COACHING FAQs

Question 1

What’s unique/special/different about your coaching?

Answer

I had a pretty intense startup career up to EVP level, mostly in the engineering/product side of the house. That experience gives me a high degree of pattern-matching with my clients. When you come to a session with something on your mind, there's a strong likelyhood I've been through it personally. I’ve been interested in how people grow and change since coming to California over thirty years ago. I integrate learning from cognitive therapy, yoga, meditation, surfing (patience, persistence!), and improv (be fearless!) into my work. Our sessions can bounce between the specifics of (say) a hiring process, to a visualization backed with some challenging questions and back to a set of experience about hiring challenges at different company stages. I like to keep it light, whilst challenging as directly as I can. My personality is one of humor overlaying a deep seriousness of purpose.

Question 2

What’s your goal in coaching me?

Answer

Change and learning! Learning and change! I want you to be different (and hopefully, very different), in a good way, after we’ve finished working together. I want you to be able to fully handle your current job, and be excited and ready to scale to the next level and beyond. That means you have built new practical skills based on new patterns of belief and behavior.

Question 3

What’s your coaching style/philosophy?

Answer

People are endlessly fascinating, wild, creative, strange and beautiful. Leadership is an intense way of getting closer to what it means to be fully human. The journey should be adventurous, fun, and exciting as well as hard work. I believe people are fundamentally driven by personal patterns of behavior and belief, most of which are either invisible, or barely visible, to us. By making the patterns visible, we can become skillful in managing them, and then add new ones which drive new, better, behavior. I believe we change through insight - seeing the patterns that are driving us currently - and practice - repeatedly trying new behavior to build new skills and eventually new, more healthy and useful foundational patterns. To that end, I will constantly challenge you to find the personal patterns underlying behavior you wish to change, and to practice new behaviors outside your comfort zone.

Question 4

Is this therapy?

Answer

No. It crosses over into that territory, but I’m not looking to “cure you” of a mental disorder! I am deeply interested in your personal patterns, and some of those may trace back directly to your family background, so we may go there. But I am more interested in giving you tools to work with your current patterns and develop new, healthier ones, than digging into your past. I want to look forward with you, not back.

Question 5

What does success look like?

Answer

You’re different! You are confident, open and engaged with your job in areas that were problematic for you, and you’re looking forward to growing fast into the next one. If those things are true, we've done good work together.

Question 6

What happens in the sessions?

Answer

I am guided in the sessions by what is in front of you. We may start where we left off in the previous session and check in with your practice/homework, or we may begin somewhere else entirely. During the session I am intensely focussed on digging below the surface of what is confronting you, so that we can begin the process of real change. To that end, I will ask you questions, propose reflections, try visualizations, offer stories from my experience which may illuminate your current state and challenge you to find your own answers. You will change when you are operating out of your comfort zone. My job is to get you there (safely!), and support you as you learn what needs to be learned. Our goal is to make some serious progress every time we meet.

Question 7

What would an engagement structure look like?

Answer

Typically, I engage with my clients fox six to eight months (we shoot for six, but often end up taking a little longer). We start by generating a goals document - this can take anywhere from two to four sessions. In parallel, I do a 360, talking to roughly ten people who the client recommends. We then review the 360, merging any findings into the goals document and finalizing what we are shooting for in the engagement. If required, we review the goals document with stake-holders: manager, HRBP or VP People, Board members, to ensure alignment and accountability. Then we’re off and running for five to six months, using the goals document to adjust our direction, and completing with a final review with stake-holders. This engagement structure is a template, not a rule-book. There is plenty of room for longer, shorter, more or less intense engagements.

Question 8

Do you extend engagements?

Answer

I do find, particularly in organizations that are growing very quickly, that it’s often helpful to extend the engagement for an additional six months or longer: by the time we've finished the initial engagement, the organization has grown to a new state, and my client has new challenges to deal with.

Question 9

What is the cadence for sessions?

Answer

I find the right balance to be every two weeks. This gives you, the client, enough time to absorb the previous session and practice (important!) the tools we introduced before coming back for more. If things get intense, we can meet more frequently, and I am available for email and quick chats between sessions. I don’t like leaving sessions for a month or longer, but it happens. If it happens frequently, we'll need to adjust.

Question 10

How long is a session and is it in person or remote?

Answer

I work in person, at your office, in San Francisco, and occasionally Silicon Valley. About twenty percent of my clients at any given time are remote or partially remote (Seattle, India) - video works well. Our sessions can be anywhere from 45 to 90 minutes. Some clients get value from the longer sessions, some prefer the compressed time of 45 minutes.

Question 11

Do I have to do the homework?

Answer

Well, yes, practice is fundamental. If you do it, there’s a strong likelihood you’ll make some fundamental changes pretty quickly. If you don’t, well, less so. Sometimes the homework means trying something new in every meeting. Sometimes it’s a simple reflection. The more intensely you practice, the greater the likelihood of real change.