Mentor Madness

Mentors help entrepreneurs without asking for anything in return.

These diamonds in the rough may be hard to find and the vulnerability to ask others for help can feel heavy, but don’t be afraid. Most entrepreneurs and intrapreneurs enjoy helping others. Not everyone is graced with extra time, but there are good mentors in every community. Local mentors provide huge in-person value and the online universe offers infinitely more ways to find good fits. The wider your engaged network is, the more strategic you can be when selecting mentors as well. Even with a wide spectrum of options, take time to consider whom you trust and who will trust you in return. Be respectful of everyone’s time, but don’t be afraid to approach the giants you admire most.

As an entrepreneur talking with potential mentors, be transparent about your situation, concise with storytelling, and clear with specific needs. Spell out your vision, the current state of your business, what makes you a pain reliever vs. a vitamin, and how this mentor’s experience could help you navigate the fog.

As you explore mentor relationships, it’s unlikely one person can support you on all fronts. This means you must get comfortable working with multiple mentors.

The more one mentor can help, the more attention they deserve. When you give a mentor more attention, it should not feel like they need to do the same. Approach each exchange with composure. Make it convenient for people who aren’t required to care. Go out of your way to be effective and efficient. Learn how someone likes to communicate and make detailed emails concise. Answer questions directly and find ways to keep connecting new dots. Think about deliberate deliverables. As things come together, slow play the delivery of assets and things you want to discuss. This will keep progress from feeling too heavy. It also creates space for concentrated feedback on more specific topics. A mentor who helps you in a meaningful way will rarely disappear, so there’s no need to overload them with too much at once. This practice helps you stay on top of ongoing conversations, while also allowing mentors to add more precise value. Optimizing mentor relationships this way will inspires trust, action fueled by accountability, and solidify a lasting sense of accomplishment for everyone interested in your success.

Along with learning from mentors, consider being a mentor yourself! Success (and failure) leaves clues so no matter what you’ve achieved in life, you have wisdom to share.

Extra Shot

Interested in mentorship? Here are characteristics to consider.

If you decide to offer your time in this way, be generous, but also realistic about how you can help. Mentoring can become a nagging task if you’re stretched too thin and the moment you feel resentment, the quality of your support diminishes. To avoid this pitfall, be upfront with the time you’re willing to commit and deliver whatever is promised. When volunteering a significant amount of time, be sure to feel at peace about the impact you’re making.

Your time spent mentoring should feel easy, efficient, and fun, yet challenging and rewarding as well. A #GiveFirst mindset paired with an authentic connection to founders you care about creates space for honest feedback and a magical experience for those who learn, earn, and then give back.

Follow Up

As you continue to show up and stand out, it’s important to wrap a bow on your interactions by following up. Why? When creating connections, a single encounter is rarely enough. Whether it’s an email, phone call, social media connection, or handwritten note, follow up.

These tiny touch points can root a relationship. Even if there’s no obvious ways to collaborate right away, take a moment to say you enjoyed meeting that new contact. If possible, include something memorable from your encounter to personalize the message. This is also another chance to ask if there’s anything you can do to help, then close by sharing how you look forward to staying in touch. Whether they respond or not, this follow-up will increase the chance you’ll be remembered.

Extra Shot

The moment you meet is an effective time to connect on social media.

As you meet more people, it can become hard to maintain this habit without support. Don’t be afraid to use relationship management tools to keep conversations organized. Hubspot, Airtable, and other free CRM tools may be a good place to start. These platforms can automate your communication efforts, but play it cool. This is not the time to sell or bombard someone’s inbox. Instead of a pre-determined cadence, make a simple note to follow up. Use this reminder to comment on a social media post, share a quick idea, suggest a meaningful introduction, or invite your new contact to an upcoming event. While these follow ups are unscripted, it doesn’t hurt to internally track how many times you’ve touched base.

This balanced, friendly, and ongoing effort to stay connected will separate you from the pack and keep you on that person’s radar. Business may not spawn from these touch points, but there will be fresh context the next time you see each other. If opportunities to collaborate emerge, you’ll have a channel of communication already in place. Either way, showing up, standing out, and following up makes it easier to explore engaging ideas with your evolving network.

Stand Out

Being remarkable in a networking environment is not rocket science. Be friendly, vulnerable, funny, curious, and eager to help without getting stuck in one place.

As you continue to show up, you’ll learn from others and also learn more about yourself. You’ll be able to ask great questions and be adaptable to any conversation. You’ll need to share your work less, which will allow you to make more introductions. This will make you stand out as a connector.

Ready to shake things up? Avoid the temptation to ask the most common question at networking events: “So, what do you do?” Instead, consider more interesting ways to get people talking.

– How are you feeling?
– How do you like to spend your time?
– What does a day inside your office involve?
– What mindset inspires your best work?
– What’s a recent project you enjoyed working on?
– Are there any roadblocks you’re working through?
– Is there anything I can help you with right now?
– Would you do this work if money weren’t a factor?
– What did you do before your current role?

You only have a moment to make a good impression. It never hurts to throw in a specific topic to help people remember you. Avoid small talk like the weather. Also, family means everything to most people, but avoid going too far down that rabbit hole. Here are a few creative conversation starters to sprinkle in.

– What are your superpowers?
– Where did you travel to last?
– Have you ever been a mentor or an advisor?
– What are you reading or listening to right now?
– How would you describe the internet to a child?
– If you’re a pro wrestler, what’s your entrance song?
– Is there anything that may surprise me about you?
– What’s an interesting paradox you‘ve answered?
– How do you define success? How about happiness?
– Have you ever regretted not doing something?

When it’s time to move on, there is also an art to exiting a conversation. This is handy when conversations have gone on too long. One tactic is to bring more people into the conversation. Kindly introduce everyone to each other. You then have the option to stick around or excuse yourself. Even if you leave the chat, your energy will remain a part of that new conversation as you mingle elsewhere. If you’re at a networking event, another approach is to joke that it’s time for both of you to go meet more new people. This lighthearted suggestion eliminates any awkwardness.

If you’re the one holding conversations too long, you’ll know it when people try similar exiting tactics on you. To improve your relationship-building skills, stop draining the energy from each interaction. Be cognizant of how long you hold onto each conversation. Abandon the idea that everything must happen in one exchange. Even if it feels abrupt, don’t be afraid to move away from conversations before they feel complete. Ending interactions a bit early leaves room for more conversation next time. This creates a subconscious gap to fill and therefore more reasons to reconnect.

Lone Wolves

A common misconception is that you must have a team to be successful. There is a limit to your own capacity, but it is possible to build rewarding endeavors all by yourself. Solving complex problems may require co-founders and a larger team, but your passionate dedication is all you need to get started.

Lasting energy is required to forge this path, but without the need to answer to anyone, you can stay nimble and be more efficient by eliminating internal delays. To avoid burnout, you must stay mindful of your personal bandwidth. Self-awareness will help you avoid market disconnects, The Headline Trap, and relationship problems as well.

To coordinate new initiatives into your career portfolio, consider how the project connects to your current work. Clear overlaps can be good, but can also cause unwanted tension. A project less related to your existing work actually makes everything easier to shuffle. Even when projects affect different industries, it’s still you making things happen. The option to build into what motivates you in different ways will energize your work on all fronts. Action on one project will provide fresh momentum for others. Learn when to say yes and no, then wisely activate your time on each front.

As a lone wolf, it’s easy to go hard toward your own dream, but know when you need help. The freedom of working alone is within reach, but execution still requires collaboration. The world is full of friends, community allies, and contractors eager to help. Outside assistance may slow you down, but it won’t dilute equity, and it may be the key to a new reality.

Extra Shot

Need someone to bounce ideas off of? Let’s have coffee.

If you venture out alone, prepare for intoxicating highs and crushing loneliness. The consuming nature of building by yourself will incite grit, but don’t let it blind you. It’s easy to build too far into the wrong direction without a team. This is why community and customer discovery are even more important for lone wolves.

Co-Founders

The freedom to build as a lone wolf is exhilarating, but collaboration is how to go beyond your own limitations.

It takes more time to collaborate with others, but finding a co-founder can be life changing. Generosity, transparency, and candidness will bring the right people on board faster. Even if it’s one other person who wants to build in an aligned direction, co-founders pave a smoother path toward success.

Good people eager to collaborate can fall in your lap, but finding co-founders usually requires a concerted effort. If you hunt for the right co-founder in the beginning, it will take more time to make early progress. The trade-off is more creative and cultural alignment when things come together. This makes it easier to evolve ideas when a team finds its groove early on.

If you’ve been building as a lone wolf too long, you may have a harder time working with a co-founder. This is because it’s difficult for others to jump on a bus you’ve been driving the whole time. It’s still possible, but a thoughtful willingness to adapt is required. If you’re merging energy with another lone wolf, take your time. Moving a bit slower will uncover the why behind what was built before the partnership. As trust grows within the team, everyone will have more freedom to make the impact they want.

No matter how you decide to join forces with co-founders, choose wisely. It’s easy to work with someone like you, but don’t clone yourself. As a fun analogy, we also don’t put linebackers at wide receiver, right? Identify what you’re good at and know where you fall short. This allows you to pinpoint people who have complementary skill sets. It will also keep you focused on finding those who can push you further. With indelible honesty, who might be fun to build with?

Extra Shot

Perhaps you are looking for a co-founder? Show up to where the people you may want to work with are congregating. For instance, I met two of my co-founders at 1 Million Cups. We were working on different things, but over time, our shared interests led to a business idea we decided to pursue together.

Like anything new, as a team forms, early excitement will provide a surge of enthusiasm. This will soon fade and at some point, the story of this venture will end. It’s easier to plan ahead than it is to react to problems after they arise. Talk openly about roles and how everyone wants to be involved to avoid future tension. Discussing everyone’s immediate and future commitments reduces the stress of unknowns. With professional transparency a team can also work with more sustained stability. This leads to less drama and more consistent success.

As you solidify complementary co-founders, the goal is to have everyone equally enthusiastic. Think deeply about what a fair equity and role distribution means now and how it can also support future growth. No matter how cap tables look, co-founders expand capabilities and add valuable accountability. Working with others to achieve a shared goal is also more fun than working alone. Collaborate with remarkable co-founders and you’ll enjoy the ride together.

Extra Shot

Want more? Check out the Team chapter in You Don’t Need This Book!