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The wrong first question about AI and contracting - and why we built our assessment tool

TL:DR: AI is uncompromising. Connect it to a contracting process that isn't ready, and it won't smooth over the gaps - it'll expose them. Here's why we think foundations come first, and why we built a two-minute scorecard for you to check them.

Before most of our smarter contract delivery webinars, we ask a question- what do you want us to make sure we cover? Lately, the questions have started to repeat. What are the first three things to try? How much faster? How to do more without adding heads? All fair - it's what everyone's leadership is asking them right now. 

We also kept noticing something underneath the questions and in conversations - teams are focused on the AI tool and what it does, before they've looked at the environment it's operating in.  

Now a little context.

The top two themes are nearly 40% of everything asked, over 83 questions:

  1. Getting started. Where do I begin? What's the low-hanging fruit? What does "good" even look like?
  2. Adoption. How do I get my team - especially the sceptics, to use this consistently to show results?

Now, thinking about the top two question themes in the context of tool first, foundations later – it sounds like a recipe for a poor outcome, destroying the core of the ultimate objective.

So, we built something to help teams check the ground first. Here's the thinking behind it.

AI exposes a process. It doesn't fix one.

There's a hope buried in a lot of AI conversations - that the tool will smooth over the messy bits. It won't. AI is uncompromising in a way people underestimate. Point it at inconsistent templates, incomplete/unreviewed playbooks, or a workflow no one has actually mapped, and it doesn't work around the gaps, it raises every one of them.

That inconsistency you'd learned to live with? The tool flags it, every time. The “we just know how we do it here” knowledge that lives in three people's heads? The tool needs it written down - and discovers it isn't. None of this is the tool failing, it's doing its job: showing you the process you actually have, not the one you assumed you had.

The teams who are getting substantial value from AI already knew this. They sorted their foundations first, so the tool had something solid to work with. The teams who struggle bought the tech hoping it would do the sorting for them.

Moving fast is not the same as moving well

The pressure is to move quickly, and we understand why. Add speed onto weak foundations doesn't get you there faster, it just gets you to the problem faster.

We've watched implementations stall halfway through, when the tool surfaces more inconsistency than anyone budgeted time to fix. We've seen the friction spill across functions - legal, procurement and sales pointing at each other while the tool sits there, correctly, refusing to pretend the gaps aren't there. We’ve also seen the expensive version: a tool that technically works, bolted onto a messy process, so all it really does is automate complexity faster.

None of that is an argument against AI. It's an argument for knowing where you stand before you start.

What “foundations” actually means

Foundations sounds vague, so here's the plain version. It's a handful of unglamorous things: are your templates consistent, are your playbooks written down rather than remembered, is your workflow mapped rather than assumed, and do you know your own numbers well enough to tell whether anything improved.

That last one matters more than people expect - which brings us to why we measure.

Why we measure before we build

If you can't describe where you are today, you can't prove where AI took you. No baseline, no before-and-after, no defensible ROI - just a feeling that things are a bit better, which is the first thing to get cut when budgets tighten.

Measuring first does two things. It tells you which foundation to fix before you spend, and it gives you the starting line you'll need to show the gain later. That's the difference between a one-off win you can't quite account for and sustainable building you can stand behind in front of a board.

This is how our teams think about every AI in contracting conversation we have: foundations before tools, measurement before money. Not because it's cautious or prudent but because it's the version we know that actually works.

The two-minute version

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If your score points to work to do - and for most teams it does - our guide walks through how to get those foundations right, step by step.  Read the guide.

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