Unconventional Mentorship

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Unconventional Mentorship

A lot of people have a really skewed idea of what it means to be a mentor. 

There’s a picture in our minds that looks something like this: A senior executive taking an earnest young recruit in their first professional suit out to lunch, and prattling on about golf. (Not that there’s anything wrong with golf.) They talk for an hour, a few questions get lobbed about, and everything gets wrapped up in a neat bow.  

While traditional one-on-one mentoring remains important to our personal development, mentoring is also changing.  

More and more, mentoring is layered, varied, and group-oriented. It doesn’t just happen in one single way, either. 

Mentoring can be open-ended. An entrepreneur may need a professional mentor to be a sounding board in order to figure out how they can turn their passions into realistic plans.  

Mentoring can be holistic. Mentors can also help mentees look at how they need to level up their own personal, social, or business skills, or find complementary partnerships. 

Mentoring can be strategic. A great board of directors (always a good source of mentorship) is always looking at how they can support their CEO, founder, or executive team, and how they can provide strategic advice or brainstorming ideas that can lead directly to top-level decision-making and management strategies.

Mentoring can be functional. Often, there is a need to look at how teams function in a range of units, whether departmental or otherwise. Mentors can help a group connect to their goals or one another, almost like a coach with expertise in a functional area such as sales or marketing. 

Mentoring can be temporary. Mentorship chats can take place anywhere, any time, formally or informally, to bring forward thoughts and ideas between two or more professionals. 

No matter what form it takes, there is a world-class standard for mentorship, and it starts with a single understanding: Mentors are not the leaders in the room.

In my opinion, to be a great mentor, the first half of your role is to be a fly on the wall. The second half is to be a provider of strategic insight. Many, if not most, people assume that strategic insight is a mentor’s only role, but that’s a very short-sighted approach. 

Why? When I provide mentorship, I know that it takes a lot of discipline to sit on the sidelines. That’s an incredibly important part of what I do. Teams need to gel and learn together. When do I step in? Only when that’s not quite happening yet. 

I continue to lean back and learn because, in my own businesses, I knew that I needed to understand the inside baseball on every single role, even when the business was really growing and I was incredibly busy. I’d go down to the wash bay and wash some dishes and understand the task so that I could mentor the sanitation team and understand them. Same thing in the warehouse. Same thing on the production floor. I learned that I needed to be conscious of what’s going on from my team members’ point of view. That’s because when every team member knows that you have their back and you understand what their actual day is like, you can make decisions together that make sense for the business, and that make sense for them. 

How does my unconventional mentorship approach work in practice?  

I encourage entrepreneurs to start with having a good governance and meeting plan. Do they meet as a senior leadership team every week? A lot of entrepreneurs actually don't know the answers to these questions because they just show up to work and talk every day. But that’s different than meeting every week and having a structure in place. 

I ask entrepreneurs if they’re mentoring their own teams. Do they meet one-on-one with functional teams every week? Are they observing their work and asking questions? A mentor is in the room to ascertain what questions need to be asked, and what standards need to come into play, whether we are talking about operations, marketing, or finance.

I discover how much listening entrepreneurs are doing versus talking. What are they learning from their industry, their peers, and their team members? A mentor is also present to nudge teams back onto their own plans and activities, plans connected to their own passions and interests.

I explore what may help that team come together tighter, or be a little bit more clear on their planning. I want to get down and dirty from a mentorship perspective, instead of mentoring from the sky, and understand every part of their business. Whether you’re a mentor or a new entrepreneur, you have to walk a mile in the shoes of every team member to build awareness and mutual trust.

Bottom line? Mentorship always works best in both directions. I can provide my best advice when I’ve received the best information.

That only happens as a result of personal connection, communication, and trust.


I hope you enjoyed the read, and are ready to think differently about mentorship.

Until next time.

Let’s Grow!

Here are 4 other ways I can help you grow:

  1. Get my new book GROW: 12 Unconventional Lessons for Becoming an Unstoppable Entrepreneur

  2. Work with me 1:1 to grow your business.

  3. Listen to my Founder to Mentor podcast. (new episodes weekly)

  4. Get my free mentorship growth tools at www.fatafleishman.org.


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