Find a Brutally Honest Friend In Your Life and Ask Them This One Question!



An unusual way to get feedback might be the secret to unlocking your entrepreneurial dreams.

Typical Tuesday morning.  Scanning emails before my morning workout, checking to make sure the world has survived without my online presence. Suddenly a subject line grabs my attention. IF YOU PROMISE TO TELL ME WHAT I SUCK AT I WILL BUY YOU A FREE CUP OF COFFEE!  All caps and with a playful smiley face emoji in the header – I clicked on the link to see the details of this highly unusual invitation. The email was from a very close professional contact – I will call her Lynn Jenkins – and I knew there had to be an interesting explanation.

The body of the email was pretty straight forward and increased my curiosity. Lynn wanted to meet up for a cup of coffee to get some feedback.  I was honored and agreed to the meeting, looking forward to understanding more about what she was trying to achieve. I have known Lynn for over a decade, and she is one of the most qualified and accomplished entrepreneurs in my network. She runs a very successful business, has raised a tremendous amount of capital and seems to be scaling to heights that most entrepreneurs only dream about. This context made her request even more intriguing.  

A week later I walked into a sleepy coffee shop to meet Lynn and looked forward to telling her all the things she sucked at…given her accomplishments, I expected the conversation to be pretty short.

The conversation was lively, and I gave Lynn some generic observations about areas that she could get better at but frankly I held back a bit.  Who wants to tell a friend what they really suck at?  But to Lynn’s credit, she pushed me hard and wouldn’t let me get away with platitudes about “work life balance” or “empowering her team to do more”.  So, after a few Café Americano’s and her encouragement, I finally provided her with very specific, painful and direct feedback on areas that I simply did not think she was very good at professionally.  

She took the feedback, leaned her chair back and after a moment of awkward silence simply said, “Thank you. Your candid feedback means so much to me and has helped me more than you can imagine. Thank you”. We parted ways amicably but secretly I was fearful that our professional relationship might be officially over.

A week later I dialed Lynn’s number, hoping that she still would speak to me after our one-way feedback session. She picked up quickly and her tone and energy indicated she didn’t hate me and I breathed a sigh of relief. I was increasingly curious about what she was doing with the feedback, focused exclusively on her shortcomings, that she was collecting. Lynn explained it simply.

“My professional coach and I are working on areas of professional development, both for me and for my team.  We did the 360-degree reviews, and they were helpful, but the picture wasn’t complete.  By asking people I know and trust, like you, what they see as my  biggest shortcomings we have developed a two-part strategy”.  Lynn then continued, “First, we have a specific list of things I can get better at as a leader.  Second, we are looking at my team and see if we have the right skills set to compensate for skills that I don’t have or want to have.  We call it the Suck Strategy!”

Simply brilliant.  

Asking close connections why you suck might be the fastest way to get real self-awareness about your skills and weaknesses. A survey of 75 members of the Stanford Graduate School of Business Advisory Council rated self-awareness as the most important capability for leaders to develop. Most entrepreneurs skip over self-awareness – who has the time? – and this ends up being a real shortcoming as they start to scale their businesses.

This strategy also forces you to take a hard look in the mirror and focus on your weaknesses in all their glory.  We all have them. I see so many new entrepreneurs think they need to “fake it until they make it” and part of this “faking” is to ignore shortcomings. Acting like a superhero is not only dangerous but overlooks a real opportunity for both personal and team developments.  

Looking back at my experience as an entrepreneur, my personal skills were pretty clear. I was good at sales, positioning and communication. These skills helped at winning new customers, raising capital and recruiting strong team members. But I was never good at delegation, and I hated process management – both are very important to scaling a business.  Fortunately, I had a coach who did a version of the “tell me why I suck” and I got a lot of feedback (the list was longer than I care to acknowledge). The shortcomings that I noted early were starting to take a toll on both the company and my team. So the question quickly became what to do with this feedback?  

After much consideration, my coach and I concluded that effective delegation is an imperative skill for any CEO that wants to scale a business and would be the primary area of self-development. Think of this as skill attainment or enhancement.  It became a big focus for me, and while I never mastered it, I did get better over time.  But we also concluded that process management was a skill that I never was going to obtain – so we needed to hire someone ASAP to fill this gap. Call this “outsourcing” or “supplementing”.  It was a game changer for the business.

There is an old adage that it is much easier to play to your strengths instead of trying to improve on your weaknesses. I agree with this but would add Lynn’s “what to I suck at” test as a balance to this assertion. It provides a clear roadmap for your own skill development and provides amazing insights into what skills you need to add to your team. What other question could yield such powerful and actionable insights?

It takes thick skin and an open mind, but I would strongly suggest any entrepreneur give a try.  Maybe ease into it and start with a close friend first.  The key is to ask several people who know you personally and professionally this short but painful question. “What do I really suck at?”  

Meditate first, bring an open mind and a notebook and see what you can find out about yourself.  And pay for the coffee! Who knows, this simple question just might be the key to scaling your business and getting one step closer to your entrepreneurial dream. 

Grab your copy of Mr. Monkey and Me here or see if you have what it takes to be an entrepreneur by taking The Entrepreneur Survival Test.

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