Stop Obsessing Over the Release Calendar

I've been working with a client recently that views Product Management as role of execution. 100% of the time. No customer research, no strategy, no view of customer data.

People hand them tickets. They go make sure the work gets done.

The worst case of "Pretend Product" I've encountered yet.

There are many factors contributing to this mess. And so many changes that need to be made to start cleaning it up.

The biggest problem however, is both the easiest and the hardest to solve.

It's the way the Product team thinks (or has been conditioned to think).

It's all in release windows. EVERYTHING they do is centered around a JIRA ticket and a delivery date. It's not a stretch to say nothing else really matters. Little thought is given to anything else.

The senior leaders want things for reasons that are unknown. They ask for them. Product handles paperwork to get other groups involved. Everything from there is all about sprint and release calendars. Their "roadmap" is a spreadsheet of "Project" names with release dates attached to them.

This behavior (and a reluctance to stray from it and grow into real Product Managers) is difficult to change. But it MUST. They do themselves no favors by holding on to this behavior.

Because when product people obsess over delivery dates, they stop being strategic. They start playing project manager instead of product leader. They start shoving features into timelines that don’t match customer needs, or make any sense. Nobody trusts you to make good decisions.

Product Managers add value to execution by bringing clarity and alignment. Filling out paperwork and managing JIRA tickets is a complete waste of time and brain power.

As I'm preparing materials for a discussion on what needs to change and why, let me share the highlights with you.

Takeaway 1: Deadlines are not your deliverable

Let’s say it clearly. Your job is not to guarantee that a feature goes out on May 15th.

Your job is to deeply understand the customer problems worth solving, shaping the right solutions with your partners, and helping the team stay focused on the outcome.

You are not QA. You are not engineering management. You are not a Scrum Master. You don’t need to track burndown charts like your life depends on it.

What you need to do is stay close enough to the delivery that you can support good decision-making and keep stakeholders aligned. But you don’t own the timeline. You partner with people who do.

If you're regularly chasing delivery dates like a project manager, you're signaling one of two things: either you're unclear on your actual job, or your delivery teams are incapable of planning and communicating.

Neither is a good look.

Takeaway 2: Your customers don’t care about your calendar

You know what your customers care about? Their problem being fixed. Their pain point going away. Their workflow getting easier. Their task getting faster. That’s it.

Nobody outside your company cares that your team is targeting “Q3” for a release. They don’t care about what’s coming in version 2.6.3. They care about results.

You could hit every date on your roadmap and still fail to move the needle for customers. Because hitting a date doesn’t guarantee that you solved anything.

Too many product people spend their time managing a calendar that means nothing to the outside world. You want to make an impact? Spend more time figuring out if you’re even solving the right problem. Spend less time updating the release plan.

Takeaway 3: Most delivery estimates are guesses. Stop treating them like commitments.

There’s a massive difference between a forecast and a promise. You might think you’re offering a rough estimate. But the moment you say it out loud, your stakeholders treat it like it’s carved into stone.

Then what happens? Your engineers hit an unexpected dependency. Your designer goes on leave. The work turns out to be bigger than expected. And now you’re behind.

You scramble. You try to catch up. You make compromises on quality. You drop scope. You play calendar Tetris just to make the fake deadline feel real.

And for what? So you can say you launched “on time”? On a date you made up based on a high level swag in a conference room 8 months ago?

What if you didn’t do that? What if you said: “Here’s the problem we’re solving. Here’s why it matters. Here’s what we’re building. And our delivery team will tell us when it’s ready.”

You’re not ducking accountability. You’re pointing it in the right direction.

Takeaway 4: The real leverage comes from clarity, not control

You are not valuable because you hit deadlines. You are valuable because you help people focus on what matters.

That means spending more time making sure the team understands the customer’s need. That means defining the problem clearly. That means working with design and engineering to make smart tradeoffs. That means talking to sales, support, legal, operations, and everyone else impacted by the work so that nothing important gets missed

The real value of a good product person is that they help the system move with less friction. Not because they control the system. But because they remove ambiguity from it.

When people know what they’re building and why, they tend to move fast. When they don’t, they flail. Don’t manage a gantt chart. Manage the clarity of the mission.

The best metaphor I've heard is from the CEO of a company I once worked with. He told me to visualize a machine filled with gears and belts running. All serve their own individual purpose. But by moving in the right direction, their combined efforts make the machine run.

Now, remove the central gear. All of the other gears keep moving, but they are spinning in different directions now. Still appearing to serve their individual purpose, but no longer aligned and working together. The machine stops working, even though most of the internal components are working harder than ever.

This is what happens to many companies with weak Product teams. There is no strategy, no clarity, no alignment. People are just working on what seems like random things, with no idea why. Everyone is just spinning off in different directions. Busy, but not really achieving anything.

Takeaway 5: Let your delivery team own the “when”

You want to be a better partner to your engineering and design leads? Stop giving them deadlines they didn’t ask for.

Instead, show up with a well-shaped problem. Share the user pain. Talk about constraints. Align on what success looks like. Then ask: “What would it take to deliver this well?”

When you stop treating delivery like a race against the clock, your delivery partners stop treating you like a timeline tyrant. And guess what? They actually want to collaborate.

Too many product people think they’re doing their job by pushing teams to “go faster.” But you’re not a coach. You’re a partner. You’re there to make the work better, not just faster.

The more you focus on delivery speed, the less space you leave for teams to do good work. Give them the autonomy to manage their process. They’ll respect you more for it.

In Conclusion

You’re not building software for a calendar. You’re building it for a customer. That customer doesn’t care about your release plan. They care about whether the thing you build solves something real.

So stop pretending the deadline is your North Star. It’s not. The real win is when your work actually matters. Everything else is noise.

Thanks for reading. See you next week.