🐇 When Alice follows the white rabbit in Lewis Caroll’s 1885 novel ‘Alice in Wonderland’, she falls down a rabbit hole and enters into Wonderland, a complex, surreal world full of unexpected turns and challenges.

🧭 Since then the expression ‘avoiding rabbit holes’ is used to describe the practice of not getting side-tracked by fascinating but overly detailed, irrelevant, or too complex topics that deviate from the main objective.

When doing Technology Due Diligence (TDD) this common pitfall is always on my mind. TDD missions are high intensity 🔥 and must deliver impact in a limited timeframe. ⏳ There is no room for distraction.

So where to focus? As always in IT there is no binary answer, it depends. 🙂

Luckily, we do know what it depends on and where to find the guiding principles for our analysis of people, processes, and technology. Here are some of them:

🎯 First of all we have the investment thesis that provides the future expectations of the investor on the business (e.g. 10x increase in number of clients)

🚀 Next up are the key growth initiatives of the target company (e.g. Secret Project X)

⚖️ Then there are the specifics of the industry (e.g. compliance)

With this input we have the business context to

  • assess the initial holistic scan of team, strategy, architecture, security, AI, technical debt, operations, innovation, IP, etc., etc.
  • determine which deep dives are most important

In other words, it gives us the focus we need to avoid rabbit holes and to deliver the clarity and insight the investors need 🌟.