You Can’t Win From Losing: Execution Self-Assessment

Premise: You Can’t Win From Losing

In sport, business, and private equity alike, the scoreboard doesn’t always reflect talent—it reflects discipline. As Bill Belichick puts it: “You can’t win from losing.”

It’s a deceptively simple phrase, but it captures something every high-performance team eventually learns the hard way: you don’t get to win until you stop beating yourself.

Too often, leadership teams look outward—at competitors, market conditions, or macroeconomic forces—when in reality, their biggest obstacles are internal. Missed decisions. Poor follow-through. Functional silos. Repeating the same avoidable mistakes.

This is especially true in PE-backed businesses, where time is limited and execution drives value. The pressure is relentless, and the margin for error is small. If a leadership team is spending time correcting its own internal failures—unclear roles, rework, misaligned priorities—then it’s not building momentum. It’s playing from behind.

What this looks like:

– You’re in meetings about the same issue… again.
– Decisions are made, but not acted on.
– Everyone is busy, but outcomes are unclear.
– Good ideas stall because no one owns them end-to-end.
– Energy is drained managing internal complexity rather than solving customer problems.

None of this feels like “losing” in the moment—but it quietly erodes your ability to win.

The Lesson – Before you can scale, compete, or exit—you have to execute. And before you can execute, you have to stop losing unnecessarily.

The following self-assessment is designed to help your leadership team reflect honestly on where internal friction may be holding you back. It’s not about blame. It’s about clearing the path—so that your strategy, your people, and your capital can actually do what they’re meant to do: drive performance and create value.

1. Strategic Clarity

• Do we have a clearly defined strategy that all executives understand and can articulate?
• Are we consistently prioritising the initiatives that deliver the highest ROI against the value creation plan?
• Have we eliminated distractions—projects or legacy initiatives that no longer serve the strategy?
• Red flag: Constant “strategic pivots” without execution. Trying to win without knowing the game plan.

2. Operational Discipline

• Do we consistently hit deadlines and follow through on decisions?
• Are our KPIs visible, relevant, and regularly reviewed—not just by function, but by the whole leadership team?
• Is there a clear cadence of accountability (e.g. weekly performance reviews, monthly commercial check-ins)?
• Red flag: Missed deliverables, opaque metrics, or confusion around ownership.

3. Team Alignment and Ownership

• Is every leader clear on their role—and are they owning results, not just activity?
• Do we challenge underperformance directly and respectfully?
• Do we behave in a way that prioritises what’s right for the business, not just our functional silo?
• Red flag: “That’s not my job” culture. Team members protecting turf rather than solving problems.

4. Communication and Execution Cadence

• Are decisions made quickly, with input from the right people?
• Do we close the loop after decisions—making sure actions happen, not just that they were agreed?
• Are there known and respected short-interval controls (e.g. weekly sprints or leadership standups) to track momentum?
• Red flag: Meetings with no outcomes. Decisions revisited multiple times. Execution drift.

5. Internal Friction and Avoidable Mistakes

• Are we fixing root causes, or just dealing with repeated symptoms (e.g. constant firefighting)?
• Are our systems, tools, and reporting aligned and easy to use—or are they slowing us down?
• Are politics, indecision, or passive-aggressive behaviours costing us time and trust?
• Red flag: Solvable problems recurring again and again. Delays due to interpersonal dynamics.

Final Reflection

Private equity-backed companies don’t have time to waste. If you want to outperform, you first have to eliminate the avoidable errors that undermine performance. That starts with leadership.

Before you ask, “How do we scale?”

Ask instead, “Where are we losing unnecessarily?”