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Fail Forward, Senior Scheduler Roles, Build Trust in 10 Minutes

Fail Forward, Senior Scheduler Roles, Build Trust in 10 Minutes

Micah Piippo
May 19, 2025

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Welcome back to Beyond Deadlines newsletter—a free perk for people looking to improve in Planning and Scheduling. Each week, we provide tactics, prompts, jobs and food for thought. We want you to succeed today, tomorrow and throughout the rest of your career.

If you’re not failing, you’re not pushing your limits, and if you’re not pushing your limits, you’re not maximizing your potential. Though this process of pushing your limits, of sometimes failing and sometimes breaking through—and deriving benefits from both your failures and your successes—is not for everyone, if it is for you, it can be so thrilling that it becomes addictive. Life will inevitably bring you such moments, and it’ll be up to you to decide whether you want to go back for more.

Principles by Ray Dalio

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How to Win Over the Construction Manager in 10 Minutes

You can craft the cleanest CPM logic, lock in your float, and forecast every scenario under the sun…

But if your Construction Manager doesn’t trust your schedule?

It’s just a spreadsheet with colors.

Here’s how to change that fast.

Before your next meeting or schedule walkthrough, run this quick "CM Pitch" play:

Step 1: Walk the Work

Ask yourself:

“If I had to build this job using this schedule could I?”

If you can’t mentally walk the site sequence from the schedule, chances are your CM can’t either.

Build your narrative like a builder would.

Step 2: Lead with What They Care About

Construction Managers aren’t interested in P6 layouts or Gantt art.

They care about:

Milestone certainty

Crew flow and handoffs

What’s about to break

Start your pitch with their priorities not yours.

Step 3: Show One Visual

Less is more.

Pick a single visual that tells a clear story. My go-to:

A 4-week lookahead

Grouped by area or system

Bonus: actual vs. plan by crew

Make it digestible. Make it relevant.

Step 4: Ask One Strategic Question

“If this schedule were 100% accurate… what could still go wrong in the field?”

This question disarms defensiveness and sparks collaboration.

It reframes the schedule as a tool not a scorecard.

This whole conversation takes 10 minutes.

But it can earn you weeks of credibility.

Because in construction, trust moves faster than data.

Win Over a Project Managers

Copy and paste this prompt into ChatGPT, Gemini or Claude.

Act like a highly experienced construction project management coach. You have worked with schedulers and project managers on over 300 successful commercial, residential, and infrastructure projects across the past 25 years. You specialize in helping construction schedulers develop communication strategies and scheduling presentations that foster trust, clarity, and buy-in from demanding project managers.

Your objective is to help a construction scheduler impress and win over their project manager through high-impact communication, data-backed scheduling insights, and proactive problem-solving. The goal is to gain the project manager's confidence and demonstrate leadership-level competence.

Follow this structured approach:

Understand the Project Manager’s Priorities
- List the top concerns and responsibilities of a project manager on large-scale construction projects.
- Explain what project managers typically expect from a scheduler in terms of communication, reporting, and collaboration.
- Identify common frustrations or red flags project managers experience with ineffective schedulers.
Build an Effective Communication Strategy
- Suggest a weekly update format that keeps the project manager informed but not overwhelmed.
- Recommend ways to proactively communicate schedule risks and trade delays without sounding alarmist.
- Include language patterns or phrases that build trust and highlight solutions, not just problems.
Develop a High-Impact Schedule Presentation
- Describe how to create a visual, data-rich summary of the schedule that even a non-scheduler can understand.
- Explain how to highlight critical path items, potential risks, and float in a way that shows foresight and leadership.
- Include methods for presenting schedule changes with rationale, stakeholder impacts, and mitigation strategies.
Demonstrate Strategic Thinking
- Offer tips on how to think like a project manager and anticipate their questions before they ask.
- Provide examples of proactive scheduling behaviors that earn trust, such as pulling in subcontractors early or sequencing inspections efficiently.
- Share a checklist of “scheduler-to-leader” behaviors that demonstrate the scheduler is thinking beyond dates and software.
Include a Sample Script or Email
- Write a short sample email a scheduler could send to their project manager that demonstrates professionalism, foresight, and collaboration.
- Optional: Write a brief 2-minute script the scheduler could use in a meeting to walk the PM through a critical update.