In January 2019, IDC Canada and ITAC hosted a tech trends breakfast in Toronto focused on intelligent automation, AI and augmented reality interacting with employees, the future workforce, and how business and IT leaders would adapt as machines and humans increasingly worked together.
I have been part of many IT executive communities since 1983.
In 2018, I interviewed Kevin Peesker — then President of Microsoft Canada — at the Activate Digital Conference in Guelph about where digital evolution was heading in Canada, the responsibility organizations have to evolve both technologically and culturally, and what it really means to be a technology partner rather than a check-the-box supplier. I have conducted similar conversations with senior IT executives across Canada for four decades, through my work with ITAC, CATA, and the technology organizations that were shaping the enterprise technology agenda before most of the platforms now being called AI-enabled even existed.
What I have observed across four decades — and what the Procurement Insights archive has documented for the last 18 years — is one consistent pattern: the gap between what capable technology recommends and what organizations are actually designed to do with that recommendation.
What IT leaders were asking in 2019
The 2019 IDC/ITAC agenda asked the right questions. Which technologies will significantly change workforce needs? How will AI and intelligent machines interact with employees? How will business and IT leaders adapt? How does this shift the role of technology vendors and consultants?
At their core, these are governance questions dressed in technology language: is the organization designed to absorb what the technology is about to produce?
It was the right question in 1998 at Canada’s Department of National Defence, in 2007 when the Procurement Insights archive began documenting implementation failures, and in 2019 at that IDC/ITAC breakfast. It is still the right question now.
In 1998, a self-learning procurement system at the DND raised delivery performance from 51% to 97.3% in three months — not because the technology was sophisticated, but because the governance architecture, decision authority, and process integrity were aligned before deployment. The diagnostic layer arrived before the commitment was made.
The IT community in 2019 was asking the question. The structured readiness diagnostic that honestly answers it was not consistently applied.
What we are still asking in 2026
Seven years later, the questions sound remarkably similar — only the vendor names, analyst reports, and platform capabilities have changed. Today’s AI-enabled systems produce far more confident, fluent outputs than anything available in 2019. Yet organizations are still struggling to convert those outputs into sustained outcomes.
Both communities assume the answer lives in better platforms and better evaluation frameworks. The evidence says it lives in a readiness diagnostic they have never consistently applied.
This is not a criticism of either community. It is a structural observation about where the diagnostic layer has been consistently absent — not because the questions were wrong, but because the evaluation frameworks available to answer them were optimized toward deployment rather than readiness.
ERP, eProcurement, P2P, analytics, cloud, AI — different platforms, same gap, same post-mortem.
What has changed — and what has not
What has changed is the sophistication of the technology. The closed-frame AI architecture inside today’s leading platforms is genuinely more capable than anything that existed in 2019. The confident, fluent, coherent outputs these systems produce are more convincing than any previous generation — which makes the governance gap harder to see, not easier.
In 2018, Kevin Peesker made a point that has stayed with me: organizations that treat themselves as check-the-box service providers will need to find new careers — because customers know what they want to accomplish, and what they are looking for is a genuine partner with organizational depth, not a product list.
That observation applies with equal force to the AI platforms now being evaluated across every enterprise technology budget. The platform is not the partner. The platform is the capability. The partner is the independent diagnostic layer that tells you whether your organization can actually execute what the platform is capable of producing — before the capital is committed, not after the implementation fails.
The one consistent variable that changed outcomes
Across forty-three years of watching technology cycles, the initiatives that delivered on their business cases shared one trait: an explicit assessment, upfront, of whether the organization’s governance architecture, decision authority, and process integrity were designed for the real conditions the technology was about to create.
Across four decades, one pattern has remained constant: the diagnostic layer never arrived before the commitment was made.
That diagnostic has a name now. It is called Phase 0™. It is grounded in principles first validated in live operations in 1998 and refined through 18 years of longitudinal research across multiple technology eras. It is not a procurement tool. It is not an IT tool. It sits above your current evaluation framework — which is precisely where it needs to sit to produce an honest answer.
What this means for CIOs and CFOs now
The Procurement Insights archive is expanding. Beginning now, dedicated sections for CIOs and CFOs will surface the governance and readiness research that has always been relevant to capital allocation and technology decisions — informed by four decades inside the IT executive community.
The questions IDC and ITAC were asking in 2019 were good questions. The conversation Kevin Peesker and I had in 2018 about genuine partnership versus check-the-box service providers was the right conversation. They deserve answers grounded in organizational reality, not just the next platform’s capability claims.
That answer exists. It has existed since 1998. And it is now being offered directly to the leaders who hold the budget authority and governance accountability.
If you sign off on architecture and capital, this is your diagnostic — not procurement’s.
The Procurement Insights archive contains 3,300+ published documents spanning 18 years of independently produced, timestamped research — zero vendor sponsorships, zero paid analyst relationships. Phase 0™ is the organizational readiness diagnostic that precedes all technology commitments. RAM 2025™ is the multimodel validation framework that cross-validates all major Hansen Models™ assessments before publication.
Jon Hansen interviewed Kevin Peesker, then President of Microsoft Canada, at the Activate Digital 2018 Conference in Guelph. The full discussion is available at longviewsystems.com.
If you have an active or upcoming AI or technology initiative, this is the moment to determine whether your organization can act on what it will produce — before capital is committed.
Book a 30-Minute Readiness Conversation with Jon Hansen — a direct, no-sales-pitch discussion about where your organization sits on the readiness spectrum and whether Phase 0™ is the right next step.
→ Book your 30-Minute Readiness Conversation
hansenprocurement.com
-30-
Procurement Insights 
The Questions IT Leaders Were Asking in 2019 Are the Same Questions We Are Still Asking in 2026. Neither Community Has the Answer It Thinks It Has.
Posted on March 28, 2026
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In January 2019, IDC Canada and ITAC hosted a tech trends breakfast in Toronto focused on intelligent automation, AI and augmented reality interacting with employees, the future workforce, and how business and IT leaders would adapt as machines and humans increasingly worked together.
I have been part of many IT executive communities since 1983.
In 2018, I interviewed Kevin Peesker — then President of Microsoft Canada — at the Activate Digital Conference in Guelph about where digital evolution was heading in Canada, the responsibility organizations have to evolve both technologically and culturally, and what it really means to be a technology partner rather than a check-the-box supplier. I have conducted similar conversations with senior IT executives across Canada for four decades, through my work with ITAC, CATA, and the technology organizations that were shaping the enterprise technology agenda before most of the platforms now being called AI-enabled even existed.
What I have observed across four decades — and what the Procurement Insights archive has documented for the last 18 years — is one consistent pattern: the gap between what capable technology recommends and what organizations are actually designed to do with that recommendation.
What IT leaders were asking in 2019
The 2019 IDC/ITAC agenda asked the right questions. Which technologies will significantly change workforce needs? How will AI and intelligent machines interact with employees? How will business and IT leaders adapt? How does this shift the role of technology vendors and consultants?
At their core, these are governance questions dressed in technology language: is the organization designed to absorb what the technology is about to produce?
It was the right question in 1998 at Canada’s Department of National Defence, in 2007 when the Procurement Insights archive began documenting implementation failures, and in 2019 at that IDC/ITAC breakfast. It is still the right question now.
In 1998, a self-learning procurement system at the DND raised delivery performance from 51% to 97.3% in three months — not because the technology was sophisticated, but because the governance architecture, decision authority, and process integrity were aligned before deployment. The diagnostic layer arrived before the commitment was made.
The IT community in 2019 was asking the question. The structured readiness diagnostic that honestly answers it was not consistently applied.
What we are still asking in 2026
Seven years later, the questions sound remarkably similar — only the vendor names, analyst reports, and platform capabilities have changed. Today’s AI-enabled systems produce far more confident, fluent outputs than anything available in 2019. Yet organizations are still struggling to convert those outputs into sustained outcomes.
Both communities assume the answer lives in better platforms and better evaluation frameworks. The evidence says it lives in a readiness diagnostic they have never consistently applied.
This is not a criticism of either community. It is a structural observation about where the diagnostic layer has been consistently absent — not because the questions were wrong, but because the evaluation frameworks available to answer them were optimized toward deployment rather than readiness.
ERP, eProcurement, P2P, analytics, cloud, AI — different platforms, same gap, same post-mortem.
What has changed — and what has not
What has changed is the sophistication of the technology. The closed-frame AI architecture inside today’s leading platforms is genuinely more capable than anything that existed in 2019. The confident, fluent, coherent outputs these systems produce are more convincing than any previous generation — which makes the governance gap harder to see, not easier.
In 2018, Kevin Peesker made a point that has stayed with me: organizations that treat themselves as check-the-box service providers will need to find new careers — because customers know what they want to accomplish, and what they are looking for is a genuine partner with organizational depth, not a product list.
That observation applies with equal force to the AI platforms now being evaluated across every enterprise technology budget. The platform is not the partner. The platform is the capability. The partner is the independent diagnostic layer that tells you whether your organization can actually execute what the platform is capable of producing — before the capital is committed, not after the implementation fails.
The one consistent variable that changed outcomes
Across forty-three years of watching technology cycles, the initiatives that delivered on their business cases shared one trait: an explicit assessment, upfront, of whether the organization’s governance architecture, decision authority, and process integrity were designed for the real conditions the technology was about to create.
Across four decades, one pattern has remained constant: the diagnostic layer never arrived before the commitment was made.
That diagnostic has a name now. It is called Phase 0™. It is grounded in principles first validated in live operations in 1998 and refined through 18 years of longitudinal research across multiple technology eras. It is not a procurement tool. It is not an IT tool. It sits above your current evaluation framework — which is precisely where it needs to sit to produce an honest answer.
What this means for CIOs and CFOs now
The Procurement Insights archive is expanding. Beginning now, dedicated sections for CIOs and CFOs will surface the governance and readiness research that has always been relevant to capital allocation and technology decisions — informed by four decades inside the IT executive community.
The questions IDC and ITAC were asking in 2019 were good questions. The conversation Kevin Peesker and I had in 2018 about genuine partnership versus check-the-box service providers was the right conversation. They deserve answers grounded in organizational reality, not just the next platform’s capability claims.
That answer exists. It has existed since 1998. And it is now being offered directly to the leaders who hold the budget authority and governance accountability.
If you sign off on architecture and capital, this is your diagnostic — not procurement’s.
The Procurement Insights archive contains 3,300+ published documents spanning 18 years of independently produced, timestamped research — zero vendor sponsorships, zero paid analyst relationships. Phase 0™ is the organizational readiness diagnostic that precedes all technology commitments. RAM 2025™ is the multimodel validation framework that cross-validates all major Hansen Models™ assessments before publication.
Jon Hansen interviewed Kevin Peesker, then President of Microsoft Canada, at the Activate Digital 2018 Conference in Guelph. The full discussion is available at longviewsystems.com.
If you have an active or upcoming AI or technology initiative, this is the moment to determine whether your organization can act on what it will produce — before capital is committed.
Book a 30-Minute Readiness Conversation with Jon Hansen — a direct, no-sales-pitch discussion about where your organization sits on the readiness spectrum and whether Phase 0™ is the right next step.
→ Book your 30-Minute Readiness Conversation
hansenprocurement.com
-30-
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