It was Monday morning, April 13. I was working from the Middle East, where my wife Jan and I were leading True You retreats. The time difference meant my workday ran late into the night while the team back home moved through their morning. I was tired. I was three weeks into international travel. And I was trying to keep an eye on a 90-day cash flow forecast that mattered a lot, because the national expansion of the Leadership Accelerator was inside it.
The forecast wasn’t moving.
Matthew handles our finance work. He’s a strong operator. He’s also my son-in-law, which is its own quiet stake on every email I send him. The work relationship is real; the family relationship more so. And on that Monday morning, looking at a budget that wasn’t progressing the way I wanted it to progress, my first instinct was to fire off a short email with a clear tone. Something like: Matthew, what the heck is going on with the budget?
I didn’t type it. But I almost did.
What stopped me wasn’t virtue. It wasn’t a moment of grace. It was a calendar entry. I was finalizing the slides for a teaching session I was leading the very next week: a session for thirty Orthodox priests on a tool we call the Upstream Audit™. The whole point of the tool is to interrupt exactly the email I was about to send.
So I closed the draft. I stood up. I walked away from the laptop and made another cup of coffee in a borrowed apartment kitchen at an hour that should have been quiet but wasn’t. And when I came back, I wrote a different email.
Matthew, checking in on some Edens View stuff. Here are some key priorities. What is the budget status with TeAira? How soon do you expect to complete a draft budget? What are your thoughts on Syft vs. Fathom? I’d like to get this up and running soon. A reminder: we moved receipt filing to Google Drive…
Five priorities. Bulleted. Hyperlinks to the relevant documents. No tone. No frustration. Just clarity.
His reply came the next morning. And it was the kind of reply that turns the mirror around.
He’d had the budget ready for a week. He didn’t have the 2026 numbers because I’d never sent them. He’d been waiting on Syft login info because I’d never sent that either. He was confused about the receipts workflow because I’d changed the system and not communicated the change clearly. Three separate upstream gaps in one short message. And then his closing line, which I read twice and then sat with for longer than I wanted to:
Sorry to be behind on things, but I’ve been a bit lost with the changes.
He apologized. To me. For being lost in the system I hadn’t built clearly.
That’s the moment I want you to sit in for a second. Because if I’d sent the first email, the one with the tone, Matthew would have apologized anyway. He would have absorbed the weight of my frustration, internalized it as his failure to keep up, and we’d have spent the next two weeks navigating the residue of an email I shouldn’t have sent. The work would have gotten done. But something else, something quieter, would have taken a hit.
What would have taken a hit was trust. The kind of trust a son-in-law extends to a father-in-law when he agrees to do finance work for his business. The kind of trust that doesn’t replenish itself just because the budget eventually balanced.
I sent a meeting request next. Then, 43 minutes later, I sent a structured response that owned the system gaps directly. Here’s the budget number context. Here’s the Syft access. Here’s the receipts workflow, step by step, with the actual sequence written out. The repair email took longer to write than the original frustration email would have. It also healed instead of harmed.
The whole exchange was resolved cleanly. Matthew cleared the receipts on April 23; ten days after the original send. Ten days, because the system gaps were real and clearing them took time. That’s the cost of upstream failures. Quietly. Without fanfare.
Why I Almost Sent the Wrong Email
So much of my coaching is about helping leaders communicate clearly. But that’s never the ultimate goal. Clear communication is the bridge to building teams where people don’t have to apologize for being lost in systems we never made clear.
God has the habit of reminding me one more time before I teach anything. The reminder this time came in the form of a tool I’d been preparing all week to teach to thirty priests, and that I almost violated before I could deliver it. The tool is called the Upstream Audit™. And it works like this.
When a team member appears to be underperforming, most leaders do what I almost did. We look at the person. We get frustrated. We escalate. We type the email. The Upstream Audit™ interrupts that move by asking a single diagnostic question first:
How much of this is a leadership issue, how much is a systems issue, and how much is actually a performance issue?
The question matters because most performance problems aren’t people problems. They’re upstream problems. And there are three buckets to work through, in this exact order, before any of us has earned the right to a performance conversation.
Bucket 1: Leadership. Have you communicated clearly what winning looks like in this role? Has the person been given the information, the context, and the direction they need to deliver? In my email, the leadership gap was the budget numbers. Matthew was waiting for numbers I’d never sent him. That’s not a Matthew problem. That’s a David problem.
Bucket 2: Systems. Does the person have the tools, the access, the visibility, and the workflow they need to complete the task? In my email, the systems gap was the Syft login. Matthew couldn’t run the analytics because the access never reached him. He was being asked to deliver results in a system he literally couldn’t enter. The receipts workflow was the same kind of gap; I’d changed the system without making the change visible to the person executing it.
Bucket 3: Performance. Only after the first two buckets are clean does the third one apply. Has the person been given clarity? Yes. Have they been given systems? Yes. And is the pattern of falling short still happening? Then, and only then, has the leader earned the right to a performance conversation.
Notice what happens when you run those three buckets in order. The first two are about me. They require me to evaluate my own communication, my own systems, my own clarity, before I evaluate the person on the other end of the email. That’s not soft. It’s accurate. And it’s why most performance frustrations dissolve before bucket three is ever reached.
What if the email you’re tempted to send right now is actually a leadership audit you haven’t run on yourself yet?
What if the team member you’re frustrated with is operating in a system you built and forgot to maintain?
What if the thirty seconds between instinct and send is the most important leadership move you’ll make this week?
I almost didn’t make that move on April 13. I’ve coached dozens of leaders through this exact moment. They come to me convinced their options are binary: coach this person up, or cut this person loose. The Upstream Audit™ exists because the binary itself is the problem. And on Monday morning in the Middle East, I almost violated my own framework. That’s why we keep teaching this; not because the lesson is new, but because the temptation is constant. And that’s why we don’t just deliver this tool. We make leaders go through it before they teach it.
If you’ve ever stared at a draft email and felt the pull to send the version with tone, the Leader Edition of the Upstream Audit™ was built for that thirty-second pause.
Three buckets. Diagnostic questions for each.