Career Coaching: How an Outside Perspective Can Change Your Life

Learn about yourself and address your blind spots

In 2011, I was struggling with the feeling that my career had stalled. My skip-level manager, Dan Rose, set up time with me to talk about it. Dan candidly shared his observations from having worked with me for a couple of years, highlighting how it could be difficult to connect and build trust with me. He suggested that I find ways to be more relatable while being less assertive and fixed in my point of view. I know many women reading this may think Dan was being unfair, and I have given this a lot of thought over the years. I’m not sure if he would have said the same things to a man in my position. However, that didn’t necessarily make his observations, stemming from his real-life experiences with me, any less true. 

As we discussed these challenges, Dan shared his personal journey struggling with unrelatability. He explained how he had grown beyond this with the help of a career coach. Then he offered to hire me a coach to help me work through some of these issues. I admit I was skeptical. While he was a mentor, our relationship was already strained, as evidenced by the feedback he shared. A few days later, Dan let me know he had personally selected a coach whom he believed would help me grow beyond my current setbacks. I thanked him, but I remained unsure what this meant. 

A Note on Coaching 

Having the right coach can change the trajectory of your career. Depending on the company, your access to coaching may vary. Hiring a personal coach is often out of reach in most people’s budgets, but it is a worthwhile investment if you are facing a major decision or need to work through a particularly tough issue. Here is a list of different types of coaching and how each can help you: 

• Individual coaching: Individual career and leadership coaching is a benefit that certain companies provide for high performers and executives. These services are fairly expensive, so most companies have rules around who can use them. Private coaches unaffiliated with work may be a better route if you need a sounding board. 

• Career development classes: Many companies have leadership development training available. By taking advantage of these classes, you can learn many of the strategies you need to unblock yourself. Some classes even have a small number of sessions with a coach to help you apply the techniques. 

• Team coaching: Many larger companies set aside budgets for offsite team-building. If you are planning an offsite, consider hiring a coaching firm. They can teach you how to work better together by identifying your style and work preferences. They also can help you work through team challenges. Some do individual sessions as pre-work or post-work for the offsite. 

• Peer coaching: Many leaders have office hours or time set aside for coaching. I do quick coaching sessions (15 to 30 mins) with two or three people a week on specific topics of their choice. While these are more ephemeral, they can help you spot and address a problem quickly. Additionally, in groups like Women in Product, you can seek out those with experience to help you through a specific situation or dilemma. 

• Coaching circles: We greatly underestimate the power of coaching circles. I have previously been part of two Lean In circles and recently joined one for senior executives. I found them to be safe places to talk about work obstacles without judgment. Often a peer circle can give you a different perspective or share an insight you missed because you are too close to the problem. I treasure the friendships I have made through these circles, and they also offer a way to expand your network as you explore new opportunities. 

Finding the Right Coach 

When I met Katia Verresen for the first time, she surprised me. I had always imagined a career coach to be all business, focused on specific goals and techniques. Instead, we talked about feelings much more than aspirations, about blockers more than goals. She was warm, inviting, and kind, and she was all heart. Because I am all head, I thought that what I wanted was a logical and systematic approach. However, because we were so different, Katia was able to challenge my ways of thinking. One thing she said during our first meeting stuck with me: “My job is to help you get out of your own way.”  She even added in one of our early meetings, “You will be CEO one day.” I laughed since I was not even a Director at Facebook at the time, but she saw something in me that I didn’t see in myself. That was when I knew she would be perfect.  

I have met with many coaches over the years. Many of my peers and reports did 360s with coaches, and I also worked with some for training and events. Each coach is different in their approach and style. Finding the right coach means taking the time to figure out what you need. You must determine whether this person can help you unlock and unblock yourself from the challenges you face. One coach I met was all checklists and no-nonsense advice on how to fix things. I met with her several times, and if you had asked me back then, I would have selected someone like her to be my coach. Later, I remember another manager, after hearing that Katia was my coach, saying, “I am surprised. She is so different from you in every way.” 

I laughed. It was true, but that was why it worked so well.

What Great Coaching Looks Like 

I had never worked with a coach before Katia, so I didn’t know what to expect when we started working together. Katia and I met a couple of times, and she suggested that I read a few books, including Power: Why Some People Have It—and Others Don't and Stress-Free for Good.    

At first, it felt a bit foreign to rehash the highs and lows of my week with someone who was virtually a stranger. We talked about what was working and what wasn’t, and how to think about and approach the issues should I encounter them again. Each time, she put me at ease as I shared, but she also pointed out ways I could have thought about the problem differently or reacted in a way to achieve my goals more directly. It took some time to adjust to having someone think through things that previously seemed unremarkable, but Katia's insights helped me see how some of my actions were self-defeating, and how my perception was skewed by my experiences. 

Within a month of our first meeting, I was considering leaving Facebook for a role at a startup. I was incredibly unhappy and frustrated in my role, and I had stumbled upon an external position that sounded intriguing. Just two days before I had to give my decision to the startup founder, I found out that I was pregnant with a surprise third child. I remember being anxious and seeking Katia’s advice on what I should do, given that she had been hired by Facebook. 

That was when she said, “I am hired by your company, but I'm here to make you successful because when you are successful they thrive.” We discussed my options, and she replied, “You are destined for great things, based on how you are describing your opportunities do they align with that trajectory?” She made me realize that the opportunity was not the right one at that time, and I turned it down.

Over the next few months, Katia helped me through a stressful and difficult pregnancy, including symphysis pubis dysfunction, a pelvic condition that took an incredible toll on me. Every time I took a step, the pain was so intense that it was hindering my ability to think straight. At the same time, my father was diagnosed with Stage IV cancer and had only months remaining. I could barely make it through the day, much less think about my career. Katia helped me through that challenging time in my life, and we’ve worked together off and on for a decade.  

Katia has taught me many things, most of all about myself. She has challenged me, pushed me, and encouraged me to be more than I could have ever imagined. The question she asked me every week in different ways was, “What is it inside of you that’s keeping you from doing what you know you should be doing?” 

Katia forced me outside of my comfort zone and made me confront my blockers. Without her support, I would never have achieved so much of what I have in my career. When the idea first came up to host the Women in Product conference, I was reluctant when I told her about the idea that a group of random women talked about on a whim, but she pushed me to start it. Today Women in Product is an organization of over 27,000 members. When I hesitated to write my book, Katia encouraged me to pick a deadline and submit the proposal. The book will be out next September. When I wondered if I was ready to be a CEO, she reminded me of what she told me when we first met.

What Coaching Offers 

A great coach is someone who can help you in a variety of ways. They serve as a mirror to help you see your actions and how they affect others. They are a sounding board for you to discuss ideas and dilemmas. They create a space to ask questions, work through problems, and open up.  

As you look for a coach, remember that all great coaches offer three essential things:

• Tools to think through problems in different ways

• Perspective on your blockers and how to work through them 

• Encouragement to think bigger and aspire to more

I once set someone on my team up to work with Katia for a few sessions. He later joked, “Having a career coach is like having a work therapist.” 

I laughed, but in some ways, I agree. The power of coaching is in having a neutral third party hear your point of view and then push you to look at the world differently. That is what makes it worth the investment.

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Katia provided a place for me to question myself and others. She gave me tough love when I hesitated to do something that I needed to do. She identified when I was headed for burnout and encouraged me to recharge before I got overwhelmed. She helped me determine when it was time to leave a job I loved in order to reach my next stage of career growth.  

Coaching is an investment in yourself and in your future. Because of the expense, coaching within companies is often limited to senior executives, high performers, or short-term change management. However, some companies and alumni organizations offer access to coaches or coaching circles. Even if your employer does not offer it, consider finding and working with a coach on your own. Even a short-term engagement can be transformative when you have the right person guiding you. 

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Recommended Coaches 

Note that many of these coaches work with C-Suite executives and senior leadership teams, but some also speak at development events.

• Katia Verresen 

• Sanyin Siang 

• Thuy Sindell  

• Carol Isozaki 

• Chris Treadwell  

• Prakash Raman