When leaders announce a new initiative — whether it’s a digital transformation, a merger or a new market entry — the excitement is often accompanied by apprehension and uncertainty about its execution. Too many big bets falter not because the idea was poor but because the right questions were never asked at the start, leaving teams unprepared for inevitable challenges.
As Jim Collins’ Hedgehog Concept reminds us, enduring success comes from clarity and focus. Similarly, my music-inspired leadership frameworks demonstrate that, like a jazz ensemble, initiatives succeed when the fundamentals — vision, rhythm and alignment — are solid and continuously reinforced.
Here are seven questions leaders should ask themselves and their teams before the first dollar is spent or the first milestone is set.
1. Does this initiative align with our “one big thing”?
Every organization has a core identity — what it is passionate about, what it can excel at, and what drives its long-term economic engine. Before committing resources, leaders should ask: Does this initiative reinforce our Hedgehog Concept, or does it distract from it and consume valuable capacity?
Apple’s turnaround under Steve Jobs worked precisely because he cut distractions and doubled down on Apple’s unique intersection of design, technology and user experience. Leaders should apply the same discipline: initiatives that dilute focus, no matter how attractive or seemingly urgent, are costly detours that drain momentum and clarity.
2. Have we defined the real problem we’re solving?
Rushing into execution without defining the real issue is like improvising without knowing the key or the rhythm. Problem-solving methods such as the “5 Whys” or the Phoenix Checklist help teams dig past surface symptoms to the deeper root cause that truly matters.
Ask: What’s the actual barrier this initiative addresses? If your workforce is disengaged, is the answer really a new digital tool — or is it a cultural problem of trust, leadership alignment and authentic connection? Precision in framing the challenge prevents wasted effort, lost credibility and costly investment in the wrong solution.
3. Do we have the right rhythm and culture to support it?
As I write about in my book, Culture Is the Bass, culture is the underlying rhythm of the organization; if it’s off, no strategy will sound right or sustainable. Leaders should ask: Will our current culture accelerate, support or quietly sabotage this initiative once the pressure rises?
If collaboration, psychological safety or accountability are lacking, those gaps must be addressed first. Just as a jazz ensemble relies on trust, listening and shared timing, initiatives require a culture that promotes open feedback, continuous learning, adaptability and the confidence that every voice will be heard when challenges inevitably surface.
4. Have we stress-tested our execution plan?
Ambition without execution discipline is a recipe for burnout and disillusionment. In A Symphony of Choices, I emphasize portfolio thinking: treating every initiative as part of a broader score where timing, sequencing, dependencies and resources must harmonize seamlessly.
Leaders should ask: Have we prioritized this initiative over all others, and do we truly have the capacity, funding and resilience to deliver it? Tools like decision matrices or McKinsey’s 7-step problem-solving framework help leaders allocate scarce resources to initiatives with the highest impact, ensuring execution discipline supports strategic intent instead of overwhelming people or diluting focus across too many competing priorities.
5. What does success look like — and how will we measure it?
Vague aspirations such as “improve efficiency” or “become more innovative” doom initiatives to drift aimlessly. Leaders must define concrete outcomes, such as reducing cycle time by 20%, increasing customer retention by 10% or increasing profit per customer visit (as Walgreens used to, with a significant impact over decades of growth).
Ask: What are the key metrics, and how will we track and communicate them consistently across the organization? Just as musicians rely on sheet music, timing, or tempo, teams need clear measures, agreed-upon baselines and transparent dashboards to stay in sync, self-correct quickly and know precisely when they are offbeat.
6. How will we engage both hearts and minds?
Data and strategy win agreement, but emotion drives commitment and discretionary effort. Research indicates that burnout and disengagement often result from a lack of genuine emotional connection within teams and organizations. Leaders must ask: Have we crafted a compelling story that makes people care deeply enough to sustain momentum?
In Workplace Jazz, I demonstrate how music inspires connection and trust — lessons leaders can apply through storytelling, symbolic actions, rituals and visible empathy. Without emotional resonance, even the best strategy feels transactional, fails to inspire loyalty and risks collapsing under stress when obstacles arise or energy begins to fade.
7. What will we stop doing to make room for this?
Perhaps the most challenging question of all. New initiatives demand time, talent, energy, and focus — resources that are already in short supply and often stretched across competing commitments. Leaders should ask: What projects, habits or priorities will we sunset, pause or permanently retire so that this initiative can truly succeed?
As Collins notes, discipline is as much about deciding what not to do as it is about what to do. The courage to say “no” consistently separates leaders who achieve breakthrough results from those who perpetually juggle too many half-finished initiatives, dissipating momentum, credibility and long-term organizational confidence.
Leaders are conductors, not soloists
Launching a major initiative is less about making grand announcements and more about orchestrating clarity, rhythm and discipline across the entire organization. The best leaders behave like conductors: ensuring each player knows their part, the tempo is steady and the music aligns seamlessly with the score.
Before you press “go” on your next significant initiative, sit with these seven questions. They are not hurdles to slow you down, but essential tuning exercises that ensure when your team plays together, it creates purposeful music — not distracting noise — and delivers results that genuinely resonate with stakeholders.
Opinions expressed by SmartBrief contributors are their own.
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