From Episode 25 of Hardcore and At Ease hosted by Shelly Rood. Parts of her interview with Chaplain Brian Webb served as the backbone of this article on Why Top Leaders Fail Under Pressure (And The Proven Strategy That Works).
“I ended up in inpatient treatment for trauma exposure and over just overdoing. A lot of that was my own fault for just taking it too far for too long and just thinking there was something noble about running myself into the ground.”
That’s Chaplain Brian Webb—a man who has walked alongside people through their darkest moments for over two decades. He’s stood at doorsteps delivering devastating news 79 times. He’s been the calm voice in 40+ crisis interventions. Today, he leads Michigan’s Walking with Warriors program, where he’s building something remarkable: a team of 50 people doing sacred, impossible work—sustainably. If someone who has carried this much weight can hit the wall, what does that tell us about sustainable leadership?
As an ambitious person, you may feel that you’re carrying impossible weight. Your team depends on you to stay grounded when everything is falling apart. But the very traits that make you an exceptional leader—your drive, your standards, your refusal to quit—are the same traits that will destroy you if you don’t learn to lead under pressure differently.
This isn’t theory. Webb’s insights come from standing in spaces most of us will never face: midnight door knocks to tell mothers their child won’t be coming home, crisis interventions with loaded weapons involved, leading teams through trauma that would break most people. What he’s learned about why leaders fail under pressure and the proven strategy that prevents it isn’t just applicable to extreme situations—it’s essential for anyone leading teams through high-stakes uncertainty.
Why Top Leaders Fail Under Pressure: The Noble Sacrifice Trap
“The whole world was burning down and by God I was going to put out the fire.”
Webb describes the exact moment he realized he was failing: “I kinda set aside everything for the mission. I had forsaken everything. I was running headstrong into fire. The whole world was burning down and by God I was going to put out the fire.”
Sound familiar? That’s the trap top leaders fall into. We believe our value is in our sacrifice. We wear exhaustion like a badge of honor. We convince ourselves that if we’re not running ourselves into the ground, we’re not working hard enough.
Webb calls this out directly: “There was some foolishness in that on my part. There is some of that little bit in me that says nobody can do it quite the way I do it.”
There it is. The core belief that causes top leaders to fail under pressure: the conviction that you’re the only one who can do it right, so you must do it all.
This belief system creates a cascade of failures:
- You become the bottleneck for every decision
- Your team learns learned helplessness (why try when you’ll just redo it?)
- You have no capacity left for the strategic thinking that actually moves the mission forward
- Eventually, your body and mind force the issue by breaking down entirely
Webb spent years in this pattern—knocking on doors “three and four and five times a night” during wartime, becoming “just a machine just doing this so often and running so hard.” He caught himself checking out mentally while still going through the motions. “Eventually you’ll realize that. You’ll be like, oh, like that’s just not working.”
But by the time most leaders realize it’s not working, they’re already in crisis mode. The question is: what’s the proven strategy that actually works?
The Proven Strategy That Works: Three Principles From 79 Impossible Conversations
Over two decades, Webb has developed a methodology for staying grounded under extreme pressure. It’s built on three core principles that work whether you’re facing a suicide intervention or a quarterly budget crisis.
Principle 1: Validation Before Solutions
Picture this scenario from the podcast: It’s 11:30 PM. A young soldier sits in a forward operating post with a loaded weapon, ready to end her life. She gave birth three weeks ago. Her mother won’t return calls. The crisis team has been trying for an hour to get the weapon away from her. Nothing is working.
Webb walks in and says something disarmingly simple: “I know it’s been a really crappy day. I know it’s been hot. I know right now all you care about is your baby, and I get it—you just gave birth. We’re going to take care of this. But first, I need you to give me that firearm.”
And she does.
What just happened? Webb explains: “You start the conversation by validating the situation they’re in and just recognizing that they’re really struggling and that it’s okay to struggle. I’m not minimizing you or criticizing you as a person because you’re struggling.”
This is why top leaders fail under pressure:
They skip validation and go straight to solutions. When your team member is drowning, they don’t need your five-point action plan first. They need to know you see them, you understand the weight they’re carrying, and it’s okay that this is hard.
Webb learned through 40+ suicide interventions: “I didn’t say ‘no, you don’t really want to do that,’ because really he does want to do that. I just said, ‘okay, so tell me what’s going on.'”
How to Apply Validation When Leading Under Pressure:
- When someone is struggling, your first words should acknowledge their reality: “I can see this is really hard right now.”
- Name the specific pressure they’re under: “You’re managing the product launch while two team members are out—that’s a massive load.”
- Give explicit permission for imperfection: “It’s okay that this is difficult. This would be difficult for anyone.”
- Only then ask: “What would be most helpful right now?”
This isn’t soft leadership. This is strategic leadership. People who feel seen will tell you the truth about what’s actually happening. People who feel judged will tell you what you want to hear—and you’ll make decisions based on incomplete information.
One important note on validation – it has to be honest and meaningful. Phrases like, “It sounds like you’ve got a lot going on,” can come off as placating and will likely send the conversation in the opposite direction.
Principle 2: Presence Over Performance
Webb shares a concept that defines his entire career: the ministry of presence. It’s the discipline of just being there—fully there—when everything in you wants to fix, solve, or prove your value.
His dad taught him a principle that shaped everything: “You don’t get the right to speak. You earn the right to speak.”
Webb describes sitting in Michigan Department of Health and Human Services leadership meetings for months without saying one word. He listened, he observed, and he was present. Then one day, someone mentioned veterans and asked what he thought. “Obviously I’m the subject matter expert, and so that was taken with authority because I’d been sitting in meeting after meeting for months without saying one word.”
Top leaders fail under pressure because they’re performing, not present
We talk to demonstrate value, or to offer solutions to prove competence. We fill silence because we’re uncomfortable with it. But presence—real presence—requires us to surrender control and trust that our value isn’t in what we do, but in who we are when we show up.
This connects directly to the SELF phase of the Hardcore and At Ease Framework (the yellow and red center rings of the target). Before you can serve OTHERS, you must be grounded in SELF—your authentic foundation, your tactical center. When you’re trying to lead from exhaustion, from proving yourself, from constant doing—you’re not present. You’re performing. And your team can tell the difference.
How to Practice Presence Under Pressure
- In your next one-on-one, practice listening without planning your response
- When someone shares a struggle, count to three before speaking. Let the silence hold.
- Replace “How can I help?” with “I’m here. What do you need right now?”
- Attend one difficult conversation this week with the goal of simply being there, not solving
Webb offers this powerful example: “If I had one encouragement to tell people, go to a funeral home, go up to the grieving family and just hug them and tell them that you love them and that you’ll be here. You can even say, ‘I know there’s nothing I can say. I’ll tell you what, I will be in the back of the room if you need me, and I will be here all evening or all day.’ That’s presence.”
Principle 3: Recovery Before Leadership
“If you have a peer support specialist who is still in recovery, they’re both still in the battle, not beyond the battle.”
One of Webb’s most critical distinctions addresses why some leaders can help others navigate pressure while others just add to the chaos. He works with peer support specialists—veterans helping other veterans through mental health challenges. And he’s noticed something crucial: there’s a massive difference between someone who is “in recovery” and someone who is “recovered.”
“If you have a peer support specialist who is still in recovery, they’re both still in the battle, not beyond the battle. It’s kind of like I can get my battle buddy in war, and I’ve got his back. I’m back to back with him and we’re both fighting, but we’re both under the same fire. All I can do is make sure he stays alive and make sure I can stay alive. We really can’t help each other in any other capacity but in that moment.”
But someone who has moved to “recovered”? “They now have skills and abilities and growth that can really bring that person much quicker through that process and help them avoid the barriers, the landmines along the way.”
This is the core reason top leaders fail under pressure: You can’t give what you don’t have.
If you’re barely holding it together, you’re in survival mode—not leadership mode. Your team needs you recovered, not recovering.
Webb’s 2018 breakdown taught him this the hard way. He wasn’t just tired—he was depleted to the point where he couldn’t effectively lead anyone, including himself. “There’s nothing noble about that,” he reflects.
But here’s what’s different about recovered leaders: They’ve done the hard work to heal, to set boundaries, to build support systems. They’re not just surviving alongside their teams; they’re actually leading through the pressure because they have capacity to give.
This is the OVER phase of the Hardcore and At Ease Framework (the light and dark blue middle rings). You can’t build resourceful action or generate momentum when you’re depleted. The transition from SELF to OVER requires you to move from “I can do this alone” to “I need systems and people to sustain this.”
How to Move from Recovering to Recovered:
- Identify one area where you’re “white-knuckling it”—barely holding on but refusing to change
- Ask: “What support system would someone recovered have in place here?”
- Build that system before you need it (coaching, peer support, accountability, boundaries)
- Give yourself permission to prioritize your recovery as mission-critical work, not optional self-care
The Three Core Responsibilities That Prevent Failure Under Pressure
Webb describes the three core responsibilities of a chaplain: nurture the living, care for the wounded, honor the dead. Then he makes a profound connection: “There’s really no difference between that and all of life. We all do those three things, or we should be doing those three things.”
When you examine why top leaders fail under pressure, it almost always traces back to neglecting one or more of these three responsibilities:
Nurture the living:
Top leaders often only pay attention when something breaks. They focus all their energy on struggling team members and ignore high-performers. But high-performers under pressure need nurturing too—they just won’t ask for it. When you fail to nurture people who are succeeding, you miss early warning signs that they’re starting to struggle.
Care for the wounded:
When someone is hurt (professionally, personally, emotionally), failing leaders expect them to perform through it. “Just push through” becomes the default response. But wounds that aren’t properly tended to don’t heal—they fester. Webb notes how poorly we handle this: “When people are grieving, they tend to lose people after a couple months. Thirty days out from a death, everybody’s gone and they’re on their own. And they’re not done grieving yet.”
Honor the dead:
This isn’t just literal. It’s about honoring what’s ended—the failed project, the person who left, the strategy that didn’t work. Leaders who fail under pressure rush past endings. They want to move on quickly because they’re uncomfortable sitting with loss. But you can’t build something new until you properly honor what ended.
This is the OTHERS phase of the Hardcore and At Ease Framework (the black and white outer rings). When you expect excellence from your team (ring 5) and trust the process of growth and transformation (ring 6), you must honor all three: nurturing, caring, and honoring. You can’t just demand performance—you must tend to the full human experience of your team.
How to Apply These Responsibilities Under Pressure:
- Nurture: Schedule time with your highest performers this week, not just struggling team members
- Care: When someone is wounded, ask “What do you need to heal?” before “When can you return?”
- Honor: Create closure rituals for endings—team debriefs, farewell processes, project retrospectives
The Hard Truth About Sustainable Excellence
“Are we doing the right things, and are we doing them right?”
Throughout the conversation, Webb wrestles with his own relationship to work. He describes himself as someone who “just puts my head down and works hard at whatever God’s given me to do.” He quotes General Vadnais’s question that shaped him: “Every morning I get up and I ask myself: Are we doing the right things and are we doing them right?”
But Webb also recognizes the trap: “I’ve driven myself into the ground to where I ended up in a lot of trouble, just physically and mentally where I just ran myself till I was just drained. That’s a mistake.”
The difference between working hard and working yourself to death
Here’s the tension every top leader faces: Hard work is essential. Excellence demands effort. But there’s a difference between working hard and working yourself to death.
Webb’s proven strategy? Build a team that shares the load. “This team makes my job really fun. I feel like I got a retirement gig. I’m working hard, but I don’t feel like this is labor. I feel like this is joy. There’s happiness and growth and potential.”
That’s what Others Over Self® actually means—not that you sacrifice yourself endlessly, but that you build systems where the pursuit of excellence serves something bigger than your individual capacity. When you try to do it all alone, you fail under pressure. When you build collaborative systems and empower others, you create sustainable excellence.
Webb describes it perfectly: “I put the train on a track in 2016 and gave it a push. The team is what fuels it and keeps it running down the track. My job is to keep putting enough track in front of it so it doesn’t derail and make sure it doesn’t go too fast around the curves. The team is the engine that makes this thing run.”
How to Build Sustainable Excellence:
- Identify what only you can do vs. what others could do with training
- Invest 20% of your time developing your team’s capabilities
- Create systems that work when you’re not there
- Measure success by team capacity, not personal output
What You Can Do Today
Webb’s wisdom comes from standing in spaces most of us will never face. But the principles that prevent failure under pressure translate directly to your leadership:
Immediate Actions:
- Practice validation in your next difficult conversation. Before solving, say “I can see this is really hard.”
- Earn the right to speak by listening more in your next meeting. Count how many times others speak vs. you.
- Assess your recovery status. Are you in recovery or recovered? What one support system would move you closer to recovered?
- Apply the three responsibilities: Who on your team needs nurturing? Caring? What ending needs honoring?
- Examine your workload: What are you doing that only you can do vs. what you’re doing because you haven’t empowered others?
The goal isn’t to become a chaplain. The goal is to learn from someone who’s mastered leading under extreme pressure—and apply those principles to your leadership, your team, your life.
Because here’s the truth: The pressure isn’t going away. The stakes won’t decrease. The crises won’t stop. The question is: will you learn the proven strategy that prevents failure under pressure, or will you keep running until you break?
Get the Gear
The Nazarene by Sholem Asch – The book that shaped Shelly’s understanding of faith and brought her to where she is today. Out of print but available on Amazon. If you’re trying to discover faith in a positive future when all you see is destruction around you, this novel will meet you there. Find it on Amazon
Walking with Warriors Program – Connect with Chaplain Brian Webb and learn more about the veteran navigator program serving military families: Michigan.gov/MDHHS
Hardcore and At Ease Framework – Learn more about the T.A.R.G.E.T. methodology and Others Over Self® philosophy at OthersOverSelf.com
Episode Resources:
- 📊 My Business Report: https://hardcore-and-at-ease.captivate.fm/biz-report
- 🎯 StoryBrand.ai: https://hardcore-and-at-ease.captivate.fm/storybrand-ai
- 📚 Business Made Simple: https://hardcore-and-at-ease.captivate.fm/bms
Listen to Episode 25: Chaplain Brian Webb on Gratitude and Grit
This article only scratches the surface of Webb’s profound insights on leading under pressure without breaking. In the full episode, you’ll hear:
- The exact words that convinced a soldier to hand over a loaded weapon in a crisis situation
- How Webb went from being terrified of public speaking to conducting 79 casualty notifications
- Why territorialism is “self-defeating” and how collaboration saved his program
- The moment Webb realized he was becoming a machine and what he did about it
- How to build a team that does sacred, impossible work without destroying themselves
Listen or Watch Episode 25: Apple Podcasts | Spotify | YouTube
Subscribe to Hardcore and At Ease for weekly conversations with leaders who’ve figured out how to keep their edge without going over the edge.
Join the conversation: Share this article and tag @OthersOverSelf with #HardcoreAndAtEase. What’s the biggest pressure you’re facing right now as a leader?
