Meet The Coach: Robbie Ross

Core belief: we can hold ourselves to high standards & produce strong work without treating each other poorly. To think otherwise is to fundamentally misunderstand the power of effective management.

What they’re saying:

“This was different from all other coaching I’ve had. It’s been about taking accountability for my own role in my challenges, finding a way to vent, and then finding a path forward. You have been such a lifeline and source of joy for the past couple of months. I really can’t thank you enough for being my confessional, go-to strategist, and general sounding board.”

Rigor and basic kindness are not mutually exclusive.

A long-time Chief of Staff, Robbie’s spent over 15 years in “#2”-like roles within mission-driven organizations, overseeing questions of org structure, team management, culture building, and day-to-day operational execution.

With experience scaling & leading both non-profits and for-profit mission-driven companies, he borrows from both worlds. He’s exclusively worked for founders, operationalizing big visions and bold new ideas––so he’s used to navigating ambiguity, risk, and quickly shifting priorities.

Robbie’s always got one eye on culture: in a world where “clear is kind,” what’s it look like to design for autonomy, creativity, and accountability, equipping your team with the tools and trust they need to deliver incredible work?

As the Chief Partnerships Officer of Cultivate, Robbie oversees the Team Assembly community of 100+ senior leaders in social impact who receive both cohort-based and 1:1 executive coaching. He draws from this exposure to isolate best practices and share back in bitesize ways.

You can find him on LinkedIn and read more hot takes on Medium.

What they’re saying:

“Our time together has felt not just helpful but also necessary. There were a few moments of you asking ‘What about this?’ that dramatically shifted where I was headed, and that was huge for me.”

“It’s such a valuable space for reflection and strategic thinking, which to me is the hardest thing to make room for in my calendar. Even when we’re workshopping something small, you’re there reminding me how it fits into the big picture.”

Why hire Robbie as a coach:

  • First-time leaders and founders frequently wish to inhabit more "executive presence" and/or gain exposure to new ways of thinking about org-wide decision making. We help diagnose structural patterns that they otherwise might not have had enough experience to spot quite as easily themselves the first time around.

  • We frequently work with leaders whose organizations are engaged in big structural shifts––e.g., moving from a single Executive Director to a co-leadership model, or rolling out a new org chart design that elevates or demotes various people across the team.

  • We regularly work with leaders who are navigating tricky dynamics with their boss (if they're not the #1 themselves) or across their senior leadership team. This typically involves focusing more on setting explicit expectations, focusing on outcomes, engaging in more honest conversations, and leaning out of conflict avoidance.

  • In some cases, leaders simply feel like their senior leadership team isn't quite stepping up into its full potential, even without obvious strife. In these instances, we frequently partner with more than one senior leader in the org to help them interrogate what it would look like to think bigger / more ambitiously about their own role, usually in a more cross-functional way.