Ultimate CEO IT Handbook – 1,000+ pages of plain-English IT strategy and risk guidance for CEOs & owners.
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Digital Reference • Plain-English • CEO & Owner Focused

Ultimate CEO IT Handbook
1,000+ pages of board-ready clarity

A comprehensive, plain-English reference designed so a CEO or owner can finally see the full IT picture – strategy, risk, spend, vendors, cloud, cybersecurity and day-to-day realities – without needing to “speak tech.”

See What’s Inside Discuss Handbook + Advisory Options

Digital edition only. Can be purchased standalone or alongside any membership tier or engagement.

What the Handbook helps you do:
  • ✔ Understand IT spend, risk and vendors in business language.
  • ✔ Prepare board-ready stories about IT posture and priorities.
  • ✔ Spot vendor games, overspend and “nice to have” proposals.
  • ✔ Lead conversations with MSPs and internal IT with more control.

$495 USD one-time, digital edition.

Includes future minor updates for the current edition cycle.

Who the Handbook is written for

Built for:

  • ✔ CEOs, presidents and owners of 5–500 staff organizations.
  • ✔ Managing partners and MDs who sign off on IT spend.
  • ✔ Executives who must explain IT posture to a board, lender or investor.

Not aimed at:

  • Hands-on engineers looking for configuration guides.
  • Vendors seeking sales scripts or marketing collateral.

Format & access

The Handbook is delivered as a digital reference with internal navigation, designed to be searchable and skimmable. You can jump directly to topics such as:

  • ✔Cloud & cybersecurity
  • ✔IT spend & vendor management
  • ✔Backup, resilience & incident response
  • ✔AI, automation & data governance

It’s designed to be a long-term companion – something you return to before board meetings, renewals, acquisitions or major IT decisions.

What’s inside the 1,000+ pages

Strategy & Roadmap
  • ✔ How IT supports revenue, margin and risk.
  • ✔ Sequencing projects instead of chasing the latest trend.
  • ✔ Practical examples of “good enough” maturity for SMBs.
Cost, Vendors & Contracts
  • ✔ Mapping MSP, license and cloud spend in plain English.
  • ✔ Vendor games, traps and escalation strategies.
  • ✔ Renewal, negotiation and “walk-away” playbooks.
Risk, Cyber & Resilience
  • ✔ Plain-English explanation of modern cyber threats.
  • ✔ Minimum controls that move the needle for SMBs.
  • ✔ How to talk about risk with boards and insurers.

The Handbook also includes checklists, vendor questions, sample scorecards and talking points you can adapt for your own board packs and lender updates.

How CEOs typically use the Handbook

Before board / lender meetings

Quickly review the relevant sections and talking points to explain current posture, spending, and your near-term plan in a language non-technical directors will understand.

Before major IT purchases

Use the vendor questions, red-flag lists and examples to stress-test proposals and contracts before signing anything significant.

During internal reviews

Align your leadership team on expectations for backup, security, access, AI usage and more, using the Handbook as a neutral reference point.

Pricing & next steps

The Ultimate CEO IT Handbook is available as a single digital purchase. You can also bundle it with Growth Leadership, Executive Advisory or Counsel for a more guided experience.

$495 USD one-time

Includes digital access and minor updates for the current edition cycle.

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