Golden Rule to Remember: It always takes longer and costs more.

— #ProjectManagementTweet, Himanshu Jhamb & Guy Ralfe (2010)

There’s a rule that every executive knows but very few will say out loud in a room full of clients and stakeholders. It goes like this: it always takes longer and costs more. Always.

In 2016, I watched this rule play out in real time — at significant cost to a client relationship, to a team’s wellbeing, and to what had been a hard-won reputation for delivery.

The Deal

Our company was in the middle of a serious growth phase — the kind where momentum feels unstoppable and every new win seems to confirm that the trajectory is right. Our CEO had personally been part of a long, intensive sales pitch for a deal that mattered. The kind that gets announced internally, that people point to as evidence the company is going somewhere. The client was reputable, well-known in the industry, and the scope of what had been agreed was significant.

I was given a free hand to build the delivery team. I put together what I genuinely believed was the right group of people — experienced, committed, capable. And then we got to work.

What Followed

The team struggled. Not because they weren’t good enough, and not because the work was fundamentally beyond us. They struggled because the commitments made during the sales process had never been stress-tested against delivery reality. The scope had been agreed, the timeline had been set, the price had been signed — all before anyone on the delivery side had sat in the room and asked the inconvenient questions.

What followed was one of the more painful years of my career. We eventually delivered what had been promised — but nine months late. By that point, the cost of the project had ballooned well beyond what had been planned, the client was deeply unhappy, and the team had been ground down by a year of trying to close a gap that probably never should have existed in the first place.

What I Took Away

Looking back, what this experience exposed was deceptively simple: sales teams and delivery teams need to be in the room together before any commitment goes to a client. This sounds obvious when you say it. It almost never happens in practice.

Sales teams are wired to close. That’s their job, their measure, their reward. The deal feels like the destination. But it isn’t — it’s the beginning. Winning the contract means very little if the delivery that follows erodes the client’s trust over the next twelve months. The long game in any SAAS/Services business isn’t winning one deal; it’s winning the confidence of the people who gave you that deal, so they come back and bring others. You can’t build that on the back of a promise that was never realistic to begin with.

Delivery teams carry their own blind spot. They focus on scope, timelines, and resources — and sometimes lose sight of the fact that without the sales team stepping well outside their comfort zone to win the business, there’d be nothing to deliver. The relationship between selling and delivering isn’t a handoff. It’s a partnership, and it needs to exist from the very first conversation about what’s possible. Both functions are essential, and neither can succeed without the other.

What’s needed is a disciplined approach where delivery has a genuine seat at the table during the sales process — where the people who will be held accountable for the outcome have the opportunity to stress-test the commitment before it’s made, not after.

The Thing No One Says in the Room

Here’s what I find most interesting about this golden rule — and it took me a while to see it clearly. Clients know it too.

Experienced executives on the client side have been through enough projects to understand that the original estimate is rarely the final one. They won’t say this, especially not in a room where their own stakeholders are watching. But privately, what they’re really asking isn’t ‘will this come in exactly on time and on budget?’ What they’re asking is: ‘Will this team be straight with me when things get hard? And will the overrun stay within limits I can defend to my own leadership?’

The real damage isn’t the delay or the cost. Both of those are manageable when the relationship is intact and the communication has been honest. The real damage comes when the overrun arrives as a surprise — when the trust is already gone before the difficult conversation has even begun.

Technical problems are almost always fixable. Trust, once lost at the executive level, is another matter entirely.

If your sales and delivery teams are operating as separate worlds, I’d be happy to talk through what that dynamic is costing you — before the next deal makes it undeniable.