Tips For Keeping Projects On Deadline

How I Set Expectations So Things Don’t Slip as a Program Manager at Amazon Most deadlines don’t get missed because people are lazy. They get missed because expectations were unclear. At Amazon, alignment isn’t optional…it’s how we move fast without creating confusion. Here’s how I set expectations early…and keep things from slipping: 1/ I write down what “done” actually looks like ↳ Not just “finish the doc” ↳ But “complete draft with metrics, reviewed by 2 teams, and shared by Friday” Example: I once asked an SDE to finalize “the dashboard,” but they thought I meant visuals…I needed filters too. Now I write detailed definitions of done. 2/ I repeat timelines in writing ↳ Verbally aligned = easily forgotten ↳ Written timelines = shared truth Example: After any kickoff, I send a recap that includes the key milestones, owners, and due dates. If it’s not written, it’s not real. 3/ I ask people to confirm in their own words ↳ “Can you recap what you’re owning?” ↳ It surfaces misalignment early Example: I had someone say “Sure, I’ll get it done” but when I asked them to repeat the task, they described something completely different. Easy fix…because we caught it fast. 4/ I set check-in points…not just a final deadline ↳ Midpoints help course-correct ↳ It’s easier to fix week 1 than week 4 Example: For a 4-week launch, I add 2 mid-checks: one for progress, one for review. That’s saved me from last-minute fire drills. 5/ I clarify escalation paths up front ↳ “If you hit a blocker, who do you ping?” ↳ Removes friction when things go sideways Example: We once hit a resource crunch mid-project…because no one knew who could approve temp help. Now I list “go-to” escalation contacts in every kickoff doc. You don’t need to micromanage. You just need to make expectations unmistakable. How do you set clarity from day one?

For all my project schedulers out there... One of my best scheduling tips is to set aggressive (but not unreasonable) dates for key deliverables. When discussing a task with a team of engineers, I often ask, "What's a reasonable duration to budget for this"? When they respond, I'll follow up with, "What would we have to do to cut that in half?" Then, I'll push to get their buy-in on the more aggressive (read: shorter) duration. *BUT* I'll still plan for the successor tasks to begin closer to their initial "comfortable" date. To do this, I use the predecessor "lag" to build a buffer between tasks to allow for slippage. (The benefit is that I can avoid the trap of Parkinson's law and drive towards that aggressive date.) → Aggressive end date for the preceding task. → Comfortable start date for the successor task. → With a buffer in between. Sometimes, we use that buffer and arrive 'on time' to start the next task or phase. But, more often, we accomplish the aggressive dates and arrive ahead of schedule, and my team looks like heroes. ~~~ Do you ever use lags to set aggressive dates while preserving a buffer? What are your best tips for project scheduling? ____ 👋 Subscribe to my newsletter on my profile page for more streamlined enterprise project management tips. . .

Had a great chat with some fellow dev veterans about the basics of production—stuff that’s often missing on projects but makes a massive difference when done right. One big gap we kept coming back to: validating estimates. Here’s the thing: individual estimates might seem fine, but over time and across teams, they’re consistently off. That’s why it’s so important to measure and track the historical patterns of estimates vs. actual outcomes. When you do that, you start to see a truth—like a team that commits to X workload but only delivers 70% of it on average. With that insight, you can adjust future plans to set realistic expectations. This approach helps nail down milestones based on reality, whether that means prioritizing scope or sticking to a fixed deadline. If scope is king, you give the date. If the date is immovable, you define what can actually get delivered. When I interview production or program management candidates, at some point I always ask how they came up with their dates. Was it handed to them, or did they calculate it? Then I follow up with how they validated those dates were realistic? This is where most candidates stumble. Many just say, "The team told me what they could do by the date," and leave it at that. The problem is, people are notoriously bad at estimating, especially for long-term tasks and honestly, if you’re just taking estimates from the devs and passing them up the chain, I find myself wondering what value you're adding to this process in the first place. Why not skip you and go straight to the devs? In this process, a large value of the producer is in the validation step—digging into whether those dates hold up under scrutiny. After all, a big part of a producer's job overall is protecting the team, even from themselves. That means taking their estimates, validating what’s possible, and being the one to push back on both the team and communicate this out to the stakeholders. Without all that, you’re headed for crunch, every time. Learning to validate dates is one of the most important level-ups for associate and mid-level producers. Having this skill and being able to articulate how you do this can be the difference between landing a job or not. Then, once you’re on the team, it’s what sets apart producers who deliver from those who don’t. Hope this helps!