Strategic Initiative Management

𝗜𝘀 𝘆𝗼𝘂𝗿 𝗽𝗿𝗶𝗼𝗿𝗶𝘁𝘆 𝗶𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 𝘁𝗿𝘂𝗹𝘆 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰? One of my favorite tools to test this is a “reverse 5 whys.” You might know the original 5 whys exercise: Start with the problem and ask “why?” 5 sequential times to find its root cause instead of ‘treating the symptoms.’ But the reverse 5 whys goes the opposite direction. Start with a single initiative or priority, and ask “why” 5 times, zooming out to a broader perspective each time. This exercise can strengthen the strategic rationale of your recommendation - tying a singular ground level action with the higher level strategy and objectives. This method is especially helpful when making decisions between two attractive initiatives. Just because an investment or project would be profitable, doesn’t mean that's the best use of resources. For example, imagine your team is considering participating in a major industry trade show. • 𝗪𝗵𝘆 𝘁𝗵𝗶𝘀 𝗶𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲? To increase brand awareness. • 𝗪𝗵𝘆 𝘁𝗵𝗶𝘀 𝘀𝗵𝗼𝘄? It attracts a new segment of target customers that we want to reach. • 𝗪𝗵𝘆 𝗳𝗼𝗰𝘂𝘀 𝗼𝗻 𝘁𝗵𝗲𝘀𝗲 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿𝘀? This segment is growing faster than others and aligns with our strategic bet on where market demand is headed. • 𝗪𝗵𝘆 𝗮𝗿𝗲 𝘄𝗲 𝗽𝗼𝘀𝗶𝘁𝗶𝗼𝗻𝗲𝗱 𝘁𝗼 𝘄𝗶𝗻 𝘄𝗶𝘁𝗵 𝘁𝗵𝗶𝘀 𝘀𝗲𝗴𝗺𝗲𝗻𝘁? They have an unmet need that we address better than the competition (like Oura Ring focusing on women’s health). • 𝗪𝗵𝘆 𝗱𝗼𝗲𝘀 𝘁𝗵𝗶𝘀 𝗺𝗮𝘁𝘁𝗲𝗿 𝗳𝗼𝗿 𝗼𝘂𝗿 𝗳𝘂𝘁𝘂𝗿𝗲? This segment will position us as the go-to provider for [X solution]. Now, instead of just “let’s go to a trade show,” the initiative ties directly to a strategic bet—winning in a high-growth market by leveraging your competitive advantage for a specific customer need. A strong recommendation doesn’t just explain what to do. It answers why this initiative matters in the long-term context. The reverse 5 whys reveals: Is this just a tactical decision (addressing short-term needs), or a step toward our desired future state? 𝗪𝗵𝗲𝗻 𝘆𝗼𝘂’𝗿𝗲 𝗳𝗮𝗰𝗲𝗱 𝘄𝗶𝘁𝗵 𝗮 𝗻𝗲𝘄 𝗶𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲, 𝗮𝘀𝗸 𝘆𝗼𝘂𝗿𝘀𝗲𝗹𝗳: • What am I really trying to accomplish here? (moving beyond near-term outcomes) • Why? For what impact? (connect to strategic objectives) • Does this move us closer to our future vision—or is it just activity? How do you challenge initiatives to ensure they align with your long-term strategy?

When ROI is used to compare strategic initiatives, strategy disappears. Some firms unintentionally kill their strategy by evaluating every initiative with the same metric—usually ROI. When ROI becomes the universal yardstick, strategy collapses into short-term financial sorting or into expensive failures based on hockey-stick projections. This is especially dangerous if CEOs are remunerated on the basis of EBIT targets or short-term stock options. As a board member and strategist, I recommend a different approach: assess initiatives along the Three Horizons. Three Horizon thinking is strategic because it forces leaders to do what strategy fundamentally requires: Allocate resources across different time horizons under uncertainty to optimize the current business and build the business of tomorrow. In other words: perform and transform. Horizon 1: Strengthen the core business These initiatives keep the company competitive today. Yes—ROI is appropriate here. Efficiency, margin, and cash flow matter. Horizon 2: Grow emerging businesses These initiatives build the next engines of growth. ROI is dangerous here because too many assumptions are required. The right question is: Does this strategic initiative meaningfully grow our emerging business? Horizon 3: Create options for the future These are investment into resources and capabilities that lead to potentially disproportionate competitive advantages. Early ROI calculations are meaningless. Instead ask: Does this strategic initiative create options we may need later? A real strategy allocates resources across all three horizons. In my experience, only Horizon 1 initiatives should be assessed by ROI. Horizons 2 and 3 require strategic judgment, not spreadsheet logic. Please repost if you agree. Comment if you disagree. Follow if you like more reframing. #strategy #leadership #transformation #VRIO #ROI #investments     Source of the Three Horizon model: Baghai, M., Coley, S., & White, D. (1999). The alchemy of growth: Practical insights for building the enduring enterprise. Perseus Publishing.

Many strategic initiatives don't fit into one timeline, and understanding their nature changes how you monitor them. Here’s a simple framework: ☑ AFE (After Finalisation Effects)  ↳ Initiatives where the realisation period starts after the project is completed. Example: Installing a new CRM system.   Only after launch can customer feedback and adoption be adequately measured. ☑ DPE (During Progress Effects) ↳ Initiatives where realisation overlaps with the project timeline, but with a lag. Example: Revamping a retail outlet.   As the first outlets are updated, customer reactions inform adjustments, even while other locations are still under construction. Key Takeaways: - AFE initiatives need patience: realisation only begins after go-live. - DPE initiatives require active monitoring during project progress. - Both types have a realisation time lag, a delay between output and outcome. - Monitoring lead and lag KPIS properly is essential for both. Understanding this distinction improves project tracking, risk management, and success rates. Reflection:   Which of your current initiatives are AFE vs DPE—and are you monitoring them accordingly? Ps if you like content like this, please follow me

If we're going to be effective with the execution of our organization's strategy it's going to hinge on the skills and capabilities of the leaders and managers we entrust with accomplishing it. The difference between a good strategy and its successful implementation lies in the hands of those who consciously lead others, recognize what's happening, and don't see giving up as an option. Here is what that takes: Articulation of Vision. Effective leaders possess a clear vision of desired outcomes and communicate it compellingly, ensuring everyone understands their goals and how to achieve them. Transparent Communication. Regular, open communication is essential. Managers who keep teams informed about progress, changes, and challenges foster a culture of trust and engagement, listening to feedback and responding to concerns. Goal Alignment. Effective managers ensure individual goals align with key initiatives at every level, breaking down the strategy into actionable plans for each department, team, and individual. Resource Allocation. Successful leaders allocate and manage resources—time, budget, and talent—efficiently, investing where needed to support critical aspects of the strategy. Clear Expectations. Winning at strategy execution requires clear expectations and performance standards, defining actions, metrics, and milestones to guide teams. Accountability. Leaders inspire accountability by supporting their teams, reviewing performance, removing obstacles, and helping them get unstuck when needed. Agility. Strategies require adjustment in response to internal and external changes. Leaders who pivot quickly ensure their organization remains on track despite unforeseen challenges. Problem-Solving Skills. Effective managers anticipate obstacles and develop contingency plans, addressing issues promptly to minimize disruptions. Regular feedback loops help leaders assess progress and make necessary adjustments. Empowerment and Collaboration. Effective leaders empower their teams by delegating authority and responsibility, this builds trust, ownership, and innovation, while enhancing cross-functional collaboration. Continuous Learning. Investing in training and development enhances your team's skills and capabilities, equipping them to execute at high levels daily. We recognize that all of this represents a significant amount of work. However, integrating these attributes into a dynamic process can make them disciplined habits that can lead to the results you need. What are you currently doing to enhance your people's understanding of strategy and its execution? #CEOs #Leadership #Strategyexecution #Attribute

87% of strategic initiatives fail. Not because of bad strategy. Because of Steve. Steve is your middle manager who doesn't believe in it. Watched this kill a $110M company's digital transformation. CEO announced shift. Board approved $15M. Consultants hired. 18 months later: $12M spent. Zero progress. CEO: "Everyone said they were on board." They lied. Well, nodded. Attended meetings. Said the right things. But Steve told his team in the hallway: "This digital thing will blow over. Just wait it out. We've been doing fine for 20 years." Steve managed 40 people. Those 40 managed 200 frontline employees. Steve's skepticism infected 240 people. That's 60% of the company working around the transformation while pretending to support it. The CEO never knew. Steve was perfect in meetings: → Took notes → Asked "good" questions → Committed to deadlines → Did nothing What actually kills transformation: → 10% actively resistant (you see them) → 20% genuinely supportive (you see them) → 70% watching middle managers for cues (you miss this) If your middle managers aren't bought in, your 70% goes nowhere. The fix: CEO met individually with every middle manager. Asked one question: "What do you really think about this?" 4 hours of brutal honesty later: → Addressed 8 legitimate concerns → Made 3 of them transformation co-leads → Gave the 70% permission to engage Transformation completed in 9 months. You don't have a strategy problem. You have a middle manager enrollmen

I watched our biggest initiative fail because of one critical mistake. We confused meetings with actual decision-making. More meetings feel like progress, but they rarely solve unclear ownership. When cross-functional projects start slipping, most leadership teams respond the same way: they schedule more alignment meetings. It feels productive. More discussion. More updates. More coordination. But the real problem usually isn’t communication. It’s unclear decision authority. When ownership isn’t designed clearly, meetings become a substitute for decisions. People talk more, but clarity doesn’t improve. Teams step on each other’s work. Deadlines slide. Every decision becomes a negotiation. The issue isn’t that people don’t talk enough. It’s that the system hasn’t defined who actually decides. When authority is distributed but accountability isn't, you get discussion instead of decisions. Strong leaders don’t solve this with more effort. They solve it with better structure. They design decision rights, not discussion forums. If cross-functional projects keep turning into long discussions instead of decisions, these 7 structures will help. 1️⃣ Map Decision Rights Before Projects Start Define who decides, who gives input, who gets informed. Test it before you start. 2️⃣ Distinguish "Consulted" from "Informed" Consulted = can change the decision. Informed = gets told the outcome. 3️⃣ Use the Commitment Test Ask: "What will you do differently?" Vague answers = you had a meeting, not alignment. 4️⃣ Institute the 48-Hour Decision Rule Cross-functional issues must be resolved or escalated within 48 hours. No exceptions. 5️⃣ Design Clear Escalation Triggers Define exactly when conflicts move up. Remove judgment calls. 6️⃣ Create the Autonomy Alignment Matrix Map decisions by impact vs. expertise. High expertise + low impact = full autonomy. 7️⃣ Set Response Time Standards Define response windows by decision type. Strategic: 5 days. Operational: 24 hours. Strong leadership reduces friction through structure, not effort. Design clarity into decision rights and authority. Alignment becomes automatic because teams know what they own, what they influence, and when to escalate. 💾 Save this for the next time your cross-functional projects turn into endless alignment meetings. ➕ Follow Rene Madden, ACC for systems-focused leadership strategies. Which of these decision structures would have the biggest impact in your organization?

Quick test for CFOs: If I asked for the ROI on your strategic initiatives, could you answer in under 60 seconds? One CFO couldn't. He had 9 of them. Only 2 created value. The other 7 cost $940K a year. Here's what we found: 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #1: 𝗡𝗲𝘄 𝗕𝗜 𝘁𝗼𝗼𝗹 $120K setup + $60K/year. 6 months, 3 people. Built 18 dashboards. CEO looks at 2. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #2: 𝗦𝗞𝗨 𝗽𝗿𝗼𝗳𝗶𝘁𝗮𝗯𝗶𝗹𝗶𝘁𝘆 𝗺𝗼𝗱𝗲𝗹 ✅ 80 hours. Killed 40 losing SKUs. Freed $1.2M in inventory. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #3: 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗟𝗧𝗩 𝗮𝗻𝗮𝗹𝘆𝘀𝗶𝘀 ✅ 60 hours. Repriced 3 segments. Margin up $400K/year. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #4: 𝗦𝗮𝗹𝗲𝘀𝗳𝗼𝗿𝗰𝗲 𝗶𝗻𝘁𝗲𝗴𝗿𝗮𝘁𝗶𝗼𝗻 $80K + 4 months. Sales still uses Excel. Integration unused. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #5: 𝗘𝗥𝗣 𝘂𝗽𝗴𝗿𝗮𝗱𝗲 $340K + 9 months. Same processes, shinier interface. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #6: 𝗥𝗼𝗹𝗹𝗶𝗻𝗴 𝗳𝗼𝗿𝗲𝗰𝗮𝘀𝘁 𝗿𝗲𝗯𝘂𝗶𝗹𝗱 3 months, 2 analysts. Too complex. Team reverted in 6 weeks. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #7: 𝗦𝗰𝗲𝗻𝗮𝗿𝗶𝗼 𝗽𝗹𝗮𝗻𝗻𝗶𝗻𝗴 100 hours. Built 12 scenarios. Exec team used 3. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #8: 𝗕𝗼𝗮𝗿𝗱 𝗿𝗲𝗽𝗼𝗿𝘁𝗶𝗻𝗴 𝗿𝗲𝗱𝗲𝘀𝗶𝗴𝗻 60 hours/quarter. Board asked for old format back. 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲 #9: 𝗖𝗼𝘀𝘁 𝗮𝗹𝗹𝗼𝗰𝗮𝘁𝗶𝗼𝗻 𝗺𝗼𝗱𝗲𝗹 120 hours building. Department heads ignore it. 𝗧𝗼𝘁𝗮𝗹 𝗰𝗼𝘀𝘁 𝗼𝗳 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲𝘀 𝟭, 𝟰, 𝟱, 𝟲, 𝟳, 𝟴, 𝟵: Labor: ~$780K/year Tools: ~$160K/year Total: $940K/year EBITDA impact: $0. 𝗘𝗕𝗜𝗧𝗗𝗔 𝗶𝗺𝗽𝗮𝗰𝘁 𝗼𝗳 𝗜𝗻𝗶𝘁𝗶𝗮𝘁𝗶𝘃𝗲𝘀 𝟮 & 𝟯: $𝟭.𝟲𝗠/𝘆𝗲𝗮𝗿. The CFO's reaction: "We've been calling everything 'strategic' because it sounds important." 𝗧𝗵𝗲 𝗹𝗲𝘀𝘀𝗼𝗻: Most finance teams are drowning in "strategic work" that isn't strategic. It's just complex. Real strategic work has 3 characteristics: Clear link to EBITDA, cash, or exit value Measurable outcome in <90 days Drives an actual business decision If it doesn't have all 3, it's cosplay. 𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝘄𝗲 𝗱𝗶𝗱: Killed Initiatives 1, 4, 5, 6, 7, 8, 9. Freed up 200 hours/month. Redeployed the team to: → Working capital optimization ($800K freed) → Pricing analysis ($1.1M margin leakage) → Vendor spend review ($420K saved) 𝗧𝗼𝘁𝗮𝗹 𝘃𝗮𝗹𝘂𝗲 𝘂𝗻𝗹𝗼𝗰𝗸𝗲𝗱: $𝟮.𝟯𝗠 𝗶𝗻 𝗬𝗲𝗮𝗿 𝟭. 𝗧𝗵𝗲 𝗻𝗲𝘄 𝗿𝘂𝗹𝗲: Before finance starts any "strategic project," answer: → What EBITDA/cash/exit metric improves? → By how much? → In what timeframe? → What decision does this enable? If you can't answer all 4, don't start. If your finance team is working on strategy but you're not seeing EBITDA impact, let's audit what they're actually working on. I'll show you: → What's truly strategic (vs. theater) → How much capacity you're burning on low-ROI work → What your team could be working on instead 𝗗𝗠 𝗺𝗲.

I recently reviewed a strategic plan that had a familiar pattern. 5 Pillars. 4 Goals per pillar. 6 Initiatives per goal. The math? 120 'priority' initiatives. That's on top of everything you do each day. Here's the thing: we're high achievers. We don't want to say no to a good idea, especially when a Board member or a donor is behind it. But when everything is a priority, nothing is. This is how "Strategic Drift" happens. You aren't struggling because of a lack of effort. You're struggling because your leadership team's capacity is being strained by the sheer volume of motion relative to progress. Strategic plans don't usually just stop. They evaporate into the daily grind. They stall under the weight of 120 competing "must-dos." The fix? Move from a Planning Mindset to an Operating Mindset. At MoonshotOS, we help schools build a formal School Operating System. It's the bridge between your high-level strategy and your Tuesday morning reality. Three shifts: • Define Your Critical Annual Priorities: I facilitate the conversations that help leadership teams stop listing and start deciding. We take that list of 120 and distill it down to the vital few that will actually move the needle this year. • The 90-Day Rule: Once you have your annual focus, you stop looking at the 5-year horizon and start looking at the next 90 days. You might select 5, 6, or 8 projects to move simultaneously, but the deadline remains the same. Shorter horizons create the urgency needed to actually finish what you start. • Change the Meeting: If your meetings are just people reporting on how busy they are, you aren't leading, you're spectating. Use that time to unblock the work and ensure those 90-day goals stay on track. You don't necessarily need a new plan. You need a better system to run the one you have. Are you managing 120 initiatives or a focused set of 90 day goals?

A Key 🔑 to Unlocking 🔓Business Transformation Success: Strategic Program Management Today, I’m exploring the critical role of strategic program management in driving business transformation. With over 20 years of experience managing complex programs across healthcare, insurance, government, and aerospace and defense, I've experienced firsthand the impact of effective program management on business & agency success. Business transformations are complex journeys that require a clear roadmap to guide them. Strategic program management provides that roadmap, coordinating and aligning multiple projects, resources, and stakeholders toward a common goal – the transformation objectives. Applying a structured program management framework, organizations can ensure that every project & initiative contributes to the overall #transformation goals. One of the biggest challenges in business transformations is navigating the surprises and stakeholder resistance that arise. Strategic program management helps address these challenges head-on by maintaining alignment, proactively managing risks, facilitating stakeholder communication, and optimizing resource allocation. 🔑 key to success: A key aspect of strategic program management is ensuring a smooth transition from program to operations. This involves establishing operational ownership, providing training and support, monitoring and optimizing performance, and embedding change management. By doing so, organizations can ensure that the transformation delivers long-term value & sustainable success. As someone who's built successful & profitable consulting practices, led complex programs, served as a CIO, and VP of Professional Services, I can attest to the importance of investing in strategic program management. It's not just about getting through the transformation – it's about setting the business up for #innovation & long-term growth. Prioritizing strategic program management enables organizations can unlock the full potential of their business transformations & achieve lasting success. Some key takeaways from my experience include: 🔘 Having a comprehensive risk register to proactively identify, mitigate & manage risks 🔘 Building strong relationships with executive stakeholders through direct engagement & regular reporting 🔘 Cross-training primary & secondary resources to minimize disruption due to personnel changes 🔘 Focusing on post-implementation phase to ensure smooth transition & long-term value delivery Applying these principles & investing in strategic program management, I’m certain that organizations can navigate the complexities of business transformation & achieve sustainable #success. REACH OUT to me to discuss how we can collaborate & resolve your challenges - Don Gleason

How do you decide when to double down on an initiative or when to walk away? This kind of strategic decision making is one of the top skills innovators must master. Here's how I make the decision without letting my pride take over: 1. Data-Driven Decisions 📊 I insist that every project measure what I call Pivot Indicators. These are pre-defined metrics that answer two important questions: "When will we know if it's not working?" and "How will we know?" By establishing these indicators upfront, we remove ambiguity from the evaluation process. Whether it's a certain threshold of user engagement, a predefined ROI, or customer satisfaction scores, these indicators act as the guardians of our resources, ensuring that we stay agile, respond promptly to feedback, and invest in avenues that truly resonate with our overarching goals. 2. The Passion Parameter ❤️ Numbers are vital, but they're not everything. The intangible yet palpable energy of passion is often the difference between projects that fizzle out and those that thrive. If you had to make the decision today to start this idea from scratch, would you do it? Are you still as excited about the opportunity as you were when everything kicked off? If your team exudes excitement and genuine belief in the project, this collective energy can transform challenges into opportunities. 3. Opportunity Costs and the Big Picture ⚖️ Every resource committed to one initiative means potential neglect for another. It's essential to ask: What could these resources achieve elsewhere? I actually sit down and make a list of where I would invest the resources if I had more time and effort. Then, I'm not deciding whether I failed at something or didn't, I'm just deciding between option A or B for my time and resources. Our resources—whether time, talent, or capital—are finite, and successful innovators understand that we have to continuously reassess to make sure that we don't get stuck. How do you decide whether to re-invest or walk away? #innovation #management #strategy