Breakthrough Coaching is the executive coaching practice founded by Dan Sakaki, a certified executive coach and seasoned facilitator with over 25 years of experience developing leadership capacity across the non-profit and business sectors. It guides individuals, leaders and groups toward meaningful, measurable growth.
“The art of leadership is saying no, not saying yes. It is very easy to say yes.”
Tony Blair
Strategic Thinking & Vision Overview
This two-day workshop equips leaders to think beyond day-to-day operations: reading their competitive environment, anticipating multiple futures and translating insight into a compelling vision that wins genuine buy-in. Participants apply proven strategy frameworks to real organizational challenges and learn from cases including Netflix versus Blockbuster and Microsoft under Satya Nadella.
The workshop finishes with a board-pitch capstone simulation and a personal 30/60/90-day action plan. A follow-up coaching session with Q&A supports key messages and adoption.
What we cover
Day 1, Module 1: What Is Strategic Thinking? Strategic versus operational thinking and the trap of defaulting to the mode that earned your last promotion. The six habits of mind of strategic thinkers. Exercise: Strategic or Operational? Leave able to distinguish strategic from operational thinking and know when each is required, reframe operational problems as strategic questions, and self-assess against the six habits.
Day 1, Module 2: Reading the Environment PESTLE scanning with the 'so what?' discipline. Porter's Five Forces. From SWOT to TOWS, pairing quadrants to turn analysis into moves (cases: Netflix vs Blockbuster, LEGO). Exercise: an environmental scan of your own industry. Leave able to apply PESTLE and Five Forces to a competitive environment, turn signals into decision-ready implications, and use TOWS pairing to generate strategic moves rather than static lists.
Day 1, Module 3: Thinking in Systems & Time The Iceberg Model. Second-order thinking and the Cobra Effect. Scenario planning: the Shell story and the 2x2 method. Exercise: consequence mapping with a pre-mortem, and four futures for your industry. Leave able to diagnose problems at the level of structure and mental models, trace second- and third-order consequences before committing, and build 2x2 scenarios that surface moves robust across several futures.
Day 2, Module 4: Crafting a Compelling Vision Vision versus mission versus values versus strategy. The anatomy of a vision people will follow: vivid, ambitious, purpose-anchored, shared, choice-forcing, checkable. Cases: Kennedy's moonshot, Nadella, SpaceX, IKEA. Exercise: draft your vision, then paired scoring. Leave able to distinguish vision, mission, values and strategy, craft a vision statement that meets all six criteria, and strengthen drafts through structured peer feedback.
Day 2, Module 5: Communicating the Vision Why vision communication fails. Storytelling structure: Context, Stakes, Destination, Ask. Kotter's 8 Steps. Exercise: the 90-second vision pitch in trios with SBI feedback. Leave able to avoid the four classic vision-communication failures, deliver a 90-second pitch in a story others can retell, and apply Kotter's 8 Steps to plan a change-communication campaign.
Day 2, Module 6: From Vision to Strategy to Action Playing to Win: five connected choices. The discipline of saying no. Cascading vision to Monday morning through priorities, team OKRs and individual goals. Leave able to connect vision to a coherent strategy, name what the organization must stop doing to fund it, and cascade it into team objectives and individual weekly work.
Capstone: The Northgate Foods Challenge An executive-team simulation. Build a five-year vision and strategy for a legacy packaged-foods company facing core decline, in 75 minutes. Deliver a three-minute board pitch, take board Q&A, peer scoring and full-group debrief. Integrate every framework in the course under realistic time pressure, defend strategic choices before a skeptical board, and reflect on how the team made decisions.
Close: Sustaining the Practice Strategic thinking as a weekly practice: strategy hour, outside-industry scanning, pre-mortems, quarterly radar reviews. A personal 30/60/90-day plan with an accountability partner. Commit to specific, dated practices that sustain strategic thinking.
Key takeaways
Strategic thinking is a distinct mode: synthesis about where to go, not analysis of how to optimize
Environmental reading only matters when every force ends in a specific, decision-ready 'so what'
Leverage lives below events, in structures and mental models; second-order thinking turns surprise into preparation
A vision works when it is vivid, ambitious, purpose-anchored, shared, choice-forcing and checkable, and it changes nothing until it is over-communicated
Strategy is five reinforcing choices, and it becomes real only when something is stopped
Cascade two ways: every person can trace their Monday to the vision; every level can send truth back up
Every session is customized to your industry and environment. The final agenda is confirmed with your facilitator before delivery.
For organizations that want their leaders to set direction, not just deliver against it: read the environment, craft a vision people follow and turn it into a plan.
Leaders stepping up from operational roles into strategic ones
Executive and senior management teams who want a shared strategy language
Two days of instructor-led instruction
Frameworks reference: PESTLE, Five Forces, TOWS, Iceberg Model, scenario planning, Playing to Win
The Northgate Foods capstone simulation
A 30/60/90-day plan and a follow-up coaching session with Q&A
Live online: instructor-led, fully interactive, no travel
In-person: at your offices or a venue of your choice
Designed for cohorts of 6 or more
Includes the Northgate Foods board-pitch capstone simulation
Pricing depends on delivery mode, group size and how much customization you want. Tell us the shape and we will quote it.
