Effective Coaching Questions In The “Sport” Of Business

Steve Schloss
6 min readMar 28, 2024
Photo by cottonbro studio

In light of the annual confluence of major sports activity, highlighted by March Madness (and the millions of busted brackets) and for me, the upcoming Masters, last week I shared thoughts on the connection between sport coaching and executive and team coaching in business.

Part II of this post focuses on a diverse range of coaching questions for individual and team clients, using the metaphor of sports. Clients who might be attracted to or engaged in a diverse range of sports and activities may find these questions more appealing in helping them visualize and reframe opportunities for growth and change.

This list could be much longer! So, if this speaks to you, feel free to plug in relevant examples to meet your client where they are. How do these work for you? What might you add or change? Love your thoughts.

For Individual Leaders

Setting Goals

  • Like a team or athlete strategizing for a championship, picture yourself as the coach of your own success story, plotting each move towards victory. How do you envision this journey unfolding?
  • Imagine your career aspirations as performance targets on the field. How can we break down these aspirations into tangible, actionable goals, just as athletes set their sights on specific milestones?
  • In sport, coaches set clear objectives for their teams. What’s your ‘championship game’ for the company this year? What specific goals must you set for yourself to get there?

Understanding Strengths and Weaknesses

  • Think of yourself as a player reviewing game tapes. What insights can you glean from your leadership experiences this past week? Consider the interactions that worked well and those that need refining to help illustrate your strengths and areas for growth.
  • Like a coach crafting game strategies around star players, how can we leverage your unique strengths to maximize your leadership impact? Let’s build a playbook that highlights your strengths and minimizes your weaknesses.
  • Think of a sports match where an athlete had to adapt their game plan on the fly. How can you apply that agility to your leadership style and step out of your comfort zone to do so?

Building Resilience

  • Consider the mental preparation athletes undergo before a competition like downhill skiing or running a marathon. How can you cultivate resilience and mental toughness to tackle the challenges and setbacks on your leadership journey? How can you channel your inner athlete and train your mind for peak performance?
  • Envision yourself in high-pressure moments, much like elite athletes in the heat of the game. What strategies can you adopt to stay focused and motivated amidst adversity or uncertainty?

Communication and Motivation

  • Imagine your team as a basketball team, relying on effective communication for success. How can you refine your communication skills to inspire and motivate team members? How would you craft a message like a seasoned coach, rallying your team with clear direction and unwavering support?
  • Consider the principles of sportsmanship and teamwork as pillars of trust and credibility. How can you embody these principles to build strong relationships among your colleagues and stakeholders? How can you lead by example, fostering a culture of respect and collaboration on and off the field?

Continuous Learning and Improvement

  • Visualize training for a marathon, constantly pushing your limits to reach peak performance. How can you prioritize continuous learning and self-improvement as a leader? Embracing the mindset of a lifelong learner, how can you expand your knowledge and skills?
  • Like an athlete seeking feedback from coaches and teammates, how can you solicit feedback to fuel your personal and professional growth? How can you open yourself to constructive criticism and use it as fuel to propel you towards excellence?
  • Like refining a golf swing, what small adjustments can you make in your leadership approach to yield big results? What small changes can we implement in our processes or strategies to yield significant improvements?

For Teams

Clarifying Vision and Goals

  • Envision your team as a cohesive unit, united in pursuit of a common goal like any high performing team in sport, especially a team in Olympic sports like rowing. How can we ensure alignment and clarity of purpose among team members towards achieving organizational objectives? How can you paint a vivid picture of success, inspiring collective action, and unwavering commitment to the vision?
  • Think of your team as a World Cup team, rallying around a championship dream. What strategies can we employ to articulate a compelling vision that ignites passion and fosters a sense of shared ownership within the team? How can our team purpose and vision resonate with each team member, fueling their drive to succeed?

Fostering Team Cohesion

  • Reflecting on the camaraderie and cohesion of championship-winning sports teams, how can we cultivate a culture of collaboration, trust, and mutual respect within our team? How do we foster an environment where every team member feels valued and supported, building bonds that withstand any challenge?
  • Formula One teams rely on the collective performance of many functions who rely on each other for victory. What team performance activities or exercises can we implement to strengthen interpersonal relationships and enhance collaboration among team members? How can we foster connection beyond the workplace, forging a tight-knit team that thrives on unity and camaraderie?

Communication and Collaboration

  • On the field, effective communication is key to success. How can we improve our team’s communication channels for better coordination?
  • Think of a sports team huddle. How can we ensure everyone’s voice is heard and valued in our team discussions? How can we improve our team’s communication channels to ensure everyone is on the same page?

Team Dynamics

  • Consider your leadership team as a starting lineup. How can you ensure everyone is playing to their strengths and supporting each other?
  • In a relay race, each runner passes the baton smoothly. Are there any handoffs within our team that need refining? How can we ensure everyone is securely anchored and supporting each other as we ascend towards our goals?

Team Role Clarity

  • Professional sports teams are an amalgam of players with distinct positions and roles to play, often in a defined system of performance. How can we optimize the allocation of tasks and responsibilities to leverage the unique strengths and expertise of each team member in the context of our operating systems? How can we assign roles that align with individual strengths to maximize team performance?
  • In football, especially, playbooks are used to meticulously outline each player’s responsibilities for each play. How can we ensure clarity and accountability in role expectations, and what mechanisms can we establish to track progress and measure performance? How can we define clear expectations and hold each team member accountable for their contributions, and excellence across the board?


  • In sports, players take ownership of their roles and responsibilities. How can we hold ourselves accountable for our individual and collective contributions?
  • Consider our team as a sports lineup. Are we each playing our positions effectively, or do we need to adjust? How do we ensure everyone feels empowered to take ownership of their actions?

Adapting To Change

  • Even with great preparation, team sports are equally unpredictable. Imagine your team as athletes on a field, ready to pivot in response to changing game conditions. How can we cultivate a mindset of flexibility and resilience to navigate uncertainty and challenges in our operating environment? How do we embrace change as an opportunity for growth, and learn to adapt quickly and decisively to overcome any obstacle?
  • Championship-winning teams are always prepared to adjust their game plan in the face of adversity. What strategies can we employ to anticipate and proactively address potential obstacles or disruptions? How can we cultivate a culture of innovation and agility and empower the team to thrive in any situation?

Celebrating Success and Learning from Failure

  • Reflecting on the post-game rituals of teams celebrating victories and analyzing defeats with equal vigor, how can we create a culture of reflection and continuous improvement within our team? How can we embrace failure as a steppingstone to success, learning from mistakes and using them as fuel for growth?
  • Consider championship celebrations of sports teams, commemorating milestones, and achievements along the journey. How will we celebrate these accomplishments?



Steve Schloss

Coach and advisor to CEOs, executive leaders and teams. Sharing thoughts, observations, and ideas around leadership and culture. Trying to break 80 more often.