Leadership | Alidade Strategies Inc.

Dear CEO – The era of human‑only phishing is over — today’s cyber attackers deploy AI that talks back. Are you listening

Jan 15, 2026 | Blog, Business Strategy, Digital Disruption, Innovation, Leadership

Last week a partner’s CEO emailed us a perfectly formatted RFP request, complete with the executive’s signature block and a cloud‑storage URL that looked legit.

I clicked the URL, watched it silently redirect, and was presented with a fake Microsoft 365 login page asking for my M365 credentials.

Before I acted, I messaged the CEO to verify; within minutes he replied affirmatively, then answered several follow up questions all of which were generated by an autonomous AI agent that was masquerading as him.

Trusting those responses, a colleague proceeded with logging into the site to retrieve the RFP PDF but the colleague who had logged in saw his account compromised.

A week later our colleague resent the same “RFP” email to me, I responded to him letting him know that his email account may have been compromised. He replied to my email insisting everything was fine and confirming that I should log in. Again it was not him but an autonomous AI agent that was masquerading as him.

What this means for senior leaders:

Cyber security and organizational security will be challenging in 2026 as more cyber hackers use AI agents to automate the social engineering process.

Zero‑trust controls must be enforced on every credential request, mandatory MFA is crucial, users should only have conditional access to core systems, and real‑time URL reputation checks are essential.

AI‑enabled phishing requires AI‑augmented defenses where organizations deploy behavioral analytics that flag anomalous redirects and synthetic language patterns in email replies.

Is your organization prepared to verify not just the sender, but the authenticity of every response?

Be safe out there!

#CyberSecurity #AgenticAI #ZeroTrust #DigitalTransformation #Leadership #CISOInsights #DearCEO #CEO

Dear CEO – Is AI Eroding Developer Skills & Job Satisfaction? A Look Inside Anthropic’s Own Experiment

Jan 14, 2026 | Agentic AI, AI, Blog, Business Strategy, Digital Disruption, Generative AI, Innovation, Intelligent Automation, Leadership

A fascinating, and potentially unsettling, new study from Anthropic reveals a complex reality about AI’s impact on the workforce.

While their engineers are leveraging Claude to boost productivity and automating up to 60% of tasks and enabling work that previously wouldn’t have happened.

Their concerns are emerging around deskilling, a loss of core competencies, and a diminished sense of professional fulfillment.

The data shows a trade-off: increased output at the potential cost of long-term expertise and job satisfaction.

Are we rushing into AI adoption without fully understanding the human cost?

It’s a critical moment for leaders to prioritize upskilling, foster a culture of continuous learning, and ensure AI augmentation, not replacement, remains the guiding principle. What safeguards are you implementing to mitigate these risks?

#AI #FutureofWork #DeveloperSkills #Deskilling #Leadership #DigitalTransformation #CEO #DearCEO

Dear CEO – AI vs Executive Reality – The Battle Your Company Can’t Afford to Lose

Jan 13, 2026 | AI, Blog, Business Strategy, Digital Disruption, Innovation, Intelligent Automation, Leadership

Many organizations say they want to be data-driven, yet their own executives quietly bury the very initiatives that would make it possible.

It’s a silent killer of progress.

We see it every day in our consulting work.

The promise of AI and data-driven decision-making often crashes into executive resistance, leaving brilliant work and wasted potential behind.

Here’s a story that illustrates this perfectly.

A cautionary tale of strong intentions, smart data science, and a fatal lack of buy-in.

I call it the “The Executive Kill Switch”.

In my last corporate role, I had a mandate to digitize and automate the business and help it become data-driven.

We built a strategy, secured funding, and got to work.

Every month the executive team battled a long list of operational issues.

And every executive meeting stalled on the same topic: overdue account receivables.

We proposed a machine learning model to predict which invoices would go overdue.

Our data scientist built it in six weeks with 85% accuracy (iteration 1).

We wrapped it in a simple Power BI dashboard that let leaders instantly see which invoices carried the highest risk.

We brought the model, dashboard, and new business workflow to the executive table.

And it flopped. Badly.

Why?

Because the executive team wasn’t digitally savvy.

They couldn’t see the value.

Yet the solution was built to save time, reduced write-offs, create value based outcomes and would mean we could stop acting as our clients’ bank.

In a true data-driven culture, this would’ve been embraced and operationalized immediately.

The irony is harsh: an executive team paralyzed by a recurring problem rejected the solution engineered to eliminate it.

This isn’t about technology; it’s about leadership and the gap between ambition and behavior.

What executives must start doing:

1. Data Literacy Bootcamp
Mandatory training on data fundamentals and AI applications. Non-negotiable.

2. Executive Data Champions
Empower leaders who genuinely support data initiatives.

3. Focus on Outcomes, Not Jargon
Frame solutions in terms of revenue, savings, and risk reduction.

4. Create a Safe Space for Failure
Encourage experimentation and recognize that setbacks are part of the journey.

Which camp is your organization in?

The innovators harnessing data, or the unwitting architects of its graveyard?

#DataDriven #Leadership #Innovation #AI #ExecutiveBuyIn #DataLiteracy #BusinessTransformation #DearCEO #CEO

Dear CEO – Boardroom Power‑Up – Should You Invite an Outside Tech Executive

Jan 12, 2026 | Agentic AI, AI, Blog, Business Strategy, Digital Disruption, Innovation, Leadership

If you think the board can survive without a dedicated technology voice, you’re already risking strategic blind spots. Paul Cuatrecasas shows that adding an external tech executive to the board can be a game‑changer if done right.

Pros of Adding an External Technology Executive:

Benefit	Why It Matters
Fresh Strategic Perspective – Brings up‑to‑date knowledge on AI, cloud, and emerging platforms that internal directors may lack.	Turns “tech hype” into actionable insight.
Accelerated Decision Speed – A tech‑savvy board member can cut the translation time between data scientists and senior leadership, shrinking product‑to‑market cycles from months to weeks.	Directly ties to the time‑to‑value compression Cuatrecasas highlights.
Network & Talent Magnetism – Their industry connections help attract top AI talent and forge strategic partnerships faster than a purely internal search.	Builds a competitive moat through ecosystem access.
Governance & Risk Oversight – Experienced in AI ethics, bias detection, and regulatory compliance, they can embed governance early, protecting brand equity.	Reduces the hidden cost of non‑compliance.

Cons / Risks to Watch:

Risk	Mitigation
Potential Conflict with CIO / CAIO – Overlap in responsibilities may create turf battles.	Clearly define scope: board member advises on strategy; CIO / CAIO executes.
Cultural Fit – An outsider may clash with existing board dynamics or corporate values.	Conduct a cultural‑fit interview and start with an advisory (non‑voting) role before full appointment.
Cost & Compensation – High‑profile tech execs command significant fees.	Tie compensation to measurable AI KPI outcomes (e.g., revenue uplift, risk reduction).
Information Leakage – Sensitive data could be exposed if confidentiality isn’t enforced.	Require NDAs and strict data‑access controls; limit exposure to strategic rather than operational details.

How to Make It Work (5‑Step Playbook):

Step	Action	Owner
Define the Role Clearly	Draft a charter that outlines strategic focus (AI roadmap, digital governance) and limits operational overlap.	CEO & Board Chair
Select the Right Candidate	Look for an executive with proven AI‑first leadership, board experience, and cultural alignment.	NED Search Committee
Integrate Into Existing Governance	Add the tech exec to the Technology & Innovation sub‑committee; ensure they sit alongside CIO/CAIO on quarterly reviews.	Board Secretary
Tie Compensation to Impact	Link a portion of fees to board‑level AI KPIs (e.g., % of projects delivering ROI, compliance audit scores).	CFO
Measure Success Quarterly	Track: Strategic Insight Frequency (how many tech‑driven decisions per quarter), Decision Speed Improvement, and Risk Mitigation Metrics. Report these in board minutes.	CHRO / CDO

If you could add one external voice to your board tomorrow such as AI strategy, cybersecurity, or digital ecosystems which would give you the biggest competitive edge?

Let’s discuss how that single addition can shift the entire trajectory of your organization.

#Leadership #Boardroom #AI #DigitalTransformation #CIO #CAIO #TechExecutive #Innovation #FutureOfWork #StrategicGovernance #CEO #DearCEO

Dear CEO – The AI Trust Deficit – Is Your HR Department Prepared

Jan 9, 2026 | Agentic AI, AI, Blog, Business Strategy, Digital Disruption, Generative AI, Innovation, Intelligent Automation, Leadership

Corporate Generative AI investment is exploding, yet a staggering 31% of workers fear job displacement and only 46% trust AI systems.

This “AI trust deficit” isn’t a tech problem it’s an HR leadership challenge.

Is it time that HR must reinvent itself, developing “AI fluency” and creating safe spaces for experimentation to bridge this gap?

Successful HR departments are acting as internal testbeds, solving employee problems (automating paperwork, streamlining tasks) to demonstrate AI’s value, rather than simply pushing adoption.

Are your CHROs leading with solutions, fostering peer-to-peer learning, and fundamentally rethinking HR technology to meet the speed of the AI era?

The stakes are high and lagging behind isn’t an option.

#AI #Leadership #HR #DigitalTransformation #EmployeeExperience #DearCEO #CEO

Dear CEO – Are You Ready for the AI Competency Test

Jan 8, 2026 | AI, Blog, Business Strategy, Digital Disruption, Generative AI, Innovation, Leadership

The message from the C-suite is clear: AI fluency isn’t optional anymore; it’s a core competency.

Companies like Accenture are actively “exiting” employees resistant to reskilling, while others are implementing mandatory AI usage mandates and ranking performance based on AI adoption.

This isn’t just about learning new tools; it’s a fundamental shift in how work is structured and valued, demanding a culture of continuous learning and a willingness to experiment—even at the executive level.

The data reveals a critical risk: organizations failing to embrace this transformation face obsolescence, while those who strategically integrate AI see increased efficiency and talent leverage.

Are you proactively assessing your workforce’s “AI will” or their willingness to adapt or are you risking a talent exodus and competitive disadvantage?

It’s time to move beyond pilot programs and ask: How do we build an organization where AI empowers everyone, not just a few?

#AILeadership #DigitalTransformation #FutureofWork #TalentManagement #AIStrategy #ExecutiveInsights #DearCEO #CEO