The Toughest Pitch Is Often to Your Own Team

Psychoanalysis fo Tech Team

Yesterday, we ran a tech design session for a funded scale-up.
But before diving into architecture, APIs, or future-state diagrams—we did something different.

We started with psychoanalysis. Not therapy. Just a one-hour profiling of each team member’s natural strengths, workstyle, and decision-making approach.

The concept is to analyse the team’s strengths and psychological make-up before attending to the technical design.

What we uncovered in that hour changed the entire tone of the session.

What We Learned in 60 Minutes

With a quick diagnostic, we revealed three powerful traits within the leadership team:

  • 🧐 Analysis paralysis – A tendency to overthink or hesitate in moments of ambiguity
  • 🤲 Hands-on leadership – They lead by doing, not by directing from afar
  • 🤼 Polarised risk profiles – Half the team were bold risk-takers; the other half, deliberate risk mitigators

That last point introduced an obvious tension: when some want to move fast and break things, while others want to assess, contain, and plan—friction is inevitable.

But friction isn’t failure. It’s fuel—if we know how to use it.

From Awareness to Alignment

We then shifted into the tech design session. As expected, the group moved from reflection into action—and we saw their behavioural styles play out in real time.

The CEO, a quick-start, future-focused thinker, proposed a bold solution to a core platform challenge.
It made intuitive sense to him. He could see the downstream value clearly.

But for the more data-driven CxOs—those wired for risk mitigation—the connection between the proposed solution and the business case wasn’t immediately clear.

The moment of tension wasn’t about disagreement. It was about wiring.
And instead of brushing past it, the team paused.

We revisited the earlier insights and acknowledged:

  • The CEO wasn’t being reckless or egotistical—he was expressing his natural strength
  • The other CxOs weren’t being obstructionist—they were protecting the downside

That simple moment of awareness? It shifted the tone completely.

Why Internal Pitching Is Harder Than Investor Pitching

We often think of “pitching” as something we do to boards, buyers, or investors.
But the hardest pitch—the one we rarely prepare for—is the one inside our own leadership team.

That’s because internal audiences aren’t judging your deck.
They’re filtering your ideas through years of shared history, opposing instincts, and different tolerances for risk.

What makes internal buy-in easier?

  • Awareness of each other’s strengths
  • Language for how we process risk
  • Time to reframe the same vision in multiple ways

Which, in this case, took just one extra hour—and changed everything.

Final Thought: Teams Don’t Just Need Alignment on Strategy—They Need Alignment on How They Think

Design sessions often fail not because of poor ideas, but because of poor translation.
Your team may be smart, capable, and well-intentioned—but without a shared understanding of each other’s operating styles, even the best idea can die on the table.

We’ve seen it many times in tech due diligence.
Brilliant solutions rejected because of personality clashes, lack of trust, or misunderstanding.

But it doesn’t have to be this way.

One hour of self-awareness can unlock weeks of better collaboration.

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.

Take our FREE Scorecard to find out if your investment is at risk.

Discover the value of technology in your portfolio and target investments to gain more confidence and uncover potentially significant risks that could affect the value of a sale or an acquisition.

More Stories