Legacy everywhere: Why focussing on software is not enough to transform a company successfully

Philipp Engelmann
4 min readMay 24, 2020

Every company had or has legacy. Amazon had it and probably still has. Microsoft of course and a lot of other well-known companies as well. Legacy is not generally evil. In most cases it is the foundation the company has been built on. Legacy has paid the employees’ salaries or is still paying it. But: With legacy no company will stay in the market successfully on the long run. They will definitely be outperformed by competitors which have already replaced their legacy and are now able to build better digital products faster and in a better way.

Getting rid of legacy by transforming your company over and over again is crucial to stay ahead in the market.

So what is this “legacy”? When talking about legacy in product or tech, it is always referring to legacy software. An old software, system or application which cannot cope with the company and market needs anymore and therefore must be replaced.

Replacing legacy software mostly comes in hand with a big transformation project to get the company ready for a new era. Hence, the driver for this transformation is the need for a modern technology and to replace legacy code. But looking at this legacy problem more holistically, there is much more legacy to tackle:

Legacy software. Legacy mindset. Legacy structure.

“With legacy software there comes legacy structure and legacy mindset. In order to transform successfully, you have to change everything.”

— Me

Legacy Software: This is the starting point. The company recognizes that its old software has most likely a monolithic architecture which results in three major problems.

  1. It is not flexible enough to launch new features in a reasonable time which results in long time-to-market. Nothing you can live with in a VUCA (Volatility, Uncertainty, Complexity, Ambiguity) world.
  2. It is not scalable. Your business is growing, but your software cannot handle more users and more transactions.
  3. It is not stable. You have regular downtimes due to releases or peaks in sessions. Users do not like not reaching your site.

Legacy Structure: According to Conway’s Law, a company’s software is just mirroring its organizational structure. Therefore it is crucial to rethink your organizational structure when building a new tech stack. This needs power and commitment. Yes, you will disappoint or even lose people. But this is part of every company’s evolution. It will take some time until you get rewarded for this. But in the end, the company will become much stronger than it has ever been.

“Any organization that designs a system (defined broadly) will produce a design whose structure is a copy of the organization’s communication structure.”

— Melvin E. Conway

Legacy Mindset: There are endless articles about mindset in organizations. But one thing all agree on: It is the most important part. In all mature organizations there is legacy mindset, which has been developed over years. The sentence “We have always done it that way” is the most famous indicator for a legacy mindset. Changing this is a marathon, not a sprint. And changing this mindset needs to come from the very top through living, thinking and acting by example.

What I wanted to highlight is, that it is not only legacy software you are replacing. It is much more. You will definitely need to change your company’s way of thinking, its mindset. And with this change of mindset, an organizational redesign is crucial in order to build great digital products in a new and more agile way.

Short reminder how technological legacy looks like

Focusing on legacy software only will result in a vicious legacy circle

But what happens if companies are only focussed on replacing their software and not tackling the other two crucial work streams? It will be frustrating for everybody. On the one hand, you will have the tech team, which has to cope with legacy software, the legacy structure and mindset in other departments. This results in inefficient ways of building new software due to legacy structure. In most cases there is a lack of collaboration between departments caused by legacy mindset. On the other hand, most departments will try to protect their legacy kingdoms. This results in nontransparent communication and inefficient workflows. Though, legacy software will be replaced by a modern tech stack, digital products will only be average. The transformation project will probably be perceived as not very successful or even failed. These companies will then continue operating with a half modern tech stack. But if legacy mindset and legacy structure are not changed, the modern tech stack will quickly turn into legacy again.

Bottom Line

When thinking about replacing your legacy software, start with changing the company’s mindset first. And this needs to come from the top. If you have the right mindset, changing your company’s structure to facilitate an efficient way of building software is the next logical step. And then start thinking about your tech stack. Not the other way around!

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Philipp Engelmann

General Manager Omnichannel Business @ KaDeWe Group based in Berlin