The Day I Lost a Pitch by Telling the Truth
On honest estimates, incompatible requirements, and a beer three years later.
I have lost work by telling the truth. More than once. But one case has never left me.
We were a small software house — I was CTO — and we had built something worth having: a finance origination platform that we white-labelled and customised for clients in a specialised industry. Each implementation meant taking the core system and shaping it around how a particular client operated: their product structures, their incentive arrangements, their promotions, all layered on top of the financial and accounting requirements that the law doesn’t negotiate on. We were good at it. We were building a reputation. And one of the largest players in the industry took notice.
They sent us an RFP. Attached to it was a requirement that we found rather more interesting than the specifications: the work had to be complete within six months of engagement.
This was a David and Goliath situation — they were that much larger than we were — and our CEO very much wanted to land them. I very much did not want to respond at all. The requirements document was a mixed bag of incompatible specifications, and when we asked questions, the answers were uninformative and faintly annoyed, as though the questions themselves were an impertinence.
We responded anyway. Our honest estimate broke into two phases: two months of white-labelling running concurrently with one month of requirements clarification, followed by a second engagement for the remaining customisation work — somewhere between six and ten months, depending on how the conflicting requirements resolved and how complex the integration with their general ledger system turned out to be. Eight to twelve elapsed months in total. We couldn’t be more specific than that. Nobody could, honestly, at that stage.
In the process of preparing the bid, I had got to know one of their staff. We weren’t friends — more like two people who had recognised something in each other across a table. We both understood what was actually happening: that any estimate submitted in response to this RFP was a guess at best and pure fiction at worst. He knew it. I knew it. The difference was that I was writing mine down honestly.
At our end-of-year company picnic, the CEO told me we hadn’t got it. I stepped aside and called my contact at the other firm. He let slip — probably more than he should have — that we’d been rejected because we couldn’t commit to six months. The successful applicant, a large offshore consulting firm, had committed to the timeline and come in at roughly the same price.
“He knew it. I knew it. The difference was that I was writing mine down honestly.”
Our CEO was crestfallen. Our development team, when I told them, reacted the way I had: with quiet, private relief. There is something clarifying about losing work you didn’t want.
Three years or so later, I ran into that same contact at a conference. About agile development, as it happens. He had moved on to another company but was still in touch with people at his old firm. Over a beer — low-carbohydrate, given my circumstances — he told me what had happened. The project had run for a little over two years. It had cost approximately three times what we had proposed. It had been scrapped. They were going out for new proposals.
Were we invited to respond this time?
We were not. Either they were too embarrassed — unlikely — or they were still looking for someone to tell them what they wanted to hear.
I hope they found them.
This story is one instance of a general pattern — an industry built on a mental model that everyone in the room knows is wrong. I’ve made the full case in Code is Design. It turned out to need a book rather than an essay.