Start With Ambition

There is one meeting that has stayed with me far longer than many of the deals I've won.

I couldn't tell you exactly when it took place, or even how the pursuit eventually ended. What I remember isn't the commercial discussion, the demonstration or the inevitable negotiation that accompanies any significant enterprise transformation. What I remember is a procurement leader interrupting a room full of colleagues and asking a question that, until a few weeks earlier, had only ever come from me.

"What is our level of ambition here?"

The room fell silent for a moment, not because the question was particularly difficult, but because it wasn't the question anyone had expected to be discussing. The meeting had begun, as these meetings often do, with a review of the current operating model. There were diagrams of existing workflows, frustrations that had accumulated over the years and a growing list of requirements that would eventually find their way into an RFP. It was all perfectly sensible. Every organisation embarking on a transformation has to understand where it is before deciding where it wants to go.

Then he continued.

"Are we simply trying to improve a process that everybody already agrees is inefficient and frustrating, or are we prepared to define what good really looks like and allow a partner to help us get there?"

I remember driving home afterwards with the uncomfortable feeling that something important had just happened, although I couldn't quite explain why. At first I assumed it was simply satisfying to hear a customer repeating some of the language we had been using throughout the pursuit. Sales people are not immune to moments of vanity, and hearing your own thinking reflected back at you is naturally reassuring.

Looking back, I think I misunderstood what I had witnessed.

The important thing wasn't that he had adopted my words.

It was that he had made them his own.

The conversation had stopped being about selecting a vendor and had become a conversation about the organisation they wanted to build. Somewhere between our first meeting and that workshop, the discussion had shifted from evaluating solutions to questioning assumptions, and once that happened the technology almost seemed to become secondary. The room was no longer debating which platform scored highest against a list of requirements. It was debating the future of the organisation, and the software had become only one possible enabler of that future.

That distinction has become more interesting to me with every passing year because I have gradually come to believe that many transformation programmes begin in entirely the wrong place.

Not because organisations fail to understand their current processes. Most understand them remarkably well. They know where manual work has crept in, where governance has become unnecessarily complicated and where yesterday's technology no longer supports today's business. If anything, organisations have become exceptionally good at documenting the shortcomings of the present.

What they often find much harder to articulate is the future they are actually trying to create.

Those are not the same conversation, yet they are frequently treated as though they were.

I found myself asking customers, almost instinctively, "What is your level of ambition?" because I was rarely interested in whether they wanted another software platform. Nobody wakes up wanting a new Vendor Management System or a more sophisticated procurement workflow. Those things only matter because they support something else. The real question was always whether the programme existed simply to improve an existing process or whether it formed part of a broader ambition to become a different kind of organisation.

That distinction may sound philosophical, but it has very practical consequences.

A company doesn't rewrite its corporate vision because it wants to implement enterprise software. It invests in technology because it hopes to become more agile, easier to do business with, more resilient or better equipped for growth. Somewhere between those broad strategic ambitions and the project team tasked with delivering a transformation programme, that connection is often weakened. The programme develops a momentum of its own and, almost without anyone intending it, success becomes defined by delivering the project rather than by advancing the organisation's wider ambition.

I have often wondered whether this is why so many transformation programmes feel strangely disconnected from the organisations they are supposed to serve.

The discussions become increasingly detailed. Workshops produce process maps, requirements documents expand into hundreds of pages and evaluation criteria are refined until they appear wonderfully objective. Every step is logical. Every step is necessary. Yet the further the programme progresses, the less frequently anyone seems to ask the question that mattered most at the beginning.

"What does good actually look like?"

Perhaps that explains why I have always enjoyed that question so much.

It is one of the very few questions that cannot be answered with a product demonstration.

It forces everybody in the room to stop talking about software for a while and start talking about people. What should managers experience? How should employees interact with the organisation? What behaviours are we trying to encourage? Where should decision-making happen? If we were building this organisation today rather than inheriting twenty years of historical processes, would we really design it the same way?

Those conversations are rarely efficient.

In fact, they often feel frustrating because they create uncertainty rather than removing it. Assumptions that had quietly become accepted as fact suddenly come under scrutiny. Stakeholders realise they have been solving different problems without recognising it. Progress appears to slow because the group has stopped searching for answers and has gone back to asking questions.

Looking back over many enterprise pursuits, I have come to believe that this apparent slowing down is often the moment when the real work begins.

Once an organisation develops a shared understanding of the future it is trying to create, everything else becomes noticeably easier. Technology can finally be evaluated in context. Requirements stop reflecting departmental preferences and start reflecting organisational priorities. Procurement can perform its role far more effectively because the specification is no longer describing today's frustrations. It is describing tomorrow's ambition.

Ironically, that is also the point at which many organisations decide they are ready to issue an RFP.

I have nothing but respect for good procurement. Throughout my career I have worked with procurement professionals who have brought rigour, fairness and commercial discipline to some extraordinarily complex transformation programmes. This isn't an argument against procurement.

It is an argument about timing. By the time an RFP is published, the most important conversation should already have happened.

The organisation should already understand the future it is trying to build, because an RFP is exceptionally good at evaluating responses to a vision. It is considerably less effective at helping create that vision in the first place.

That realisation also explains one of my recurring frustrations during my last three leadership roles. Customers would quite reasonably ask, "What does good look like?" I welcomed those discussions because they pushed us beyond products and into organisational design. Afterwards I would go back to our solution architects, our enablement teams and our product specialists looking for evidence that would help us answer the question with conviction.

Not another customer reference. Not another implementation methodology. I wanted to know what we had actually learned.

Across dozens, perhaps hundreds, of transformations, what patterns had emerged? Which operating models consistently delivered better outcomes? What had surprised us? If another customer wanted to know what excellence looked like, where was the accumulated wisdom that twenty years of implementations should have produced?

To my disappointment, it was remarkably difficult to find. We had become exceptionally good at documenting implementations. We had become much less effective at documenting transformation. Those are not the same thing. An implementation tells you what happened. Transformation should teach you why it mattered.

When I think back to that procurement leader asking his colleagues about their level of ambition, I realise he wasn't looking for another vendor to answer a list of questions. He was looking for a partner who could help his organisation ask better ones.

Perhaps that is the role enterprise sellers should aspire to play.

Not because it leads to shorter sales cycles. In my experience, it often does exactly the opposite. The early conversations become longer, broader and considerably more demanding because they are no longer about products. They are about organisational ambition, and ambition is rarely discovered in a two-hour workshop or captured in a spreadsheet.

What those conversations do create, however, is something infinitely more valuable than speed.

They create direction.

And once an organisation has genuine clarity about where it wants to go, the decisions that follow tend to become remarkably easier.

Perhaps that is why I have come to believe that the most important enterprise conversations should never begin with an RFP.

By the time the RFP is written, they should already be over.

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