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Design Thinking for Impact: Acumen Global Fellows

Let’s state the obvious: driving social impact is hard. When you set out to change the world, you’re tackling BIG problems. You’re driven by ambitious goals and it can often feel impossible to achieve them. So, how do you create meaningful, sustainable solutions to the world’s biggest problems?

The key is to equip and empower individuals with the resources and tools necessary to make it happen. Recently, we had the chance to team up with Acumen to do just that. We worked with a team of overwhelmingly talented individuals who are tackling one of the world’s biggest problems—poverty.


What Is the Acumen Global Fellows Program?

The Acumen Global Fellows Program is a yearlong fellowship dedicated to training emerging leaders who are committed to solving problems of poverty. They’re a group of awe-inspiring individuals that have done what most of us dream of—taking an alternate path.

Hailing from esteemed careers in entrepreneurship, management consulting, advertising, and non-profit management, these international professionals made the decision to commit themselves to building their skills and using them to change the way the world tackles poverty.

Enter Design Thinking.

The world has tried plenty of obvious methods for wiping out (or at least decreasing) poverty, but still it persists. Multifaceted problems of this nature, in complex environments (like rural villages half way across the globe), are tough. And to tackle them you need a set of tools that helps you develop innovative, human-centered solutions.

Enter design thinking–one of many tools worth having in your toolbox when coming face to face with complex problems with no clear answer.

We partnered with Acumen to provide the fellows with a design thinking bootcamp. The goal: equip the fellows with a problem-solving toolkit that would help them address the complex problems they’ll each be facing on the ground, all over the world, over the next 10 months.

In 2 days, we walked the fellows through the 5 phases of design thinking—examine, understand, ideate, experiment, and distill—and had them apply it to a real-world case: food equity in New York.

On the first day, the fellows learned how to frame this complex issue in a constructive way and gather the data needed to start identifying solutions. That meant speaking to a panel of community food experts, including Tatiana Orlov, Manager of Community Impact for City Harvest; Simone Herbin, Community Food Advocate; and Dennis Derryck, Founder and President of Corbin Hill Food Project.

It also meant getting out in the real world and conducting field research. The fellows travelled to neighborhoods in New York City to conduct in-person interviews with real people that struggle with affordable and reliable access to healthy foods.

Then, on the second day, the fellows took all of the data they collected and set to turning it into actionable insights. Those insights became the seeds of solutions for addressing food inequity.

The Takeaways

It’s very easy to get stuck on the ‘story’ of design thinking—the language we use to describe the process, whether there are 3 steps or 5 steps, discussing how human-centered design has evolved and where it’s going next. This stuff is important, but it shouldn’t be the end goal.

Using this tool out in the real world, on real problems, with real constraints—getting our hands dirty—that’s where the value is. The rigor in process and tools must be balanced with flexibility and adaptability to the problem we’re trying to solve. As each fellow enters their next chapter in different countries across the world, their application of the design thinking tools will look slightly different—and that’s a good thing.

We’re excited to see the creative solutions they come up with to the problems they face and we’re proud to have had the opportunity to work with them.


Transforming Public Schools with Design Thinking

Some people don’t think of the public school system as a hotbed for innovation, but there are many creative and groundbreaking initiatives behind the scenes all over the country.

In New York City, it’s the iZone, a program started by the NYC Department of Education (DOE). The iZone uses design thinking to center learning around the needs of each student. How? One way is to help teachers develop new teaching models. The DOE and iZone also partner with companies in the edtech market to explore emerging technologies.

We spoke to two people who are on the front lines of innovation at the DOE: Kara Chesal, Director of Innovate NYC Schools (an iZone initiative), and Alana Laudone, Director of Special Projects for iZone. They’ve both worked with The Design Gym as community members and clients.

Chesal and Laudone share five tips for moving new ideas and thinking forward in an environment with a large, diverse group of stakeholders.

1. Focus on the Problem, Not the Solution

When you stop being so focused on how you’re going to solve a problem, you can get a better understanding of the product itself—what the user needs, the problem the product will solve, and why you need to solve it.

“If we don’t agree on what the problem is, we’re never actually going to come up with a great solution,” says Chesal.

Chesal worked on a program to incentivize app developers to respond to their request for a proposal (RFP). The idea was to rethink the way the DOE requested responses or bids.

“The typical way the NY State DOE works is a small group of people will set up these requirements and we’ll get responses or bids based on the requirements we put up,” she explains. “We realized that the process was only giving us traditional firms to work with, and folks who had a legal team and the resources to apply to that type of proposal. It also wasn’t giving us the most innovative stuff because we were over-specifying what we wanted. We were giving people a solution. With design thinking, instead of giving people a solution, you can get better at defining what your problem is and allowing people to come in and help you solve the problem.”

2. See Constraints as Opportunities

Where many people see the limitations of working for a government agency as something that stifles creativity and innovation, Chesal sees it as a challenge.

“I think constraints can be opportunities for design, or for design processes,” says Chesal. “Not every barrier is necessarily a flaw of the system. Some can help you define what the problems are more specifically.”

A few years ago, she worked on the high school directory, which is the process by which students and families select a high school. And it’s a complicated process.

“We know we’re not going to be able to change the complexity of that system, and we’re not going to be able to change the admissions methods,” she explains. Instead, they worked on making the experience easier to navigate by narrowing the options down from 800 to a set that matched each individual student.

In this case, Chesal saw a complicated system and saw the opportunity it presented, rather than feeling constrained by it.

3. Meet People Where They Are

People come to design thinking from different backgrounds. Some may already be familiar with the methods, while to others, the information might be brand new. Knowing how to reach your community at every education level goes a long way toward getting them to buy into the concepts.

“The design thinking process—the first time you do it can feel a little silly,” says Chesal. “What we’ve worked to do is make sure that even for their first time, people are doing something that’s related to their work. It’s not building a wallet or something that’s so obscure that they can’t see the relevancy for their own work. It’s not always a natural fit for people because it’s so different, but if you’re able to build empathy and meet them where they are, I think incorporating design thinking into your organization can be very successful.”

Laudone agrees. “Using this new vocabulary can be really helpful and freeing in some ways, but it can also be confusing. These might be something that teachers already do, but they call it something different or they do it in a slightly different way.”

According to Laudone, they’ve had success with layering design thinking concepts within existing frameworks, rather than introducing them as new ideas. For example, a teacher may already be informally asking students for feedback on new teaching materials, but be unaware that it falls under the technique of intercepts in design thinking. If he or she already understands the value of user comments, it may make more sense to work within that framework, with familiar terminology.

4. Design With, Not For

When you’re designing with the end users’ needs at the forefront, it’s easier to get them—and your other stakeholders—to trust the process. Since users are going to be the ones employing the solutions that are designed by the process, it’s best to get them involved from the beginning.

“When you can say that this idea is coming out of schools, and these ideas are owned by schools, proposed by schools, or moved forward by schools, that helps,” Laudone says. “That gives you not only credibility, but legitimacy. Coming from that place shows stakeholders that their ideas are valid. That’s where it starts.”

5. Build a Community Around Learning

Part of design thinking is giving your users the capacity to learn and grow on their own, within their teams, and to teach others as well. That’s how ideas, mindsets and processes travel through organizations and cause big culture shifts.

“The idea of hearing directly from someone in your same position—so that the school-based folks are hearing from other school-based folks that did this design thinking thing—that’s so much more powerful than us standing up there and saying this is how you do this,” says Laudone. ”That’s part of what user-centered design means—always knowing that the user is the expert, and they’re going to have the best perspective.”

No matter what your industry, these tips can help you move new ideas forward and foster innovation. See what The Design Gym can do for your organization, or learn more about our upcoming community events.

Creative Problem Solving at Work

Tackling tough problems at work is something everyone can relate to. They can be as simple as having friction with a coworker, or as complex as trying to come up with the Big Idea that’s going to take your company to the next level. No matter how big or small the challenge is, creative problem solving can help you find the solution and enjoy the process along the way.

Creative problem solving is about more than just brainstorming, and there are a ton of different theories about how it should work. Here at The Design Gym, (and in the world of design thinking) we think of it as a five-step process:

1. Examine: Dig into the problem.
2. Understand: Go deeper and find patterns.
3. Ideate: Come up with lots of ideas.
4. Experiment: Try some things out.
5. Distill: Strip your solution down to the essentials.

The biggest advantage of creative problem solving is that we spend more time defining the problem, which ultimately makes it easier to solve. Imagine that the problem is that your company is in danger of falling short on your sales goals for the quarter. There are two ways of attempting to solve it:

Old way: Get all of the stakeholders in a room together and brainstorm ways to increase sales, like coupons, promotions, and targeted media.

Creative way: Think about why your sales are lower than anticipated. Are your products meeting your customers’ needs? Can they get something better or cheaper elsewhere? Is the sales process too cumbersome? Is your marketing lacking? Ask your customers for feedback to help you answer those questions. Identify short-term solutions for meeting your immediate problem—revenue for this quarter—and actionable long-term solutions that put your customers’ wants and needs front and center, which will ultimately sustain and grow your business.

As we’ve talked about before, when we were starting out as a new company, we had our share of communication challenges. We needed to get creative about working better together as a team. After some work sessions where we followed the design thinking process, we realized we needed structured, regular meetings where we could address those challenges. And it worked!

We Want to Hear Your Stories!

We love being inspired by others who have overcome obstacles at work. When we share our stories of difficulties and triumph, we get to learn from one another. We would love to hear from you and learn from your experiences.

What’s your process for tackling tough problems at work? Let us know about a recent challenge you faced, and how you used creative problem solving to work it out. We’ll compile the top stories and themes and send them out to the community.

Facilitating Team Debriefs: How to End The Year On The Right Note



As joyous as year end can be, I’m sure we’re all feeling the strain of finishing up projects, closing out budgets, and trying to build a strong foundation to kick-off 2016 with.

But in the midst of ‘wrapping’ everything up (pun 100% intended) and transitioning into some well deserved time off, it can be really easy to neglect ‘tying the bow’ on your team and culture. While throwing a magnificent holiday bash is valuable and fun, it’s not enough to make sure everyone is ending the year in a good headspace.

We’re talking about reflective debriefs, and if you want to finish the year with your team feeling heard, feeling confident in what’s to come, and clear on what they learned in the midst of all their hard work, then don’t miss the opportunity to run one. There’s no right way to do it, but we’ve sketched up a few different formats to help set you up to lead your team in an effective one. You don’t need to be the team lead, you don’t need to be an expert facilitator, and you don’t need to have a ton of time.

How To Run A Good Debrief

– Block the time early – debriefs are easy meetings to scratch at the last second. Block the time early, and ask your team to respect it.

– Set the tone up front – debriefs can get negative and invoke complaining if you’re not careful, so as a facilitator let people know the meeting is about translating reflection into new and actionable behaviors for next year. Cut off negative ramblers, and capture concrete lessons to learn from.

– Focus on the Good too – Spend an equal amount on positive and negative feedback. It’s just as important to hear what excited people, what went well, and where the team excelled. Be deliberate in this balance.

– Blameless is Rule #1 – Avoid finger pointing or attaching names too directly to outcomes. Frame it as a team debrief, not individual feedback (that’s a different type of session).

5 Fail Safe Debrief Structures

1. Pluses / Deltas – This is a fundamental framework for debriefing. Have a facilitator lead a discussion making a list of ‘pluses’, things that went well, and ‘deltas’, or things to improve or change next time around. It’s simple but ensures a balance of positive and negative feedback, and can be used in conjunction with most any other feedback framework.

2. The Hotseat – Have the team sit in a circle. Set a timer for 15-30 minutes and ask everyone to capture 3 pluses and 3 deltas for every other person in the circle. Ask people to also capture feedback for themselves as well. Encourage people to be as specific as possible, and establish a tone of positive intention for one another up front.

3. Product / Market / Team fit – This is a very concrete format for debriefing that includes a review of the business as a whole, and not just team members. Made popular by Marc Andreessen, this framework can be used to reflect on how your product or offering did this year, how the market and customer demand has shifted, and how things have gone with your team. Ideally, where these three meet in the middle is where your business opportunity lies. We use it as a way to ask ourselves what happened this past year that we can learn from for next year.


4. Customer / Content / Culture – This is similar to Product/Market/Team, but might feel more relevant depending on your type of organization. What feedback, stories and moments did you hear from your customers this year? What feedback and self-analysis do you have on the content and thinking you did this year? What feedback and key moments happened within the culture of the team? Make sure to highlight key takeaways to help set goals for next year.


5. Impact vs. Enthusiasm – We use this simple framework as a way for prioritizing ideas, but it’s also great for reflection. Have everyone brainstorm a list of initiatives, projects, or other output that happened throughout the year. Then, as a group, plot them based on Impact (what value did it create for the organization or in the world) and enthusiasm (how exciting was it as a team member to work on it). After they’re all posted, ask everyone to step back and reflect on what’s up there. As a facilitator, drive conversations around what you’re seeing. What were people most excited about? What created most impact for the organization? And most importantly, how might we replicate more high impact / high enthusiasm initiatives for next year?

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Final Thoughts

Debriefs are valuable because turn emotional thinking into useful reflection. As a facilitator, using debriefs as an end cap for an experience is an invaluable tool for making sure you end on a good note. As such, trying working them into the end of each week or month as a way to drive consistent reflection and open communication. For us, we’ve begun having our ‘Weekly Celebrations’ at 5:30pm each Friday. It’s just 30 minutes to have a beer and talk about what worked great, and what we can do better next week. No matter what happened that week, it turns the conversation into something positive, and there’s no better way to finish a week than on that note.

If you’re interested in learning more about facilitating effective debriefs and creative sessions, check out our 2016 Facilitation, Sketching, and Design Thinking Bootcamp dates below – each tackles these types of sessions from different angles.

Happy Holidays + Stay awesome,

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Facilitation Skills: Effective Meetings With Difficult People


When it comes to facilitation, it’s not enough to simply have a meeting agenda. Leading a successful discussion often comes down to managing different types of people—and the more difficult the personalities in the room, the harder it is. Successful facilitators adapt their style to meet the needs of the group, and by doing so, draw the best ideas out of their team.

We’ve identified some tough personas you might encounter in meetings and how to tweak your facilitation plan to better manage them. You might recognize these types from your own team, or—gasp!—you might even be one yourself.


While it seems like ramblers just like to hear themselves talk, many are actually thinking out loud and speaking before they have a fully formed idea. Brainstorming is great, but it’s more productive when ideas are better defined before being presented to a group. Ask ramblers to summarize their thoughts into a few bullet points, and then sketch them out to help them focus their thoughts.


Playing devil’s advocate has its place—but when a group is sharing ideas, arguing against their merits stifles productive discussion. Contrarians can cause less confident team members to hold back ideas, which can ultimately lead to fewer contributions to the group. Urge contrarians to expand on ideas rather than criticizing them, and to keep all comments positive. Set rules of the room right away if you know you’ll have a contrarian in the room.


In meetings, ideas will always arise that aren’t on the agenda. Sidetrackers can derail a meeting with too many off-topic discussions. This is where the “parking lot” comes in—a running list of items that come up during a meeting that are worth addressing at another time. The parking lot is helpful for allowing sidetrackers to be heard while also keeping the meeting on-track.

Insistent Sidetrackers

Some sidetrackers keep hammering away at an idea long after it’s been added to the parking lot, disrupting the discussion and making it more difficult to address items on the agenda. A way to deal with insistent sidetrackers is to allow the group to vote on whether to continue the discussion. If team members believe the topic is important enough to discuss, either allow a set amount of time for it, or schedule an alternate meeting.


Bulldozers push their own agenda—as opposed to working as part of a team. Bulldozers are similar to sidetrackers in that they derail meeting productivity, but the difference is that bulldozers stick to the topic at hand while dominating the discussion and interrupting other team members. As a facilitator, it’s important to protect those being bulldozed. Ask other group members to finish or repeat their points if interrupted. The more you give the floor to other people’s contributions, the less power the bulldozer will have over the group.

Quiet Types

There are a few different reasons why someone may be quiet during meetings. They may be shy, intimidated, or just someone who only speaks when they feel they have something important to say. Directly asking them for thoughts may make them uncomfortable, so it’s important to find easier ways for them to contribute. Have the group write down ideas to hand over to the facilitator. Alternatively, break into smaller groups for more focused problem-solving to help make this type feel more comfortable opening up.

For All Types: Empathy is Key

Empathy goes a long way toward dealing with people we perceive as difficult to work with in meetings. When prepping for a meeting, spend time not just on the agenda, but on the participants. One by one, what is each person’s biggest priority? Biggest fear? Biggest strength? Then design the experience to account for it and be prepared to change on the fly.

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Community Spotlight (and TDG New Hire!): Erin Lamberty


Thinking creatively from advertising to education design to yoga.

We were thinking the other day that we do a lot of talking on this newsletter, but the thing that excites us most about The Design Gym isn’t what we’re teaching – it’s what all you bad a%# folks are doing with the stuff you’re learning. It’s incredible.

Since we started, our community has taken this stuff to the NYC Mayor’s Office, the halls of our public schools, the boardrooms of some huge companies, the front lines of non-profit field work, and everywhere in between. Those stories are what it’s really all about, so we’re going to start featuring some of the most inspiring ones in our newsletter to inspire, share, and keep learning.

There was no better place to start than with Erin, because aside from being one of our very first students, she is also the newest member of The Design Gym team! She attended one of our very first Design Thinking Bootcamps over three years ago, and you may have seen her teaching and facilitating Bootcamps in the past two years. Bringing her officially on to the team to lead Community Education programs felt like a natural next step. If you don’t get a chance to celebrate with her at Happy Hour tonight, be sure to give her a high five next time you see her at an event.

We sat down with Erin to get her thoughts on design thinking, why she’s excited to join The Design Gym, and how she applies the design thinking method in her work – and even to her yoga teaching! She also speaks to her experience bringing

How did you first become interested in design thinking?
I was working in advertising, and I noticed a disconnect between what we were creating and what people actually wanted or needed. I started to look for opportunities to learn how to create experiences to better meet customer needs instead of just building what was cool or trendy at the time. That was about four years ago, and the rest is history 🙂

What do you see as the main value of design thinking?
Lately I’ve experienced more value in the process as a mindset for working through end solutions. I know that I will be constantly iterating and improving on what I’m creating so I now ship solutions sooner so that I can test, gather feedback, and then evolve what I’m doing or create something new.

What projects are you kicking off with The Design Gym right now?
I’ll be focusing on our Community Education programs and how we can create the best learning and practice based experiences. I will be working closely with our team of trainers to refine our content, create new materials, and prototype new program formats. I will also be developing systems that help us scale our operations as our programs expand.

What makes you most excited to be a part of The Design Gym team?
I love that The Design Gym is empowering more people with the tools to be designers. Design has traditionally been viewed just as visual, but design is really about understanding a problem and presenting a thoughtful solution, which doesn’t have to be visual at all. The solution might be an experience, or a behavioral change, or a process.

How do you apply design thinking to your yoga teaching?
Design thinking is about understanding people and I do the same in my yoga teaching. Every time I teach a class I come with a rough game plan, but I quickly read the room and energy so that I can guide students through an experience that is appropriate. My class themes each week are also inspired by a variety of sources (aka prompts!) – sometimes anatomy, sometimes poetry, but most times modern day life.
*This interview has been edited and condensed for clarity and length.

Have your own stories about how you’ve brought design thinking, facilitation, or visual thinking to your team or life? We’re looking for more stories to feature, so just shoot us an email at hello@thedesigngym.com with a brief summary and we’ll reach out if it’s a good fit!

Stay awesome,

What’s LARP Got To Do, Got To Do With It?

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Earlier this month we made the annual trek to rural Maine for one of our favorite conferences, Poptech, where we heard a bunch of great speakers talk on the topic of Hybridity. One of the talks that caught our attention was from Alexa Clay, author of The Misfit Economy. Alexa does research on subcultures and the innovation created within and through them.

One of the subcultures she highlighted in her talk was that of LARPing. For those not in the know, here’s the scientifically sound Wikipedia definition:

“A live action role-playing game (LARP) is a form of role-playing game where the participants physically act out their characters’ actions. The players pursue goals within a fictional setting represented by the real world while interacting with each other in character. The outcome of player actions may be mediated by game rules or determined by consensus among players. Event arrangers called gamemasters decide the setting and rules to be used and facilitate the play.”

You can do a simple Google Image search to see just how deep these groups of LARPers get in creating a completely different universe to live within. It might seem silly at first glance, but Alexa’s job is to connect dots, and she posed the question “How do we take this nerdy subculture and apply it to allow us to embody and live out realities?”. She explained hypothetical scenarios of financial institutions trying to understand the possible futures of crypto-currencies, or environmental activists creating full scale neighborhoods representative of what a world without climate change might look like. Our wheels were turning.

Prototyping is an essential part of most creative processes, and certainly the one we teach. One major component we focus on is what we call Role Prototypes, or prototypes that explore the human interactions and emotions with a product or service. One of the best ways to go about testing these human assumptions we have is through role playing.

Now we get it, most office environments don’t exactly ‘welcome’ impromptu theatrical performances during work hours. And of course acting can feel pretty awkward, especially with co-workers. But role playing in the prototyping sense isn’t about acting, it’s about tapping into the emotions that are built into our DNA, the human side of things that we’re all born with.

When was the last time you truly put yourself in your user’s shoes…we mean literally in your users shoes? As you’re exploring big ideas or new products, how can you mock-up the actual world that product is supposed to live within, and throw yourself smack dab in the middle of it? Then most importantly, take note of the emotions you’re feeling, because chances are they’re the ones your users will feel to, good and bad.


PS – Check out Alexa Clay’s full Poptech talk here.

PPS – If you’re interested in LARP-ing, VICE recently did a mini documentary on how some folks are using it as a positive social outlet. Check it out here.

PPPS – Tina Turner reference anyone? Anyone?

The Difference Between Employee Empathy and Customer Empathy


It’s 10:00pm. The team is sitting around a table, cranking. You can feel the tiredness hanging in the air, like a ghost that’s bent on making it’s presence known. The big due date has been looming for months but somehow it turned into tomorrow and you’ve found yourself in the situation that you all promised you wouldn’t be in month ago.

Then…out of the corner of your weary, bloodshot eye you see it. It’s [insert co-worker here], and they are on their cell phone.

Texting. TEXTING!?!

Again. AGAIN!?!

BAH $%&@!!!

Here you are, typing your heart on to put the finishing touches on [insert big deadline item here] and there they are – sitting over there relishing in the disconnect of their digital life. Well let me tell you, we’re not standing for it anymore. Nope, not today. Your mouth jars open and before you can catch yourself you see a bunch of startled faces responding to the ‘Hey! Let me tell you….’ statements that you clearly must’ve just vocalized. And all of a sudden, a very long night just turned into a much longer night.

So often in design thinking and creative work we talk about building user empathy, but rarely do we take the time to build empathy and dialogue with those sitting a few feet over. When a project comes in, our first inclination is to assign roles, put a plan on it, and get the ball rolling. It might work, right up until it doesn’t, and then it fails in a big way. It’s those moments in the 9th hour, with fires burning and emotions high that you start to question each other, and it just so happens those are the last moments you want to be questioning your own team. Sure, your team mate might have been just goofing off, but it very well might have been their mother’s birthday that they almost forgot, or one of their children that has been battling a cold, or just a well deserved break before diving back in. These false assumptions are the ones that show up in the worst ways at the worst times.

We use a really simple tool to help build this understanding early and often in team settings – Personal Persona Sheets:

As you’re kicking off a project, spend an 30-60 minutes having each person create their own Personal Persona sheet. It doesn’t need to take long, just 5-10 minutes. Then give each team member the floor for another 5-10 minutes to share out what they created. Here are the categories we ask each person to capture:

– Your Name

– Communication Style – How do you tend to bring thoughts to your team? Are you the person with the big, lofty ideas, or are you the person who is a master of seeing roadblocks? Should your teammates expect concrete, well thought out details, or half-baked ground breaking sketches?

– Personality Type – How do you typically show up? Are you an in your face, call it like it is person? Or are you the silent one processing to yourself? Or (dare say it) passive aggressive combination of the two?

– Strengths – In moments of need, what can your team count on you to shine in? Are you the team comedian? The visual facilitator? The one known for spurring coffee walks to unwind?

– Mindshare – The most oft forgotten, and perhaps most important. What else is going on in your life that might have you distracted or prevent you from being present in the moment? It could be family, personal, emotional, or something else, but let’s be honest – we’re all human. When your team catches you texting…again…what is it that’s going on?

You can customize these to whatever works best for you. Sometimes we include things like personal excitement for a given project, or biggest fears around the work being done, or skillsets most trying to improve. There are no right or wrong answers. The point is to have the conversation, to level set amongst the team before diving headfirst into the trenches of hard work. Give it a try, there’s little to lose.

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)



HIRING: Marketing Director (NYC)


Company overview

The Design Gym is an educational company that teaches some of the most forward thinking organizations in the world how to infuse their culture with greater autonomy and tools to enhance collaboration. We’ve had the pleasure of working with the NYC Dept. of Education, Capital One, Etsy, DonorsChoose.org, Marriott and Next Big Sound to name a few. In addition to our client work we teach public classes that make the tools of Design Thinking, facilitation, and creative thinking accessible to the fine folks of New York City. We have been experiencing substantial growth in the past 12 months and are thrilled to be inviting some motivated and creative folks to join us for the next chapter.

Job description

The Marketing Director will collaborate with the TDG Managing Partners to build and implement a cohesive strategy to support the growth of both sides of the business (public and corporate). This role begs a balance of a wide variety of skills, making it both exciting and challenging. Some of the hats that will need to be worn include: community catalyst, developer of strategic insights and archetypes, amplifier of the interesting, and translator to make messages cohesive across the two primary business units.

Responsibilities include:

– Working with Managing Partners to set key objectives for marketing and build cohesive strategy around those objectives

– Reviewing marketing analytics to assess effectiveness of strategy and make changes as needed

– Growing brand awareness in the NYC market to support ‘butt’s in seats’ for our public classes and business development for our client work

– Developing campaigns and strategies to help TDG break into new geographic markets

– Oversee our agency relationships, a team of freelancers and part-time marketers to support key business objectives.

– Developing and executing our content strategy, including writing our newsletter, filling social media queues, and partnering with internal and external stakeholders to develop thought leadership

– Brainstorming and planning unique events and activations to boost the brand

– Strengthening relationships with media outlets to expand PR

– Interviewing clients and community members to learn about where we fit in their life, and testimonials we can share more broadly

What we’re looking for:

– Someone with at least 5 – 8 years of experience in a diversity of marketing roles, having both overseen teams and delivered on implementation

– Ideally someone who has worked in a role motivating and moving communities of people, such as in community groups, growing companies, political organizing, fundraising or events promotion.

– A gifted writer who enjoys writing

– Experience with large scale content strategy and growing community lists via digital and in physical channels

– Ideally working experience with Mailchimp, Buffer, Google Analytics, and WordPress. Adobe Creative Suite is a plus.

– A person with the confidence to build their own plan, own it when it doesn’t work and find ways to work around roadblocks.

– A strong network and a track record for creating impact within that network for the betterment of the people in it.

– The ability to navigate ambiguity and bounce between high-level strategy and working through the details.

The single greatest factor we’ve found in successful team members is a strong sense of self-awareness. We’re not looking for a perfect person as we don’t come close to fitting that mold ourselves – but we do need a sharp collaborator with a strong sense of honesty and willingness to go all in on the work. Also, it’s just plain non-negotiable that you’re fun to be around – we play by the no ass holes rule.


Email us at jobs@thedesigngym.com with the subject line ‘Marketing Director’. Please include:

– Resume

– Something to let us know why you think you’re a good fit for the job (cover letter, interactions with TDG, portfolio, feature length film)

– 300 words or less on a community you’re inspired by and what you believe it is they’re rallying around