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A former Army sniper introduced me to this concept. We were roommates, and one night over a beer he explained to me how he prepared. Not just the mechanics, but the art and craft that went into his trade. Reading the wind. Calculating distance. Controlling breathing. Working through every variable that stood between him and a successful outcome. Over and over. Until it wasn’t thinking anymore. It had become process. He told me that when he engaged, he wasn’t reacting. He had

You can't have offsite team meetings. My internal response was immediate: why not? I knew the value. My team was fully remote. Many were new. There was no local office. Getting people together for a few focused days of business planning, role alignment, and team building felt essential, not optional. Before I could argue further in my head, the answer came: financial. The cost per offsite multiplied by the number of teams produced an unacceptable number. Which made complete s

You know the type of call it will be from the first five words. "Heeyyy... how are you doing..." And before they finish the sentence, you already know what's coming. A withdrawal. The Bank of Trust is an invisible balance sheet we all carry. It tracks the investments we've made in each other; the moments we showed up without an agenda, freely recognized someone's effort, or simply made someone's job easier without being asked. And when the balance is zero, everyone feels it.

Arguably, one of the hardest roles I ever had was my first front-line management job. There were all kinds of challenges. What kind of leader would I be? How do I move from IC to manager? How do I coach effectively? And most importantly: where do I spend my time? As I progressed into VP and CRO roles, my teams became more experienced. They had already proven they could operate at a high level. Front-line management is different. It's the wild west. Who is leaning in? Who is p

Most revenue organizations are built to win deals. Very few are built to keep them. When I first became a CRO, I thought I understood the full revenue picture. I was strong on the numbers. Experienced in sales process and leadership. I had even started my own business. I was wrong. Or more accurately, incomplete. It wasn't until I went through Revenue Architecture training from Winning by Design that I saw what I was missing. Quick note: I don't work for them or consult for t

Failure gets your attention. Success changes behavior. The habits that created success are often the first things to fade. The extra outreach slows. The additional questions go unasked. Preparation becomes assumption. Nothing breaks all at once. It drifts. You put in the work. You build the habits. You learn the craft. You hit your number. And without realizing it, something changes. Not dramatically. Just slightly. Because winning is not an outcome. It is a process. And the

Math. It's important. It's the universal language of business and the fundamental principle plans should be built on. Behind every good plan is something many companies underestimate: a strong Revenue Operations leader. I had the opportunity to work with Thor (The House of Revenue), an exceptional RevOps leader. It was like when Billy Beane met Peter Brand in Moneyball. If you haven't seen it, search "a simple question that changed baseball forever." RevOps connects the entir

A question I've been asked many times over the years is simple. Why do revenue plans fail? Not occasionally. Not unexpectedly. But predictably. Most revenue plans don't fail because of strategy. They fail because of math and execution. A target gets set. The plan gets built to support the target. But the mechanics of how revenue is actually produced are never reconciled. Revenue isn't created by ambition. It's created by a system. That system includes sales capacity, ramp tim

There is no proprietary framework here. No methodology I'm trying to sell. Over the next few weeks I'm going to share a series called "Questions I've Been Asked." These are lessons collected over a long career. Some I learned the hard way. Others came from people who had already made the mistakes and were generous enough to share what they learned. I've been fortunate to sit in a lot of different seats: in boardrooms, in the candidate chair, across the table as a hiring manag

The first person a sales rep lies to is themselves. Not intentionally. Not maliciously. But it happens all the time. A quick note on tone: not a good thing or a bad thing, just a thing. And that thing has real financial implications. But this issue doesn't sit with reps exclusively. It's an output of a system and leadership that has allowed it to go unchallenged. I worked for a sales leader who helped shape my career. His concept: if one rep was struggling with a deal, chance

Every candidate walks into an interview with their hero story ready. Those stories are prepared, polished, and practiced. They tell you something. But they don't tell you everything. So at some point in most interviews I conduct, I ask a different question: tell me about a time you failed. Not a challenge you overcame. A genuine failure. The room changes when I ask it. The first type I call fake failing. It sounds like self-reflection but isn't. Watch for it. It's like someon

Some of the most successful plans I've been part of were not the most detailed ones. And sadly, a significant number of the most complex ones never got off the ground. A plan nobody can execute isn't a plan. It's a document. So how to overcome this? How do you filter out the noise from the critical? Most times, the hardest question is: where do you begin? I use five stage-zero questions before any planning work begins. Not in the middle of the process. Before it. An implement

Most teams build a revenue plan and then ask whether it's achievable. The better question is whether it's achievable before you build it. That requires running the model in reverse. Start with the target. Then work backwards through every layer of the system until you either find support for the number or find where it breaks. The first place I go is time, value, and conversion: the conversion percentage from stage to stage, how long a deal spends in each stage, and how many