Case Studies

From aligning vision and strategy to strengthening team dynamics and navigating complex challenges, these case studies showcase how we help organizations unlock their potential.

From Misalignment to Momentum

In a SaaS tech organization, a fragmented leadership team and lack of clear strategy hindered progress. Through tough feedback and a breakthrough annual planning offsite, we aligned the CEO’s team on a bold vision, clear priorities, and a target customer—doubling revenue and customer growth within a year.

  • Interviews with the leadership team revealed a lack of an overarching corporate strategy, which many attributed to the CEO's conflict-averse approach and reluctance to make tough decisions. In the absence of clear strategic direction, individual leaders and their teams defaulted to optimizing priorities based on their own functional perspectives, leading to a fragmented approach to decision-making.

  • Provided tough, incisive feedback to the CEO and designed a multi-day offsite aimed at: aligning on the organization's vision, developing a cohesive corporate strategy to address long-standing strategic questions (e.g., target customer segments, competitive differentiation, geographical focus), and fostering stronger collaboration and trust within the leadership team.

  • The leadership team achieved alignment on an overarching corporate strategy and a specific target customer segment—a significant breakthrough, especially as the CEO overcame initial reluctance to make decisive choices. This clarity generated excitement and energy within the team, enabling them to define focused priorities for the coming year. Since the strategic offsite, the business has more than doubled its revenue and customer base.

Growth & Integration Under Pressure

The CEO of a private equity-backed technology company faced high stakes following a recent acquisition. We facilitated offsites and provided CEO coaching to unify the business, build a strong leadership team, and drive measurable results—leading to thriving performance and growing market share.

  • As the organization navigated the post-acquisition transition, leaders from the acquired company voiced significant fear and uncertainty about what the future held and what to expect from the CEO of the newly combined organization.

  • Designed and facilitated multi-day offsites to establish a shared vision for the post-acquisition business, foster trust, and define key ways of working, including decision-making processes, team norms, and meeting cadence. Provided ongoing CEO coaching and advisory on unifying the organization, building a high-performing leadership team, shaping strategy, setting priorities, and managing the performance of key leaders.

  • The business is thriving, demonstrating exceptional performance with consistent growth in market share. This success stands in stark contrast to competitors, whose market share continues to shrink, further highlighting the organization’s strong position and momentum in the industry.

Building Trust & Breaking Silos

A newly appointed CEO of a large national non-profit faced tensions within the leadership team and a siloed organization. We helped align the team on a bold five-year vision and strategy, earning board approval and transforming team dynamics with stronger trust and more strategic collaboration.

  • A lack of clarity around the strategic direction—and uncertainty about who should be involved in shaping it (the board, CEO, or leadership team)—was causing widespread confusion and frustration. The CEO’s actions were eroding trust with leadership team members, while the team itself lacked the skills to openly address difficult issues, leaving key challenges unresolved.

  • Over an intensive six-month effort, including multiple leadership team offsites and bi-weekly meetings, we achieved clarity and alignment on the organization’s vision and strategic direction and developed a cohesive five-year strategic plan. Trust was strengthened across the leadership team, including between the CEO and team members, while leadership processes such as decision-making and meeting efficiency were significantly improved. Together, we tackled complex business challenges like fundraising and growth, with the CEO receiving six months of dedicated 1:1 coaching to support their leadership journey.

  • The CEO and leadership team successfully aligned on a five-year vision and strategy, earning enthusiastic approval from the board of directors. Leadership effectiveness and team dynamics improved significantly, with higher trust levels and a stronger focus on strategic, collaborative dialogue.

Unleashing Leadership Potential

Over a six-month coaching engagement, we supported a newly promoted Vice President leading a 100+ person organization and overseeing areas beyond their expertise. Facing challenges with prioritization, an unsustainable pace, and self-doubt, we helped them build confidence, clarify their strengths, and develop sustainable strategies for effective leadership.

  • In examining why the pace felt unsustainable and prioritization remained challenging, two key issues emerged: impostor syndrome—stemming from leading a large team and managing people with technical expertise beyond their own—which drained energy and undermined self-confidence, and a tendency to take on too much, driven by a fear of saying no.

  • During the six-month coaching engagement, the client experienced two major breakthroughs. The first was recognizing that they were operating from a place of fear rooted in a major career setback over a decade ago. This past experience had driven a mindset of “I have to say yes to everything and can’t drop any balls, or my career will crash again.”

    The second breakthrough came from confronting the inaccuracy of their self-perception. Despite being overly self-critical about their leadership and performance, a 360-degree feedback process with peers, direct reports, and their direct manager—one of the top ten leaders in the enterprise—revealed a different reality: the client was excelling across multiple high-stakes situations.

  • The client realized their self-perception was misaligned with reality, recognizing that their impostor syndrome was self-created and that they were performing at an exceptionally high level. With a newfound awareness of their strengths and contributions, they let go of fear-driven behaviors, stopped feeling compelled to say yes to everything, and released the pressure to be perfect. By the end of the coaching engagement, they felt confident, empowered, and ready to move forward and thrive.

Balancing Vision
& Resilience

During two six-month coaching engagements, we worked with a C-level executive navigating organizational shifts, cultural evolution, and staff reductions. By honing their vision, prioritizing effectively, and fostering confidence, they earned praise from the CEO and achieved greater ease and effectiveness in their role.

  • Facing constant, shifting demands from the CEO and peers, the executive and their organization were under significant pressure to deliver without sufficient time or resources. We helped them prioritize effectively and adjust timelines, creating much-needed breathing room for both the executive and their team.

  • Served as a trusted sounding board and advisor to the executive, helping them craft a clear vision and strategy for their function to guide prioritization. Supported them in managing work effectively amidst resource constraints and navigating an ambitious CEO who frequently proposed new initiatives, while also focusing on establishing a sustainable pace to ensure long-term success.

  • The CEO has been highly pleased with the executive’s performance and the progress of their organization. The executive is now leading with greater confidence and ease, managing challenges more effectively, and experiencing a noticeable reduction in stress.

Letting Go
to Level Up

In a six-month coaching engagement, we helped a newly promoted Vice President overcome perfectionism and fear of failure. They embraced their ambition, elevated their executive presence, and learned to delegate effectively. By focusing on team development and accountability, they shifted to a more strategic leadership approach, driving sustainable success with greater confidence and clarity.

  • At the start of the engagement, the client expressed no desire to advance further in their career. Through deeper discussions, it became clear that this reluctance stemmed from a fear of failure, rather than a genuine lack of ambition.

  • Through the coaching process, the client strengthened their confidence and embraced their ambition to progress into a bigger role, aligning with the organization’s goals for their leadership growth. They let go of the need for perfection and recognized that sustainable performance required building their team’s capabilities. Previously operating at both VP and Director levels due to the team’s underdeveloped skills, the client realized they needed to focus on accelerating their direct reports' growth or, in the medium term, make tough decisions about their roles. This shift empowered them to lead more strategically and effectively.

  • Recently promoted to Senior Vice President, the client embraced their ambition to take on greater responsibilities, aligning with the organization’s vision. Letting go of perfectionism, they recognized the need to strengthen their team, holding direct reports accountable, accelerating development, or making tough decisions. This shift empowered them to lead with greater focus and impact.

Testimonials

“Howard has become an invaluable part of my professional life. He is my trusted advisor, coach and friend. His thoughtful insights, direction, candor, nudging, and thoughtfulness have been life changing for me. My only regret is that I didn't have him in my corner sooner.”

— Nikki Kraus, CFA, Chief Executive Officer, Strategic Investment Group

“A leadership whisperer — that’s the best way I can describe Howard. He is able to uncover things that you didn’t even know needed to be uncovered.”

— Elissa Salas, CEO, College Track

“Other coaches never look at why things keep happening or why you believe things to be true. Howard goes deeper and is always pushing me to think more, to do more pattern recognition and systemic change rather than just tactical problem solving.”

— Amanda Richardson, CEO, CoderPad

“On the surface, coaching is often seen as a “nice to have.” However, when well executed, it’s anything but simply “nice”. The work Howard and I did together allowed me to discover my true leadership strengths and taught me how to work through my weaknesses. It changed my organization and it changed me.”

— Amy Mack, CEO, The Institute for Functional Medicine

“My work with Howard has been transformative. He made my interests and success his paramount concern and his methodology has helped me tremendously in my career.  The depth of the work that we accomplished goes to the heart of how I now think, perceive, and act as a leader. I recommend Howard to anyone looking to accelerate their career and leadership skills.”

— Stephanie Kim, Vice President/General Manager, Fenty Beauty, Skin & Fragrance (LVMH)

“One of the best decisions of my life was to engage Howard as a coach for my own leadership development. The impact and positive outcomes that resulted from my coaching engagement with Howard were huge and immediate.”

— Ashish Rawal, Group Vice President and Chief Technology Officer, Federal Reserve Bank of San Francisco

“He helped me cut through the non-essential parts and allowed me to show up just the way I need to be my best self. He helps you focus on the essential.”

— Scott Donohue, Partner, NextWorld Evergreen

“Howard is a critical thought partner for me as a leader and the strategic direction of my team's work. As a coach, he provides you with insights to help you grow and how to best align your resources and strategy to deliver meaningful outcomes. It’s a unique blend for a coach.”

— Antoine Andrews, Chief Diversity and Social Impact Officer at SurveyMonkey

“He’s able to work in many dimensions. He can be knitting together a corporate landscape, what’s going on in the environment, what do you need to do, and what the people around you are looking for. His business smarts are a strength. He comes in and he’s ready to talk in your language, even about the way that your firm runs and the org chart and what it all means. Some coaches don’t even know the language of our industry.”

— Heather Pelant, Partner, Baker Street Advisors

“He is so authentic and cares so much. He wants to see you succeed and is invested in it. You end up feeling like you have an ally. He cares a lot about creating not just solutions, but a better framework from which you can approach your job and try to be a better human being.”

— Tim Mahedy, Chief of Staff to the President, Federal Reserve Bank of San Francisco