Long-Term Strategic Planning

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 future feels more uncertain than ever… Here’s a playbook to thrive (my Lighthouse Strategy): Let's begin with a simple truth: Uncertainty is the only certainty. There's a tendency to say "this time is different" with every major event, but while the specifics are always different, as a student of history, you cannot ignore the general similarities. Uncertainty has always been the norm. The one who can tolerate and embrace the most uncertainty is the one who will eventually win. To become this ONE, you first need to recognize that the Old Model (plan, execute) is broken. The New Model is a perpetual loop: • Execute: Take action, move, create, build • Adapt: Gather info, think, learn, adjust This New Model is the foundation of a mindset to thrive in an uncertain future. But the mindset alone is not enough. How do we prepare, what skills do we build, and what do we focus on to win in this uncertain future? Time to dive in on my Lighthouse Strategy... A lighthouse serves one simple but profound purpose: To guide sailors safely through uncertainty. It warns of dangers, provides orientation, and offers a single point of focus to navigate through storms or darkness. The conditions may change, but the lighthouse never does. In 2012, Amazon founder Jeff Bezos shared this insight about building for the future: "I very frequently get the question: 'What’s going to change in the next 10 years?' And that is a very interesting question; it’s a very common one. I almost never get the question: 'What’s not going to change in the next 10 years?' And I submit to you that that second question is actually the more important of the two." The lesson: It's easy to focus on what will change, but in a world where it's unlikely you will be correct, it's more important to focus on what will stay the same. Here are a few timeless human truths that will not change in the future: • Humans will want real connection • Humans will want to consume things • Humans will be seeking meaning • Humans will pay for things that reduce friction • Humans will seek out status These truths are the lighthouse. Further, there are timeless skills—those that are likely to remain valuable and relevant across a wide array of future states. I call these Lighthouse Skills: • Sales • Storytelling • Clear Communication • Emotional Intelligence • Public Speaking • Taste • Clear Thinking The goal is to focus on developing a set of skills and attributes that are relevant and valuable in a range of potential futures. These Lighthouse Skills pass the test. Use this playbook as a frame of reference to navigate the inevitable storms that come—you’ll be well equipped to see your way to the other side. To go deeper to create the life you want, order a copy of my 7x NYT bestselling book, The 5 Types of Wealth. It has a 30% sale right now: https://lnkd.in/eEvFnNr3 P.S. Share this post with someone it may help.

I wish someone taught me this in my first year as a PM. It would’ve saved years of chasing the wrong goals and wasting my team's time: "Choosing the right metric is more important than choosing the right feature." Here are 4 metrics mistakes even billion-dollar companies have made and what to do instead with Ron Kohavi: 1. Vanity Metrics They look good. Until they don’t. A social platform he worked with kept showing rising page views… While revenue quietly declined. The dashboard looked great. The business? Not so much. Always track active usage tied to user value, not surface-level vanity. 2. Insensitive Metrics They move too slowly to be useful. At Microsoft, Ronny Kohavi’s team tried using LTV in experiments. but saw zero significant movement for over 9 months. The problem is you can’t build momentum on data that’s stuck in the future. So, use proxy metrics that respond faster but still reflect long-term value. 3. Lagging Indicators They confirm success after it’s too late to act. At a subscription company, churn finally spiked… but by then, 30% of impacted users were already gone. Great for storytelling but let's be honest, it's useless for decision-making. You can solve it by pairing lagging indicators with predictive signals. (Things you can act on now.) 4. Misaligned Incentives They push teams in the wrong direction. One media outlet optimized for clicks and everything was looking good until it wasn't. They watched their trust drop as clickbait headlines took over. The metric had worked. They might had "more MRR". But the product suffered in the long run. It's cliche but use metrics that align user value with business success. Because Here's The Real Cost of Bad Metrics - 80% of team energy wasted optimizing what doesn’t matter - Companies with mature metrics see 3–4× stronger alignment between experiments and outcomes - High-performing teams run more tests but measure fewer, better things Before you trust any metric, ask: - Can it detect meaningful change in faster? - Does it map to real user or business value? - Is it sensitive enough for experimentation? - Can my team interpret and act on it? - Does it balance short-term momentum and long-term goals? If the answer is no, it’s not a metric worth using. — If you liked this, you’ll love the deep dive: https://lnkd.in/ea8sWSsS

Are Family Offices Ready for Market Turbulence? Market volatility and persistent uncertainty dominate the current investment climate. Most Family Offices anticipated these conditions and strategically positioned themselves ahead of disruptions. The UBS Global Family Office Report 2025 illustrates how these investors effectively transform volatility into opportunity. Top Risks Family Offices Monitor: • Geopolitical Conflict (52%): Middle East tensions, notably involving Iran, have disrupted energy markets and global supply chains, prompting many Family Offices to recalibrate strategies quickly. • Global Trade War (70%): US-China trade disputes are inflating costs and impacting profitability, making this a top priority for strategic adjustments. Family Offices are proactively addressing potential long-term economic challenges: • Global Recession (53%): Inflation and geopolitical tensions indicate a looming economic slowdown, prompting portfolio adjustments. • Debt Crisis (50%): Interest rate hikes have exposed financial vulnerabilities, leading Family Offices to emphasize proactive debt management. • Climate Change & Market Volatility (48% & 46%): Climate concerns are increasingly central to investment planning and risk strategies. Strategies Family Offices Implement for Resilience: • Active Management (40%): Leveraging experienced managers to navigate market shifts effectively. • Hedge Funds (31%): Using hedge funds to protect assets and secure stable returns. • Illiquid Assets (27%): Investing in private markets to maintain consistent, long-term growth. • Precious Metals & Short-Term Bonds: Diversifying with safe-haven assets like gold (19%) and short-duration bonds (26%) for stability. Despite careful planning, Family Offices face challenges in identifying reliable risk strategies in today's uncertain markets. Their strategic adaptability remains key to long-term wealth preservation. Consider: Is your investment strategy aligned with leading Family Offices? Are you ready not just to withstand, but thrive in turbulence? Success in uncertain times hinges on foresight, flexibility, and preparation. Data adapted from the UBS Global Family Office Report 2025. Context updated for June 2025. This analysis is for informational purposes and is not investment advice.

How to Extract Information from Stakeholders 🎯 Getting accurate information from stakeholders can make or break your financial planning process. Each stakeholder speaks a completely different language and focuses on totally different metrics. The secret? Knowing exactly what to ask and how to ask it. ➡️ CEO CONVERSATIONS CEOs think big picture, so focus on strategic direction and vision. You want company strategies for next quarter, budget allocation expectations, risk tolerance levels, and market positioning goals. The money question: "What are the top 3 strategic priorities that should drive our Q4 planning?" ➡️ HEAD OF SALES Sales leaders live and breathe pipeline projections and customer acquisition costs. Get those sales pipeline projections, customer acquisition costs, territory performance data, and resource requirements for targets. My go-to approach: "What's the realistic revenue projection for Q4, and what support do you need?" ➡️ MARKETING DIRECTOR Marketing lives for lead generation and brand metrics. You need campaign performance metrics, lead generation forecasts, brand awareness initiatives, and marketing budget requirements. Hit them with: "How many qualified leads can marketing deliver to support the sales targets?" ➡️ HR MANAGER HR thinks talent and workforce planning 24/7. Grab headcount projections, recruitment timelines, employee retention rates, and training and development needs. Start here: "What's our hiring timeline to support the growth plan, and any retention concerns?" ➡️ ENGINEERING LEAD Engineering leaders obsess over product development roadmaps. Collect that product development roadmap, technical debt priorities, infrastructure requirements, and team capacity information. The must-ask question: "What features can be delivered by Q4, and what technical investments are critical?" ➡️ ACCOUNTING MANAGER Accounting thinks financial health and compliance every single day. Get cash flow projections, budget variance analysis, financial compliance requirements, and cost optimization opportunities. The essential question: "What's our cash flow outlook, and are there any financial constraints for our growth plans?" ➡️ UNIVERSAL BEST PRACTICES These six practices work with EVERY stakeholder: Be Specific: Ask for concrete numbers, dates, and measurable outcomes rather than vague commitments. Respect Their Time: Come prepared with focused questions and provide context upfront. Speak Their Language: Use terminology and metrics relevant to their department and priorities. Validate Understanding: Repeat back key points to ensure alignment and avoid miscommunication. Follow Up: Send summaries of key decisions and next steps within 24 hours. Close the Loop: Show how their input directly influences decisions and outcomes. === What's your approach to stakeholder communication? Share your best practices in the comments below 👇

Are your ESG initiatives just feel-good projects, or part of a strategic program? Many companies fall into the trap of implementing random environmental or social efforts—like reducing paper use or launching a one-off green campaign—without tying them back to a bigger plan. These isolated acts might look good on paper but often lack long-term impact. That’s where an intentional ESG strategy comes in. Instead of scattered efforts, a well-crafted strategy aligns with your company’s core values, business goals, and culture. It’s not just about doing good; it’s about ensuring that every initiative is purposeful and contributes to the overall mission of the organization. I’ve worked with organizations where the first step in building an ESG strategy was reviewing their mission statement and values. When these elements serve as the foundation, the ESG program becomes a natural part of the organization, not a side project. From there, the real work begins: setting specific, measurable, and realistic goals. Take, for example, A company targeting net-zero carbon emissions by 2030. This isn’t a vague aspiration—it’s a concrete goal that can be tracked, measured, and reported. Using frameworks like the Science Based Targets initiative (SBTI) or the UN Sustainable Development Goals (SDGs) can help ensure that your goals are in line with global standards, making it easier to measure progress. But it doesn’t stop there. A successful ESG strategy requires ongoing commitment and alignment with stakeholder expectations. Regularly assessing progress and engaging key players—whether they’re investors, employees, or customers—helps keep the strategy relevant and impactful. So, Is your company making random ESG efforts, or are you crafting a strategy that reflects your values and drives real change? #ESG #Sustainability #BusinessStrategy #EnvironmentalImpact #CorporateResponsibility

Chubbies' nine-figure acquisition and ten-figure IPO didn’t happen by chasing ROAS. Focusing solely on short-term revenue almost cost us everything. Changing our marketing metrics to focus on long-term profit transformed our growth quality and became a key driver of equity value Here are the mistakes, lessons, and actions you can take today btw, I was the '1-day-click-revenue-or-nothing' guy for embarrassingly too long, but my loss is your gain, so here are: 1) Three mistakes and lessons 2) Three ways to update your thinking on the topic, and 3) Three actions to consider today let's do it Three mistakes and lessons 1. Maximizing Revenue and ROAS has little connection to growing fundamental equity value. Increasing them doesn’t always grow cash generation since there's no incorporation of the costs to get that growth 2. Beyond product, team, and execution, asset value came from a growing base of organic acquisition (the Brand). Performance marketing mattered, but Brand drove value 3. Revenue growth is great for the ego, but it's more about quality of growth than quantity. Ultimately, your growth story must show evidence of, and a clear path to, sustained long-term profit growth Three ways to update your thinking on the topic 1. Brand vs Performance is a false dichotomy. When building a house, foundation vs finishes isn't even a debate. You want a house, and it's obvious that you need the foundation, framing, plumbing (the stuff you don't see) AND the stuff you DO see, like the facade and the finishes. Brand is like a house—you need all the parts. Without a foundation (Brand), there’s no facade or finishes (Performance), no matter how much you want to focus on the sexy, visible stuff 2. It's not just about equity value, it's about architecting your success criteria around building a machine that, with each passing year, spits out more and more cash after going through every single line in the P&L. Revenue and ROAS play no role here 3. While there are blips where you find increased efficiencies, performance marketing alone always gets more expensive over time. Brand is the only way to bring acquisition costs down over time Three actions to consider today 1. Take an hour tomorrow to do some soul searching. Ponder this question: Are your current measures of success as closely tied to fundamental business quality and equity value improvement as possible? 2. If the answer is NO, meet w/ the team to plan how to gradually shift the KPIs that define success and drive compensation. 3. Long-term profit comes from being memorable, not tinkering with Ads Manager. Ask yourself: What makes your brand bold, fun, and unforgettable? This builds organic acquisition and turns you from a flash-in-the-pan to a generational asset hope this helps ✌️❤️🤘

Here’s the truth: Deals win or die by what happens after close. M&A isn’t just about numbers. It’s about envisioning the end state. I’ve seen too many deals get done for the wrong reasons—chasing revenue, ego, or momentum—without ever asking: What do we want this to look like after the dust settles? That’s why Buyer-Led M&A flips the script. We lead with clarity, not chaos. 🔹 Start by mapping the end state. Not just the financials—think operating model, customer experience, and decision-making structure. What does “success” actually look like? 🔹 Then dig into culture. Forget the surface-level values page. You need to understand how decisions get made, how people work, and how priorities shift under pressure. That’s the real culture. 🔹 Now you can start building a joint go-to-market plan. This is your integration thesis. What does the customer experience look like as a combined company? 🔹 Integration planning should run parallel to diligence. Same team. Shared information. Continuous learning. That’s how you get to Day 1 readiness—and avoid repeating diligence after you’ve already bought the company. 🔹 Finally: reverse diligence. Let the target get to know you. This is a two-way street. The more transparency, the more alignment, the more likely you’ll retain the people who actually make the deal work. M&A isn’t a race to term sheets. It’s a race to value creation—and that starts by leading the process, not just following it. This is how I define the Buyer-Led M&A™ mindset. What am I missing? Let me know in the comments. #MergersAndAcquisitions #BuyerLedMA #DealRoom

Businesses don't fail because they lack a great idea. They fail because they can't get enough forward airspeed to soar. 𝗜 𝘀𝗲𝗲 𝗮 𝗿𝗲𝗰𝘂𝗿𝗿𝗶𝗻𝗴 𝗽𝗮𝘁𝘁𝗲𝗿𝗻: - Founders have a great idea for changing the world. - They bootstrap to work with innovators. - Everyone is a potential customer. - Early success is mistaken for market demand. - The end of the runway comes before sustained flight. -------------------------------------------------------- How to transform a struggling business toward sustainable growth and lasting impact. --------------------------------------------------------  1. 𝗦𝗼𝗹𝘃𝗲 𝗯𝗶𝗴 𝗽𝗿𝗼𝗯𝗹𝗲𝗺𝘀 - I will guide you in identifying problems that customers will pay you to address.  2. 𝗕𝗲 𝗰𝗹𝗲𝗮𝗿 𝗮𝗯𝗼𝘂𝘁 𝘆𝗼𝘂𝗿 𝘃𝗮𝗹𝘂𝗲 - We will work together to create messaging and stories that drive buyers to contact you.  3. 𝗥𝗲𝗳𝗶𝗻𝗲 𝘆𝗼𝘂𝗿 𝗜𝗖𝗣 𝗮𝗻𝗱 𝗦𝗲𝗴𝗺𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 - I'll help you bring clarity to your ideal customer profile and we'll identify your total relevant market.  4. 𝗗𝗲𝘁𝗲𝗿𝗺𝗶𝗻𝗲 𝘄𝗵𝗲𝗿𝗲 𝘁𝗼 𝗽𝗹𝗮𝘆 𝗮𝗻𝗱 𝗵𝗼𝘄 𝘁𝗼 𝘄𝗶𝗻 -  We'll develop a playbook to engage your ICP and provide them with valuable experiences at each touchpoint with your company.  5. 𝗠𝗼𝘃𝗲 𝗱𝗲𝗹𝗶𝗯𝗲𝗿𝗮𝘁𝗲𝗹𝘆 𝗮𝗻𝗱 𝗾𝘂𝗶𝗰𝗸𝗹𝘆 - I default to being action-oriented. We will build consensus using the best available insights and move quickly.  Observe, Orient, Decide, and Act.  6. 𝗙𝗼𝗰𝘂𝘀 - We won't do everything, just the right things. You have precious few resources. We will use them wisely.  7. 𝗣𝗶𝘃𝗼𝘁 𝘁𝗼 𝗮𝘃𝗼𝗶𝗱 𝗹𝗼𝘀𝘀 - When headwinds and crosswinds threaten your safety, we'll pivot the course while maintaining your long-term destination in sight.  8. 𝗕𝘂𝗶𝗹𝗱 𝗮 𝗰𝘂𝘀𝘁𝗼𝗺 𝗳𝗹𝘆𝘄𝗵𝗲𝗲𝗹 - Sustainable growth comes from building effective and efficient processes. We'll build cross-functional workflows that create value and profits.  9. 𝗕𝘂𝗶𝗹𝗱 𝗮 𝗿𝗲𝗴𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝘃𝗲 𝗲𝗰𝗼𝗻𝗼𝗺𝗶𝗰 𝗺𝗼𝗱𝗲𝗹—As we gain traction, it is crucial to expand our thinking about leveraging our success to benefit others. This is the path to sustainable growth and lasting impact. 10. 𝗡𝘂𝗿𝘁𝘂𝗿𝗲 𝗻𝗲𝘄 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 - Running a business can be exhausting. When it's time to delegate, we'll build processes to sustain your vision and effectiveness through others. I'd like to talk with you if you're looking to add a growth advisor to your startup or scaleup. Let's talk about your vision and what's keeping you from growing.  Send me a DM to arrange a call. #fractionalcmo #gtm #businessgrowth  

Far too often, I see leaders and companies move on from innovation, believing it's only necessary during the startup phase. In reality, it's what keeps companies alive and thriving. As companies grow, it's easy to fall into routine and let creativity fade. But innovation must continue-even as you scale. An older HBR article I came across this morning highlights how breakthroughs in management can create lasting advantages that are hard to replicate. Companies focused only on new products or efficiency often get quickly copied. To stay ahead, businesses must become "serial management innovators," always seeking new ways to transform how they operate. This idea remains as relevant now as it was back then. The benefits of sustained innovation are undeniable: •Competitive Edge •Increased Revenue •Customer Satisfaction •Attracting Talent •Organizational Growth and Employee Retention Embrace the innovation lifecycle-adapting creativity as your organization matures. Sustaining creativity means creating an environment where people feel safe to push boundaries. Encourage your teams to think big, take risks, and use the experience of your organization. Here are three strategies that I’ve seen work firsthand: Make Experimentation a Priority: Mistakes are part of the process—they help us learn, grow, and innovate. As leaders, share your own experiences with risk-taking, talk about what you've learned, and celebrate those who take bold steps, even when things don’t go as planned. It sends a powerful message: it's okay to take risks. Promote Intrapreneurship: Many of the best ideas come from those closest to the work. Encourage your people to think like entrepreneurs. Give them ownership, the tools they need, and the freedom to explore. Whether it’s through ‘innovation sprints’ or dedicated time for passion projects, showing your team that their creativity matters sustains momentum. Address big challenges, ask tough questions, and let your people feel empowered to tackle them head-on. Break Down Silos: True innovation happens when people connect across departments. Create opportunities for cross-functional interactions-through gatherings, open forums, or spontaneous connections. Diverse perspectives lead to game-changing solutions, and breaking down silos opens the door to that kind of synergy. Innovation doesn’t happen by accident. It requires dedication, a commitment to growth, and a willingness to challenge what’s always been done. To all the leaders out there: How are you ensuring your teams remain creative and engaged? What strategies have you found that create space for bold ideas within structured environments? —-- Harvard Business Review, "The Why, What, and How of Management Innovation" #Innovation #Leadership #ContinuousImprovement #Creativity #BusinessGrowth #Intrapreneurship #CrossFunctionalCollaboration #ImpactLab