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How to Hit Aggressive Milestones - Lessons from Monster House

Work with Josh

I hate deadlines. But quite often in tech, deadlines are not just preferable; they’re necessary. Consider the MVP: holding yourself to a date on the calendar ensures your minimum viable product doesn’t become a maximum viable product. And milestones are critical to alignment across teams, departments, or even companies.
Luckily, there was an incredible television show in the early aughts that teaches us everything we need to know about hitting a tight deadline with audacious objectives and limited resources.
Monster House aired from 2003 to 2006 on the Discovery Channel. Every week, host and foreman Steve Watson would assemble a small and motley crew of builders, plumbers, electricians, painters, and others (who had never worked together before) to transform a boring regular home into something spectacular. The homeowners get to pick the theme (their only involvement); one week, it was space-themed, and they incorporated a crashed spaceship and pneumatic tubes into a single-story California ranch. Other themes included dinosaurs, ancient Egypt, and gangsters.
It’s worth watching a couple of episodes here on YouTube.
How were they able to get such incredible work done within such restrictive constraints?

1. Understanding the 'Who' and 'Why'

The first step in the Monster House method involves ensuring the entire team understands for whom they're building and why. They’d meet the homeowners and hear a bit about why the particular theme was chosen. Each person on the build team got to hear from the family directly and hear their hopes and anxieties. In my experience, this understanding is crucial. We’re not just building a product; we’re crafting a solution for real people with real needs. This empathetic approach fosters a deeper commitment and a stronger sense of purpose, which is indispensable when working against the clock.

2. Crafting a Clear, Shared Vision

Next, the team collectively sketches out what they’re going to build. A week isn’t long enough to truly change every detail of the house. But each of the teammates is an expert in what they do, and they’re called on to visualize (literally - with drawings) what they think can be accomplished in a week to maximize impact. Why do this visually? Because words, no matter how eloquently penned, can be misinterpreted. A shared visual representation – be it sketches, diagrams, or mock-ups – becomes a communal language, transcending individual interpretations. And, combined with getting an empathic understanding of the end users, this is where you create alignment.

3. Locking in Team and Timeline

In Monster House, the timeline (one week) and the team (unless someone storms off in a rage) are fixed. Because “adding people to an already late project only makes it later,” we should think of our fixed deadlines as having fixed teams as well, even if our timeline is longer. After all, anyone who comes in late will lack the context and the alignment previously established. It's also a declaration that the team assembled is the right one and that the timeline set is achievable. We’re fostering confidence and urgency, crucial components for success under tight deadlines.

4. User Stories and Task Lists

This is where the rubber meets the road, and we define scope and commitments. First, as a team, write out the user stories we expect to support when we’re done. And, as a team, make sure this is truly as minimal as possible. The entire project is a stretch goal. No need to make it more of a stretch. Second, turn those user stories into a punch list of tasks. Why a punch list? Builders like those on Monster House use a simple list of things to be completed, nailed up somewhere conspicuous, to ensure everyone knows what they should be working on. Here are some hard-won lessons about how to set tasks:
  • Each task has a single person responsible.
  • Try and make sure each task is independent, can be completed by one person, and lacks any dependencies. Barring that, make sure there are no dependencies outside the project team.
  • If the team, individually and collectively, can’t enthusiastically agree that the tasks are achievable, then they aren’t achievable. Don’t bully your team into failure.
I’ve created a handy template here - feel free to copy, share, and make it your own. And just like a builder’s paper punch list, make sure this one is visible to the team and that everyone is updating it continually.

5. Creative Problem Solving Under Constraints

An unexpected catalyst for creativity lies at the confluence of a fixed deadline and teams. The constraints imposed by such conditions are not hurdles but are, in fact, what ignites your best thinking. You don’t truly understand your challenges, or those of your customers, during the planning stages—this only emerges from the doing. When confined by these boundaries, teams transform constraints into opportunities for creative problem-solving. We see this often on Monster House, where the final product exceeds the expectations of the initial vision. 

6. The Finish Line: Done or Not

As the due date looms, a hard truth emerges: you're either done or you're not. The beauty of Monster House’s method lies in its unapologetic realism. It forces teams to monitor progress closely and descope where necessary. It's about being agile and honest, ensuring that if a scaling back is needed, it's done without surprise or last-minute chaos. And regardless, when you hit the due date, celebrate! You and your team just accomplished something really cool and really out of the ordinary. 🥳

The Allure of the Monster House Method

Why does Monster House have so many great lessons for us, 20 years later, building software products? Because it works and because it’s fun.
The Monster House method is not just a set of steps; it's a philosophy grounded in clarity, commitment, and pragmatism. It speaks to a truth I've seen in all my years of work: the path to achieving great things on tight deadlines is not through chaotic heroics but through disciplined, well-orchestrated teamwork.

Why This Method Works

  1. Empathy and Purpose: Understanding the end-user fosters a sense of purpose that can drive teams to exceed expectations.
  2. Visual Communication: Eliminates ambiguities, aligning everyone's understanding and vision.
  3. Commitment and Urgency: Locking in resources and timelines creates a focused, high-energy environment.
  4. Ownership and Expertise: Assigning tasks based on belief in individual expertise encourages accountability and quality.
  5. Realism and Agility: Accepting the reality of deadlines and being prepared to adapt ensures progress without panic.
Monster House was a show about transformative results under challenging constraints. It's a testament to what can be achieved when a team is aligned in vision, committed in action, and enthusiastic in execution. In my experience, whether in technology, entrepreneurship, or any field requiring innovation under pressure, this is a framework not just for meeting deadlines but delivering products and solutions that are timely and extraordinary.