Making the Most of Mentorship

Article by:
Kent Lewis EO Portland
Kent Lewis
EO Portland

As a long-time digital marketer and agency owner, I’ve advised a variety of startups over the years. In that time, I’ve witnessed and participated in countless mentorships, and have noticed some themes regarding their efficacy along the way. Recently, a mentor- ship experience within my own company taught me some valuable lessons regarding the importance of coaching.

Awhile ago, I had the opportunity to mentor my second-in- command and help her transition into her new role as CEO. My goal was to step back from the day-to-day operations of the business and pursue other opportunities … but I had to first make sure that she was up to the task. It was soon clear that our mentoring relationship wasn’t working, and I had to fire her. In that short time, I learned a great deal about what it takes to be effectively mentored. Here are four strategies to get the most from your business mentors:

  • Listen at All Costs: In business, it can be difficult listening to input, even if it does come from seasoned business advisors. To move the ball forward, you must be open-minded to new ideas and sufficiently thick-skinned so as not to take any negative feedback personally. In the case of my former CEO, she had difficulty listening to my advice and was eager to demonstrate she could do things on her own. As a result, our annual off-site event and five-year strategic plan were avoidable debacles that eroded her credibility with the team right out of the gate.

  • Always Ask for Help: A significant challenge experienced by a variety of mentees, as well as my CEO, is the ability to ask for help. In my work with incubator companies, I have found that most of the startups lacked the willingness or ability to ask for help, resources or introductions to strategic partners. My CEO was no different, yet she was well aware of what I could offer. Nine times out of 10, a mentor will have a useful answer to any request, and if they don’t, it may be worth re-evaluating whether or not that individual is a good fit as mentor.

  • Communication is King: I’ve found it extremely difficult to advise an entrepreneur if they’re not keeping me in the loop regarding the state of their business. I can’t advise on what I don’t know. In mentoring relationships, mastering the proper velocity and relevance of timely communications regarding key business changes or updates is important. That includes properly framing issues, opportunities or questions, as well as justifying critical decisions. The primary reason I let my CEO go wasn’t because of her poor performance in the new role, it was the discovery that she was withholding key information from me, which critically compromised trust and impacted the health of the company.

  • Act on Input: Taking action on specific input, advice or decisions is essential to earning trust from a mentor. In working with other startups, a common mistake I regularly experienced was the founder not making key decisions or taking timely action. In business, when you learn to embrace change, you begin to create opportunity. In the case of my CEO, I believe it was fear of failure that kept her from making key decisions, and the few actions she did take were safe and not strategic or helpful to the organization.

Coaching can bring with it a lot of challenges and opportunities. Based on my experience mentoring leaders, I realize that I have a long way to go before becoming a truly effective mentor. However, I know that these four steps will help me get there.

Kent Lewis (pictured) is the president and founder of Anvil Media, Inc., a marketing consultancy specializing in search engine and social media marketing. Fun fact: Since 1999, Kent has co-founded two agencies and two non-profits. He can also recite all 50 U.S. states alphabetically in less than 30 seconds.

14,000+ Members

198 Chapters

61 Countries

Stay Connected

Fill out the contact information below to receive EO's newsletter.



    Conditions of EO Membership Application and Renewal:
    Every member who applies or renews their membership agrees to comply with the Policies and Procedures, Bylaws and Code of Conduct of Entrepreneurs' Organization. Current members must complete the online renewal form acknowledging review of the organization's Policies and Procedures, Bylaws and Code of Conduct.