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Session 03 · Alignment

Three leaders, one plan — or so everyone assumes.

Ask your executive sponsor, your board, and your program lead the same three questions about your AI priorities — separately — and the answers usually don't match. Misalignment rarely looks like an argument. It looks like three confident people each running a slightly different program.

By Joe Perone, Senior Principal Last updated

What we talked through

One initiative, three definitions of success — and all three are held with equal confidence:

  • The executive sponsor (ED or CEO) wants "an AI strategy" and mission or business impact.
  • The board wants risk minimized and a defensible, fiduciary story.
  • The program lead wants workload reduced and something shippable.

Here's the trap: alignment almost never breaks at the mission — everyone agrees "we should use AI." It breaks at the metric, where almost nobody agrees what winning actually looks like. A related failure mode is sponsorship without authority — a champion who's genuinely excited but can't unblock data access, budget, or staff time. Three questions, answered independently, surface both fast:

  1. Success: what does success look like in 90 days?
  2. Trade-off: what are we willing to stop doing to make room for this?
  3. Authority: who has the authority to say no, or to kill it?

The point isn't to win the argument. It's to make disagreement visible while it's still cheap — before kickoff, not after. And it's worth naming the harder possibility out loud: sometimes misalignment isn't a communication gap at all, but a genuine disagreement about priorities everyone's been avoiding.

Interactive · ~90 seconds

The Alignment Test

Fill in each stakeholder's answer to the three questions — as one person imagining all three views, or share the page and have three people fill their own column. Each question flags whether the answers align or diverge.

1. Success — what does it look like in 90 days?

Awaiting input

2. Trade-off — what will we stop doing to make room?

Awaiting input

3. Authority — who can say no or kill it?

Awaiting input

Alignment read

Fill in at least two columns on a question to see whether they align.

A conversation starter, not a verdict — matching text is a rough proxy. The value is in comparing the answers out loud.

Take it with you

The three alignment questions

Three questions to ask each AI stakeholder, and what alignment versus divergence looks like.
Question Aligned looks like Divergent looks like
90-day successOne shared, specific picture of a win 90 days out.Strategy vs. risk-avoidance vs. shipped feature.
Trade-offAgreement on what gets paused to make room.Everyone expects it to be done "on top of" today's work.
AuthorityOne clear person who can say no or kill it.A champion with enthusiasm but no power to unblock.

Run it with your real stakeholders

Get the Alignment Test as a shareable one-pager

A printable version you can hand to your sponsor, a board member, and your program lead — three columns, three questions, filled in independently. We'll email it now.

No spam, no drip sequence. We use your email to send what you asked for and, at most, one follow-up. Prefer to talk? Book a 30-minute strategy call — no deck, no junior gatekeeper.

Last updated