IT Projects for Leadership: 10 Questions Before You Sign

The board approved the budget. The IT director picked a vendor with a glossy portfolio. Contract signed. Six months later the CEO gets a change order for +40%, deadlines slip, “another module surfaced,” and the business sponsor says: “We never asked for this.”

That is a typical failure not at code level but at agreements before kickoff. Below — ten questions leadership (CEO, CFO, COO, board) should ask before signing — no Kafka, no Kubernetes, no noise that drowns board meetings.

Why “let IT handle it” is not enough

Your CTO covers technical depth. The contract fixes money, timelines and accountability for business outcome. If the spec says “build a platform” instead of “cut approval cycle from 12 to 5 days” — conflict in six months is guaranteed.

Leadership does not pick PostgreSQL vs MongoDB. It sets the frame in which internal or vendor engineering makes decisions.

10 questions before signing

1. What measurable outcome in money or time in 90 days?

Not “launch the system,” but:

• −40% contract approval time;
• −2 unplanned line downtime incidents per quarter (see downtime cost);
• first paying customer on a new SaaS module.

Without a number the project becomes an endless “pilot” — fine for reports, useless for P&L.

2. Who is the business product owner — not only IT?

Name a sponsor: COO, commercial director, plant manager — whoever owns the KPI that changes after go-live. IT without a business owner ships “working software” the shop floor bypasses with Excel.

Critical at digitalization start — see CEO digitalization checklist.

3. What is in scope — and explicitly out of scope?

Contract appendix: modules, integrations, roles. Separately — exclusions: “10 years of mail archive migration,” “on-site training for 500 users,” “custom 1C reports.” “Out of scope” cuts +30–50% change orders.

4. Fixed Price, T&M or milestones — and how price changes?

Model	When it fits	Buyer risk
Fixed Price	Pilot with clear spec after discovery	Hidden “not in estimate”
Time & Material	Outstaff, evolving product	Hour inflation without transparency
Milestones	Turnkey: discovery → MVP → production	Stall between phases without acceptance criteria

Contract: rates, budget cap per phase, change request procedure (response time, repricing formula).

5. Who owns code, data and access?

Minimum before advance payment:

• repository in your Git org;
• secrets and cloud — your accounts or handover per acceptance act;
• exclusive rights on custom work — yours; OSS licenses listed in appendix.

“We will hand over code at the end” is a red flag. Handover — per sprint.

6. Who exactly is on the vendor team — and if a key person leaves?

Named roles (architect, tech lead), not only “team of 8.” Replacement of Senior within N days, onboarding at vendor cost. For outstaff — squad vs body shop.

7. How do we see progress every week?

• demo of working software (not mockups);
• burndown or closed tasks in your Jira/Linear;
• budget actual vs plan;
• top 3 risks with owners and dates.

“90% done” without a demo — pause the next payment tranche.

8. SLA, penalties and symmetric obligations

If the vendor faces delay penalties — the buyer must deliver access, approvals and change-request decisions on time. Otherwise disputes become “you did not give VPN / sign the mockup.”

For production systems, tie reliability to money — error budget idea from SRE for business.

9. ERP / 1C / AD integrations — who pays for surprises?

Spec: entities, master system, test environment, your-side owner. “We will integrate later” without budget — classic +6–12 weeks overrun.

10. How to stop the project without losing everything?

• what is handed over on termination at any stage (code, docs, access);
• payment for completed and accepted milestones only;
• handover window in days, not months.

Reduces “hostage code” risk and improves leverage if you switch vendors.

Red flags in negotiations

Budget anchors for CFO conversation

• Discovery + architecture — 5–10 days, from $1,000
• Single-process pilot — 2–4 months, from $10k
• Senior outstaff — from $50/h, packages from $4,800/mo — prices, hire a developer
• Load testing before peak — from $1,000 — service

Bottom line for leadership

A good IT contract for the board is not 40 pages of stack details. It is measurable outcome, business owner, transparent scope, your Git and a clear exit.

Discuss your case before signing — 2-minute estimate, turnkey development or talk to an engineer.

Related: digitalization checklist for CEOs, corporate AI Plan B, when Excel stops scaling.