IT roadmap

A roadmap is a list of decisions with owners and dates, not a wish list.

A useful IT roadmap ties each change to a business reason, an owner, a cost and the decision needed, and plans around real support dates rather than rules of thumb. Here is what to include, the deadlines on the 2026-27 calendar, and a starter tool that drafts yours.

Support dates from Microsoft Learn, checked 31 October 2026.

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What to include
Real deadlines
Roadmap starter

Reviewed by Blake Bath, General Manager, on 31 October 2026.

A business owner and an IT consultant plan at a desk, the consultant marking a block on a colour-coded wall planner. — **12 January 2027**Windows Server 2016 extended support ends.

Six inputs

What goes into a roadmap.

Each line should trace back to one of these.

Business direction

Planned hires, sites, services and changes in how people work.

Reason stated
Timing
Owner

Roadmap starter

Draft your roadmap in a minute.

Tick what applies. You get a first draft in time order, with the hard deadlines and the decision each line needs.

Tick what applies to your business. You get a first-draft roadmap in time order, with the hard deadlines and the decision each line needs.

What applies to you? (pick all)

Your draft roadmap

3 items

Before February 2027

Windows Server 2016. Retire, move to the cloud or upgrade before 12 January 2027. Decision: Decide per server: retire, move or upgrade.
Staff using SMS codes for MFA. Move to passkeys or the Authenticator app before Microsoft retires SMS and voice MFA on 1 February 2027. Decision: Approve the rollout and help desk plan.

Next 6 to 12 months

Hiring in the next year. Licences, laptops and onboarding capacity for the new starters. Decision: Confirm headcount and timing.

Next: add an owner, an estimated cost and a target date to each line.

Build it with us

On the calendar

The fixed dates that belong on a 2026-27 roadmap.

Product or change	Date	What it means
Windows 10, Office 2016 and 2019, Exchange Server 2016 and 2019	Ended 14 October 2025	No security fixes without paid extensions where offered
Windows Server 2016	12 January 2027	Extended support ends
SMS and voice MFA in Entra ID	From 1 February 2027	Users relying only on SMS or voice are pushed to passkeys
SMS and voice MFA, Global Admins and external users	1 July 2027	Same change, later date

Not birthdays

Plan against support dates, not fixed replacement ages.

Check dates and eligibilityThe exact product, edition, end date and any paid extension.
Test what depends on itApps, exports, integrations and recovery before changing a critical system.
Record the reasonSupport gap, reliability, capacity or a workflow need, not a three-year rule.

Before approval

Show the full cost before asking for approval.

Existing operationsSupport, connectivity, subscriptions and renewals that continue regardless.
ImplementationConfiguration, migration, testing, training and process change.
Recurring changesWhat a project adds or removes from monthly costs, including overlap.
Exit and retirementExports, retained records, disposal and contract exit costs.
AssumptionsQuote validity and uncertainty written down, not a blanket contingency.

Our view

Start with the dates you can't move.

The most useful first roadmap is short: the deadlines you can't change, the risks you already know about, and the business plans that need IT ready in time. Server 2016 and the SMS MFA retirement are on most of our clients' lists right now.

Then we add costs, owners and decisions, and review it a month into delivery. A roadmap that gets revisited beats a perfect one that sits in a drawer.

How we work

Building a roadmap in five steps.

Step 1Priorities
Business direction, known issues, deadlines.
Step 2Baseline
Systems, support dates and dependencies.
Step 3Options and costs
With assumptions written down.
Step 4Approve
Priorities funded, deferrals recorded.
Step 5Review
A month in, then quarterly.

Related guides

Planning well. Risk, growth and lifecycle.

The inputs to a good roadmap.

Get help your way

Six ways to reach us. Pick whichever suits you.

Helpdesk hours are Monday to Friday, 8am to 5pm AEST. On Advantage and above, emergencies get a response within 1 hour and outages within 2, with 24/7 best-effort escalation.

Questions

What people ask about IT roadmaps.

What should an IT roadmap include?

The business reason for each change, the risk it addresses, an owner, timing, dependencies, cost and the decision needed. Note how you'll know it worked, and who owns anything deferred.

Does a roadmap have to cover three years?

No. Plan in detail for what you can fund and deliver, and keep a lighter longer view for support dates, renewals and big changes. Treat later estimates as assumptions to revisit.

Should we replace every laptop after three years?

Not by age alone. Check support status, reliability, what the apps need and what a failure would cost. Age is one input.

What hard deadlines should be on a 2026-27 roadmap?

Windows Server 2016 extended support ends 12 January 2027, and Microsoft retires SMS and voice MFA in Entra ID from 1 February 2027. Windows 10, Office 2016 and 2019, and Exchange Server 2016 and 2019 support already ended on 14 October 2025.

Does Windows 10 ESU restore normal support?

No. Extended Security Updates are temporary security fixes for eligible devices, not normal support. Use them to buy time for replacement, not to avoid it.

How often should we review the roadmap?

A month into delivery, then quarterly is a practical rhythm, and whenever business plans, costs or risks change.

Next step