Steve Webster on caring deeply, changing direction and making room to think.Steve arrived on The Struggle Bus with the after-effects of a boxing session. Twenty-seven years in ecommerce had apparently done little for his flexibility. There was a bruise to add to the collection, and a joke ready to go with it.
That is a decent introduction to Steve. He has a way of acknowledging the knock without allowing it to take over the room.
I had enjoyed speaking with him before we recorded. He is deliberate, witty and able to move between the detail of an operation and the motives of the people directing it. In this conversation, I wanted to understand where that manner came from.
His career has crossed categories and countries. There was a business he built with a partner, developing luxury toiletries from the first conversation through fragrances, manufacturing, packaging and branding. They had been trading for roughly three months when they lost their funding and had to wind up.
It is easy to race past that sentence on the way to the next role. We do it all the time in professional biographies. A business becomes a line in a career, and the work of imagining it, building it and then closing it disappears between the commas.
Steve tells the story plainly. When I call it a badge of honour, he says he has a couple of those badges now. The humour lets the fact sit in the conversation. It does not require an inspirational speech to make it respectable.
Later, I ask him about his calmness. He talks about a brief time in the army after university, a career he had wanted, and the value of keeping your head when there is adversity. Maintaining a view of what needs to happen gives you a chance of finding a workable solution.
Then he says something that matters more to me than the career chronology. His calm has sometimes been read as a lack of care or passion. He says that is a mistake. He does care. He takes things home. Performance, team development and the wellbeing of the people around him can tie him in knots.
The quiet person can still be carrying plenty.
That is what I kept hearing as the conversation moved back into ecommerce. Behind his frustration with noise and shiny tools is a concern about what the work is actually for, and about whether people have the space to do it properly.
We talk about teams that feel stretched, with fewer people expected to deliver more. Steve’s hope for AI is practical: take repetitive work off their shoulders so they can spend time on analysis and opportunities. He is enthusiastic about that possibility. He is impatient with a board demanding AI while being unable to explain what it should improve.
There is a similar concern in his account of conversion rates. He tells me about achieving eighteen per cent when the telephone lines in a mail-order business failed and customers came online instead. A spectacular number, produced by an unusual day. A poor foundation for everyone’s future expectations.
His question is what we lose when a transaction becomes the only interaction that counts. Someone can come to a website, enjoy a product story, learn about the brand or find a store. A relationship can be forming before a purchase appears in a report.
I hear a connection between that and how he describes the people around him. Pay attention to what is happening before you decide what it means. Give people room. Understand the reason behind the behaviour.
That is my reading of Steve, rather than a framework he announces. Experience seems to have given him the confidence to ask an ordinary question in a room full of expensive answers: what are we actually trying to do?
We end with a career soundtrack. I’m Shipping Up to Boston by Dropkick Murphys. He says it needs to be something chaotic.
I like that choice. The man can be calm while the journey is anything but.
Listen to or watch the full conversation below.
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Steve Webster is Founder and Principal of Barking Cat Advisory. Find him at https://barkingcat.ai and on LinkedIn.
The Struggle Bus with Vinny O’Brien is a VSpot Media programme. Season Four is in partnership with VirtualStock.