Strategic Roadmapping

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