The importance of war stories

I’ve realised recently that some of the most useful things I’ve learnt in technology (and in life) didn’t come from a course, a framework or a certification. They came from war stories.

The project that went completely sideways. The production release that absolutely should have worked and absolutely did not. The client meeting where you knew within about three minutes that something had gone very wrong. The platform that looked beautiful on an architecture diagram but was practically unusable. The transformation programme with 400 slides, 12 work streams and no one quite able to explain what we were actually transforming.

The most important war story of all is life itself!

Anyone who has worked in technology for long enough has them. They’re becoming more important, not less. We have more information than we’ve ever had before, and sometimes it’s information we didn’t ask for.

I can ask AI to give me a data strategy. I can ask how to migrate a platform. I can generate an architecture diagram, delivery plan, backlog, RAID log or operating model before I’ve finished my first coffee. It can write me a shopping list, recipes, activities and trips.

Some of it will be really good. But knowing what should happen and knowing what actually happens are two very different things.

Enter war stories.

Experience gives you pattern recognition

When you’ve seen enough projects go wrong, you start noticing things earlier. Someone says, “We’ll sort the data quality later.” Or “We don’t need the business involved yet.” Or “We’ll migrate everything first and optimise afterwards.” Or “The documentation is basically up to date.”

None of those things automatically mean a programme is doomed. But experience gives you a radar you just don’t have the first time around. You recognise the conditions, you know which questions to ask and where to dig. And you learn that the thing everyone is currently worrying about isn’t usually the thing that’s going to hurt you.

That won’t come from a methodology or a textbook.

Good war stories matter too, but the market naturally pushes us towards the happy path: the successful transformation, the seamless migration, the impressive numbers at the end. That’s rarely where the value is. War stories are the counterpoint. What broke, what was underestimated, which assumption was completely wrong, and what happened when the main contact left the business. That’s the depth behind the experience, because it moves the conversation from what should work to what happened when it hit the fan.

War stories make us better consultants

There is a massive difference between telling a client what best practice says and being able to say: “We’ve seen this before.”

That isn’t about copying the answer from another organisation. Context matters far too much for that. It’s that you’ve seen the trade-offs play out. You’ve seen what happens when governance becomes so heavy that nobody can get anything done, and what happens when there is no governance at all. You’ve seen centralised teams become bottlenecks and decentralised teams create absolute chaos.

Those experiences change the advice you give. The answer becomes less “this is the textbook architecture” and more “here are the consequences of each option.”

We need to tell junior people the messy bits

I care about this bit the most. When experienced people only share the success stories, we do the people coming behind us a disservice. The polished case study is useful, but tell them what went wrong too. Tell them about the terrible decision you made and the thing you underestimated. Tell them why something that looked technically correct failed when humans actually started using it, and how you fixed it. Good delivery is not linear.

The best engineers, architects, product people and delivery leads I’ve worked with aren’t good because everything they’ve touched has gone perfectly. They’ve accumulated scar tissue. They’ve made mistakes, inherited other people’s mistakes, fixed things at ridiculous hours and had difficult conversations. Importantly, they’ve remembered it.

AI makes this even more important

AI can give us knowledge incredibly quickly, but it cannot give us lived experience. There is still something different about sitting in a room with someone who has been through five failed migrations and says: “Before you do anything else, check this.” That sentence might save you three months.

I’m very pro-AI. I use it constantly and I think it will fundamentally change how technology teams work. I don’t think it diminishes the value of experience. I think it increases it.

When everyone has access to the same knowledge, what sets you apart becomes knowing what matters, what doesn’t, when to challenge the textbook answer and when something just doesn’t smell right.

So tell your war stories, especially the embarrassing ones. They’re probably more valuable than the slide about everything that went perfectly.