Tiff's Treats and Tim Brown

"When Tiffany Taylor and Leon Chen were college sophomores at the University of Texas [1999], she stood him up for a date and delivered hot-from-the-oven cookies to apologize."*

Leon loved the cookies and convinced Tiffany that she should start a business delivering fresh-baked cookies. In the very beginning, they took orders on their cell phones and baked cookies in an apartment—the first prototype of the business that would become Tiff's Treats.

If you've never eaten cookies from Tiff's Treats, I am sorry for you. Here in Austin, it's common to see small white cars with the Tiff's logo driving around delivering happiness wherever they go. On the last day of my internship at Chesmar Homes in 2017, the team had Tiff's Treats delivered to the office—any excuse to get those addictive cookies was fine with me.

Entrepreneurs and designers dream of epiphanies like the one Leon and Tiff had, but it's not always that easy. One (if not the only) consistent way to generate and execute on good ideas like that is through design thinking, as I've learned in Tim Brown's Change by Design: How Design Thinking Transforms Organizations and Inspires Innovation.†

Tiff's Treats is the sort of idea that came as an epiphany but could easily have come from an exercise in design thinking:

Scenario 1

I own a bakery, and my customers lovemy chocolate chip cookies. Some people come in during lunch to buy them for the office, some buy them for parties; there's even an older man that visits me every Sunday before the Patriots play to buy a box for him and his friends.

However, the foot traffic to my storefront isn't exceptional. I'd like to increase the sales of my delicious treats—my business doesn't have a website, so maybe that will help people navigate to our store. We might even start a blog, create a Facebook page, or buy web advertisements and hope for the best.

I'll start by contacting my favorite designer—Diego—to see if he can help me build this website. I know I want it to be blue and pink, just like the colors in my storefront, and it needs to have three pages: a homepage, an about section, and a contact page. I already have an idea of what it should look like, so I'll draw that out for him on paper and allow him to create the rest based on my idea.‡

Scenario 2

I own a bakery, and my customers lovemy chocolate chip cookies. Some people come in during lunch sometimes to buy them for the office, some buy them for a get-together; there's even an older man that visits me every Sunday before the Patriots play to buy a box for him and his friends.

Instead of writing a creative brief, building a website, or buying advertisements right off the bat, I'm going to make this a design question:

How might we increase cookie sales for my bakery?

I spoke to my designer friend Diego about this, and we had a long conversation. After many hours of brainstorming, I remembered how pizza joints started delivering in the 1960s—everyone orders pizzas now! What if I started shipping my cookies in a box directly to someone's home or office at a low cost and in a very short amount of time?

That's Tiff's Treats, a successful business (as far as I know) operating in multiple cities around the United States.

Easier said than done

It's not as easy as asking a good question and then brainstorming for a while, but in a way, it is. In the above scenario, it's not far-fetched that a design thinker and a bakery owner could have come to this conclusion with a couple hours of thinking, conversing, drawing, and brainstorming.

The key here is the reframe. Instead of choosing a random solution to try and going all-in on it without any information, you ask a "How might we...?" question and allow ideas to flower in the early stages.

Types of thinking

There are two phases of thinking during any design project: divergent and convergent, in that order.

The key for a "How might we...?" question to work, according to Tim Brown, is to allow for divergent thinking in the early stages of a project. This means lots of ideation, brainstorming, and prototyping.

In the bakery scenario, divergent thinking might look like a list of ways to increase sales of cookies:

  • Create a loyalty program for repeat customers

  • Start advertising on Facebook

  • Send a flyer to everyone in the area

  • Host an event at your bakery

  • Sponsor a conference or event

These might all be viable ideas that work in some capacity and they're all testable. You could create a loyalty program for your repeat customers and easily see whether they get excited about it. You could start with a small budget advertising on Facebook and see if it leads to anything. You could send a flyer to one zip code on a very small budget and track sales with a coupon from the mailer.

When you come across a promising idea, then you can turn to more convergent thinking: If delivering fresh, warm cookies right to someone's door is enticing, then how can we execute on that idea at a large scale? What will that cost, who can we serve, and what will we charge? How can we make that experience seamless and convenient? Convergent thinking closes in on all of those details as you move to the implementation phase.

Key Lessons

Turn requests into design questions.

Rather than go to a designer and say, "Create X, Y, and Z," take initiative of the project and ask some form of the question, "How might we...increase cookie sales/obtain more enterprise clients/encourage high school students to read/aid homeless veterans?"

Allow for divergent and convergent thinking.

On a tight budget and timeline, it feels risky to allow for a divergent brainstorming to happen at all, but generating and testing lots of ideas in the early stages of a project will lead to valuable insight later on.

* Source: https://www.cookiedelivery.com/About/Our-story.aspx

† Standard disclaimer for when I write about a book:

I may get different ideas from this book than you got or that the author intended. If you'd like to find out whether I got it all wrong, buy the book. I'd love for you to support their writing.

‡This is a "creative brief" of sorts—a document that outlines project specifications and restrictions for a creative.

Diego Segura