Sounds like basic stuff, but in my experience, its one of the most common reasons Product Engineering orgs can feel chaotic, and/or not making tangible progress on their goals. Here I break down why this happens, what we can do about it, and offer a couple of resources to help....
The 'Disconnection' Problem
Usually, OKRs live in one place - a PowerPoint, in confluence, notion. Roadmaps often live somewhere else entirely - aha!, Jira, Azure. Commonly, nobody explicitly traces the line between them, resulting in busy teams that are not actually moving the needle on the actual things that matter.
A common sentence I hear is "I have all these items on my roadmap, how do I tie these into the new company goals?" - Sound familiar? I've never worked in a business where this is not true to some extent.
Why it happens
OKRs are often written top down by a management group (Company > Product > Teams). Roadmaps are built bottom up (Backlog > Quarters). All of it has different owners, in different tools, and operated on different cadences - add to that, that often the cascade itself is often incomplete - someone writes the company OKRs but the product and team level translations don't get formally written.
Often times, although teams have a general idea of the objective they are trying to meet, the Key Results which measure & prove it are not explicitly called out or remain undefined.
In a big rush, people make assumptions about what things will move the dial, and that thinking gets baked into the roadmap. Then, in no time at all, we're reverting to trying to shoe horn already in flight features to goals, retrospectively.
The Fix - doing it properly
Before anyone touches a roadmap, we need to apply critical thought leadership at all the levels and take a moment to do the full cascade properly. For each of the company OKRs, what specifically must the product deliver to deliver those? Of what, what must each squad own? - Each Key Result at team level should map directly to the key result at product level, which in turn maps directly to the relevant key result at company level.
In my experience, most orgs skip straight into solutionising the roadmap before locking in the OKR cascade at this point, directly causing the disconnect. In my opinion, time spent getting the cascade right and 'locked-in' helps ensure the resulting roadmaps stay tightly tuned towards the metrics that matter.
For more detail on how to think about this, a practitioners guide to creating OKRs, please see this resource on the subject.
OKR Framework - Setting Goals that Matter →Also, this real world example might help you visualise it.
PAYG OKR Cascade - Live Example →OKRs Into Roadmap - Make it mechanical
If we spend time considering, aligning and completing the full OKR cascade properly, the roadmap translation becomes almost mechanical. The hard work should already been done, we're then just turning that into a set of tasks for teams over time:
Each Product OKR then just becomes a roadmap swim-lane or theme. Team key results become specific initiatives in each quarter.
Remember - Quarterly distribution & reflection is key to achieving the goals at the end of the year, and another area which is a common mistake for teams and orgs. High performing teams review at regular intervals to see how we are doing and adjust accordingly.
In fact, it occurred to me that creating the roadmap from solid OKRs should be so mechanical, we should be able to use an LLM to automatically create a roadmap from our OKR cascade sheet.
So, I built this lightweight tool to test this idea - a Strategic Roadmapping tool which takes in your OKR cascade (another lightweight tool available) and generates a customised and editable strategic roadmap from it.
Strategic Roadmap Tool →Key point being - encourage product folk to spend time thinking about their OKR cascade more than the mechanics of a roadmap - that's the straightforward part and can be relatively automated. Don't spend hours on painstakingly building nice roadmaps, spend your time on the proper thinking behind it.
Closing
Following this simple and straightforward advice around OKR preparation can turn "how do my items relate to the top level goals" to "We're literally moving the needle on the specific KRs which matter most".
Feel free to use both these free resources to help guide your product thinking through the OKR > Roadmap flow.
Free Resources
How does your team bridge OKRs and roadmap planning? I'd love to hear what works for you.