The bell struck one-o’clock. I pressed my shirt down nervously, checked my reflection in the mirror, put on some fresh chapstick. The portal window opened, and the women poured into the room. Souls from all over the world. And there I was, leading a brand-new group of people who didn’t know each other, on a topic that would scare the pants off of most h…

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Life can knock the wind out of you.

And when it does, things like basic words and the concept of time fly out the window. People ask what you want or need, and you stare back at them, bewildered by how they’re still standing upright. Didn’t the world just collapse?

Knowing what to say and how to hold space for people can sometimes feel impossible. It mi…

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She’d been trying for years to get pregnant. I’d known since the earliest days that she was trying to start a family. “Why isn’t this working?” she asked. For her, it felt like defeat. She was bewildered and sad.

“Why is getting pregnant so much harder than I expected?”

This is such a tough place to be—to want some…

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“I didn’t prioritize [who I was working] with high enough on my list,” Jessica Wan shared with me when reflecting on her career. You need to find the people within your organization that will help shape you, she explained. Great mentors and leaders that are invested in helping you grow can make all the difference. If you’re at a big brand name but you’re disposable, are you gaining the network that you need?

The relationship aspect of job growth is often overlooked, but it’s essential for your career growth, and this executive says it’s better to start thinking about this earlier in your career than you might realize.

Jessica Wan is a senior executive who has led marketing teams and product launches at Apple, Smule, Magoosh, and the San Francisco Opera for the last 18 years. She’s the host of the Ampersand Manifesto Podcast, and an executive coach for mid-to-senior level professionals with big jobs, big lives, and big dreams. Her specialty is working with leaders who are navigating change in their careers and lives, whether it’s pivoting career paths, scaling a business through new stages of growth, or expanding confidence in people management and leadership.

She’s based in Berkeley, CA, where she lives with her husband and 6-year-old son. She’s been a two-time member of The Wise Women’s Council I asked her to talk to us about parenting and business, and to give us insight in how to connect with people throughout your career. Below, she shares her five tips on how to get almost anyone to have a virtual coffee with you.

Here’s our interview.

What time did you wake up this morning and what was the first thing you did?

I woke up around 5:45am this morning, mostly because I conked out at 9pm the night before! I did some light stretching and then went downstairs to get some cuddle time with the dog.

Who are all the people on your support team who help you, both visible and invisible?

There are so many. My husband, my dad, my in-laws, our former nanny-turned-babysitter, my child's teachers and all the staff at his school, summer camp providers, all the workers involved in how we feed our family. I'll stop there but I'm sure there are so many more folks!

How many actual work hours do you have to do your work in any given week? (Give us your best estimate).

Somewhere between 30-35, depending on the week.

If you could go back and give yourself any advice about parenting, what would it be?

It's okay to not be perfect because there's no way you can be perfect. As a parent, you're going to make mistakes all the time, and that's normal. Don't dwell over whether your spirited child's behavior is nature or nurture. Does it really matter? Focus on how best to support them and take care of yourself and your marriage.

Ask for help, and say yes when help is offered!

“Ask for help, and say yes when help is offered!”

How has parenting changed you? How has business changed you?

Parenting has allowed me to enjoy all the kid things again with a new perspective. We don't really remember the first time around! I also have a newfound appreciation for parents and children that I didn't have before having my own child. The deep connection my son and I have with each other is so unique and special. It's something I cherish every day.

How long have you been building your business and what was the origin story or what was the idea?

In one sense, I've been building my business since my first job. And in another sense, it's only been a few months.

The long game: I consider my experiences in the business world over these past 18 years or so to be crucial to what I can provide in terms of understanding and empathy as a coach. I've had a lot of experiences in the working world that can benefit me in my new role.

The launch of the business: When I left my last job as Head of Marketing for a 100-person company, I had no clue what I was going to do next. I took a few months to travel and reconnect with people, and then enjoy the holidays being fully present with my family. It wasn't until January 2022 that I explored several paths—roles within companies, startup ideas, consulting—and finally realized that I was supposed to be a coach all along. It's what I loved to do. Once I realized that, things moved quickly. I started coaching clients pretty much immediately, and on the backend built out the business. I officially launched the business on March 21, 2022.

If you could go back and give yourself any advice about entrepreneurship, leadership, or business, what would it be?

Look for the people first.

It's always mattered who I work with, but earlier on in my life, I didn't prioritize the ‘WHO’ high enough on my list when choosing that next role. It makes sense—the earlier you are in your career, the more you might think that the "big fancy company name" really matters. And it might. But even so, can you find the people within that big company who get you? Can you find the leaders and role models who will shape you?

I've learned a lot from what leaders didn't do or how they shouldn't have acted. Valuable learnings, but it would have been more powerful to have seen those who I'd admire.

Please share a specific area of expertise that is really useful for our audience. What is a skill, tip, or teachable tool that you’d like to share?

How to get almost anyone to have coffee with you:

• Do your research on them, their organization, and what matters to them.

• Clarify your why: what's your purpose or goal?

• Treat them to coffee. If it's a virtual meeting, send a Starbucks gift card.

• Share interesting things about yourself in your message. You never know what they might be looking for or needing in their business.

• Keep your message real, casual, and positive.

Give us 3 tools, parent hacks, or business hacks that have really helped you.

1. For business: Asana. I loooooooove project management and use Asana as my go-to tool. We used it at my last company and it was the "brain" of the organization. Since it's the "brain" I can get things out of my own brain and move along with the rest of my life.

2. Parent hack: Prep dinner during lunch. Do all the chopping, rinsing, etc ahead of time so then the cooking is fast!

3. For business: Compile similar projects into the same chunk of time. For example, this hour is my WWC power hour :) I'm working on this Q&A, doing my WWC 2022 intro in Slack, and checking out Voxer next!

Twice a year, we invite people to join the Wise Women’s Council, our community for women who are parents and also entrepreneurs, leaders, and executives. As I was reflecting on all of the incredible women who join us, I realized I wanted to introduce you to them. These brilliant humans are changing the future of work and parenting. We’re featuring them here. 

We are also doing a feature series on dads. If you know an awesome dad navigating parenting and work that we should feature, nominate dads we should feature here.

I was in an online group the other day—one I’d paid to be a part of, with 75 stunning, high-level people convened all in one room, but no one was speaking up. Everyone there—CEOs, leaders, champions for causes—was a certified ruckus maker, and yet the conversation was completely staid. Nobody was talking, nothing was flowing, and we were all milling around (in that way that happens in virtual rooms).

I could tell that the group was in danger. In the tiny screen windows, I could tell people’s eyes were starting to glaze over, attention flicking back to email (or any other browser), and the video cameras started to turn off. Within another week or two, people would fizzle out and then leave permanently, or become “lurkers,” waiting for someone else to speak up, but never gaining traction.

After being in dozens of communities and studying how to build them, I was pretty sure I could spot the problem. Over the past ten years, I’ve lead communities, online events, offline events, and private brainstorms & retreats, and I’ve studied with Seth Godin, Jenny Sauer Klein, Desiree Adaway, and more about facilitation design.

We—the participants, these 75 high-prestige leaders—didn’t have a clear direction we would head together, and we hadn't been given, or created, any group guidelines. As a result, we didn't feel safe enough to speak up. So the conversation flopped.

When people sign up for group programs or events, they sign up for an idea or a vision. But beyond the vision, the invisible architecture of any group space is the container that people agree to be in together. This “container” is held up by boundaries, even if they’re invisible. These edges are the group guidelines.

What’s a guideline? It’s the rule for playing the game. Soccer isn’t that much fun if you don’t know where the edge of field is, what the goal is, and that you’re not allowed to touch the ball with your hands. Likewise, any group that you convene will need to have strong guidelines for how to act, what to say, what to share, and what’s not allowed.

One of my specialties is creating space for deep conversations specicially—brave, vulnerable, open conversations about topics that are normally taboo. In one of my pop-up sessions, I got the following feedback:

One of the reasons The Wise Women's Council, one of the communities I run, creates space for such deep conversations is because for the first several weeks and months we spend time creating clear ground rules so we know what to expect, what conversations we can have, and how we'll respond to each other when we share our brave and vulnerable truths. Setting ground rules is the work you must do in order to get a great group off the ground.

Lean in closer and I'll tell you a few of my secrets.

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Why group guidelines are the secret sauce for amazing events

"Sarah, I always feel so much better after your Zoom calls. What is it? How do you do it?"

I love hosting zoom calls, retreats, dinner parties, events, you name it. I like people, I've learned to love asking questions, and I want to get deep into connection and storytelling. But great stories and great connections don't just happen.

Have you ever been to an event where immediately your guard is up? Where the net-work-ing smacks of status signaling and awkward engagements? When you want to just leave and Irish Goodbye your way out of the room as fast as you can?

It all comes down to group guidelines. You MUST have group guidelines in order for your event or gathering to go well. This applies to teams, too.

Don't just throw a bunch of people in a room without an agenda, a leader, a facilitation plan, or any guidelines. That's a recipe for a slow, painful, sorry zoom call where people leave feeling slightly more dead inside. Most people know to have a plan and a facilitator, but they forget to have guidelines.

Your guidelines should:

• Tell people what behavior and outcomes are expected and hoped for.

• Clearly articulate the posture, sayings, phrases, or ways-of-being that your group stands for.

• Answer the question "People like us... do things like this," a phrase I've learned time and time again from Seth Godin.

• Clearly articulate what is not acceptable and what behaviors aren't allowed.

• Invite people to show up as their best.

People like to be clued in to what's expected, how to behave, and we want to trust that other people will show up for us the way we show up for them. One of the best ways to do this is through group guidelines.

Ideally, the best guidelines for a group are framed in a positive manner, rather than a list of restrictions. But, when drafting your guidelines, it's very likely your first draft will be a long list of ‘nopes—then it's your job to flip them and create their positive opposites. In effect, you want to call people UP to their best behavior, not create a floor for their worst behavior. Here's an example. Both are appropriate and work well, depending on the group.

• No foul language, shaming, or hate speech allowed.

• We welcome positive language, PG self-control, and supportive language towards your peers. Be kind and generous with each other.

Here's what our guidelines look like inside The Wise Women's Council, and other groups I run.

Okay, I'm going to show you our exact guidelines for the community that we run. Please do not copy-paste these to your own group—it won't work if you do that. You'll need to develop your own guidelines based on who you're with, what your group is for, and what your goals are. I'll walk you through ours as an example.

In The Wise Women's Council, we're focused on having deep, honest, brave conversations with women leaders about the challenges and struggles of being a working parent. People may have been trying to have kids for years, they may be subject to awful peers in the workplace, they may be completely slammed by the pandemic—business and babies ask us to be brave and they can make us quite raw.

Conversations that are judgmental, full of advice, or devoid of active listening can make people feel even more alone, unseen, and frustrated. That is the *opposite* of our goal. We want this space to feel kind, inviting, encouraging, and supportive.

These are our group guidelines:

1. Use the phrase "in my experience."

When folks use global phrases like "we all" or "everybody thinks" or "it's always..." we can risk invalidating other people's experiences when what we're trying to do is share our own. I ask people to use these three words whenever they are talking about their stories and experience so it leaves ample room and space for other people to have similar, different, and varied experiences.

2. Take good care of people, including yourself.

Get water if you need it, use the bathroom, turn your video off if you need a screen break. Speak up when you need something, ask courageously for what you want. If you need to lie down and listen, do that. Take full care of yourself and your body as well as the other people on the call.

3. We strive to give everyone space to feel safe, seen, supported and heard.

We center the people in the hot seat, and focus on them. We use active listening skills. We validate their experiences even if they might be different than ours. Phrases like "Thank you for telling me," and "that must be hard for you," and "what was that like for you?" and "I'm so glad you shared that with us" are all very common in our group.

4. Your story is yours to share—ask permission to share other people's stories.

Folks can get so excited after a call that they want to rush out and tell everyone about what happened (and I get that impulse, it happens to me too!). But people share bravely and vulnerably and it's important to respect their confidentiality. So, we have a rule: if you want to share someone else's story, ask their permission first.

5. Limit blanket advice.

Advice feels good to give—for the giver. It doesn't always feel good for the receiver, especially if they haven't really explored their own thoughts or mind first. Most people, most of the time, need more space and listening before they need advice rushed in on them. Advice is like blankets. One blanket is nice if you're cold, but more than one and it's just a smother of more work you have to do to wade out from under it.

6. Being vulnerable can be hard, but deeply rewarding.

This is our goal—to create a space where people can feel safe to do the hard work of self-examination. To learn where things are getting stuck, and to admit and be honest about our fears or our failings. This is not easy to do. This can be really rough, hard, and challenging. But when we're in the company of supportive people who care, who are kind, and who let us have space to show up imperfectly messy, that's when the magic happens.

If you have group guidelines that have served you or the places you go, I'd love to hear about them. Leave a comment below and tell me what some of your favorite community guidelines are. Who is doing this well? Who should I learn from? How did they help you or others show up at your best?

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