There’s a question that separates transformational leaders from those merely managing the status quo: Are you playing to win, or playing to not lose?
This distinction emerged during a conversation between Adam Grant and Brené Brown on his podcast, and it’s one that Brene says she revisits frequently with leaders. The question might sound like semantics at first – aren’t they the same thing? But the answer reveals everything about how you lead, how your team performs, and whether you’re building something meaningful or simply protecting what exists.
The problem with playing not to lose
Brene cuts straight to the heart of the matter in her interview: “I just say, what’s more important to you, to protect your ego or to win? And if you want to win, we’re going to have these hard conversations. And if you can’t have these hard conversations and you continue to play not to lose, let me tell you what that looks like, both on a field and in an organisation. Playing not to lose is always losing.”
That final statement deserves to be said again: Playing not to lose is always losing.
When leaders operate from a defensive position – avoiding difficult conversations, minimising risks, protecting their position – they create organisational cultures that are driven by caution rather than courage. This defensive leadership manifests in predictable ways: delayed decisions, watered-down strategies, avoidance of innovation, and a pervasive sense of playing it safe. The irony is that in attempting to avoid loss, these leaders guarantee stagnation, which is itself a form of losing in today’s rapidly evolving business landscape.
Why this distinction matters
The difference between these two mindsets isn’t just philosophical – it fundamentally shapes culture and performance. Leaders who play not to lose focus their energy on risk mitigation, damage control, and maintaining current positions.
- Their strategic planning centres on what might go wrong.
- Their communication focuses on stability and continuity.
- Their teams learn to be cautious, to seek permission rather than forgiveness and avoid rocking the boat.
- Conversely, leaders who play to win orient themselves and their organisations toward possibility.
- They ask different questions.
- They have different conversations.
- They inspire different behaviours.
This doesn’t mean it’s reckless abandonment or ignoring genuine risks. It means moving from a defensive to an offensive strategy, from preservation to creation, from fear to visionary.
The stakes are particularly high because this mindset cascades through every level of an organisation. Your leadership mindset becomes your team’s operating system. If you’re playing not to lose, your team will mirror that defensiveness, creating a culture where innovation is stifled, and mediocrity becomes acceptable. We are in the danger zone of apathy.
Shifting the mindset with three simple questions
If you want to shift from defensive to visionary leadership, you need clarity on three fundamental questions:
What does winning look like to you?
This requires specificity. Winning isn’t a vague notion of “doing well” or “being successful.”
- What measurable outcomes define success for your team or organisation?
- What impact do you want to create?
- What legacy are you building?
Without a clear picture of what winning means, you cannot lead others toward it. You’re asking people to follow you to a destination you haven’t defined.
What does winning feel like?
This question addresses the emotional and experiential dimensions of success.
- How will your team know when they’re winning?
- What will the culture feel like when you’re operating at your best?
This emotional clarity matters because people aren’t motivated solely by metrics (we are emotional beings who think, not thinking beings who feel). Employees are inspired by the experience of meaningful work, of being part of something larger than themselves, of contributing to outcomes they believe in, and you need to help them feel and see that.
What do we need to do to win?
This is where vision meets action. You need a strategy, yes, but you also need to identify the difficult conversations, the hard decisions, and the bold moves required to achieve your vision. This is where Brene’s insight about ego protection becomes critical. If you’re unwilling to have challenging conversations – about performance issues, strategic changes, resource allocation, or organisational change, you’re choosing ego protection over winning. You’re not leading with courage.
The visionary practice of credible leadership
Being able to articulate what winning means isn’t just about strategic clarity; it’s fundamental to leadership credibility. People will not follow a leader who cannot paint a compelling picture of where they’re going. They will not believe in someone who cannot communicate their vision with conviction and passion. They will not be inspired by a leader who seems more concerned with avoiding failure than achieving something meaningful.
This is what makes vision a practice rather than just a quality. Credible leaders consistently communicate what winning looks like. They return to these themes repeatedly. They connect daily work to larger aspirations. They demonstrate through their words and actions that they’re oriented toward achievement rather than mere survival.
When you lead with vision, when you play to win, you create the conditions for engagement rather than apathy. Your team understands what they’re working toward. They can see how their contributions matter. They feel permission to take intelligent risks, to innovate, to push boundaries. This is how movements are built.
Without the clarity and passion that comes from playing to win, you create apathy. People show up, complete their tasks, and go home. They don’t invest discretionary effort. They don’t challenge the status quo. They don’t bring their best thinking to work. They become risk-averse themselves, mirroring the defensive posture they see in their leaders.
You cannot create a movement, the kind of collective energy and commitment required for significant achievement, if your mindset is stuck in not losing. Movements require believers, and believers need something worth believing in. They need a vision of winning that inspires them to bring their full selves to the work – and you need to bring that as the leader.
Struggling to close the credibility gap in your organisation? I can help you transform your approach to employees with tailored communication strategies that build genuine trust and engagement. Get in touch today
