Key Strategic Questions to Consider

Stop nodding along in meetings. Start having impact: Too often, meetings are filled with phrases like: ❌ “That sounds great” ❌ “Let’s table it for another time” ❌ “Let’s circle back when we have more info” From 10 years in high performing teams, here’s what I’ve learnt about meetings: Top performers aren’t afraid to ask the hard questions. Here are 13 questions you can ask to leave a mark: 1/ "What do we have to deprioritize to do this well?" ↳ Use to help create focus. ↳ Shows you understand we can't do everything at once. 2/ "What happens if we do nothing?" ↳ Use to overcome inertia. ↳ Helps identify true priorities. 3/ "Who's done this well that we could learn from?" ↳ Use when projects have been done before. ↳ Shows you want to use others’ learnings. 4/ "What's the simplest way to explain this?" ↳ Use to create clarity. ↳ Shows you understand the importance of simplicity. 5/ "What went wrong last time?" ↳ Use when repeating past initiatives. ↳ Shows you want to learn from experience. 6/ "How will we know if this is working?" ↳ Use when success isn't clearly defined. ↳ Shows you care about real results. 7/ "Who's going to own each workstream?" ↳ Use when responsibilities are unclear. ↳ Prevents the "someone else will do it" problem. 8/ "How does this affect our current priorities?" ↳ Use when new work might disrupt current priorities. ↳ Shows you're thinking about the whole picture. 9/ "Who might we upset by this choice?" ↳ Use when changes could impact others. ↳ Shows you consider how others might feel. 10/ "If we had half the budget, how would we do this?" ↳ Use to find creative solutions. ↳ Shows you can spark new ideas. 11/ "What aren't we seeing here?" ↳ Use when consensus comes too easily. ↳ Shows you look at problems from all angles. 12/ "How does this help us reach our primary goals?" ↳ Use when projects drift from objectives. ↳ Makes sure we're not getting sidetracked. 13/ "What's our plan for the worst-case scenario?" ↳ Use when planning risky initiatives. ↳ Shows you think ahead. Remember: Impact can from asking the right questions. You don't have to be the smartest one in the room. Just ask the questions that make others think differently. P.S. Which of these will you use in your next meeting? — ♻ Repost to inspire your network to have more impact at work. ➕ Follow me (Will McTighe) for more like this.

Today's episode will make you better at developing a strategy, and evaluating other people's strategies. Roger Martin is one of the world’s most sought-after experts on strategy, and the author of "Playing to Win", one of the most popular (and most actionable) books on learning the art of strategy. He’s written extensively for the Harvard Business Review; consulted for dozens of Fortune 500 companies, including P&G, Lego, and Ford; and written 11 other books on strategy, leadership, and clear thinking. In our conversation, we cover: 🔸 The five key questions you need to answer to develop an effective strategy 🔸 How most companies get strategy wrong 🔸 How to avoid “playing to play” instead of playing to win 🔸 Real-world strategy examples from Figma, Lego, Procter & Gamble, and Southwest Airlines 🔸 Why you need to either differentiate or be the lowest cost 🔸 Shortcomings of current strategy education 🔸 Much more Listen now 👇 - YouTube: https://lnkd.in/gTyPQZus - Spotify: https://lnkd.in/gKWWm-Fp - Apple: https://lnkd.in/gCing92Q Some key takeaways: 1. Strategy is an integrated set of choices that compels a desired customer action. 2. Great strategists aren’t born; they’re made through practice. Even if you see yourself as more operational than strategic, remember that strategy is a skill that anyone can develop over time. Just like any skill, it improves with practice. 3. To win in business, you must be either a low-cost provider or differentiated. If you’re neither, competitors can “bully” you and take market share. Two questions can help you figure out whether you’re winning in these ways. First, could you match competitor price decreases and remain more profitable than them? If not, you’re not a low-cost provider. Second, could customers essentially flip a coin between you and a competitor? If so, you’re not differentiated enough. 4. Use the Strategy Choice Cascade to define and implement effective business strategies. This framework consists of five essential questions: a. What is our winning aspiration? Clarify what you aim to achieve with your strategy. This guides all subsequent decisions and actions toward a clear objective. b. Where will we play? Select specific markets, segments, or niches where you will compete. Focus is crucial; trying to be everywhere can dilute effectiveness. c. How will we win? Determine your competitive advantage. You must either offer customers superior value or operate at a lower cost than competitors in your chosen areas. d. What capabilities must be in place to win? Identify and build capabilities that are critical for executing your chosen strategy effectively. These should be distinctive strengths that set you apart from competitors. e. What management systems are required to ensure the capabilities are in place?

20 Questions to Lead Your Team (and what to listen for) Great leaders don't give better answers. They ask better questions. Here are 20 questions that unlock high performance: EXECUTION (How Work Gets Done) 1. "How do you measure success?" Listen for: Precision over platitudes ✅ Are metrics clear and mission-aligned? 2. "What does excellence look like?" Listen for: Standards over statements ✅ Can they define the exceptional? 3. "Name our three critical priorities." Listen for: Focus over fragmentation ✅ Do they know what truly matters? 4. "Where do you get blocked?" Listen for: Solutions over symptoms ✅ Can they diagnose root causes? 5. "Which processes feel unnecessary?" Listen for: Efficiency over effort ✅ Will they challenge sacred cows? ENGAGEMENT (What Drives People) 6. "What energizes you most?" Listen for: Passion over performance ✅ Where does their energy naturally flow? 7. "How do you prefer feedback?" Listen for: Growth over comfort ✅ Do they invite improvement? 8. "What skills do you want to build?" Listen for: Ambition over acceptance ✅ Are they driving their development? 9. "When were you most proud?" Listen for: Values over victories ✅ What achievements truly matter? 10. "Where do you want to be in one year?" Listen for: Direction over dreams ✅ Is their path purposeful? ALIGNMENT (Staying Connected) 11. "How does your work impact our mission?" Listen for: Purpose over position ✅ Do they see their strategic value? 12. "What's our biggest opportunity?" Listen for: Vision over visibility ✅ Can they spot future wins? 13. "Where do you see team friction?" Listen for: Insight over interest ✅ Will they surface hard truths? 14. "What information would help you?" Listen for: Clarity over confusion ✅ Do they know what they need? 15. "What should we stop doing?" Listen for: Courage over compliance ✅ Will they challenge the status quo? MOMENTUM (Progress & Patterns) 16. "Best improvement this quarter?" Listen for: Progress over perfection ✅ Do they build on wins? 17. "Where are we falling behind?" Listen for: Honesty over harmony ✅ Will they flag real risks? 18. "What problems keep returning?" Listen for: Patterns over problems ✅ Can they spot systemic issues? 19. "Which changes worked best?" Listen for: Learning over luck ✅ Do they study success? 20. "What one change helps most?" Listen for: Impact over activity ✅ Can they find leverage points? Remember:  The secret isn't in the questions. It's in the listening that follows. Thanks to Marsden Kline for the insightful carousel. Helpful?  🔔 Follow me (Dave Kline) for more.  ♻️ Repost to help others ask the right questions.

📢 Thinking Through Policy Uncertainty: A Strategic Imperative for Business Leaders In times of great geopolitical and policy uncertainty—like the one we are witnessing today—business leaders must sharpen their ability to distinguish the signal from the noise. With shifting alliances, evolving trade policies, economic fragmentation, and security risks shaping the global landscape, how should leaders consider what matters most? Here’s where to start: 🔹 Focus on Structural vs. Cyclical Change – Not all policy shifts have the same weight. Some are fundamental shifts in global power structures, while others are short-term political maneuvering. Leaders must ask: Is this a momentary disruption or a realignment that demands a strategic pivot? 🔹 Identify the Intent vs. the Impact – Governments make bold statements, but the real question is whether they have the political will, economic leverage, and regulatory mechanisms to implement those policies effectively. Bluster does not equal execution. Distinguish rhetoric from reality. 🔹 Look Beyond Borders – Policy changes in one country often trigger ripple effects across industries, supply chains, and markets. A new trade restriction, for example, doesn’t just affect exporters; it reverberates through global pricing, logistics, and investment strategies. 🔹 Scenario Planning, Not Guesswork – No leader has a crystal ball, but those who think through multiple contingencies will be best positioned for success. What happens if tariffs rise? If economic blocs realign? If new sanctions emerge? Having a strategy for different scenarios creates agility in uncertainty. 🔹 Follow the Money & Markets – Watch how capital moves. Global investors, multinational corporations, and financial markets often react before policies take full effect. If businesses are shifting supply chains or hedging investments, that’s a sign of where the real risks and opportunities lie. 🔹 Security, Stability & Strategic Foresight – Policy uncertainty isn’t just about commerce; it has deep implications for operational risk, cybersecurity, and corporate security strategies. Leaders must assess vulnerabilities beyond the balance sheet. The Bottom Line? In this era of uncertainty, success belongs to those who don’t just react but anticipate. Those who ask the right questions. Those who embrace complexity rather than fear it. The future isn’t predetermined—but strategic leaders shape how they navigate it. What’s your approach to policy uncertainty? Let’s discuss. 👇 #Geopolitics #BusinessStrategy #PolicyUncertainty #GlobalTrade #Leadership

Most leadership teams think in quarters. Futurist leaders think in cones. I'll explain how: This framework developed by futurist Amy Webb and published by Harvard Business Review urges leaders to ditch linear planning and instead adopt a cone of uncertainty that charts actions based on certainty, not just time. Because in today’s volatile, AI-accelerated, geopolitically tense world… You don’t just need a plan. You need a paradigm shift. Here’s what most organizations do: They obsess over 1-year targets and OKRs that make sense in a spreadsheet but collapse under systemic shocks — pandemics, climate disruptions, AI takeovers, or global talent shifts. They define success by what fits neatly into Q1–Q4. But strategic leaders, especially those building for the next decade — ask bigger, braver questions: -What future are we actually designing for? -What systems will break? Which will evolve? -Where will our industry no longer exist? The “Cone” Model in Action: > Tactics (1–2 years): This is your comfort zone driven by current data, financial certainty, and market feedback. This is where most companies feel confident. But it’s also where they get stuck. Leaders here ask: “What can we optimize?” > Strategy (2–5 years): This is where assumptions begin to stretch. Customer behaviors change. Talent expectations evolve. Competitors emerge from unexpected domains. Strategic leaders ask: “What plays are we making to stay ahead — not just survive?” > Vision (5–10 years): This is the clarity-deficit zone — less data, more imagination. It’s also where iconic companies start differentiating. Think: Microsoft betting on cloud in 2010. Or Tesla building an ecosystem, not just a car. Visionary leaders ask: “What could radically shift in our space — and how do we become the catalyst?” > Systems-Level Evolution (10+ years): This isn’t about your product. It’s about the world your product will operate in. Tech, policy, ethics, climate, social dynamics — all shift the ground you’ll one day stand on. Futurists ask: “What role do we want to play in shaping the future — not just reacting to it?” Best-in-class companies scenario-plan not just for risk, but for opportunity. They develop leadership that can think across the cone — not just in the next 12 months. They invest in foresight — not just analytics. According to Deloitte, only 17% of leaders feel confident in their organization’s long-term foresight capabilities. That’s not a stat. That’s a warning. So if you're a CEO, CHRO, or senior exec — ask yourself: ❌ Are we optimizing the present… ✅ Or are we architecting the future? The future will not wait for your 3-year plan to catch up. 👥 As an executive coach and advisor, I help senior leaders build systems thinking, cultivate futurist mindsets, and align vision with execution — across the cone. #StrategicForesight #FutureThinking #ExecutiveCoaching #VisionaryLeadership #FuturistStrategy #LongTermPlanning

What Every Leader Needs to Ask Before Saying “Yes” — And Why It Could Save You 10 Hours This Week As a leader, I used to say “yes” far too often. Yes to meetings. Yes to projects. Yes to opportunities that looked good, until they became distractions. Then one mentor asked me a question that shifted everything: “If you’re saying YES to this, what are you saying NO to?” That question saved me 10 hours in my first week of using it. No exaggeration. Here’s what I realized: Every YES costs time, energy, focus, and, most importantly, momentum. And momentum is a leader’s most valuable asset. Saying yes to that new project might mean saying no to focused time with your team. Saying yes to that partnership might mean saying no to strategic priorities that are already working. Strategy Tip: Before I commit to anything now, I write down two things: 1. What am I really agreeing to? (Time, team bandwidth, resources) 2. What is getting pushed aside as a result? It’s simple, but it’s transformed my calendar, my decision-making, and my team’s clarity. Why it works: This method creates built-in boundaries. And boundaries protect your long-term goals from short-term noise. When I was leading a major transition project, I got an invite to join a high-profile task force. Flattering? Yes. Smart? Not at the time. Saying no kept our rollout on track, under budget, and efficient. If you’re a leader of people, priorities, or performance, this mindset isn’t optional. It’s essential. Ask yourself this week: “If I say yes to this… what exactly am I saying no to?” Then decide like your time and influence depend on it, because they do. Let’s lead with clarity, not just activity. Because saying no is often the most strategic yes you’ll make. #LeadershipStrategy #DecisionMaking #TimeManagementTips

# 100 Days of Leadership - Day 7: The Power of Asking the Right Questions > "Leadership means asking the right questions. What problem does this AI solution solve?" In today's rapidly evolving technological landscape, leaders face a constant stream of vendors, solutions, and innovations promising to revolutionize their businesses. The true measure of leadership isn't in jumping on every trending bandwagon – it's in asking the penetrating questions that cut through the hype to reveal genuine value. When it comes to AI solutions, this principle becomes even more critical. We're witnessing a gold rush of AI implementations, with companies racing to integrate these technologies into their operations. However, effective leaders understand that technology should serve a purpose, not merely exist for its own sake. The question "What problem does this AI solution solve?" is deceptively simple yet profound. It forces us to: 1. Start with the problem, not the solution Rather than being dazzled by capabilities, we must first clearly articulate the challenge we're trying to overcome. Is there a genuine pain point that needs addressing, or are we simply attracted to the novelty of the technology? 2. Quantify the impact Understanding the problem allows us to measure the potential value of the solution. What metrics will improve? How will this impact our team's efficiency, our customer's experience, or our bottom line? 3. Consider the human element Every AI solution exists within a human context. How will this technology affect our workforce? What new skills will our team need to develop? How will this change our existing processes? Great leaders know that asking questions isn't a sign of ignorance – it's a demonstration of wisdom. They understand that their role isn't to have all the answers, but to ensure the right questions are being asked at the right time. This approach: ✅ Prevents costly investments in solutions searching for problems ✅ Ensures alignment between technology initiatives and business objectives ✅ Builds team engagement by modeling intellectual curiosity ✅ Creates a culture of thoughtful innovation rather than reactive adoption Remember, the quality of our questions determines the quality of our decisions. In the rush to embrace AI and other transformative technologies, the leaders who succeed will be those who pause to ask: "What specific problem are we solving, and is this truly the best way to solve it?" As you lead your organization through technological transformation, cultivate the habit of questioning. Challenge assumptions, dig deeper into proposed solutions, and never stop asking "why?" before asking "how?" Remember: Leadership isn't about having all the answers – it's about asking the questions that lead to better solutions. #100DaysOfLeadership

🔍 What If the Problem Isn’t the Problem? On Tuesday, I had a great conversation with one of the best leaders I know. We were wrestling with something that trips up even the most innovative teams: How do we keep from getting so caught up in today’s problems… that we lose focus on tomorrow’s challenges and opportunities? She leads with heart, urgency, and excellence. And like many top performers, she’s constantly solving problems, clearing roadblocks, and making things better for her team. But I challenged her, as I often do, to look 12+ months out, not just 12 hours ahead. Because leadership isn’t just about solving what’s right in front of you. It’s about helping your team see farther. Here’s the trap: 🥁 We solve what’s loud. 👀 We fix what’s visible. 🏃 We chase the problems we can solve because it’s satisfying. But the future isn’t built by fixing symptoms. It’s built by stepping back and asking the harder questions: • Why does this keep happening? • What’s the root system behind this pain point? • What are we ignoring while we’re putting out fires? Firefighting feels noble. But it can keep us stuck. Creating the future requires focus, courage, and the discipline to zoom out, even when the pressure is screaming at you to dive in. She and I agreed: it’s not easy. But it’s doable. And more than that, it’s necessary. Here’s how great leaders start shifting from reactive to strategic today: ✅ 1. Calendar the Future Block non-negotiable time every week to focus on problems 12+ months out. Even 90 minutes of protected time shifts your lens from tactical to transformational. Ask: “What are we doing today that impacts 12–24 months from now?” ✅ 2. Challenge Root Assumptions, Not Just Root Causes When problems repeat, don’t just ask why it happened. Ask why we think it’s normal. What if the real issue is the assumption behind the system? ✅ 3. Develop Future-Thinking Muscle in Your Team Bring others with you. Ask in 1:1s and team meetings: “How is this decision setting us up (or limiting us) a year from now?” You’ll build the habit, and the mindset, of strategic leadership across the team and the organization. Creating the future doesn’t start with solving the next fire. It starts with the courage to look beyond it. #CreateTheFuture #Leadership #StrategicThinking #ThinkLongTerm #SystemsThinking #ChallengeTheNorm #OrganizationalExcellence

Your next bad leadership hire won’t tank the company overnight. They’ll just quietly erode the team from the inside. Meetings get quieter. Momentum slows. Your best people stop speaking up, or leave. And on paper? They looked like a star. I’ve seen it. I’ve hired the brilliant-but-destructive exec. I’ve watched trust dissolve under leaders with sharp minds and shallow empathy. I’ve lived the cost of chasing credentials over character. Because here’s the truth: Raw intelligence doesn’t build great teams. Leadership does. And real leadership isn’t about having the best answers. It’s about making the team smarter, faster, safer, better. So now, when I help hire execs: VPs, Heads of, CXOs, I look for different signals. Not just track records. But how they lead when it’s hard. How they show up for others. How they amplify the system, not just their own shine. Here are 6 questions I now use, and why the've been game-changers for me: 1. “Tell me about a time you made someone on your team better?” This reveals if they’re an amplifier, the kind of leader who builds capacity in others. Not heroes. Not hoarders. Catalysts. 2. “When did you connect two teams or ideas that weren’t aligned?” The best leaders are connectors. They zoom out. They bridge gaps. They build shared momentum across silos. 3. “What’s a failure you’ve shared publicly with your team?” I’m testing for vulnerability here. Because if you can’t admit mistakes, you’ll never build psychological safety and without safety, there’s no innovation. 4. “Tell me about a time you took ownership for something that wasn’t totally your fault?” This separates the leaders from the deflectors. No hiding. No blaming. Just ownership. 5. “How do you respond when someone challenges your idea in front of others?” I want to know if they protect their ego, or the truth. Defensiveness kills learning. Great leaders invite challenge. And my very favorite one... 6. “Tell me about a time someone let you down.” This one stops people cold. It’s human. It’s raw. And it’s revealing. Because we’ve all been let down. By a colleague, a direct report, a boss. What matters is how you respond: Do you weaponize it? Do you withdraw trust? Or do you metabolize it with grace? This question shows me whether they can lead through disappointment without becoming cynical. It reveals if they’ve built emotional discipline, and whether they’ll hold people accountable without breaking them. The best leadership hires don’t just get results. They build systems of trust, accountability, and collective intelligence. They don’t need to be the smartest in the room, They need to make the room smarter. Because your next leadership hire is a financial decision. A cultural decision. A trust decision. And, as a great mentor of mine once told me: "In the end, the leaders you hire shape the culture you keep, and the results you earn".

The gap between good decisions and great ones often comes down to the questions we ask ourselves. 31% reduced confirmation bias. 39% improved argument quality. 43% greater hypothesis flexibility. These aren't just statistics. They're evidence of how the right questions can completely reshape your thinking. We're not in an era where critical thinking is optional. We're in a time where it's the difference between leading and following. The most powerful questions aren't complicated. They're precisely targeted to counteract our cognitive blind spots. Here are five backed by research: 🔹 "What would make me wrong about this?" Counteracts confirmation bias by forcing you to seek disconfirming evidence. Journal of Business Research shows this simple question improved decision accuracy by 26%. 🔹 "What's the strongest case against my position?" Develops intellectual empathy by steelmanning opposing views. Stanford University studies found this practice increased persuasiveness by 27%. 🔹 "What information would change my conclusion entirely?" Prevents overconfidence in limited evidence. Princeton University research shows this question improved the incorporation of new evidence by 51%. 🔹 "Whose perspective am I not considering?" Reveals blind spots and prevents echo chamber thinking. MIT Sloan School of Management research found this improved solution quality by 28%. 🔹 "How would I think about this if it weren't my idea?" Creates psychological distance from your own ideas. Organizational Research showed this reduced unhelpful attachment by 47%. The world doesn't just need more information processors. It requires more nuanced thinkers who can navigate complexity with clarity and objectivity. That's the mindset we're helping build - for leaders who want to make decisions they won't regret tomorrow. Coaching can help; let's chat.  Follow Joshua Miller 𝗟𝗶𝗸𝗲 𝘄𝗵𝗮𝘁 𝘆𝗼𝘂 𝗿𝗲𝗮𝗱 𝗯𝘂𝘁 𝘄𝗮𝗻𝘁 𝗺𝗼𝗿𝗲? 🚀 Download Your Free E-Book:  “𝟮𝟬 𝗦𝗺𝗮𝗹𝗹 𝗦𝗵𝗶𝗳𝘁𝘀 𝗧𝗵𝗮𝘁 𝗟𝗲𝗮𝗱 𝘁𝗼 𝗕𝗶𝗴 𝗟𝗶𝗳𝗲 𝗖𝗵𝗮𝗻𝗴𝗲𝘀” ↳ https://rb.gy/37y9vi #executivecoaching #criticalthinking #careeradvice