Tell me a story

How teams make leaders.

Introduction. Do you know why this book? Sometimes your boss picks the wrong thing to tell you (that) you suck at.

Once upon a time, a meeting was on my calendar with my boss. And I was given some direct feedback that I could have been a better storyteller.

Every day that feedback fueled my focus on rebutting this feedback. I said nothing and was laid off six months later. I felt defeated, deflated, and a failure. This was a low point in my career. I had young children and was the only wage earner in my home. The emotional damage was gut-punch level and was more than a setback. It was a failure to convince leadership that I could add value.

One day, I met with Scott Snyder in a Starbucks. We had a few conversations about this new company called Mobiquity. I was intrigued but needed clarification on the startup because this being my 4th startup, was I going down a riskier path financially? My instinct was this seemed like an exciting opportunity. But I was sold once Scott explained the Wawa thing he was working on. Scott asked me what I would do if I had a chance to work on Wawa’s ‘App.’ I was clear about what I thought, and Scott smirked. You will find out later why.

Because of that, I took the job because of the opportunity to pitch and work on a brand I grew up with, worked in the stores, and loved like lots of people. Going to ‘Red Roof,’ the corporate HQ, was like a key to the kingdom tour at Disney. A little starstruck and excited, it began a 10+ year labor of love for a love brand.

Because of that, my journey to be the best storyteller could be continued or restarted. Begin a journey like this started with fundamentally understanding the human that would suffer by what we made a solid experience.

Because of that, we needed to do the research. Fundamental research with real humans doing things and transacting. That led to learning, questioning, understanding, conversations, and endless curiosity about everything that happens in a Wawa. The whole company was fascinating, from the parking lot (the most dangerous place at noon any day of the week) to the vendor trucks, the fuel dispensers, chargers, the free air, inside the store, etc…… (and so on)

We finally had an experience that tells the Wawa story for the first time outside the store, in your pocket on the phone. Finally, Wawa meets the standards Wawa has and continues the brand promises Wawa has made for over 50 years.

And every day after that, my storytelling got better. Every opportunity we pitched worked as a team. Of course, winning and losing were always possible, but over-prepping and many other techniques helped hone my story craft.

Finally, learning that lifelong learning is core to improving my storytelling, I dedicated this book to that boss 11 years ago who told me I was a lousy storyteller. And to my team, Leaders don’t fall out of the sky into leadership roles. They are, in general, made by teams around them. I am forever grateful for the chance my team gave me to lead.

arc of uncertainty
investigations, three-legged stool plus models got to markets ownables

Notecard: Arc of Uncertainty. What is the arc of uncertainty? I have drawn it several times. I define it as that process of understanding that starts with a level of not understanding that, through a process, becomes a certain understanding. When working on the design of anything, there are natural patterns of uncertainty. Think of it as the early knowledge subject to clarity and more information that builds on a solution. That follows the idea that initial discovery and immersion in a subject area or requirements effort requires an amount of suspended disbelief. The amount of suspended disbelief is unknown for some time. As the unknowable is known, the arc bends toward certainty. I learned through a set of projects early at Mobiquity that teams had a significant amount of uncertainty. What is interesting about the arc is the consistency of it over vastly different jobs to be done, opportunities to explore, and solutions to be defined.

What about the mission? What mission are we on? Often, you need a mission. So what is the mission? What is the why of what we are making? So early uncertain teams need a mission. Here is a link to examples of missions. Every uncertain team needs to have a mission.

  • Why are we doing this? What are we tasked with accomplishing?
  • Who stands to benefit, and why is that? One or two big things.
  • What will this accomplish if it is successful? And if it fails, what will we learn?

There needs to be on the mission a set of conversations on deliberateness, divergence, and diligence. The immersion in the topic of the work needs to be complete and focused on who will suffer from what we make.

There is a destination, theoretically, at the end of the arc, but honestly, the journey, as with many destinations, is the best part. The certainty gained in the process of discovery, immersion, ideation, iteration, and conceptualization along the arc can be the best part. The final thing arrived on, or the solution created, is great if it’s great. The journey to get there sets up any effort with a solid first step.

most of these are not the arc of uncertainty

  • Beginning
    • Interviewing
    • March Fourth
    • Bad Storyteller
    • Visiting HQ Boston
    • Wawa the dream job
    • Weather channel again dream job
    • Build a design team
    • Getting shit done
    • the snake in the bathroom
    • my door desk
  • Middle
    • the marathon
    • the shit show tour
    • the undoing of bad choices
    • we got this
    • you can do anything for a few years
    • mentors
    • double the company in three years
    • a death in the family
    • sharp elbows
    • the story of acquisition
  • End
    • another death in the family
    • a pandemic
    • remote pitching
    • remoting and emoting
    • winning without
    • a hex
    • the end of an era
    • the undoing of an integration
    • the winding down of intention
    • another death in the family
    • the story making of a pitch
    • the beginning of the end of the beginning
  • Things or concepts over the years
    • Box 0 – It’s where your process starts.
    • 5 slide rule – the story of storytelling with simple rules of thumb
    • arc of uncertainty
    • silent utility
    • fuckeduptioning
    • get shit done
    • #keepmoving
    • context orientation
    • poise presence posture
    • macro to micro
    • narrowcast v broadcast
    • beginning middle and ends
    • strategic benign neglect
    • DFIU
    • The Magic Wand question
    • 5 key interview questions (fear, best/worst, title, exit magic)
    • murder boards
    • improvisational storytelling – the concept that over-prep lets you improv when it’s showtime
    • Anxiety — uncertainty x powerelessness over intuitive emotional awareness of your humans
    • How research drives insight and insight drives innovation and innovation can transform the human experience and it always has
    • between stimuli and response there is a space, a place to choose a moment of growth and freedom.
    • Wisdom — time + experience / failure learnings