The 'Done This Before' Trap: Why Narrow Experience is Costing You Enterprise Value

When I am advising a company or a board on a key hire, the first question I usually get is: “Have they done exactly this before?” It sounds like a sensible, risk-mitigating question; in reality, it is often the wrong one.

If you hire a team where everyone has “done this before,” you aren’t building a powerhouse; you are building a museum. You are hiring for yesterday’s solutions to tomorrow’s problems. While familiarity feels safe, it is the enemy of innovation-and in the current market, innovation is the primary driver of enterprise value.

A high-performing software team is not a monolith. It requires a delicate balance of three distinct personas to actually move the needle for a business.

First, you need the Institutional Anchors. These are the people who have been with the organisation long enough to know where the bodies are buried. They know which legacy systems are brittle and, more importantly, they know who to talk to in order to get things done.

Second, you need the Pitfall Spotters. These are the people who have done it elsewhere. They bring the “scar tissue” from previous roles; they know exactly how a specific migration can go wrong or why a certain architecture fails at scale.

But the third group is the most vital, and the one most often overlooked by CEOs: the Seasoned Generalists.

These are smart, experienced engineers who can communicate as well as they code. They might not know your specific tech stack or your niche industry, but they have a depth and breadth of experience that allows them to assimilate knowledge at a rate that would surprise most non-technical executives.

I recently hired a veteran software engineer into an AI engineering team. At the time, he knew next to nothing about Large Language Models or neural networks. On paper, a recruiter might have filtered him out in seconds. However, his impact was immediate and transformative.

The data scientists on the team were brilliant at research, but they were a thousand miles away from building a product. This engineer knew how to turn a fragile AI pipeline into a robust, production-ready piece of infrastructure. He understood how to make it cost-effective, observable, and secure; things the “AI experts” hadn’t even considered. He didn’t need to be an AI specialist to make the AI project a commercial success; he just needed to be a great engineer.

If you prioritise a candidate’s familiarity with a specific tool—be it Python, Node, or a particular cloud provider—over their ability to solve complex problems, you are hiring for the short term. A great engineer is a great engineer regardless of the language they are typing in.

For a CEO or Investor, the goal is to build a team that can adapt as the market shifts. That requires a mix of perspectives, not a group of people repeating the same playbook they used at their last three jobs. True enterprise value isn’t found in doing what has been done before; it’s found in the gaps between what your team knows and what they are capable of learning.