Pick up the Phone

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Hey honeys and hustlers,

Brand is in the eye of the beholder. Have you ever thought about how your customers see you? I mean, really see you—not just your product or service, but your place in their lives? There are questions we need to ask for customer data and feedback to truly impact our business that go far beyond satisfaction. We need to dig deeper, getting inside our customers' minds to understand how they categorize us, when they choose us, and why they might leave us. After all, the most valuable insights often come directly from those we serve.

In today’s article, I wanted to share some questions I ask people in discovery calls and after working with me to help me better position myself, prices, and services as a freelance creator. Customer retention and conversion of leads into business are the two greatest areas of opportunity for small business owners. These will translate to any other creative business model, so if you’re a product-based business owner, an online content creator, or another service-based business, these will be relevant for you as well.

Talking to customers about things that seemingly aren’t related to the scope of work can be scary. At least, it was for me. What if they tell me they only went with me because I was the cheapest option? What if they only bought from me because other creators were booked? While I was scared to ask, I knew a few simple truths:

• everyone starts somewhere

• I may have been less expensive as a solo creator, but I was working toward building a team

• if they booked with me once and I did a great job, it’s likely that they would be willing to book with me again (and grow with me as my prices increased)

P.S. Stay to the end for my experience chatting with an AI bot about my business and a quick question! I'm headed to the beach to participate in the Hatch-a-thon and then have some quality vacation time with my family this weekend. Wish me luck (both with pitching and fully unplugging)!

When I wanted to grow my business beyond sporadic portrait sessions and event photography, I knew I needed to understand more about why people buy. I wasn’t sure where I stood in the market or how to differentiate myself enough to charge higher prices. When speaking with another creative business owner, they told me they were able to niche down to being a boutique wedding vendor simply by talking to their current and prospective clients. This helped them book clients more consistently with a high conversion rate, doing the exact thing he actually wanted to do as a creator. Here are some questions that might be helpful for you:

• Questions to help determine your category (entry level vs. experienced, generalist vs. boutique, etc.): What category do they put you in? How long have they been buying from that category? Who else in that category do they consider buying from? Do they use you and a category competitor at the same time? Why? What are they no longer buying from that category?

• Questions to help predict cash flow: When do they buy from you? (Season, month, quarter) Why did they opt to buy elsewhere? Are you a “treat” or a “necessity”?

• Questions to determine buyer objectives: If they’re buying less, are they buying less from the category? Or buying less from you? Are they spending less overall? If they’re buying more, are they buying more from the category or buying more from you? Are they spending more overall?

The answers to these questions may tell you why your customer is willing to stay with you (they feel like the service or product is valuable based on what they pay) or is leaving you right now (the price was a luxury purchase they deemed worth it for a specific campaign or moment, but not for an ongoing relationship). They may also tell you how you might reposition your brand, especially as you learn whether you’re a brand that is easy to substitute with another vendor, be it because of price, convenience, scope, or a combination of the above. They may also tell you a lot about whether you’re fulfilling a want or a need.

I’ve been spending more time creating original content rather than taking on freelance projects, so in essence, my work (newsletters, videos, and podcasts) is my product, and you guys are my customers (whenever I eventually finish creating products to sell). I have an onboarding survey that some of you have taken that tells me a little about you and why you might be interested in my newsletter. But recently, I wanted some deeper insights on make my products better, so I chatted with DenkBot, powered by Delphi. Tyler Denk is the CEO of beehiiv, hence the name, and I thought he might have some insights into growing a media business. I asked about:

• growing this newsletter to 5K subscribers (growth tips)

• thoughtful ways to use newsletter testimonials for social proof

• ways to highlight more folks in this community (hint: it involves the creator database)

• creating greater promotional cohesion across my media platforms

• considerations for building and leading a team as we grow and scale

Overall, it was a super helpful and seamless experience. How would you guys like something like this in place of a 1:1 session? I’m thinking it would be a one-time fee for lifetime access, and it would be trained on everything I’ve written and recorded. So basically, a less chaotic version of my brain in an AI-wrapped bottle.

Thanks for reading, I hope you have a great rest of your week + weekend!