Benjamin Jackson

1:1 coaching for conscious leaders

At some point in everyone’s career, the job asks something of you that it didn’t ask before. Your CEO is pushing you to lead, or you’ve joined a new team with an unfamiliar culture, or a promotion puts you in charge of your peers.

I was struggling to connect with folks or translate my experiences to them in a way that made sense. I got more out of our first coaching session than out of 4-5 months of my last coach. One of the breakthroughs was when you used the phrase “communication is what the listener does.” I was so focused on trying to refine the way that I share my ideas, that I was less focused on how it was landing. By reframing things in terms of medium and long-term goals, it’s helped me develop a little more patience.
Liam K.
Liam K.
Chief of Staff
Tortorella

Who this is for

Some of the patterns I’ve noticed among my most successful clients:

  • They’re curious: they read books for pleasure, and consume a wide range of media.
  • They’re navigating an identity shift at work: e.g. from operator to leader, big corporate to startup.
  • They embrace new ideas, and are willing to change their minds when challenged.
  • They have a strong moral compass, and are willing to stand up for their beliefs.
In my new role, I just wanted to have someone help me be successful, understanding a new culture, a new team dynamic. Ben helped make my strategy more concrete, make my meetings more impactful. It’s the voice in the back of my head. Where I was day one and where I am now is light years away. What I was craving was the trust and I think I got it.
Daniella C.
Daniella C.
Human Resources Director
Gagosian

Who it’s probably not for

  • You’re looking to find your inner purpose. I work best with people who already know what they want.
  • You want scripts, frameworks, or best practices. My clients and I figure things out in the moment.
  • You’re too busy to work on yourself between sessions. I share a lot of books, articles, and podcasts.
  • You need encouragement more than you need to be challenged. I’m kind, but honest and direct.

How the work goes

Sessions focus on whatever you’re dealing with in the moment. Some days, that might be a problem with a direct report. Others, it might be a high-stakes conversation with your boss. I tend to find the things you’re not quite able to articulate and lay them bare so we can work on them directly.

Ben’s coaching and 360º review were game-changers. The self-awareness, it’s almost like a superpower. Honestly, I got more out of it than my MBA. I also moved up to bigger leadership roles, even jumping from a startup to managing a large team at a mid-sized company.
Gus F.
Gus F.
Chief Technology Officer
BÆRSkin Tactical Supply Co

What working together looks like

We work in three–month blocks. We meet weekly or every other week for about an hour, usually by phone so you can take the call on a walk. Between sessions, you can text or email me, and I’m around for a quick call when something urgent comes up.

My practice is small on purpose: about five people at a time, so everyone gets real attention. Most clients stay on past the first three to six months, but not everyone needs to. We’ll check in periodically and decide together when you’re done.

A few clients, in their own words


Ben

If you’ve read this far and you’re interested in coaching, I’d like to hear from you. I read every email, and will get back to you within 2-3 business days.