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When Deadlines Don't Matter: The Hidden Cost of Poor Accountability

How to hold people accountable without becoming the office villain

Hi! Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.

Picture this: It's Monday morning, and you're staring at your project board.

Half the tasks that were supposed to be done Friday are still sitting there, mocking you.

The product launch that was meant to go live this week got pushed back again.

For what feels like the fifth time.

Probably because it has been pushed back five times.

The engineering team swears they're "almost done," marketing is scrambling to adjust their timeline, and your CEO is asking why everything always takes longer than expected.

Sound familiar?

👉 One of my greatest observations while working with companies is that most operators swim in mediocrity.

Missed deadlines become the norm. Subpar work gets accepted because "at least something got delivered." Product launches fail, bugs make it to production, and everyone just shrugs and says, "Well, we're moving fast. Whatever.”

But here's the thing - this isn't a people problem. It's a systems problem.

I've coached hundreds of operators who come to me frustrated with their teams.

They call their employees "slackers" and complain about accountability. But when I dig deeper, I find the same pattern every time: they never set up systems to make accountability easy in the first place.

No clear deadlines. No obvious consequences. No explanation of why the deadline matters. Just arbitrary dates thrown around in meetings that nobody takes seriously.

Today, I'm sharing the playbook I use with operators who want to transform their teams from deadline-missing to deadline-crushing machines. Let’s jump in.

The Playbook on Building Real Accountability

Step 1: Set up your accountability infrastructure 📋

Before you can hold anyone accountable, you need the basic infrastructure in place. Without this, you're just another manager complaining about missed deadlines.

✅ The Master Task Board

Every high-performing team I work with has one central place where all actions live. Whether it's project-based or team-based, this board tracks everything.

Your task board should include:

1. Who owns what (one DRI per task)

2. Clear due dates

3. Current status (not started, in progress, blocked, done)

4. Dependencies between tasks

"The best operators never chase people down for updates. Their systems do the chasing for them."

📝 Meeting Memos with Action Lists

Every single meeting needs a memo. Not optional. Not "when we remember." Every meeting.

Your memo structure:

1. Recap of previous actions (start with accountability from last time)

2. Meeting agenda and discussion

3. Action items with owners and dates (end with clear next steps)

This creates a paper trail that makes accountability conversations much easier. When someone misses a deadline, you can point to exactly what they committed to and when.

♾️ Weekly Project Updates

Have your project managers or operators own a weekly memo that basically says: "This is the stuff you owe me."

This memo should highlight:

1. What's on track

2. What's behind

3. What's blocked

4. Who owns what actions this week

Step 2: Make deadlines meaningful 💡

Most deadlines feel arbitrary because leaders never explain the "why" behind them.

😠 Connect deadlines to consequences

Don't just say "We need this by Friday." Say "We need this by Friday because the marketing team is launching their campaign Monday, and if we miss this deadline, we'll have to push the entire launch back two weeks."

🤝 Get explicit buy-in

Ask directly: "Can you commit to getting this done by [date]?" Wait for a verbal yes. This isn't micromanaging - it's creating clarity.

🌈 Set stretch vs. standard KPIs

Borrow from the approach in the example above:

1. Standard KPIs: Should be achievable with good execution

2. Stretch KPIs: Push the team to see what's possible with exceptional effort

Step 3: Address missed deadlines immediately 🗣️

Here's where most operators completely blow it. They either ignore missed deadlines or turn into angry dictators. Neither works.

⚠️ For first-time deadline misses (done in group meetings):

"Did you complete [specific task]? No? Okay, let’s talk about what happened.”

Listen to their explanation, then:

1. Ask them to own their part: "What could you have done differently to hit this deadline or flag the issue earlier?"

2. Set clear expectations: "Moving forward, I need you to [specific behavior change]"

3. Push for accountability: "What support do you need to make sure this doesn't happen again?" 

🛑 For repeat offenders (private conversation):

Same structure, but with firmer consequences:

1. Own your part: "I messed up by giving you too many chances without clear consequences"

2. Their accountability: “Where can you own what has happened?”

3. Performance improvement plan: "Here's exactly what needs to change and by when"

4. Clear consequences: "If these milestones aren't met, we'll need to discuss your role here"

5. Support offered: "What do you need from me to succeed?"

Step 4: Create a culture where accountability is normal 🎯

The goal isn't to become the deadline police. It's to create an environment where missing deadlines feels weird, not normal.

👥 Public accountability in team settings

Address missed deadlines in group meetings, not behind closed doors. This isn't about shaming people - it's about normalizing the conversation.

"Sarah, you were supposed to have the wireframes done yesterday. What's the status?"

Keep it factual, not emotional. The team learns that deadlines actually matter.

🎉 Celebrate deadline crushers

When someone delivers on time or early, call it out publicly. Make it clear that hitting deadlines is valued and noticed.

☝️ Use daily standups for momentum

Steal this tactic: Set up a bot that asks daily "What are you doing today that helps us hit our stretch goal?" Responses go to a team channel.

This keeps the goal front of mind and creates gentle peer pressure.

🚧 Make retrospectives about urgency, not just delivery

During sprint retros, ask: "How did our sense of urgency feel this sprint? What created aliveness and energy toward our shared goal?"

This reinforces that the team's energy and commitment matter as much as the specific deliverables.

When Goals Get Missed

Sometimes, despite your best systems and conversations, big goals still get missed. Here's how to handle it without destroying team morale or setting a precedent that goals don't matter:

  1. Acknowledge the miss directly: "We didn't hit our target. Let's talk about why."

  2. Source the real reasons: Ask the team what went wrong and what could have been better. No finger-pointing, just honest assessment.

  3. Reinforce that missing isn't okay: "We worked hard and should be proud of what we accomplished, but missing this goal impacts [specific consequence]."

  4. Reset with energy: "This means next quarter becomes even more important. Here's what we're aiming for..."

The key is holding both truths: you can be disappointed about the miss AND proud of the effort. Teams need to know that goals matter without feeling like their jobs are on the line every sprint.

[read more - Six Mistakes to Avoid When Firing Someone - Handle the hardest conversations with grace]

The Bottom Line

Poor accountability isn't a character flaw in your team - it's a systems flaw in your leadership.

When you set up clear tracking, meaningful deadlines, and consistent follow-through, hitting deadlines becomes the path of least resistance. When you don't, missing deadlines becomes normal.

Your job as an operator isn't to chase people around asking for updates. It's to create an environment where accountability happens naturally because the systems make it easy and the culture expects it.

Stop blaming your team for missing deadlines. Start building the infrastructure that makes hitting them inevitable.

Until next time,

And if you’re reading this - you're already ahead.

Because you know where to find the stuff that’s actually good. Like my templates and resources, and this newsletter.

Resources Mentioned 📌 

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Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale).

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her husband, daughter, and Formosan Mountain Dog, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.

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