Why Execution Fails—And What We’re Missing
Founders are no strangers to pressure. There’s this constant current running underneath everything we do—the need to move fast, make it happen, and prove the vision. But the truth is, speed means nothing if your team is misaligned. The most dangerous risks are rarely technical—they’re relational. They’re the silent, invisible breakdowns that happen when no one names what needs to be said.
This is what Risk Up Front addresses with a clarity that made me nod through nearly every page. It’s not a book about adding more structure—it’s a book about having more courage. It gives language to something I’ve seen over and over again in founder rooms and team dynamics: when we don’t say the hard thing early, we end up paying for it later in confusion, tension, and misalignment that slows everything down.
Sometimes, in founder meetings or high-stakes client work, I’ll see someone go quiet at just the wrong moment. And I know exactly what’s happening—they’re weighing whether it’s worth naming the concern. Whether it will make them look difficult. Whether someone else will say it first. That’s the moment when leadership begins. Not with a decision, but with a willingness to name the risk out loud.
NOTE: RCY Labs has curated a list of 52 books for Founders (2025 Edition) who care about business profitability AND impact. Don't have time to read all 52 books? We've got you! We'll read them for you, and give you the summaries, audio casts, outlines, and frameworks to apply to your business ... all FREE in the Founders' Lab Community (on Slack). Join here.
The Real Problem Isn’t the Plan—It’s the People
One of the most freeing truths in this book is that most execution failures aren’t actually about execution—they’re about relationships. The tension between people. The absence of clarity. The unwillingness to ask questions that might feel inconvenient.
And here’s the thing: I’ve lived this. I’ve built with teams where everything was clicking technically, but something still felt off. We were saying yes, but we weren’t aligned. We were smiling on Zoom, but not totally clear on what we’d committed to. In those seasons, it wasn’t the lack of resources or strategy that slowed us down—it was the risks we didn’t say out loud.
I’ve come to believe that clarity is a gift we give our future selves. And when founders skip clarity in the name of efficiency, they create costly repair work down the line. What this book does beautifully is reframe truth-telling as a leadership skill—not a personality trait. It gives us a framework for building alignment on purpose.
Commitment #1: We Will Speak Up
Speaking up shouldn’t feel like an act of rebellion. But in a lot of fast-moving founder environments, it does.
One of the first things I notice in team dynamics—whether it’s with clients, community members, or inside my own team—is who feels safe enough to say, “I’m not sure that will work.” Or, “We might be missing something here.” The ones who raise concerns aren’t slowing us down—they’re saving us time. They’re protecting the mission.
What I love about Risk Up Front is how it encourages teams to ask a single question that changes the tone of everything: “What could go wrong?” Before the work begins. Before anyone is defensive. That question, asked with sincerity and safety, opens a door to real alignment.
In my world, I’ve seen the difference this makes. I remember a launch planning meeting where a junior team member hesitated, then finally said, “I don’t think this is doable in two weeks.” That one moment gave us the chance to recalibrate. She wasn’t being difficult. She was being honest. And that honesty protected the quality of our work.
Speaking up is a sign of commitment, not conflict. But leaders have to make that clear—early and often.
Commitment #2: We Will Support Each Other
Support is often misunderstood in founder culture. We think it means doing things for each other, or softening feedback to keep the peace. But the kind of support this book talks about is deeper—it’s support through clarity. Through presence. Through care that’s strong enough to tell the truth.
I’ve always believed that kindness and accountability aren’t opposites—they’re companions. The most meaningful relationships in my life, both personal and professional, are with people who will look me in the eye and say, “You’re capable of more than this.” Not to criticize me—but to remind me who I am and what I’m here to do.
I’ve said those words to founders I work with, too—especially when they’re hiding behind busyness or defaulting to old patterns. True support says, “I’ve got your back, and I’m going to challenge you to lead with intention.”
Inside our team, that’s looked like creating space for check-ins that go deeper than status updates. It’s asking, “What do you need from me to follow through on this?” It’s naming when we’re stretched too thin—and realigning instead of pretending.
Support is a decision. It’s showing up. And it’s believing in each other enough to say, “I see you, and I’m not going anywhere.”
Commitment #3: We Will Own the Result
I don’t know a single founder who hasn’t felt the weight of being the “catch-all.” The one circling back. The one filling in the gaps. The one quietly wondering, Why am I the only one carrying this?
That’s not a leadership problem—it’s a clarity problem.
In Risk Up Front, ownership isn’t just about assigning tasks. It’s about making real commitments. Agreements that are clear, visible, and alive. Ownership sounds like, “I’ve got this, and here’s when it will be done.” And just as importantly: “If that changes, I’ll say so.”
This commitment has shaped how I work with teams, especially in high-growth seasons. In any room where roles are evolving quickly, I’ve learned to ask, “Who’s owning this?” Not “Who’s helping?” Not “Who’s checking in?” But who is accountable for the result?
It’s a small distinction. But it changes everything.
I’ve worked with founders who suddenly felt like things were breaking down, only to realize nothing was actually broken—it was just never owned. When we shifted from vague intentions to named commitments, everything clicked back into place.
Ownership brings order. And in a startup, that kind of order is freedom.
Trust Isn’t a Feeling—It’s a System
What makes Risk Up Front such a powerful read is how it demystifies trust. It’s not something you hope for. It’s something you build, moment by moment, by creating spaces where people know they’re seen, heard, and expected to lead.
And when I think about the founders I admire most—those who lead with grace and grit—it’s not their charisma that stands out. It’s their clarity. It’s the way they protect trust like it’s part of the product. Because in a way, it is.
Clarity isn’t a tactical advantage. It’s a spiritual one. It says, “We matter enough to get this right.”
Final Thoughts: Say the Hard Thing First
Leadership isn’t about having all the answers. It’s about creating the kind of environment where the right questions can be asked.
You don’t need to be perfect to build something great. But you do need to be willing to name what’s real—early, clearly, and without apology. That’s the difference between leading with fear and leading with love.
If you’re building something that matters, remember this: You’re not just designing a product or a service. You’re designing a culture. One that invites truth. One that honors ownership. One that can handle the weight of real growth.
So before your next project kickoff, team meeting, or decision point, pause and ask:
What’s the risk no one’s saying out loud?
What commitment needs to be clarified?
Where can I lead with more truth—today?
Say the hard thing first. That’s how we lead with heart.
NOTE: RCY Labs has curated a list of 52 books for Founders (2025 Edition) who care about business profitability AND impact. Don't have time to read all 52 books? We've got you! We'll read them for you, and give you the summaries, audio casts, outlines, and frameworks to apply to your business ... all FREE in the Founders' Lab Community (on Slack). Join here
