Slow Teams and Failing Features: Tackling Roadmap Challenges

Aakash Gupta
2 min readJul 11, 2024

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Roadmaps work. If you can estimate impact and work well.

Roadmaps are often criticized as “more dream than plan.”

The issue usually is one of two types:

  1. Type 1 — Slow Teams
  2. Type 2 — Failing Features

Let’s break down each:

Type 1 — Slow Teams

↳ “We won’t be able to achieve any of our plans”

↳ “Most of our items will take longer than expected”

Type 2 — Failing Features

↳ “The majority of our A/B tests will fail”

↳ “We’re won’t get close to the impact we assumed”

Both of these types of Roadmap Risks can’t be eliminated.

But they can be reduced.

Here’s how:

Type 1 — Slow Teams

  • Invest in reducing your tech debt
  • Get engineering to care about product release velocity
  • Improve review processes to reduce all complexity in the code base

Type 2 — Failing Features

  • Become better at impact sizing
  • Invest in rigorous user research invalidation of designs
  • Empower teams to react to new learnings on the fly without approval

“But impact sizing accurately is impossible”

→ Perhaps for some products.

→ But not for more mature products.

→ I wrote more about impact sizing here.

“But roadmaps are going to be inaccurate.”

→ Roadmaps shouldn’t be commitments.

→ Instead, they should be communication tools.

→ I wrote about advanced roadmaps and how to develop them here.

The biggest driver of roadmap use is leadership and cross-functional communication.

It shows that you, as a PM and product team, have a POV. That you have done your homework.

I’d love to hear from you.

Do you not use a roadmap?

I’d love to hear from you in the comments.

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Aakash Gupta

Helping PMs, product leaders, and product aspirants succeed