How Confident Are You in Your Tech Roadmap?
Eighteen questions across six dimensions reveal whether your technology roadmap would survive a board's hardest questions — or read as a wish list.
- A scored profile across 6 dimensions — see exactly where you're strong and where the gaps are.
- Your biggest opportunities, mapped to specific next moves.
- A personalized video walkthrough from Shawn (optional) — a real read on your results.
Most technology roadmaps don't fail because the ideas are wrong — they fail because they can't survive scrutiny. A serious technology roadmap assessment looks past the list of initiatives at the things that actually determine whether the plan holds: how clearly it states where you're going, how tightly it maps to business outcomes, whether the timelines are achievable, whether the sequence respects dependencies, and whether you have the people, budget, and risk coverage to deliver it.
This free technology roadmap assessment scores your plan across six dimensions and returns a clear confidence profile in about six minutes. It's built from 27 years of technology leadership across Fortune 500 and growth-stage companies — the same lens a fractional CTO would bring to a roadmap review before a board meeting or funding decision.
What the technology roadmap assessment measures
Roadmap confidence isn't a single number — it's a profile. This technology roadmap assessment scores six dimensions independently so you can see exactly where the plan is strong and where it's exposed: Clarity & Vision (does the roadmap state where you're going and why), Business Alignment (does each item map to a real outcome), Feasibility (is the plan achievable as scoped), Prioritization (does the sequence reflect value and dependency), Resourcing (do you have the people and budget to deliver), and Risk & Dependencies (does the roadmap account for what could derail it). The final question maps the specific areas where your roadmap most needs work.
Why roadmap confidence matters before you commit
A roadmap is a promise — to a board, to investors, to a team that will spend the next year executing it. When that promise is built on unvalidated estimates, assumed dependencies, or capacity that doesn't exist, the gap surfaces as missed dates and lost credibility. The roadmaps that hold up treat confidence as a deliverable in its own right: they tie every initiative to an outcome, validate the hard items before committing, and sequence work by dependency rather than by whoever asked loudest. A confidence profile turns a plausible-looking plan into one you can defend in the room.
What you get at the end
You'll see an overall roadmap confidence score, a band that describes where you stand (from Wish List through Fundable & Defensible), a per-dimension breakdown, and a map of where your roadmap most needs work. From there you can request a personalized video walkthrough — a short, recorded read on your specific results and what a fractional CTO engagement would do to make your roadmap more defensible. No generic sales deck.
Frequently asked questions
What is a technology roadmap assessment?
A technology roadmap assessment is a structured evaluation of how confident and defensible a company's technology plan is. Rather than judging the ideas, it measures the things that decide whether a roadmap holds up: clarity of direction, alignment to business outcomes, feasibility, prioritization, resourcing, and risk coverage.
How long does the assessment take?
About six minutes. It's 18 scored questions across six dimensions plus a final question that maps where your roadmap most needs work. Your progress auto-saves, so you can leave and resume without losing answers.
Is the assessment free?
Yes. The technology roadmap assessment and your scored results are completely free. You can optionally request a personalized video walkthrough of your results, which is also free.
Who is this assessment for?
It's built for executives, founders, and technology leaders at mid-market and growth-stage companies who own a technology roadmap and want a clear-eyed read on whether it would survive a board's questions — and what to tighten if it wouldn't.
What happens after I get my score?
You'll see a full confidence profile with per-dimension scores and a map of where your roadmap most needs work. If you'd like, you can share a few details and receive a personalized video walkthrough explaining your results and what a fractional CTO would prioritize to make your roadmap more defensible.