How to Make Sure Your Tech Team Actually Hits Deadlines

One of the ways I make my life easier is by having what my friends affectionately call “Jared Rules.” These rules remove decision fatigue and make sure I’m doing more of what I love and less of what I don’t.

A few Jared Rules I live by:

• When given an opportunity, always order the short rib sandwich
• Always check the faucet functions before soaping your hands in a public washroom
• Always use the bathroom before a flight
• Make sure a project is fully scoped before I take on a deadline

That last rule? It’s made my professional life exponentially easier and better. And it’s a rule I share with every client and friend when it comes to making sure your tech team actually hits the deadlines they give you.

Hiring a tech team is a big investment, and you need them to deliver on time. But if you’ve worked with developers before, you know that deadlines in tech can be… slippery.

Maybe you’ve been here before: you’re expecting a feature to go live next week, only to find out it’s still in development. Or you’ve planned a big launch, but last-minute issues delay everything.

Here’s how to make sure your hired tech team actually meets deadlines—and that you don’t end up stuck in endless delays.

1. Define What “Done” Actually Means

One of the biggest reasons tech projects miss deadlines? Misaligned expectations.

What you think is “done” might not be what your developers consider “done.” You might expect a feature that’s fully functional, tested, and ready for customers. But the development team might think it’s “done” as soon as the code is written—even if it hasn’t been tested or approved.

How to prevent this problem:

• Be specific about what “done” means. Does it mean fully tested? Approved by your team? Live in production? Get detailed. (Sidenote: this is one of the ways we help our clients avoid getting “stuck in the build.”)

• Don’t schedule meetings or launches until you’ve seen a working version. Never assume something is ready just because the team says it’s done. Ask for a demo before committing to a deadline.

• Set clear milestones. Instead of one big delivery date, break things into smaller checkpoints so you can track progress and spot delays early.
  

2. Always Plan for Delays (Because They Will Happen)

No matter how solid your plan is, things will go wrong. Bugs will pop up, unexpected issues will delay approvals, and external systems (like Apple’s App Store not accepting builds for some unknown reason) will throw curveballs at the last minute.

A common mistake? Assuming everything will go smoothly and locking in a launch date before you’ve built in buffer time.

How to protect yourself from last-minute delays:

• Add a buffer to every deadline. If your tech team says a feature will take four weeks, expect five or six to allow for unexpected, and uncontrollable delays

• Anticipate external delays. If your product relies on third-party approvals (like Apple, Google, or a payment processor), assume it will take longer than expected. Many teams have launched late because they didn’t realize approval times can vary wildly.

• Avoid hard launch dates before testing. If you’re announcing a product launch or a big update, make sure the feature is actually working before setting a public deadline.
  

3. Expect Roadblocks—And See How Your Team Handles Them

Tech projects never go exactly as planned. The difference between a tech team that delivers and one that struggles? How they handle problems when things go wrong.

The best teams don’t panic when they hit an issue—they collaborate on solutions. But some teams try to avoid tough conversations, downplay problems, or scramble at the last minute.

How to evaluate your tech team’s problem-solving skills:

• Pay attention to how they communicate setbacks. A good team will be upfront about challenges and offer solutions. A weak team will stay quiet until the last minute.

• Encourage a problem-solving mindset. Instead of pointing fingers, focus on how to fix things and prevent future issues. Because software development is non-linear and imperfect.

• Look for a team that adapts. Are they actively improving the process as they go? Or are they repeating the same mistakes?
  

4. Push for Bigger and Better—Not Just the Bare Minimum

If you’re hiring a tech team, you don’t just want okay results. You want great results. But a lot of teams fall into the trap of doing just enough to meet the requirements without thinking about how to make the product better, faster, or more scalable.

The best tech teams challenge assumptions, suggest improvements, and bring fresh ideas—not just follow orders.

How to ensure your tech team pushes beyond the basics:

• Encourage innovation. Ask your team: “Is there a better way to do this?” You hired experts—so let them bring ideas to the table.

• Stay ahead of industry trends. The best teams keep up with new tools, frameworks, and best practices. Make sure your team isn’t stuck in outdated methods.

• Review performance after each milestone. After each major delivery, do a quick retrospective: What worked? What didn’t? What could be better? This keeps the team growing and improving.

5. Communication is Everything—Set Clear Expectations from Day One

If a tech team is missing deadlines, it’s usually not because they’re bad at coding—it’s because communication broke down somewhere along the way.

Maybe requirements weren’t clear. Maybe they misunderstood priorities. Maybe they thought they were on track, but no one flagged early warning signs.

Great communication doesn’t mean endless meetings—it means everyone knows what’s happening, what’s expected, and what needs to get done next.

How to improve communication with your tech team:

• Set up regular check-ins. Weekly or bi-weekly updates ensure you stay in the loop without micromanaging.

• Use the right tools. Project management tools like Trello, Jira, or Asana help track progress without relying on messy email chains.

• Ask for demos, not just status updates. Instead of just hearing “Yeah, we’re on track,” ask to see the progress in action.

• Be direct about concerns. If something doesn’t seem right, bring it up early—before it turns into a bigger issue.
  

When a tech team consistently misses deadlines, it’s not just frustrating—it breaks trust. If you can’t rely on your team to deliver on time, it creates a ripple effect across the entire business.

But by setting clear expectations, building in buffer time, focusing on problem-solving, and pushing for bigger and better, you don’t just get a team that meets deadlines—you get a team that builds something great.

If you’re hiring a tech team (or already working with one), use these strategies to keep your project on track and avoid expensive delays. Because in tech, timing is everything.