How To Plan a Vacation Like an A+ Product Manager

Tommi Forsström
4 min readAug 1, 2017

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Let’s plan a holiday! Allow me to show you how a seasoned product management veteran would go about it, applying outcomes-first thinking.

Picture from the Expert Product Managers’ private beach & yacht club

What do I want to get out of my vacation?

I think I’m in need of a max chill vacation where I get to sit in a palapa, pretend to be a beached whale, and will never be further than 100 feet away from yummy meals and people who will place cold beverages in my hand.

Where can that be achieved?

Hmm. Mexico, Jamaica, Hawaii… These other places have Zika, so I’d rather not risk it. I think my safest bet here is Hawaii.

How do I get there?

I live in New York City. Not only is Hawaii far from here, but there’s an ocean in the way. I should probably fly.

What do I need to make it happen?

  • Book hotel
  • Book flight
  • Hop in cab to get to JFK
  • Get on plane
  • Sit tight
  • Get off plane
  • V Chill

See What I Did There?

The magic you just observed above was me employing “Outcome Thinking” 😎.

It’s exactly what the title states: You start from the transformative effect you want to see happen and work your way inward. Ultimately, the tactics take care of themselves.

This is how exceptional companies operate. They have a strong and clear vision that is manifested in highly actionable mission statements.

These mission statements pave the way for the strategy the company employs to pursue the outcomes, which then distills into the tactics it executes.

BINGO!

This sounds super obvious, right? Every company has at least tried to define their mission, vision and values. You probably have a drawer full of mouse pads with words like “dynamic”, “trustworthy” and “customer-obsessed” printed on them, as per your company’s set of values.

Still, if you observe most companies in action, you’ll see a combination of vague, unactionable mission statements and a strong tendency to chase opportunities in their immediate vision.

This often boils down to a Dwight D. Eisenhower quote my mentor and former boss Catherine Ulrich loved to use quite often:

“I have two kinds of problems: the urgent and the important. The urgent are not important, and the important are never urgent.”

Executing on a grand vision takes a ton of discipline, patience —, and periodic, calculated steps in the seemingly wrong direction.

To go back to my vacation example, if I would’ve just hopped in my car and started driving to where it looked like the weather is warm, I probably would’ve ended up hanging out on the Jersey Shore or Coney Island. That would’ve been full-on tactics-first execution.

A middle ground would’ve been diligently deciding on the longterm goal and destination first and jumping right into execution. In my example, I decide to travel to Hawaii, which is west of NYC. But the first step I take is going east from my Manhattan home to JFK. I’m literally traveling in the wrong direction because I know it to be of strategic benefit to my longterm goal.

This is only possible because I’ve worked my way in from the outcome and I’ve committed to diligently going through the layers of abstraction to get to where I need to go.

How to Apply Outcome-First Thinking for Product Management?

Tools for this type of thinking are quite often built for grand scales: running multi-billion dollar enterprises and operations of a massive scale.

But like most great frameworks of thinking, it does scale down quite gracefully.

My favorite resource for making sure I diligently go through the motions in planning things out is actually for community organizing and not big business:

I keep coming back to that article and the really tangible examples in it to make sure I think through all the layers on any initiative I embark on.

Even if you’re kicking off planning a new feature on a product, you can follow these steps:

  1. What is the transformation you’re going for? (Vision)
    Eg. Increase the retention of our product.
  2. What are you doing and why? (Mission)
    Eg. Improve the onboarding experience to shorten the time to first action.
  3. How will you know you did good? (Objectives)
    Eg. Conversion up by 5pp.
  4. How are you going to get there? (Strategy)
    Eg. Replace janky ol’ tooltips with fancypants new overlay thingy.
  5. Who needs to do and what exactly? (Tactics / Action Plan)
    Eg. Design gonna design, tech gonna tech etc.

Easy-peasy, right? Yet quite often I see people starting from just looking at a product and jumping straight to conclusions on what they see on the surface as immediate improvements.

Sometimes that’s okay. Maybe I would’ve been perfectly happy on the Jersey Shore.

If you’re going for big transformations and major impact, that rarely happens by just attacking the first obvious opportunity.

Take the time to think about it starting from the outside.

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Tommi Forsström

VP of Product at Teachable. Ex-Shutterstock, Splice & Produx Labs / Insight Partners. Lives in NYC, originally from Helsinki, Finland. http://forssto.com/blog