Dear CEO – Canada is collecting names instead of building an implementation engine

Dear CEO – Canada is collecting names instead of building an implementation engine

Oct 3, 2026

We have an implementation gap in AI Governance and a missed opportunity for global responsible AI leadership.

Prestige is not a strategy.

A council of Canadian stars is useless if no one knows how to land the plane.

Canada recently announced a high profile AI advisory council led by Mark Carney.

The list of names is impressive.

It includes the giants of research and the heavyweights of venture capital.

But there is a massive blind spot in this group.

The council is heavy on thinkers and investors but remarkably light on the people actually tasked with the operational reality of AI.

To move business adoption from 12% to 60% by 2034, Canada needs more than academic consensus and capital.

It needs the implementation layer.

This means the people on the ground who manage generative & agentic AI, machine learning, computer vision, and natural language processing in live production environments.

It also means the architects preparing for the shift from generative models to agentic AI systems.

The argument for a top down approach is that consensus among research and capital creates the necessary market stability.

Stability does not equal adoption.

If the policy focuses only on the frontier models and ignores the messy reality of enterprise data governance and infrastructure, the target will remain out of reach.

Evan Solomon please do not forget:

1. To mandate representation from the implementation layer to include practitioners who govern live models.

2. To expand the strategic scope beyond generative hype to include the full spectrum of other "AI" architectures such as machine learning and computer vision.

3. To focus on the specific data readiness required for the transition to agentic AI enterprises.

Is your organization waiting for government guidance or are you building the internal governance required to actually use the technology?

#AI AIGovernance Canada

Dear CEO – Your upskilling program might actually be a slow motion severance plan

Dear CEO – Your upskilling program might actually be a slow motion severance plan

Oct 2, 2026

Most leaders view L&D as the primary lever for AI adoption.

A recent PwC survey of 50,000 workers found a widening divide between the front runners who use AI daily and the engine room which makes up 56% of the workforce.

While the front runners have the tools and the training, the engine room is being left behind.

I have seen this play out in almost every transformation initiative I have undertaken because the lack of digital literacy in core staff acts as a massive drag on every high ROI tool you try to deploy.

It is not a software problem.

When your engine room, which makes up 56% of your staff, cannot navigate even basic digital workflows, the issue is more than a simple training gap.

It is a question of structural incompatibility.

You are effectively subsidizing the training of people for roles that the technology will render obsolete within 24 months.

Some will argue that maintaining a stable, non AI dependent core is essential for operational resilience.

They believe you cannot just discard your most reliable workers.

I agree that stability is vital, but there is a difference between stability and subsidizing obsolescence.

If the tool requires a level of digital fluency that the majority of your staff cannot reach in a reasonable timeframe, that role is already gone.

1. Audit your L&D spend to see how much goes to roles that won't exist in 24 months.

2. Map digital literacy requirements against your engine room's current baseline.

3. Redesign roles to be AI native rather than trying to force fit legacy processes into new tools.

Are you investing in your people or are you just paying for a slow transition to a smaller workforce?

#AIStrategy #WorkforceTransformation #Leadership #FutureOfWork

Dear CEO – The Silence of AI Shame

Dear CEO – The Silence of AI Shame

Oct 1, 2026

Your AI adoption metrics are a lie.

You think your teams are transforming but they are actually just hiding.

A recently highlighted phenomenon is one of AI shame.

Employees often feel like they are cheating when using Generative AI tools.

When people feel ashamed to admit they used a tool, the feedback loop breaks and you lose the ability to scale what you cannot see effectively.

I have seen a colleague refuse to acknowledge AI assistance because they view it as a form of dishonesty.

Data becomes wrong.

If employees hide the how behind their output, your productivity metrics become purely speculative.

You are measuring ghosts.

You cannot scale.

1. Create a sandbox environment for experimentation where failure is expected and usage is celebrated.

2. Shift the conversation toward business outcomes.

3. Standardize the disclosure of AI involvement in internal processes to normalize the tool as a standard assistant.

If your people are afraid to admit they use it, what are you actually measuring?

#AIStrategy #EnterpriseTransformation #DataGovernance #Leadership #DigitalTransformation

 

Dear CEO – Your job isn’t to imagine the future – It is to force people to talk

Dear CEO – Your job isn’t to imagine the future – It is to force people to talk

Sep 29, 2026

The industry loves the word visionary.

It sounds prestigious.

It looks great on a board slide.

But vision alone is a passive activity.

In my two decades at the executive table and advising boards, I have seen countless transformations die not because the vision was wrong, but because the integration was non-existent.

The reality of complex change is that your CIO, CFO, and COO are likely speaking three different languages.

They are optimizing for their own KPIs while ignoring the gaps between them.

True leadership in transformation requires moving from the ivory tower to the engine room:

First, stop asking if a project is on track. Start asking who is not talking to whom. The friction points are where the real risk lives.

Second, dismantle the "update culture." Status reports are designed to hide failure. Real integration happens in the uncomfortable conversations where conflicting priorities are laid bare.

Third, recognize that forcing communication is an act of will. It is tedious and often confrontational work, but it is the only way to ensure a strategic objective becomes an operational reality.

If you are spending 90% of your time on the "where" and 10% on the "how people connect," you aren't leading a transformation. You are dreaming one.

CEOs should audit their calendar this week: How much time is spent on visionary slides versus forcing disparate teams to resolve dependencies?

Is your current focus on the destination or the plumbing?

#DigitalTransformation #ExecutiveLeadership #CorporateStrategy #ChangeManagement #CanadianBusiness #OperationalExcellence

Dear CEO – Your Risk Committee is not equipped to govern AI

Dear CEO – Your Risk Committee is not equipped to govern AI

Sep 28, 2026

Treating AI as just another line item on a risk register is a recipe for stagnation or catastrophe.

In my time advising boards or sitting at the executive table, I have seen this play out repeatedly.

When AI oversight is embedded solely within the Risk Committee, the conversation defaults to prevention.

You talk about data privacy and hallucinations. You talk about compliance.

But you never talk about value creation.

Risk committees are designed to say no or "not yet."

AI transformation requires a mandate to move fast, iterate, and pivot.

If your board lacks a dedicated Technology and AI Committee, you are creating a structural bottleneck.

You leave the CIO in a vacuum, pushing for acceleration while the Board only views the technology through the lens of liability.

The gap between risk mitigation and strategic acceleration is where most digital transformations fail.

Here's Your Action Plan:

Audit your current committee charters.

If AI oversight is buried under "Risk," you are managing a threat, not leading a strategy.

Establish a dedicated mandate focused on capability and competitive advantage, separate from the audit and risk functions.

Is your board governing AI to prevent failure, or to enable growth?

#BoardGovernance #CorporateStrategy #ArtificialIntelligence #DigitalTransformation #CanadianBusiness #ExecutiveLeadership

Dear CEO – The AI Scaling Paradox

Dear CEO – The AI Scaling Paradox

Sep 25, 2026

AI is a luxury for the large, but a survival requirement for the small.

The impact is not equal.

In a 200 person company, AI experimentation is a ripple in a pond.

In a 5 person company, it is a tidal wave.

When your lead salesperson spends 20 percent of their week playing with AI, you have not just lost 20 percent of their time, because you have actually lost 20 percent of your entire company's capacity.

For a founder, that is the difference between hitting your numbers and missing them.

Most small teams are currently using AI as a distraction.

They are attempting to learn how to build the engine rather than just driving the vehicle.

This results in a massive loss of productivity during the very stage where every minute of capacity is critical to your growth.

You need utility.

Small teams need to experiment to find their competitive edge.

But experimentation is a luxury you cannot afford when you are growing.

You do not need your team to be AI experts.

You need them to use the output of AI to do the job they were actually hired for.

1. Stop allowing unstructured exploration in core roles.

2. Prioritize workflows that integrate into existing tasks.

3. Measure success by the capacity it returns to your team.

Is AI adding to your capacity or adding to your distraction?

#SmallBusiness #Founders #Growth #AIStrategy