by Jenny Blake
One-Off Mentor Outreach
1. Make three wish lists of people you admire: These are people with whom you want to develop deeper relationships. Consider:
Strongest Ties: People you already know; connection is already warm; the person is likely to be responsive and willing to help.
50/50: People you know loosely or through one or two degrees of separation; you could be introduced through your network; the person might respond to an e-mail or call request.
Long Shots: People you do not know, and with whom direct connection would be difficult; “big fish” who, if they said yes, you would be ridiculously excited to speak with. To quote Dumb and Dumber, “So you’re sayin’ there’s a chance!”
2. E-mail three people from the lists above: Ask if you can speak with them for twenty minutes, or even send one short question via e-mail to start. Mention why you admire them, and why their specific advice would be helpful for you. The key here is making it easy for recipients to say yes.
3. Be curious: On your call or in your e-mail, ask open-ended questions, and let the other person do most of the talking. Ask what they would advise you to do in your situation, what they would have done differently if they could do things over, what the drivers were to their success. You can ask if there are any key resources that were particularly helpful, and if there is anyone else you should speak with.
4. Respect the time parameters you set: Do not go past your scheduled time. This will make them much more likely to be willing to set up a second meeting in the future.
5. Thank you, Part 1: Send a note describing what specific advice resonated, and the impact the conversation had on you.
6. Thank you, Part 2: Do something with their advice! Take action. Report back with a progress update on specific steps you took as a result of your talk.
Board of Advisors
As one-off mentoring relationships progress, you will develop deeper relationships with a handful of people that you can consult regularly and exchange ideas and feedback with, ideally to benefit them as well. In doing so, they can become members of your board of advisors. This is your brain trust, your mentor clan, your strategic “been there, done that” crew who offers lessons from their triumphs and missteps (both of which are invaluable sources of road-tested wisdom).
Although I have been fortunate to have several advisory board members proactively offer to support a particular pursuit, their participation usually came after I initiated the relationships by reaching out to introduce myself. I also make a point to place equal effort on my own reputation-building activities, so that when I do approach people, they will hopefully find me interesting to speak with as well.
You might assemble an informal board of advisors that you consult with questions without explicitly inviting them to be part of your team. Or you can do as Rebecca Rapple did with me and send a formal invitation. After I agreed to be on her personal advisory board, Rebecca sent a spiral-bound packet of her goals for the year in every area—a twenty-page life and business plan.
Sometimes your advisory board members will know each other and interact with each other, but most often they will not. That is okay; your board does not have to convene all at once. Still, they are a short list of five trusted people that you can turn to for advice when you get stuck.
Similarly, you may not have direct relationships with each of your advisory board members. You can still follow their progress, learn by observing what they are up to, and look to them as an inspiring part of your vision. Think of people you admire: perhaps you have no contact with them, but their actions and career approaches still serve as guiding lights. For example, many people swear by “the Church of Oprah,” whose talk show reached ten million daily viewers at its peak. These advisory board members from afar can be inspirational and aspirational, as you learn from their path by staying current on what they are doing. Just remember to also keep your eyes on your own paper and not get too caught up in others’ definitions of, or pathways to, success.
Drafting
If you have seen the Tour de France, you know about drafting: riders clumping behind the lead bike, not passing on purpose, so they can benefit from reduced headwind and effort. They are mimicking a technique used by many bird species. The lead biker or bird is doing the hardest work, while the others flock closely behind to reduce their drag and the energy needed to achieve the same speed.
Career drafting can be a mutually beneficial technique, though it should not devolve into stalking, stealing, plagiarizing, or leeching. Think of someone further along in their career, either in your industry or the one you may want to be in, who is doing what you are hoping to achieve, and ask if you can help with any overflow he or she does not have the time or desire to tackle.
This is not about being lazy. By drafting behind someone who has already cleared a way forward, you can learn from their approach and benefit from overflow they cannot handle. You will pay it forward someday by helping others draft behind you.
I was in a lead position when coaching other solopreneurs, people running their own one-person businesses. As I shifted toward working with executives and entrepreneurs, I referred anyone who reached out for postgrad coaching to several of my clients whose primary goal was working with young professionals. It was rewarding to pass these opportunities along to other coaches who were thrilled to have the work.
On the flip side, I drafted behind other professionals when I was building my speaking business. I told other speakers in my career niche that I loved working with organizations and speaking at conferences, and was happy to travel to do so. Several speakers were glad to refer me for gigs that did not appeal to them, or that they did not have time to take on, particularly those with small children at home.
The people you want to surround yourself with will endorse the adage that “a rising tide lifts all boats.” Andrew Deffley, from Chapter 4, drafted behind an actor who had ten years more experience by forming a genuine friendship with him. They kept in touch after crossing paths on various sets, and when the veteran actor landed a gig on a new web TV series, he recommended Andrew for one of the supporting roles. Based on this introduction and the strength of his audition, Andrew got the job.
Drafting can take several forms:
Apprenticeship: Working for potentially little compensation in exchange for total access and mentoring about how the lead runs their business or career.
Overflow: When the lead has incoming work demand that they cannot fulfill, if you are skilled in your trade but not yet generating the same flow of incoming interest, the lead can recommend you in their place.
Books and podcasts: You do not have to know experts “in real life” to learn from and draft behind them. Books represent years of knowledge, research, and mistakes that you don’t have to make. The first thing I do when someone hands me a book is crack it open, stick my face in it, and inhale its new book smell. Ahhh, the glory of all that wisdom in one condensed package! The author poured years of his or her life experience and expertise into one guide, all for the cost of a few lattes. You can also draft by listening to TED Talks and podcasts, especially if you are an audio learner or want to experience another dimension of an expert’s work.
Friendtors
You have heard the adage that you are the average of the five people you spend the most time with. I say the more the merrier; but at a minimum, if you do not have friends that inspire you and help you expand, it is time to add new ones. There is no room for toxic people ever, but certainly not when you are making a major change. Pivots have a way of forcing these relationships to the surface so they can be dissolved or reconfigured with clearer boundaries.
Friendtors, on the other hand, are the amazing people we are fortunate to call friends, who can also wear the mentor hat professionally by providing domain-specific advice. You may have friendtors in your local area already; if not, start seeking like-minde
d people in online communities or meetup groups focused on your interest areas. Your closest friendtors may also be part of your board of advisors who you turn to when facing big decisions.
One of the most helpful actions that pulled me out of unproductive navel-gazing during a business pivot was setting up phone calls, coffee dates, and walk-and-talks with peers in my industry who had figured out solutions to major sticking points I was facing. Because we were developing mutually beneficial friendships, we met more regularly than we would have had the chance to with more formal “big fish” mentors.
These friendtor conversations provided many benefits: they got me out of the house and my own head, helped me connect with others, gave me real-time feedback and solutions to my specific issues, and uncovered new opportunities and ideas that I would not get from merely reading books and listening to podcasts.
I did not approach these conversations as “can I pick your brain” sessions—that phrase is a personal pet peeve—who wants their brain picked?! Instead, I saw these meetings as an opportunity to provide mutual value. I set an intention to enter those interactions with positivity, feedback, helpful suggestions, resources, encouragement, and connections for the other person, too.
Connecting with friendtors can become a habit just like working out, without feeling like a nausea-inducing form of networking. Set a goal to meet with one or two interesting peers every week. Make reaching out a regular part of your routine, whether forming new connections or revisiting with people you have met in the past. If you do not live in the same city to meet with a friendtor in person, it works just as well to set up a “calfee.” Yes, that is an amalgam of call and coffee—hat tip to my brother for that one!
Another way I catch up with friendtors is by organizing gatherings, events I refer to as “catchalls” because they allow me to catch up with many friendtors at once, and create value by introducing them to each other. Every summer I host Potluck Picnics in Prospect Park, and I encourage invitees to bring others. This allows us to casually connect with old friends and make new ones, all over low-key conversation and delicious food.
Luke Schrotberger turned to his friendtors when he wanted to pivot within his company, where he had worked for nearly ten years, from consulting on projects for defense manufacturing to a group that worked on oil and gas in Alaska. He started by reaching out to close friends inside and outside the company. Luke spoke with one friend who started around the same time he did and was now in a leadership role in Alaska and could provide honest insight and perspective. It was this conversation that ultimately helped him land the job and pivot internally.
Two years later Luke decided he wanted to pivot once again, this time to start his own company, since it seemed there were no more growth opportunities for him with his current employer. Two weeks after he announced to his boss that he was leaving, that same colleague who brought him to Alaska during his last transition made an offer for him to move to Australia to start a new division. Luke’s friendtor outreach provided critical insights during his first pivot, and a job offer at the next.
Mastermind Groups
In addition to casual friendtor relationships, I have also found great value in more formalized peer mastermind groups. For many years now, I have set recurring weekly or biweekly calls with one or two friends who are doing similar work or who share similar goals. These mastermind groups provide consistent accountability, encouragement, and brainstorm buddies.
I recommend finding people who are at your level, with whom you can have an even exchange of ideas, feedback, experiences, and introductions to others. Even if you are not in the same industry or do not share the same goals, these groups can provide a great source of accountability and support if you set those as the central aim.
I met Lora Koenig when she signed up for one of my courses, a ten-week program for generating momentum for a big goal. In that course, I assigned each person to a small mastermind group for weekly accountability check-ins. When Lora joined the program, she was in debt, unhappy with her job, longing to see the world, and wishing she “could just escape from life and start fresh.” Lora said, “I felt restless and miserable, that if something didn’t happen soon, I would be stuck in an unhappy life forever.”
That hopeless feeling made the trouble of change worth it, and sparked her to take three Scan steps at once: apply for the Peace Corps, sign up for a conference for creative types, and enroll in my course. Within six months of completing the course, Lora was accepted into the Peace Corps and pivoted from working in product management to agricultural development in rural Ethiopia.
“The peers I met really helped support me during this time, especially when I felt like I was crazy,” Lora said. “While people I knew at my job and in my city would say they didn’t understand why I wanted a change, my online peers were saying, ‘It’s okay to feel like this,’ and ‘It’s your life.’” For Lora and so many others I have worked with, finding a group of like-minded people online helped her feel less alone, less crazy, and more courageous.
My friend Adam and I hold a 30/30/30 call for 90 minutes, approximately every three weeks: one-third for catch-up, one-third for brainstorming for his business, and one-third for brainstorming on mine. Whenever my friend Elisa and I need extra motivation and accountability during busy times, we start an e-mail thread for the month, then reply at the end of each day with a list of work completed and what we plan to tackle the following day.
When my friend Alexis Grant and I were writing books at the same time, we set up a shared daily writing tracker. It was motivating to see each other’s entries and cheer each other on. A few months later we created a similar spreadsheet and invited people to join us for a challenge of writing 50,000 words in one month during the popular National Novel Writing Month held every November. We named ours NaNoBlogMo to fit our blogging aim, and nearly a hundred people joined. Aided by the power of group accountability, we wrote a combined 556,000 words, with four people hitting the 50,000-word target.
Knowing that my peers would see a goose egg if I didn’t write motivated me to get a little bit done each day. It was the first time in my life, and eight years of blogging, that I had written consistently every day, even when I did not feel “struck with inspiration,” something I had often waited for in the past.
A few things to keep in mind when setting up a mastermind group:
Choose one or two other people whose skills and goals complement each other.
Set up a recurring day and time for your calls. I prefer forty-five minutes every other week, though some mastermind groups do ninety minutes or more.
Start each call by each doing a check-in: talk about a high, low, and something you learned since you last spoke. And share any big wins to help celebrate each other’s successes!
Take turns with a focused brainstorm: succinctly describe one challenge each person is facing, minimizing backstory, and brainstorm with the group for ten to fifteen minutes. Rotate as time allows.
When closing, have each person identify one or two next steps to take before the next call.
On a monthly or quarterly basis, set higher-level goals and reflect on the previous period.
Bartering
If you are short on cash, or even if not, and you have a unique skill to trade for another expert’s services, bartering can be a way to get professional help while keeping expenses down. In a study of a thousand freelancers, 83 percent said they refer work to fellow freelancers, 52 percent team up on projects, and 37 percent trade services by bartering. Bartering agreements work best when there is a start and end date, and clear deliverables on both sides.
I have bartered successfully by trading my business strategy coaching with other coaches, a lawyer, a massage therapist, and a website designer. I even created a website in exchange for having a fee to a yoga retreat in Italy waived. All my barter buddies are good friends to this day, partly because we have bee
n able to come through in the clutch for each other by exchanging expertise over many years, and throughout many ebbs and flows in our lives and businesses.
Bartering works best when you can benefit from a skill the other has and vice versa. This can be tricky; it is not always easy to find two people whose skills directly match up with each other, at the time when both are looking for help, and also have the time, energy, and financial flexibility to take on unpaid work.
Keep in mind that you want to identify a fair exchange rate; given that money will not be changing hands, it is important to determine what would satisfy both sides. Things can get weird (and fast) if the exchange starts to tip unevenly in one direction, or even if one person starts to feel like it does. For this reason, consider whether bartering really is best.
If you are building a business, you might want to pay someone neutral—someone you do not have a personal relationship with—so that you do not feel reserved when giving feedback or bumping up against inevitable creative disagreements. Barters should not be confused with actual business partnerships, which require greater commitment and do involve money or equity.
CAREER KARMA: SEEK RECIPROCAL SUCCESS
On several occasions, I have had potential clients approach me a bit hesitantly since they wanted to do work similar to mine. Would I still be willing to work with them if we are technically competing for the same type of client? “I don’t worry about that for a second,” I reply, often to their surprise. I am delighted to send them referrals, even to people who could just as easily work with me, because I fundamentally believe there is enough for all of us.