16 red flags. Plain English. Free to download.

Investing in technology is one of the highest-stakes decisions senior leaders navigate — and one where the specialist expertise inside their organisation is too rarely engaged early enough to make a difference.
Technology procurement is seldom an even-handed exchange. Suppliers are commercial entities looking to sell with minimal variation from their standard offering. Buyers are either scoping the exact problem they need to solve — or find themselves being presented with a solution they didn't ask for, by a supplier who has already decided they need it.
The Technology Supplier Red Flag Checklist gives you 16 plain-English warning signs to watch for across each stage of the supplier engagement journey — when you engage, while you evaluate, and before you sign.
16 important factors to consider across each stage of the supplier engagement journey:
Confirming that the procurement exercise is heading toward the right solution before substantial time and budget are committed.
The signals — in how a supplier presents themselves, structures their proposal, and responds to your questions — that reveal whether this is a supplier worth continuing with.
Example: Does the tender documentation accurately represent what your organisation is going to market for?
What to look for during evaluation — the patterns that emerge as the supplier engages with your specific needs and constraints.
The signals — in how a supplier responds to scrutiny, handles your internal review process, and manages the pace of the engagement — that reveal whether their proposal will stand up to examination.
Example: Have you included evaluation criteria to cover your cybersecurity and data privacy obligations?
Which protections must be in the contract — the specific clauses, commitments, and provisions that warrant careful review before your signature makes the agreement legally binding.
The signals — in how the supplier plans to protect the confidential and personal information your organisation deals with to ensure you meet your compliance obligations.
Example: Does the contract clearly articulate the supplier's responsibilities across the whole contract term?
The Checklist provides the supporting context for each question — what the answers might reveal and what to do if they surface any concerns.
Digital and data decisions are integral to how organisations operate today — and business leaders are increasingly being asked to own them, approve them, and answer for them — often without engaging the specialist expertise already inside their organisation that could protect them.
If you're a business owner, in the C-suite or leadership team and sign technology contracts — this Checklist is for you.
And if you work as an enterprise or solution architect, in information management, security, data, or governance, risk and compliance — and you support technology decisions made by business leaders — this is for you to use and share with the leaders you support.
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Plain English. No jargon. Free to download. No sales call. No diary slot. No waiting.
The Technology Supplier Red Flag Checklist is available to download to your device.
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We provide senior leaders and the information management and technology professionals who work alongside them with an independent framework comprising tools and guidance for navigating the full lifecycle of digital strategy and transformation decisions — from first awareness of need through delivery, operations, and eventual exit.
The framework includes plain-English tools, templates, structured methods, and supporting resources — designed for senior leaders and their teams to adopt and apply with confidence, not a consulting relationship that creates dependency.
The Technology Supplier Red Flag Checklist is one of the first instruments — free to use, free to share. Other instruments include the Technology Contract Essentials Toolkit for evaluating supplier contracts before signing, with further instruments planned, including a Privacy Statement Kit.
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