Emails to a Young Entrepreneur: Flipping Perspective

Day 117 of Self Quarantine             Covid 19 Deaths in U.S.:  133,000

Flipping Perspective

Flip Comic created by David Robinson

“When you travel, you experience, in a very practical way, the act of rebirth. You confront completely new situations, the day passes more slowly, and on most journeys you don’t even understand the language the people speak. So you are like a child just out of the womb.

“At the same time, since all things are new, you see only the beauty in them, and you feel happy to be alive. That’s why a religious pilgrimage has always been one of the most objective ways of achieving insight.”

Coelho, Paulo, The Pilgrimage (Plus) (p. 35). HarperCollins.


Orcas Island, Washington USA, July 4, 2013


Thank you for your kind response to my previous email. I understand that it can be frustrating when someone doesn’t respond to specific questions. One of my colleagues, Professor Ed Lazowska, Computer Science Professor at the University of Washington, was kind enough to share his major insight when teaching – “I never answer the question that a student asks. Rather I seek to understand the misunderstanding or lack of relevant experience that is behind the asked question. I still don’t answer the question that was asked. Instead I give them an exercise (which usually includes a thinking framework) so that they can discover their own answers in their own context.”

What Ed was pointing out is a dysfunction in the gestalt of teacher and student that often inhibits learning. When the teacher is viewed as the source of all answers learning is stopped. Sir Ken Robinson through his many books and TED videos shares the roots of this dysfunction and how we transform dysfunction into vibrancy by shifting from the teacher/student framework to creating rich environments for lifelong learning.

My own mentor, Russ Ackoff, had the gift (or curse) of never answering a single one of my questions.  Rather, he would be thoughtful and then ask me a much better question back. Frustrating? Yes, very. Yet, it was just what I needed to more fully develop my skills of synthesis to complement my analytic skills.

I enjoyed the first seven of your flipped perspectives and the thoughtfulness you demonstrated in looking beyond the easy tacit patterns of daily life.

I am delighted that you connected the perspective shift that a new mother goes through with her newborn and the shift from causal thinking to an observing spirit of inquiry (effectual thinking). I want to talk some more about flipping your perspective in the context of developing an entrepreneurial and effectual mindset.

My daughter experienced what every new mother does when she arrived home and was confronted with her crying bundle of wonder. She quickly realized that Alice can’t tell her what is wrong or what is needed. She shifted from communicating with language to deep observation and listening to the distinction of the meanings of the different cries. She stepped into the first of the essential perspective flips – experience first, make meaning second.

In the beginning, Alice’s crying was just noise. There is only the raw experience and a mother’s jangled nerves experiencing her newborn in distress. Not having discovered the patterns yet, each cry leads to changing everything – changing the diapers, feeding her, holding her, talking to her – anything and everything to get Alice to stop crying. Slowly through many sleepless nights and days the patterns and distinctions of the cries become clearer. That cry means Alice is hungry. This cry means that Alice needs her diaper changed. And sometimes the cry is just about Alice exercising her lungs.

Through observation and many small experiments, mother and daughter begin to communicate. The needs are observed and discovered along with the solutions. Yet, the solutions keep changing as the baby rapidly develops. What worked yesterday to calm her isn’t working today. Pretty quickly a mom changes from the causal thinking of being able to predict, to effectual thinking of what resources do I have ready to hand? What experiment can I run this moment to figure out how to satisfy Alice’s changing needs?

As you learned during your years at the Institute of Design, people are very inarticulate when you ask them what they need or when you talk to them about your cool product idea. They have this disease called MSU (Make Stuff Up). As humans we never want to look or sound stupid, so we MSU. As a result, it is very difficult to find any patterns when we interview and talk to other humans.  When we observe humans in their natural environments, they can be very articulate.

The creativity is in finding those natural environments where you can observe humans who have a problem close enough to what you want to solve for. Once you’ve experienced (observed) the pattern, then you are ready to solve for it. Experiencing first is the foundation of flipping your perspective.

My introduction to this human centered design process occurred on my first visit to the Institute of Design. Instead of having me meet with faculty members, Patrick Whitney had students present their class projects. I was stunned at the breadth and depth of the insights that these first year students generated. It occurred to me that if the students could learn this quickly there were powerful frameworks and ways of thinking that the Institute of Design had learned how to transfer to students.

One of those students twenty years ago was one of your professors, Kim Erwin, author of Communicating the New. As I listened to Kim on her book lecture tour, I remembered her student project research. She wanted to design a completely new way of searching (remember this was twenty years ago before Google existed). She thought about where people had to search and navigate a complex space. She realized that she could observe patrons of the university library, a video store, and the Field Museum of Natural History. Brilliant.

Experience first; make meaning second.

An example of this core flipped perspective occurred at Attenex when we were researching our next product development opportunity:

After we’d gotten cash flow positive at Attenex, we were looking for additional markets. One of the many reasons I was interested in creating Attenex Patterns was so that I could have a personal version to make meaning out of my 8 TB (terabytes = 1000 gigabytes) of digital objects (text, photos, videos) on my desktop computer. While we knew that we couldn’t do a stripped down version of our enterprise level product, we didn’t know what the necessary and sufficient features were for a Personal Patterns.

I pulled in my lead architect, Eric Robinson, to spend a month researching and building a personal patterns prototype. Eric was the hacker (architect) and UX designer. I filled the roles of visionary, UX researcher and hustler. We made good progress in three weeks and a part of my hustler role was talking about and demoing the prototype to anyone I could grab (trying to find a lead customer). Everyone nodded and patted us on the proverbial heads and said “that’s nice,” but there was no energy in the engagements.

We went back to the drawing board and I did a little user research with Marty Smith (one of the lead customers for our Attenex Structure product), a contracts and Intellectual Property attorney at Preston Gates. Not really knowing what I was looking for, I asked Marty if I could just sit and observe him working on contracts for a couple of hours.

One of the lessons I learned at the Institute of Design is that observing people in the wild (their actual work or living environment) is far better than trying to interview them. People make stuff up (mostly because they don’t want to appear stupid) when you interview them and most of the time they don’t really understand what they actually do (tacit knowledge). However, they are incredibly “articulate” when you can just observe them in their natural work habitat.

Marty was working on his third draft of a licensing contract for a very large software company headquartered in our area. There was a lot of client discussion around a patent indemnity clause. He knew that he’d had to rework that clause for a couple of different clients in his previous ten years, but he couldn’t remember which clients nor the nature of the modifications.

Marty’s primary tools are Microsoft Word and Outlook/Exchange. He organizes his file foldering systems (both on the hard drive and in Outlook Exchange) by client and then by year and then by the company name of who a contract was with. He has one giant hierarchical mess. He could have used a primitive Boolean search engine (but his law firm IT group wouldn’t allow such a thing due to corporate security concerns). Even if he’d had a search capability, by searching for “patent indemnity” he would have gotten thousands of hits.

So I watched for thirty minutes as he navigated up and down the folder hierarchy, trying to use the client folder names and the contracting party names to jog his memory for one of the three or four contracts he’d modified in the past. He’d drill down through folder after folder; select a contract; scan through the contract in MS Word to see if there even was a patent indemnity clause; find nothing; and then go back to the folder hierarchy. No joy. So after thirty minutes, he gave up and went back to crafting a new clause from scratch.

I knew I was seeing something important here, but didn’t know quite what. I asked a few business model questions.

Skip: How many times a week does this happen to you where you can’t find a clause you are looking for?

Marty: 3-4 times a week.

Skip: How many times a week does it happen to the other 20 IP attorneys in the firm?

Marty: Probably the same amount for each of us. And we never find what we are looking for so we have to draft from scratch. We try for a while, but never find anything.

My back of the envelope business calculation was the extra cost to clients of $500 per hour * 20 attorneys * 2 hours (search plus redrafting time) * 3 times per week = $60,000 per year. In this one law firm we had $60,000 per year of savings for what I was thinking we might price at $20 per seat. Oops, missed the value equation on this one.

I bounced down the stairs to share my findings with Eric. I described what I’d seen (unfortunately because Marty was doing client legal work I couldn’t use video ethnography to record and analyze his interactions). We realized that the difference that would make a difference was if Marty could do clause level searching rather than try and guess at a couple of keywords that might be needed.

The insights generated from these few hours of relevant observation resulted in a software prototype which generated exciting enthusiasm for a “Personal Patterns” across a wide range of potential customers.

What I am describing is nicely captured in Warren Berger’s A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas. Berger defines a beautiful question as:

“A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change…

“Through the years, companies from Polaroid ( Why do we have to wait for the picture? ) to Pixar ( Can animation be cuddly?) have started with questions. However, when it comes to questioning, companies are like people: They start out doing it, then gradually do it less and less. A hierarchy forms, a methodology is established, and rules are set; after that, what is there to question? …

“Sometimes questioners go out looking for their Why —searching for a question they can work on and answer. The term problem-finding is used to describe this pursuit, and while it may seem odd to go looking for problems, according to the business consultant Min Basadur – who teaches problem-finding skills to executives at top companies— it’s one of the most important things to do for an established business, large or small . As Basadur notes, if you are able to “find” a problem before others do, and then successfully answer the questions surrounding that problem, you can create a new venture, a new career, a new industry. Here again, as Basadur attests, it applies to life, as well— if you seek out problems in your life before they’re obvious, before they’ve reached a crisis stage, you can catch and address them while they still offer the best opportunities for improvement and reinvention.

“Just asking Why without taking any action may be a source of stimulating thought or conversation, but it is not likely to produce change. In observing how questioners tackle problems, I noticed a pattern in many of the stories:

        • Person encounters a situation that is less than ideal; asks Why.
        • Person begins to come up with ideas for possible improvements/ solutions—with such ideas usually surfacing in the form of What If possibilities.
        • Person takes one of those possibilities and tries to implement it or make it real; this mostly involves figuring out How.”

Along with asking actionable “Why” questions and observing humans in their natural environments, participatory research is a good way to experience first and make meaning second. In participatory research, you do the work that you would otherwise be observing. At Attenex, we would regularly have the software developers and product marketing team do the simulated work of an eDiscovery review attorney. They directly experienced the work and the use of our Attenex Patterns tool. Then in debriefing sessions we “made meaning.” We captured the insights from using the tool in order to understand how we could improve the product and the user experience.

The second major perspective flip for the entrepreneur is to reverse the steps of the normal product development process. Most entrepreneurs start with developing their product first and then look around to see if there might be some customers willing to buy their product. Steve Blank’s customer discovery process recommends that you do the customer research in parallel with the product development.

The traditional product development process looks something like:

    • Develop a product
    • Find some early adopter customers
    • Find a larger audience (prospects, the early majority of Geoff Moore)
    • Discover that your causal mindset, thinking and product are not getting you across the Chasm from the early adopters to the early majority

The use of the traditional product development process creates the chasm that Geoff Moore describes. Since the entrepreneur is so focused on the product and not on understanding that the economic buying customer is the Early Majority, the first customers reinforce what the entrepreneur already knows. By not building the product for the early majority, the new venture collides into a wall of customer indifference. Most traditional ventures fail at this stage unless they have very understanding investors who can fund the rebuilding of the product to address Early Majority needs.

Figure 5 Geoffrey Moore’s Technology Adoption Life Cycle

David Robinson and I realized that the entrepreneur must stand the traditional product development process on its head and reverse the steps. In his book The Seer, David describes the progression through the Nine Recognitions to develop the Entrepreneur’s Mindset:

“The tasks (a study, an action, an exercise) will help you develop new patterns of thinking and seeing. To that end, you will also find within the narrative a few related practices. The practices are useful in preparing your mind for the flip to a new way of thinking. This process is like riding a bike: you can read about it and think that you know or you can get on, start pedaling and learn to ride. The practices and tasks will only help if you do them; they can’t help if you don’t engage with them. To reiterate: perspective shifts are not an intellectual exercise; they are dynamic processes. Shifts in perspective are intuitive, experiential engagements made conscious through action and reflection. Effectual entrepreneurs are like artists: engaged in dynamic, fluid creative practices. Get on the bike and ride. Challenge what you think you know. Open your eyes to possibilities. Allow yourself to make meaning of your experiences after you have them. It is, after all, how your brain works so you might as well begin by dropping the illusion that you know something before you encounter it – it’s an important skill for an entrepreneur.”

Reversing the steps – Mindset to Product

You need to reverse the traditional product development steps to:

    • Develop a questioning, observing and inquiring MINDSET (flip your thought process to effectual)
    • Find and create the AUDIENCE for your product or service
    • Identify which members of the audience will be your paying CUSTOMERS
    • Develop the PRODUCT

The next step in the entrepreneur’s flipped perspective is creating your audience.

An audience is the superset of the humans that might eventually become customers. I am part of a huge audience of fans who are excited about the 2014 Super Bowl winning Seattle Seahawks football team. I talk about them all the time with my family and friends. Yet, I am not a customer of the Seahawks – I don’t purchase tickets to their games nor do I purchase any of their jerseys or clothing. There are millions of us who are in the Seahawks audience and only 100,000 or so who are direct customers buying tickets for a game.

Linda Holliday, CEO of Citia, describes their challenges innovating in the traditional publishing industry by repurposing business books. They did some wonderful work with their reimagined books, but couldn’t find any customers.  And the publishers didn’t help them find customers because publishers have no idea who actually buys their books. They pivoted and realized they needed to find authors who already had a large audience. Their first foray with Snoop Dog led to a very successful relaunch of their technology. It was very easy for Citia and Snoop Dog to make Snoop Dog’s audience aware of the new interactive book.

Your first task as an entrepreneur is to discover or create your natural audience.

At a recent Meetup on Lean Content, Kelsye Nelson described her flipped perspective process of creating her company, Kelsye and her co-founder met at the “Seattle Daylight Writer’s Group” Meetup that Kelsye had started to peer encourage other writers. The format of the Meetups is that the group would gather (20 to 100 writers) and write together silently for 45 minutes. At the end of the time, the writers could elect to share their work. Sometimes no one shared and at other times everyone wanted to share.

In the networking sessions that followed, the writers discovered that they had different strengths, weaknesses, likes and dislikes for different parts of the writing and self-publishing process. Pretty soon participants were discovering that somebody really liked to edit others work and another liked to do cover art. They realized that within the group were all of the skills and resources needed to create the online resource exchange for self-publishing authors.

The concept of was born. While they had a built in community to support them, Kelsye needed to build an audience with her limited resources before starting a company. Using her marketing expertise she started a social media Lean Content (content as a process) effort to build her audience. She started posting ten to twenty curated inspirational quotes a day about writing through Twitter and Facebook. About every ten posts she would send out a sign up for her mailing list.

Within a few months she had 2000 active readers of her posts and she had her audience to pre-launch where authors can hire out the skills they don’t possess. Their product was a simple brokering of talent that required minimal development. As her customer base and revenue stream grew she was able to hire developers to build the real product.

What is important in your journey with your newborn venture is to regularly practice the first two flips:

Experience first. Make Meaning Second

Yours in entrepreneuring,

Skip Walter

This entry was posted in Content with Context, Emails to a Young Entrepreneur, Entrepreneuring, Flipped Perspective, Learning. Bookmark the permalink.

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