The Roadmap to Mediocrity

If you hold any sort of leadership role in high tech right now, you’re probably spending quite some time handling the roadmap for the upcoming year, or at least the next quarter. As someone who often preaches the importance of taking the time for long-term thinking, I have grown to dislike how most of these roadmap-compiling efforts are performed. Yes, any roadmap is likely better than no roadmap at all. However, if you’re anything like the preponderance of companies I see, your roadmap drives your engineering team to mediocrity, timidity, and complacency.

Here are the most common pitfalls I see my clients getting into during their planning and roadmapping pomp and circumstance.

Participation-Award Plans

First and foremost, the easiest way to assure short-term “success” and long-term degeneration of any good team is creating roadmaps with no risk. A plan that you have 100% certainty will be achieved is too complacent for virtually any business. If your team doesn’t feel at least somewhat uncomfortable with the objectives they’re committing to, you’re playing in the little leagues.

Now, you might be thinking, “easy roadmaps? Has this guy ever even talked to a startup?” That’s right; most executive teams don’t create roadmaps that are plainly “easy” to do. However, too often, the risk merely consists of a lot of work. Working harder is a cheat—it will work for a while. However, your roadmap should be a bit intimidating not because it requires a lot of hard work, but on the merit of requiring smart work. If you can see everything happening if the team burns the midnight oil a few times, you’re replacing ingenuity with sweat. For me, that’s not what high tech is about. Roadmaps should invigorate the team and keep them on the balls of their feet.


CEO/VP Product: We’ll take those three features and one grande mobile app.

VP Engineering: Would you like some fries with that?

I keep harping about tech executives being too focused on the “tech” part and not understanding what “executive” means. You have a great responsibility, and with it should come great power. If you’re located too low in the decision stream, you’re handed over orders without having the ability to shape the work the company’s doing.

If your involvement in forming the roadmap boils down to merely playing the estimation game to decide what makes the cut, you’re selling yourself short. You, as a tech executive, should actively move upstream. Being placed there will allow you to get greater insight and more context. That, in turn, will enable you to help the company form strategies that make better use of your team. It also has the added benefit of making the team understand the reasoning behind objectives, unlocking feedback about ROI and trade-offs. In general, this makes you and your organization less of a JIRA machine.

Innovation Oblivion

We rarely end up having a lot of buffer space in roadmaps. Nevertheless, you should account for the extra time needed for experimentation, tinkering, innovations, and the failures that come with them. Otherwise, you are letting your team know that rote execution is more critical than putting their brains to use.

I’ve written more about managing non-feature work and discussed failing spectacularly on the Tech Exec Podcast (top 10 podcasts for CTOs for over a year now, BTW).

Prescribing Solutions

One last common pitfall is a continuation of the order-taking mentality. Where you specifically as the executive might be more involved, the roadmap and tasks given to your team can be too prescriptive. Rather than stating a goal or an objective and letting an empowered and autonomous team decide on the right way to tackle it, you tell them precisely what to do.

Like it or not, this is a form of micro-management that takes away your best people’s agency and creates a product and a team that is only as good as your solutions. Instead, consider empowering your team to make more decisions and create a solution that’s the sum of their best thinking.

Looking back at whatever roadmap efforts you’ve already done, how many of these mistakes can you spot? Pave a better road.