What to Ask an AI Vendor Before You Sign Anything
AI vendors are pitching non-technical executives on commitments they can't fully evaluate. Here's the framework: what to ask, what to listen for, and what to slow down for before you sign.
You're in the room with an AI vendor. The deck is polished. The demo is compelling. The contract is on the table. And you have no one who can tell you whether any of it holds up on your actual data. Here's the framework.
#AIStrategy #TechLeadership #DigitalTransformation
07.03.2026 13:51
π 0
π 0
π¬ 0
π 0
How to Know If Your Engineering Team Is Underperforming When They Swear They're Not
When your tech team reports up with consistent optimism, it's rarely dishonesty. It's structure. Learn to read the signals your status reports won't show.
"Everything is on track."
That phrase has cost more companies more money than any failed product launch.
Your engineering team isn't lying. They just have no external benchmark and no one to hold them to one.
That's a leadership problem, not an engineering problem.
#FractionalCTO #TechLeadership
28.02.2026 12:56
π 0
π 0
π¬ 0
π 0
The Technology Due Diligence Mistake That Derails PE Value-Creation Plans - Fractional CTO
Private equity firms are not careless about technology diligence. Most processes include a serious look at architecture, core systems, cybersecurity posture,
Most PE tech diligence asks:
βIs the technology good enough?β
The question that actually determines outcomes:
βCan this organization deliver what the value-creation plan assumes?β
This is the technology due diligence mistake that shows up after close.
#PrivateEquity #M&A #TechDiligence
23.12.2025 11:56
π 0
π 0
π¬ 0
π 0
The Board-Level Liability Hidden in βWeβre Not a Tech Companyβ - Fractional CTO
βWeβre not a tech companyβ is usually said to keep the conversation grounded. We sell products. We deliver services. Technology supports the business, but it
Most companies donβt sell software.
Almost all companies depend on it.
Treating technology as βnon-coreβ doesnβt reduce risk. It just removes it from formal oversight.
Thatβs becoming a board-level liability.
#BoardGovernance #TechnologyRisk #CorporateGovernance #ExecutiveLeadership
20.12.2025 14:48
π 0
π 0
π¬ 0
π 0
In 2025, AI will elevate the CIO role. Hereβs why
In 2025, internal pressures within enterprises will accelerate the move to mandatory AI governance.
a recent Salesforce study found that more than half of CIOs (61%) feel that they are expected to know more about AI than they currently do and 9% think they know less about AI than their peers at other organizations. #cio #AI #governance #accountability
11.12.2024 04:28
π 0
π 0
π¬ 0
π 0
What to do when your CRM project fails
Many IT articles discuss how to avoid project failuresβ¦which is great, but according to industry analysts, at least one-third of CRM projects fall short. Here, weβre going to explore what to do if you...
Many IT articles discuss how to avoid project failuresβ¦which is great, but according to industry analysts, at least one-third of CRM projects fall short. Here, weβre going to explore what to do if youβre in that unlucky 33 percent. #CIO #CRM
29.11.2024 17:17
π 3
π 0
π¬ 0
π 0
From back office to boardroom: Say goodbye to the old CIO
Enterprises donβt need chief information officers anymoreβthey need chief intelligence officers.
In order to take advantage of GenAIβs potential, it is not a stretch to echo Darryl Maraj, CIO of TBC corporation, when he said that βbusiness strategy is technology strategy.β As a result, CIOs are no longer back-office custodiansβtheyβre trusted business partners. #CIO #GenAI #innovation
26.11.2024 13:17
π 0
π 0
π¬ 0
π 0
6 IT leadership organizations CIOs should consider joining
Leadership orgs help CIOs develop networks, gain peer insights, and stay on top of technology and management trends. Hereβs six groups that can help you become a smarter, more informed IT leader.
Leadership orgs help CIOs develop networks, gain peer insights, and stay on top of technology and management trends. Hereβs six groups that can help you become a smarter, more informed IT leader. #leadership #networking #leadershipgroups
25.11.2024 22:47
π 1
π 0
π¬ 0
π 0
Innovation Architects: How CIOs Build Business Breakthroughs
It behooves marketing and customer experience leaders to know whatβs on the minds of their technology leaders.
CIOs are no longer just managers of IT infrastructure. They are increasingly being called upon to drive innovation within their organizations. This role requires balancing leadership with collaboration, creating a culture of creativity and navigating the complexities of technological evolution. #CIO
24.11.2024 14:30
π 0
π 0
π¬ 0
π 0
CIO Challenges for 2024-2025, According to Hundreds of CIOs
Top CIO challenges hinge on AI, data, cybersecurity, business value and talent. Hereβs how to address them.
Eighty-one percent of boards have not made progress toward or achieved their digital business transformation goals. These underwhelming results leave many CIOs struggling to justify technology investments, even as more demands for technology increase across the business. #CIO #AI #cybersecurity
23.11.2024 15:30
π 2
π 1
π¬ 0
π 0
10 ways to kill your IT culture
From micromanaging to lacking a pragmatic vision that inspires change, IT leaders can inadvertently impact their ability to foster an IT culture primed to deliver business results.
In the study by Dale Carnegie, 73% of leaders felt their culture was very good or better concerning others being accountable, compared to 48% of team members. Additionally, 84% of leaders believed their organizations had strong teamwork compared to 60% of team members. #ITCulture #CIO #Teams
15.11.2024 02:32
π 1
π 0
π¬ 0
π 0
Stack Overflow Survey: 80% of developers are unhappy
This year, as expected, the main topics in the Stack Overflow survey were use of AI and dissatisfaction in the workplace.
Technical debt is the number one cause of developer frustration. Working with imperfect systems demoralizes programmers, making it difficult to do quality work. #programmers #stackoverflow #techdebt #AI
01.08.2024 12:50
π 1
π 1
π¬ 0
π 0
The Workforce Is Failing Women. Business Leaders Can Stop It www.wired.com/story/gender...
29.10.2023 13:49
π 0
π 0
π¬ 0
π 0
5 tips to unleash the full potential of your CIO www.linkedin.com/pulse/5-tips...
28.10.2023 14:00
π 0
π 0
π¬ 0
π 0
Moving to the Cloud: How to Lead a Cloud-First Technology Strategy www.workday.com/en-us/pages/...
27.10.2023 13:16
π 0
π 0
π¬ 0
π 0
5 IT leadership mistakes to avoid enterprisersproject.com/article/2021...
26.10.2023 12:24
π 0
π 0
π¬ 0
π 0
6 Tips for Becoming a Strategic CIO www.linkedin.com/pulse/6-tips...
25.10.2023 11:46
π 0
π 0
π¬ 0
π 0
IT leaders grapple with shadow AI www.cio.com/article/6477...
24.10.2023 22:24
π 0
π 0
π¬ 0
π 0
5 modern challenges in data integration and how CIOs can overcome them www.cio.com/article/6562...
23.10.2023 22:55
π 0
π 0
π¬ 0
π 0
Why we have too few women leaders www.youtube.com/watch?v=18uD...
21.10.2023 10:57
π 1
π 1
π¬ 0
π 0
3 key roles for driving digital success www.cio.com/article/6499...
20.10.2023 12:31
π 0
π 0
π¬ 0
π 0
How CIOs can encourage data-driven mindset enterprisersproject.com/article/2017...
19.10.2023 23:21
π 0
π 0
π¬ 0
π 0
The secrets of successful cloud-first strategies www.cio.com/article/3058...
19.10.2023 02:07
π 0
π 0
π¬ 0
π 0
Artificial Intelligence (AI) ethics: 5 questions CIOs should ask enterprisersproject.com/article/2020...
17.10.2023 11:56
π 0
π 0
π¬ 0
π 0
How to create a culture of innovation www.cio.com/article/2196...
16.10.2023 21:40
π 0
π 0
π¬ 0
π 0
5 Options for CIO Education www.informationweek.com/it-sectors/5...
15.10.2023 14:51
π 0
π 0
π¬ 0
π 0
How to use conflict to build stronger IT teams enterprisersproject.com/article/2020...
14.10.2023 22:23
π 0
π 0
π¬ 0
π 0
The CIOβs greatest recruitment challenge: Diversity in tech www.fastcompany.com/90687814/the...
13.10.2023 12:25
π 0
π 0
π¬ 0
π 0
Rethinking Hierarchy sloanreview.mit.edu/article/reth...
12.10.2023 14:37
π 0
π 0
π¬ 0
π 0