The Online Coaching Guide

Just like dating, there is no right or wrong way to find your coach. The best way to know is to try it out yourself. Most coaches offer a complimentary/discounted first session to get you started.


What Is NOT Coaching?

While coaching makes your life better, it is important to clarify the expectations by understanding that coaching is different from consulting, mentoring, or therapy.

  • Consulting: someone uses expertise and analysis to tell you what to do
  • Mentoring: someone shares their experience so that you can learn from it
  • Therapy: a licensed professional treats you as a patient to normal functioning

What Is Coaching?

To me, coaching is a creative partnership that helps you build awareness, accelerate career growth, and carry out lasting life changes. If you don’t find that with your coach, it’s time to find someone else.


How to find your coach?

With that caveat, let’s talk about how you can find the coach that fits your needs.

  1. Know what you want: Are you looking for professional help or therapy? Make sure that you do some research to understand what coaching really is.
  2. Know your budget: What’s your budget? Elite exec coaches charge $2,500-$10,000+ while career coaches charge $700-$1000 for monthly engagements.
  3. Take the test drive seriously: You don’t have to share everything about your life in the first session because you’ll get plenty of time to do so if that’s the right match. Instead, come with the toughest problem you are facing at the moment, get concrete questions/feedback, and validate them immediately. IMO, this is the most effective way to see if this coach works and maximize your investment.
  4. Trust your intuition: In the first session, you want to see if you could trust and get comfortable with the coach. Just like dating, this is ultimately how you decide whether you are going to invest in the relationship.

A Real Conversation With My Coach

“Charlie, ask me a really hard question.”

I threw my coach a curveball after four coaching sessions.

After all, we have worked through how to let go of a team member, deliver hard feedback, influence senior leaderships, and polishing my performance review. Plus, great coach asks great questions. I couldn’t be more excited.

Which is why I was on the edge of my seat beaming to take the hard question, as a preparation for an open-floor Q&A I’m going to do soon. Now I’m about to share a snippet of what we talked about in the coaching session.

“Charlene, you are balancing so much. You have LivingOS and a challenging job, managing difficult stakeholders, at Google. You’ve just started. Just curious, how much experience do you really have doing both of these jobs?”

That’s the question.

In that question alone, he mentioned the thing I cared the most about, the day job I spent a non-trivial period time on, the key challenge I was managing that day, and the balancing question I often got asked.

Before you read on to my reply, I want you to take a moment and think of your own answer.

Here’s what I said…

“How to balance a challenging full time job and a passionate hustle?

Prioritization. Being really clear about my priorities, how much time I spend on each of them, and how I could use one to fuel the other one as I switch over.”

How is your answer different from mine?


Before I jump on to analyze the structure behind my response, Charlie gave me another question:

“Do you feel like you have been able to give the right attention and coaching to your people in LivingOS, considering that they are also trying to find their way and you are also trying to find your way?”

Another question I love.

Again, before you peek at my answer, take a moment to come up with your own response.

Here’s what I said…

“How to optimize my coaching for LivingOS?

Empathy. I’ve been there. I’m still in the process, so I know how exactly they feel. I know the struggle and how I could offer a framework that works.”

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