Proactive Planning Techniques

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

The selective focus on ESG Too often, the ESG discourse narrows to carbon, diversity, and board composition. While important, this selective focus delegitimizes ESG and impoverishes corporate action. ESG encompasses a far broader spectrum of strategic priorities, such as: • Environmental: Biodiversity, natural resources, water cycles, natural ecosystems, circular economy and land use; • Social: Human rights, Health & safety, stakeholder engagement, wellbeing, labor practices, supply chain responsibility, inclusion and community impact; • Governance: Risk management, cybersecurity, executive compensation, anti-corruption, transparency, internal controls and business ethics. When organizations cherry-pick convenient metrics, they miss the holistic integration that drives real value. Research shows that companies pursuing comprehensive ESG strategies outperform those with isolated initiatives. The other dimensions aren't secondary. They're equally, if not more, critical for long-term resilience and authentic sustainability. Let's elevate the conversation. ESG strategy demands depth, not shortcuts. #ESG #Sustainability #CorporateStrategy #ESGReporting #SustainabilityStrategy

Most sales leaders run their calendars backwards. They review calls after they happen. They review pipelines after deals stall. They review activity after the week is over. Then they wonder why they're always playing catch-up. I want to challenge every VP, Director, and Manager reading this: Open your calendar right now. Find every meeting with "review" in the title. Now flip it. Call review → Call prep Pipeline review → Pipeline planning Activity review → Activity planning Forecast review → Forecast building And move them earlier in the week. This is what I call becoming a Proactive Leader. Most one-on-ones are backward-looking. "What happened last week?" "How did that deal go?" "Why didn't you hit activity?" That's all after the fact. You can't change what already happened. Proactive one-on-ones are forward-looking. "What's the plan this week?" "What do you need to win that deal?" "How are we going to hit activity?" Same amount of time. Completely different results. Think about it: You spend 30 minutes reviewing a call that already happened. What if you spent those same 30 minutes prepping for the call before it happened? Role playing. Practicing objections. Planning the flow. Which one actually moves the needle? Here's my challenge: Over the next 90 days, flip your calendar from reactive to proactive. Every review meeting becomes a prep meeting. Every backward-looking conversation becomes forward-looking. Watch what happens to your team's results. Proactive leaders don't just inspect what happened. They architect what's going to happen. That's the difference.

Every task that comes to me is urgent and important. Sound familiar? This is a challenge many of us face daily. Early in my career, prioritization was relatively straightforward—my manager told me what to focus on. But as I grew, the game changed. Suddenly, I was managing a flood of requests, far more than I could handle, and the signals from others weren’t helpful. Everything was “important.” Everything was “urgent.” Often, it was both. To handle this effectively, I realized I needed to develop an internal prioritization compass. It wasn’t easy, but it was transformative. Here are 6 strategies to help you build your own: 1/ Be crystal clear on key goals Start by understanding your organization’s goals—at the company, department, and team levels. Attend organizational forums, departmental reviews, or leadership updates to stay informed. When in doubt, use your 1:1s with leaders to ask: What does success look like? 2/ Deeply understand KPIs Metrics guide decision-making, but not all metrics are equally valuable. Take the time to understand your team's or function's key performance indicators (KPIs). Know what they measure, what they mean, and how to assess their impact. 3/ Be assertive to protect priorities Not every task deserves your attention. Practice saying “no” or deferring requests that don’t align with key goals or metrics. Assertiveness is not about being inflexible—it’s about protecting your capacity to focus on what truly matters. 4/ Set and reset expectations Priorities change, and that’s okay. What’s not okay is working on misaligned tasks. Keep open communication with your manager and stakeholders about evolving priorities. When new demands arise, clarify and reset expectations. 5/ Use 1:1s to align with your manager Leverage your 1:1s as a strategic tool. Share your current priorities, validate them against your manager’s expectations, and discuss any conflicts or challenges. 6/ Clarify the escalation process When priorities conflict, don’t let disagreements linger. If you can’t agree quickly, escalate the issue to your manager. This avoids unnecessary churn, ensures trust remains intact, and keeps momentum focused on results. PS: You won’t always get it right—and that’s okay. Treat each misstep as an opportunity to refine your compass. What’s one tip you’ve used to prioritize when everything feels urgent? --- Follow me, tap the (🔔) Omar Halabieh for daily Leadership and Career posts.

From Siloed Projections to System-Wide Planning: How We Built Singapore’s Healthcare Capacity Framework 3 years ago, our healthcare demand projections were done in silos. Today, we have a coherent, system-wide framework that links demand to infrastructure, manpower, and budget planning. Honoured by the recognition on the work done by the team. Here’s the transformation journey. The Challenge We Faced Demand for each care setting is projected independently, using different assumptions and methodologies. 2023: Building the Foundation Introduced more granular inputs: added parameters e.g. functional impairment levels and family support in long-term care projections. Linked patient flows: Connected across settings (e.g. ED visits to acute inpatient to community hospital). 2024: Achieving System Coherence The coordination challenge: Working across 8+ divisions (IPP, HSD, PCC, APO, MP&S, HF) while handling new policy simulations & evolving capacity decisions. The solution: Set up Capacity Planning Committee (CPC) as single decision platform, replacing piecemeal EXCO discussions. The breakthrough: Obtained approval for our projections alignment framework: • Single baseline model across all projections • Common parameters where models intersect • Systematic accounting for care transformation impacts Real impact: Secured approval for new hospital beds through white space activation and new hospital sites. 2025: Advanced System Modelling Healthier SG simulation: Collaborated with Duke-NUS to quantify HSG’s long-term impact on healthcare demand and costs - answering our persistent questions. Disease-based projections: Piloted new method for mental health services, endorsed and used for service planning Tight deadline delivery: Completed baseline and care transformation projections across all settings that should have taken a few years to complete within one year. The Framework That Changed Everything Our Long-Term Capacity Planning Framework now seamlessly connects: • Demand drivers (population aging, functional impairment) • Care settings (from acute to community to home-based care) • Resource planning (manpower, infrastructure, budget) Policy interventions like HSG, right-siting efforts, and palliative care strategies are incorporated. Key Lessons Learned 1. Coordination is as important as methodology - The CPC structure solved more problems than technical improvements alone 2. Resilience matters - When our HSG model wasn’t endorsed initially, we went back to fundamentals and rebuilt stakeholder confidence 3. Granular parameters drive better insights - Moving from broad assumptions to specific factors like family support levels improved accuracy The result? A coherent planning system that helps Singapore prepare for demographic transitions while optimising resource allocation across the entire healthcare continuum. What challenges are you facing in system-wide planning and coordination across multiple stakeholders?

Something remarkable happened when we started bringing Customer Success leaders into our sales conversations. The traditional sales process transformed into a strategic partnership discussion that benefited everyone involved. After implementing this approach across hundreds of deals, we discovered benefits that went far beyond our initial expectations. Sales teams gained a deeper understanding of post-implementation challenges, which helped them qualify opportunities more effectively. Instead of focusing solely on closing deals, they began asking questions about operational readiness, internal champions, and resource allocation. Prospects received authentic insights into what successful implementation truly requires. Our CS leaders shared real examples of customers who thrived and openly discussed common obstacles they might face. This transparency built trust and helped prospects make informed decisions. Better aligned customer expectations from day one. When CS leaders joined these conversations, they highlighted potential roadblocks and success metrics based on similar customer profiles. This practical guidance helped prospects understand the work required to achieve their desired outcomes. This early involvement proved invaluable for our CS team. They gained visibility into the customer's vision before contracts were signed, allowing them to proactively plan resources and create tailored onboarding strategies. A surprising result was the reduction in "rescue" situations during implementation. We eliminated many issues that typically surfaced months into the relationship by addressing potential challenges during sales discussions. The data supported our approach. Deals that included CS leaders showed 40% higher implementation success rates and 25% faster time-to-value. More importantly, these customers renewed at significantly higher rates. For those considering this approach, start small. Choose strategic opportunities where CS insights could substantially impact the prospect's decision-making process. Document the outcomes and refine your strategy based on that feedback. Great customer relationships begin with the very first conversation.

Lessons in Strategic Growth: The Crucial Balance Between Expansion, Focus, and ROI in the Cannabis Industry In the dynamic world of the cannabis industry, the past 5 to 6 years have been a revelation, particularly in understanding strategic growth. Many companies, lured by the prospects of being first movers, embarked on rapid expansion and pivoting strategies, only to face challenges that offer key lessons for others in this sector. The Pitfalls of Premature Expansion A common narrative has been the insufficient ROI from rapid expansion. Companies have often spread their resources too thin, venturing into markets without adequate demand or underestimating the complexities involved. This led to a critical oversight: failing to achieve sustainable returns on their hefty investments. Diluted Efforts, Diminished Returns Expansion without strategic focus has resulted in diluted efforts and resources. This dispersion not only hampers the potential in each area of expansion but also overlooks the essence of long-term value creation. The consequences have been stark – decreased ROI, weakened brand identities, and eroded investor confidence. The Power of Maintaining Focus On the flip side, companies that maintained a strategic focus have reaped the benefits. Concentrating on core strengths and markets where they hold a competitive edge has resulted in optimised resource allocation and higher ROI. Such a focused approach has also contributed to building robust brand identities and sustainable growth patterns. Effective Use of Investor Funds A focused strategy ensures that investor funds are utilised effectively. This not only boosts investor confidence but also paves the way for more sustainable financial support. It's a stark reminder that disciplined growth, aligned with a company's strengths and market demand, is key to long-term success. Conclusion The challenges faced by the cannabis industry serve as a crucial lesson in strategic growth. Balancing the aspiration to expand with the need for focus and realistic ROI expectations is vital. As we move forward, it's clear that growth strategies need to be carefully planned, ensuring that every step towards expansion is grounded in market realities and aligned with the company's core competencies. #CannabisIndustry #StrategicGrowth #BusinessExpansion #ROI #MarketStrategy #BusinessLessons Picture ©Carl Haffner 2024

Mastering Strategic Focus: How Startups Avoid Spreading Themselves Too Thin 🎯 In the early stages, opportunity is everywhere. New features, new markets, new partnerships, new ideas. But growth is rarely limited by lack of opportunity. It is limited by lack of focus. Let’s explore how startups can build disciplined focus without slowing ambition. Why Strategic Focus Is a Competitive Advantage The most resilient startups are not those that do the most. They are the ones that do the right few things exceptionally well. 🌟 Define What Truly Moves the Needle Not every initiative deserves equal energy. Identify the 2–3 priorities that directly impact revenue, retention, or product strength. Tip: Align quarterly goals with one measurable business outcome. 🌟 Create Clear “No” Criteria Saying no becomes easier when you have predefined filters. Tip: Before committing to new ideas, ask whether it strengthens your core value proposition. 🌟 Protect Team Bandwidth Constant pivots drain teams and dilute execution quality. Tip: Review workload regularly and eliminate initiatives that are not delivering measurable returns. 🌟 Sequence Growth Intentionally Expansion works best when built on stable foundations. Tip: Strengthen one channel or product line before layering additional complexity. 🌟 Measure Focus, Not Just Activity High activity does not equal progress. Tip: Track impact metrics over effort metrics. Revenue growth, customer retention, and margin improvement tell a clearer story than task volume. 🌟 Communicate Strategic Priorities Clearly Teams perform better when they understand what matters most. Tip: Reinforce core objectives consistently in meetings and updates. Moving Forward Focus is not about shrinking ambition. It is about sharpening it. Startups that scale successfully are those that concentrate resources, energy, and decision-making around what truly drives value. What has helped you maintain strategic clarity while growing? Arise Ventures Avinash Vashistha Tholons Inc. Frank Pendle Shari Wenker #StartupGrowth #FounderJourney #StrategicFocus #Leadership

𝗖𝗹𝗶𝗲𝗻𝘁 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻: "When everything feels urgent, how do you prioritize?" 𝗠𝘆 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: I start by taking a step back to assess three key areas: • 𝗠𝗮𝗿𝗸𝗲𝘁𝗶𝗻𝗴: Are you generating enough leads to meet your revenue goals? • 𝗦𝗮𝗹𝗲𝘀: How is your conversion rate holding up? • 𝗖𝗮𝗽𝗮𝗰𝗶𝘁𝘆: Are you nearing your team's limit, and how many more clients can you realistically handle without compromising quality? Once I’ve pinpointed the most critical area, I tackle my urgent list with a strategic mindset: • What tasks can I delegate to free up time? • What processes can I automate to increase efficiency? • How can I streamline workflows to make everything run smoother? By honing in on the key area, I make sure I’m working on what truly moves my business forward, steering clear of tasks that might seem urgent or promising but are really just distractions. For example, why focus on marketing if you’re already at capacity or struggling with sales conversions? Remember: Prioritization is about aligning your efforts with your business needs so you’re not just playing a game of whack-a-mole. Illustration Pejman Milani

Resource planning separates successful firms from those constantly scrambling to meet deadlines 📊 Most finance teams operate in reactive mode, putting out fires instead of preventing them. I've worked with dozens of clients who struggle with this exact problem. They're always stressed, always behind, and wondering why profitability suffers despite working harder than ever. ➡️ CAPACITY PLANNING FOUNDATION You know what I've learned after years of helping firms optimize their resources? It all starts with forecasting your hours correctly. See, when you can predict workload based on historical data and upcoming client needs, you avoid that feast or famine cycle that absolutely crushes profitability. Monthly recurring revenue clients need consistent attention too. Don't make the mistake I see so many firms make by forgetting about them during busy season. Client volume scaling requires a completely different approach. Growing your client base means different staffing patterns and retention strategies. Plan resources based on both current clients and realistic growth projections. ➡️ BUDGET VS ACTUALS Track your planned versus actual resource utilization religiously. Variance patterns tell you exactly where your assumptions are off. Sometimes it's scope creep eating up resources. Sometimes it's inefficient processes slowing everyone down. Sometimes it's just unrealistic estimates from the start. Your resource planning gets better when you learn from what actually happened versus what you expected. Create accountability across your team so everyone understands how their work impacts overall capacity. ➡️ TIME TRACKING Without accurate time data, resource planning becomes pure guesswork. Monitor your billable versus non-billable ratios to understand true capacity. That administrative time still consumes resources and needs planning. Track project profitability in real-time so you can course-correct before it's too late. Waiting until project completion to assess profitability costs money. Use time data to identify productivity bottlenecks. Maybe certain work takes longer than expected, or specific team members need additional training. ➡️ STANDARD OPERATING PROCEDURES Document your repeatable processes and workflows. This dramatically reduces training time for new team members. Consistent processes mean more predictable resource requirements. When everyone follows the same approach, you can actually forecast capacity accurately. ➡️ CLIENT SCOPE DEFINITION Clearly define project boundaries upfront. Scope creep destroys resource planning faster than anything else I've seen. Set realistic client expectations from the start and stick to them. When clients want additional work, have a system to price and resource it properly. === Resource planning isn't glamorous work, but it's what separates profitable firms from those working harder for less money. What's your biggest resource planning challenge?