When you’re competing to win a project as an underdog, you’ve got the freedom to push away from conventions and dare to be different — which can make you visible enough to stand out from the competition, and maybe even win.
In today’s post, Dean shares a client case study of a smaller firm landing a plum project by doing just that.
To learn more about how we can help your team increase their chances of winning, check out our Shortlist Interview Support here.
When you’re pitching a project, sometimes you’re the favorite—and sometimes you’re the underdog. I once coached a small team going up against national firms with massive portfolios, deep benches, and brand power. They simply couldn’t compete on size or prestige. We weren’t going to “out-big” anyone. So we had to change the equation entirely. We had to be the starfruit in a room full of apples.
The key was the selection committee itself. There are four basic personality types you’ll encounter: the CEO types (blunt, results-driven), the thinkers (detail-oriented planners), the relators (team- and people-focused), and the inspirers (visionaries with big ideas).
In this case, the decision-makers were inspirers and relators. They weren’t looking for endless detail or data—they wanted vision, alignment, emotional resonance, and harmony among stakeholders. So we built the entire pitch around their priorities, not ours.
Our proposal—the one that got us shortlisted—was extremely detailed. But once we understood the personalities at the table, we realized that was the wrong energy. So we repositioned immediately.
At the start of the presentation, we acknowledged it directly: we had gone deep in our proposal, and now we wanted to raise the helicopter to show the big-picture thinking beneath it. From there, we focused on:
Instead of drowning them in details, we met them where they lived—concept, collaboration, and conviction.
Because we differentiated our approach, the committee connected with us. They felt understood. They felt aligned. And they chose us—the little guys—over much larger firms.
Most teams default to “we do this all the time, we know what we’re doing.” Guess what? Your competitors think the same thing. Everyone says they’re qualified. Everyone says they have experience.
Strategic teams go further. They ask:
That’s how underdogs win. Not by being bigger apples, but by showing up as something entirely different—something crafted for the people in the room.
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