What I Have Learned From Working with a Business Coach (Part 2)

In my last blog post, I told you about how I made the decision to work with a business coach, and how I was introduced to Judi Cohen of Warrior One.  You can read Part 1 here.


In this second installment, I want to tell you about my experiences interviewing other business coaches, the benefits and drawbacks to working with a business coach, and what I’ve accomplished so far with my coach.

As I mentioned in my first post, even though I really liked Judi Cohen right off the bat, I still thought it was important for me to do my due diligence and interview a few other coaches as well.

The experience was kind of like “Goldilocks and the Three Wolves.” Some of the coaches were too soft, others were too hard.

Some of the coaches felt like I was talking to Stuart Smalley … while others clearly took their inspiration from Lt. Col. Bill Kilgore.

Perhaps it’s no surprise that I decided to go with Judi Cohen of Warrior One, as I got the best feeling from talking to her.

The Drawbacks to Working with a Coach

I want to be clear and honest about what it’s like working with a business coach.  Working with a coach is not always going to be a walk in the park. At least it shouldn’t be.

If your coaching experience is 100% pain-free, then something must not be working.

There should be constructive criticism. You should be challenged.

You also need to be open to being critiqued. You need to be willing to make changes. Or else you are just wasting time and money.

Speaking of money: it’s not cheap. And it takes time away from doing the work that brings in money, such as in my case billable work.

But you know what is more expensive than the cost of working with a coach? Spending years and years doing the wrong things. Or serving the wrong clients.   Treading water when you could be building the business you are supposed to be building.

It takes money to make money.

You’ll also have to explain why you are working with a coach to others, including employees, co-business owners or your spouse.

Speaking of that, my wife was very ambivalent at first. That’s putting it nicely. Let’s just say she would probably much rather have the money in our pockets.

Here’s how I addressed her concerns. I made a connection between my work with my coach and our shared family goals.

Before I hired Judi, on Kevin Waldron’s advice, my wife and I sat down and mapped out our shared family goals. I literally took her out to lunch, without our son, for the purpose of mapping out our five-year life and family goals.

At first I think she thought I was nuts. But it turned out to be a great experience, and one I would recommend to others.

We talked about our goals, our dreams and what we wanted as a family in the future.

Some of these long-term family goals we identified included:

  1. Saving up enough money for the down payment to buy a 4 bedroom, 2+ bath home in our town.
  2. Increasing my income so that my wife can work less during the summers (she has an academic schedule and therefore can take much of her summer off, although she has been working during summers in recent years for extra income.)
  3. Saving more money for retirement.
  4. Traveling more frequently.
  5. Spending a greater chunk of our summers living and/or working part time from Lake Tahoe.

Having identified those goals, I can make the connection between my work with a coach and achieving these goals. My work with a coach is specifically aimed at giving our family a better life.  Hard not to like that, right?

My Work with my Coach … So Far

I have only met with Judi a couple of times, but so far the progress has been great. We meet every other Monday afternoon for an hour via Skype or Facetime.

In one of our first meetings, we started off with discussing the types of clients I want to work with, and what type of work I want to do for them. As a result of that discussion, I wrote:

My core focus is entrepreneurs and small business owners who have up to 20 employees, but who want to grow their businesses larger.

After identifying my ideal client/customer, we moved on to mapping out what I want my business to look like 5 years from now. You have to start with that longer-term goal before you can begin creating shorter-term goals, like 3-year, 2-year and 1-year goals.

A few sessions later, we moved on to focusing on what specific topics I would write about here on this blog.

Identifying the topics is important because it’s very easy with a blog to get off-topic and start writing about topics that do not appeal to your core audience.

Here’s what I identified as my core topics so far:


  1. Entrepreneurship
  2. Law
  3. Efficiency
  4. Product Reviews
  5. Reader Challenges
  6. “Personal” Successes & Failures in Entrepreneurship

My challenge going forward is to make sure that everything I put on this blog fits into one of those categories.

(By the way, this blog post fits within a couple of the above categories, including numbers 1, 4 and 6.)

What Did You Learn During Your Twenties?

During our last session, Judi challenged me to share with her what big lessons I learned from my twenties.

Why my twenties? Well, it’s a time of major growth for most people. I bet you have some good lessons from your twenties as well.

During my twenties, I attended and graduated from college, backpacked around 21 countries across Europe, worked as a Writer in the White House and a Speechwriter in the California Governor’s office, then lost my job rather spectacularly thanks to the California Recall election and Arnold Schwarzenegger, and finally capped it all off by quitting my career in politics to go to law school.

I also fell in love and got married. And I lived in a couple of different cities – moving from L.A. to Santa Barbara to Washington D.C. to Sacramento to San Francisco.

When I thought back on everything that had happened to me during those years, the advice just came flowing out.  Here are a few of the lessons I came up with:

  1. Work to Live; Don’t Live to Work
  2. Keep your friends and allies close
  3. Know and embrace your “true supporters” who want to support what you do.
  4. Be comfortable with failure; we all fail. Embrace your failures and the lessons that come from your failures.
  5. Don’t be afraid to take two steps back to take two steps forward.

Judi’s point in discussing all of this was that the value we all have to share is inside of us; sometimes it’s just a question of teasing it all out.

My next challenge is to take these life lessons and the stories that inspired them and turning them into compelling blog posts for you, dear reader. Aren’t you lucky.

So that’s a summary of my experiences so far in working with a coach.  It’s been fun and I look forward to it every other week.

As I continue on, I will give you all updates as I continue this work.

I’m looking forward to continuing this work, and to sharing my ideas and lessons here.

Now how about you – have you ever worked with a coach, or thought about working with a coach? Let us hear about it in the comments below.

Photo credit: Microsoft office online




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