Why do smart teams still deliver failed projects?

Most project failures don't begin with a catastrophic mistake. Instead, they begin with small deviations—minor compromises that seem harmless in the moment. A warning sign gets ignored. A shortcut becomes acceptable. A risk is acknowledged but tolerated because "nothing bad happened last time." Over time, those deviations quietly become the new normal.

In this episode of Project Management Happy Hour, Kim Essendrup and Kate Anderson sit down with Dr. Bill Brantley to explore one of the most dangerous patterns in project leadership: normalization of deviance.

The concept comes from sociologist Diane Vaughan's analysis of the Challenger space shuttle disaster. Engineers had long observed problems with the shuttle's O-ring seals. But earlier launches survived those anomalies. Each successful launch reinforced the belief that the risk was acceptable. Gradually, what began as an abnormal warning became accepted behavior.

As Dr. Brantley explains:
"We survived that near miss. It's okay. Next time we'll be okay."

Project teams fall into this pattern all the time.

A design review is skipped because the team is behind schedule.

A test failure gets dismissed because it hasn't caused a real problem yet.

A risk gets documented—but never truly addressed.

Nothing breaks immediately. So the project keeps moving.

The conversation explores how this slow drift toward failure mirrors patterns seen in aviation, engineering disasters, and even mountaineering expeditions. Experienced professionals—people who know better—gradually normalize increasingly risky decisions until the system finally breaks.

But the episode goes further than just diagnosing the problem. Dr. Brantley and the hosts dive into the decision dynamics inside projects.

A typical project team makes dozens—or even hundreds—of decisions every week. Some have immediate consequences, while others take months or years to reveal their impact. One story from the Apollo program illustrates this perfectly: a weld defect made years earlier ultimately contributed to the crisis of Apollo 13.

This delay between decision and consequence creates a dangerous blind spot. Dr. Brantley jokingly calls it the "White Castle effect."

"White Castle burgers are great going down… and then at three in the morning you realize you made a bad decision."

The same thing happens in project management. Decisions that seem harmless in the moment can produce painful consequences much later.

One of the most powerful insights from the discussion is that organizations often fail to reflect on their decisions. Teams act, move forward, and stay busy—but rarely pause to ask whether their decisions are actually improving outcomes.

That reflection step is critical.

"Reflection really helps you break that normalization of deviance."

Without it, teams never notice when small compromises start compounding into systemic risk.

The episode also explores practical techniques for improving project decision-making. One of Dr. Brantley's favorites is red teaming—a method borrowed from military strategy and cybersecurity. In a red-team exercise, someone deliberately challenges the plan and tries to break it. Their job is to expose weaknesses before reality does.

It's a powerful way to counter groupthink and create psychological safety for dissent.

Another theme throughout the conversation is something many project managers intuitively know but rarely articulate: Every action—or inaction—on a project is ultimately a decision.

"Everything is a decision. Nobody is going to come after you around anything other than decisions."

Whether it's changing scope, delaying work, ignoring a risk, or choosing not to act at all, project leaders are constantly making decisions that shape the outcome of the project.

The real question isn't whether decisions are happening.

It's whether those decisions are intentional, visible, and thoughtfully examined.

Because in many projects, failure doesn't arrive suddenly.

It arrives slowly—one accepted deviation at a time.

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Have you ever gotten feedback that made you want to flip a table because it was both insulting and totally useless?

In this Top Shelf Replay, we revisit "They Told Me I'm Too Nice" and break down what that kind of vague feedback is really doing (sometimes gendered, almost always inactionable), why it hits so hard, and how to respond without spiraling - or people-pleasing your way into a personality transplant.

Then we go beyond the original episode with practical, real-world tactics: how to ask better follow-up questions, how to force examples without sounding defensive, how to "prime" your manager before a meeting so you get usable feedback, and how to figure out whether your boss is actually trying to coach you… or just dumping drive-by advice from a book they skimmed on a flight.

If you lead people, we also flip the lens: how to avoid giving your team confusing feedback that basically translates to "please be a different person," and how to coach toward outcomes instead of vibes.

• Treat vague feedback as a starting point, not a conclusion. Thank them, then ask them to say more until you have something observable and specific.

• Ask for examples on demand. Use: "Can you tell me about a time I did that well?" or "Who does that really well?" This forces specificity and gives you a model to study.

• Match your effort to their effort. If it was a drive-by comment, don't burn three weeks of anxiety trying to decode it. If they clearly invested in you, invest back proportionally.

• Prime your manager before a meeting so they know what "good" looks like. Tell them your goal (scope agreement, signature, commitment, decision) so their feedback anchors to outcomes, not vibes.

• If you want feedback, specify what kind you want. "I'm not looking for grammar edits—I want alignment on strategy" is a transferable skill for stakeholder reviews and exec comms.

• For managers: don't "coach" people who don't want coaching. Find out what they want first, or you'll waste time and damage trust.
  
  

• "I don't need you to be my Grammarly when you review this document. I need to know if we are strategically aligned."

• "Below the line? You just crossed the line, buddy."

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"Three PMs walk into a bar: a business PM, an IT PM, and a Vendor PM…" Sounds like a bad joke, but if you don't get it right - the joke will be your project.

Very often, you aren't the "one PM to rule them all" on your project - you may have other PMs involved that you need to work with. But how do you decide who does what, and how do you prevent turf wars from turning your project into a slow-motion train wreck?

In this episode, we ditch the corporate fluff to dive into the messy reality of projects with "too many cooks". We discuss how to navigate the friction between different project management roles, how to handle "useless" vendor PMs who won't manage their own resources, and what to do when an executive buyer bypasses you to talk directly to the vendor. You'll learn how to look "one level up" in the hierarchy to identify what actually drives your counterparts and how to draw professional boundaries that keep you in the driver's seat.

In this episode, you'll learn:

• How to use the "Hierarchy Hack" to uncover your counterparts' hidden motivations.

• Strategies for handling a vendor PM who refuses to do their job.

• Why a high-level human conversation beats a technical tool every time.

• The "Time and Materials" pivot to force vendor accountability.

• How to professionally block an executive from undermining your role.

From this episode:

• "The first thing to do is to have a conversation and, honestly, call it out in the open." — Kate

• "One of the ways I like to think about situations like this is one level up in the hierarchy." — Kim

• "I've been like, 'No, you can talk to me. Shut up, talk to me.'" — Kate

• "If I and my team are going to be held accountable... I have to be able to plan what we're accountable for." — Kim

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Project managers are constantly told they need to "learn how to say no."
But in the real world—especially when the ask comes from a sponsor, executive, or important customer—just saying no often isn't productive, strategic, or even possible.

In this Top Shelf Replay episode of Project Management Happy Hour, Kim Essendrup and Kate Anderson revisit one of the show's earliest "Appetizer" episodes: Say No by Saying Yes, originally aired in 2017. Short, deceptively simple, and still painfully relevant, this episode breaks down a technique that helps project managers protect scope, schedule, cost, and sanity—without sounding combative or inflexible

The core idea is straightforward:
Instead of responding to tough requests with a flat "no," you respond with "yes—but" or "yes—and here's what that would require."

"Yes, we can do it faster—but it will require triple the resources."
"Yes, we can release both languages at once—but we'll need more budget or a delayed launch."
"Yes, we can remove that resource—but you'll need to help me explain the downstream impact to the sponsor."

This approach reframes the conversation away from emotion and into trade-offs, which is where real project leadership lives.

As the conversation unfolds, Kim and Kate explore why this technique works so well psychologically. Leaders—especially busy executives—often don't have full context. Their "ridiculous asks" aren't always malicious; they're frequently driven by incomplete information, pressure from above, or a misunderstood business constraint. Saying "yes" first acknowledges their goal, signals partnership, and keeps them engaged long enough to hear reality

The episode also connects this technique to a broader leadership pattern the hosts have refined over the years: what they now describe as "affirm, caution, query."
You affirm the request.
You surface the risk or constraint.
You return the decision to the person who actually owns it.

In other words, you stop absorbing problems that don't belong to you—and you stop shielding leaders from the consequences of their own decisions.

The replay discussion expands the idea further, touching on burnout, executive presence, and why many project managers get stuck in a defensive "control mindset" around the triple constraint. Kim and Kate argue that stepping back—mentally taking off the project manager hat and putting on the sponsor's hat—makes these conversations easier, calmer, and more strategic. When you focus on outcomes instead of guarding boundaries, you stop reacting and start partnering.

There's also an unexpected but memorable parallel: gentle parenting.
The same structure used to redirect an emotional five-year-old ("I see what you want—but here are your options") turns out to work remarkably well with stressed executives, difficult customers, and unrealistic stakeholders. You don't remove agency; you structure it.

Ultimately, this episode is about more than saying no politely.
It's about changing the power dynamic—from executor to partner.
From order-taker to decision facilitator.
From "blocking progress" to helping leaders make informed choices.

If you've ever been handed an impossible deadline, an under-funded scope change, or a request that made your stomach drop, this episode gives you language, structure, and confidence to respond without burning trust—or yourself.

Thinking about going contractor? Kate and Kim share how they each left corporate and made the leap—two very different stories (burnout vs acting early) with the same core truth: contracting is built on relationships, reputation, and value… not job boards and commodity rates.

We cover how to know if you're ready, why sales is part of the job, what to watch out for (hello, 2008), and how to avoid racing to the bottom.

Want us to teach the full process with scripts + steps? Head to http://pmhappyhour.com/be-free.

As project managers, we spend a lot of time talking about tools, processes, and delivery frameworks—but far less time talking about the invisible structure that holds projects together: trust.

In this Top Shelf Replay episode of Project Management Happy Hour, Kim Essendrup and Kate Anderson revisit one of the show's earliest and most enduring concepts: Trust Bricks. Originally recorded in 2018, this short but powerful episode explores how trust is built—not through grand gestures or heroic saves—but through consistent, everyday actions that compound over time.

The core idea is simple: trust is predictability. When you repeatedly do what you say you'll do—whether that's sending meeting notes on time, honoring estimates, or showing up prepared—you lay one small Trust Brick at a time. Over weeks, months, and years, those bricks form a structure strong enough to withstand missed deadlines, bad news, or the occasional broken promise.

Kim and Kate break down why Trust Bricks matter so much in project environments:

• Teams are more honest with you when they trust you

• Estimates improve when people believe they won't be punished for telling the truth

• Difficult conversations become easier when everyone believes you're on the same side

• Sponsors give you more latitude when your track record is consistent

The conversation also explores what happens when trust breaks—and how the same Trust Brick approach can be used to rebuild credibility. Rather than trying to restore trust with a single "big win," the hosts argue that rebuilding starts small: partial deliverables, frequent check-ins, and deliberately meeting micro-commitments until confidence is restored.

In the replay commentary, Kim and Kate reflect on how their thinking has evolved since the original recording. They discuss:

• The role of showing up consistently, even when no explicit promise was made

• How trust operates differently in virtual and remote teams

• Why strong performers can accidentally set expectations that lead to burnout

• How leaders vary widely in how much "trust damage" they tolerate before overreacting

The episode also revisits the journey of Trust Bricks beyond the podcast, including Kim's experience delivering a TEDx talk on the topic and refining the framework into three enduring lessons:

1. You are always building or breaking Trust Bricks—whether you realize it or not

2. Missed expectations don't pause trust building; they actively tear it down

3. Unspoken expectations are the fastest way to accidentally destroy trust

This episode is a reminder that trust isn't soft, vague, or optional—it's a core delivery skill. If you want stakeholders who back you, teams who tell you the truth, and projects that don't require constant firefighting, it starts with sweating the small commitments.

The next time you make a commitment—big or small—ask yourself:
Am I laying a brick… or cracking one?

Check out Kim's TEDx talk at trust-bricks.com or on the TED youtube channel

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Kim and Kate settle in for a classic PM Happy Hour episode — the kind where the drinks are metaphorical, the conversation is wandering in the best way, and the insights sneak up on you. This one covers three big themes that hit close to home for project managers, leaders, and anyone who's ever had to keep a project — or a career — moving forward despite chaos.

It starts with a deceptively simple question: How do you describe what a PM actually does for a living? Kim brings his favorite one-sentence description, and Kate immediately pokes at it (lovingly) to reveal the gaps between a tidy definition and the messy reality of day-to-day PM work. Together they break down the core functions that aren't on the job description: expectation-setting, alignment-building, timeline-translating, political-atmosphere-reading. Yes, PMs manage plans — but they also manage humans, assumptions, ambiguity, and the definition of "done," which shifts more than anyone wants to admit. The conversation hits on why this matters so much for stakeholder alignment, project success, and your own sanity.

From there, the discussion pivots to fear in decision-making — specifically, how fear quietly creeps into choices that leaders and teams make every day. Kim shares a general's perspective on why big decisions get stalled ("people won't make hard decisions if it forces them to change"), and Kate adds their own real-world examples of hesitation disguised as caution. They unpack how fear leads to risk-avoidant behavior, analysis paralysis, unnecessary escalations, or decisions that look safe but actually create more work downstream. This part of the conversation digs into the psychology of leadership, the emotional drivers behind "bad" decisions, and how project managers can spot when fear — not logic — is driving a stakeholder's position. Along the way, they also reflect on why PMs sometimes avoid decisions themselves, even when they know the right call.

Finally, Kim and Kate open up about what they've learned from going out on their own and being their own boss — the good, the bad, and the "wow, nobody warned me about this part." They talk candidly about leaving stable corporate paths, the discomfort of striking out solo, the thrill of autonomy, and the realities of running a business while also running your own mental health. Listeners get the inside picture of what independence really looks like: the freedom, the discipline, the failures, the self-doubt, and the eventual confidence that comes from owning your decisions and your livelihood. This segment offers honest lessons learned for anyone considering consulting, freelancing, starting a business, or just trying to build a healthier professional life.

Through all three topics, the conversation carries the familiar PMHH rhythm: candid laughter, a little self-roasting, and the practical wisdom that comes from having been around the block more times than they're willing to count. It's not a tidy thematic episode — it's better than that. It's a Happy Hour catch-up that turns into real insight about project leadership, stakeholder psychology, career development, and the everyday challenges PMs face.

If you've ever struggled to explain your job, watched fear take over a meeting, or wondered what life might look like outside the corporate bubble, you'll find something in this episode that feels uncomfortably familiar — and maybe a little inspiring.

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