The Digital Transformation Playbook

Leading AI Starts With Behaviour, Not Code

Kieran Gilmurray

The promise of AI isn’t stalling because the models are weak; it’s stalling because our leadership habits are. 

We open the hood on why executives talk about stewardship and enterprise health while managers feel like they’re juggling a second job just to keep up, then add AI on top. 

The tension isn’t about tools. It’s about incentives, silos, and the courage to share ownership for outcomes that cut across the org chart.

TLDR:

  • AI framed as a leadership and behavioural challenge 
  • Disconnect between C‑suite aspirations and operational reality 
  • Managers feeling AI as a “second job” without role redesign 
  • Need for shared executive ownership across functional boundaries 
  • Team coaching to move from polite alignment to joint accountability 
  • Incentives driving individual attainment over enterprise outcomes 
  • Governance and KPIs that reward cross‑functional results 
  • AI as an accelerant of existing misalignment if behaviours do not change

Across a candid, practical conversation, we explore how automation refuses to respect functional boundaries and what that means for the C‑suite. If rewards are tied to individual attainment and quarterly optics, leaders will say “collaborate” while behaving in ways that block end‑to‑end value. 

We dig into team coaching as a lever for change shifting executive teams from polite alignment to genuine joint accountability, setting shared KPIs, and making decisions that trade local optimisation for enterprise results. 

We also get real about the strain on middle managers who hear the AI mandate but lack redesigned roles, budgets, and guardrails to make it work.

You’ll hear clear steps for turning intent into impact: name the vision–reality gap, sponsor value streams that span functions, co-own outcomes at the top, and create short learning cycles where cross-functional teams can test, measure, and adapt. 

We talk governance that empowers rather than slows, incentives that reward cross-boundary wins, and behaviours that build psychological safety so constraints surface early. If you want AI to be a force multiplier instead of a stress multiplier, start by rewiring how leaders lead together.

If this conversation resonates, follow the show, share it with a colleague who’s navigating AI at scale, and leave a review to help more leaders find it.

Are you struggling with AI or do you need fractional executive help implementing AI in your business? 

If the answer is yes, then lets chat about getting you the help you need - https://calendly.com/kierangilmurray/executive-leadership-and-development


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SPEAKER_00:

What was it that first convinced you that AI is less of a technology issue and more of a leadership and a behavioral issue? There's an absolute disconnect between the C level execs that I'm coaching who they like to talk about being custodians of an organization's health, of its capacity, of its profit, which is right. Look, you know, I'm struggling to do my job as it is. Now, with all of this new AI stuff coming in, it kind of feels to me like I have to learn to do a second job on top of the job that I'm struggling to do. And I think that is part of the problem. And there is a gap which needs to be bridged between what the C level executives would like to see in terms of desired outcomes and the messier reality of where the organization actually is. And I think that bridge or that gap needs to be bridged. Um, in terms of the behavioral piece, um, you know, I would do individual coaching. I I also probably do more team coaching when we are talking about AI broadly, because what I you know, my understanding, I'm not an AI or digital transformation expert, and I deal with the people who are trying to deal with that stuff. But I do I do see AI will require much more of a shared responsibility at executive level. Um, and I think this is kind of at the heart of the issue, Kieran. You know, a lot of executives are have been promoted, they're very, very successful, they're they're very well paid, and they are that that happens on this quarterly cycle of delivering results to to external analysts, and it's a hamster wheel that they're on. So and and and remuneration is also based on individual performance and attainment. And with AI, I think you know, AI is not a respecter, automation is not a respecter of functional silos, you know, by its very nature, it wants to cut across the enterprise. And uh I think the senior executives behaviorally um could be better, some some are excellent already, of course, but uh I think it's quite mixed in terms of the level of sophistication at the sea level um with this sense of shared ownership to the corporate mission. Um, I think they they say they do it, but when you get into but actually, are you accountable for your colleagues' success? I don't think they're there yet. And and again, AI is just going to inject steroids into that. I think it's a problem.