Many product management gurus recommend that product teams should avoid committing to release dates. Instead, they recommend having a sequence of problems to solve now, next, and later. 

I love the now/next/later methodology. It is a highly effective tool for communicating priorities to stakeholders. However, I still like have specific delivery dates for the items in the "now" category.

Not having specific delivery dates makes software development and product management impractical and chaotic.

Dates (aka deadlines) help to:

  • Set actionable goals: Against which we can measure progress.
  • Transparency: Leaders know when to expect the next big release
  • Resolving dependencies: Every team knows when to deliver their task so that the other teams are not blocked.
  • Create a shared sense of urgency: Everyone works with the same constraints.
  • Create accountability: So that everyone knows what they're responsible for.

With a date, everything is smooth—everyone knows what needs to be done and by when, and they plan their work accordingly. 

But, if you've worked with technology and software long enough, you know that missed deadlines are inevitable despite meticulous planning and good intentions. 

So the larger question is, what do you do when it happens?

Here's what I recommend.

Break Larger Tasks into Smaller Chunks

Attempting to estimate and deliver large tasks all at once is a setup for failure.

First, estimating large tasks is more error prone than estimating smaller ones. Second, when something goes wrong (while building large pieces of code), the team must re-work much of what they already did. The re-work leads to demotivation and more delay.

A better way to do this is to:

  1. Break the project into smaller, manageable chunks to improve estimation accuracy and progress tracking.
  2. Assign clear owners and deadlines for each chunk/subtask.
  3. Conduct frequent check-ins to identify potential roadblocks early on.

This approach allows for early detection of issues, which helps the team to make adjustments quickly to prevent the project from going off the rails. 

Divide and conquer to stay on track.

Have Multiple Smaller Milestones

Establishing multiple and clearly defined milestones throughout the project is the best thing you can do (to stay on track.)

Frequent milestones allow you to track progress, identify issues, mitigate risks, and make course corrections as needed. They also increase the likelihood of identifying problems before they become severe delays. And, they allow you to celebrate small wins along the way (to keep the team motivated and engaged.) They also provide opportunities to share progress updates broadly with stakeholders to drive alignment and increase transparency.

Milestones are the speed breakers that force you to realistically gauge success.

Review Timelines Regularly (Or After Every Milestone)

Regular progress reviews helps avoid critical blind spots.

Teams that regularly review and adjust their project timelines are more likely to meet their deadlines. Use data, past wins/fails to make informed decisions and course corrections.

Progress reviews are an extremely effective tool to stay on track, which give teams a lot of confidence and motivation to keep going.

Don't Wait Until It's Too Late

Ignoring early warning signs will compound problems. 

Foster a culture of open communication where team members feel comfortable raising concerns about potential delays early on. Address potential delays proactively to mitigate risks and prevent re-work. Projects that address potential delays early have a higher chance of staying within budget and maintaining stakeholder trust.

Raise alarms as early as possible so risks don’t spiral out of control.

Understand What Went Wrong

Missed timelines are often the result of unforeseen challenges, lack of clarity, or complexities, not a lack of effort. 

Instead of assigning blame, seek to understand the root causes and empathize with the team and people who worked tirelessly to deliver the project. Foster an environment of trust, collaboration, and continuous improvement. Provide the necessary support and resources to overcome obstacles.

Empathy leads to trust and resilience.

Learn from Failures

Missed timelines are not failures but opportunities to learn and improve. 

Conduct a thorough postmortem to understand what went wrong, identify areas for improvement, and implement changes to prevent similar issues. Embrace a growth mindset and continuously learn from mistakes. Celebrate the lessons learned and share them with the team.

Failures are stepping stones to success.


Missed deadlines are inevitable, but how you handle them as a product manager can make or break your credibility and the project's success. Embrace a proactive, data-driven, and empathetic approach to navigate the challenges and emerge stronger on the other side.

How I can help you:

  1. Fundamentals of Product Management - learn the fundamentals that will set you apart from the crowd and accelerate your PM career.
  2. Improve your communication: get access to 20 templates that will improve your written communication as a product manager by at least 10x.
May 15, 2024
Fundamentals of Product Management

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