Why People – Not Platforms – Can Derail Your Technology Due Diligence Assessment
The Hidden Risk in a Technology Due Diligence Assessment
Most technology due diligence assessments go one of two ways. Sometimes, the issues are clear from the start. You clock them in the first hour — a gut feeling, reinforced by a weak stance on cybersecurity, vague governance, or misalignment between tech and strategy.
That kind of project, ironically, is the easy one.
You know what’s wrong, and you can guide the investor (and sometimes the management team) to a clear outcome. Even if it’s not pretty, it’s clear.
But what about the projects where things just don’t add up — and no one can say why?
When Tech Doesn’t Make Sense, But It’s Not Broken
You look at the time and money spent. You compare that to the strategy and future roadmap. You ask structured questions.
Still, the story isn’t landing.
The data is there, but the logic chain isn’t. The management team can’t articulate the tech vision. And during the technology due diligence assessment, you’re left wondering whether this is actually a tech issue at all.
Spoiler: it isn’t.
Sitting on the Fence Isn’t Good Diligence
We’ve seen it before. We could deliver a long, jargon-filled report filled with grey areas, technical hedging, and “further clarification required.”
But that doesn’t help you, the investor, make a decision.
Not all tech issues have a binary yes/no answer. But technology due diligence assessments must still help you weigh risk, confidence, and post-investment readiness.
When the story lacks clarity, we don’t believe in hiding behind tech language. We get to the root of it.
It’s Not a Tech Problem. It’s a Pitch Problem.
Nine times out of ten, here’s what’s really going on:
- Poor materials – decks that assume too much, confuse more than they clarify, or require forensic effort from investors and assume the investors will read them
- No pitch narrative – the CTO talks tech, but not opportunity.
- Low conviction – stuck in ‘reality’ the team sounds like they’re explaining the past, not selling the future
And in a technology due diligence assessment, that becomes more than a communications issue. It becomes a capability red flag.
So it’s not surprising, that when this happens, Investors often ask us: Can this CTO step into the next phase of growth and embrace change?
How We Tackle It
In the lower-mid market, where we operate, growth doesn’t come from spreadsheets alone. It comes from people. That’s why our technology due diligence process is often collaborative, not just forensic.
Here’s how we help fix a pitch problem inside a tech assessment:
- We show what “good” looks like – clean, investor-grade examples of product roadmaps, architecture slides, and tech org charts
- We walk the team through structured Q&A – helping them build confidence and clarity
- We support the CTO’s pitch – connecting their expertise to the business value story
This isn’t about covering for teams. It’s about helping investors get a more accurate view of the potential — and helping teams bring their A-game.
From Tech Risk to People Opportunity
So yes, sometimes a red flag in a technology due diligence assessment looks like a tech issue — but it’s really a pitch issue, which is a people issue.
And the good news? Those are fixable.
A CTO who gets the right coaching and support can sharpen their pitch, reframe the roadmap, and create alignment. That doesn’t just reduce risk — it can increase valuation.
And that’s what good diligence should do.
