Thursday, June 11, 2026

Why culture matters more than you think, when complex tech goes wrong

After three decades in the technology industry, across countries and cultures, I’ve learned that the way people relate to hierarchy has a huge impact on successful delivery. Some cultures treat hierarchy as a gentle suggestion, others treat it like the cockpit of a 1970s jumbo jet, the pilot speaks, everyone else nods, and nobody mentions they thought they saw smoke coming from engine two!

Someone once told me there are more plane crashes in cultures where the hierarchy is more “power over” than flat – because the co-pilot is too scared to tell the pilot he made a mistake, this principle (if true) also applies to building software at scale.

Because enterprise technology is complex, mistakes will happen and should be expected to happen. We should be encouraged to talk about the mistakes as a learning exercise, just like the pilots landing any plane.

We should build stage-gates and checklists to mitigate all human brains because not one brain can see the whole enterprise, hence top-down/power-over control style leadership is a disaster. Don’t get me wrong, if a software engineer makes 80% mistakes then the mistake you have made is hiring the software engineer, but we should expect 20% mistakes within a framework of good design, clear direction and checks from experienced technical leaders.

It is well documented that both the healthcare and the airline industry understand that a blame culture in their complex environments drive mistakes underground. So pilots are encouraged to talk about their mistakes on landing and there is a curiosity in the culture.

Surguical precision 

You see surgeons running through their simple checklist before surgery – name (right patient phew), DOB (the correct John Smith -phew), left leg (imagine that conversation) etc, these are clever people with decades of training and it’s almost laughable the level of simplicity at which errors are made.  As Atul Gawande, a well-known surgeon, author and Harvard professor explains, “even the most expert professionals benefit from checklists” and separately goes onto say “the volume and complexity of our knowledge has exceeded our ability to consistently deliver it – correctly, safely or efficiently.”

Humans get tunnel vision under pressure – even brain surgeons and pilots -the opposite of what we need to solve complex problems. I wonder why these complex industries don’t talk to each other more. Why do power over leaders in technology think “another kick to the team and this project will speed up”.

Why doesn’t technology look to airlines and healthcare more to understand that it’s the pressure, pace and the culture that is contributing to many of the errors and overruns.

I know personally that for every red project I have picked up as head of delivery – and it must be in the 100s at this point, someone deep in the tech team knew 6 months before. And they were too unsure or too scared to say – often their thoughts are only half formed due to the pace and complexity…. It’s shards of light in the darkness…. It’s not complete enough to stick your hand up. No one will tell the big scary exec their fears in a culture which requires performative confidence and fast-paced cleverness, so everyone is smiling and nodding in update meetings.

Why is “I am not sure but something’s not right” from the mouth of a skilled professional batted into the long grass with an assumption that you need to be loud and confident before you put your hand up – by which time the problem has compounded and the project drifted further into the red.

Experienced ears will probe and listen for patterns of concern which are faint signals often verbally communicated in a culture of high trust and psychological safety. These experienced ears catch risk early then follow up with data that leads to certainty.

It takes all my mentoring and coaching to push against the culture and get that skilled professional to feel safe enough to tell me what their hunch is in these scenarios. It’s my listening skills that are at the forefront.

Hunches are good in complexity because you can move fast with them and follow them up with risk patterns from your experience or call on a trusted professional to double check. Your professional will do an analysis and produce data to prove or disprove your hunch, prepare to be wrong and try again – maybe it’s design, maybe it’s testing, maybe it’s the data – go get the skilled professionals and listen and observe, patterns will emerge.

Hunches talked about in a respectful way with experienced technology leaders in a flat hierarchy which sees leadership as one of the many professions, gets you to the problems and in turn through collaborative conversation gets you to specifics which help you solve problems.  

Once we find the problem we usually find two more, as James Reason writes in his book Human ErrorIn complex systems, failures are a result of latent conditions and active failures lining up”.

Error loop

In my experience what you discover is a scenario that shows multiple failures which point back to things that happened way before, for example high errors in testing are often faulty design decisions, if you just fix the individual test without tracing it right back you get stuck in a loop of fix something/break something else. Hence the need for some reflective thinking and lessons learnt – but that’s another story for another day!

Once we have identified our latent faults and current problems, we can then apply competency, and methods and check points and experience to dig our way out, the emotionally intelligent client facing “no” often is a guiding light too.

We need to create trust with our clients – by leading conversations about correct methods of say design while simultaneously creating a valuable commodity for our team – “time to think”. Pushing back on well-intentioned client requests (like a rushed design) is part of our job as technology leaders, we are selling an intelligent “yes” and “no” in equal measure.

Meanwhile millions of pounds are being screamed about, and the lawyer is reaching for the pen. Leadership in tech requires courage, resilience, calm and the role modelling of well-managed uncertainty, these behaviours are hugely important. That’s your job as a leader, find clever people and create good behaviours. Don’t be the cleverest person in the room with a fragile ego shouting for the screwdriver so you can fix all the problems.

When complex tech goes wrong, culture is often the context that lets latent errors click into failure and that’s a leadership problem.

Megan Owen has over 30 years of experience in the IT services industry, the last 2 positions as a C suite leader and Board member of financial services technology firms. She was chief delivery officer at SS&C, Global COO at Bravura Solutions and prior to that in leadership positions in Dell, Sopra Steria and Capgemini. She now offers consulting, coaching and advice to the technology industry through her own company: Megan and Partners.

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