Technical due diligence: the buyer takes on your problems too
Two sale processes, each requiring a month of preparation: the key people, licences, contracts and risks to document for the buyer’s review.
Roadmap & tradeoffs
Connect product priorities, technical constraints and business goals.
Intervention reportA roadmap the team no longer believes in needs more than another deadline.
I connect product choices, technical constraints and business goals so tradeoffs become explicit.
Chapter 1 · Intervention
How I prioritize and make trade-offs.
Translate constraints
I make technical dependencies, risks and costs visible in executive language.
Compare options
I lay out possible choices with their product, team, budget and timing impacts.
Align execution
I turn tradeoffs into a work sequence the team can understand.
Chapter 2 · Findings
When the product roadmap stops holding.
Priorities change often without a clear decision.
Discussions about technical debt and features stall without a decision on priorities.
Leadership lacks visibility on the cost of each option.
The team doubts whether the roadmap is feasible.
Chapter 3 · Inspection
What I look at in your roadmap.
The business goals behind product requests.
Technical dependencies that condition the roadmap.
Costs, risks and compromises of major options.
How decisions are made and communicated.
What you can expect
- Tradeoffs that leadership and the team can understand.
- A roadmap that accounts for technical constraints and available time.
- Fewer fragile promises and more durable decisions.
Chapter 4 · Answers
Roadmap and prioritization: your questions.
Can you join executive discussions?
Yes. This is often where a fractional CTO role creates the most value.
How do you arbitrate between technical debt and new features?
By being willing to say what stops. At Gridky, our CTO secured the CEO’s agreement to a month without new features, including for the priority client. We extended it to a month and a half based on the early results. I still consider that Drynuary the most profitable decision we made that year.
The roadmap keeps slipping: how do you find the cause?
I first separate what comes from technical debt, a lack of product focus, team dependencies or trade-offs left implicit. The Tech & Organization Diagnosis sets out this reading in 5 days, with a prioritized action plan.
Chapter 5 · Warning signs
Signs it is time.
The roadmap is accepted in meetings, then challenged during execution.
Important technical topics always come after features.
Nobody can explain what should be dropped or delayed.
Decisions happen under pressure or remain implicit.
Chapter 6 · Case files
In practice.
- 80%fewer production bugs, approximate estimate40,000 properties, 12 tax regimes, banking-grade security. When the machine has to be reliable before it can be smart. Gridky Fintech & Real Estate
- 3,000+audits completed for 200+ clientsHundreds of companies steering their accessibility strategy from a single platform. The management platform adopted by the leading digital accessibility organisations. IpedisConnect™ Platform & Product
Next
Does this sound familiar?
A tool to prepare the conversation, a diagnosis to understand the context, and support to take action.
Latest articles
Feature freeze: why I still stand by Gridky’s Drynuary
Hundreds of Slack exceptions every morning, a team split in two, a priority client waiting. Then a month without a single new feature, negotiated with the CEO. I still stand by it: in my view, the most profitable decision of the year.