If You’re Not Surprised, It’s Not Useful.

by jennifermshoop

As per my new routine, I’m taking stock of my key learnings from this past week:

1.  “The biggest thing I’ve learned about providing direction is that you do it with your ears and not your mouth.”  This quote comes from Silicon Valley darling Kim Malone Scott, in a great article reflecting on lessons learned from managing people at Apple, Google, Dropbox, Twitter, and Square.  This is tough advice to apply; work is busy, and good managers are efficient.  And listening and altering plans based on what you hear can be time-consuming and occasionally schedule-thwarting.  But she makes great points about how to lead and build a productive, happy workforce.

2.  “If you’re not surprised, it’s not useful.”  I can’t remember where I heard this, but I jotted it down as a good piece of wisdom with regards to testing a product.  (It has “Lean Startup” written all over it, so I’ll chalk it up to one of the brilliant speakers from that event.)  I think the big takeaway here is that, as a product owner, you need to spend your time looking for what’s not working or what’s working out in a way that differs from your expectations, as those are the areas that need your attention.  If all is going to plan, you’re not growing, or your not pushing yourself, or your not measuring the right thing.

3.  “Pitching is a narrative art.”  One of the most painful but beneficial parts of participating in an accelerator (Moneythink was in FFWD’s inaugural class) was rehearsing my pitch.  A few things I’ve learned:

-Slap stats are a good way to grab attention

-Use an unexpected turn of phrase to evoke a smile (our CEO Ted is good at this; he often uses phrases like “put those benjamins in the bank,” which softens the audience and conveys our youthfulness)

-Connect the project to your own passions/motivations (I still struggle with this as I’m not one of the co-founders and our founder’s story is particularly illustrative — of our lean approach, of our youthful energy, of our big-hearted compassion, of our rootedness in the urban landscape — but time and time again, folks remember the passion and commitment of an organizational leader that has communicated his/her personal connection to the mission)

-Don’t shy away from sharing your BHAGs (big, hairy, audacious goals): I initially felt a little sheepish sharing the huge goals we had for ourselves; as a relatively risk-averse individual, I would have preferred to share our realistic targets for the next two years.  Push yourself to talk big during a pitch; paint the vision.)

-End with an ask.  A pitch is about asking for something (usually money), so be up front and ask for what you need at the end.  The pitchee (er, catcher?) is expecting it.

-But most importantly: tell a story.  This is the oldest adage in the book, but people will really hang onto your words when you get the connected to a user experience, to the story of why the app was created, the story of why you use the product.  Whatever it is, tell a story.

4.  Design is about moving from an existing state to a preferred one.  This is the most gorgeous definition of design I’ve ever heard, and I picked it up at the Cusp Conference earlier this year, an incredible design event that invited me to speak about design thinking in a non-profit setting.   I occasionally feel that there is no end to “design” — what’s the difference between strategy and design, for example, in a business setting?  (I’ve heard IDEO talk about “organizational design” and “business design,” for example.)  At any rate, this is about as good a definition as I’ve ever heard.  It’s nestled right up there with a definition for “poetry” that I picked up in an undergrad “Intro to English Lit: Beowulf through Shakespeare” lecture class I took as a freshman at the University of Virginia.  I had dreaded the class at first — it was a huge “gut” class with hundreds of kids in the lecture hall, and we’d then break out for discussion sessions with TAs once a week.  But the lectures — my God, the lectures!  They were absolutely phenomenal.  I could barely see my professor from the back of my 500-person auditorium, but I will never forget her defining poetry: “poetry is a distillation of emotion into a preconfigured form.”

5.  “A startup is a human institution developing something under conditions of great uncertainty.”  This is an Eric Ries classic — another great definition to keep in the ether.