A Product Roadmap that doesnt suck the life out of you

Shifting rectangles right on a digital gantt chart is f*king stupid. There's only 3 things that actually matter in a product roadmap.

We’ve all been there—overwhelmed by a product roadmap that feels more like a burdenous chain than a guide. Roadmaps are meant to be strategic plans that guide your product’s development, not sets of constraints that stifle innovation and burn out your team. So, let’s talk about creating a product roadmap that doesn’t suck the life out of you and actually adds value.

The Real Purpose of a Product Roadmap

Where is the product going in the next couple months…

A product roadmap should be a high-level visual summary that maps out the vision and direction of your product over time. It aligns your team, stakeholders, and customers around your product’s goals and how you plan to achieve them. But more importantly, it should be flexible and adaptive, not rigid and draining.

It’s very important that any time a roadmap is generated to ‘report up’ to higher level stakeholders that it’s communicated that at best the next quarter is pretty much set in stone, and each quarter after get’s a lower and lower certainty profile.

If you’re planning 4 quarters in advance, by Q2 you’re not working on the most important things for the business. I can guarantee it.

The Pitfalls of Overplanning

Pointless Additions

One of the biggest mistakes is adding items to the roadmap just to fill it up. This approach is pointless. You’ll constantly be shifting items to the right, which is frustrating and demoralizing for everyone involved. It creates the illusion of progress but often leads to more chaos than clarity.

Structural Flexibility for Agility

Instead of cramming every possible feature into your roadmap, leave space. This structural flexibility encourages actual agility based on customer needs and changes in market trends. It’s more important to adapt and pivot as you learn rather than stick to a rigid plan that quickly becomes outdated.

By creating items that speak to higher order strategy, rather than individual projects you’ll find the ‘how’ becomes less important than the what. And when you’re ready to sure up the ‘how’ you’ll be doing it with the framed reference of ‘current time’ not - what you thought would be the case 6 months ago.

The Importance of Prioritization

Your roadmap should prioritize what truly matters. Focus on high-level themes and goals rather than a laundry list of features. This not only keeps the team focused but also ensures that your efforts align with business goals and customer needs.

Leave the detail for the team to figure out, trust them to read into the objectives you’ve written. And when they don’t figure it out right, look at why, and course correct.

Communicating with Leaders

Yes, roadmaps are important to show leaders that you know what to focus on. But there are other ways to achieve this. Regular updates, transparent communication, and demonstrating quick wins can often be more effective than a bloated roadmap. Leaders need to see progress, not a cluttered plan that changes every week.

And because leaders are busy, they’re less likely to notice deadlines being pushed anyway, so by not over-setting them you’ll hurt less, and waste less time explaining the changes.

Think “I’m adding this objective at this time because XYZ.” and when it changes try and speak to “XYZ is going to be ZYX now because of P”

Building a Roadmap That Adds Value

High-Level Themes

Focus on high-level themes rather than detailed features. This approach provides direction without being overly prescriptive. It allows for flexibility and adaptation as new information comes in. And it should come from a place of product vision, informed by staying close to the key drivers of the business, customers, profit, team members.

Keeping it high level, informed by key trends instead of getting lazy and guessing at everything.

Timeline with Milestones

Instead of specific dates, use broader time frames like quarters or months with key milestones. This helps track progress without creating unrealistic deadlines that stress the team out.

I hate quarters from a strict X date to Y date sense, but thinking in blocks of 3 months work is fine, you should be reasonable certain what the team is likely to be working on for the next 3 months. But not waiting for a ‘calendar quarter’ to firm up the next quarters work. This is a month on month process.

Feedback Loops

Doing the work adjusts the roadmap, every time. There’s no innovative tech development space where estimating the time things take is accurate enough to plan months and months in advance. You’re guessing at best, educated guesses are suitable, but not set in stone. Adaptability and flexibility ensures it remains relevant and adaptable to new insights, customer feedback, and market changes.

How to Create a Roadmap That Energizes Your Team

Involve the Team Early

When creating your roadmap, involve your team from the start. This fosters ownership and ensures that the roadmap reflects the collective wisdom and insights of those who will execute it. Collaboration leads to better ideas and higher motivation. If your team isn’t fighting you on the roadmap, and having suggestions they’re not close enough to the business metrics that matter, not close enough to the problems and the profits.

Keep It Flexible

Rigid Roadmaps = Stress. Software development is like a game of whose line is it anyway, if you’re shoe-horned into sprints, or estimates or guessing at exact dates and deadlines, or even worse forced by customer input to get things done by certain dates, just remember “Everything’s made up and the points don’t matter” Long term business values, goals and vision override dates/estimates every time. So keep roadmaps to high-level themes and avoid detailed feature lists that can lock you into a specific path. Allow room for iteration and adjustments based on feedback and new discoveries.

Focus on Outcomes, Not Outputs

Shift your focus from outputs (features) to outcomes (customer benefits and business value). Well explained impact to customers, and to profit will help your team understand, and work intelligently, every time. It also makes it easier to adapt the roadmap as needed while keeping the end goals in sight. The dates and estimates and pre-planned BS don’t matter if something comes up that has a bigger impact on your bottom line.

Communicate Regularly

Roadmap communication is key. Velocity and changes to projects and timelines should have some note or record of why they were changed. If you’re going to plan, and you’re going to change the plan it needs to be clear to anyone who cares why. It’ll save you answering random DMs too.

Recorded asyncronous roadmap reviews would be preferred. If someone asks for the why, point them to that, it’ll save you a lot of time.

Celebrate Milestones

Don’t forget to celebrate milestones, both big and small. Acknowledging progress boosts morale and keeps the team energized. It also reinforces the value to the business, and the value of the vision and how the roadmap applies to it. You want independent teams with agency and authority to contribute, change and produce work of value at the end of the day. So celebrate whats working as an earmark on what should be done in the future.

Avoiding Common Pitfalls

1. Over-Promising

Stop over promising. In roadmaps and sprints, get away from the idea that if the plan isn’t chocoblock with features and sprints aren’t full of tickets then people will just slack off. If the long term vision is communicated, and velocity towards the goal is championed, you won’t have that problem. An overly ambitious roadmap can lead to burnout and missed deadlines, you start missing a couple of deadlines in a row, and the dates become as meaningless as they already were, but now people know it. Be realistic about what can be achieved within the given timeframe and resources.

2. Micromanaging

A roadmap is not a micromanagement tool. Trust your team to find the best ways to achieve the high-level goals you’ve set. Micromanaging every detail can stifle creativity and reduce productivity. And trust the team to change the roadmap, based on inputs you’ve set up for them to receive, it should be entirely plausible that the roadmap was just hands down wrong about something.

3. Ignoring Feedback

Ignoring feedback from your team, stakeholders, or customers can lead to a disconnected and ineffective roadmap. Make feedback an integral part of your roadmap process and be willing to make changes based on valuable insights.

Final Thoughts

A living document that guides your product’s journey without sucking the life out of your team.

It’s possible, but not by doing more work on it, it needs less work. More guardrails less dates.

By focusing on vision, flexibility, outcomes, and regular communication, you can create a roadmap that energizes and motivates.

Remember, the goal is to keep your team aligned and inspired, not overwhelmed and exhausted. A well-crafted roadmap is your ally in building a successful product and a happy, productive team.

Hope this helps you create a more energizing and effective product roadmap!

Cheers,
Darrell