Founders

Why We Always Start Our Projects With Roadmapping

Why We Always Start Our Projects With Roadmapping 1456 816 James Knight

In my ten years of working in the tech industry, I have seen startups consistently wasting $100K+ and 6 – 12 months building the wrong product with the wrong team. 

Without strategic roadmapping, startup founders risk misalignment, wasted resources, and a diluted product vision. It’s a shortcut to startup chaos.

Unfortunately, most founders don’t use roadmapping. Instead, they write out a spec, take it to a dev shop, and trust whatever number they tell you. That’s what these founders did. 

One of the significant problems of not starting your project with roadmapping is that there’s a strong chance you put the essential pieces of your project last. 

When building new and innovative things, we are, by definition, exploring an unexplored space. If someone else is already doing it, then we’re not really entrepreneurs. We’re just copying.

So, when we are trying to do something new or do something in a new way, by definition, we’re exploring the unknown. Too many projects start by confirming the known things and then moving on to the unknown stuff at the end. 

In this article, I will cover the following to prevent you from doing this:

If you already see the light, I recommend roadmapping your project before spending a single dime or making a commitment with anyone. 

Roadmap Your Project


What is Roadmapping?

Roadmapping is an organization’s strategic planning process to outline a clear and visual path for achieving its goals and objectives over a specific time frame.

With product roadmapping, this process involves determining the requirements needed for taking a company’s product vision to a market-ready product. 

Product roadmapping involves:

  • Defining your targets.
  • Exploring risks and identifying key questions.
  • Sketching your customer map.
  • Strategically aligning these targets, questions, and maps.

When you don’t Roadmap your product

If a piece of software has one new innovation at its core, that could be an innovative application of technology, an innovative technology all on its own, or it could be applying a solution that’s worked in another industry to our industry, some innovation, that’s new. 

But it’s got a bunch of other things, too. That piece of software has all of the boilerplate, as we call it, all of the admin admin, the login, the settings, and the stuff that every piece of software has. 

If we don’t roadmap and identify the important bits first, we’ll often start with the stuff that we already know and just confirm it. 

Wasting money and time

So, we’ll build a login for our new software, build settings, and create all of these things that have been made before. And then, at the very end of the project, we’ll get to the hard part. 

At this point, we’ve already spent 80% of our budget. We’ve already wasted 80% of the time that we thought we were going to take this whole project, and when we get to this last 20%, we realize now that this innovative part is hard, and it might take another 80%. 

And it might cost another 80%. So our budget is 50% over, and we will be six months late. All because we did all the stuff we knew we could do before doing the stuff that we didn’t / weren’t sure we could.

This applies not only to technical or product pieces but to anything unknown when building a new project. If no one will respond to your emails because they’re not interested in what you’re selling. You probably shouldn’t build it.

We should make sure that the people who are going to buy our product will buy it before we build it and invest a ton of money in it. 

We roadmap so that we can identify the risks, bottlenecks, and questions that need to be answered before we go and start building things and spending money.


How Roadmapping Helps Visionaries

James Knight, No Nerds CEO conducting a roadmap workshop.
No Nerds Roadmap w/ Death Row Records 2023

Another reason we roadmap is that there are a lot of projects that start with this Polaris in mind, this North Star that founders at pointing towards, and entrepreneurs are by nature visionary. 

Founders have big visions; they have this idea of an idealized product they want to bring to market. And that vision is sometimes huge. And, a lot of times, they’ll go and base that vision on competitors in the market. 

They’ll say, well, WhatsApp has this feature. So we need that feature. Instagram has this feature. So we need that feature. Gmail does this. YouTube does this. So we need to do this too.

That’s great, and it’s great to have that Polaris, but a lot of times, we have budgetary or timeline or go-to-market constraints that need to be satisfied in 30 days and 90 days in six months, 12 months.

And so what roadmapping does is it helps us identify that Polaris, put it on the board as the Northstar that we always want to point towards, but also it helps us identify off ramps.

For example – what can we do in 30 days? What would success look like in 30 days?

Strategic roadmapping answers these questions and risks we identified and allows us to actually get this thing built while at the same time gaining some interim success along the way as we continue marching towards that Polaris.


Why we use Workshops for Product Roadmapping

We use workshops as part of our process, as workshop mentality has so many benefits when it comes to product roadmapping. 

A good example is when you and your team have been working on a problem for months, maybe even years. We often use workshops to sit down with people who have had this brilliant, innovative idea stewing in their brains in some capacity for five-plus years.

When you have an idea you’ve been thinking about for five years, that idea matures and evolves in your head. Our memories are relatively faulty. And so even with a partner that you talk to every day, there will be elements of your plan in your head that have evolved in a different direction than your partners. 

There will be conversations you had with partner A 12 months ago that the two of you remember that you did not have with partner B six months ago when they joined. And as a result, they have been operating with a different assumption this entire time. 

And it never occurred to you that this could be the case because you and Partner A are so sure about that from the conversation you had.

Workshops help with Brainstorming

No Nerds Head of Design taking notes in a roadmap workshop
No Nerds Head of Design – Roadmap Workshop

One of the main reasons we workshop is to get everyone in a room together and have them take a turn in the hot seat. We use this to reach into each of their brains, into this giant cobweb network of ideas they’ve connected over the last six months, 12 months, or even five years.

We will then pull that cobweb out thread by thread, lay it out on the table, and compare everyone’s individual roadmaps to ensure they align.

Partners who sit next to each other and talk about their project every day, when they come into the workshop, have things they realize about what they’re working on together that they’ve had misconceptions about for years.

From first-hand experience, it’s a very magical process to sit down and pull those ideas out bit by bit.

Visual Components help us understand

The final piece of our process is the use of visual components. When we do a roadmap, one of the things that we’re doing is we’re going to lay this vision for your product out visually. 

A lot of times, when people are preparing software projects, they write out the specs. They write out the product document, the features they want, and why they want them, and then research and link to textual articles. 

And the problem there is that roughly 65% of people are visual learners. If your spec is just written and not visual, there’s a 65% chance that the person who is supposed to receive that spec will misunderstand it. 

So, this visual component part of roadmapping is extremely important. If we depend on written descriptions of what we want to do, we are guaranteed to have misunderstandings and misconceptions about our product.


The Value of Having Goals and Off-ramps

Goals and off-ramps are an essential part of our product roadmapping process. When used correctly, they often allow us to utilize shortcuts (good ones) and demonstrate traction cleverly. 

Using shortcuts to your advantage

Roadmapping helps us identify places where we can cut corners, not in a bad way, but as effective shortcuts. A well-thought-out strategic roadmap lets us identify things we can do quickly for free or by using off-the-shelf products. 

Depending on what our off-ramps are and the questions we’re trying to answer in those off-ramps, we might be able to get away with not building a big, giant, custom two-year software project. 

Instead, we could duct tape together a Shopify-type form and Convert Kit to get 90% of the product in a testable fashion, get it out the door, and start answering those questions. 

Demonstrating traction for growth

It’s a lot easier to get people and partners on board, whether investors, other co-founders, or full-time hires, that we’re trying to target as players and want to convince them to leave their cushy jobs and join our risky startup. 

And it is a hell of a lot easier to get those people to join our team in whatever capacity they will join when we have this demonstrated traction in place.

And that traction doesn’t have to be that we have a two-year custom software project in the market selling itself. It could be duct-taping together these three pieces of off-the-shelf software. And what we got out of that was a letter of intent signed with a large enterprise.

That allows us to show our product is worth it by saying, “Hey, we actually have ten paying customers here in our local market.” 

Sure, they’re paying for a service instead of a product, but that service mocks out what the product would do. So, we now have some evidence that building the product will be worth it.

Having those sorts of off-ramps built into the roadmap allows us to prove some success and secure additional support through investment, co-founders, full-time hires, etc.


A Roadmapping Success Story

I’ve spoken in-depth on why you should start your project with strategic roadmapping. To back it up, I want to share a recent prime example of how this works.

BlueVerse – A Healthcare Startup

When BlueVerse came to us as an early-stage startup, they didn’t have a penny to build anything. They managed to scrape together enough for a 5-day roadmap workshop with us. Without spending a dime or writing a single line of code, the results speak for themselves:

Before Roadmapping
  • BlueVerse had an enormous vision, described in a single 2-page Word document.
  • The startup came to us without design, experience, or funding to build anything.
  • BlueVerse was looking for design & development partners to help build their vision.
After Roadmapping
  • Complete vision turned into a 12-month, step-by-step roadmap.
  • Clickable prototype in hand after just 5 days, ready to sell to customers.
  • Took roadmap and prototype to investors and closed a 6-figure seed round w/ $0 development costs.

No Nerds saved us from burning tens of thousands of dollars building something custom by showing us how to reach our targets on our own. They spent an entire hour arguing that we shouldn’t hire their team. You’d be stupid not to sit down and map your product out with them.

Mason Still, CEO @ BlueVerse

Roadmap Your Project

4 Things Founders Can Do to Keep Their Process Fresh

4 Things Founders Can Do to Keep Their Process Fresh 1200 844 James Knight

As a company grows, its processes most scale.

Or, they can decay.

Here are 4 things you can do to make sure your processes scale alongside your company.


🧍‍♀️ 1. Focus on People

99% of process problems start with people.

The right team following bad process will get the job done.

The wrong team with perfect process will fail anyways.

Any process audit has to start by understanding your people.

Start with your team, not your tools.


👑 2. Start at the Top

The people usually blamed for process are the ones at the bottom

But process comes from the top.

When investigating a failing process, always start with leadership and work your way down.

The bottleneck is usually near the top of the bottle.


⏳ 3. Explore the Fractal Hourglass

At every process level, there are four types of people involved:
– Stakeholders
– Executive
– Manager
– Contributors

These form an hourglass shape.

The SEMC Hourglass chart
The SEMC Hourglass

1. The top half is concerned with Strategy.
2. The bottom half is concerned with Tactics.

☝️ On the top half of the hourglass, the Executive sets the strategy and communicates it up to one or more Stakeholders.

They decide where the ship is headed.

If the destination is the wrong one upon arrival, they’re the ones at fault.

If the Strategy has failed, the Executive has failed.

👇 On the bottom half, the Manager receives the strategy from the Executive and translates it into tactics for the Contributors to implement.

They decide what direction the ship should point to reach its destination.

If the ship doesn’t arrive at the correct destination, they’re the ones at fault.

If the Tactics have failed, the Manager has failed.

This pattern starts at the top and repeats itself at each process layer.

A Fractal Hourglass.


🌹 4. Make Lifecycle Charts

When investigating process, we often start with our org chart.

But to establish clear processes, we need to understand our process lifecycle.

Consider the following questions as we move down the Hourglass:
– Where does a need originate?
– Who prioritizes needs?
– Who is responsible for describing the need to the team?
– Who is responsible for conceptualizing an answer to the need?
– Who is responsible for executing that concept?

And then, on the way back up the Hourglass:
– Who is responsible for making sure the deliverable matches the concept?
– Who is responsible for making sure that concept responds to the described need?
– Who is responsible for making sure the described need actually matches the original?

Visualize the answers in Lifecycle Charts.

Chart them out. Then assign someone to each seat and establish accountability.

☝️ As companies grow, processes age. As they age, they can mature.

Or they can decay.

To keep your processes fresh, make a habit of reviewing them.

And then:

🧍‍♀️ 1. Focus on People
👑 2. Start at the Top
⏳ 3. Explore the Fractal Hourglass
🌹 4. Build Lifecycle Charts


Early-stage founder?

Unveiling Customer’s True Pain: 4 Questions for Founders to Uncover Real Problems

Unveiling Customer’s True Pain: 4 Questions for Founders to Uncover Real Problems 1200 844 James Knight

If I had asked people what they wanted, they would have said faster horses.” — Henry Ford


Successful startups must talk to customers. But as Ford said, they can’t just ask those customers what they want.

They have to “excavate the problem.”

Here are the 4 types of questions founders can use to identify their customer’s true problems.


1. “Last Time” Questions

These are the best way to kick off a customer interview.

“Tell me about the last bag of coffee that you purchased.”

Grounding the customer in a real experience helps you get real feedback. It keeps the customer focused on their lived experience instead of spouting off speculation.

Focusing on experience can uncover pain points like “horses smell,” “they’re expensive to feed,” and “stables are large and expensive.”

Failing to do so gets you “faster horses.”


2. Generalizing Questions

After describing a single experience, generalizing questions can help the customer move to another—potentially different—moment in time.

“Is that typical when you buy coffee?”

Now the customer is scanning their memory for other times they bought coffee, looking for anything particularly noteworthy.

These questions are critical when you feel like the first instance the customer brought up may not be indicative of their typical experience.

Imagine your customer telling you that the last time they bought a bag of coffee, they were on vacation in Hawai’i, and bought one right on the plantation.

That’s probably not their typical experience.

Generalizing questions help your customer move from one experience to another. But they can also kick them into speculation mode.

If your customer begins waxing poetic about what “buying coffee” means to them, it’s a good time to bring them back down with our next question type.


3. Focusing Questions

When the customer’s head is in the clouds, it’s time to bring them back to Earth.

Focusing questions help us do that.

Imagine your customer is saying that where a coffee comes from is the #1 quality they look for when at the store.

We can bring them back to their lived experience by simply asking:

“The last bag of coffee you bought, where was it from?”

Often, customers are less principled than they believe themselves to be. Focusing questions help us cut through the platonic bullshit and come back down to their actual actions.

Sometimes we’ll also notice inconsistencies between specific experiences the customer describes.

To analyze those, we can use…


4. Comparison Questions

Comparison questions compare a specific instance with another.

Like generalizing questions, they can be useful for identifying inconsistencies between what a customer believes to be true and what they’ve actually done.

They can also help us uncover the context that drove changes in behavior.

If your customer typically only buys coffee from local organic roasters, but last weekend they bought a tin of Folgers at the grocery store, understanding why those instances differ is key to identifying what drives your customer’s decisions.

“This time you said you bought coffee from your local roaster, but last time you just but a tin at the store. Why?”

Maybe they were sick. Maybe their mother-in-law was in town. Maybe they were behind on rent.

Lateral questions can help us identify the real “why” behind each of these experiences.


💯 Talking to customers is a must

But we can’t just ask them what they want.

Successful founders know how to “excavate” their customers’ real problems using four types of questions:

  1. “Last Time” Questions: Triggering the customer’s most recent experience.
  2. Generalizing Questions: Motivating the customer to scan their memory for similar, noteworthy experiences.
  3. Focusing Questions: Cutting through the customer’s speculation to ground them back in a specific instance.
  4. Comparison Questions: Forcing the customer to justify why they acted differently between experiences.

Early-stage founder?

Why do Founders Often Struggle to Be Heard?

Why do Founders Often Struggle to Be Heard? 1024 655 James Knight

The MICE quotient is an invaluable tool for understanding the story you’re telling.

It’s a concept that comes from fiction but applies equally well to sales and marketing.

By understanding the four MICE conflicts, founders can turn their vision into a captivating narrative.

Good stories are the same — in fiction, non-fiction, or copy. They all revolve around conflict.

The MICE quotient describes the four primary sources of conflict you can use:

1. 🗺️ Milieu
2. ❓ Inquiry
3. 🦋 Character
4. 🌋 Event.

Let’s explore each one:

🗺️ Milieu conflicts focus on the setting of the story.

A Milieu story begins when our character(s) enter a new place.

It ends when they exit.

In Milieu conflicts, the struggle to leave entertains and educates us.

For products, Milieu stories are about our customers returning to a place of comfort.

Something has changed, and they’ve entered a new, scary world.

Our product helps them return to the one they came from.


❓ Inquiry conflicts focus on a question.

An Inquiry story begins when our character(s) discover a question they don’t know the answer to.

It ends when they find that answer.

In marketing, Inquiry stories are best used to entice the customer into reading more.

We open the loop with a question they’re dying to know the answer to (“But how?!”).

We close the loop when we’re ready to move on to the next big question.


🦋 Character conflicts focus on character transformation.

They begin when our character becomes dissatisfied with their life or their circumstances.

They end when the character transforms into the person they want to be.

Character stories are best used as the over-arching narrative our customer moves through.

At the start, they’re not achieving their full potential.

They want more.

Our product or service helps them become that better person.


🌋 Event conflicts are all about changing the status quo.

Something big has happened. Our characters have to respond.

Event conflicts begin when the status quo is threatened.

They end when the character is returned to the status quo or to a better version of it.

Event conflicts are great for discussing your company’s role in the narrative.

They’re perfect for answering “why now?” What changed in your customer’s world to make your product relevant today?

In 2023, there are plenty of “events” to use in your stories.

The pandemic, the war in Ukraine, and the explosion of AI.

Each one of these threatens the status quo and provides new conflicts your customers have to navigate.


Understanding the MICE quotient can help you craft compelling stories & captivate your customers.

Use the 4 conflicts:

1. 🗺️ Milieu
2. ❓ Inquiry
3. 🦋 Character
4. 🌋 Event.

And watch your vision spread to customers, investors, and the world.


Early-stage founder?

Recession, Who Cares? – Why Founders Should Embrace the Recession, Not Run From It

Recession, Who Cares? – Why Founders Should Embrace the Recession, Not Run From It 1024 667 James Knight

Recession. A big scary word.

When the economy shrinks, there’s less for everyone. Less money in the money stream. Fewer jobs on the job tree.

When markets slow, growth slows.

But not for startups.


Recessions are macro-level events.

They affect the market as a whole.

If you’re at market scale (think Google or Amazon), then they affect you greatly.

Google (~30% of online ad revenue) and Amazon (~40% of online retail spend) are the market.

They’re macro-level companies.

But startups aren’t macro-level.


Macro-level changes aren’t evenly distributed.

Even if the system as a whole is trending one way, parts of the system can trend the other.

Global temperatures have risen ~1C since 1900 [1].

But 2022’s winter storms brought record-lows in many American cities [2].

These aren’t contradictory.

Recessions are no different.

Just like the climate, it’s possible for some areas to cool while others experience record heat.

Startups just need to go where it’s hot.


Macro changes cause migrations.

Rising temperatures in Burgundy threaten the world’s greatest Pinot Noirs.

But that same warmth in England is helping them produce quality sparkling wine for the first time in history.

Startups should be planting in England, not farming in Burgundy.


What does this mean for founders?

For the first time in a decade, Google, Amazon, and Microsoft have hit the PAUSE button on their growth.

They’re not throwing piles of money at every tech hire in the country. They’re not investing in new, risky industries.

They’ve shut themselves in the cave, hoping to wait out the winter.

The biggest predators in the woods are sleeping.


As a founder, recessions shouldn’t scare you.

Change runs through your veins.

Fuck the Macro. Embrace the Micro.


Early-stage founder?