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The question missing from your AI implementation plans

Oct 01, 2025
Just because you can with AI, doesn't mean you should

I'm back from my birthday weekend spent in the Highlands (🥳) to an inbox rammed with quite obviously AI-automated cold outreach (👎). Mostly selling AI-automated cold outreach services (🙄).

I'm not anti-cold outreach. Times are tough and you've gotta do what you've gotta do. I'm anti-generic, impersonal, irrelevant and just plain old lazy cold outreach.

Which leads to today's talking point...

The strategic question missing from AI conversations

Often, I think we're so focused on what AI can do, we forget to ask what AI should do. Small word difference, but it changes so much about how you approach AI in your business.

This is the reframe I challenge my clients to consider.

Most conversations about AI start with capability. "Look what this tool can automate!" "See how much faster this makes us!" "Check out these efficiency gains!"

All valid and I understand the excitement. But IMHO organisations are doomed to fail if they never move beyond that first question of capability.

They're so dazzled by what's technically possible, they forget to ask whether it's strategically wise.

Moving beyond AI capability to AI strategy

So I push my clients to pause and consider the "should" questions:

  • Should we automate this process, or does human judgement add value we haven't recognised?
  • Should we optimise this workflow for speed, or is it a process that benefits from being slow and a little (dare I say) messy?
  • Should we remove the human touchpoints, or are those conversations where real relationships are built?
  • Should we solve this with AI, or is the real problem about communication, training or organisational design?

This reframe brings intentionality to the fore.

Why intentional AI implementation matters

The "can" question gets you excited about possibilities. The "should" question gets you focused on outcomes.

(btw this why I think, with careful management, the strongest teams have both sceptics and enthusiasts working constructively together)

I believe those who spend time on the "should" conversation upfront will end up with thoughtful AI implementations their teams are invested in. Because they've thought through not just the technical feasibility, but the human and organisational fit.

AI ethics and long-term thinking

And the "should" conversation is fundamentally an ethics conversation (so, something I can help you with 😉). It forces you to think longer term and consider impact, consequences and alignment with your organisation's values.

When you view AI through this lens, I believe there's potential to build systems that make work more meaningful, not just faster.

That's the kind of transformation I can get excited about — and something I have more thoughts on coming soon.

Want to explore the "should" questions for your organisation? Book a time to chat here.

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