Blood, Sweat and Roadmaps
The 7 Laws of Roadmapping
"Because I don't trust any of you", the CTO blurted out.
The room fell silent. All eyes were darting around the room, looking at each other in disbelief. I was sitting in a meeting room with all ten Product Managers working at a local department of a multi-billion-dollar company.
Nobody knew how to respond. Did he really just utter those damning words?
Every second of silence that passed, made everyone in the room feel even more uncomfortable.
I remember being in shock and thinking: “Even if you felt like you couldn’t trust anyone, what is the added value of saying that to their face? How would that help with anything other than them distrusting you as well?”
The surprising answer of the CTO was a response to a question I had asked: "Why don't you let us Product Managers together decide on how we do roadmapping?”
I had asked this question because our roadmapping approach was infuriatingly useless and time-consuming. It was an obstacle that stood in the way of our teams collaborating effectively.
Every quarter we would gather together to discuss the roadmaps and shuffle work worth tens of millions in terms of business cases, hoping to make a big impact.
Except that big impact rarely happened. In fact, the opposite happened.
Our roadmap was filled with futile initiatives based on paper victory business cases. Creating the roadmap was a huge waste of time and doing what was on the roadmap was an even bigger waste of time. Plus we were working on far too many things at once, which meant we were all suffering from a triple whammy of waste.
How do companies end up with a roadmap full of waste and useless initiatives that will bring little value?
The 7 Laws of Roadmapping can perfectly explain why this happens, let’s kick it off with the first law.
#1. Roadmaps Mirror the Level of Organizational Incompetence
Your roadmap is like an indicator species that reveals all the organizational dysfunctions in your organization. The roadmap is where business and tech meet, where your vision and strategy collide with your execution and teams. The roadmap is where departments and business units compete with your teams and other organizational priorities.
All the conflicts, disagreements, lack of strategic decision making, and operational obstacles are visible on the bloody battleground of your roadmap.
That’s why I like to speak of blood, sweat and roadmaps. Coming up with a good roadmap is incredibly difficult because it’s a bloody battleground where all the competing interests and differences of opinion become visible.
We could visualize some of these competing interests as follows, but there are many more happening simultaneously that can become visible on your roadmap:
The fact that roadmaps often seem to become a bloody battleground, a.k.a. blood, sweat and roadmaps, I’ve coined as the the Penguin Principle in the past:
“Your roadmap reflects your organizational inadequacy.”
Phrased in a more friendly way: the roadmap exposes your organizational flaws.
Here are some common organizational flaws that can easily be detected by examining your roadmap:
Poor leadership. A lack of Vision or Strategy is immediately visible on the roadmap.
If nothing on the roadmap relates to your Vision or Strategy, you’ve got a leadership problem. Suppose everything on your roadmap relates to your Vision or Strategy, then you’ll likely have a leadership problem too. When your Vision or Strategy are weak, because they are phrased in such a generic and bland way, then anything can be related to it.
Institutionalized Competing Interests (ICI). Does every team have their own priority, or do they work based on a shared priority? Does every team have their own roadmap, or do teams have a shared roadmap across teams? Is the priority across all teams clear, or do teams have to figure it out and fight it out to resolve conflicts?
Coordination hell. How many different teams do you need to put a single roadmap item live?
High Work In Progress (WIP). How many different items are teams expected to work on simultaneously?
Lack of experimentation and discovery. Ask for each roadmap item, how it ended up there and what will happen after it’s picked up on the roadmap. You will easily figure out whether they are doing discovery or running experiments.
You don’t need to do an Agile maturity scan to detect any of these problems. All the evidence is right there in front of your eyes. All you need is to ask if you can see their roadmaps, and ask a few simple follow-up questions. Within a few hours, you can easily discover most of the organizational dysfunctions.
I want to stress, there are many more problems you can detect by simply examining the roadmap, but these are just some of the easy and most obvious ones.
#2. If You Don’t Trust Your Teams, You Can’t Trust Your Roadmap
When you distrust your teams, they will hide things and provide watermelon roadmap updates where everything looks green until you’ll unexpectedly begin bleeding bloody red from all the problems your teams are facing. This usually happens suddenly when you’re close to the end of the project.
Another problem with distrusting your teams, is that you will demand them to provide more certainty, control and confidence. But when you do complex work, the whole point is you will perpetually face uncertainty, must adapt and deal with risk.
When you don’t trust your teams, you will request a level of detail that will slow things down, make them perform worse, and actually result in even more distrust. When you distrust your teams, they’ll become preoccupied with providing the illusion of control over making the best decisions at the right moment.
#3. No Roadmap Survives Contact With Reality
As you do the work, you will discover the work you must do. Every step you take should help shape the way. The purpose of your roadmap is to keep you anchored in reality, not to keep you anchored in the roadmap.
As the saying goes: the map is not the terrain, and your boots must remain on the ground so you navigate the terrain and don’t get lost based on flawed assumptions and guesses disconnected from reality.
#4. Roadmaps Sculpted to Impress Will Disappoint
Certainty, control, confidence and providing details looks impressive on your roadmap, like you absolutely know what you’re doing. But all you’re doing is making your roadmaps disconnected from reality and clouding them with the fog of speculation.
The more you try to prevent sucking at predicting, the more you will guarantee to suck at adapting. The bigger your roadmapping circus, the worse your results will be. Your teams will be busy chasing paper victories instead of trying to make the right decision at the right moment.
#5. Bloated Roadmaps Reveal Cowardice in Vision and Strategy
The fear of making the wrong choice is one of the most powerful forces in an organization. It’s sneaky, hiding in plain sight, quietly influencing decisions without people realizing it.
We're so scared of making the wrong decision, that we don't choose.
And we feel great for not choosing, because we’re choosing to do it all. YEEHAWW! We rally the troops and tell them: “Let’s go team! We’ve got this!”. We foolishly choose to keep all our options open and waste our effort to inspire everyone to put their shoulders under it.
But here’s the catch: those options aren’t harmless. They’re silently and invisibly cannibalizing each other.
The cannibalization is immediately noticeable for the people that do the work. They’re pulled in a thousand directions and spread too thin. The leadership team doesn’t experience the self-inflicted cannibalization and simply thinks: why are they not working harder to make it work?
Our leaders believe we're trying to do all of it, while in fact we will only be doing some of it. The problem is that we’ve lost control over what some of it we will be completing.
When those competing interests begin cannibalizing each other, you lose control. We should not fear making the wrong choice, we should fear not making enough choices.
Do we want to be constrained by doing too many different and competing things at the same time? Or do we want to constrain ourselves by making tough decisions and applying rigorous focus?
What makes it incredibly hard is that tough decisions often make us instantly feel bad. Choosing to not do something, means we immediately lose something. We feel that sting immediately. Keeping all our options option makes us feel great. We stay in our happy illusion that nothing is lost, until reality kicks in.
When ultimately the rubble of failed choices comes crashing down on us, we usually find something else to blame, instead of our original failure to make more choices.
The fear or making the wrong choice is extremely human, but instead of running away and letting it catch up to us, we should lean in. Because not making enough tough decisions is THE wrong choice.
The only question we should ask ourselves: do we want to control the pain of losing something or do we want to leave it up to chance?
#6. Clearly Incomplete Beats Unclearly Exhaustive
Not everything you do should be on your roadmap, I repeat, your roadmap should never contain all the work your teams are doing. If your roadmap becomes overwhelming and too difficult to understand, then you’re completely missing the point.
Your roadmap can only support collaboration, alignment and delivering better results when it provides clarity. The moment it becomes overwhelming, confusing and bloated with noise, then you’re totally missing the point of a roadmap.
Unclearly exhaustive means you’re telling too much with your roadmap and they will remember less. It’s also the moment you will lose control over what they will remember. Clearly incomplete means you tell them less, they will remember more, and you will be in control over what they remember.
With roadmaps, less is more, as you don’t want to bury the signal with noise.
#7. Better Coordination Does Not Fix Poor Collaboration
If your roadmap resembles spaghetti, with numerous dependencies between teams, you will have a spaghetti collaboration.
Unless you’re running a pasta factory: that’s not good.
If you have collaboration problems, don’t try to fix them through better coordination. Focus on resolving your collaboration problems and then you will also reduce your coordination issues.
Complex work means you can’t accurately plan and predict. Even with the right expertise, you will encounter many surprises. No amount of up-front coordination will prevent these surprises, and that’s why it’s much more important to improve collaboration, as you can’t coordinate what you don’t know yet.
Maarten’s 7 Laws of Roadmapping
If you remember one law of the 7 Laws of Roadmapping, then please remember the first one: your roadmap exposes your organizational flaws. Your roadmap reflects the level of organizational inadequacy.
By looking at our roadmap, we can easily discover many of the problems that are present in our organization and the challenges our teams must deal with.
Most roadmap challenges, have nothing to do with the roadmapping expertise that’s present in your organization, but all the problems that become visible in the shape of blood, sweat and roadmaps. Tthe mindset, way of thinking, process, the way your organization is structured, and other problems that prevent your roadmap from working well. The 2nd till the 7th laws help to paint a picture of what a good roadmap should be like.
Your roadmap will reveal your problems, but a better roadmap won’t fix your problems.
You can only fix your problems by fixing your problems, and 99.9% of the time the solution isn’t making better roadmaps or having better tooling, but to finally have the guts to face your organizational demons and be prepared to take a shot at slaying them.
The roadmap reflects the level of organizational incompetence and the only way of removing that bottleneck is by actually addressing your organizational problems, not by using your roadmapping process to sweep all your existing dysfunctions under the rug. As that’s what most companies do.
Do you want blood, sweat and roadmaps? Or do you want teams that trust each other, collaborate, and adapt as they discover and learn what’s necessary to deliver products that serve customers in a way that also works for the business?
Use the 7 Laws of Roadmapping as a guide to help diagnose and resolve problems. And more importantly, as with any law, the most important thing is that it actually works, not that you’re perfectly following the law.
Acknowledgements
Special thanks to
, Jasenko Ramljak, and Tanner Wortham for their valuable feedback and suggestions!
Great reading! Always good to remember that trust alone will not fix everything, but is the pillar to start fixing it at least.
I think about Dave Snowden’s Cynefin framework which suggests that in complex systems, even with trust and collaboration, outcomes are emergent and not always predictable.
So while fixing culture is crucial, leaders also need to accept a level of humility that even the best planning and trust can only guide, not guarantee, the right outcomes.
I really appreciate the brutal honesty here, especially the idea that better coordination cannot fix poor collaboration.
I agree, these problems exist. Why do we still have them after decades of roadmapping and decades of Agile? I believe a strong reason is that there is no shared purpose of the roadmap between dev teams, management, sales, etc. They all use roadmaps for different purposes.