Provocations.

Moneythink is a learning-oriented organization.  I can say this with confidence because I have been tasked with and resourced to tackle some pretty big questions, to float solutions, and then to report back on what we’ve learned.  I work hard to ensure that every item on my roadmap is linked to a “what we want to learn” statement; my CEO is wont to ask me to target learnings for various undertakings and pilots; I have a living document called “The Vault” where I chart user insights and problems.

I love this.

Recently, the rest of the senior leadership team huddled up to think about articulating this orientation a bit more sharply.  I had drawn up an organizational snapshot that identified, at every level of the organization, the questions that we are tackling at each layer — the provocations around which we orient our work.  At the highest level, for example, we are asking: How might we build the financial capability of American youth?  We have core solutions we’ve advanced in response to this, and we will be measuring our outcomes against specific goals.  At the tech exec level, I own the provocation: “How might we use technology to drive the long-term financial outcomes we’ve identified for ourselves?”  I have my own solutions to this question.  When I bring my product manager on board, I will have him or her own the question: “HMW drive engagement with the smartphone technology we’ve built?”

I like this strategy because it resonates with perhaps the best bit of advice I’ve picked up this year: “Lead by owning the questions, not the plans.”  How powerful, humbling, and clear is that imperative?  My impression as a younger member of the workforce was that senior leadership was dictating strategy from the top-down.  This model highlights a more empowering model of leadership: we set the questions, we push our staff to answer them with proposed solutions to the best of their abilities, and we measure their efforts.  If things aren’t working, it becomes pretty clear that new solutions are in order.

HCD vs. Mission.

I just enjoyed the most exhilarating and exhausting two-day workshop visioning around the future of our technology solution with our tech partners.  It was exhilarating in that taking a step back to look at the big picture and to dream really big about where we can go reminded me ever more poignantly of the mission I am working toward and how my day-to-day struggles pertain to those big social goals.  It reinvigorated a love of the product we’ve developed, almost made me nostalgic and proud of the amount of thought and effort we’ve put into this solution.  It made me feel unalone in my work on technology strategy, where I can often feel like an island given the small nature of our organization.  (And, to quote John Donne, no man is an island.) It was exhausting in that it required a lot of mental gymnastics, looking at our work across a big canvas and then diving down to study the finest minutiae — which actions should trigger which push notifications and how complex those schemas are (or aren’t) to implement; how we can scale back desired analytics reporting features into an MVP version (i.e., which metrics matter); whether or not the addition of a student’s school beneath his/her name is a valuable addition and the level of visibility different users should have, full-stop.  It was a lot of drilling deep and getting into the weeds, a lot of pulling and sharing of information, a lot of long pauses as we puzzled over potential solutions — and then a lot of sweeping up into Big Dream Talk.

It was all-around awesome.

And yet.  There was a cloying voice in my head that kept asking: “Shouldn’t we have the kids here?  Shouldn’t we be re-starting the process we undertook when we brought IDEO.org in to help us?  Is it OK to vision and build off of what we’ve already built without going back to the source?”

And yet.  We have learned a lot about our students and how they relate to our technology.  We know that there is a direct correlation between number of likes/comments received on a post and overall performance in the app.  We know that they “just want to know someone is listening.”  We know that certain types of classrooms are more optimized for tech adoption.  We know that students often are unable to see themselves as “savers” or as financially empowered because they do not believe they have the resources to do so (and by resources, I literally mean that they do not think that they are financial beings because they do not have enough money).  We know that students spend the majority of their free cash on food purchases and shoe purchases.  We know that they like to “flex” (a term new to me) their cash, to show off the stash of dollars that they have.  (What this suggests is problematic — lack of access to accounts; lack of understanding of security risks; desire to emulate what they’ve seen in pop culture, especially music videos; association of self-worth with cash holdings; etc.)  We know that they love emojis (the vast majority of posts are accompanied by them).  We know that they like points for points’ sake.  We know that they like to unlock surprises.  We know all of this based on tests we’ve run, conversations we’ve had, posts kids have made, and data analysis.  So, I came around to the view that I did have the students’ voices present in the room — just mediated, perhaps, by a lot of thinking and data analysis and reflections.

There was another strain at hand.  There were the clear comments, observations, and insights we’d gleaned (as outlined above) that pointed us in certain feature directions.  And then there were the mission-level, organizational-level hopes we had.  If the end goal is to help students make better financial decisions, there are certain…breaks? disconnects? between making a product that is fun and sticky and making a product that drives and reflects the performance of specific financial behaviors.  And often these things just don’t match up.  Is it OK to test a feature that may be more vitamin than painkiller?  Do we always need to shroud the vitamins in painkillers?  Is it OK to have a high-level, org-level idea informed by best practices in the field and to implement that feature even if users haven’t asked for it?  And, dare I say it, even if users have suggested the opposite?  Let me give you an example: we know that the social nature of our solution was one of the key value propositions for our students.  Time and time again, when asked why they used the app, they would say: “I liked seeing what other people were buying,” “I liked comparing my results to others,” “I liked that someone was listening.”  And we’d also see, in the data, that the more comments and likes they earned, the higher the retention rate.  And we’d notice that the more kids that were posting, the more likely that others were to post.  These are fairly obvious and even expected observations, but they are meaty and not-to-be-ignored, nonetheless.  There is something sticky and powerful and even natural to kids to be sharing information and to seek out and receive affirmation in the form of digital likes.

And yet.  When we’re thinking about our work from a financial outcome perspective, one idea we’d had was to include a “financial meter” modal that might pop up when students log in each week.  They answer three questions: did you save today? (respond to this by tapping a single dollar sign; two dollar signs; or three dollar signs to reflect the relative level of saving); did you spend money today? (again, three dollar sign options to reflect the amount of saving); and how do you feel about your finances? (with three or four possible smiley faces).  We think this would be fascinating in that we could gather aggregate trends about whether or not our kids are saving more and their overall affect around their financial status.  This would be powerful data for us as a program and would have the added benefit of making students feel like the tool is a bit more personal, a way to think about and store financial information about themselves.

And yet.  They haven’t asked for this; in fact, they seem most attracted to sharing moments.  And this would be the opposite.  How do you reconcile the HCD approach, listening carefully to the wants and needs of the user and only building to their specs, vs. a big mission around prevention?  Does HCD only work best when we have a painkiller solution on the table?  What about the vitamins?

Evolution.

My husband works for Groupon and has developed an incredible amount of insight into sales strategy and operations.  They are a truly data-driven company, and the kinds of analysis they’re conducting and the level of data they’re leveraging is astounding.  Drilling a level deeper, he’s constantly bringing home fascinating tidbits around optimized sales tactics — from the time of day, to the length of call, to the tone of voice, to everything in between.  He has even more mind-blowing insight around incentivizing salespeople to hit their targets, motivating a young salesforce, and — in general — being a bad-ass manager.  (He may be the only person I’ve ever met that was a born manager.  He’s a force.)

But one of the most powerful pieces of advice he’s brought home came from one of his managers, who said:

“If you’re doing the same thing at the end of the year that you were doing at the beginning of the year, you’re not doing your job.”

What a powerful charge for personal, professional, and organizational growth.  Our CEO often says: “We want to obsolete ourselves.”  It took me awhile to come around to this phrase: it’s intentionally aggressive and even challenging to digest.  And yet.  For a non-profit trying to solve a big problem, evolution to the point of extinction is the ultimate goal.  Solve the problem not just fully but fundamentally — at the root — and you won’t need to be around anymore.  This, of course, requires a massive vision and confidence in our ability to literally change the fabric of our culture in substantial and meaningful ways.  It may mean mandating financial education; it may mean bringing better, more affordable products and services to the un- and under-banked; it may building pop culture references reflecting greater fiscal responsibility and financial mindfulness.  It probably means all of these things and more.  But at the root of all of this is the assumption that, in order to deliver something powerful, we must continue to evolve and grow and tackle and iterate until the problem is totally eradicated.

Though my husband’s boss was not speaking in terms of our organizational mission, I see the thread that ties here.  And I also see the incredible power in charging your employees to push themselves to grow, to continue to solve new problems and create new efficiencies, to resist the desire to rest on one’s laurels.  In a fast-paced company like Groupon, it’s a problem if your staff aren’t changing given the rate of evolution the organization continues to see.  I love the idea of instilling this sense of expected change and growth up front.  For one thing, it prevents the likelihood that folks will rebel when things change too much or too quickly; they will have been onboarded with the expectation that things will and should and must change.

So – I digressed a bit from my earlier goal of sharing 5 learnings per week.  I may oscillate between one big learning or five smaller ones.  This blog, too, will evolve.

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

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.