Positioning that connects

Strategy to lose

May 29, 2026
Ryan Hall
Founder

There’s a framework most of us have been handed at some point in our careers. It’s called strategy to win, and it goes something like this.

What’s happening in the market right now? What problem or opportunity exists that we can move toward? Who exactly are we targeting, and where do we have the best chance of competing? How do we differentiate from everyone else in the room? What strategy gives us the best route to winning? What channels and tactics will we use to get there? What capabilities do we need that we don’t currently have? What are the risks and assumptions we’re carrying? How do we stand out in the process? How do we work the back channel? How do we break the process in our favour? And what is our desired outcome?

It’s a solid framework. Rigorous. Most good businesses use a version of it.

But there’s a situation that framework doesn’t account for. And it’s one I’ve been in more than once over many years of building B2B businesses.

The situation where you know, before you’ve written a single slide, that winning isn’t actually the point.

The opportunity that changes the shape of things

Every growing business reaches a moment where something lands that’s bigger than where you currently sit. Not slightly bigger. Noticeably bigger.

A brand you’ve wanted to work with. A scope of work that would change your trajectory. A chance to operate at the next level and use it as a platform for everything that comes after.

When those come around, you feel it immediately.

This year, one of those landed for us. A brilliant brand. A programme of work that was almost perfectly aligned with what we do. A genuine invitation to pitch, not a speculative approach on our part. The brief was ideal.

And then we looked at the list.

We were the smallest supplier by a distance. Not marginally. Significantly.

The next smallest competitor was ten times our size. When we looked at the other names in the process, it was clear. This business was looking for a partner with scale. Not a business with potential and a strong trajectory. Scale. Today. Now.

Most businesses in our position would have made a pragmatic decision and declined. The pitch cost alone is considerable. Team time is not free. Opportunity cost is real. Competing at a level where the structural odds are stacked against you is a difficult thing to justify internally.

We didn’t decline.

We doubled down.

Because we already had a strategy. Just not the one people usually mean.

And that strategy wasn’t to win. It was something more strategic.

What strategy to lose actually is

Let’s be precise about this, because the phrase is deliberately provocative, and I want to make sure the meaning lands.

A strategy to lose is not defeatism. It’s not a way of dressing up failure in advance or making yourself feel better about an outcome you expect. It’s not a consolation framework.

It is a deliberate decision to enter a competitive process you are unlikely to win commercially, with a clearly defined and fully intentional set of outcomes that exist entirely outside the contract.

It starts with honesty. We knew the odds. We weren’t pretending otherwise. And from that honesty came clarity about what we were actually entering the process to achieve.

Our strategy, specifically

Strategy without a specific outcome is just intention dressed up as overthinking.

Our objectives for this pitch was simple.

Not to win this pitch but to win the next one.

We wanted to understand at depth what a business of this scale, with this kind of procurement process, actually needs from a partner. Not what we assumed based on our experience with smaller businesses. What they genuinely need, described in their language, surfaced through their own evaluation process. That intelligence is worth money. It shapes our product, our positioning, our offer structure.

We wanted to build relationships. Senior relationships. With the people who will be making these decisions for the next three, five, ten years. One pitch doesn’t close a relationship. Handled well, it opens one. We wanted those people to know who we are, how we think, and what it’s like to work with us, before we ever have a commercial arrangement.

We wanted to build our knowledge base around this specific client so thoroughly that when the opportunity presents itself again, we are not starting from scratch. We are ahead. We already understand their structure, priorities, language, and concerns. That is a significant competitive advantage in any future process.

We wanted to test our team. Real procurement-driven pitching at this level is a different environment from anything else we do. The rigour is different. The pressure is different. The way you need to think on your feet is different. You cannot develop that capability without being in it. This was the environment.

Lastly, and this is my favourite bit, we wanted to make it genuinely difficult for them to choose someone else.

Not to embarrass the competition or to win through confusion, but to make sure that every person in that room left knowing exactly who Friday Solved is and what we stand for. To make the decision harder than they expected. To plant a flag.

Those were the objectives. Defined before the first slide was written.

What it felt like in the room

There’s something clarifying about walking into a pitch where you’ve already made peace with the likely outcome, but there’s also something that sharpens you. You stop trying to manage perception and start focusing entirely on being exceptional.

We prepared with the same intensity we bring to any major pitch. The research was thorough. The thinking was original. The deck was built to reflect exactly how we work and why that matters. We were demonstrating depth of thinking, quality of approach, and a team that can hold its own at any level.

The conversations were excellent. Not politely excellent. Genuinely excellent. The kind where you can feel the people across the table engaging with what you’re saying rather than just evaluating it. We asked good questions. We challenged some of the assumptions in the brief. We put forward a point of view on their market that surprised them.

We also, without flinching, acknowledged the size gap. Not defensively, not apologetically. We named it directly and explained why we believed it was a temporary condition and what our trajectory looked like. Confidence without pretence is a rare thing in pitches. It lands.

We didn’t win.

But that was the whole point.

We ticked every single objective on our list.

And we’re now set up for the next phase of our strategy. To nurture and win the second pitch, having already established ourselves with the brand.

They know us now. They know how good we are and what to use us to solve. The next brief will be better shaped. And we’ll win it.

Let’s wrap this up

Strategy is about engineering the outcome you intend. Not the outcome you hope for, not the outcome that looks best externally.

The outcome you decide on before the process starts, and measure yourself against it honestly when it ends.

By that measure, this was a success. A genuine, deliberate, fully executed success.

The relationships are live. The knowledge base exists. The team came through it sharper. The brand knows who we are. And the work continues, as it always does in a relationship-first approach to sales.

We are in the nurture phase now. Building value consistently, staying visible, demonstrating over time that the gap closes faster than they anticipated. Finding the right moment. Preparing for the next opportunity with the same intent as the last one, but from a much stronger foundation.

Here’s what I want to leave you with.

Not every pitch is about the contract. Some of the most commercially important moves a growing business makes are the ones that don’t show up in this quarter’s revenue. The ones that shape the pipeline two years from now, the ones that develop the team, the ones that build the relationships that eventually become your best clients.

If an opportunity is in front of you that you know you probably won’t win, the question isn’t whether to decline. The question is: what would a strategy to lose look like, and is it worth executing?

Sometimes the answer is no. The cost is too high and the return too speculative.

But sometimes, it’s one of the smartest things you can do.

Being strategic in sales means understanding that winning and succeeding are not always the same thing. Define your intended outcome. Execute against it with full commitment. Measure it honestly.

And then keep going. The work on this prospect has only just begun.

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