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.
The planning fallacy has influenced the design of my upcoming Path to Repeatable Sales program. We meet for one hour a week for three months. It’s a longer than average training program, and that’s on purpose. I wanted to build something that sticks with you as you define your hypothesis and test it by booking, running, and tracking sales calls. You’ll inevitably get stuck, frustrated, or blocked – but we’ll have time to address and get you running at full speed again. If you’re swirling on sales or want to accelerate your path to predictable revenue, the next step is a quick call with me.
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.
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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.
grow revenue ON YOUR TERMS
- Early Sales Cohort Program: A new, more cost-effective way for founders to get all the curriculum and coaching needed to reach sustainable, recurring revenue. The next cohort starts on September 16. Have questions? Let's chat.
- Sales Consulting: If you’re looking for completely custom 1:1 support to grow or refine your startup’s sales process.
- Trainings for Accelerators: Sales workshops for early-stage founders, from someone who's been there.
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Caroline Fay
