BizTools · Technology Toolbox · Planning Template
Technology
Roadmap Planner
Sequence the next 12–24 months of tech work — by priority and business impact, not by whoever complained the loudest.
Most small and mid-size businesses manage technology reactively — buying tools when the pain gets unbearable, replacing things in a crisis, and finding integration problems only after the contract's signed. A roadmap changes that. It gives you a 12–24 month view of every tech initiative, ordered by business impact. This planner walks you through it in order: inventory your gaps → score and prioritize → sequence into four horizons → budget → assign owners → build one visual roadmap your whole team commits to.
1
Complete in order
Sections build on each other. Prioritizing (C) needs your full list (B). Don't jump to the grid before scoring.
2
Involve department leads
Each leader knows their team's tech pain and capacity. Budget 60–90 min together on Sections B and C.
3
Be ruthless about priorities
A roadmap with 20 "high priority" items is a wish list. Force-rank. The first 3–5 need a clear business case.
4
Review quarterly
Conditions change. Block 2 hours per quarter to review progress and re-prioritize the next horizon.
A
Current State Snapshot
Where does your tech stack stand today?
| Function area | Current tools | Top pain point today | Health · 1 Poor → 5 Great |
TIPA function rated 1–2 is a candidate for an H1 initiative. Be honest — this snapshot is what your roadmap is built to fix.
B
Initiative Inventory
List every tech initiative on your radar — add, upgrade, replace, integrate, retire, fix.
Capture everything first — no filtering yet. Include both problems to solve and opportunities to pursue. You'll score and prioritize in Section C.
| # | Initiative / tool name | Type | Function area | Problem it solves | Requested by | Benefit |
TIPAim for 8–15 initiatives. More than 20 signals scope creep — group or defer the smallest ones.
C
Priority Scoring Matrix
Let the data sequence your roadmap — not politics.
Scoring guide · rate each 1–5
Impact ×2
5 Critical revenue, retention, or compliance driver
3 Meaningful efficiency gain
1 Nice to have
Urgency
5 Causing active pain or risk right now
3 Growing friction
1 Can wait 18+ months
Ease
5 Simple, low-risk, quick to deploy
3 Moderate effort
1 Complex, high-risk
Dependency
5 Others can't start without this
3 Enables 1–2 others
1 Standalone
Cost-to-Value
5 High ROI or low cost, clear payback
3 Reasonable
1 High cost, unclear return
| # | Initiative |
Impact
×2 | Urg. | Ease | Dep. | C-V |
Total
/30 | Rank | Horizon |
TIPImpact is weighted ×2 — business value should always outrank convenience. Totals and rank update live as you score. If two items tie, Urgency breaks the tie.
D
Visual Roadmap Grid
Your 12–24 month view — one initiative per row, sequenced by horizon.
Click a month cell to mark progress. Each click cycles: Start ■ → Active → Complete ✓ → clear. Add an owner and budget for each row.
■Start month
Active / in progress
✓Complete
Click any cell to cycle through states.
E
Budget Planner
Estimate costs by horizon and category — before the vendor conversations start.
License cost alone is never the full cost. Estimate license, setup, training, and integration separately. Row totals, horizon subtotals, and the grand total calculate automatically.
| Initiative |
License / sub
($/yr) | Setup / impl. | Training | Integrations | Other | Total est. |
TIPPair this with the TCO Calculator in the 7-Step Tech Decision Series for a full total-cost-of-ownership picture per initiative.
F
Initiative Detail Cards
One card per H1 initiative — fill before execution begins.
TIPOnly fill detail cards for H1 (Now) initiatives. H2–H4 get a card when they move into the active horizon.
G
Quarterly Review Log
Use this at the start of each quarter to keep your roadmap on course.
Run this review in 90 minutes or less. Same attendees each time: owner + department leads + whoever holds the tech budget. Block it on the calendar now.
Roadmap Health Indicators · answer after each quarterly review
TIP3+ RED indicators? Pause new initiatives and schedule a roadmap reset session before the next quarter begins.
✓
Summary & Roadmap at a Glance
Confirm your roadmap is complete and ready to share with your team.
Roadmap at a Glance · your top initiatives per horizon
Key Commitments · what leadership is committing to
NEXT →
Ready to act on your H1 initiatives?
Use the 7-Step Tech Decision Series. For each H1 initiative, run the Business Case One-Pager, TCO Calculator, and Fit-First Vendor Scorecard before you select a vendor.
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