Evaluate Big Strategic Choices: Proven 3-Step Guide

Evaluate Big Strategic Choices
When the goal is to win big, playing it safe or moving too slowly is its own form of risk. Major opportunities rarely wait for perfect conditions. As you evaluate big strategic choices at your next executive strategy retreat, ensure your organization is anchored by a clear, well-articulated corporate strategy. The right strategy:

• Sharpens decision-making.
• Aligns leaders around a shared direction.
• Gives you the confidence to act decisively.

Combined, it enables leaders to make bold moves while intentionally managing risk — not avoiding it — so ambition is supported by discipline rather than hesitation.

Examples of Big Strategic Bets
Every company operates in a different context, but a big strategic bet shares a common definition: a bold, high-stakes decision intended to fundamentally reshape the business and materially change its trajectory. These bets are typically made to unlock outsized growth in the face of uncertainty. Some succeed spectacularly. Others become cautionary tales.

Big strategic bets that paid off include:

• Netflix shifting from DVD rentals to streaming — and later doubling down by creating its own original content.
• Spotify rewriting the economics and consumer experience of the music industry.
• Amazon launching Amazon Web Services (AWS), which became a dominant profit engine far beyond retail.
• Pfizer creating a dedicated phone line to help doctors and patients navigate insurance access — improving adoption and loyalty while removing friction.

Big strategic bets that failed include:

• IBM and Sony prioritizing hardware while underestimating the long-term power of software and ecosystems.
• Kodak failing to move fast enough into digital photography despite inventing the technology.
• BlackBerry underestimating how B2C expectations would shape B2B buying behavior.
• Excite passing on the opportunity to acquire Google for under $1 million.

And then there are the bets still playing out.

Planet Fitness
After decades of promoting its iconic $10 monthly membership to attract first-time and casual gym-goers, Planet Fitness recently announced a 50% price increase. It is a meaningful departure from the brand’s historic value proposition — a big bet that could either unlock higher profitability or erode the very differentiation that fueled its growth.

Microsoft
Microsoft’s $8.5 billion acquisition of Skype was intended to secure a leadership position in consumer and enterprise communication. Instead, Skype struggled to compete with platforms like FaceTime and WhatsApp and was ultimately shut down in favor of Microsoft Teams — a reminder that scale alone does not guarantee relevance.

Impossible Foods vs. Beyond Meat
The two leaders in plant-based meat are making sharply different strategic bets. Beyond Meat has moved away from directly imitating meat, introducing products that are less processed, cleaner, and positioned as healthier alternatives. Impossible Foods is leaning into a “meatier” brand identity, launching a more indulgent burger and even exploring a blended product made with both beef and plant protein. Each path reflects a distinct view of future consumer demand. Only one — or neither — will prove right.

Big strategic bets are rarely obvious in the moment. What separates the winners from the losers is not boldness alone, but clarity of strategy, speed of execution, and the discipline to adapt when assumptions collide with reality.

A Guide to Choosing Your Bold Strategic Move Wisely: Evaluate Big Strategic Choices

Evaluating big strategic choices demands rigor, not bravado. Bold moves succeed when they are grounded in disciplined thinking and informed by real data — not just optimism or financial modeling. Doing the homework means stress-testing your growth strategy from multiple angles and challenging your own assumptions.

Financial returns matter, but they are rarely sufficient on their own. The most consequential strategic decisions ripple far beyond the balance sheet, reshaping how you compete in the marketplace, how your strategy is executed, how your culture shows up under pressure, and whether your talent can actually deliver on the ambition. Ignoring any one of these dimensions increases risk dramatically.

As with any sound strategic decision-making approach, there are three critical factors to consider before placing a bold strategic bet.

1. Financial Performance Perspective
   Like any business case for change, you must start by understanding the specific financial implications of your big strategic choices. How will your choices add value to the business both now and in the future compared to other available alternatives?

   For example, one client recently launched its first product as a big strategic foray into the consumer packaged goods marketplace.  This was a big bet with big financial implications.  Their current service offering runs at 80% gross margin while their new product will average close to 40% gross margins.  Yet, the move made sense because they are expanding revenue channels and using their services to drive products and visa-versa.

   Another client invested heavily into entering an adjacent market to meet aggressive growth targets.  Unfortunately unexpected pricing pressures that did not match their value proposition forced them to scrap their big growth plans pretty late in the game.  They did not understand the structural attractiveness of the market or their target buyers.

   Another client forecast $150 million in revenue from a new product launch and invested heavily to bring it to market.  After two years, it only generated $3.5 million in revenue.  The company had to reverse course and conduct significant layoffs to right size.

   The financial perspective is a great place to start to evaluate big strategic choices and market potential.  Use it as a checkpoint to ensure that it is worth the time and effort to keep your big bets moving forward.

   Do the finances make sense for your strategic big bets?

2. Capacity to Deliver Perspective
   Even the most attractive financial case and compelling market opportunity will collapse without the organizational capacity and mindset to execute. Strategy does not fail in spreadsheets; it fails in day-to-day behavior. To deliver on bold strategic bets, you need the right foundation in place — organizational structure, workplace culture, talent, operating practices, systems, and processes that actually support the strategy you are trying to run.

   Our work assessing organizational culture consistently shows the same pattern: when capacity lags ambition, execution breaks down. Leaders announce bold moves, but the organization continues to operate as if nothing has changed. Without an implementable strategy and the infrastructure to support it, momentum fades and results stall.

   One client made a decisive shift from selling legacy hardware to offering software and services in response to a declining market. On paper, the move was sound. In practice, it failed. The organization did not invest in building a customer-centric culture or the consultative selling capabilities required to compete in the new model. Metrics and reward systems continued to reinforce transactional behavior. The result was predictable: entry into a more attractive market, but with old ways of working that undermined success.

   Contrast that with Netflix. Even while DVDs were still driving the majority of profits, leadership made an unambiguous cultural call. DVD employees were no longer invited to company-wide meetings — a deliberate signal about where the company was headed. Netflix was fully committed to its vision that entertainment would move into the home via the internet. In 1999, that conviction represented a massive risk. But the organization aligned its culture and capacity to match the bet.

   The hard question for leaders is not whether the strategy is bold enough. It is whether the organization is truly built to deliver it.

   Are your ways of working aligned with your strategic big bets — or are they quietly pulling you back toward the past?

3. Unique Customer Competitive Advantage Perspective
   This factor cuts to the heart of competitive advantage: how clearly and consistently you differentiate in the eyes of your ideal customers. Bold strategic moves only work when they strengthen — not blur — why customers choose you over credible alternatives.

   Winning here requires deep self-awareness and external clarity. You must understand your own distinctive capabilities, the unmet priorities of your target customers, and how competitors are positioning to serve those same needs. Without that insight, bold moves become expensive experiments rather than strategic advantages.

   The strongest strategic bets are grounded in an honest assessment of fit. Where do your strengths align uniquely with what matters most to customers? Where do competitors overinvest in features or price while underdelivering on experience, outcomes, or trust? When you clearly see these gaps, you can place bold bets with conviction rather than hope.

   Too many organizations chase growth by copying what appears to work elsewhere. That path rarely leads to advantage. Sustainable wins come from making deliberate choices that sharpen your differentiation and make it easier — not harder — for your ideal customers to say yes.

   The real test is simple and unforgiving: do you have a compelling, defensible reason that your ideal customers will choose you the majority of the time?

The Bottom Line
Designing a winning strategy — especially one that includes bold strategic bets — is hard work. There are no shortcuts. But it can be done well. The organizations that succeed take an honest, unsentimental view of where they are today, rigorously assess market opportunities and competitive realities, and then make deliberate choices about where to invest time, talent, and capital. Bold moves pay off when ambition is matched with clarity, discipline, and the commitment to build what it takes to win.

No one said that designing a winning strategy, let alone one that includes a bold move or two, was easy.  But it can be done and done well.  Analyze your current position carefully and objectively, build in what you know about market opportunities and your competition, and allocate and invest the resources you will need to accomplish your goals.

To learn more about how to evaluate big strategic choices, download How Strategic Clarity Distinguishes High Performing Leaders

by Tristam Brown: CEO

Tristam Brown is an executive business consultant and organizational development expert with more than three decades of experience helping organizations accelerate performance, build high-impact teams, and turn strategy into execution. As CEO of LSA Global, he works with leaders to get and stay aligned™ through research-backed strategy, culture, and talent solutions that produce measurable, business-critical results. See full bio.