My new COO has started in early January and I am delighted to have her. The search, though, wasn’t trivial. After reviewing over 50 candidates, 25 phone interviews, and 15 full interviews, I eventually had to choose between a few final contenders. 

The finalists were very different from one another, and I realized that it came down to selecting between two alternatives: I had to choose between someone who is an expert in some areas, but with less ability to expand to other areas, and someone with less expertise in specific areas but greater learning potential for these and all other areas that mattered. Of course, it would have been ideal to find someone who had had both extensive experience and amazing learning abilities, but there’s a reason unicorns are so rare.

Throughout the search I had to ask myself two significant questions:

1.     What’s important to my company?

2.     What are the trade-offs I am willing to make?

These are the exact questions you need to ask when creating your roadmap.

Understand Your Core Values

The product roadmap in a product company (as opposed to a services company, for example) sets the strategic direction of everything going on. In startups, it is actually the company roadmap. As such, it cannot be limited to include only the product-related parts like features and product KPIs. As a product leader who is creating this roadmap, you need to treat it as a compass and plan not only for your team and the technology team but rather as the direction that the entire company needs to go in. Naturally, this means that it needs to address aspects that are not necessarily within your direct control as the manager of the product department. For example, you gain nothing from having a new product if the company can’t sell it to the market, so your roadmap must address also the sellability of the product.

I recently started working with a new consulting customer who offers digital courses over their unique platform, and one of the questions that they asked in the first session was whether or not the content was part of the platform. I told them that even though their head of product didn’t manage the content team, the content should be considered part of the product since it is an essential part of the value they provide to the customers. So, having a great platform but poor content won’t really help them. Even having great content that isn’t relevant to their target audience won’t do the trick. In this example, the roadmap had to address the content as well – not necessarily in planning it but in making sure that it is fit for whatever value the company is looking to bring to their customers.

Another way to uncover what’s important for the product and the company as a whole is to ask yourself – if you fail, what would you have done wrong? For instance, you may fail if you don’t move fast enough – so moving quickly is essential for your company. Moving fast could mean developing a product that brings value to your customers at any given time, a low-touch product, or supporting multiple verticals simultaneously. Once you understand what moving fast means in your case, you have uncovered one of the core values for your roadmap. 

As I mentioned in my previous article, your roadmap should not be a list of features or capabilities, but rather a list of qualities and achievements. They are easy to confuse and most product leaders find it much easier to create a roadmap based on features, so I’ll share a few examples to explain the difference. Let’s take the Headspace app (which teaches meditation and mindfulness)  as an example; As an app that is aimed at changing people’s behavior on their day-to-day conduct, it probably needs to be proactive and engaging – an actual coach quality. This quality translates to many different features and serves as a guideline for many nuances in the product as well as marketing materials.

Another example is a security product I worked on that had to be as plug-and-play as possible – a non-trivial task for an on-premise product that needed access to the many assets it needed to monitor. Being plug-and-play, or aiming there, was our added value and a differentiator compared to other security products. In practice it translated to many features around the onboarding process – some user-related and others very technical that aimed at making the whole process as seamless as possible.

Engage in a Multi-Dimensional World

Once you define what’s important to you (as a company, not just for the product per se), you have a new language to speak in. The core values or principles of the product define the world in which you need to live and win over time.

To help everyone understand what you are talking about and adjust to this new world and language, I recommend using a great tool called spider charts. If you haven’t seen one before, you will soon understand why they are called that way.

Spider charts (or radar charts) are a tool that helps visualize progress over multiple dimensions at once. A spider chart shows data in a two-dimensional chart, where three or more measurable variables are plotted on axes, starting from the same central point. The farther you are from the center at each axis, the more advanced you are in that dimension.

When you create your dimensions as the core values or principles, mark the value that represents your current state in each. The shape that you get by connecting all the dots easily tells you the full story of where you are. For example in my COO hiring decision, I realized that I’m actually considering two different spider charts and that’s the important decision to make, prior to considering any specific candidates.

Remember that the world is not black or white, and there are many places on the sequence of each dimension, each representing a different level of progress in that dimension. You have many options to choose from between none to full power in each dimension, so make sure you select the level that accurately represents your current state in each.

Once you have done that, the next step is to decide where you want to be at the end of the process. Remember that the end goal is not necessarily to achieve 100% on every dimension. In some cases, it may not be realistic or necessary to get there within the specific roadmap’s time frame. In other cases, you might never want to get to 100% in certain dimensions, and striving to get there could even be a mistake. For example, if one of your values is a secure platform, it doesn’t mean that you need to do everything you possibly can to add security to the product. At some point, the added value would become negligible compared to the effort you would need to invest in building it. So perhaps your end goal in that dimension would be around 60-80% – the actual number might be impacted by regulation requirements and general best practices.

Define the Path Between the Start to Finish

Now that you have your starting point and your end goal plotted on the chart, you can start to define the desired path between them, AKA your roadmap. Note that there is an infinite number of paths: you can decide to make progress in a certain dimension and bring it to 80% before you start moving in any other dimension, you can make small changes in all dimensions every step of the way, and any other mixed progress the way you see fit.

Once you do that, you can plot your roadmap as a sequence of spider charts that shows the progress over time. In fact, you can plot a number of such sequences to explore with the team which roadmap is better. This helps you answer one of the most important questions when you build your roadmap: why, out of all possible roadmaps, this is the right one?

In other words, now that you know what is important to your company (the core values and principles), and you know your start and finish points, you should start addressing the second question I mentioned earlier: which trade-offs you are willing to make, and in some cases which trade-offs reality forces you to make. It could be that to truly make your product seamless in the customer environment, would take you too long and you can’t afford to focus only on that while not making progress in other areas. In other cases, gaining little progress on all dimensions at once wouldn’t result in a significant added value compared to moving each dimension on its own a significant amount. 

To see these trade-offs clearly, you can name each phase and chart in each series. The name should reflect the outcome or result that you are expecting to have at this point (e.g. enterprise-ready product, happy and retained design partners, new platform launch, etc.). Naming these milestones will help you to crystalize the value and advantages of each, and distinguish them from one another. By doing so you are adding more words to the newly created language of values and principles and can foster the proper discussion around them.

These discussions are critical, and spider charts are a powerful tool for making this discussion more coherent and visual. Another quality of spider charts is that you cannot get into the details very easily. By using them as your primary storyline for your possible roadmaps, you are making sure that the discussion will remain at the proper level – the strategic level that matters.