I thought I was coaching the engineer. I was coaching myself.
How trying to fix someone else's communication gap exposed my own.
I handed my engineer his first client-facing role last month.
And in the first call the client asks multiple questions for which he didn’t have an answer.
UH oh. I felt my stomach drop. I hate leaving meetings where my team isn’t creating clarity.
Look, before you jump to any conclusions 😅 - he’s really sharp and I love his enthusiasm. If he’s reading this… know that I enjoy every minute working with him 😎
So what happened?
A bit of context: our client runs a cloud pipeline that produces metrics for their product team. Every week, they need to know whether the infrastructure can deliver those numbers on time. The questions that they ask are simple:
How much time does the car engine need to warm up? (how fast does the cluster provision compute when you need it?)
How quick does the car go from 0 to 60 km/h? And from 60 to 90 km/h? (what is the compute provisioning distribution in time?)
His job was to analyze the infrastructure, measure its characteristics, and explain what it means for the client’s roadmap.
After the call I sat down with him to debrief.
I started explaining that the client actually needed to know when does the engine start and how quick the car gets to 90 km/h. Not a technical summary of how the engine was built, but a clear picture of what it can do - the cloud system’s capability to provision compute within a given time window, the distribution of that latency, and what that means for product inclusion decisions.
I got about two sentences in and stopped. I could feel what good looked like.
BUT - I suddenly felt my mind was blanking on me. I was struggling with saying it in a way that can be CLEARLY easily understood. Like knowing that you have to cross the river but you’re missing the bridge.
Recognizing a communication failure is not the same skill as naming it.
I’ve watched engineers give updates that answer a different question than the one that was asked. I’ve seen technically correct dashboards that leave the viewer with no idea what to do next.
Being able to describe it with enough precision that someone else can avoid it - that’s a different competency.
But I just called it a communication failure - whose was it, though?
Let’s take a look again - the engineer needed to produce:
A view of the infrastructure’s capability to provision compute within a given time window - the distribution of it. How long does it take to spin up a given amount of VMs?
What does the variance look like? What does that mean for the product team’s deadline commitments?
What I described: the output I wanted.
What he heard: what to put in the report.
But what the client needed: a frame for making a decision.
Do you see what’s happening?
I’m completely failing to underline how his works helps the client make the decision.
So I decided to do something about this.
I recorded my last 1:1 with my engineer and I ran the transcription through an agent I configured in Claude Code. It reads the transcript against a communication skill rubric:
clarity of recommendation - does the listener know what to do after this call;
the ratio of questions asked to questions resolved - am I leaving open loops;
whether technical detail is anchored to a decision the listener actually faces.
The agent surfaces I’m making the other person work too hard to extract the point.
First report flagged something I hadn’t expected: I state conclusions without anchoring them in what the listener already knows.
That’s exactly what happened in the coaching conversation. I described good communication from inside my own mental model - without checking what frame the engineer was working from.
I gave him a destination without a map.
This isn’t the only gamechanger… the agent books a 15-minute block - dad life means I’m strapped for time these days 😅 - in my calendar each week to practice the specific skill it flags.
Also: it reassesses on the next call and tracks whether the pattern is changing.
On Thursday, I will post the Markdown files for the agent and how to configure it with the videocall transcription notes as well as how to integrate it with the calendar.
See you then!
PS. On the weekend I took part in a local race and ran up the local mountain Uetliberg in under 40 minutes. Really proud of that 😎
