Behind The Scenes of A Mastermind

In the Crossfit world, it’s a known fact that having a partner can lead to seeing results more quickly. Having a community of people supporting each other through growth has been proven to see drastic improvements.  Little did I know, how this pair-working concept would translate so well into remote-work.

I was first introduced to the concept of Masterminds at my dream company Buffer where I work as a Customer Advocate.  At Buffer, we’re strongly encouraged to work where we’re happiest. Meaning our entire 84-person team is a distributed team working remotely from all over the world. The main downside to having a fully distributed team is that I only see my co-workers in person a few times a year which is a lot less than what a normal “office” setting would provide.

In a recent work study by LinkedIn about Relationships at Work, they found that 46% of work professionals worldwide believe that work friends/buddies are important to their overall happiness.

As silly as it may seem, the general consensus is that “if you can enjoy what you’re doing and enjoy the people around you, it makes you care more about what you’re doing. When you care about what you’re doing, you’re more productive.” The challenge was, how can we translate that to remote-work, with a team where individuals work all across the globe?

That’s where “Masterminding” comes in, it’s been part of Buffer’s cultural DNA since the beginning, (our CEO Joel, and Co-Founder Leo first kicked off the idea). In essence, Masterminds pair up two team members for regular coaching & support. Mastermind buddies are encouraged to meet regularly once a week or 2x a month to share triumphs, challenges, and goals (GIF’s are highly encouraged too). The key difference between masterminds & 1:1’s is the relationship: Masterminds are peer-to-peer while 1:1’s are a mentor/mentee relationship.

My only regret is, I wish I would’ve started Masterminding sooner. 

The idea came up naturally & casually one day, when my long-time friend and teammate Dee asked if we could Mastermind. Of course, I said HELL YES. I was stoked to give it a try. At first, we both agreed to kick things off slowly and try out Masterminding as an experiment since both of our schedules were jam packed.

You see, I was familiar with mastermind groups as a concept, but I hadn’t really tried peer-to-peer Masterminding with a teammate yet. Generally, we had strayed away from the idea of masterminding at Buffer. (Update: We now have a Mastermind Program at Buffer to strongly encourage peer-to-peer pairing/mentorship)

Based off past experience I generally worked best alone. Not that I didn’t enjoy being on a team working side-by-side with my awesome teammates. But, my best work required deep focus, which came from working solo. My old approach, was to bring problems/issues to the table (particularly in my 1:1 with my team lead) when I needed help. I soon discovered, the hidden benefit to Masterminding is that it gives you the chance to work through roadblocks proactively instead of reactively.  In essence, you’re able to work through roadblocks faster & more efficiently when you’re able to meet with someone regularly and bring your successes/challenges/goals to the table.

Some Key Learnings:

  • In order to really reap the benefits to Masterminding, vulnerability & trust is required. You’ll need to be vulnerable  and be willing to open up about your weaknesses & strengths. This requires building trust and camaraderie from the get-go. You see, it’s during my most challenging/vulnerable times that I was able to discover my way through it, at least that was the case for me.
  • Don’t expect your Mastermind buddy to have all the right answers. That’s not their job. Their job is to listen and support you through the challenges. Their job isn’t to give you all the answers, there job is to help guide you in finding the answers by asking the right questions & to challenge you.  I soon realized, having that fresh perspective would help me go back to the drawing board and come up with new ideas/solutions.
  • To have a successful Mastermind, you can’t Mastermind which just anyone. The key is choosing the right person. Here’s a couple of things to look for in a Mastermind buddy. Choose someone who..
    • You can relate to on a professional level or someone you look up to on a career.
    • Genuinely cares about your professional & personal growth. You’ll be their cheerleader/supporter too, so be sure to choose someone you can do the same for.
    • Will push you outside of your comfort zone & support you thru your challenges.
    • You work on the same or similar timezone as. If you’re going to meet regularly, having regular cross-over time is key.

I was luckier than most in that Buffer as a whole attracts some of the most amazing, talented, down-to-earth and genuinely funny people I’ve ever met.  We’re ALL positive, no ego-doers, and we inspire each other to live smarter not harder – which goes hand-in hand with the 10 values Buffer was built on. If you had spun the imaginary Wheel of Fortune, and had been given the chance to Mastermind with any one of the 84 individuals at Buffer, you’d have won the Mastermind lottery.

I was particularly lucky in that my Mastermind buddy and I had already been long-standing friends & close teammates for 2 and a half years. We already knew each other well and we had built a solid foundation of camaraderie & trust. We have each other’s backs, both professionally and personally. No bullshit. No politics. We’re in each other’s corner to cheer each other on and support one another to reach our goals.


We kicked off our Mastermind casually – chatting about allthethings from our work goals/challenges, to nutrition, to book recommendations, and even some life-challenges like my recent breakup or Dee gearing up to buy a new house. Generally, we’d check in on each other regularly in Slack and schedule a Zoom meeting for every other week outside of our regular 1:1 with our team leads. One day, Dee came to me with a pitch – he had created this point-system to help us achieve our goals. The idea was simple, we’d check in once a week or every other week and share our goals. (i.e. day-to-day tasks, work projects, gym/fitness goals, or even nutrition goals)  For every goal that we achieved, we’d get a point. And at the end of the quarter, we’d tally our points. If we did well, we both promised we’d send each other a surprise gift.

The goal wasn’t to get things perfect – it was to inspire growth and help us hold each other accountable.  Masterminding quickly became more than just about professional growth. It was those bi- weekly one-hour blocks of time, that started to inspire some of the most professional/personal growth out of me.

I started to notice that our Mastermind sessions had positive effects outside of my professional career, it spilled over into my personal life & habits.  I was more adept to making healthier life choices with my diet/fitness. Dee was on track to follow his nutrition plan and his workout regime; while I was making tweaks to my diet to become more plant-based and had challenged myself fitness-wise to switch from Pilates to Crossfit to focus on strength-conditioning. Work-wise we were supporting each other through the ups and downs of work and challenging each other to step outside our comfort zones and approach things from a different perspective/mindset. Truthfully, Masterminding made us both stronger teammates. We were better equipped to conquer challenges and advance career-wise.

My only regret with all of this, I wish I would’ve started Masterminding sooner.  I had underestimated the power of masterminding. Fast-forward to 8 months later, Dee and I masterminding regularly, we’re still tracking our goals and tallying up our points. (Spoiler alert, we did do a surprise gift-exchange at our company retreat in San Diego in April) We’re still goal-swapping, and tally our points, but more importantly we’re cheering each other on and actively supporting/challenging one another. I’m genuinely grateful to work side-by-side with such a rad teammate. Thanks for being my Mastermind partner-in-crime, Dee!

Surround yourself with people who make you laugh, allow you to be vulnerable, yet push you forward and lift you up. Most importantly, make sure you do the same for them.


  • Come prepared. Take 5-10 minutes to reflect on what you want to share beforehand.
  • Take the time in the beginning to build trust. Learn about each other, even if it may seem mundane. You’re building the foundation to your Mastermind. You’ll reap the benefits later.
  • Respect each other’s time & try not to interrupt. Let the other person speak and fully open up.
  • Ask questions. Help the other person dig deep. (Here’s a really awesome list from Kevan Lee!)

Format/Ideas to Try:

  • Carve out equal parts for both Mastermind buddies to share. Generally, Buffer encourages 1 hour blocks of time. (30 mins for your Mastermind buddy to share goals, challenges, or triumphs and 30 mins for you to do the same) The format can be flexible. The main goal is to have both parties sharing equally.

Mastermind Questions to Try:

  • What do you think about that really gets you excited?
  • Have you seen something recently and thought to yourself “I wish we’d done that”?
  • What is a dream or goal that you’re working towards right now?
  • What’s on your mind? … Anything else? ( In the book The Coaching Habit, this question is framed as “And what else?” The idea is that you can keep asking this question over and over to keep giving a teammate the chance to share fully.
  • What’s the real challenge here for you? How can I help?

Checkout the full list of questions from Kevan Lee here.

So my challenge to you – is to reach out to someone you respect and see if they want to do a Mastermind with you. Happy Masterminding! 😉


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I like big books & I cannot lie.

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