstarting her Theatre is Evil album. So, I gave her book, The Art of Asking, a chance, and I ended up binge reading it over the course of two days.

What Amanda has to say about community building and asking for help has had a large influence on the work I do in contributing to CommitChange’s company culture and on my philosophy for handling support issues. I’ve worked for companies in the past where employees were afraid to ask for help, and in which they were sometimes even pitted against each other in a misguided attempt to increase productivity through competition. I’ve seen offices grind to a halt and company cultures fracture because coworkers were afraid to work together on projects. The paranoia and animosity extended to those companies’ clients, who were seen as obstacles instead of customers, which limited the relationship building that was possible at all levels of the organization.

Though asking for help can be hard, especially when you want to be seen as an “expert,” in my experience it actually builds trust. Reading The Art of Asking helped me see how I could extend my practice of asking without having to worry about looking weak or incompetent. Here are the main takeaways that have helped shape my work:

1. Knowing “your crowd” is key.

Amanda spent years building a following before signing a major record deal, and many of the hard lessons she learned were a result of her label trying to change the way she related to her fans. The label didn’t think the niche crowd she was attracting was lucrative enough. She butted heads with her label the entire time she was signed on, but when she dropped her label, it was the core fan base label heads dismissed who were willing to keep her going.

In the tech community there’s a lot of focus on growth and scaling, but it’s important to keep your core users in mind for everything from how you build your product to how you handle support conversations. If you focus on building the perfect, quality product for your ideal client, people are going to take notice and sign on. On the other hand, if you try to build something that appeals to everyone, chances are your focus and the quality of what you’re building will be diluted.

2. Asking for help builds relationships.

It’s awkward to ask for help, but we have to do it all the time. In Palmer’s case, couchsurfing and busking led to an organic crowdfunding strategy; at a startup or small business, the ask is key at every level, from finding investors to mining for feedback. Sometimes you ask people to sign on and use your product for free in exchange for feedback and testimonials, sometimes it’s putting together elevator pitches for when you meet the perfect advisor in a hotel lobby. The key is finding the members of your crowd, tailoring your ask to appeal to them, and being open and honest about what you need.

3. Reciprocation is the cement that holds your crowd together.

Find ways to help others. Host that one-hour class for a client’s favorite nonprofit or help someone troubleshoot a problem at a hack night. Members of your crowd will be able to see you shine at what you do best. They’ll see the value your provide to others, and they’ll recognize you as a member of the community. Palmer caught some flak for asking musicians to play songs for free and busk the lines at her shows, but she did this in part because the performers she asked were already a part of her crowd, and they agreed under the terms she presented. She often plays free ninja gigs organized over Twitter, and she’s helped fans connect with each other on social media and through her blog. When you actively offer what you have to give, community will form around you because people who take concrete action to help others really stand out.

Wendy Bolm is the Director of Support and Nonprofit Advocacy at CommitChange, a company that builds online fundraising tools for nonprofits, with an emphasis on sustainable fundraising and user experience. You can follow her on Twitter @wendylbolm

Wendy Bolm

Wendy is the Director of Support and Nonprofit Advocacy at CommitChange, a company that builds online fundraising tools for nonprofits, with an emphasis on sustainable fundraising and user experience.

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