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The planning fallacy


Nearly everything takes longer than we expect.

It’s the recipe with a cook time of 25 minutes that somehow took you 90.

It’s the construction site down your street that was supposed to be finished last year.

And it’s definitely every project that you take on at your startup.

It’s not you. It’s a real thing. It’s called the planning fallacy.

Iconic economists Daniel Kahneman and Amos Tversky discovered this cognitive bias, which holds that humans are really, really good at underestimating how long things take.

Even when we try to predict when something would get done if every single thing went wrong… yep. We underestimate that too.

It’s important we embrace this truth, and pad our schedules and expectations accordingly. Especially when it comes to the biggest project that any startup faces: product-market fit.

I don’t think I’ve ever heard one founder utter the words: “I want to figure out our sales playbook in the next twelve months.” Much more often, they tell me it's goal they've set for the “next few months.”

Building out a repeatable and reliable sales process just doesn’t happen in that amount of time.

I wish it did! It will take at least twelve months of concerted effort. Heck, some of the most successful B2B startups ever estimate it took them two years or more.

It takes this long because there are a number of intensive steps you must follow to get there:

  • Defining a hypothesis of who has demand for your product
  • Testing that hypothesis through sales
  • Tracking insights from those sales calls, and isolating issues with your hypothesis
  • Updating your hypothesis, and testing it again
  • And continuing to iterate until you are telling a precise sales story to one defined buyer type, resulting in a reliable close rate

Each one of these steps has a great deal of work within it. More crucially, the testing and iteration process, driven by real market insights, simply cannot be bypassed. It takes as long as it takes, and there are no shortcuts (other than getting really, really focused on this as your #1 priority).

Many founders are tempted by an alternative approach: brute-force pushing your product into the hands of almost any buyer. This will extend the amount of time it takes you to reach product-market fit, as you’ll be selling to too many different buyer types with no systematic way of gathering insights that lead to a repeatable, scalable sales playbook.

Don’t fall prey to the planning fallacy. Or if you do, let it be on that half-finished closet organization project you've been chipping away at, or something similarly low stakes.

It takes longer than anyone would like to build a repeatable sales model. The more you embrace that, the more you’ll make real, undeniable progress.


upcoming events

"My Product's Not Ready" and five other myths about early-stage sales

Wednesday September 3 at 12 ET

​If you've found yourself mysteriously blocked on sales despite your best intentions, this workshop is for you. We'll cover the common myths that founders hold about selling and reframe them. You'll leave with new perspective, agency, and tools to win deals and manage the mental game of selling. Register here.

This is Extra Extra, a newsletter about the tactics and mindsets that drive early sales. I’m Caroline Fay, an exited social impact founder who’s spent my career launching and selling new products. I help non-traditional tech founders build sustainable, recurring revenue.

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Caroline Fay

67 West Street #GP24, Brooklyn, NY 11222
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Extra Extra

Extra Extra is a newsletter about the tactics and mindsets that drive early startup sales. I’ve helped dozens of startups get results like a 50x in repeatable revenue and a 400% lift in sales calls per week.

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