Mastering Strategic Planning

Every founder has a slide that says, “We’ll acquire customers through content marketing, paid social or partnerships.” And in 2025, nearly every investor has learned to ignore it 😿 The old go-to-market playbooks are not working anymore. The channels are saturated, the costs are high and the returns are diminishing. From where I sit as an early stage investor, a generic GTM plan is no longer a sign of preparation - it’s a red flag. It shows a founder is ready to execute someone else’s old strategy, not discover a new unique one tailored to their own business. Founders who are successful finding their first customers and raising capital are demonstrating something else entirely - not a polished plan, but a series of insightful discoveries. Here’s what I see actually working to prove you can access a market: ✔️ A Portfolio of Scrappy Experiments. Before you can find a scalable channel, you need to prove you can find ANY channel. The most impressive founders show up with stories of things that don't scale. They acquired their first 50 users by building a free tool that solved a tiny problem for their target user or by personally engaging in a specific Subreddit or Slack community. This proves you have the creativity and grit to find customers where others aren’t even looking. ✔️ A Founder Who Is the Distribution Channel. Early on, your most powerful GTM advantage can’t be bought because it’s actually YOU. Investors are looking for a founder with a unique ability to reach the market. Are you an expert with a following in your industry? Have you built a deep, trusted network that represents your initial customer base? Show how your personal brand and unique insights give you an unfair advantage that no amount of ad spend or marketing can replicate. ✔️ Mastery of a "Micro-Funnel." Instead of a broad, leaky funnel, demonstrate that you can dominate a tiny, efficient one. Prove that you can convert a very specific persona from a very specific source with incredible efficiency. For example: "We can turn a clinical research coordinator from a specific LinkedIn group into a qualified lead for $15." This level of precision is far more impressive than a vague, top-down plan to capture a massive market. It shows you have a data-driven foundation from which to grow. The goal of an early-stage GTM isn't to prove you can scale, it's to prove you can learn. Your first GTM strategy shouldn't be a playbook - it should be a lab notebook full of weird and (hopefully) winning experiments. 🙌🏼 Shout out to Alex Iskold from 2048 Ventures for teaching me a lot about funnels over the years and what he calls 'magic moments' 🙏🏼

Ever heard of the Lippitt-Knoster Model for Managing Complex Change? It's a classic in the change management world, laying out the essential pieces needed to navigate big transformations. Taking a cue from that, I've adapted it to fit the world of digital transformation. There are seven key elements you can't afford to miss: Vision, Strategy, Objectives, Capabilities, Architecture, Roadmap, and Projects & Programs. Skip any one of these, and you're asking for trouble. Here’s why each one matters: • 𝐕𝐢𝐬𝐢𝐨𝐧: This is the 'what' of your transformation. A clear vision gives everyone a target to aim for, aligning all efforts and keeping the team focused. • 𝐒𝐭𝐫𝐚𝐭𝐞𝐠𝐲: Think of this as the 'why' and 'how.' A solid strategy explains the logic behind your vision, showing how you plan to get there and why it's the best route. It’s designed to guide everyone in the company on how to make decisions that support the vision, aligning all efforts and keeping the team focused. • 𝐎𝐛𝐣𝐞𝐜𝐭𝐢𝐯𝐞𝐬: These are your milestones. Clear, specific objectives make it easy to measure success and ensure everyone knows what's important. Without them, you can easily veer off course and waste resources. • 𝐂𝐚𝐩𝐚𝐛𝐢𝐥𝐢𝐭𝐢𝐞𝐬: These are what your company will now be able to do that it wasn't able to before in order to achieve the objectives. These can be organizational capabilities (like improved decision-making), technical capabilities (such as real-time operational visibility), or other types like enhanced customer engagement or streamlined processes. • 𝐀𝐫𝐜𝐡𝐢𝐭𝐞𝐜𝐭𝐮𝐫𝐞: A robust architecture ensures all your tech works together smoothly, preventing inefficiencies and costly headaches. This includes various types of architecture such as data architecture, IT infrastructure architecture, enterprise architecture, and functional architecture. Effective architecture is central to reducing technical debt and aligning software with broader business transformation goals. • 𝐑𝐨𝐚𝐝𝐦𝐚𝐩: Your roadmap is the game plan. It lays out the sequence of actions, helping you avoid uncertainty and missteps. It's your guide to getting things done right. • 𝐏𝐫𝐨𝐣𝐞𝐜𝐭𝐬 & 𝐏𝐫𝐨𝐠𝐫𝐚𝐦𝐬: These are where the rubber meets the road. Actionable projects and programs turn your strategy into reality, making sure your plans lead to real, tangible outcomes. From my experience, I think '𝐂𝐚𝐩𝐚𝐛𝐢𝐥𝐢𝐭𝐢𝐞𝐬' and '𝐑𝐨𝐚𝐝𝐦𝐚𝐩' are the two most overlooked. What do you think? ******************************************* • Follow #JeffWinterInsights to stay current on Industry 4.0 and other cool tech trends • Ring the 🔔 for notifications!

The uncomfortable truth about creativity: why most businesses will fail in an AI-dominated future. Creativity may be discussed in countless strategy meetings, but excessive structure is its greatest enemy. Imagine a child learning to paint for the first time: - Given complete freedom, they create something unique and unexpected - Given strict rules and templates, they produce something technically correct but soulless It's no different for businesses and teams. In a world where AI can follow rules better than any human, our competitive advantage isn't in conformity - it's in creative divergence. Your goal shouldn't be to build perfect processes but to cultivate environments where innovation thrives naturally. Here's what truly creative organizations do differently: 1. They prioritize questions over answers They don't just reward people who solve problems - they celebrate those who identify new ones. 2. They create psychological safety Team members know unusual ideas won't be met with immediate judgment or dismissal. 3. They schedule time for play Creative breakthroughs happen in spaces between structured work - when minds are free to wander. 4. They embrace constraints, not controls They understand that some boundaries foster creativity, while excessive controls kill it. Every time you reject an unusual idea, enforce unnecessary bureaucracy, or dismiss playful exploration, you're closing doors to potential breakthroughs. The question isn't whether your team has creative potential - it's whether your systems are allowing that potential to flourish. What one change could you make today to better protect and nurture creativity in your organization? 👉 Follow me for more posts like this. 🔄 REPOST to help others.

If you’re building a company or trying to figure out how to grow it fast, this is for you. Today, we’re breaking down 7 GTM motions (with 28 guides) from top companies. And we've brought expert Maja Voje to help. Here’s your roadmap to mastering Go-to-Market: — 𝗔 𝗣𝗥𝗜𝗠𝗘𝗥 𝗢𝗡 𝗚𝗢-𝗧𝗢-𝗠𝗔𝗥𝗞𝗘𝗧 𝗠𝗢𝗧𝗜𝗢𝗡𝗦 When it comes to Go-to-Market (GTM), it’s all about the right combination of motions. From driving virality to closing enterprise deals, each motion is a tool that you can leverage to unlock growth. And while it may seem like a mystery, every successful GTM strategy shares key elements you can master: → What works at scale → Knowing where to focus → Scaling your team right — 𝗖𝗛𝗔𝗣𝗧𝗘𝗥 𝗢𝗡𝗘: 𝗕𝗥𝗘𝗔𝗞𝗜𝗡𝗚 𝗗𝗢𝗪𝗡 𝗧𝗛𝗘 𝗠𝗢𝗧𝗜𝗢𝗡𝗦 𝗢𝗙 𝗧𝗢𝗗𝗔𝗬'𝗦 𝗧𝗢𝗣 𝗚𝗥𝗢𝗪𝗘𝗥𝗦 We analyzed 12 of the hottest tech companies and found 3 common patterns: 1. PLG is taking over ↳ 80% of top companies now use (PLG) as their primary or a major supporting motion. ↳ Even enterprise giants like Salesforce are embracing it. 2. Multi-channel is essential ↳ No company relies on just one motion. ↳ On average, these companies use at least 3 channels to support growth. 3. ABM and Outbound are king for enterprise ↳ In high-ticket sales, Account-Based Marketing (ABM) and targeted outbound motions dominate. ↳ This is how five and six-figure deals get done. 𝗕𝗥𝗜𝗡𝗚𝗜𝗡𝗚 𝗜𝗧 𝗔𝗟𝗟 𝗧𝗢𝗚𝗘𝗧𝗛𝗘𝗥 → Start simple If you’re selling to consumers, lean on PLG, community, and partnerships early. → For SMBs Combine inbound and outbound motions for awareness and relationship-building. → For Enterprises Focus on ABM and outbound, with inbound as a support. — 𝗖𝗛𝗔𝗣𝗧𝗘𝗥 𝗢𝗡𝗘.𝗢𝗡𝗘: 𝗛𝗢𝗪 𝗧𝗢 𝗞𝗡𝗢𝗪 𝗪𝗛𝗜𝗖𝗛 𝗠𝗢𝗧𝗜𝗢𝗡𝗦 𝗧𝗢 𝗣𝗥𝗜𝗢𝗥𝗜𝗧𝗜𝗭𝗘 1. Talk to your customers ↳ Find out how your buyers made their last purchasing decision, including the channels they used and decision drivers. ↳ Ask what content, demos, or touchpoints had the most impact on their decision. 2. Research your competition ↳ Use tools like SimilarWeb, SEMRush, and BuiltWith to analyze your competitors' traffic sources , GTM motions, and untapped opportunities. 3. Play on your strengths ↳ Assess the channels where your team already has proven skills and experience and double down on it first. 4. Select 2-3 GTM motions to test ↳ Prioritize the channels that align best with your product and target audience for the highest potential ROI. 5. Stick with them for 1-3 months ↳ Track progress consistently, making data-driven adjustments without switching strategies too quickly and iterate on what works. — 𝗖𝗛𝗔𝗣𝗧𝗘𝗥 𝗧𝗪𝗢: 𝗧𝗪𝗘𝗡𝗧𝗬 𝗘𝗜𝗚𝗛𝗧 𝗚𝗨𝗜𝗗𝗘𝗦 𝗕𝗬 𝗠𝗢𝗧𝗜𝗢𝗡 If you want to master all 7 motions — with detailed breakdowns, examples, swipe files, and the tools to execute them — the breakdown is in the comments 👇.

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?

Here’s why sharing strategic thinking “frameworks” without context is useless (and what actually works). I see posts like this infographic daily on social media—pretty boxes, buzzwords… and zero actionable insight. The brutal truth? Posting frameworks without explanation is career virtue signaling at its worst. Strategic Thinking Is actually critical right now: ✅ 57% of business leaders say strategic thinking is the #1 soft skill their workforce desperately needs (Springboard 2024) ✅ The World Economic Forum 2025 Future of Jobs Report confirms analytical thinking remains the TOP core skill demanded by 7 out of 10 companies globally. While everyone’s obsessing over AI and technical skills, the most successful professionals are the ones who can think strategically about those tools. Here are 5 ways I coach my clients to actually develop their strategic thinking which you can adopt right now: 1. Master the “So What?” Question After every data point, analysis, or meeting, → Ask, “So what does this mean for our goals?” Force yourself to connect dots, not just collect them. 2. Practice Scenario Planning Weekly Pick one business decision facing your team. Map out 3 potential outcomes and their implications. This builds your strategic foresight muscle. 3. Reverse-Engineer Successful Strategies Study companies that solved problems similar to yours. What assumptions did they challenge? What patterns can you extract? 4. Create a “Strategic Time Block” Block 2 hours weekly for big-picture thinking. No emails, no tactical work. Just strategic reflection and planning. Non-negotiable. 5. Teach Your Thinking Process Explain your strategic reasoning to others. If you can’t teach it clearly, you haven’t thought it through deeply enough. Strategic thinking isn’t about memorizing frameworks from infographics on Pinterest. It’s about developing the mental discipline to see patterns, challenge assumptions, and connect seemingly unrelated pieces. The professionals who master this will be irreplaceable. The ones who share pretty frameworks will be forgotten. Which one are you? Coaching can help; let's chat. | Joshua Miller #executivecoaching #professionaldevelopment #careeradvice #getahead

Why a Plan is NOT a Strategy 👇 Most people think planning and strategy are the same thing, but here’s the reality: A plan without strategy is just busy work. 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆 (𝗟𝗼𝗴𝗶𝗰) 1. Vision & Goals ↳ Where are you going? What’s your ultimate goal? 2. Core Objectives ↳ What high-level moves will get you there? 3. Key Priorities ↳ What matters most right now? Focus your energy. 4. Resources & Capabilities ↳ Do you have what you need? If not, how will you get it? 5. Adaptive Decisions ↳ Be ready to pivot. Strategy is fluid and it evolves with new information. 𝗣𝗹𝗮𝗻𝗻𝗶𝗻𝗴 (𝗣𝗿𝗼𝗰𝗲𝘀𝘀) 1. Detailed Steps ↳ Break down specific tasks to accomplish your goal. 2. Fixed Timeline ↳ Set deadlines, but know they can be rigid. 3. Budget Allocation ↳ Lock in your resources for execution. 4. Milestone Tracking ↳ Check your progress against fixed benchmarks. 5. Execution ↳ Implement step-by-step, with little room for deviation. Here’s where people get it wrong: 👉 Strategy is your WHY and WHAT. It’s the art of navigating uncertainty, setting direction, and adapting as you go. 👉 Planning is your HOW. It’s the process of executing tasks within a timeline—often without flexibility. Strategy asks: Are we climbing the right mountain? Planning says: Here’s how to climb. Remember: You can’t execute your way out of a bad strategy. And strategy without action is just wishful thinking. 💬 P.S: Which one do you need to work on more: Strategy or Planning? ___ ✨ Follow me, Hetali Mehta, MPH for more strategic insights. ♻️ Share this post with someone who’s ready to think bigger and level up their approach!

Strategy is derived from the bottleneck. Strategy must "bust" the bottleneck. The bottleneck is the constraint that limits progress toward the aspiration of the organization. The bottleneck can be thought of as a barrier, obstruction, limitation, impediment, obstacle, or hindrance; it doesn’t matter the word you use or the image in your head. Technically, the bottleneck is the 𝘀𝘆𝘀𝘁𝗲𝗺 𝗰𝗼𝗻𝘀𝘁𝗿𝗮𝗶𝗻𝘁.* And unless the system constraint is reduced, the system does not change. The bottleneck can be of a wide range of character, as shown in the figure, including cultural issues. Culture is an organization's habits, the scripts people follow when responding to the internal and external world. True strategies are rarely just a laundry list of business plan choices like markets, products, and customers. A business plan is not a strategy in most cases. So, if the cultural issue is too much adherence and obedience to leadership with no pushback or fight, the leader’s strategy might revolve around promoting the few people who do push back, bringing in people from the outside who do have fight in them, or using retreats or other formats to show people the kind of fight she is looking for. If the cultural issue is that the organization accepts low-quality, superficial work presented in long PowerPoint presentations filled with forecasts, lists of initiatives, and talk of transformations and other buzzwords, then her strategy may revolve around creating new standards—either by working with the few people who can do it internally, or bringing in some help—and then ramping up the firing of people who do no show the aptitude or inclination to meet the new standards. If the bottleneck is that the product line and operations have become way too complicated, with too many product platforms and SKUs, convoluted ways of making these products, and special cuts and special treatment for customers who may no longer deserve them, then the strategy would be completely different. If the bottleneck to achieving the organization's aspiration is related to business model issues, like a declining market, new competition, or new opportunities, the strategy would, again, be different. Bottleneck dictates strategy, and aspiration dictates bottleneck. -------------------- * The Theory of Constraints uses the term bottleneck for other types of constraints, but the concept of system constraint is the same in the Emergent Approach to Strategy and the Theory of Constraints. #EmergentApproach #PeterCompo #AdaptiveStrategy #EmergentStrategy #StrategyDesign

Most CEOs aren’t bad at strategy because they lack intelligence. They’re bad at it because they’ve been trained to think in straight lines — when real strategy demands curves, contradictions, and creativity. Roger Martin — one of the sharpest strategy minds of our time — nails it: “A good strategy is the product of the creative combination of two disparate logics…” But most executives? They’ve been rewarded their whole lives for being analytical — not integrative. For minimizing risk — not imagining a better play. For optimizing what exists — not redefining what could be. - You can’t spreadsheet your way into a market no one has built yet. - You can’t data-model a future your competitors haven’t imagined. - You can’t “analyze” your way into a breakthrough. You need to suspend logic long enough to see the world differently — and then bring logic back in to make it real. That’s the creative tension great strategy lives in. ✅ Bad strategy logic: “We’ll win in EVs by matching Tesla’s range and price.” That’s copycat thinking. It’s linear. It’s a race you’re entering on someone else’s track. ✅ Creative strategy logic: “What if EVs were not just cleaner — but customizable, subscription-based, and controlled by AI assistants that learn your habits?” That’s what Nio did in China. They didn’t beat Tesla at Tesla’s game. They changed the game. ✅ Bad strategy logic: “We’ll scale by increasing marketing spend 10% and expanding into 3 new cities.” That’s spreadsheet strategy. Logical? Sure. But it’s just operational efficiency wearing a blazer. ✅ Creative strategy logic: “What if we turn our most loyal customers into micro-franchisees with revenue share?” That’s what Meesho did in India — creating millions of sellers without building a sales team. Most CEOs can run a company. Very few can reinvent one. Because the skill that got them to the top — linear logic, risk control, system thinking — is the same skill that blocks real strategic creativity. What can you do as a leader? ✅ Practice integrative thinking — hold opposing ideas without rushing to collapse one. ✅ Encourage wild assumptions during planning — then test them. ✅ Hire for imagination, not just experience. ✅ Get a coach or thought partner who doesn’t think like you. Strategy isn’t what you put in a deck. It’s how boldly you allow disparate logics to collide… And still commit to building something the world hasn’t seen yet. 👥 I coach senior leaders to step beyond the comfort of logic and into the discomfort of bold possibility. Because the future isn’t built by the most logical — it’s built by the most courageous. #ExecutiveCoaching #StrategicThinking #LeadershipDevelopment #DisruptiveStrategy #RogerMartin #CreativeLeadership #GeorgeSpeaks

Too often, I’ve been in a meeting where everyone agreed collaboration was essential—yet when it came to execution, things stalled. Silos persisted, friction rose, and progress felt painfully slow. A recent Harvard Business Review article highlights a frustrating truth: even the best-intentioned leaders struggle to work across functions. Why? Because traditional leadership development focuses on vertical leadership (managing teams) rather than lateral leadership (influencing peers across the business). The best cross-functional leaders operate differently. They don’t just lead their teams—they master LATERAL AGILITY: the ability to move side to side, collaborate effectively, and drive results without authority. The article suggests three strategies on how to do this: (1) Think Enterprise-First. Instead of fighting for their department, top leaders prioritize company-wide success. They ask: “What does the business need from our collaboration?” rather than “How does this benefit my team?” (2) Use "Paradoxical Questions" to Avoid Stalemates. Instead of arguing over priorities, they find a way to win together by asking: “How can we achieve my objective AND help you meet yours?” This shifts the conversation from turf battles to solutions. (3) “Make Purple” Instead of Pushing a Plan. One leader in the article put it best: “I bring red, you bring blue, and together we create purple.” The best collaborators don’t show up with a fully baked plan—they co-create with others to build trust and alignment. In my research, I’ve found that curiosity is so helpful in breaking down silos. Leaders who ask more questions—genuinely, not just performatively—build deeper trust, uncover hidden constraints, and unlock creative solutions. - Instead of assuming resistance, ask: “What constraints are you facing?” - Instead of pushing a plan, ask: “How might we build this together?” - Instead of guarding your function’s priorities, ask: “What’s the bigger picture we’re missing?” Great collaboration isn’t about power—it’s about perspective. And the leaders who master it create workplaces where innovation thrives. Which of these strategies resonates with you most? #collaboration #leadership #learning #skills https://lnkd.in/esC4cfjS