The Fit-Gap Fallacy: More than a checklist
This is the fifth post in our Strategy Series, published every Thursday. Each week, we explore how Australian organisations can rethink their operating models, embrace AI with intention, and stay ahead of the curve. In this post, we go right back to the start, before operating models, before requirements. How do you start?
A lot of teams treat fit-gap like a scorecard, but that’s a great way to pick the wrong solution.
Here’s the thing no one tells you: most fit-gap analysis is theatre. Stakeholders fill in a matrix, tally the ticks, and call it alignment. But real alignment has nothing to do with checkboxes, and everything to do with what you're actually trying to change.
When we run fit-gap at We Lead Out, we don’t start with features. We start with ambition.
Here’s how we break it down:
Start with future-state clarity
You can’t assess fit unless you know what “fit” means. That means:
What’s non-negotiable for how we work?
Where are we willing to flex?
What are we trying to enable, and not just replace?
This stops teams from over-specifying, over-engineering, and overspending.
Use three lenses, not one
Most people stop at functional fit. We add:
Functional: Does it do what’s needed?
Technical fit: Can we integrate it? Maintain it?
Cultural fit: Will our people actually use it?
That last one is make-or-break. Adoption risk hides in culture, not config.
Make each gap count
Every gap should trigger a choice:
Change the process
Customise the tech
Reframe the requirement
Park it for later
If you’re not mapping gaps to decisions, you’re just making lists.
Visualise impact, not volume
We don’t report on “number of gaps”. We show the total cost of ownership. Which gaps are expensive? Which delay delivery? Which ones kill momentum?
A red heatmap highlighting a decision-critical gap grabs attention quickly.
Use it as a cross-functional tool
We bring fit-gap insights into the room with product, finance, operations, and change leads. Why? Because that’s who owns the trade-offs. This is where solution design becomes business design.
The takeaway:
Fit-gap is only useful if it helps you make better decisions, faster. Otherwise, it's just noise dressed up in a spreadsheet.
Need to make solution choices with eyes wide open?
We run fast, collaborative fit-gap sessions that strip away the noise and surface what really matters. Get in touch—let’s make sure your next platform choice fits you, not just the feature list.
We Lead Out helps business and government leaders navigate transformation with confidence, starting with the foundations that matter. Reach out to learn more about the trends affecting Australian businesses.
Let’s talk
Connect with me on LinkedIn to get started designing your AI-Native operating model.
Follow We Lead Out on LinkedIn to keep learning with us.