The Hardest Thing Is Prioritizing

Kwindla Hultman Kramer
2 min readApr 17


So, what’s the hardest thing day in and day out at a startup?

That’s an easy one.

Prioritizing the right things, all the time, ruthlessly, is the hardest thing.

And it’s the hardest thing on both day one and in year ten of a startup’s journey.

Very early, when you’re searching for product market fit, everything is an experiment. You don’t have enough data to know what experiments to try. You probably have a really long list of features to build, marketing channels to test, target customers to talk to, and everything else.

You also have to run your experiments long enough to give them a chance to work, or at least to show you something useful.

But every minute you spend on an experiment that’s not working is time stolen from another experiment that might work.

As you grow the shape of the challenge changes, you have more data about what works for your company and what you should be doing. Maybe never enough, but more. However, now you have a coordination problem.

There are more people doing the work and making sure that every person in every role is always working on the most important things becomes the challenge.

People want to work on things that matter, but getting everyone the right information and the right support at all times is hard. Like really, truly, unintuitively hard.

And it only continues to be hard as a company scales. Which is why there are so many business books with titles like High Output Management and Measure What Matters, and The One Minute Manager. All of which are fundamentally at their core about prioritization and the communication and processes that support prioritization.

But I’ll stop here and ask, do you agree? Is prioritizing well the hardest thing, day in and day out, about growing a company?

Today’s music is “Billie-Doo” from the 1956 Thad Jones album “The Magnificent Thad Jones.” Billy Mitchell, Barry Harris, Percy Heath, and Max Roach.



Kwindla Hultman Kramer (formerly Pluot), Oblong, Media Matters for America, AllAfrica -