Coach.Win

John Lund

Elevating Leading Business Coaches to help drive Impact for our clients. Driving AI Activation and Automation.

  1. JAN 31

    Mastering Strategy Execution: How AI, OKRs, and an "Embedded Coach" Can Define Your Wins

    1. Learn How to Define "What Winning Looks Like" (WWLL) Before hiring a coach, you must understand how to align your team behind a unified vision. This video explains the concept of "WWLL"—ensuring every employee knows exactly what a good day, week, or year looks like. The speakers discuss why the traditional 5-year plan is becoming obsolete due to the pace of technology, and why focusing on a crystal-clear 3-year plan provides the agility modern businesses need. 2. Discover the Role of AI as a Strategic "Thought Partner" A modern strategic coach shouldn't just facilitate; they should leverage technology to sharpen your focus. The hosts demonstrate how to use AI during planning sessions—not to replace human leadership, but to generate tough questions and refine "squishy" goals into concrete, measurable objectives. This ensures you aren't just copy-pasting AI results, but using them to challenge your leadership team's thinking. 3. Understand the Value of an "Embedded Coach" This video introduces a shift from the traditional "drop-in" consultant to an "embedded coach" who integrates directly into your daily workflow (such as Microsoft Teams). By having a coach who sees your dashboards and chats daily, you get real-time course correction rather than waiting for quarterly reviews to discover you are off track. 4. Move From Vague Objectives to Actionable OKRs Many businesses set generic goals like "implement a new CRM" without defining the specific business impact. This discussion highlights the importance of Objectives and Key Results (OKRs), teaching you how to demand measurable metrics—such as "better accuracy on prospect lists"—so you know exactly when to celebrate a win. 5. Prevent Burnout by Validating Plans with Your Team Hiring a coach isn't just about setting ambitious goals; it’s about ensuring they are achievable. The speakers outline a critical validation process: drafting the plan, stepping away, and allowing the team to review it for capacity. This prevents setting your staff up for failure by ensuring no one is inadvertently assigned impossible workloads across multiple objectives.

    12 min
  2. 10/22/2025

    Do You Have a Super Facilitator? The Crucial Human Key to AI-Enhanced Annual Planning

    Are you trying to run your planning sessions in the infinite workday chaos, where employees face 117 emails and 153 messages daily? This fragmented environment is a huge barrier, but the solution isn't just AI—it's having the right expert guidance. We explore how leaders can transform their businesses into a frontier firm—human-led but agent-operated—by integrating intelligent AI agents (a "true force multiplier") with super facilitation. Learn why having a proven facilitator who understands how AI drives things is the key to running an "Annual Reset 2.0" that builds collective intelligence, creates a dynamic "living plan," and unlocks value you haven't seen before. -------------------------------------------------------------------------------- 5 Reasons an Owner of SMB Should Listen 1. Escape the "Infinite Workday" and Reclaim Focus: Employees are overwhelmed, facing an average of 117 emails and 153 Teams messages daily, creating chaos and fragmented progress. By listening, owners will understand how AI agents can handle routine, fragmented tasks, allowing their teams to offload the "grunt work" and focus on high-value work. 2. Ensure Your Strategy Becomes a Dynamic "Living Plan": Learn how the combination of AI and expert coaching can lead to the creation of a private AI strategy agent. This "living plan" doesn't just "sit on a shelf" but becomes actionable, capable of validating ideas, running "what-if scenarios," and even theoretically flagging when discussions go off strategy in meetings. 3. Drive Proven, Measurable Business Results: The shift to a frontier firm model is not just theory. Owners will learn about tangible results, such as Microsoft sales teams reporting 9.4% higher revenue per person and closing 20% more deals when utilizing AI tools. 4. Master the Human Element: The Need for Super Facilitation: While AI agents act as a "true force multiplier," expert guidance is crucial. Owners must determine if they have the right person running their strategy sessions—a "Super facilitator" who can skillfully weave together AI insights with diverse human perspectives, build trust, and generate real collective intelligence during planning sessions like "Annual Reset 2.0". 5. Transform Leadership into Effective "Agent Bosses": The expert coaching component is vital for helping leaders adapt, interpret AI's output, and lead these new human-agent teams effectively. By embracing this new approach, leaders are empowered to set clear direction for their AI partners, allowing the organization to focus on the vital 20% of work that drives 80% of the company's results.

    7 min
  3. 10/17/2025

    The Offsite Advantage: Crafting High-Impact Meetings with Coach.Win Episode

    Are your offsites productive, or are they disasters waiting to happen? Join Coach.Win founders Rob Simons and John Lund, who have facilitated thousands of meetings, as they reveal the critical anatomy of a great meeting room. Learn how optimizing space, technology, logistics, and comfort ensures high-energy, distraction-free planning sessions 1. Ensure Critical Planning Success by Eliminating Distractions: Leaders should insist on holding important quarterly or annual planning sessions offsite because even a great room on-site can lead to challenging distractions once participants step out of the meeting space. 2. Boost Team Vibe and Physical Engagement: Learn best practices for room layout, such as choosing a facility that is at least double (or even triple) the size of the group, and setting up U-shaped tables. This setup provides crucial space (like three feet behind chairs) that encourages team members to move around, utilize whiteboards, and post notes without disturbing neighbors, thus keeping the energy higher. 3. Prevent Meetings from Being Derailed by Technical and Environmental Flaws: Discover how subtle issues like nonstop noisy air conditioning (the "fog horn") or a lack of self-control over heat/AC can ruin comfort. Also, understand the importance of flat walls for sticking post-it notes and planning to bring your own power strips to avoid exorbitant venue charges and guarantee laptop power access. 4. Master Complex Logistics and Travel Planning: Avoid the red flag of trying to order food during the meeting; instead, learn to pre-order food, account for all dietary restrictions (gluten-free, vegan, etc.), and arrange meals in a separate room to mix things up. Additionally, leaders must account for potential construction or traffic (like a two-hour ride to the airport) to set realistic start and end times, preventing participants from scrambling and ruining the close of the meeting. 5. Seamlessly Integrate Remote Participants into Offsites: Prepare for the "gotcha" scenario where a last-minute remote attendee joins due to illness or travel issues. Leaders must know to bring necessary equipment, such as a conference microphone or a meeting owl, to pick up everyone’s voice, especially if recording or transcribing the session. Furthermore, if 25% or more of the team will be remote, the best practice is often to make the entire meeting remote to avoid mixing in-person and virtual facilitation challenges.

    16 min
  4. 02/27/2025

    Activating AI in Your Organization: Insights from Coach Rob and Coach John

    In this engaging podcast, Coach Rob from Coach dot Win and Coach John delve into the hot topic of AI activation within organizations. They discuss common misconceptions, the importance of strategic planning, and the role of leadership in successfully integrating AI. Key takeaways include: Misconceptions about AI: Many leaders mistakenly view AI as a quick fix, but it requires a well-thought-out implementation plan. 0:38Role of IT vs. Business Decision: AI integration is a business decision, not just an IT one. Governance and security are crucial, but the business strategy should drive AI adoption. 1:42Aligning AI with Company Vision: AI should support the company's mission and core values. Having a strategy coach can help ensure alignment and effective implementation. 2:37Steps to Activate AI: Start by aligning the leadership team, conduct department meetings to identify an AI committee, and focus on quick wins to build momentum. 4:07Overcoming Fear of AI: Educate employees on AI's potential to elevate their roles by automating tedious tasks, thus fostering a positive attitude towards AI adoption. 7:47Real-world Examples: The podcast shares practical examples of AI in training, field operations, and content development, highlighting the tangible benefits of AI integration. 9:49Tune in to learn how to effectively activate AI in your organization and gain a competitive edge. For more insights, reach out to Coach John at John at Coach dot Win or connect on LinkedIn under Coach dot Win. 14:02

    15 min
  5. 02/24/2025

    Embedded Coaching: Elevating Strategy and Execution

    Key Topics: Embedded Coaching Approach: Rob discusses his unique method of becoming an integral part of his clients' teams by using tools like Microsoft Teams to stay engaged and accessible. This approach enhances collaboration and accountability. 0:46Strategy and Planning: The conversation covers the importance of narrowing down strategic goals to focus on what truly moves the needle for the company. Rob emphasizes the transition from traditional rocks to OKRs (Objectives and Key Results) for better accountability and measurable outcomes. 3:14Leadership Challenges: Rob highlights common challenges faced by leadership teams, such as trying to do too much and not focusing on impactful tasks. He shares insights on how to overcome these challenges by aligning strategy and execution. 2:19Next Level Leaders: The importance of involving next-level leaders in strategy meetings to improve communication, alignment, and identify future leaders within the organization. Rob shares a success story of promoting a next-level leader to the executive team. 8:11Surveys for Organizational Pulse: Utilizing surveys to gather feedback from all levels of the organization, helping to identify blind spots and improve overall strategy and execution. 6:32Guest: Rob, an embedded coach from Coach.Win Host: John Description: In this episode, Rob from Coach dot Win shares his innovative approach to embedded coaching, focusing on strategy, planning, and execution. Learn how involving next-level leaders and using OKRs can transform your organization's performance. Discover the power of surveys in understanding the true pulse of your company and aligning your team for success.

    9 min

Ratings & Reviews

5
out of 5
4 Ratings

About

Elevating Leading Business Coaches to help drive Impact for our clients. Driving AI Activation and Automation.