Team Coaching

Grounded leadership builds performant teams. Clarity and alignment that scale beyond one leader.

When leadership teams lose trust, clarity, or direction—I help them realign, re-communicate, and recommit. I'm not just a facilitator; I'm a strategic team architect brought in to realign trust, power, and communication dynamics that determine your company's trajectory.

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Core programs that transform teams

These programs are grounded in the Middle Path framework—a proven methodology used across 160+ startups and 15+ top tier Venture Capital firms. I'm one of only a few coaches certified to teach it.

Executive Team Alignment

Realigning trust, power, and communication when high-performing individuals struggle to function as a cohesive leadership unit. We identify core breakdowns and rebuild the foundation for strategic collaboration.

New Executive Onboarding

Using the Middle Path framework to accelerate trust and integration when bringing senior leaders into existing teams. We surface early friction points and build shared understanding across functional areas.

360 Review Programs

Strategic assessment of leadership effectiveness with structured process, timing, and follow-up. Not just feedback collection—transformation of how leaders see themselves and show up.

Leadership Team Retreats

Deep strategic alignment combined with team dynamics repair. Intensive sessions that address both business strategy and interpersonal effectiveness.

When teams need strategic intervention

Specific triggers that require immediate attention:

  • New executives struggling to integrate with existing leadership culture
  • Team dysfunction and splintering that impacts strategic execution
  • Scaling challenges where individual contributors become team leaders
  • Executive accountability breakdowns and recurring conflict patterns
  • Trust repair between leadership after organizational stress

Team size and stage parameters:

  • Leadership teams of 5-12 people
  • Series A through pre-IPO companies
  • Teams experiencing rapid headcount growth
  • Organizations navigating significant strategic shifts

The transformation process

step 1

Initial Assessment

Stakeholder interviews and team dynamics analysis to identify core patterns and friction points

step 1

Strategic Design

Customized program based on specific team needs, typically a 2 day offsite with follow-on day long sessions as needed

step 3

Implementation

Combination of group sessions, individual coaching, and practical application of new frameworks

Workshops are highly interactive and primarily focus on your company and team specific issues.

step 4

Integration

Six and twelve month checkup sessions where we practice using skills learned on current company issues

step 5

Onboard

Onboarding for all new leadership team members plus key stakeholders as appropriate

Team transformation stories

Repairing Trust Post-Funding
A Series B startup had just closed major funding, but the executive team was "walking on eggshells" with decision-making stalling and interpersonal tension rising. Through structured coaching sessions grounded in Middle Path principles, we named unspoken dynamics, clarified expectations, and rebuilt psychological safety. The result: team meetings became "the most aligned and honest they had ever been."
Accelerating Trust with New Executives
A recently hired C-level executive struggled to integrate despite strong credentials, creating tension and slowed progress. We ran an onboarding-focused engagement with stakeholder interviews, profile reviews, and shared expectations workshops. Within two months, the executive became a key driver of cross-functional alignment and delivered on major company-wide projects.
Moving from Dysfunction to Clarity
A growth-stage leadership team experienced recurring friction—meetings derailed, decisions were revisited, and subtle power struggles undermined progress. Through a 3-month engagement including 360 team assessment and facilitated sessions, we identified core breakdowns in trust and decision rights. The team shifted from reactive to proactive culture, with leaders naming tensions early and collaborating more effectively.
"We're acting more like a leadership team and less like a group of smart individuals."

What changes when we work with your team?

Tough conversations become honest ones

instead of avoided or deflected

New leaders integrate faster

and build trust with existing team members

Strategic priorities become shared commitments

rather than competing agendas

Dysfunction transforms into clarity

about roles, expectations, and accountability

"Being CEO is lonely; this is just a fact of the job. Rick has been my sanity check, my second set of eyes, and a core piece of my accountability. It's hard for anyone else to call you on your BS, but a great coach can do just this."

Tristan Handy - CEO, DBT Labs

I think that anyone who is looking to grow as a CEO would benefit from partnering with Rick. He isn't going to tell you what to do, but will help you explore your strengths and weaknesses in order to develop some guidelines around how you can continue to grow and evolve as an individual, leader and team mate. I was 5 years into my CEO journey when Rick and I got engaged and I felt I could have benefited from the relationship even earlier in my journey.

John Jahnke - CEO at Tackle

"As a repeat founder, I wasn't entirely convinced coaching was something I needed. But working with Rick has changed that perspective. He's been a steady drumbeat of guidance through some of the most complex and high-stakes moments of my career. I can say with confidence that I've grown more as a leader with Rick in my corner than I would have on my own."

Bob Moore - CEO, Crossbeam

"Rick guides you toward better pathways, creating a new mental model you can apply more broadly. After coaching, I cringe whenever I hear the word 'should'—I now approach decisions with genuine clarity."

Alex Page, CEO, Nillion

"Rick has helped me slow down and gain clarity—not just in decision-making, but in how I see myself as a leader. I've become a more effective and trusted partner to my peers and exec-level counterparts."

Meg Pittman - Chief People Officer, DBT Labs

"Rick has been consistently rooting for me personally as a CEO—his direct honesty and genuine advocacy have transformed my leadership, helping me confidently navigate tough decisions and challenging team dynamics."

Jerome de Lafargue - CEO Zeroheight

Investment and commitment expectations

This isn't light facilitation. It's strategic intervention that requires commitment from every participant and leadership from the top. Change doesn't come without effort.

Time Commitment

Significant but strategic—intensive phases followed by integration periods

Participation

Full leadership team engagement required for maximum impact

Duration

Typically 3-6 months depending on scope and complexity

Investment

Commensurate with the strategic value of high-functioning leadership

Assess your team readiness

Schedule Team Assessment Call