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Close Before Open: Using Design Thinking Mindsets for Your Year-End Reflection

Over the years practicing, teaching and continuing to learn about design thinking, I’ve experimented with applying the process, methods and mindsets to projects outside of my day-to-day work with The Design Gym and our clients. Whether it be my home yoga studio, advising on a friend’s startup, or solving the wicked problem that is my life, I use elements of design thinking to identify needs, to outline options and, most importantly, to reflect and make decisions.

One of my favorite (and most useful) design thinking concepts are the mindsets of Open, Explore, and Close. To start, we Open our thinking and go wide and generate many possible options. We don’t stop at the obvious or the impossible. Then, we Explore what we’ve laid out by looking for patterns, trying out different combinations and asking “what if?” with a genuine sense of curiosity. To make progress on any project or new idea, we need to Close. We sort, evaluate and select the most appropriate option to take forward. The mindsets of Open, Explore and Close are equally valuable, but should not overlap with each other. You can’t successfully Open and Explore ideas if you’re simultaneously trying to Close.

If you’ve ever led your own design thinking project or attended one of our workshops, you’ll have directly experienced what we mean when we say, how well you close determines how well you can open on the next phase. The same goes for thinking about how to design your life. Closing out a project or year of your life with confidence and clarity will set you up to be truly Open for whatever is coming next.

The Process of Closing: Self-reflection

December is a natural time to be in a Close mindset. The shift in season encourages us to spend more time at home, to be more introspective and to narrow our drink choices—exclusively whiskey and mulled wine.

You likely feel this in your organization as well. Projects are wrapping up, budgets are being spent down and reviews are happening. Hopefully your team is also making time to reflect on the past year—the progress made, the evolution of your processes and the shared experiences that shaped your culture.

We use a lot of frameworks in our work as design thinkers. They help us make sense of information and facilitate a shared understanding of complex data points. And in many cases, they can be used for broader application beyond just design thinking projects or team-based reflections—in this case your life!

Here are three of my favorite frameworks along with examples from my life this past year.

1. Personal Journey: Time + Emotion

This is most similar to the classic stakeholder journey map—plotting a person’s experience from beginning to end and correlating each moment to a positive, neutral, or negative emotional response. This activity is helpful in closing out the year because it allows you to objectively see a snapshot of events, milestones, achievements and bummer moments all together on one page.

Map the events of the past year from January to December along a spectrum of emotional state with neutral, ”meh”, and ¯\_(ツ)_/¯ feels towards the middle, happy and positive feelings up top, and negative or bummer feelings at the bottom. Include significant moments from your personal life, relationships and your work. Seeing all the aspects of your life, laid out on a single page, can be illuminating. You might be surprised at how many events come to mind immediately, and the ones you have to scan for.


2.   +     ∆     <3

This is an iteration of the framework we use for our monthly and weekly team reflections. Listing out the Pluses (things that went well), Deltas (things to change) and Heart State (emotions and feelings) can be a helpful way to document and process events.

I find this framework most helpful for weekly reflection, so I can avoid feeling like everything is blurring together with no clear end or beginning. No worries if you haven’t been doing weekly reflection, you can start at the end of the year and work to make it habit in the New Year.


3. Insights Statements: Closing the close

You’ve laid everything out, now it’s time to make sense of it and identify your themes, learnings and insights.

One of my favorite tools that we frequently share with our community and clients are the Insight Mad Libs questions. Insight can often be an intimidating word—we can get so caught up in striving to have profound statements to summarize our research that we forget sometimes the best insights are the simplest. The more clearly you can state your findings, the better. Same goes for how you frame up your learnings from the past year before you start planning the next.

Here are three iterations of Insight Mad Lib statements that I’ve adapted for self-reflection.

“I thought _________________, but learned ___________________.”

“I spent a lot of energy on _______________, which made me feel ________________, and moving forward I want to __________________.”

“I feel ______________ when I am with / doing _______________, and therefore _____________________.”


Ready to Open

Through the process of leveraging these frameworks to close, you’ll examine all of your varied interests, dreams, passion pursuits, challenges, likes and dislikes. Your insights from closing will enable you to more clearly open in the New Year and harness all of your strengths to crush your goals and be your best self (or selves) come 2017.

Fully acknowledging that closing is not always easy or as fun as Open and Explore mode, it’s essential to developing your whole self and iterating over time—you’ll truly thank yourself for taking the time.

Now, it’s your turn. Take these frameworks for a test drive and let me know how it went. I love hearing from the community on your experiences with design thinking. Also, if you enjoy this blend of design thinking meets life planning, keep an eye out on the newsletter for future dates for our Design(Think)ing Your Life workshop.

And with that, Merry Closing and a Happy New Year!



Recharging Creativity: How To Plan an Inspiration Field Trip

Inspiration field trips can take many forms, but at their core, they’re an experiential way to cultivate team culture while learning and recharging your creative battery packs. Getting out of the office, learning something new, and creating a shared experience together, as colleagues, is also one of the fastest ways to establish greater trust and empathy amongst teammates.

As a company that’s focused on delivering amazing educational experiences, inspiration field trips are essential to our creative process and keeping our brains and workshops fresh. Over the years, running these for our own team, guiding our clients through them, and hearing stories from other organizations, here are some of the most common field trips and how to bring them to your team.

Project Inspiration

If your team is about to tackle a new challenge it can be helpful to hear from other companies and practitioners who have already solved something similar. You’re not looking to copy or steal, but rather to seek out trends, understand the ecosystem, and to see how other organizations approach problem solving. As a team, it’s your choice on how you integrate the inspiration into your existing culture and work style.

We recently wrapped up an 8-week design thinking sprint with a team from New York Life and we kicked-off the project with an entire day of inspiration hunting. The teams were looking to amplify their own culture of curiosity, so we brought them to a handful of companies who have their own innovative approach to learning and development. We closed out the day with a short panel discussion and tableside Q+A with three digital and education industry vets here in the TDG office.

Industry Inspiration

Looking towards companies, products, and services that are tangential to your core industry can often times be a new source of inspiration. Work in sales or retail? Try going to a restaurant that is known for great customer service. We recently did this with the team at Kiehl’s and dropped by a Danny Meyer’s restaurant for lunch to learn from the masters of hospitality. And to keep ourselves up to speed on emerging technology, we swung by the new Samsung 837 lifestyle store for a taste of virtual reality. Who knew that a virtual roller coaster ride after eating ice cream feels just like if you were on the real thing!?

Inspiration field trip to the @samsungusa 837 #inspiration #fieldtrip #instagram #digitalart

A photo posted by The Design Gym (@thedesigngym) on

Creative Inspiration

In our workshops we emphasize the importance of getting into alpha brainwave state (Open and Explore mindsets) to foster creativity, which is a different headspace than being in beta brainwave mode (Close mindset, or what I like to call “get shit done mode”). Literally getting out into a field (or on a boat) might be exactly what your team needs in order to collectively experience a more open and free mindset together.

Our recent surfing trip was scheduled right after what had been a crazy couple of weeks, so it was really important to us to plan the day around an activity that got us reconnected to our bodies in order to free our minds. We’ll often go for walks, take a bike ride, or work from home to change up our physical spaces, but the ocean is literally a sea of creative potential. Pun 100% intended.

Some days you just gotta play. #inspiration #surfsup #playday #teambonding

A photo posted by The Design Gym (@thedesigngym) on

How to Run Your Own Inspiration Field Trip

Leading an off-site adventure requires just as much planning and facilitation as any other gathering of people. If you’re taking on that role, here are some tips on how to guide your team without glitches or needing chaperones.

Set the Intention

Having a clear objective for your field trip is important for setting expectations with those attending, as well as your leadership team. Ideally, leaders within your organization will join. However, whether or not they’re able to join, you’ll need to get them on board—it’s really important that they not only sign off on the field trip, but make clear to all employees that they can attend it without having to worry about what the boss thinks of their afternoon away from their desk.

If possible, your intention for the field trip day should also reflect your company’s mission and core values. For us, we value experiential learning so a day at the beach taking surf lessons actual ticks that box! We also believe in the power of a shared meal together, so we hit the Rockaway Beach Club afterwards for tacos and tequila-infused drinks. This time was incredibly valuable for us to be able to catch-up on our personal lives and share fun-fact style stories in a more relaxed environment than our office or any other lunch spot in NoMad.

Set the Date

Find a time during business hours that works for everyone on your team—perhaps the biggest challenge, but totally worth it. You’ll have the most success if all teammates can join. These outings shouldn’t feel like extra work or cut into personal time, they are part of the job and should be viewed as such. You can get a lot of of value out of two dedicated hours if planned properly, so even if you can only get your team together for a short period of time, still do it!

We usually schedule these on Fridays, year round. Sometimes a full day, but we’ll also do a half day: meeting for lunch, going to 1-2 inspiration spots, and then closing out the day by grabbing a beer(s).

Commit to Guidelines

No emails allowed! Instagramming is OK 🙂 In all seriousness though, taking calls or answering emails during the activity can cause anxiety amongst your teammates. Be sure to lead by example on this one. We will put fun out of office auto-responders on our emails for the days that we’re out with our team. It’s a reinforcement of the culture we are creating for our team and for our client partners and community members. And from what we’ve seen, people look forward to what we have to share when we get back to them the following week.

You can also build in a reflective component to the day. Arm your team with pocket sized notebooks to capture sparks and ideas along the way (we love our pocket-sized Scoutbooks!). A follow-up debrief meeting can be scheduled for the next week to share out what everyone learned and found most impactful. As the leading facilitator, you should capture themes from the debrief to share back with your leadership team, colleagues who weren’t able to join, or other teams who are curious about that awesome inspiration field trip that they heard about through the grapevine.

The Why Behind Inspiration Field Trips

Depending on your current team culture, asking your boss for a small budget to take the team offsite for a day of discovery might be met with several “but why?” questions. Here are a couple of final takeaways from our experience trying out many forms of inspiration field trips that you can use to make the case for why they are effective and valuable.

We’ve learned over the years that creating shared experiences to establish common reference points is important in building and maintaining a tight knit team culture. You can empathize with others all day long, but having been through the same experience alongside one another builds camaraderie and builds a well of “remember that time when” moments your team can draw upon.

These trips also allow your team to learn something new, which adds to the overall skills and reference points your team can draw upon when approaching any project challenge. You’ll learn a lot about yourself and the various strengths present within your teammates by getting outside your comfort zone.

Ready to try one out on your own? Let us know what you’ve got planned and how it goes! Better yet, invite us along if you can 🙂



Team Retrospectives: The Good, The Bad, The Feels

This isn’t the first time we’ve shared a look into our own processes and how we cultivate open and trusting relationships within our team culture. One of the ways our commitment to transparency and continuous improvement comes to life is through our monthly retrospectives as a team.

There are many business-y names for the practice of reflecting on the past—debrief, post-mortem, retrospective (retro for short)—and there’s a good chance you’ve been a participant in this type of meeting at some point. There’s an even better chance that it wasn’t your favorite meeting. We believe strongly in the benefits of routine reflection and in meetings that don’t suck. Here’s an overview of how we do it.

Plan Ahead + Prioritize

Save the dates for our end of month retros are sent out at least 30 days in advance so that we can all hold the time as other commitments are added to our calendars. If it’s planned ahead of time and understood to be a high-priority meeting, you’re less likely to cancel it or have absent team members.

Retro Gear

If you’re taking on the role of facilitator, you’ll want to be prepared. Here’s a handy checklist I use to run a seamless meeting when facilitating our retros.

  • Reserve a room with plenty of wall space or a large whiteboard
  • Make sure each person has a chair and table space or a surface to write on
  • 3×5” sticky notes in five different colors. Everyone should have a stack of each color
  • Sharpies for each person + a handful of whiteboard markers
  • Chill tunes and a speaker—you can use our massive TDG Reflection playlist
  • Food + drink to keep the humans running top notch for the duration of the session

Retro Categories

Looking back without a framework to guide the conversation can feel more like a dump of “oh shit, what just happened” moments instead of a supportive and positive share-out.


We use the following five categories to capture our thoughts into a shared format for discussion and to identify themes and insights. These categories are not only used to sort through our own projects, but also to call out awesome work that our teammates have been cranking on.

  • Good: Things that went well.
  • Bad: Things that did not go well, but are generally one-off events—things that we don’t expect to repeat.
  • Do Better: Things that we can do better next time. These can include a suggestion on how to do it better.
  • Best: Things that went really well. Celebrate! How can we do more of this?
  • Feels + Open Questions: Emotions, mindsets, areas of confusion, and opportunities to consider.

It’s helpful, from a visual perspective, to use a different color Post-it note for each category.


Here’s how our wall looked, in our most recent retro, after everyone on the team shared out their thoughts for each category. All the Best! So much Do Better!


Retro Agenda

As is the case for any meeting you’re planning, an agenda is essential. We’ve tested out a few different agenda formats and this one works best for us.

Feel free to try it out, but as always, make adjustments based on your own team culture. The time blocks for each section will be different depending on how many people you have on your team and how long you can all be together. We have a five person team and we usually block 90 minutes total.

1. Check-in: Before getting into the nitty gritty, we take 30 seconds to each write down and share one word, a short phrase, or emoji sketch that comes to mind to describe the past month. It helps us get a quick read on everyone’s state of mind about the state of our union.

2. Solo Reflection: We put 15 minutes on the timer, turn on the chill tunes, and review our calendars and notebooks silently while capturing thoughts on each of the categories on sticky notes.

3. Share Out: Each person gets 5-10 minutes to share out their thoughts and add their sticky notes to the board. We try to stay silent and reserve questions and “me toos” for the next phase in order to give each person our full attention while they share.


4. Themes, Insights, and Red Flags: We step back, consider everything that was shared, and call out any recurring themes, insights, and red flags that we want to avoid. We capture these on the whiteboard and document them digitally. This way we can keep them in mind throughout the following month and then refer back to them at the next retro to see how we’ve improved (or not—no judgements).

We’ve had “less but better” on our theme list almost every month since January, and instead of beating ourselves up because we still take on more than we probably should, we acknowledge it, and discuss what it means for each of us and how we can continue to make progress towards refining our work (and load).

5. Commitments: Before closing, we take a few minutes to write, “I will __________” statements for what we each personally want to focus on improving or changing, as well as any shared goals or actions. This doesn’t have to be huge or feel like yet another addition to our to-do lists, but rather it’s something that’s aspirational and has a sense of shared accountability.

For example, in January we all said we wanted to commit to working out consistently and we allowed ourselves the permission to go midday or leave a little early to make it happen. We are all happier, healthier and more productive because of it.

6. Check-out: Similar to the one word check-in activity, we take 30 seconds to write down one word that reflects our state of mind in this very moment having just spent the last 60-90 minutes in reflection mode.

Retro on Retros

(So meta!) In reflecting on our process while writing this blog post, we were able to chat about why we do retros, their importance to each of us, and how they benefit the team as a whole. There have been times when we miss a month (or two) and we double up and have a longer retro, but we fully acknowledge that not having time each month to share our thoughts and feelings adds unnecessary strain to the team. We’re a team that embraces getting a little existential every once in awhile, so our reflection time is a shared value. Retros have saved us from burnout, reduced anxiety, and helped us build empathy and create shared enthusiasm for all of our projects and programs.


If you try out this framework with your team or you use a different format let us know! We’d love to hear your stories and tips for facilitating these types of conversations.



Red Burns’ Design Advice

Margaret Stewart, a former student of Red Burns, who was often referred to as the godmother of Silicon Alley, reflected on Burns’ approach to design and technology in a recent Wired article.

“She knew that technology was a means to an end — and that the end was people. She saw it as something you needed to get to the real work: improving people’s lives, making them feel more connected, bringing delight in big and small ways, and empowering them to affect change.”

“Don’t see the world as a market, but rather a place that people live in — you are designing for people, not machines.”

In reading about Burns’ approach to her curriculum, I found that she sought out a diverse group of students who were eager to learn how to solve problems. Working together with a group of strangers with varied backgrounds adds to the challenge and the rewarding feeling of completing a project together — if you’ve ever attended a Design Gym weekend workout or night class you can probably relate! Margaret also captured some of Burns’ quotes during her address to new design students. Here are some standouts that can be applied to the design thinking process.

– Look for the question, not the solution.
– Observe, imagine and create.
– Creativity is not the game preserve of artists, but an intrinsic feature of all human activity.
– In any creative endeavor you will be discomfited and that is part of learning.
– Communicate emotion.
– Don’t see the world as a market, but rather a place that people live in — you are designing for people, not machines.
– Be willing to risk, make mistakes, and learn from failure.