Why your goals fail

Wisdom from the trenches / startup myth-busting

This is a newsletter about building a software company, written from the trenches of building one.

I write brief essays to reflect... and to counter all the startup myths and “hacks” peddled by influencers looking to make a quick buck.

This week’s myth: “Adopt Objectives and Key Results (OKRs) to get your team focused on what matters the most.”

The myth in real life

We just completed our first productive OKR planning session after trying in vain for ~2 years.

I’ve read so many OKR and goal-setting books - Measure What Matters, Four Disciplines of Execution, Toyota Kata, High Output Management, Atomic Habits…

And yet, we couldn’t get any of them to really work for us.

I also advise a few early-stage startups. Whenever we discuss their goals and work cadence, I always find a certain incoherence to the goals they present.

For example: A company sets go-to-market OKRs around a freemium offering AND their outbound sales process. These are two different go-to-market motions (and products) for a pre-product-market-fit startup with a go-to-market “team” comprised of one founder who is also fundraising.

In theory, their OKRs make sense: They fit the OKR formula! But they’re impossible to achieve, don’t make sense in combination, and will ultimately lead to a lot of pain. They are bad goals.

So how do you get to good goals?

Getting to good goals is more important than the goal system you use. It is, after all, upstream. The effectiveness of your goal system depends on finding the right goals in the first place.

Focus upstream on the “narrative” first

This time around, my company first agreed on what I call “the narrative” before we got into the details of goals and goal-setting.

What is the narrative?

It’s a story about what our company does - who we serve, why they choose to buy from us, their journey with our product/service, and where we’re headed as a business.

In my experience, the narrative starts as a long Google doc with a lot of abstract bullshit (“QA managers choose us because we unparalleled service”) that the team fights over until it becomes concrete (“QA managers at tech companies that have recently adopted test automation software find that their team wastes 10-15% of its time trying to re-create bugs when the automated tests indicate something breaks, and they come to us because we provide video replay that reduces their time on re-creating bugs by 95%”).

The process of de-bullshitifying a company’s narrative is the best alignment tool I’ve ever experienced. We did it with our leadership team. It required multiple difficult, hours-long discussions and debates over a few weeks.

You’ll debate what your customers are really looking to achieve, how your tech can solve it and why you’re different from competition, where you are today and what’s possible in the near- and long-term. You have to get real, make trade-offs, and be explicit about your assumptions.

After you have the narrative, you have the context to set good goals.

Until you have your narrative, you might as well let a feral cat write your goals.