Technology Leadership Assessment

Discovery

Establish what is true, and get evidence moving before it becomes the critical path.

• Kickoff call, 60 to 90 minutes, with the sponsor and whoever owns technology today, whether that is an internal manager or your provider's account manager.
• Scope agreed in writing: which entities and sites are in, which systems are out, who gets interviewed, and what finished means. Scope that lives in an email is scope that gets argued about at the end.
• Your workspace opens. Participants are invited, and each of the eight domains is assigned as advisor-led or client-led so nobody is waiting on anybody.
• The evidence request list is issued, every item carrying a stated purpose and a named owner.

• Five to eight conversations, 45 minutes each: the sponsor, your operations lead, your IT manager or provider account manager, finance for the spend picture, and one or two functional leads who use the systems every day.
• The questionnaire opens in parallel, so domain owners can start while interviews are still running.

Identity

Sign-in export from your identity provider. Read and aggregated in the browser, never uploaded.

Endpoints

Device inventory export: operating system, version, encryption status, last seen.

Software

Licence entitlement against licence assignment.

Spend

Twelve months of technology spend from the ledger, or accounts payable by vendor.

Contracts

Your provider agreement, key software agreements, and any master services agreements.

Infrastructure

Network documentation, backup configuration, and the date of the last restore test.

Insurance

The cyber policy schedule and the application that was submitted for it.

Governance

Security, access, acceptable use and incident response policies; the technology org chart; any current roadmap or budget.

Analysis

Turn evidence into scored findings you can argue with.

• Outstanding requests chased. The workspace tracks what is open and who holds it, so nothing depends on somebody remembering.
• Exports parsed into computed facts: multi-factor coverage and its exceptions, dormant and orphaned accounts, sign-ins from unexpected countries, endpoint support status and encryption coverage, licences bought against licences assigned, and spend by vendor with duplicates caught under two different names.
• Contract terms extracted: term, renewal date, notice window, and price escalators.
• The instrument completed: around 150 questions across eight domains and forty capability areas, each answer anchored to a described maturity level rather than a gut score.

• Weighted scores computed with the derivation visible, so you can see which answers produced each number.
• Benchmarked against the peer set for your size and industry.
• Findings drafted against the evidence, then read and edited by a person before any of it becomes a deliverable.
• Risk register built, ranked by business impact, every entry carrying a named owner and a review date.
• Vendor and contract register built with renewal dates, notice windows, and renegotiation targets.

Roadmap and readout

Convert findings into decisions somebody owns.

• Sequenced by return and dependency, not by vendor convenience.
• Three to five meaningful moves, not a forty-item wishlist.
• Each one carries an owner, a budget range, and the value driver it moves: revenue, margin, risk, or valuation.
• Quick wins separated from structural work, so the first ninety days are obvious.
• The pre-read goes out 48 hours before the session.

• A 90-minute working session with your executive team: the scorecard, the top risks, the spend findings, and the roadmap.
• Built to be argued with rather than presented at. Challenge in the room is the point.
• Decisions captured during the session: accepted, deferred, or owned by name.

• Six deliverables issued: scorecard, risk register, spend analysis, vendor and contract review, twelve-month roadmap, and executive summary.
• The workspace stays live, so the registers stay current instead of ageing into a PDF.
• The next step is recorded either way: a retainer, execution with your own team, or nothing at all.