FREQUENTLY ASKED QUESTIONS
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We create a sacred space where high-capacity leaders explore what's possible, both for them and their organizations. We help executives get unstuck, gain perspective, make better decisions, upgrade key skillsets, and accelerate progress toward what matters most.
The coaching process blends reflection and action—clarifying vision, addressing obstacles, and building habits and mindsets that sustain growth long after the session ends. Learn more about Rooftop Coaching’s philosophy here.
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When done right, coaching isn’t an expense—it’s an investment with a measurable return.
Independent research confirms that coaching:
Creates a 788% ROI from productivity and retention gains (MetrixGlobal)
Increases individual performance by 70%, team performance by 50%, and ↑ organizational performance by 48% (ICF via American University)
Doubles the likelihood of a successful leadership transition (McKinsey & Company, 2023)
At Rooftop Coaching, that impact shows up not only in metrics but also in how leaders think, feel, and lead—with greater alignment, focus, and courage.
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Coaching is a game-changing investment because it begins where real transformation happens — with the leader’s own clarity and capacity. While consultants offer solutions, coaches expand a leader’s ability to generate them. While therapy heals the past, coaching mobilizes the future. And while mentors share what worked for them, coaches help clients uncover what will work for them.
Rooftop’s approach leverages all of these modes, but we always start with coaching to ensure the conversation begins with deep inquiry — uncovering root issues and unlocking insights — before layering in experience or expertise to amplify the client’s own intuition and direction.
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Most leaders begin with a discovery session to clarify goals and fit. From there, coaching typically includes two 60-minute sessions per month—held virtually or in person—anchored by occasional personal retreats for deeper insight and transformation.
Every engagement is customized, but most follow a rhythm of:
Learning – Gain fresh insight into yourself, your context, and the dynamics around you.
Vision – Clarify the desired future state and define what success looks like.
Strategy – Explore creative pathways and practical options for getting there.
Commitment – Identify the highest-impact next steps and commit to them with clarity.
Action – Follow through with discipline and accountability to build momentum.
Learning (Again) – Reflect on outcomes, celebrate progress, and recalibrate based on what worked—and what didn’t.
Growth and traction continue between sessions through targeted follow-up and reflection.
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Most of our clients lead small to medium-sized companies, with a few nonprofit leaders in the mix each year.
Our ideal clients share four qualities that spell HIGH—a fitting word for a coaching practice that helps leaders rise above the noise and see from higher ground.
Hungry – they are committed to changing the status quo
Influential – their growth impacts others
Gifted – they have strengths worth multiplying
Humble – they’re open to learning, feedback, and change
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A change of place plus a change of pace equals a change in perspective.
When leaders step out of the noise of daily demands, they begin to see their leadership, relationships, and life with new clarity. Our 1:1 leadership intensives—most often offered in Jackson Hole, Wyoming and Kansas City—create that space, tailored to each leader.
These retreats perfectly complement ongoing coaching.While regular sessions sustain momentum and address challenges in real time, intensives deepen trust, accelerate growth, and surface insights that might take months to emerge otherwise.
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All of our coaching—whether with individuals or teams—shares common threads: clarifying vision, leveraging strengths, making values-based decisions, removing roadblocks, and achieving results.
But team engagements add two powerful dimensions. First, alignment—ensuring the whole team is rowing in the same direction with shared vision, values, priorities, and roles. Second, healthy dynamics—building vulnerability-based trust, fostering productive debate, and strengthening focus and accountability.
We see tremendous value in doing both individual and team work. When we coach individuals, we help them see how their growth impacts the whole team. When we coach teams, we draw on our deep understanding of individual development to address the personal dynamics that can hold a team back.
And we have many clients that engage us to do 1:1 coaching and team facilitation in tandem, which multiplies the impact. This integrated approach helps leaders and teams climb higher—faster, healthier, and with greater unity.
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As goes the leadership team, so goes the company.
We mostly work with executive teams, founders, and ownership groups because their alignment drives everything else. When they’re clear, connected, and pulling together, the whole organization moves faster and healthier. When they’re not, everyone feels it.
We help teams surface what matters most, clear obstacles, and create shared momentum—so they can get back to the energizing work of building a thriving business.
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Teams that work with Rooftop Coaching grow in both clarity and cohesion. They leave with a shared vision, clear priorities, and stronger alignment around what truly matters. Communication improves, friction decreases, and accountability rises—because everyone understands the destination and their role in getting there.
You can also expect renewed energy and trust. Our work helps teams move from polite agreement or quiet frustration to open dialogue and real collaboration. The result is a leadership team that’s rowing in the same direction—focused, connected, and confident in how they lead together.
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Confidentiality is the foundation of effective coaching—and a requirement of the International Coaching Federation (ICF) Code of Ethics. Nothing shared in a coaching conversation is disclosed without your consent. The trust created in that space is sacred—it’s what makes the work transformative.
The coaching process blends reflection and action—clarifying vision, addressing obstacles, and building habits and mindsets that sustain growth long after the session ends. Learn more about Rooftop Coaching’s philosophy here.
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The name was inspired by a favorite story from the New Testament—a paralyzed man whose friends helped him find healing by creatively and boldly overcoming barriers. When they couldn’t reach Jesus through the crowd, they climbed onto the roof, cut a hole, and lowered him down. There he found healing, forgiveness, and a community in awe. His life was changed forever—and he didn’t get there alone. The parallels to coaching are hard to miss.
We also love what the name represents: hospitality—a sacred, courageous space for leaders to step back from the daily grind; climbing—the pursuit of new heights and fresh perspective; and celebration—as in, “shout it from the rooftops.”
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It’s often a natural choice for a company to fund coaching—because the business impact is real. Research shows leadership coaching delivers a 5–8x return on investment and drives 70% improvement in individual performance and 50% improvement in team and organizational performance. So the investment in the leader is an investment in the team.
If you’d like to explore this further, here are a few practical recommendations:
1. Show the business value.
Frame coaching as a performance investment, not a perk. When leaders grow, their teams grow—and the organization benefits through stronger alignment, engagement, and results.2. Tie your goals to business outcomes.
Connect your development to priorities your company already cares about such as increasing sales, executing a key change initiative, or improving retention of key staff. We can help you link your goals to measurable business results.3. Leverage professional development budgets.
Many organizations already fund leadership development or continuing education—and coaching often qualifies. In fact, it typically delivers greater impact than traditional training because it’s tailored, sustained, and accountability-driven. Think of it as a year-long, personalized workshop. It also enhances training effectiveness: studies show a 4x increase in retention and application of learning when coaching is added.4. Propose a shared investment.
If there’s hesitation, offer to co-invest. Even covering a portion yourself signals commitment and often prompts your company to meet you halfway.At Rooftop Coaching, we help leaders connect personal growth to organizational impact—so everyone wins. If you’d like to explore that alignment, let’s talk.
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Let’s talk.
The first step is a complimentary discovery conversation where we clarify what you’re after, what’s getting in the way, and whether coaching is the right fit. Many leaders gain so much clarity from this first session that this session alone changes their trajectory—sometimes even without further coaching.
If it feels like a fit, we’ll design a plan that meets your goals and timeframe. Either way, you’ll walk away with fresh perspective and a clearer next step.