Alex Weinstein
On Growth, Product, and Leadership
A To-Do List Is Not a Strategy

Action bias is a defining quality of many high achievers I’ve met. They detest “philosophizing” - lengthy meetings, PowerPoint decks, strategy consultants who indulge in both. They like learning by doing. In most cases, this bias a powerful asset - it helps get stuff done. With its sheer output, this approach easily beats its polar opposite, talking and not doing much. Action bias has this noble humility: practitioners don’t pretend to know what customers want; by launching things, they learn from them. Then they double down on what works.

Over-emphasizing action bias makes winning seem like a matter of throughput. Hustle, keep plugging away on the to-do list, it goes, and you’re golden.


Ambition: A Journey Of a Thousand Miles can end very badly

This approach has one enormous flaw in it. It gives you very little time to think. Being busy is an anti-depressant; it’s a form of escapism, it allows you to spend zero time on contemplations that are just so very scary: is this thing going to ever work? Are the competitors going to eat us for lunch? Is this the right strategy to be following?

These existential questions are extremely uncomfortable; it feels that they have no answers, and the only thing they can bring is anxiety. This anxiety is caused by the dizziness of freedom1. You have a myriad of things you could be doing, and yet you’re choosing the constraints of your to-do list just because they’re oh-so-comfortable. You choose incrementally higher goals, going for slightly better outcomes, asking the team to be “better day-traders2.”

If you consistently avoid the existential questions, you’re dead. Not in a little trouble, but irrecoverably dead; not right away - slowly, and then all at once.

Past a certain point, most problems cannot be solved by a series of incremental improvements, or by just trying new directions and stumbling upon those that work. You’ve got to select a north star that will make your efforts more than the sum of the parts - those efforts need to add up to a lasting differentiator, a lasting competitive advantage.

One incarnation of this problem is well known: Innovator’s Dilemma, a plague that hits successful organizations that keep doing what they’ve been doing without regard to changing customer needs or market expectations set by competitors. This is what happened to Microsoft Windows/Office with the arrival of mobile phones. This is what happened to eBay with Amazon’s two-day free shipping and outstanding customer service. Both of these extremely successful giants focused on incrementally improving what they already had… until the world no longer needed it.

The other incarnation of it is something I’ve seen in smaller, scrappier organizations that claw towards survival every day. In their world, there are ten times as many things that just must be done for the very basic business to exist comparing what can be done in the next year. In that environment, it’s easy to assume that what we should be doing is painfully obvious - and make a big spreadsheet of to-do’s and just starting working down that list.

Oh noes.

Step Back Please, We Are Trying to fix this

Unlike the big kahunas, if you follow this approach, the end can come much faster - not at the hand of competition, but because you just might not gain enough traction fast enough for the business to become viable. This is particularly true if you raised VC money: the company’s on the clock, and time is playing against you; every choice to work on something has an opportunity cost to work on something else. Make enough “unconscious,” “too obvious to contemplate” choices and that’s it, you’re out of time.

How do you develop a tradeoff function that can guide choices across the organization? Real tradeoffs, where you sacrifice something of value in order to get something else?

  • In marketing, should the team focus on improving the value of existing customers or acquiring more of them?
  • In product, should the team focus on developing a native app, or making the web e-commerce experience better?
  • In customer service, should the team focus on preventing fraud or increasing retention of customers that call in?

Choices like this exist at a functional level, but also at a team level; most of the options are reasonable; leaders in the organization making these choices have a varying level of context for the overall business, as well as personal biases. Without an overriding framework to make these choices, how can you expect them to add up to be more than the sum of the parts?

I’m a proponent of leaders taking a prescriptive approach to solve this, across all levels: storytelling. Write a story of what the future looks like, from three angles:

  • Customers: what pain of theirs you make disappear;
  • Shareholders: how the business makes sense;
  • Employees: what we value and how we work

Write your story in a strategy memo: a document in prose, in full sentences - where you talk about what you envision the next 12-18 months will be for all 3 constituents; what you prioritize and importantly, what you deprioritize.

Once you have a couple of pages, share an early draft with your key stakeholders. If you did a good job, it will cause a stir: OMG, we aren’t going to do X?!? We don’t value Y? But, but!.. That kind of stir is perfect as it does two things:

  • Encourages dialogue between stakeholders to shake out the right tradeoffs;
  • Creates alignment / framework for making decisions for leaders once the choices have been made.

Once you have this document, you can and should convert this into themes, and then make to-do lists out of it. At the end of this process, you can be confident that you’re not “lost in the finite1” - in those pesky details - and your chance of a positive outcome improves.

As a leader, your job is to be the one giving answers to existential questions. You can be confident that the smart people that you hired - that care about the company - are asking themselves those questions all the time. You can acknowledge that these questions exist, and aim to answer them - as best you can - in that strategy memo. Share it widely. Publish a new one every 12 months. That’s what they’re payin’ you the big bucks for.

1: Philosophy nerds, raise your glasses to Soren Kierkegaard with me!
2: Hat tip to Steph Kopa for this incredibly precise term