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A Day Late and a Dollar Short

  • Writer: Linish Theodore
    Linish Theodore
  • Feb 12
  • 5 min read

Martin Brundle has a phrase he deploys with surgical precision during Formula 1 broadcasts: "a day late and a dollar short." He uses it when a driver attempts a defensive move too late, or commits to an overtake half-heartedly. The gap has closed. The opportunity has passed. And worse, the hesitation has telegraphed weakness to every other driver on the grid.

Business is no different. The difference is that instead of losing a position on lap 34, we lose teams, opportunities, and momentum. And unlike F1, where you get another race in two weeks, the consequences of late, tentative decisions can take quarters, sometimes years to recover from.


A few years ago, I had a team member with extraordinary potential. Brilliant thinker. Could see around corners that others missed. But the execution wasn't there. Deadlines slipped. Deliverables came in half-finished.


In our 1:1s, I'd say things like "the stakeholder feedback has been mixed" when what I meant was "you're losing the room." I'd frame missed deadlines as "let's talk about your prioritization" when the issue wasn't priorities, it was execution. I told myself I was being supportive. That I was giving them room to grow. That this was what good leadership looked like.


Six months of this. Six months where everyone else on the team watched me tolerate what I wouldn't tolerate from them.


When I finally made the call to exit them from the team, the conversation was devastating. They told me they'd known for months that something was wrong, but since I kept saying things like "we just need to tighten up execution a bit," they thought they were still basically on track.

I'd been unclear for so long that I'd accidentally led someone into thinking mediocrity was acceptable.


The damage wasn't contained to that one person. My highest performer came to me two weeks after the exit and said, "I've been waiting for you to do something about that for months.”


When mediocrity is tolerated long enough, it becomes the norm. And when you finally act, everyone's already adjusted their baseline downward.

I was a day late. And it cost me far more than a dollar.


I've watched this pattern play out dozens of times since then, across different companies and contexts.


Half-measures are expensive. They cost you the outcome you were trying to achieve. They cost you organizational trust. And they cost you the respect of the people watching you hedge.


I've pressure-tested this pattern enough times that I've built a simple framework around it. Four questions that separate conviction-based decisions from expensive theater.

Here's the first one, and it's the one that catches most aspiring leaders:

Can you communicate it in a way that eliminates ambiguity?


This sounds obvious. It isn't.

Think about the last time you had to deliver difficult feedback or announce an unpopular decision. How many qualifiers did you add? How much cushioning? How many escape hatches for the person receiving it to interpret it as "not that serious"?


In my performance management failure, I had multiple conversations that I thought were crystal clear warnings. Every single one had enough softening that the person could reasonably interpret it as "still meeting expectations, just needs minor improvement."


I said: "Some of the stakeholder feedback has raised concerns about follow-through."What they heard: "A couple people had minor complaints, probably not a big deal."What I meant: "You're losing credibility with the people who matter most, and if this doesn't change immediately, you won't survive here."

I said: "Let's build a plan to get your project delivery more consistent."What they heard: “He wants to help me with time management."What I meant: "Your inconsistency is becoming a team-wide problem and I need to see dramatic improvement in the next 30 days."

The ambiguity wasn't kindness. It was cowardice. And it made everything worse.


Compare that to how Formula 1 teams handle communication during races. When Red Bull needs Pérez to let Verstappen through, they don't say "Sergio, if you're comfortable with it, maybe consider letting Max past at some point." They say: "Sergio, let Max through this lap."

No ambiguity. No cushioning. No room for interpretation.


(Before you bring up McLaren: Stop. Just. Stop.)



The absence of ambiguity enables execution.


Here's how to test your own communication:


The 24-hour test: If someone heard your message and did nothing for 24 hours, would they reasonably believe they were still in compliance with your expectations?


If yes, you've been ambiguous.


When I finally had the conversation that led to exiting that team member, I said: "Your performance isn't meeting the bar for this role. We've discussed this multiple times without seeing the improvement I need. I'm giving you 30 days to demonstrate significant change in execution quality and stakeholder confidence.


If I don't see that change, we'll be transitioning you out of the company."

Was it uncomfortable? Extremely. Was it ambiguous? No. Did they know exactly where they stood? Yes.


The third-party test: If someone else on the team asked the person what was discussed, would the person's description match what you intended to communicate?



This is just one of the four questions. But communication clarity is where I see aspiring leaders sabotage themselves most often. They make the call, then cushion it to death. They announce the strategy, then undermine it with qualifiers. They claim conviction, then communicate in ways that preserve deniability.

You don’t need to be right all the time. You need to be clear. To make decisions decisively, communicate them without ambiguity, and take ownership of the outcomes.


If you're reading this and thinking about a decision you've been circling, one that keeps getting postponed, or one you've made but can't get the organization to actually execute - you're likely caught in the half-measure trap.


I'm happy to pressure - test it with you. Just 25 minutes where I'll walk you through the four questions, we'll find where the conviction breaks down, and you'll walk away with clarity on what's actually blocking you.


I do this because: one, it's genuinely useful, and two, it's how I figure out if we should work together. Some people just need the framework and they're off to the races. Others need help building the muscle and the organizational positioning to use it at scale. You'll know which one you are by the end of the conversation.

The aspiring leaders who break through to senior ranks aren't the ones with perfect judgment. They're the ones who make timely decisions with conviction, communicate them clearly, and take ownership of the outcomes, even when things don't go as planned.


The question isn't whether you'll make mistakes. You will. The question is whether you'll make them decisively, learn from them quickly, and build the reputation as someone who can be trusted with ambiguity.

If you're ready to pressure-test your approach: get in touch with me.



Don't be a day late and a dollar short on the calls that matter.

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