What’s Sidebar?

Sidebar is an online community and professional group coaching program that sets you up with a “personal board of directors.”

When you purchase a Sidebar membership, you’re matched with a group of 6-8 peers, plus a skilled facilitator. You commit to show up for a regularly scheduled group meeting, 90 minutes, twice per month. At each meeting, you either present and receive coaching from your group or you listen and participate in coaching for a peer.

The Sidebar membership includes access to an app that feels like a cross between Slack and Zoom.

Note the Sidebar within Sidebar.

In the Sidebar app, you can chat with your group, drop into topical channels, and set goals to check off. When it’s time for your group session, your group’s channel gets repurposed as the live chat for your video call. The video call interface has structured time blocks to keep folks on task, and every video call wraps up with a survey to assess how much value you got out of your session.

Sidebar also offers additional Speaker Series events and programming for members.

Why I joined Sidebar

When I first heard about Sidebar at the top of an episode of Lenny’s Podcast last summer, I was already thinking about a personal board of directors.

From 2020-2021, I worked with an awesome leadership coach who helped me guide myself through some challenging transitions. Their coaching process was designed to force me to look inward, to find clarity in my own thoughts and experiences.

I had been feeling really stuck in my career progression, and the introspective work didn’t feel like it was helping. I left the coaching experience craving outside advice from people who understood my field. I started thinking about building a bench of people who could tell it to me straight and help me see what I couldn’t.

Sidebar seemed perfectly positioned to fill this gap. They promised highly-vetted professional peer mentors, structured facilitation, accountability, and confidentiality.

What I loved about Sidebar

Diverse, high-caliber, growth-minded

Once the matching process was complete, Sidebar connected me with a group of exceptional professionals.

My small group included a mix of product people, engineers, managers, and entrepreneurs. We had representation from employees across a wide range of industries, everything from well-known consumer brands to FAANG to healthtech and hospitality. Group members dialed in from locations across the U.S. and around the globe: India, France, New York City, San Francisco, Austin, Seattle, and so on.

At every meeting, there were at least three people I could count on to understand my space and the way Product Marketing operates with little explanation. Alongside the validation from peers in my field, I also got to hear fresh perspectives from people in unrelated roles. The feedback was insightful and energizing.

Uplifting facilitation

The Sidebar facilitator is like a professional executive coach who’s embedded in your core group. They set the tone, define the meeting structure, send recaps, enforce attendance, and keep momentum going. Our group’s facilitator was great. They were positive, emotionally intelligent, and consistent. I looked forward to hearing their voice at every meeting.

Celebrating meaningful moments

In the Sidebar app, you can use the integrated Goal setting tool to lock in to-do items that are visible to your core group. When you complete a Goal, a notification with a green checkbox posts to the group channel so everybody can celebrate your progress. We also used our chat or group meetings to share “meaningful moments,” ad hoc.

We celebrated product launches, wine bar openings, new jobs, new hobbies, raises, promotions, engagements, and growing families.

What I learned in Sidebar

How to listen deeply and ask questions

Each Sidebar session requires a generous amount of attention. When somebody has the floor, you have to focus for a sustained period of time to learn about their scenario.

We practiced repeating back what we heard, in summary. We also practiced asking a group round of clarifying questions before jumping in with feedback.

I used a Google Doc to keep notes during every session. I’d jot down themes, feelings, phrases, patterns.

Over the course of the year, I noticed my personal notes became more sparse. I got more confident that I could truly hear and internalize somebody’s situation without writing down every word verbatim. I became more bold, asking the questions I was most curious about without overthinking.

How to “bottom line”

When you only have 90 minutes in a session, you have to get to the f*cking point.

Insights

These are some of the notes that stuck with me:

• We can choose to create positive changes despite unfair situations or biases.
• Your sense of purpose should always be bigger than your profession, even if you’re lucky enough for these to overlap momentarily.
• Humility is leadership.

The personal board of directors vs. a real board of directors

Unlike a real Board of Directors where you:

• Send regular updates with metrics over email
• Get together for quarterly presentations and discussions
• Vote on important issues
• Meet ad hoc for advice, and
• Know everybody has a stake in the company’s success

The Sidebar “personal Board of Directors” format was softer and less tactical, more like a support group.

I wonder how the Sidebar experience might have been different if…

• I was obligated to send a status update email on a regular cadence, or
• My peers had some kind of incentive to ensure I hit my goals and targets

Paper cuts and rough edges

Alright. It’s worth a warning: Sidebar is clearly a startup with a minimum viable product and it’s still working out some kinks.

Right out of the gate, the Sidebar web app felt flaky and buggy. Video streaming connections felt worse than what I typically experience with Zoom or Google Meet. Meeting notification reminders always read out in PDT instead of your working timezone.

Process-wise, the initial matching process took a long time. It took weeks to get paired with an initial core group. After the initial match, we only had a couple of sessions before Sidebar shut down for the holidays. By the time things got into a groove, I was months deep into my paid membership.

There’s apparently a 5,000+ person waitlist for Sidebar, but my guess is there are still only a few hundred active members in the whole community at any given time. The total number of members in the main Sidebar Community channel (think: #general in Slack) has more than doubled since last summer… but if you search the channel for members by name, you can find a lot of people who either churned out or never activated at all.

For example, I happily stumbled on a Sidebar profile for a colleague from a past company. When I messaged him outside of Sidebar to get his take on the experience, he was surprised his profile was showing up in the app list. He hadn’t actively participated because it took so long to match him to a group.

On top of this, Sidebar really wants you to promote Sidebar to your friends—even before you have a chance to experience it for yourself. The onboarding checklist encourages every Sidebar member to add a “Founding Member” badge in their LinkedIn job history.

My general sense is that interest in Sidebar is growing faster than their onboarding process can handle, and they’ve got a leaky bucket problem.

There have been some notable improvements to the chat UI recently (threads!) and I’m hopeful they’ll figure out how to scale user activation.

Would I recommend Sidebar?

Honestly, yea! At the introductory price, despite all the bugs, even with negative value in the first few months, I think the Sidebar program does a good job of delivering on its promise.

The membership fee is similar to what you’d pay for 1:1 executive coaching, but you get the added benefit that you’re learning how to coach as you participate. Or, more pessimistically, you’re paying money to (partially) provide the benefit other members gain.

Either way, what you’ll get out of Sidebar is:

1. The people you’ll meet, and
2. Whatever you put into the program

If you can handle the time commitment and show up in the right headspace, you’re bound to experience connection and personal growth.

Wrapping up

When I joined Sidebar, I had a specific “North Star” career goal in mind. It was a goal I’d been trying to achieve for 10+ years. I had spent thousands of hours and thousands of dollars trying to debug my failure to achieve this goal.

As I got close to the renewal date for my Sidebar membership, I was coming to terms with zero results again. Yet another program, tried and failed. Nothing to show for myself.

Strangely, almost magically, within 24 hours of emailing in to confirm my Sidebar membership wasn’t set to auto renew, my stars shifted. Some circumstances played out and my long-desired outcome came to fruition in a surprisingly understated manner.

The first thing I did was log into Sidebar and check off my goal. I got to watch that neon green checkmark light up in my core group’s channel.

Now I feel like I can take the skills I’ve developed, the lessons I’ve learned, and the energy I was directing toward this one stubborn thing and redirect it to better work.

I’m super grateful for the people I got to meet through Sidebar, and I do hope we can stay in touch! Maybe our paths will cross again in the future.