A Conversation with Jonathan Rosenfeld, Head of Trium’s Coaching Practice

1. What inspired you to shift from being a therapist to a CEO coach?

First off, executives are action-oriented and are typically already highly accomplished before they get into their executive role. They are generally going to use the coaching they receive – they put it work, and that’s really gratifying. I also love working with executives because I learn so much – I’m the domain expert, but he or she is the practitioner. That synthesis, of learning through what they do with my advice, generates an ongoing feedback loop, and it’s very dynamic.

Second, I like working with systems. The great majority of my work has been with CEOs, and these CEOs are leaders of systems. Particularly at startups, the system is often an externalization of his or her inner world. So our work together can be healing personally – and healing and empowering for the organization – which cranks up their probability of success.

Finally, I like taking risks – which is kind of unusual in both the coaching and therapy spaces. This can be a huge boon for CEOs, who are really looking for people who can be honest with them, and I love that. I always hope I get the opportunity to take a huge risk with a client and see how they react, perhaps, for instance, by telling them something they don’t want to hear (but need to).

2. Who or what do you consider to be the biggest influence on your approach to coaching? 

Gosh, this is a hard one. I don’t have any mentors, specifically, but I have a lot of influences, like the Milan School theoretical model. I like to think of myself as a change strategist, so every leader who has responded to change as an evolutionary process rather than something to block or manage has been inspiring to me. Mikhail Gorbachev and Franklin Roosevelt are two examples who are right up there at the top – overseeing peaceful transitions with overtones of servant leadership.

3. Why do you love being a part of Trium?

For a long time, I was an individual practitioner, and now I’m part of an amazing community. Each day stretches me – intellectually, interpersonally – and everyone who works here is committed to having forthright conversations about who we are and what we do in service of our clients, not to mention with regards to our own growth as people and as leaders.

4. If you could only ask one question of a new coaching client, what would it be and why?

How did you get in this room?

This almost isn’t fair because it’s something I routinely ask as my opening question. There are arguably a lot of people who would be qualified for any one role – so what’s your journey? What’s are the choices you’ve made? Parenthetically, I’m listening for people’s creation story. I end up hearing stories about people’s extraordinary but also implicit strengths, as well as about their false attributions for their success. The stories are full of surprises. Focusing on strengths while also correcting for erroneous correlations between success and actions is often instrumental for growth.

5. Where would you love to coach, and why?

I would like to work at the White House. During both the Clinton and Obama administrations I worked with senior staff and cabinet-level folks. At my heart, I’m a policy wonk, and I’d love to be a part of facilitating the highest-quality policy as a derivative of people having high-quality conversations with one another. And of course, government and policy are nothing but a giant system, so it’s absolutely fascinating.

6. What is a hobby or interest you have that others might find surprising? 

I collect old atlases. I like to track the evolution of cities and the movement of political boundaries. Remarkably, among all of my friends, there is not a single one who shares this interest…

7. What do you think your clients most appreciate about what you bring to the table?

I believe it’s listening. I can be deeply, deeply empathic to what’s going on in people’s heads and to represent and say what people need in a way that they can hear it and know what to do with it. After years of a mindfulness practice, what’s really quite helpful is that I can listen without a lot of distraction from my own thoughts or my own voice getting in the way. At the same time, I’ve had prospective clients ask me this – one thing I’ve told people is that, as a diagnostician, my orientation around systems theory makes me able to see things that are opaque to others.  Thanks to my training, I’m a hard-core right brain thinker who can pass as a left brain. So when you bring all of that together, it results in really unusual insights that are highly usable.