The Meetings that Saved our Culture (Yes…Meetings)

With organizations, most people draw a direct correlation between larger with slower, more hierarchical, and less authentic communication. We reference the ‘cog in the machine’ stereotype as we dream of those teams that are faster, more entrepreneurial, and less complex. Ah, if only we were a startup.

Sound familiar? It’s because this dichotomy between big business and small business is pushed on us in the media on a daily basis. But any small business employee can be the first to tell you—while it is true things can move faster, it surely doesn’t mean that it’s any easier to keep a team happy and communicating. We’ve seen startups, public schools, global non-profits and Fortune 100 companies struggling from the same team issues, and size has no influence on their ability to remedy them. But rather their ability to have honest and open communication over and over. It’s a game of good relationships at the end of the day.


In our early days as a small team, we found the daily stresses and ambiguity of a new business overwhelming. From the outside, people saw fun events like Design Taco and innovative new class formats like the Studio Project, but internally communication was breaking, trust was dwindling, and general excitement for the business we were building was strained.

Luckily as a company that advocates for leaning into tough challenges, we did what any good design thinking process would advocate—we asked the hard questions, figured out some patterns, and crafted some solutions to begin prototyping. These were hard conversations over several meetings. But the further we got, the more we started to see clear patterns around what we needed:

It became painfully obvious that although these were the items most critical to our shared success, not a single meeting we held was focused around any of them. At the time, all of our meetings were a jumbled mess of team, culture, strategy, accountability, and general new business freak out sessions.

We all pulled out our technology and in about 10 minutes of calendaring our first round of prototypes were set. Little did we know but we were on our way to drastically remedying some major breakdowns in the team. Here are some of the meetings we still hold weekly that you might be interested in stealing or adapting for your team:


Positive Intention Touchpoints:

Uncomfortable Conversations (every Monday morning) – A safe place to air the grudges, gnawing annoyances, or even personal insecurities living in the back of our heads. These keep disruptive emotions contained, rather than bubbling up in passive or aggressive manners. Best done over Indian food outside of the office.

Weekly Celebrations (every Friday, end of day) – A chance to reflect on what went well, both personally and as a team.

Shared Passion Touchpoints:

Mindset Check-ins (every Monday Morning) – a chance to get the pulse on each person. Where is each individual’s head at? What are they sketching? What are they excited about? What are they scared about?

Strategy Sessions (quarterly) – Blending accountability conversations with strategic planning is exhausting and ineffective. Now we reflect and steer the ship in a direction each quarter and try not to question it too much while executing.

Fishing/Skiing Trips (full day every 1-2 months) – Why fishing and skiing? No reason other than that we all love them and they can all be done easily in 1 day. They both allow for lots of downtime on lifts and waiting for whales to bite, which gives us lots of time for reflection on the exciting thing we’re working on together.

Clear Roles Touchpoints:

Top 3 Goals (every Monday Morning) – A chance to share out the top 3 things we are each hoping to accomplish this week to move our sides of the business forward. We also discuss roadblocks and ask for help from each other if needed.

Brain Trusts (monthly) – A chance to share out what we’re working on to get builds and input from the team. We also use this as a chance to hold each other accountable to what we’ve set out for during the quarter, and course correct if needed. We choose a month to have enough time to balance unexpected fires with continuing to make progress.


Remember: Heads down working will drive the business, but heads up relationships will drive the team. Find those levers and build the rituals into every week. (TWEET THIS)



Andy Hagerman
[email protected]

The Design Gym is a strategy and innovation consultancy helping leaders to grow their business by fully unlocking the power of their most important asset: their people. We work at the intersection of business strategy, experience design, and change management to engage the people that matter most to your work: your customers, your leaders, and your employees. Andy Hagerman is one of the co-founders and partners at the organization and is based in Beacon, New York. See something that resonates with a project or challenge you're working on? Shoot me a note at [email protected]. I’d love to connect.

  • Creative Problem Solving at Work -
    Posted at 19:13h, 29 December Reply

    […] we’ve talked about before, when we were starting out as a new company, we had our share of communication challenges. We […]

  • Bonnie Goldblum
    Posted at 18:47h, 04 April Reply

    I love the clarity of purpose for each meeting. Mondays can be a challenge for many people, after the weekend and the meetings look a bit intense. Do you cover Uncomfortable Conversations , Mindset check-ins and Top 3 goals in one meeting?

    Thanks for sharing your experience.


    • Andy Hagerman
      Posted at 14:28h, 12 April Reply

      Hi Bonnie – thanks for reaching out, and great question! Rarely do we integrate all 3 into one meeting. The specific one to make space for is the Uncomfortable Conversations. These are essential to healthy team culture, but need to be handled delicately. They’re best served in small format – think 2-3 people who need to address a specific challenge they are facing. They aren’t the types of topics you generally want to bring up in a large group setting, or at least not without the help of a skilled facilitator. For Uncomfortable Conversations, you generally need to spend more time trying to build the habit into your culture for people to feel comfortable asking for one when they need it and who they need it with. You don’t want to force them, but you do want your team to feel comfortable raising a flag with someone when it’d be helpful.

      Mindset check-ins we do leverage in most of our meetings. It’s a valuable way to start off, and get a sense of how everyone is doing – both in context to this meeting and work, but also as a whole human. It helps level set on why people are showing up in a certain way, and that often extends well beyond work.

      Top 3 goals are also great for Monday kick-offs, and we do use them in this setting. Something we’ve been experimenting with since originally writing this post, is digitizing these updates. We’ve been using things like Slack, SlackBot, and even experimented with group texts at one point (wouldn’t recommend this as a habit – not scalable!).

      Hope this helps!

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