We’ve all managed one. That brilliant, meticulous, and incredibly dedicated team member who… just… can’t… finish.
You see them agonizing over an email, spending days on a “simple” report, or freezing in meetings. You know they’re working, but they’ve become a bottleneck. The anxiety is palpable. And if you’re like me, your first instinct is a mix of empathy and pure frustration.
This isn’t a problem of laziness or a lack of skill. It’s often a communication barrier built by a powerful, invisible force: overthinking.
I want to share a real-world case study from my time as a manager, focusing on an employee I’ll call “Alex.” More importantly, I want to share the framework I used to finally break through—but only after I got it completely wrong first.
The Context & My Mistake (The “Trust” Builder)
Alex was one of the brightest analysts on my team. His research was flawless. The problem? He treated a routine weekly update with the same life-or-death scrutiny as a year-end audit. His “analysis paralysis” meant other departments were constantly waiting, and my team’s workflow was stalling.
And I’ll be blunt: I failed him at first.
For weeks, I avoided the conversation. I was busy, and I told myself, “He’s just being thorough.” That avoidance was my first mistake.
My second mistake was when I finally did say something. It was a disaster. Under pressure from a director, I pulled Alex aside and said something to the effect of: “Alex, what is the hold-up? I’m getting pressure. We just need to get this report out the door. Can you please just be faster?”
I watched him physically deflate. His face tightened, he gave a one-word “okay,” and the wall between us shot up. I had taken his core anxiety—a fear of getting it wrong—and confirmed it. I’d focused on the symptom (the delay) and completely ignored the cause (his thought process). The barrier was now higher than ever.
The Framework (The “Expertise”)
I knew my “just do it” approach had failed. I had to try something else. I needed to understand how he was thinking, not just what he was producing.
I decided to use a mental model called “The Ladder of Inference.”
Developed by organizational psychologist Chris Argyris and popularised at Harvard Business Review, the ladder shows how we mentally “climb” from observable data to a final action.
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We observe Data/Facts.
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We select “Our” Data.
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We add Meanings/Interpretations.
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We make Assumptions.
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We draw Conclusions.
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We adopt Beliefs.
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We take Actions.
Overthinkers don’t just climb this ladder; they get stuck on a rung, re-litigating every fact. Or, they make a “reflexive loop”—jumping from a single piece of data (e.g., one typo) to a massive, limiting belief (e.g., “I am a failure and everyone will know it”).
My goal was no longer to tell Alex to be faster. It was to invite him to walk me down his ladder.
The Conversation (The “Experience” & “Helpful” Core)
I scheduled a new meeting, but this time I prepared. I started by apologising for our last interaction. Then, I changed the script entirely.
❌ The Way I Handled It First (Low Trust):
Me: “Alex, your report is late again. I’m getting pressure from the director. What’s the problem now?”
Alex: (Defensive) “I’m just checking the final numbers. I want to be sure.”
Me: “It’s a weekly update, not an audit. We just need to be faster. I need you to just get it done.”
Result: Alex feels untrusted, misunderstood, and more anxious. The barrier is reinforced.
✅ The Way I Handled It Using the Framework (High Trust):
Me: “Alex, thanks for meeting. I wanted to try a different way to talk about the weekly report. My goal isn’t to rush you; it’s to understand your process, because I know how much care you put into it.”
Alex: (Wary) “…Okay.”
Me: “When you start the report, you gather all the raw data. That’s the first step, right?” (This is Rung 1: Data).
Alex: “Right. I pull the sales, traffic, and support logs.”
Me: “Great. Walk me through what happens next. What do you look for in that data?” (This is Rung 2: Selecting Data).
Alex: “Well, I look for outliers. For example, this week, sales in one region were down 2%.”
Me: “Okay. And what meaning do you attach to that 2% drop?” (This is Rung 3: Adding Meaning).
Alex: “That’s the part… I see that, and I think, ‘Something’s wrong.’ What if the data is corrupt? What if a server failed? What if I present this and the director asks why and I don’t know?”
Me: “So your assumption is that if you don’t have an answer for every possible question stemming from that one data point, you can’t release the report?” (This is Rung 4: Assumptions).
Alex: (Pauses) “…Yes. I guess that’s it. I get stuck trying to find the ‘why’ for every single number, in case I’m asked.”
Result: This was the breakthrough. We had found his “reflexive loop.” He was jumping from “a 2% drop” (Data) to “I will be exposed as a fraud” (Belief). The action he took was to over-analyse to protect himself.
The Outcome & The Lesson
This conversation did not “cure” Alex of overthinking. That’s not a realistic outcome.
But it shattered the communication barrier. For the first time, Alex felt seen, not just managed. We moved the problem from “Alex is slow” to “Alex’s process gets stuck at Rung 4.”
The realistic outcome was that we could now co-create a solution. We agreed on a new rule: “First drafts are for discussion, not perfection.” We set up a 15-minute check-in where he could bring me his “80% draft” and his “ladder” (his list of worries). We could then decide together which data points were actually worth a deep dive.
My lesson was profound. I had been trying to manage a symptom (lateness) when I needed to understand a story (his mental ladder).
💡 For Visual Thinkers: After our chat, I sent a follow-up email. It wasn’t a wall of text. It was a simple, two-column list: “Our Shared Ladder” (what we need for the report) vs. “The ‘Parking Lot’ Ladder” (questions to explore after the report is sent). For visual thinkers and those with dyslexia, seeing the structure of the problem is everything. It moves the anxiety from a tangled, internal feeling to an external, organised, and solvable process.
🟧 Try This Today
You can’t fix an overthinker. But you can build a bridge. This week, find a moment with that person and ask one simple, non-judgmental question:
“Can you walk me through your thought process on that?”
Don’t interrupt. Don’t solve. Just listen. Your only goal is to find the rung on the ladder where they’re getting stuck. That’s the first step.
**By Stephen Connell, BSc PGCE (Communication Trainer)**
**Updated: 11 November 2025**
