Oh, the startup life! Marching bravely into the unknown, finding your way as you go. And just when you think you’ve got it all figured out, you realize how much you still don’t know. When two months ahead is considered long term, is there a point in planning at all?

When I work with startups, I typically start with the product strategy. We work on it for a while, and this creates clarity and alignment regarding what needs to be done. In most cases, the product strategy process results in meaningful insights regarding the product and priorities, so the impact on the features developed is immediately felt. We make progress, step by step, toward the major initial achievements (usually the first few milestones of the new or refined direction we unveiled during the product strategy work). We always have the strategy in mind, so the decisions are calculated and well thought through. And then, at some point, this doesn’t seem to be enough.

It typically goes like this:

CPO: “today I want us to work on the roadmap”

Me: “awesome, how far into the future are we talking about?”

CPO: “full quarter ahead”

Me: “well, that’s not a roadmap. That’s just organizing your backlog. Why do you want to do it?”

CPO: “because there are too many things happening and people want to know what to do”

Me: “got it. Why don’t we tie it all together into a real roadmap that looks more than a quarter ahead?”

CPO (struggling): “honestly I can’t think that far into the future. I just need to sort the immediate work plan out”

Since I always work with reality and not against it, we usually end up organizing the work plan for the upcoming quarter, so that the CPO can get it off their heads and get everyone aligned accordingly. But at some point, this isn’t enough either. The problem is that it’s not clear to the CPO why, exactly. I mean, we have a strategy, we make progress accordingly, and we understand why we are making each and every step along the way, so what’s missing?

Y., One of the CPOs I work with recently wanted to work on the roadmap – again. When I asked why as per the above dialogue, he said that I keep telling him that what he is doing is not a roadmap, so he wanted to know what this roadmap that I’m talking about really is. I felt he was ready 🙂

Still, at some point, Y. said he is not sure why he needed a roadmap. At the end of the process, I asked him if he sees the benefits of having one. He gave me a few, and not necessarily the ones you would think about. So here they are so that you can enjoy them too.

From Intuition to Logic

I’m a big believer in Intuition. Don’t get me wrong, I don’t think we should trust it blindly, but it definitely helps us find the right direction. One of my favorite paths with my consulting customers and CPO Bootcamp participants is to help them translate their intuition into logical thinking. 

The reason I’m a big believer in intuition is that I’ve seen it develop over time in my own experience. I felt it most significantly when I joined a cybersecurity company with no knowledge of security. Initially, I couldn’t trust anything I thought without validating first, but over time I ended up getting my gut feelings validated time and again. 

In my work with Y., we created a solid product strategy to guide us, and Y. brought his well-developed intuition as someone who lives and breathes their domain for many years into everyday planning. When planning the quarter ahead, Y. knew what needed to be done. His intuition compiled the strategy together with what he saw in the field, thus bridging the gap between the strategy and the work plan – the exact same gap that a roadmap is here to cover. 

Once we completed the roadmap process, although the outcome wasn’t very different from what Y. had initially envisioned, he was able to explain to himself why his intuition was right. This is a major leap forward in terms of any CPO’s ability to lead with confidence, primarily because of the reason listed below. 

They Need to Understand It Too

We all know that “trust me, I’m a product manager” doesn’t work. We all work hard to provide data around the directions we want to lead in and enroll others in following our lead.

Data is great, but for facts to matter, they need context. Once you have a clear understanding of how you are going to win the year ahead and are able to explain it in a way that makes sense, start to finish, others can get it too. It is only then that the data you add to prove your claims contributes significantly to the discussion. 

In most cases, once you are able to explain the way you think to others, they simply get it. Y. said that he got little to no questions from the audience listening to his roadmap presentations. Things made sense.

It was especially true with the people who are doing the work. Following your lead is much easier when they trust you that you are thinking things through. When you explain why we are doing what we are doing, you help them trust you.

They Are Not in the Details

Another thing to remember is that as a product leader you live and breath your product and more specifically the gaps you want to close in the foreseeable future. You can talk about it in detail even if they wake you up in the middle of the night. But the rest of the company – both management and the teams doing the work – don’t see it as well as you do.

Part of it is because they don’t have your point of view: senior management typically sees a very very big picture without getting into the details, especially not the details outside of their own direct responsibility. And the teams doing the work are well familiar with the details but are often lacking the bigger picture. Even if they get the big picture at some level, it is not trivial for them to bridge the gap between that and the everyday work that they are doing. They don’t necessarily have your intuition to help them connect the dots.

This is exactly what the roadmap is all about: it’s a story that explains how you are going to meet your goals and maps the work itself into a larger context. This context needs explaining. Without it, people might do the right thing but wouldn’t understand why that’s the case. In today’s recruiting battles, not feeling that leadership provides a clear direction is a good enough reason for people to leave (honestly, I left a company for the exact same reason many years ago).

Your roadmap is not just a way to let people know what they need to do. It is a tool for company-wide alignment, for better outcomes, and eventually for employee retention. I promised that these wouldn’t be the benefits that you immediately thought of 🙂