9 Tactical Pages From My Playbook: How to Make New IRL Friends, Get (And Keep) a Mentor, Write to 100+ People, Dream 2x Bigger & more

I’ve recently been sharing a number of pages from my playbook with others — life hacks that have helped me meet some of the best people in my life, to push and stretch myself in writing and speaking, and bonus: saved time. Here are my top 9 playbook pages and a bonus below — I’d love to hear yours.

How to Meet New People

1. +1 Brunch

When I hit 30, I realized I wasn’t making new friends. And even (especially) in a big city like New York City, it’s hard to forge new friendships.

So I launched a +1 Brunch, where I invited 3 women whom I already knew (through work, through other circles) and asked them each to invite 1 new person to bring to brunch on Saturday. And it was so awesome.

Conversation flows easily when you have other smart people around the table, and when you have other like-minded women who also are looking for the same thing — meaningful connections and networks.

From here: The best win: I made a wonderful new IRL close friend! And she has further helped expand my network and introduced me to other wonderful people.

2. Breakfast Club

As a VC, I am so lucky I get to meet many amazing people as a part of my job. But I’ve personally found it really hard to maintain those relationships after the 1st meeting. I also simply cannot drink that much coffee for 1:1 meetings, and I was finding those great one-time introductions simply were not getting nurtured.

So I started a Breakfast Club — similar to my +1 Brunch — where I essentially keep a running list of awesome women I meet and set a recurring Breakfast Club calendar invite at the same easy location at The Coffee Shop in Union Square on the first Friday morning of every month.

Friday mornings are generally a bit more relaxed. It’s low key — if you can make the breakfast, great. If not — no worries, we’ll catch you at the next one. We generally have 4–6 smart women from different parts of tech and NYC community show up and the conversation really just flows.

And most important lesson and reminder of all — my biggest value is getting this great group of people together and for them to meet one another, rather than 1:1 with me.

Even if you’re not in tech, there are great people for you to convene and bring together.

From here: at our last Breakfast Club, one of the women shared a professional challenge she was facing, and all the other women chimed in with their own experiences, suggestions, and feedback. It was such a powerful conversation, a soul-fulfilling way to kick off a Friday morning, and the start to many future connects.

3. Email 3 New People, Every Week

Thank you Angela Lee of 37 Angels for this!

Reach out (cold) to 3 new people, every week.

This may not sound that hard, but at least for me, it’s a muscle that I do still need to develop: to not only identify net new people I want to meet, but to track down their contact info, and most importantly, set time to send a thoughtful email.

This kind of outbound outreach will help you stretch and grow and drive your network with new (and strategic) relationships — whether it is people in your industry, people you admire, or people you want to get to know.

The key is to be thoughtful about your “ask” — and generally always coupling it with you offering some insights or support too.

Protip: even if they don’t respond the first time, set a Boomerang to ping them one more time. I’ve responded to so many people who (kindly) sent me a reminder follow-up email.

From here: I’ve been so wonderfully surprised who has responded to my cold outreach emails — VCs, founders, and also reaching out to conferences and events I want to attend. It really, really never hurts to ask.

How to Get and Keep a Mentor

4. Borrow a Mentor

In so many of the panels and talks I speak at, women want to talk about finding mentors. And I get it. It’s hard — and it’s been found that women have to work harder to build this mentor network.

My best hack? Asking other awesome women friends of mine who their mentor is. Chances are, this person is already an amazing, generous person who is committed to helping a young person. If they are willing — see if they would be open to including you in their next session.

From here: A friend of mine so generously introduced me to her mentor. The 3 of us — 1 mentor and 2 mentees — would get breakfast together, and all 3 of us would learn so much from one another in our amped-up conversations. It has been a far more efficient breakfast for everyone’s busy schedules, and quite honestly, our discussions have been multipliers in terms of even better ideas and feedback and value-add to all three of us, than if it had only been 1:1.

5. Keeping Up With Your Mentor

Life happens, fast, for both you and your mentor. Set up a recurring calendar invite with mentor. Make it quarterly. You’ll realize the date is here before you know it. The calendar is meant to serve as more of a reminder ping — as chances are you’ll still have to set up and schedule a time to meet (or use a great tool like x.ai to help!). But this way, it won’t be a whole year before you realize you haven’t seen each other.

From here: I’ve gone to some of my best, most important lunches with mentors, thanks to my recurring calendar invite saves.

How to Establish Thought Leadership

6. Write Your Heart Out (And Dial a Friend).

Seriously. Do as I say and not as I do, because I clearly need to write more too. But as Hunter Walk best puts it — write!

This is my best piece of advice — if you are trying to get into VC, if you are trying to recruit for your team, if you’re trying to switch jobs, put your voice out there. Other like-minded people will find you.

Even on things you don’t feel qualified to write about…!

Protip: Start small — the pieces don’t have to be long or research-driven. And 80% done and shipped is better than 0% perfect.

And dial a friend. I’ve been so fortune to have an amazing team at Work-Bench, who can not only help me carry me 75% of a draft but help me knock it out of the park for that last 50%. If you’re lucky to surround yourselves with magical wordsmiths and grammar aficionados like Allie Felix and Kelley Elizabeth Henry…then lean on them!

From here: I’ve started writing more and more on my Medium — pieces that felt easier to write to ones that required more time and effort. Still more to come.

7. Set Up a Newsletter

This was the most phenomenal piece of advice from Anne Libby, my incredible coach. Set up a newsletter! Even if it is only to 20 people, that will help you grow your voice and network, help stay in touch, and bring others to you (and help me tremendously in exercising my writing muscle).

I started with a small group of 20 or so friends who I would email 1x a month, and share some of the things I was thinking about or working through (from being a manger to sales to running).

I then moved it over to Tiny Letter, an easy and lightweight platform to send out emails. Most of all — in a voice very different from my Medium — I write how I would write to friends: casually, no capitalization, and as if I am sitting next to them at brunch. Make it easy.

From here: I’ve stayed in touch with 100+ people whom I otherwise would not, and who then write back to me with their own life updates, comments, and feedback. I’ve so cherished these emails and conversations.

How to Speak Better

8. Know That Some of the Best Speakers Work with Coaches…So You Can Too.

Growing up, I was painfully shy. And even now, despite people seeing my extroverted nature…I still struggle with pubic speaking.

I’ve written a bit on the topic of speaking here before:

But 3 years ago, before I was to speak on a panel at a conference, I tracked down a speaking coach to work with, and Michael Balaoing has changed my life and perspective on public speaking.

For me, the biggest lesson has been that it’s not only about the story — but how you tell the story.

From here: I recently brought Michael with me to work on our recent Navigate 2018: Women in Enterprise Tech Summit, who really helped bring our already boss speakers to new heights, across content, story-telling, and delivery.

9. Videotape Yourself Speaking

I am such a fast talker. That plus the natural adrenaline I get from public speaking, I know I go way too fast (even if I sound normal in my head!).

Until you videotape yourself, you miss out on hearing opportunities to inject strategic pauses, volume differentiation, and tone inflection.

Videotape yourself! Do it!!! It sucks, it’s painful, but you’ll be glad you did.

From here: I’m still a work-in-progress :) But once you do videotape…that’s when you can really track progress…

Bonus 10. 2x Your Goals

From our recent VC panel at our Navigate 2018 Summit, I shared the following playbook page:

For founders — this means taking your pitch deck and 2x everything — your market, your product, your targets. Just see how some of these outsized goals feel. You may be surprised that some of these goals are actually far more reachable and achievable than you may have thought…

I’d love to hear from you! What are tactical pages from your playbook? We’ve got some terrific playbooks from our recent #Navigate18 Summit, and are collating even more at Work-Bench and with our Women in Enterprise series, so be sure to follow us.

If even one of these tips helped you, a handclap from you would help share it with others — thank you!



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Jessica Lin

Jessica Lin

co-founder & VC @Work_Bench | GED educator | rethinking work