From: The NoW of Work
MacKay CEO Forums Innovation Partner

If You're a MacKay Member, Your Chair Already Knows Three Things About You:

First: You've sat through at least one AI presentation in the last 90 days that was either (a) technically impressive but operationally useless, or (b) strategically sound but politically impossible to execute in your organization.

Second: You've got at least one executive team member who thinks you're moving too slow, and at least one who thinks you're being reckless. Both are vocal about it.

Third: Your board is asking questions you can't yet answer with the confidence they expect from you.

If any of that sounds familiar, this message is for you.

If you've already figured all this out and have AI adoption humming along, you can stop reading. This isn't for you.

But if you're in the messy middle (where most MacKay members are right now) here's what you need to know about why this is harder than it should be, and what actually works to fix it.

The Expensive Mistake Most Mid-Market CEOs Are Making Right Now

Let me be direct: Most organizations are approaching AI adoption backwards.

They're starting with tools, when they should start with leadership.
They're hiring consultants who deliver decks, when they need people who can install capability.
They're trying to "pilot" their way to clarity, when what they actually need is a clear point of view first.

Here's what this looks like in practice:

Your CTO buys enterprise AI licenses for the team.
Your CMO runs a separate pilot with different tools.
Your CFO demands ROI metrics nobody can produce yet.
Your CHRO worries about job displacement.

Six months later, you've spent $180K+ on licenses, everyone's experimenting in silos, and you still can't answer your board's basic question: "What's our AI strategy?"

The real cost isn't the wasted licensing fees.

It's the 6-12 months you lose while competitors figure this out faster. It's the top performers who leave because your organization feels behind. It's the credibility you burn with your board when you can't articulate a coherent position.

One MacKay member told me recently: "We've spent $220K on AI tools and training this year. The only thing we've definitely produced is confusion and Slack threads about which tool to use."

Sound familiar?

Why Traditional Consulting Approaches Fail at This

Here's the uncomfortable truth: Most consultants are spectacularly bad at AI adoption work.

The Big 4 firms send recent MBAs with slide templates. You get a 180-page strategy document and zero capability transfer. Six weeks after they leave, nobody can remember what the recommendation was.

The AI-native consultants are technically brilliant but organizationally naive. They don't understand why your 52-year-old VP of Operations isn't as excited about prompt engineering as they are. They treat change management as an afterthought.

The change management specialists understand your organization but don't understand AI. They can run a workshop, but they can't show your team how to actually use these tools in their daily work.

You end up with one of three outcomes:

1. Nothing happens. The strategy sits in a drawer. (Most common)

2. Chaos happens. Teams rush ahead without guardrails. (Second most common)

3. Theater happens. You do just enough to satisfy the board but not enough to matter. (Almost as common)

What you need—and what most firms can't deliver—is someone who can do three things simultaneously:

• Create leadership alignment (the strategy piece)

• Build practical capability (the doing piece)

• Install guardrails (the governance piece)

That combination is rare. Most consultants can do one, maybe two. Very few can do all three.

That's the gap MacKay asked us to fill.

What Actually Works: The Three-Layer System

Over the past 18 months, we've worked with 47 mid-market organizations on AI adoption. (Twelve of them are MacKay members, though we'll only name them with permission.)

Here's what we've learned:

The organizations that succeed don't treat this as a technology project. They treat it as a leadership behavior change project that happens to involve technology.

They work in three layers, in this specific order:

Layer 1: Executive Alignment (The "Boardroom Clinic")

The problem it solves: Your executive team is operating from different mental models. Your CTO thinks this is about infrastructure. Your CMO thinks it's about customer experience. Your CFO thinks it's about cost reduction. Your CHRO thinks it's about risk.

They're all right. They're also all talking past each other.

What we do: We run a 4-hour working session (not a presentation—a working session) where we create a shared mental model your entire executive team can own.

Specific outcomes:

• One clear point of view on where AI creates leverage in your business (and where it doesn't)

• Shared language your team can use consistently with board, staff, customers

• Specific decision on where to focus first (and what to explicitly postpone)

• Answers to the 8-10 questions your board will definitely ask

Recent example: A $180M distribution company (MacKay member) came in with executives pulling in four different directions. After the clinic, their CEO told us: "First time in six months we've been in the same conversation. We finally know what we're doing and why."

That clarity is worth 6-12 months of execution time.

Investment: $12,000
Timeline: Schedule and complete within 2 weeks
ROI: Typical client saves $80K-$150K in wasted pilot spending in first 90 days

Layer 2: Team Capability Building (The "Adoption Training")

The problem it solves: Your teams don't need more awareness. They need actual skill. They need to know what "good" looks like, what the guardrails are, and how to use AI in their specific workflow without you micromanaging it.

What we do: Four-week hands-on program with 8-15 people. They learn by doing actual work, not theoretical exercises.

Specific outcomes by week:

• Week 1: Core competence in 3-4 tools relevant to their work; confidence to experiment safely

• Week 2: Three "quick win" use cases deployed in their actual workflow

• Week 3: Daily habits established; capability to train others on their team

• Week 4: Visible results they can report up; momentum that continues after we leave

Recent example: Sales team at a $95M manufacturing company (not MacKay). Week 1 they learned the tools. Week 2 they redesigned their proposal process. Week 3 they cut proposal turnaround time from 11 days to 4. Week 4 they closed two deals that were stalled specifically because they could respond faster than competition.

That sales team paid for the entire engagement in 30 days.

Investment: $18,000
Timeline: 4 weeks, one session per week
ROI: Clients typically recoup investment through time savings within 60-90 days

Layer 3: Organizational Installation (The "Culture Code Transformation")

The problem it solves: Pockets of capability don't scale. Individual wins don't compound. You need organization-wide muscle, not hero-dependent success.

What we do: 4-month engagement to install a shared "Culture Code"—the beliefs, behaviors, and guardrails that make AI a native organizational capability, not a special project.

Specific deliverables:

• Month 1: Executive alignment and Culture Code definition

• Month 2: Capability installation across 3-5 functional groups

• Month 3: Guardrails and governance integration

• Month 4: Operating rhythm establishment and handoff

Recent example: $240M financial services firm (MacKay member). Four months in, they've got 85 people using AI daily across six departments, clear governance, and consistent capability. Their CEO's quote: "This is the first initiative in three years where I'm not the bottleneck. It's actually running without me."

That's what "installed" looks like.

Investment: Starting at $75,000
Timeline: 4 months
ROI: Clients typically see 3-5x return through productivity gains and faster decision cycles within 12 months

How MacKay Members Typically Use This (And What Doesn't Work)

Three common patterns:

Pattern 1: Start with Boardroom Clinic (47% of MacKay members)

Most common when:

• Board pressure is building

• Executive team is misaligned

• You need clarity fast before making bigger commitments

Success rate: 92% move to next layer within 90 days
What kills it: CEO doesn't bring actual decision-making authority to the session

Pattern 2: Jump to Adoption Training (31% of MacKay members)

Most common when:

• Teams are already experimenting but inconsistently

• You need quick wins to build momentum

• Leadership alignment exists but capability doesn't

Success rate: 78% get measurable results within 60 days
What kills it: Selecting wrong team (heroes vs. skeptics) or no executive sponsorship

Pattern 3: Commit to Full Transformation (22% of MacKay members)

Most common when:

• AI is strategic priority for next 12-24 months

• You need enterprise-wide capability, not pilots

• Board expects significant organizational change

Success rate: 100% complete program; 87% extend engagement
What kills it: CEO doesn't stay engaged; treating it like vendor relationship instead of strategic partnership

The wrong pattern: Waiting for clarity before acting.

We see this all the time. CEO wants to "think about it" or "see what happens" before committing. Six months later, they're further behind and under more pressure.

The cost of waiting is real. Your competitors aren't waiting. Your board's patience isn't infinite. Your best people are watching.

Why MacKay Selected The NoW of Work (And What Makes This Different)

Your forum didn't pick us because we're the biggest or the cheapest.

They picked us because we do three specific things most consultants can't or won't do:

1. We've actually done this. Not once or twice—47 times in 18 months. We know what works, what fails, and why. We've seen every failure mode. We've debugged every objection.

2. We transfer capability, not dependency. When we leave, your team can run this without us. That's the point. We're not building an annuity relationship—we're building your internal capability.

3. We have skin in the game. Our reputation with MacKay depends on your results. If you don't get value, we don't get referrals. Simple as that.

Specific proof points:

• 47 engagements, 18 months

• 12 MacKay member organizations (names available on request)

• 92% would recommend us to peers (verified by MacKay)

• Zero clients who completed Boardroom Clinic failed to get board-ready clarity

• Average time savings reported by Adoption Training teams: 4-7 hours per person per week

• 87% of Transformation clients extend engagement beyond initial 4 months

What we won't do:

• We won't take your engagement if your executive team isn't actually aligned on wanting to solve this

• We won't work with you if you're looking for someone to blame when this is hard

• We won't pretend this is easy or that you can skip the leadership work

What we will do:

• Tell you the truth about what's working and what isn't

• Push back when you're making predictable mistakes

• Help you move faster than you thought possible while avoiding the chaos

Three Reasons Not to Work With Us

Let me save us both some time.

Don't engage if:

1. You're Not Actually Ready

If you're still in "we should probably think about AI" mode rather than "we need to figure this out now" mode, you're not ready. This work requires real commitment. If you're looking for someone to do your thinking for you, we're not a fit.

2. You Want Vendors, Not Partners

If you want to spec this out, get three bids, and pick the cheapest, we're not your firm. This isn't transactional work. It requires trust, candor, and partnership. If that sounds like consultant-speak to you, we're not aligned.

3. You're Not Willing to Change

If you want to bolt AI onto your existing structure without changing anything about how your organization operates, this won't work. AI adoption requires leadership behavior change. If that's not on the table, save your money.

Still reading? Good. Here's what to do next.

How to Move Forward (If This Resonates)

Step 1: Talk to Your Chair

They know your context. They know what other members have done. They can help you think through which entry point makes sense.

They may also connect you with another MacKay member who's been through this work. That peer conversation is often more valuable than anything we could tell you.

Step 2: Schedule a Discovery Session

30-45 minutes with our team. We'll dig into your specific situation and tell you honestly whether we think we can help.

What we'll cover:

• Where you are today (candidly)

• What's blocking progress (specifically)

• Which approach makes sense for your context (and why)

• What ROI looks like in your situation (with numbers)

What we won't do: Pitch you. Give you a canned presentation. Try to upsell you into something you don't need.

Step 3: Make a Decision

If it's a fit, we move fast. Boardroom Clinics can be scheduled within 2 weeks. Adoption Training within 3 weeks. Transformation engagements within 30 days.

If it's not a fit, we'll tell you that too. And we'll point you toward what might work better.

The Real Question

Here's what this comes down to:

Twelve months from now, will you be the CEO who figured this out while your competitors struggled?

Or will you be explaining to your board why you're still "evaluating options" while your best people leave for organizations that have their act together?

The gap between those two futures is closing.

Some of your MacKay peers have already made the call. They're 6-9 months ahead of where they were. They're having different conversations with their boards. Their teams are operating differently.

You can join them, or you can keep thinking about it.

But I can tell you this: Nobody regrets moving on this quickly. Lots of people regret waiting.

Your move.

→ Talk to Your Chair
→ Schedule Discovery Session: [calendar link]
→ Email Direct: [contact@thenowofwork.com]
→ Call: [phone number]

The NoW of Work is a vetted strategic partner of MacKay CEO Forums. We were selected based on demonstrated results with member organizations and verified by your forum's leadership team.

All client results cited are accurate and verifiable. Names available upon request for reference checks.