Dear Executive Leadership (at large): It's Not Me. It's You.

A Valentine’s Day breakup letter, because we can't scale this relationship without a real partnership in redesigning the system.

Dear Executive Leadership,

I know the last couple years of our relationship has been… complicated. But this isn’t working the way you keep promising it will.

To be honest, you keep introducing me like I’m a transformation. Then you manage me like I’m a pilot. You rolled out access and expected adoption. But access isn’t commitment, especially when the work, metrics, and decision paths stay the same.

And while you two-step between hype and pilots, it’s your early adopters and implementers who keep getting tasked to translate the organization's ambition into workflows.

You keep asking for production value, but most of what you call “progress” still lives in experiment mode. Deloitte’s 2026 State of AI in the Enterprise shows only 25% of organizations have moved 40%+ of AI experiments into production.

That’s not a technology gap. That’s a leadership gap.

And the job redesign piece? That’s the part you keep dodging. Deloitte reports 82% expect 10%+ of jobs to be fully automated in the next three years, while 84% haven’t redesigned jobs around AI capabilities.

You can’t strap new tools onto old roles and call it transformation. That’s just extra work with better branding.

So here’s what really needs to change if we’re staying together:

• Stop measuring activity and start measuring outcomes. Fewer “number of pilots” updates. More customer and employee outcomes that hold.

• Build a real path from pilot → production. Owners. Criteria. Funding. Timelines. No more “prove it again” loops.

• Redesign workflows and roles around how work actually gets done now. Decision rights. Quality checks. Human ownership. Clear handoffs.

• Fix governance so it enables safe scale instead of showing up late as a blocker. Clarity beats fear. Guardrails beat guesswork.

• Resource this like transformation, not like a side project. Training, integration, enablement and matching the expectation you set.

• Lead this as a human-led transformation, not a tool rollout. Clear ownership, role-based training, change enablement, and support for the people doing the work—so early adopters aren’t forced to improvise the operating model.

Until then, you’re not asking me to assist your teams in transforming the business. You’re asking me to decorate a system you apparently don't feel the need to actually change.

So consider this my Valentine’s Day breakup letter, unless you’re ready to take it to the next level in the only way that counts: by redesigning the system.

Respectively,

AI

XOXO (pending change)