Obama’s “A Promised Land” applied to Product Management
By: Wei Jia Chen
Tags: Product Leadership, US Politics, Product Management, Leadership, Organisational Culture

A Product Land

Yesss, I did it.

I’ve written a piece that pretty much sums up that running for President and running a product line are grounded in the same principles.

Either that or I’m a product geek that sees product in everything I do/ watch/ see/ eat.

Last year I drafted an unpublished product piece that I entitled 5 Lessons from The Witcher applied in Product Management (and Life). I was eager, back then, to write about about how fighting monsters wasn’t so dissimilar to fighting stakeholders (I kid, all stakeholders are awesome! :).

The hype of The Witcher had passed before I got around writing it up, but interestingly enough I still kept the soundbites that I had jotted down as I was binging through episodes:

My failed attempts at drafting a piece after binged watching episodes of The Witcher

But I digress.

Why A Promised Land?

Like many product folks, I had compiled a reading wish list with a 2021 resolution to read voraciously this year. Having released his book in Nov 2020, Obama’s A Promised Land ended up being one of my top 2021 picks.

So on to it. Why Obama would make an awesome product manager.

Probably the coolest president of all time

#1 Know your constituents / customers, and serve them

Obama was a people’s man. The people’s man. Chapter after chapter (and mind you there’s probably 10+ chapters before he actually became President), there’d be snippets that gave insights on how Obama, in his pre-Senator days, spent days, weekends, months, door knocking, visiting communities, speaking to, and more importantly, listening to his constituents about the problems they faced.

During his time as a presidential candidate, he would do the same — spending Saturdays visiting ethnic neighbourhoods/ Sundays at Black churches; traversing from the rich in the “mansion-filled North Shore” to Chicago towns that were poverty stricken. Listening to his “customers” was what led him to design a message, a campaign position, that resonated with the masses on a shared cause for change.

Thinking back to product, it’s pretty much the same. We live in a product led growth era, where it’s critical to know, listen and understand your end customers and build a product for them. Marty Cagan in his recent book on building Empowered product teams aptly put:

Product teams exists to serve our customers, in ways that meet the needs of our business.

Oh hello Marty. Looking snazzy.

How to know your customers?

The first thing that comes to mind on how one would get to know your customer may start with someone saying “Hey, let’s conduct some customer interviews”.

This process would probably involve segmenting the right customers, setting a series of (non-leading) questions around the product or problem statement, setting up meets with users or merchants, and post-interview collating notes for next steps etc. etc.

Whilst there’s no substitute for meeting real life physical human customers, the reality is that most product teams may not have the resources, time, nor dedicated teams to conduct customer interviews for their thousand/millions of existing customers.

So what are some of the other ways to know your customers better (if you don’t have the time or resource for interviews?):

Find customer proxies: A tip that we proffer to our product guys — find customer proxies. Customer proxies are the equivalent of (in Obama’s case) speaking to the leader of your local council, the person that interacts enough with the locals to provide a strong collective viewpoint of the constituents. In the case of product, customer proxies could be — e.g. our Customer Happiness team for consumers — these are your product frontliners, the team that day-in day-out are on the phone/ email/ whatsapp/ telekinetic communication with your customers, and usually, the most critical of customers. Another customer proxy for our merchants is our Sales team. Who better to know the key problems of our merchants than the Sales team who are pitching your products. Speak to one Sales rep and it’s like you’ve spoken to 10 merchants.

A tip that we proffer to our product guys — find customer proxies. Customer proxies are the equivalent of (in Obama’s case) speaking to the leader of your local council, the person that interacts enough with the locals to provide a strong collective viewpoint of the constituents. In the case of product, customer proxies could be — e.g. our Customer Happiness team for consumers — these are your product frontliners, the team that day-in day-out are on the phone/ email/ whatsapp/ telekinetic communication with your customers, and usually, the most critical of customers. Another customer proxy for our merchants is our Sales team. Who better to know the key problems of our merchants than the Sales team who are pitching your products. Speak to one Sales rep and it’s like you’ve spoken to 10 merchants. Scour customer reviews on the app store/ play store: I do this at least once or twice a month as a checkpoint on how users are responding to our products. Recently, one of my check-ins uncovered a severe bug in our Android app that unfortunately failed to raise an alert in our errors logs. Raising a Code Pink (coined), our teams hopped on quickly to nip it in the bug (punned). Bear in mind, that usually only the most scathing reviews would make it to the app store reviews wall. As a product manager, you need to bite the ego and remind yourself:

“Your most unhappy customers are your greatest source of learning” — Bill Gates

Vega Lambardt, whoever you are — you are my biggest source of learning and I thank you for your witty feedback which has spurred us to do better as a product team. If you’re reading this, I’d love to give you some Fave eCashback.

Product usability and survey tools: Interviewing customers have also been made harder through the pandemic, where in no way is “meeting someone for a customer interview” top of anyone’s priority list. Our Head of Product Design had discovered and introduced Maze to our team, where we were able to do rapid product validation and usability testing and get data driven results for product decision making. Nice.

#2 Evangelise

When Obama started his campaign, he was terrible at crafting responses in debates, or answering questions in forums with his constituents. Having been a professor and writer, he would actually try to answer questions by offering detailed, academic, long winded responses.

In a postgame conversation with David Axelrod, Obama’s then Chief Strategist, he was given a harsh critique:

“Your problem,” he said, “is you keep trying to answer the question.” “Isn’t that the point?”, I said. “No, Barack,” Axe said, “that is not the point. The point is to get your message across. What are you values? What are your priorities? That’s what people care about. Look, half the time the moderator is just using the question to try to trip you up. Your job is to avoid the trap they’ve set. Take whatever question they give you, give ’em a quick line to make it seem like you answered it… and then talk about what you want to talk about.” “That’s bullshit,” I said.

The most effective debate answers or product pitches, are usually those that are designed to evoke emotion (ideally alongside facts), identify the common enemy (in the product world this could be — the competition, the bad user experience, bad business numbers), and create a vision of something memorable.

I remember when I first stepped into a Product Lead role, one of my first call to action was to draw up a competencies framework to build growth in the team. I had premised our framework one of Marty Cagan’s coaching tools and thought, hey, this fits pretty well with what we are trying to achieve.

And here is how we judge, I mean evaluate the competencies of our PMs. Happy to share the full version to any aspiring product leads.

However, one often debated competency was this vague, intangible, yet in my mind an undoubtedly important skill called evangelism. Questions from the team was aplenty:

“How do you define product evangelism?”

“How do you measure evangelism?”

“Why is evangelism important in the product development cycle?”

I will always remember this quote from Maya Angelou:

At the end of the day people won’t remember what you said or did, they will remember how you made them feel.

Story time.

In a sea of 20 pitches, which would you remember?

Last quarter, we introduced a new format for setting our product roadmap.

We were tired of roadmaps prioritised in silos, had problems communicating or had to communicate repeatedly our priorities/ timelines/ roadmap, we had constant challenges on our priorities (being a regional product team, every country or business stakeholder questioned — Why did things appear to take forever to launch? Why should we prioritise a user experience feature over features that would drive business numbers?).

We don’t see departments as working silos, but rather, encourage congregation of the collective minds and work as a #oneteam (one of our strongest Fave values)

We experimented with our inaugural Product x Business Huddle (Version 2020). A full day session designed to present a series of pre-prioritised pitches to a collective of group of product leaders, business leaders and management. The session was aimed to align our North Star, set our business and product strategy for the quarter, drive awareness of our priorities and encourage debate on the products our business would be built on.

Our “prioritisation” led us no less than around 20 pitches throughout the day. We had by any means possible made the entire day as engaging as possible with pockets of interactive polls, robust Q&A etc…. but even the most attentive would falter at one point or another.

Whilst all pitches by all our teams were amazing (and I mean that genuinely, I was impressed by the standard delivered by the teams), there was one that stood out — an imagery of a football field.

“Imagine a football field filled with people who’ve come to watch a match, that’s the amount of users that you’d miss out on if you don’t deliver on X product”, one of our PMs had highlighted.

Product Managers have to be clear communicators and inspiring orators. A non-negotiable skillset.

Obama is often “speechmarked” for certain styles that could be applicable to evangelism of your product:

A focus on powerful words – “A change is brought about because ordinary people do extraordinary things” Master of metaphors – “Braving icy currents and storms to come” Over preparation and self-preparation – Obama is known for writing down long drafts on yellow legal pads over days for the perfect delivery. Test driving speeches and concepts with key advisors — I often do this with team leaders whom I trust to give scathing but honest reviews of my concepts or product ideas.

As a PM, your life is full of pitches. Pitches to the technical team. Marketing team. Business teams. Your own product team. If you believe in the impact of your products, you have to evangelise.

#3 Find your Ted Kennedy, or be a Ted Kennedy

Best buds 4 life.

Ted Kennedy was a political legend.

Not only was he one of American’s longest running Senators, he was also brother to a President (John F Kennedy), a U.S. Attorney General and Senator (Robert F. Kennedy) and father of a Congressman (Patrick J. Kennedy). Practically U.S. royalty if there ever was one.

He was also instrumental to Obama’s success in more ways than one.

In his book, Obama shares his months before his decision to run for President. He was young (47 at the time), inexperienced by a mile, a rookie, and full of self-doubt, uncertain about the move to presidency. He had spoken to a range of advisors, including Ted Kennedy, who was the push that Obama needed to throw his hat in the race.

Famously, Kennedy told Obama:

“The power to inspire is rare. Moments like this are rare. You think you may not be ready, that you’ll do it at a more convenient time. But you don’t choose the time. The time chooses you. Either you seize what may turn out to be the only chance you have, or you decide you’re willing to live with the knowledge that the chance has passed you by.”

Months later, Ted Kennedy endorsed Obama in a move that would change the course of the 2008 presidential elections. By openly endorsing this rookie President, he effectively secured Obama’s nomination for presidency:

“There was another time, when another young candidate was running for president and challenging America to cross a New Frontier. He faced public criticism from the preceding Democratic president, who was widely respected in the party. Harry Truman said we needed “someone with greater experience” — and added: “May I urge you to be patient.” And John Kennedy replied: “The world is changing. The old ways will not do … It is time for a new generation of leadership.” — Ted Kennedy

As a product leader, who you endorse and what you decide to endorse can make or break your team, your culture, a whole presidential election. It’s important to remember that by sheer fact of your position, your voice and your actions carry weight and influence, and play a critical part in shaping the future.

Endorse your team

As a product leader, one of the most important things you can do for your team is to endorse them. Endorsing them means trusting your team, and trusting that you have hired these bunch of smart creatives to be able to solve problems instead of handing them solutions.

In an old but gold Culture Deck by Netflix, Reed Hasting famously advocated for a culture to lead with context, not control. An amazing question to ask yourself when a team member comes back to you with what is seemingly a shitty idea is “What context do you have, that your team member might not have, to have generated this result?”. Conversely, as a product manager, you might ask the same question, “What context did I get, that my manager did not, that led me to generate this result?”.

Endorse Change

As a product manager or leader, it’s easy to endorse the status quo, succumb to the experienced, or please stakeholders. It’s harder, to embrace novel ideas, endorse “rookies”, or adapt to changes in business climate or culture.

Product leaders often need to carry with the the mark of humility and reset themselves by adopting a beginner’s mindset (a principle I reminded myself often when building products during the covid pandemic).

I recall in the early days of the pandemic, we did the painful move of throwing half year roadmap out the window. We were running an offline to online business in a world where the offline was shut to the world. Our status quo, was challenged. We had to reset ourselves to endorse change, set ourselves to a 30 days roadmap and daily/ weekly check-ins. As the covid situation shifted, so did we as a product team, had to shift, experiment, fail, and try again.

#4 Rally your troops to a vision

The less known woman behind Obama’s campaign

Edith S. Child. A name that few would know unless you’ve read Chapter 5 or live in the South Carolina town of Greenwood.

Obama tells of a time when he was simply having a bad day. An endorser refused to fund him unless he travelled hours to a town called Greenwood to meet the local council there. He had also opened the papers to a bad headline of himself. It was a rainy day, torrential with the type that blew off your umbrella and got you soaking wet.

When he got to the town of Greenwood, the turn up was a measly group of less than 20, the situation less than inspiring for a presidential candidate.

As Obama was navigating through the meet, a lady from the crowd shouts “Fired up!”. Obama was rightfully confused.

Again, she shouted, “Fired up!”.

The small crowd started responding, “Ready to go!”.

And as the chant cuts the mood, Obama himself was getting Fired up! This chant from an unknown local lady in Greenwood was apparently a tradition to rally the team up at any team meeting, sporting event, etc. and would carry on to inspire the presidential campaign slogan.

It’s amazing how a single person could through their enthusiasm and excitement, mobilise an entire nation.

As product manager, we wear many hats. We are the problem solver, the collaborator, the mediator, the challenger, the gatekeeper, the innovator, the evangelist… and in the sea of human interactions across the 100+ stakeholders we deal with weekly, we play an critical role inspire, to motivate, to rally across teams towards a shared cause (amidst the product development bumps and failures).

Product management was never made for the faint hearted. It takes a kind of grit, resilience and a fire within to wake up in the morning and know you might fail when you’re creating something new. But you do it anyways because you know you’re going to create something life changing.

Are you fired up? Are you ready to go?

I know I am.

Happy 2021 to all the people I trust and love.

WJ