The Master, The Mentor, and The Best Mate

If you’ve spent any time in corporate America, then you’ve probably heard about 360 Feedback. It’s basically a way for middle management to get feedback from “all around,” including from their superiors, fellow managers, and direct reports. When you’re starting your own venture, however, you don’t have the luxury (or the frustration) of having multiple bosses, colleagues, and subordinates to tell you how you’re doing. Yet collecting this type of feedback is critical to improving two vital signs of the successful entrepreneur: diagnosing your current performance and planning a path to achieve your future goals. Without the ability to do these two things effectively, entrepreneurs can feel lost, confused, or like they’re just blindly guessing, no matter how much they keep up the bravado of having everything in hand.

So what’s the solution? Enter: 360 Learning.

Rather than rely on others to give us feedback, as entrepreneurs, we can use our strength at seeking out information from the sources all around us. No matter what stage of entrepreneurship we’re at, there’s always someone further along, someone who’s facing the same challenges, and someone who’s a few steps behind us. These fellow entrepreneurs are the people best suited to teach us what we need to know to succeed. They are literally “all around” us, working hard, ready to inspire our efforts and our growth as entrepreneurs. But harnessing these people requires understanding on how to optimize their roles in our lives.

Step 1: Find a Master

The Master is an obvious choice. Every entrepreneur has an idol- the person (or people) we look up to and aspire to be like. Some of us keep quotes from them on our white boards or desktops. Others read book after book trying to understand how Steve Jobs, Warren Buffet, or Andrew Carnegie built their empires. Unfortunately, these are not the masters we learn from best. Too often, these expert entrepreneurs have been entrepreneurs for too long to fully remember what it was like to be launching their first ventures. They’ve been blinded by their own success. And the people that write about them often talk about the actions they took rather than the skills, behaviors, and thought processes that led them to those actions in the first place. Don’t get me wrong, these are fantastic people to look up to and be inspired by. But when you’re facing an important decision, like how to determine the lifetime value of your prospective customers or whether you are reaching the right market with the right message, Richard Branson is not going to step in and give you custom tailored advice (and if he is, then you probably don’t need to read the rest of this post).

Instead of reaching for the stars, research in the learning sciences tells us that we need to find someone who is just a few steps ahead of us. We need to watch them keenly and learn from their behaviors, procedures, and approaches to building a business.[ii] So rather than asking yourself, “What would Bill Gates do?,” why not find a really good local entrepreneur and ask them? Pick someone who has recently dealt with: creating a terms of service agreement, raising a round of funding, bootstrapping their way to cash flow positive, or some other challenge that is closest to the task you’re currently working on. Better yet, find a few entrepreneurs. Having multiple masters to observe and learn from is even better than having just one.[iii] If you can, pick entrepreneurs in a similar domain (but not competitors) and cultivate friendships with them. Encourage them as well by reminding them that being a mentor is as valuable to one’s growth as having one.

Take Action: Make a list of all the challenges you are facing or will be facing over the next six months. Be as specific and as thorough as you can be.

Good Example: I need a software developer who knows how to handle Python, and who can convince me of why he’s worth both cash up front and equity.

Bad Example: I need to know how to hire a good tech guy.

Go to entrepreneurship meetups like Technori Pitch or Chicago Lean Startup. Find an entrepreneur (or two, or three) who seems like he or she has tackled similar challenges. Approach that person and say, “I’m currently facing (or about to face) challenge x, have you faced that challenge? How did you handle it? What did you learn?” If what they say makes sense to you, try it out. If it works, send them an email following up and telling them how their advice helped you succeed in overcoming your challenge. If they acknowledge and appreciate your gratitude, then you’ve got yourself a master. Buy that person a beer or offer to take him/her to a Cubs game. Then, repay the good karma and…

Step 2: Become a Mentor

A Mentor is someone who knows a bit more, has more experience, and demonstrates greater wisdom than his or her protégé. In teaching, advising, or otherwise explaining the way things work, mentors also get the opportunity to reflect on what they know, diagnose their own mistakes, solidify their best strategies and remind themselves of why they’re doing what their doing in the first place.[iv] Mentors can also draw on the enthusiasm of their protégés and channel that into their own business efforts, often finding new areas of growth for themselves by working with someone who’s eager to grow. If you want to cultivate your own learning, become a mentor. It doesn’t matter what stage of the game you’re in. There is always someone a few steps back who could really benefit from your knowledge and experience, and you can benefit from the process of having to consolidate what you’ve learned and deliver it intelligibly.

If you’re an entrepreneur in Chicago, you’ve got it made. Not only are there thousands of entrepreneurs (and would-be entrepreneurs) in and around the city, the existing culture also seems to be perfectly suited for the “pay it forward” person in all of us. Blogging is great for casting a wide net, but having one or two local entrepreneurs who look to you for inspiration and wisdom can drive you onward even when you feel like packing it in.

Take Action: Offer to be a judge or mentor at a local Startup Weekend. Hold “office hours” on Twitter or at a co-working space. Attend Bootstrapper’s Breakfast and invite questions. Or, sign up to be an entrepreneurship mentor at Code Academy. Then make sure you’re covered for the times when things just aren’t working and you need a friend by doing the following…

Step 3: Confer With Your Best Mate

The Best Mate is the man or woman that will struggle with you side by side through the entrepreneurial victories and setbacks. You don’t necessarily have to work on the same business. In fact it’s better if you’ve each got your own ventures. But the point of having a Best Mate is to have someone to talk with over drinks where the flow of advice is less directed and the conversations can be more informal. This creates a fertile learning space where creativity, inspiration, ingenuity, and camaraderie help both of you generate inspired solutions.

Have you ever been stuck on a problem or unsure of a decision, only to have a friend who, within a few minutes of listening to your dilemma, says just the right thing? Have you ever taken a break from your worries and helped a friend work through his or her own, only to come back to yours with renewed confidence and vigor? Sometimes, outside ears can hear better than those that are caught up in the cacophony of the day’s meetings. Sometimes a friend’s eyes can see into the shadows you’re unconsciously turning away from. Your Best Mate is your study buddy for a life-long course in entrepreneurship. Meet with this person regularly and devote time to talking shop, not just blowing off steam.

Take Action: If you’re working out of home or a coffee shop, stop it. If you have an office in the middle of nowhere, pack it up. Instead, try one of the more friendly and collaborative co-working spaces in and around the city- 1871, Catapult, and CoLab Evanston are all great ones. Or, you can try Desktime to find one that suits your needs. Meetups are great for networking, but daily or weekly contact is what helps build a solid professional friendship.

Optimize Your Learning

We are social creatures, and we learn through social interactions. The modern city accelerated technological growth because it brought people and their industries closer together. Online communication accelerates our societal learning curve even more. But, individuals still learn best by: watching, emulating, innovating, and reflecting. So optimize your learning (and your growth as an entrepreneur) by reading only what you’re going to discuss with your Best Mate. Take a workshop or go to a meetup not to exchange business cards, but with the intention of forming a genuine connection with a master to observe or a protégé to mentor. Cultivate a practice of learning from the people all around you. Then maybe one day, your quotes will find themselves on the white boards of striving entrepreneurs, and entrepreneurship as an evolving practice will have come a full 360.