Executive Coaching

Solve the Unsolvable

Solve problems that have no known solutions.

Tackle questions that have no right answers.

Develop tools to self-coach and create your own advice.

Executive Coaching

    • Transitioning into or out of a role or organization

    • Navigating life in the wrong role or the wrong workplace

    • Losing touch with what you loved about your work

    • Losing sight of your core values

    • Launch new teams well with a tactical formation process. Or lead a seasoned team back to basics to establish a stronger foundation.

    • Address butting-heads with board members and/or team members

    • Navigate life on highly-political teams and solve collaboration-breakdowns with key partners

    • Improve comfort with delegation and shift to big-picture thinking

    • Sell organizational change or out-of-the-box ideas to scared, apathetic, and intrenched stakeholders

    • Coach, mentor, and lead direct reports toward personal growth and business outcomes

    (See Team Coaching)

  • Set a new direction for your team, your org, or yourself.

    Self:

    • Clarify personal interests and ambitions

    • Identify strong and weak points in your performance

    • Clarify areas where growth is truly exciting to you

    • Strategically develop growth plans

    • Execute on plans with accountability

    • Adapt as interests and needs evolve

    Team & Org:

    • Take stock of existing vision, execution, and performance—across products, services, and/or company culture

    • Define vision for future growth

    • Set team and organizational objectives

    • Execute and adapt

  • Coaching to boost individual creativity and/or grow creative-team leadership skills.

    Develop solo skills and tools for creative problem-solving:

    • Finding enthusiasm on boring problems

    • Boosting personal creativity & getting unstuck

    • Selling innovative ideas to colleagues and stakeholders

    Or else solve the problem now:

    • Tackle a creative problem

    • Test & iterate on your ideas

    • Decide among possible solutions

    • Recover from failure

    Learn how to lead your team to innovation, even when your team doesn’t believe that they’re “creative.”

    • Foster a culture of innovation

    • Choose the right people for your innovation team

    • Overcome apathy: find the fun in any problem

    • Overcome negativity: respond to the chorus of “No” and the pain of failure

    • Lead productive brainstorms

    • Shake up “the way we’ve always done it” 

    See the Innovation Hub

    • Tackle challenges in work/life balance

    • Find the root of workplace apathy and boost personal enthusiasm

    • Pivot to a new role or company that better suits your passions, values, skills, and needs

  • Get off Zoom, get away from the desk, and get on your feet. It’s out in the world and out of our heads that the greatest discoveries are made.

    Learn more about the Trespass Leadership Project.

Inquiry-based coaching.

An inquiry-based process designed to help executive leaders coach themselves and others—developed and tested over a decade, in partnership with more than 50 CEOs, founders, and senior executives, hailing from multi-billion dollar hedge funds, Nobel-winning teams, and brands like McKinsey, Google, NASDAQ, and Microsoft. Inspired by principles of human-centered design and learner-centered pedagogy.

CREED OF THE ANTI-COACH

You know the answer. You just haven’t said it out loud yet.

Traditional coaching is all about knowledge transfer. Someone else seems to know the answer, and they transfer that knowledge to you. But in crisis, in decision, and in creation, leaders and innovators need to find their own answers. In Leadership Coaching, your coach uses deep interrogation to empower you to lead yourself and others. It’s a process that generates better answers, lasting solutions, surprising innovations, and a capacity to coach others using the same methodology.

Start With a No-Fee Session