‘The true test of a leader is whether their followers will affirm them even when they are not in power.’

— Jeffrey Sachs

What happened at Hortonworks after our early success is a story that plays out in organisations around the world with depressing regularity.

The business had grown fast. The market was real, the product was strong and the team had cracked something genuinely difficult: how to sell an unfamiliar technology to cautious, risk-averse buyers – engineers and data teams who needed to understand their own doubts before they could embrace something new. We had done that by letting people think creatively, selling in human terms and building trust rather than pushing transactions.

For three years, we led the open-source big data market. We weren’t perfect, but we were fast, adaptive and genuinely good at engaging with the strangers who would decide our fate.

Then new leadership arrived. And in less than six months, almost everything we had built was gone.

The Tower 42 Meeting

I remember the moment it changed.

I was sitting in a conference room on the upper floors of Tower 42 in the City of London, waiting to hear the new leadership team outline their vision for EMEA sales. The previous leader – imperfect in some respects, but someone who understood people – had been replaced. In came two managers I had never met.

They spent ten minutes describing their track records. Their numbers. Their previous wins. And then, with almost no transition, they made it clear what they expected of us: ‘Go hit your number.’ That was the vision.

No curiosity about the team. No interest in what had worked or what hadn’t. No questions about the buyers we were engaging or the competitive dynamics we were navigating. Just a number –

and the implicit message that how we got there was our problem.

I knew, in that moment, that my time there was limited.

Over the next six months, I watched a high-performing team be systematically dismantled – not by a bad market or a weak product, but by leadership that confused rigidity for structure and pressure for motivation.

MEDDIC – the sales qualification framework – was enforced not as a tool but as a weapon. Every field of the model had to be completed, to the letter, regardless of whether doing so made commercial sense. In one particularly revealing moment, a sales rep returned from a client meeting and was immediately pulled into the office to go through their MEDDIC sheet – with the buyer’s procurement director still on the phone. The buyer was, in effect, being asked to comply with our internal process. The damage to that relationship was irreparable.

In another meeting, I had already exceeded my quarterly target. I was in the middle of a presentation that was going well. The new manager interrupted me – not because the content was wrong, not because a client was confused – but because he disapproved of my shirt.

Six months. That was all it took for nearly four years of hard-won success to unravel.

The lesson wasn’t that MEDDIC is a bad framework – it’s a good one, used correctly. The lesson was that any tool, applied without human judgement and without genuine interest in the people using it, becomes destructive. Process cannot substitute for leadership. And leadership cannot substitute for genuine curiosity about the human beings in your care.

What Real Leadership Looks Like

For me, the truest test of leadership is this: Can you engage with – and sell to – strangers?

Not strangers in the abstract, but the specific, complex, unpredictable people in front of you – your team, your buyers, your peers. People whose communication styles differ from yours. People whose doubts and fears you haven’t been briefed on. People who need you to meet them where they are, rather than insisting they meet you where you are.

If you cannot do that – if you cannot connect with someone you don’t know and build trust despite personality differences and competing priorities – you are missing what I consider the most essential leadership capability there is.

The managers who walked into Tower 42 that day had never developed it. Or, if they had, they’d been promoted so many times on the basis of their numbers that they’d stopped practising it.

Their identity was in their targets, not in their people. And when the targets became the only thing that mattered, the people –

and the performance that came from them – followed.

Leadership, done well, looks nothing like that.

It looks like the first manager I worked for in software – the warm, white-haired Irishman who flipped my CV face-down in our interview and spent an hour trying to understand who I was, not what I’d done. It looks like the leader at Hortonworks who gave us enough trust and space to figure out how to sell a new technology to a sceptical industry, and then got out of our way while we did it. It looks like Marc Benioff in the early years of Salesforce, personally interviewing every sales hire because he understood that the people you put in front of buyers are the living expression of your culture.

It looks like someone who is genuinely, relentlessly curious about the human beings they are responsible for.

The Ethical Dimension

From the buyer’s perspective, engaging with sellers – who are, always and inevitably, complete strangers – comes with an implicit expectation: ethical responsibility.

This goes far beyond courtesy or professionalism. Buyers expect sellers to treat every interaction not just as a sales opportunity, but as the beginning of a potential relationship built on honesty, respect and genuine mutual interest. They expect transparency about what a product can and cannot do. They expect honest communication about timelines and outcomes. They expect a willingness – rare but deeply valued – to prioritise their needs even when that means stepping away from the sale.

When a salesperson or a leader chooses not to operate within this framework, it raises uncomfortable questions. Not just about their personal integrity, but about the culture and values of the organisation they represent. What does it say about a company when its people view relationships as expendable? When trust is treated as optional? When buyers are processed rather than understood?

What happened at Hortonworks was a failure of leadership. But it was also a failure of ethics – a refusal to acknowledge that the way we engage with people matters, not just what we extract from those engagements.

Had we maintained the principles we’d been operating by before – the curiosity, the trust-building, the genuine investment in understanding the strangers we were selling to – the outcome might have been very different. Instead, by suppressing creative thinking and imposing rigid process, by prioritising the appearance of control over the substance of connection, the new leaders destroyed in six months what had taken years to build.

Choosing the Future

The B2B landscape has evolved. Buyers have evolved. The expectations of both the people who sell and the people who buy have evolved – profoundly and irreversibly.

The leaders who will succeed in this environment are not the ones with the most polished frameworks or the most impressive track records of hitting targets. They are the ones who understand that the greatest commercial asset their organisation possesses is not its product, its technology or its price point.

It is the quality of the human engagement their people deliver.

Every seller on your team is, in every conversation with a buyer, either building or eroding your organisation’s most valuable resource: trust. Not the abstract corporate trust that gets measured in brand surveys, but the specific, personal, relational trust that makes a stranger decide to take the next step – and the one after that, and the one after that.

Your job as a leader is to protect, develop and reward that capability.

Not to enforce the MEDDIC sheet. Not to approve the shirt. Not to stand at the emperor’s box and demand that your gladiators perform harder, better, faster.

But to create the conditions in which genuinely human, genuinely ethical, genuinely effective engagement can happen – and to recognise and celebrate it when it does.

That is the cautionary tale that Tower 42 taught me. And it is a lesson I have never stopped carrying.

The question for every leader reading this is a simple one: What kind of culture are you building? And what kind of stranger does your team become, when they walk into a room with a buyer?

The answer to that question is your legacy.