Every two weeks, the Leadership Audit series publishes one diagnostic question for leaders. Not a framework. Not a quiz. One question worth sitting with — and one action to take this week.
This week’s question:
Do you have a checkpoint between your team’s work and what goes to clients or stakeholders?
Why this question matters
Most leaders who lose a client or damage a stakeholder relationship don’t lose them because someone on their team wasn’t capable. They lose them because something left the building before it was ready, and nobody had defined the moment when someone was supposed to stop and ask: ” Are we sure about this?
That moment is a checkpoint. And in most teams, it doesn’t exist in any formal way. Work gets done, gets sent, and the first real review happens on the receiving end, by the person you most needed to impress.
The absence of a checkpoint isn’t usually a sign of carelessness. It’s a sign that the team was built around trust and capability rather than process. Which sounds like a good thing. And often it is, until something complex goes wrong in a way that a second set of eyes would have caught.
What happened when I didn’t have one
We had a difficult client. Distrustful, hard to communicate with, and resistant to our process, no matter how many times we walked them through it. After months of work, we had made enough headway that I felt comfortable handing the project to someone on my team. She was capable. I trusted her. The relationship felt stable enough. I stepped back.
I didn’t build a checkpoint into the handoff.
The work was complex — the data was genuinely hard to measure and easy to misread. My team member sometimes hesitated to raise questions when they were uncertain, and I hadn’t made it explicit enough that asking questions wasn’t just okay but expected. So things moved forward without a second set of eyes. Without an internal moment when someone said, “Let’s look at this together before it goes out.”
When the work landed with the client, it didn’t land well.
Looking back, it wasn’t a capability problem. My team member was good at her job. It wasn’t a trust problem either — I trusted her completely, and that trust was warranted. It was a systems problem. Nobody had defined the moment when the work paused for review before it moved forward. That moment didn’t exist because I had never built it.
The cost wasn’t just the client relationship. It was the impact on my team member, who had done her best work in the absence of the structure, that would have made it even better. That’s the part that stayed with me longest.
What a checkpoint actually looks like
A checkpoint doesn’t have to be complicated or time-consuming. It doesn’t require a formal review process or a committee. It just has to be a defined, consistent moment — agreed in advance — when someone other than the person who did the work reviews it before it goes to the client or stakeholder.
In practice, it might look like any of these:
A standing agreement that any deliverable going to a specific client gets one internal review before it’s sent — even a 15-minute read-through.
A simple question built into your workflow: before this goes out, who has looked at it besides the person who created it?
A norm on your team is that complex or high-stakes work gets a second set of eyes by default, not an exception.
The specifics matter less than the consistency. A checkpoint that sometimes happens is not really a checkpoint. It’s a hope.
The question underneath the question
There’s a deeper question inside this one that’s worth sitting with.
When something goes wrong on your team — when work lands badly, when a client is frustrated, when a deadline is missed — what’s your first instinct? Is it to figure out who dropped the ball, or to figure out what process would have prevented it?
Both questions can be useful. But the second one builds something. The first one just assigns blame and moves on, leaving the same gap in place for the next time.
A checkpoint is a small structural commitment that says: We are not going to rely entirely on individual capability and hope. We are going to build a moment into the work where someone stops and looks.
That moment costs almost nothing to create. Its absence can cost significantly more.
The action this week
Think about the work that leaves your team most regularly: reports, proposals, client communications, data, and presentations. Pick one category. Ask yourself: before this goes out, who looks at it besides the person who made it?
If the answer is nobody, or it depends, or I usually do but not always — that’s where to start.
Define the checkpoint. Name it explicitly to your team. Make it a default rather than an exception.
One structured moment. Built in advance. Every time.