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Why We All Need a Friendly Wise Skeptic

When I was in the eleventh grade, I decided that I was going to make a movie. This was way back in the day, prior to YouTube sensations and the rise of Instagram. I spent three days in my parent’s basement writing a 150-page screenplay (which I was sure was going to be a box office best seller); I then posted an add on Kijiji for volunteer actors, held auditions at my parent’s house, and spent my summer using an old camcorder (pre iPhone days were rough). It was really apparent to everyone, with the exception being my teenage self, that I had no idea what I was doing.

One day, after a particularly grueling experience learning about city permits (another story for another time), my mom sat me down. She told me that she and my stepdad had someone they wanted me to meet, someone who made films for a living and would probably be able to help guide me on this journey (I think they were both secretly praying that this was a phase).

This was how I got connected with my first friendly wise skeptic (FWS), a producer from a local media company. She talked me through the ins and outs of the process, as well as flagged potential challenges and hazards for me. After meeting with her several times, I decided to shut down filming – as I felt like I needed to learn more about what I was doing first. She generously continued to talk me through challenges and ideas throughout the following school year, and created space for me to intern with her the following summer.

There is a quote I love that goes something like this: “not having a mentor can only be compared to sailing solo, without experience and without a compass” (Alexander R. Margulis).

You can even take this one step further when thinking of a friendly wise skeptic. An FWS can be a mentor, but they might not always be. At The Trico Charitable Foundation (TCF), we describe the FWS as the crucial role of an “outside expert” – someone who has specific, constructive feedback; knows the industry you are working in, and is willing to voice red flags, see around your blind spots, and challenge your key assumptions. These experts act as a friendly yet candid teacher, bringing in industry specific knowledge to the table, and caring about your success. A friendly wise skeptic is someone who will question your assumptions – via their skepticism, and offer insights on how you might test or prove your assumptions.

Entrepreneurs and Social Entrepreneurs alike rely on complex mental models in decision making – a network of positive and negative associations between words, experiences, and teachings informing the body of knowledge we carry about any given topic. Our mental models change or are reinforced based on what, how, and when we learn.

As such, it can often be difficult to catch our own faulty mental models (manifested through biases and assumptions); “it is particularly difficult early in the learning process, when your mental representations are still tentative and inaccurate [to catch your own mistakes]; once you have developed a foundation of solid representations, you work from those to build new and more effective representations on your own” (Ericsson & Pool 148).

Having someone in your corner who can see where you want to go, the things that might be holding you back, and the challenges that have yet to come is so key in developing effective mental models and progressing you on your learning journey. As noted in the book Peak: How All of Us can Achieve Extraordinary things, “much of what a good teacher or coach will do is develop (…) exercises for you, designed specifically to help you improve the particular skills you are focused on at the moment” (Ericsson & Pool 157).

Having a friendly wise skeptic is like being coached by someone who has already walked the path ahead.
To a certain level, you can embody practices of mindfulness and do your own research to mitigate the impacts of your own biases, assumptions, and blind spots. However, no matter how hard you try, “you are still going to miss or misunderstand some subtleties – and sometimes some things that are not so subtle – and you are not going to be able to figure out the best ways to fix all of your weaknesses, even if you do spot them” (Ericsson & Pool 158). By teaching you how to anticipate the challenges, questions, and points of tension specific to your industry and venture, your friendly wise skeptic is helping you craft your own mental representations which will allow you to monitor yourself (Ericsson & Pool 150). It is important to note that friendly wise skeptics are neither too kind, nor too scary. They strike a balance between being questioning but still encouraging – that is where the magic happens.

At TCF, we believe in the power of owning your own journey. As a key mindset for social entrepreneurs, we believe that you should “always do what you think is right and assume sole responsibility for that. (…) Keep ownership of your journey by asking, “what could I do differently to change these results?” When working with a friendly wise skeptic, or any other form of mentorship/coaching etc, it is always important to know why you are doing what you are doing – not taking steps blindly based on someone else’s advice about your company. At the end of the day, you are the expert on your business.

So, how do you find a friendly wise skeptic, you may ask?

As always, we encourage starting with your why. What is your ultimate goal? What do you need to know in order to achieve that goal? Who is someone that has walked the same or a similar path? These are all useful questions to help you identify potential candidates. Other questions might be: who has mentored/taught or coached before; who has a communication style I can work with; and who do I respect the most in this space?

In this digital age, your friendly wise skeptics might not even need to be in your geographic area. You could find them on Instagram, LinkedIn, or other forms of social media. By starting with your why, you’re identifying the key thing that is driving your learning – and we would encourage you to think bigger than your direct ecosystem or next door neighbors.

For more from Ericsson & Pool check out Peak

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