🎯 Expertly Handle (and Recover From) Big Mistakes

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🔹 Vice President – Program Executive (Systems)
Company: Metropolitan Transportation Authority (MTA)
Location: New York, NY
Format: Hybrid (telework 1 day/week)
Apply: Apply here
The Vice President Program Executive manages capital projects and program delivery within MTA’s Systems business unit, ensuring projects are safe, on schedule, and on budget. The role oversees high‑impact initiatives—including high‑speed communications networks, CCTV, and public‑address systems—and mitigates risks, resolves issues, and coordinates across internal teams, operating agencies, consultants, and contractors. This executive mentor and leader also monitors progress against agency goals and ensures adherence to safety, quality, and regulatory standards.

🔹 VP, Emergency & Disaster Management
Company: ICF
Location: Reston, VA (U.S.-based with travel)
Format: Flexible/Remote
Apply: Apply here
ICF’s disaster-management division seeks a transformational leader to guide its portfolio of hazard-mitigation, response, recovery, and resilience programs. Reporting directly to the division leader and overseeing a 250‑plus person organization, the VP sets strategic direction, mentors high‑performing teams, drives sales and business growth with state and local agencies, and can be based anywhere in the continental U.S. with travel to client meetings, conferences, and project sites.

🔹 Senior Vice President, Client Operations & Transformation
Company: Registrar Corp
Location: Remote, U.S.
Format: Remote
Apply: Apply here
Registrar Corp is seeking a strategic leader to head its client operations and transformation organization. This fully remote SVP role builds and executes a comprehensive client‑operations strategy, leads and scales a 60‑plus‑person team, and ensures high‑quality delivery of regulatory services to 32,000. Responsibilities include meeting service‑level and quality targets, implementing process automation and AI tools to improve speed and accuracy, coaching managers to foster a culture of accountability and continuous improvement, and collaborating with Sales, Product, Finance, and HR.

🔹 Corporate Vice President – Head of Transformation Management Office (TMO)
Company: New York Life
Location: New York, NY
Format: Hybrid (3 days per week)
Apply: Apply here
As head of the Transformation Management Office within Technology’s COO organization, this leader orchestrates New York Life’s multi‑year transformation agenda across Technology, Data, and AI. The role defines the TMO operating model, establishes delivery standards, and governs how transformation initiatives are prioritized and executed. You will personally manage high‑impact programs, coach and develop program and project managers, and serve as a strategic catalyst for modernization, workforce evolution, and value realization

🔹 Director, Technical Program Management
Company: Warner Bros. Discovery
Location: Atlanta, GA
Format: Hybrid
Apply: Apply here
Warner Bros. Discovery is looking for a visionary Director of Technical Program Management to lead a portfolio of strategic, high‑impact programs for WBD Sports. The role, based in Atlanta and designated as hybrid, involves overseeing simultaneous initiatives across engineering, product, and operations, ensuring delivery of scalable, high‑quality software and driving cross‑functional alignment. You’ll coach and grow a team of technical program managers, define project milestones, manage dependencies, and balance long‑term strategy with tactical execution while championing customer needs and fostering innovation.

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Bots Take the Wheel

The Problem: When deployments fail or incidents occur, teams scramble to understand what happened—but by the time they start investigating, critical context is already lost.

The Fix: Automate post-mortem creation so the investigation starts immediately, while details are fresh.

Real Use Cases:

TL;DR: Don't let failures go unexamined. Automate post-mortem creation so every significant incident generates a structured review. The best organizations don't just recover from mistakes—they build systems to learn from them and prevent repeats.

Visionary Voices

Quote: "Failure isn't a necessary evil. In fact, it isn't evil at all. It is a necessary consequence of doing something new." (Source: Creativity, Inc.)

Ed Catmull built Pixar from a struggling hardware company into the most successful animation studio in history. But here's what makes his leadership philosophy relevant to this issue: He normalized failure.

Under Ed's leadership, Pixar created a culture where mistakes weren't just tolerated—they were expected. Every film went through a "Braintrust" process where directors presented work-in-progress and received brutally honest feedback. Early cuts of Pixar films were terrible. Always. And that was okay.

On Handling Failure:
Ed argues that most organizations say they want innovation, but they punish failure. The result? People hide mistakes, avoid risks, and optimize for not getting in trouble rather than doing great work.

Pixar's approach was different: Make failure cheap and fast. Iterate. Learn. Improve.

In Creativity, Inc., Ed writes about the early crisis with Toy Story 2. The film was a disaster nine months before release. The team had to scrap most of it and start over. It could have been Pixar's first failure.

Instead, they faced it directly. They brought in fresh eyes, gave honest feedback, and rebuilt. Toy Story 2 became one of Pixar's best films.

On Post-Mortems:
After every film—success or failure—Pixar conducts a detailed post-mortem called a "Post-Release Retrospective." The goal isn't blame. It's learning.

Key rules:

Ed writes: "If you aren't experiencing failure, then you are making a far worse mistake: You are being driven by the desire to avoid it."

On Rebuilding Trust:
When Pixar acquired by Disney, Ed became President of Disney Animation—which was in crisis. Multiple failed films. Demoralized teams. Broken culture.

His approach wasn't to blame. It was to rebuild systems:

Result? Disney Animation's turnaround: Frozen, Zootopia, Moana.

What You Can Learn From Him:

Where to Learn More:

Why He Matters to Delivery Professionals:
Delivery leaders live in the gap between "the plan" and "what actually happened." Projects slip. Deployments fail. Stakeholders get upset.

Ed's frameworks prove that how you handle failure matters more than avoiding it. Organizations that learn from mistakes get stronger. Organizations that punish mistakes get more skilled liars.

If you've ever hidden a problem hoping it would go away, or watched a team cover up a failure instead of learning from it—Ed's work is your roadmap to building something better.

Final Word:
Ed Catmull proves that the best organizations don't avoid failure—they create systems that make it safe to fail, learn fast, and come back stronger. That's not just good culture. That's a competitive advantage.

Discover the six proven strategies that transform technical program managers from perceived overhead into trusted engineering partners who drive successful program delivery.

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Professional Development

Let's be honest:

You're going to screw up. Maybe you already have.

A project will fail. A deployment will break production. You'll give bad advice to an executive. You'll miss a critical deadline. You'll cost the company money.

The question isn't if you'll make a big mistake. It's how you'll handle it.

Let me show you.

When you realize you've made a major mistake, your instinct will be to hide, deflect, or panic.

Don't.

Here's what to do instead:

Step 1: Stop the Bleeding (Immediately)

Before you do anything else, assess: Is the problem still happening?

If yes, your first job is containment:

Example:

Bad: You realize a bug shipped to production Friday at 5 PM. You think "I'll deal with it Monday."
Good: You immediately notify on-call, pull the release, and post in #incidents: "Bug in prod. Rolling back now. Will investigate root cause."

Why this matters: Executives forgive mistakes. They don't forgive negligence. If you hide a problem and it gets worse, that's career-limiting.

Step 2: Own It Publicly (Within 2-4 Hours)

Once the immediate crisis is contained, communicate clearly to whoever needs to know.

The format:

Subject: [Issue] - Status Update

"Quick update on [what went wrong]:

What happened: [One sentence describing the mistake]
Current status: [Is it fixed? Still broken? Being investigated?]
Impact: [Who/what was affected?]
Next steps: [What you're doing to fix it]
Timeline: [When will you have more info?]

I take full responsibility. Will share full RCA by [date]."

Example:

"Quick update on the Q2 roadmap I presented to the client:

What happened: I stated we could deliver Feature X by June. That timeline was wrong—the actual delivery is August due to platform dependencies I missed.

Current status: I've informed the client and proposed an interim solution.

Impact: Client is reconsidering the deal. Sales and Product are looped in.

Next steps: Meeting with client tomorrow to discuss revised timeline and mitigation options.

Timeline: Will have resolution path by EOD Friday.

I take full responsibility. This was my error."

Why this works:

Step 3: Do NOT Over-Apologize

Bad: "I'm so sorry. I can't believe I did this. I feel terrible. I'm such an idiot."

Good: "I made a mistake. Here's what happened, here's the fix, and here's how I'll prevent it going forward."

Why: Over-apologizing signals lack of confidence. Executives want to know you can handle the pressure, not that you're emotionally falling apart.

Within 48-72 hours of a major mistake, you need to write a post-mortem.

The goal: Document what happened, why, and how to prevent it from happening again.

Post-Mortem Template:

1. Summary

2. Timeline

3. Root Cause Analysis

4. What Went Wrong

5. What Went Right

6. Action Items

7. Lessons Learned

Example Post-Mortem (Abbreviated):

Summary:
On March 15, I presented an incorrect timeline to Client X during a roadmap review, stating Feature Y would ship in June. Actual delivery is August due to platform dependencies I failed to account for. Client is now reconsidering a $2M deal.

Root Cause:
I didn't validate the timeline with Engineering before presenting it. I relied on outdated notes from a January planning session that didn't account for Q1 scope changes.

What Went Wrong:

What Went Right:

Action Items:

Lessons Learned: Never commit to timelines without validating with Engineering first. Outdated information is worse than no information.

Why this matters:
A good post-mortem shows:

Executives promote people who learn from mistakes, not people who never make them.

After a major mistake, trust is damaged. Here's how to rebuild it:

Strategy 1: Deliver Flawlessly on the Next Thing

The Problem: After a big failure, people are watching you closely. If you stumble again, they'll write you off.

The Solution: Your next project needs to be perfect.

How:

Example:

After the botched client timeline, you're assigned a smaller project. You:

The Result: People start thinking "That timeline mistake was a fluke. They're back on track."

Strategy 2: Acknowledge It Once, Then Move Forward

The Problem: Some people keep apologizing or referencing their mistake months later. It becomes their identity.

The Solution: Own it once. Learn from it. Then stop bringing it up.

Example:

Bad: Six months later, you're in a meeting and say: "Yeah, I know I screwed up the Client X timeline, so I'm probably not the best person to..."

Good: Six months later, someone asks you about timelines. You say: "I learned a hard lesson about validation last year. Now I always cross-check with Engineering before committing. Here's the process I built..."

The Difference: The second version shows growth. The first shows you're still stuck in the past.

Strategy 3: Become the Expert on What You Broke

The Problem: After a failure, people wonder if you're capable.

The Solution: Become the go-to person on that specific problem.

Example:

You missed a critical dependency that caused a project delay.

Now:

The Result: You've turned your failure into expertise. That's how you rebuild credibility.

Not all mistakes are created equal. Here's how to tell the difference:

Recoverable Mistakes:

Career-Limiting Mistakes:

Example:

Recoverable: You estimated a project would take 8 weeks. It took 12 because of unforeseen technical complexity. You communicated proactively, adjusted the plan, and delivered.

Career-Ending: You knew the project would take 12 weeks, but told stakeholders 8 weeks to look good. When it slipped, you blamed Engineering and tried to cover it up.

The Difference: Intent, honesty, and learning.

Sometimes, you'll get blamed for things that weren't entirely your fault.

How to Handle It:

A. Separate Facts from Narrative

Document what actually happened vs. what people are saying happened.

Example:

Narrative: "You missed the deadline and cost us the deal."
Facts: "The deadline was set before I joined. I flagged risks three times in writing. Leadership chose not to adjust scope."

B. Own Your Part (But Not More)

"Here's what I could have done better: [X]. However, I want to clarify the full context: [Y]."

C. Escalate If Needed

If you're being unfairly blamed, escalate to your manager or HR with documentation.

Example Email:

"I want to address the narrative around Project X. I take responsibility for [specific thing I did wrong]. However, there's important context: [facts]. I have documentation showing [evidence]. I'm happy to discuss."

Sometimes, the mistake isn't recoverable—not because of what you did, but because of how the organization responds.

Signs it might be time to leave:

If this is the case: Update your resume, reach out to your network, and find an organization that treats failure as a learning opportunity.

Here's the truth:

Every executive I know has a "career-defining failure" story. The moment they almost got fired. The project that blew up. The decision that cost millions.

What separates them from people who plateau? They used the failure as fuel.

How to reframe failure:

The best leaders aren't the ones who never fail. They're the ones who fail, learn, and come back stronger.

TL;DR: When you screw up, act fast. Stop the bleeding immediately, own it publicly within hours, and skip the over-apologizing. Write a blameless post-mortem focused on systems, not people. Rebuild trust by delivering flawlessly on your next project, becoming the expert on what you broke, and moving forward without dwelling on the past. Most mistakes are recoverable if you handle them with transparency, accountability, and learning. The difference between recoverable and career-ending is honesty and growth. Every executive has failed—the best ones used it as fuel.

That's a wrap on this 4-week series. You've learned how to show executive presence, navigate difficult meetings, lead quietly, and recover from major mistakes. Now go build the career you deserve.

Wanna chat IRL? Connect with me on LinkedIn and we can set up some time.

The Delivery Career Decoder shows why you’re already qualified for more—and how to prove it.

I love feedback. If you have topics you want to see? Or thoughts or ideas on how to serve the community better, please hit reply or email [email protected].

Until next time,

The Business of Delivery

Quiet moves. Bold Careers.