How Will We Win in Our Chosen Playing Field through Strategic Coaching?

A Question to Think About

“How will we win in our chosen playing field?” is a crucial question for leaders to reflect on during a strategic coaching session. This segment of the strategic coaching journey comes after defining the breakthrough goals and identifying the target customer segments. Businesses that answer this question with clarity will enable the organization to create, deliver, and capture value for competitive advantage in their chosen playing field.

Taking time to think about the question helps leaders to move from ideating ambition to taking action for results. And, this is the heart of competitive strategy; where vision meets execution, and intention meets capability. It’s not about vague aspirations like “being the best” or “delighting customers.” It’s about finding the way to win.

Beyond Competing: The Essence of Winning in Our Chosen Playing Field

Winning here is not a winners take all and loses take none approach. Here, winning means finding those elements of distinctiveness to set organizations apart from the field. Think of this as the “how” that makes the offerings of any one organization challenging for others imitate.

This is a key component in strategy. Because, it’s one thing to define a vision and set a breakthrough goal, it’s another thing to discover the essence which contributes to results. It could be that a distinct way of winning is not about doing more. Rather, it’s about doing differently, consistently, and in a way that others find hard to copy.

Organizations which win in their chosen playing filed know why they are chosen and what makes them hard to replace. They may not be chasing after every opportunity but instead design systems and capabilities that reinforce their chosen advantage. This clarity becomes a positive flywheel which attracts the right customers, strengthens culture, and aligns decisions across functions.

Strategic coaching helps decision makers answer the question of “How Will We Win in Our Chosen Playing Field?”. Such conversations can surface assumptions and test differentiators. It shifts the conversation from generic ambition (“we’ll just be best”) to a custom playbook: how value is created, delivered, and defended. Over time, that clarity becomes a pattern of choices in products, culture, systems, and brand identity that reinforce what gives the organization advantage.

The products or services that have wide, sustainable moats around them are the ones that deliver rewards to investors. – Warren Buffet, billionaire investor

Two Case Stories of answering “How Will We Win in Our Chosen Playing Field?”

1. Reframing and Redefining Speed

A regional logistics provider realized that competing on raw delivery speed was futile against global giants. Through strategic coaching sessions, the leadership team realized that speed was difficult to sustain, but easy to be copied, and so identified a different path. One that focused on reliability through transparency. They invested in real-time tracking, proactive communication, and customer service that prioritized visibility. Soon, clients equated their brand with dependability rather than mere speed. That differential became their way to win.

2. Precision, Not Price

A precision parts manufacturer once competed mainly on low cost. They took on every job that came their way. But in a strategic coaching exercise, leadership realized their greatest strength lay in producing high-tolerance components for aerospace and medical industries. These were high-value sectors that prized reliability and certification over price. They decided to specialize and became known for uncompromising quality and traceability. By narrowing their field, they gained a reputation that justified premium pricing and long-term contracts. Their focus, not their size, became their advantage.

Companies that solely focus on competition will die. Those that focus on value creation will thrive. – Edward de Bono, creator of the Six Thinking Hats

Common Pitfalls in the “How Will We Win in Our Chosen Playing Field” Conversation

1. Mistaking activity for strategy

Many teams can confuse being busy with being strategic. They may roll out campaigns, partnerships, and new products without a coherent thread tying them to a distinct way of winning. The result is momentum without direction that results in plenty of motion, but little progress. The antidote to this trap is focus. Through strategic coaching reflection, leaders can trace each initiative back to a clear competitive logic i.e. “how does this help us win?”. This ensures that every action reinforces a coherent strategy rather than diluting it.

2. Copying competitors

Benchmarking can provide insights, but imitation dilutes differentiation. The winning approach emerges from an authentic understanding of what makes the organization uniquely capable, not from replicating others’ moves. Strategic coaching on “How will we win in our chosen playing field?” encourages leaders to look inward first: What unique assets, culture, or relationships can be leveraged in ways competitors can’t easily copy? When framed this way, winning doesn’t always mean being first or biggest. Winning in this context means being different in a way that matters.

3. Ignoring enablers and constraints

Winning is not about wishful thinking. Every strategy must align with the organization’s resources, capabilities, and culture. Without considering these realities, even the most inspiring ideas falter during execution. Coaching helps leaders map their true strategic capacity: what can scale now, what needs to evolve, and where investments must go next. This awareness is key to jumping the S-curve, which is the critical point when an organization must move from its current model to reinventing for the next wave of growth. Ignoring enablers and constraints keeps organizations trapped at the plateau instead of leaping to new performance levels.

The competitor to be feared is one who never bothers about you at all, but goes on making his own business better all the time. – Henry Ford, founder of Ford Motors

Strategic Coaching Questions to Define “How We Will Win”

In the next strategic coaching conversation, consider asking, thinking, and reflecting on these questions to answer the big question of “How will we win in our chosen playing field?” to translate focus into competitive edge.

1. What do we consistently do better than others — and why does that matter to our chosen customers?
2. What are the key enablers (people, processes, technology, partnerships) that will help us sustain this advantage?
3. What are the offerings or experiences we offer that would be hardest for others to copy?
4. How do we align our operations, culture, and metrics to reinforce this winning approach?
5. What can we do better and more efficiently to remain aligned on this chosen path?

Putting time to find the answer to these questions nudge teams from vague ambition into deliberate, strategic distinction. They move the conversation from aspiration to deliberate choice, from general ambition to a clear game plan.

Making the Winning Strategy Stick

Ultimately, the goal is to build an organization that wins with purpose. Building one that delivers lasting value to customers, employees, and communities. Strategic coaching provides the framework to make these choices consciously and consistently. Strategic coaching ensures that the “how to win” choice doesn’t stay in slide decks, but becomes part of the daily operating logic. When leaders ask “how will we win in our chosen playing field?”, they commit to clarity, coherence, and consistency. This question becomes the spine of execution.

You have to learn the rules of the game. And then you have to play better than anyone else. — Albert Einstein, physicist

Book a no-obligation complimentary consultation with ITD World today to get your strategy going!

Other resources you might be interested in:

• 5 Executive Coaching Goals Leaders Need for Success
• Executive Coaching: Building High-Performing Leaders
• Business Coaching: A Definitive Guide to Harnessing Its Power
• Coaching People Who Don’t Want to Be Coached
• 7 Leadership Mistakes to Avoid: From Failure to Success