I dove deep into the weeds on how I thought about external coaches and the tremendous value I gained over the course of my three coaching relationships beginning in 2013.
I also noted that executive coaches, or “grey hair that can’t fire you”, became a tremendous asset not just for me but also for some other execs on our team.
After that conversation, I wanted to formally crystalize my thoughts on finding and getting the most out of the external executive coaching relationship. I am asked about this topic a fair amount and have a bulleted email that became the basis for this post. I hope any leader, regardless of their stage in the start-up to grown-up lifecycle, will find value in my experiences.
I’ve always been amazed at how quickly a person, including myself, can level up their thinking with access to an experienced ear who’s trusted enough to hear the darkest secrets or biggest concerns. Most times those things are just not meant to be shared with spouses, board members, co-founders or friends. Those people have a vested interest in your company or personal success and they will end up being affected by the stress you are sharing or worse feeling the need to somehow act on the new information.
It’s also important to note that working with a coach is a different dynamic than informal advisory or mentoring relationships. I have been lucky to have many experienced friends and mentors in my life who offered me invaluable time, advice and friendship over the years. I could always rely on them to be there for me. They still are, as I am for them. But while I certainly consider my friends part of my personal advisory board of life, I would never want to risk a friendship by implementing a somewhat rigid and transactional structure around our interactions. Why risk removing the joy from the relationship? It’s the same reason I would not want to bring a close friend into a formal board role as a fiduciary and vice versa. Those relationships are not meant to be transactional.
My decision to find and formalize an executive coaching relationship arose from the following needs as I attempted to scale the business and myself as a first-timer.
I wanted to pay someone to:
- Professionally focus on me via a defined scope of time and responsiveness
- Be part of my regular weekly cadence (usually 1-hour call or Skype) as well as on-call via phone or email
- Take a deep dive on my materials and company when needed
- Come meet with my team in person or via Skype if needed
- Actively listen to the worst of it and help me problem-solve or find clarity
- Always give me their unvarnished opinion, even when it hurt
- Receive assigned to-dos from me
- Be accountable to me for delivering their agreed-upon scope of work
If you were questioning before why I did not want to have one of my friends in this role, I hope it’s become more clear. You undoubtedly bond with people who care enough to offer tough love, but there is always a high risk that once the nature of the relationship changes to work, you can’t go back. Again, it’s the same risk as hiring friends or family in other instances.
Inputs and Outputs
Amalgamated over my experiences with the three coaches, here is what I learned about what a great coach offers and should feel like:
- Has direct personal experience in things you want to learn (technical, leadership, management, etc.)
- Earns your trust quickly
- Is a excellent and active listener
- Asks great questions and mines for root causes
- Listens dramatically more than talks
- Plays a great devil’s advocate
- Encourages you to do things, but does not demand things or create more work for you
- Forces you to crystalize your thinking
- Enjoys talking to you
- Should be selective in who they work with and really qualify you as much as you qualify them
- Genuinely cares about you, your life and work
- Feels like someone you’d probably still keep in touch with even when your formal (paid) relationship is over
- Are well connected and will connect you with other like-minded leaders they know
- Will inevitably run out of playbook, stories, experience to share
The last bullet is notable because in each instance it led me to scale back my communication frequency from weekly to ad hoc with the individual. I found myself leaning out when I felt like the regular time I had scheduled could be better spent on other productive tasks or avenues for learning. In hindsight, this was my indicator to look for the next coach and playbook that I wanted to bolt onto my skillset and add to my support structure.
My first coach and I connected in 2013 when I was trying to figure out what it meant to be CEO of a company in fast growth mode. I continued to utilize coaches through the end of my operational tenure with some breaks in between. Here is the rundown:
Coach 1 – 18-month duration – I tapped him for CEO coaching, CEO playbook evolution and absorbed it voraciously as he had decades of chief exec experience. He was super-smart and had seen a ton of life. He was not local and we have only met in person once or twice. He also helped my co-founders and I negotiate with a potential strategic acquirer that we ended up turning down 2013 (and again in 2015). I was a first-time CEO and wanted to learn by “renting his experience” (His words. He had so many great one liners).
We don’t talk that much now, post working together, but I still have a strong respect for what he brought to the table. I found him by reaching out to him via his blog after reading him and following him for some time. I first became aware of him regularly participating in the comments section of a VC blog I follow. As a former successful multi-time CEO, he is coaching for the joy of sharing and in my opinion, living vicariously through current operators (which we all do post ops). Coaching was not his full time focus. He was not expensive for what I received. Considering the business was paying him, it was basically free compared to nearly any other investment which was adding any real or immediate value for my senior team. We sunset our formal cadence when I felt I needed to address other parts of my playbook, mainly marketing.
Coach 2 – 14-month duration – I found him primarily for a CMO coach/ exec coach as I was feeling better about my evolving framework and approach to CEO. I wanted a seasoned Marketing Exec to help with team, process, strategy. I also wanted someone to help me understand all I didn’t know about brand, marketing and customers. I am a self-taught marketer and I wanted fundamentals and more expansive brand / marketing thought to build taller and faster on an already solid brand foundation. I also wanted another experienced confidant to talk me off the ledge here and there. I pinged my network and was introduced to him by an acquaintance who had worked with him at one time.
He is an amazing human, former CMO, and new to coaching as he had recently left a CMO gig and had some time to kill. We originally spoke informally via Skype and he knew I was looking for help, but he was non-committal post intro from our mutual friend. We both clicked and after a few Skypes he offered to spend time with me weekly, not knowing when he would be going back to a full-time role. Our formal coaching and weekly calls ended when he took his first CEO role. We had become good friends and I ultimately brought him on our collective company board post Comoto deal. He helped us tremendously and spent time with others on my team. His cost structure was dictated by him and was real for him as an individual but insignificant in comparison to other people related company costs.
Coach 3 – 18-month duration – He was a CEO / exec coach for me pre and post RevZilla / Cyclegear / Comoto rollup in 2016. Certainly a great exec coach, but our relationship was less operationally focused than coach 1 or 2. He was a more sounding board, devils advocate and shrink. A chief executive debugger if you will. He helped me most during my difficult decision-making process to leave day-to-day operations in 2017. I sourced him through my network of operators and VCs via an email denoting I was looking for a new backstop.
He found me in “war time” when the things I needed were more specialized, relating to M&A, deal and private equity dynamics. I had leveled up a ton from “CEO 101” I’d done with my first coach years earlier, but I do believe Coach 3 would have been an excellent resource if I’d still needed that playbook. He was a great listener and sounding board. He is a former CFO and professional CEO coaching is his primary business. It was a higher cost investment for the company relative to my other two coaches, but he only had a few clients and the stakes for the seat I sat in were even higher at the point we connected. Still a relatively low investment for the company compared to other salary and related expenses. Our formal relationship ended when I moved on from operations.
Putting It All Together
In sourcing my coaches, I used my network, shamelessly contacted people who I thought I could learn from via wherever I could find them and set a low level of formal expectation initially to try to open a dialog and draw them in. Be scrappy, be up front, show commitment and be humble. You’d be surprised how many people out there may be open to helping. Remember, in most cases, helping someone else solve a real problem makes both people feel great.
Since 2013, I have found it invaluable to have regular access to a person who had no vested interest other than seeing me happy and helping me improve – no strings attached. That is a powerful thing. These people played an important part in my success, as well as the success of the company.
Reflecting on all of it, my keys to success of the coaching relationship are as follows:
- Their experience has to be credible, deep and relevant to your stage of personal and company development
- The interactions need to be regular enough (weekly?) so that they really know you and know what’s going on at your company
- You need to be able to trust them
- It’s about improving your decision making, not about them making decisions for you
- You need to remove your ego so you can tell them what is really keeping you up at night, sometimes embarrassing yourself in the process. It’s uncomfortable. Get over it.
- You have to really want to improve yourself; don’t waste your time or money if you think you are done learning
Also, don’t hesitate to help your people find their own support outside the office and pay for it if you can afford to. If they can get better without increasing your managerial time overhead, that is an obvious win. What are the extra hours of your time coaching them worth, compared to paying their coach’s monthly rate? To be clear I’m not recommending you fully offload your managerial duty, just augment it.
I would encourage any founder, CEO or executive to “find some grey hair who can’t fire you” (another magical coach 1 ‘ism), commit to the process and marvel in your ability to accelerate your efficacy and sleep better at night.