Why Tech Problems Are Often People Problems

One of the most rewarding parts of our work isn’t in the code or the contracts—it’s in the coaching. It’s where our “People First” value shows up most clearly. Because while tech may be the surface issue, the root cause—and solution—is often found in people and culture.

Just yesterday, we had conversations with:

  • 🧠 An experienced CIO with deep expertise in M&A and organisational dynamics
  • 🌐 A global tech firm embedding AI across their product suite
  • 💼 A Scale-Up COO navigating product-market fit and internal tech debt
  • 🚀 A new generation of VCs raising their first fund
  • 📈 A strategic buyer acquiring a smaller SaaS firm

Different sectors. Different stages. But one common theme kept emerging:

A tech problem is often a people problem. And almost always, a people problem impacts value.

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The CTO’s Journey: A Common Challenge in Diligence

In scale-ups, CTOs often find themselves in roles that outgrow their original job descriptions. They start as builders, become managers, and are suddenly expected to be strategic operators.

This transition isn’t easy.

When we conduct Tech Due Diligence, we frequently see:

  • Founder-CTOs struggling with delegation or team structure
  • Legacy systems held together by one key individual
  • Low maturity processes hidden behind high revenue growth
  • A lack of psychological safety, limiting learning or honest reporting

These aren’t just operational risks. They’re value risks. Culture—especially at the top—shapes how fast, how safely, and how scalably a firm can grow.

Start From the Top: Culture Drives Tech Maturity

The technical strategy might look sound on paper, but if the leadership culture is brittle, controlling, or unclear, the implementation falters. And the best tech stack in the world won’t save you from slow decision-making, siloed teams, or a lack of cross-functional trust.

That’s why we always begin with leadership. We offer psychological assessments for CTOs, CIOs, and Heads of Product to explore their operating style, communication preferences, and blockers.

These insights help:

  • Investors understand founder risk
  • Operators understand team dynamics
  • Buyers plan integration more effectively

What’s Next? CTO Coaching

We’ve created a practical guide outlining the common behavioural challenges that arise in scale-up CTO journeys—and how they show up in tech due diligence.

If you’re a CTO, CIO, or product leader, and you’re curious about how you show up as a leader—or how your habits may affect scale—drop us a DM. We’re offering a few free psychometric assessments as part of our leadership coaching programme.

Takeaway for Investors:

If you’re backing a tech-led firm, don’t just ask “Can they build?” Ask, “Can they scale—together?”

Because the difference between a £20M exit and a £200M one often isn’t technical. It’s cultural.

Picture of Hutton Henry
Hutton Henry
Hutton has worked with Private Equity Portfolio firms and Private Equity funds since 2015.Having previously worked in post-merger integration for large firms such as Ford and HP, Hutton understands the value of finding issues prior to M&A deals.He is currently the founder of Beyond M&A and provides technology due diligence for VC, PE and corporate investors, so they understand their technology risks before entering into a deal.

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