3 Steps for Managers to Discover the Right Roadmap
By Michael Hedgpeth · June 6, 2023
3 Steps for Managers to Discover the Right Roadmap

Engineering managers often struggle with and overlook the effort needed to discover the right work the team needs to do. Solid roadmaps can make or break a team’s overall effectiveness. However, managers can tend to avoid this work because it’s so disruptive. Getting this right keeps senior leadership from seeing you as a bus driver leader who takes orders and gets stuff done but isn’t strategic and impactful enough for the next level.

On the surface, it may surprise some readers that this is even an important aspect of engineering management. Some may be overwhelmed by a steady stream of demands and escalations. We know what is needed…everything! Other managers might find themselves with a product manager who makes the roadmap demands very clear and performance is measured by how well the team delivers on those goals. So why focus on this?

As a manager, you’re the one who is responsible for the outcomes of your team. You need to hire and retain great talent, deliver the work, and ensure your customers are successful. On top of that, you need to do all of this while meeting your own personal and professional goals. This is the job! Here’s how I train people to do the job (advice I follow myself):

Ask Why Until You Understand Everything

First, keep asking why until you fully understand the contents and priorities of your roadmap. Teams usually see their work as incredibly obvious, and so many managers see a full rationalization of their roadmap as someone else’s job.

An overloaded team needs radical prioritization so there is a why there for everything. They must ask which why has the largest impact. They then need to explain to the others why their request isn’t the highest impact request.

A team that is on a roadmap with a product manager might have a very strategic why. If the product manager is doing their job, they should be able to distill this strategic direction into data. For example, they might be pushing for a completely new feature they say will open up a new market segment.

Many times in my career, however, I am surprised by the extent to which some of these roadmap items can be based on something someone important said in a meeting. For example, when asking why over and over again, we find out that the request for the new feature that will open up a new market segment came from a meeting with the COO who thought the idea might be a good direction. While it may be a great idea, that’s not good enough; we need data!

So ask why, and keep asking why until you, as the owner of the team, can rationally support the prioritization of your projects and backlog. Don’t succumb to the temptation to say, “We’re doing this feature because a VP wanted it,” or, “This is simply the right thing to do.” You have to ask why that VP wants that thing and be able to justify it.

Discover the Team’s Problems

Second, understand the team’s problems and how they relate to the roadmap. I became a manager of a team that was inundated with alerts. Dozens or even hundreds of alerts per day came across their paging system or Slack channel, and when I looked at their roadmap, alert management was nowhere to be found! So I sought to deeply understand that problem and put the solution on our roadmap as the top priority. What we were doing was not sustainable.

I worked hard to include and understand all stakeholders’ priorities. The stakeholders were all remarkably supportive of making this the priority. I haven’t always been this lucky, but when I have done step one to deeply understand the basis of the team’s roadmap, I can then justify the priority of addressing the team’s problems within that context. Then we mix the two priority streams and compromise. Once we did this exercise with that team, we were able to reduce alerts by 80% in six weeks. Because we made it a priority and I knew the rest of the roadmap, I was able to justify it to stakeholders.

Supercharge with a Motivated Team

Finally, understand which items on the roadmap motivate each team member. Many managers gloss over the reality that motivation multiplies effectiveness and velocity. If a member of my team believes that a particular project will help their career, and they are motivated for career growth, it would be foolish of me to assign that project to someone else. I’ve seen three-month projects take three weeks because the person was motivated. I’ve seen two-week projects take two months because the person was not motivated.

As a manager, I prioritize aligning people’s interests with the roadmap. If I’ve done a good job understanding why the roadmap items exist and am I including the real problems the team is having in the roadmap, this is not generally a difficult thing.


These simple steps will supercharge your team’s work by making it impactful, strategic, and aligned with your team members. When this happens, magic happens. Teams who have gone through this process deliver multiples of what other teams deliver, and it makes me a stronger, more strategic leader, ready for more. I’d love to hear about your experience.