How to Use AI to Make Behavioural Change Actually Stick

Your organization spent $50,000 on executive coaching this year. When finance asks what you got for it, what do you tell them? “Sarah feels more confident”? “The team says good things about their sessions”?

That’s not measurement. That’s anecdote.

But here’s the problem: the usual measurement approaches are worse than useless. Satisfaction surveys tell you people enjoyed the sessions, not whether they changed. Quarterly 360s come too late to catch what’s actually happening. And trying to tie coaching to business outcomes is mostly fantasy - you can’t isolate coaching’s impact from the ten other things that changed in the same quarter.

So most organizations either abandon measurement entirely or settle for theater. Neither helps you understand what’s working.

The real measurement challenge isn’t proving ROI. It’s tracking behavioral change as it happens (or doesn’t happen). Because the gap between “good coaching session” and “actually doing things differently three weeks later” is where most coaching value disappears.

You leave the session committed to delegating more effectively. Three weeks later, you’re still the bottleneck making every decision, but you don’t notice because you’re too busy to notice. Your coach asks “how’s the delegation going?” in your next session, and you genuinely believe you’ve improved. You haven’t. You just can’t see what you’re doing.

This is the noticing gap: the space between knowing what to change and seeing when you’re not changing it.

Traditional coaching measurement tries to solve this with quarterly check-ins. But quarterly is far too slow to catch backsliding. By the time you get the data, you’ve reinforced the wrong pattern for three months.

AI changes this because it can notice for you.

Not in some dystopian “your boss is watching” way. In a “here’s what you actually did this week vs. what you said you’d do” way. AI can analyze your communication patterns, surface your defaults under pressure, and show you the exact moment you stopped delegating and started solving.

It’s a mirror that doesn’t require you to remember to look in it.

The Framework: What to Track

When I work with clients on coaching and development, we use a simple structure: Insight → Action → Evidence. You need to know what you’re trying to change (insight), experiment with doing it differently (action), and gather proof that something shifted (evidence).

The problem is the evidence part. Most organizations either abandon measurement entirely (”you can’t measure soft skills”) or default to theater (satisfaction surveys that tell you nothing about behavioral change).

The middle ground is triangulated observation: multiple signals, both quantitative and qualitative, that let you see patterns without pretending you can reduce human development to a single number.

AI fits here perfectly. Not as the measurement system, but as the pattern-recognition tool that makes your own behavior visible in real-time.

How This Actually Works

Instead of reviewing your quarter once every three months, you can review your week every Friday. You feed AI your actual communication - emails, Slack messages, meeting notes - and ask it to show you your patterns.

Not vague “how am I doing?” questions. Specific behavioral analysis tied to what you’re trying to change.

Don’t overthink the selection process. Open your calendar, find the most stressful meeting you had last week, and export the emails you sent in the hour immediately following it. That’s your data.

Here’s one example. This month’s focus is resilience - so let’s look at how you show up under pressure.

Prompt: Pressure Degradation

I want to understand how my behaviour changes under pressure. Below are two sets of messages - Set A (business as usual) and Set B (high pressure/crisis mode).

Compare them and tell me:

1. What specific language disappears when I’m under pressure?
2. What shows up instead? (Quote exact phrases)
3. Do I get shorter, longer, more direct, more vague?
4. What do I stop doing when stressed that I do when calm?
5. Give me one early warning sign that I’m shifting into pressure mode

Be specific - quote my actual language so I can catch this pattern in real-time.

What you feed it: 6-10 emails or Slack messages - half from normal times, half from high-pressure situations (you’ll know which is which).

⚠️ Data Safety: If you aren’t using an Enterprise instance of ChatGPT/Claude, please anonymize your text before pasting. Strip out specific names, dollar amounts, and proprietary strategy details.

Cadence: Monthly pattern check, or after any high-pressure period

What this surfaces: Your stress tells. The specific ways your communication degrades under pressure. Most people don’t realize they have a “stressed version” of themselves that shows up predictably. This prompt makes it visible.

The AI won’t sugarcoat it. It’ll quote your exact language back at you and show you what disappears (context, empathy, clarity) and what shows up instead (shortness, vagueness, command mode). That’s behavioral evidence you can work with.

Maybe you discover you stop explaining “why” when you’re stressed and just start announcing “what.” Maybe your sentences get clipped and your tone shifts to pure transaction. Maybe you stop asking questions and start directing.

Whatever your pattern is, you can’t change it if you can’t see it. This makes it visible.