Blogs by InnovatorsBox®

Rethink Online Collaboration with Innovator’s Digital Playbook

Ever walked out of a meeting feeling more confused or discouraged? Yes, if you haven’t raised your hand, I want to know what kind of meetings you’ve attended! Yes, this is a feeling all of us have felt many times in group projects. From student group projects, vacation trips with friends, to business projects – there is so much room for miscommunication and misunderstanding. But if we participate in group collaborations all the time in different ways, why does this continue feel so challenging? 

On top of that, now with the pandemic, we’ve had to learn how to do this all online where a lot of the nuances we could carry in person is now missed and lost in translation in a flat-tone email. For instance, can you tell if I’m joking or being serious unless I add an exclamation point? It’s hard to catch all the nuances in a 2D screen. That being said, finding a way to work better together online is not impossible because most people do mean good intentions. We just don’t always have the tools to know how to collaborate online better. 

So, if you are seeking to find a better way, look no further. I’m thrilled to introduce you to a tool that you’d love rereading and reusing in every meeting. Meet the Innovator’s Digital Playbook!!

I’m thrilled to introduce you to the Innovator’s Digital Playbook that me, Daniel Friedman, and R.J. Cordes have written thinking of you! Yes, farewell to bad meetings and hello innovative inclusive team collaboration and innovation projects.

Meet the Authors!

Monica H. Kang loves holding creative safe rooms where everyone feels heard. As the Founder & CEO of InnovatorsBox® and the Author of Rethink Creativity, she is eager to help more people enjoy creating safe rooms in which to collaborate and connect—even if it’s only online. She wants everyone to feel they can show up as who they are and hopes this document will give readers further insight into gaining self-esteem via collaboration.

Daniel A. Friedman is a researcher and community organizer in California, USA. Through initiatives such as the Cognitive Security & Education Forum (COGSEC) and Complexity Weekend community of practice, he is exploring how online teams can be healthy, creative, and productive. He sees a bright future for new forms of collaboration—such as the use of Catechisms from team inception to product delivery.

R.J. Cordes is a researcher interested in collective sensemaking. After spending years contributing to and facilitating a variety of remote working groups, committees, and teams, he has shifted his focus to how emergent online teams and communities share information, stay aligned, and achieve their goals reliably.

We met through Complexity Weekend, a hackathon-like program where diverse innovators come together to solve complex world problems within a weekend. Daniel is one of the co-founders. R.J. and I were some of the active facilitators and partners. 

Each of us loved witnessing the innovation, collaboration, and new friendships that were forming over the weekend and beyond. But as the program evolved into series of checkpoints and monthly programming, we quickly saw a common challenge.

Working online together with strangers is not easy! 

Working on any project online, even with friends you know well, is not easy! We take it for granted when we do have teams that work well that we don’t get to reflect and recognize, ‘hey what made us work well?’ As we reflected as friends and partners of Complexity Weekend, we wondered what tools could help not only teams at Complexity Weekend but also the larger innovators community in general, when it comes to online communication and collaboration. 

Each of us comes from different background, expertise, and experiences but there were things we learned to work together that we wish we could carry back to our different communities too. It made us curious what we could do to come together to create a tool that could empower others?

This is how we got inspired and want to go to the drawing board to create a resource and guide that could empower all to collaborate, innovate and facilitate online better. More joy and innovation and less pain and confusion. 

Monica: What inspired you to want to write this playbook?

Daniel A. Friedman

Along with R.J. and Monica, I've long had a passion for exploring how individuals find creative and productive approaches to work. As the nature of work and collaboration continues to evolve, I was curious about what kind of products and artifacts would be relevant for modern terms. With R.J. and in other collaborations, we had made outputs that looked more like traditional research papers. So it was inspirational for me to take a first-principles approach to what an Innovator's Digital Playbook could look like!

R.J. Cordes

As someone who had been spending most of my professional life working remote, seeing so many people struggling with adjustment during the pandemic made me wonder how I might both communicate what I had learned, and learn more from others.


The irony to this project is that we got to be reminded of the lessons we wanted to share with others in our own development! Here we were wanting to write a guide about a group project and working together as a group. So as we went through each stage of development we were humbly reminded how our very experience building this is a reminder to the areas we could help flesh out more tools, resources and lessons learned that we don’t want to forget. 

From how the first meeting is scheduled to how we face disagreements and conflicts. We’re human, of course, we have moments of disagreement. In fact, if you are in a room of full agreement that may mean people are not fully being honest or feeling safe to express their different points of view so having a room of different opinions peacefully and respectfully is an important part of the process, not a bad one! And of course, the many moments we felt that ‘aha moment’s of connecting the dots is when we were reminded how can we channel this and create this well so that we could help more people experience that powerful flow all the time in every project with joy and curiosity? This is why, I was also really excited about how this idea evolved into a bigger project. 

While some initial thoughts were mapped out by Daniel and R.J. who had worked on another guide called the Catechism and Facilitator’s Catechism Playbook last year, coming together permitted us to expand the project focus to be deeper into inclusion, equity, psychological safety, and assuming good intentions. I emphasize assuming good intentions because I realize the number one reason why many group projects fall apart was due to a lot of miscommunications and misunderstandings despite good intentions. 

I felt some of the guides I read often came from assuming that the party who is reading does not care about the rules or has to do it but does not enjoy doing so. I craved a guide and resource that made me feel understood and helped me feel that it’s ok that I may make some mistakes at first because I’m still learning and that this will not be an overnight process.

Monica: Tell us a bit more about the Catechism? How did it get started?

R.J. Cordes

Personally, I think it got started back in 2019 - Daniel and I were lead writers on a proposal that required a “Heilmeier’s Catechism”, a set of 8 questions about the project which required answers in order to start work. When we looked over it at the end of the writing process, we realized, “these 8 questions and answers communicate the project better than the 25 page proposal”. Not only that, but we thought about what would have happened if we had started with the catechism, rather than built it from the proposal? We came back to the Heilmeier a few times when we felt unsure on alignment on later projects and we thought, “why does this work so well?” and “how could this get adapted for remote teams?” Those questions led to the “Facilitator's Catechism”, but it was Dr. Steve Phelan who asked the question “how could this get adapted for innovation teams?” that led to the “Innovator’s Catechism” found in the guide.

Monica: What were some lessons learned from the first Catechism that you were able to build on in this Playbook development?

Daniel A. Friedman

The initial Innovator's Catechism publication in 2020 (with Phelan, Cordes, Friedman), gave me insight into how the world of entrepreneurship and innovation. Here I always think about the first lines of the paper, probably written by Prof. Phelan: "An invention is something that is new and potentially useful. An innovation, on the other hand, is an invention where the benefits, financial or otherwise, exceed the costs of developing and executing the idea." -- This idea that "innovation" is about the synthesis of creativity and utility, really stayed with me.   

This is why, I was reminded how in group projects you have to let go of your expectation of how things will be done. If I were to work alone, I’d probably have a certain way of doing things that may be efficient for me. But is that right for Daniel and R.J.? Probably not. And vice versa! If they asked to follow one person’s way as the only way then other parties would have felt left out. Yet often in group projects, things tend to be led by the most vocal but not the most inclusive voice so as we iterated our goals, expectations, and processes it was heartwarming to be reminded how important it is to constantly evolve, listen and learn from one another to reach your goal and milestones together. Working together as a team, not as a solo is key.

Monica: What does good collaboration look like for you?

Daniel A. Friedman

There are so many interesting aspects of this and ways to address it. One thought I've heard elsewhere is that good collaboration is like a healthy garden. Above ground, we see the strong stems and flowering outcomes that happen when we work together harmoniously. Also, there is the below-ground component of collaboration, which might reflect shared values, understandings, and ways of working. There are multiple rhythms to the collaboration, for example, the daily rhythms of photosynthesis and annual rhythms of productivity. Also, there are parts of the garden ecosystem that might not be seen from just a glance, like bee pollinators or microbes in the soil. All of these outcomes and processes that make a garden a relaxing, meaningful, and sustaining area of land, are patterns that can be cultivated in collaboration.  

Another opportunity I enjoyed in this project was just the opportunity to write and reflect. It’s one thing to feel we are doing a good job collaborating when we work with other friends and colleagues it was another to take a step back and really ask, hey what are the steps that we realize really played a key role in bridging relationships and collaboration even when working online and what was not? It was humbling to realize how many elements and variables really required good collaboration and intentional trust-building especially when it came to online. Since the three of us came from different backgrounds it was really helpful to constantly remind ourselves as a group to see things from diverse lenses and reflect on how the writing will be communicated to all readers. How can we empower them whether it’s an executive, a weekend ideation group, or a student working on collaboration projects online? 

I appreciated the opportunity in how we devised this focused on clear accountability and responsibility also without needing to do too many group meetings. In fact, if I’m recalling correctly as a group we only had four 60 min meetings between June to November. (One in June, July, September, and October.) That’s really impressive looking back! Yes, we had 100s of emails and documents sorting out but because we understood how hard it may be to find a common time to discuss live we used our live sessions to discuss key priorities and used emails, google documents, and other workstreams to communicate, collaborate and ideate. I loved the opportunity to write the beginning of the documents, identifying illustrators, and working on the creative pieces together with our partners, while Daniel led the overall pace, timeline, organization, and with R.J. on the Catechism. 

Monica: What was your favorite part of working on this project? Why?

Daniel A. Friedman

My favorite part (so far) in this project has been how it is so question-based. In research, certainly forming good questions is part of the writing process -- however, the final research paper is usually framed more like it is an "answer" and less like it is a "question". In the IDP, in different ways across the sections, we were able to keep this inquisitiveness front and center so it was refreshing and fun. Also, I've enjoyed the process of learning how to interface with new kinds of digital professionals during this process, for example, graphical designers and illustrators.

Monica: What was the most challenging part of working on this project? Why?

Daniel A. Friedman

The most challenging part of working on this project was probably deciding what information would be general enough to apply to a variety of teams, while also remaining specific enough to be actionable and relevant.  It's a general challenge in collaborations to achieve a coherent understanding among team members that are also communicable. What ameliorated this challenge was the knowledge that I could provide any thoughts in our meetings & shared documents so that RJ and Monica could hone these insights, and that I would do the same for them.

In all, it helped that we had a deadline we wanted to aim for despite all the busy workload we also had as a team – making this available before the upcoming Complexity Weekend in November 2021 so that teams could start using it there and make this available soon to many others. Since our intention was also to ensure this was more design-friendly and widely useable beyond a traditional document reader, we built in more time to incorporate a design-friendly guide, original illustrations from abiyyusw, and other creative resources.

Monica: What was your favorite part of working on this project? Why?

R.J. Cordes

My favorite part about this project is the same as it would be in any collaborative writing project, the opportunity to learn from the methods and insights of my teammates - and, more importantly, from their interactions. Every team is different because every person is different, each carries a unique narrative about workflow, process, and the meaning of the work - creating opportunities to learn about the interactions of various methods and work-styles that can only come from being a part of a team.

Monica: What was the most challenging part of working on this project? Why?

R.J. Cordes

The most challenging part, for me, was the tradeoff between communication and explanation - the need to communicate a lot of information, without necessarily going too deep into the “why” behind it. Daniel and I have written a lot together, in formats that generally allow us to do deep dives into why some practices in remote teams work the way they do - so focusing on the what and how was a challenge but also an opportunity to learn.

In all, I loved the unique opportunity to reflect on what our audience may need by thinking about what we found helpful in our own journey building this guide for you. And I’m so excited to finally share that after many months of ideation that it’s finally ready for you!


I can’t wait for you to use the Innovator’s Digital Playbook! There are many ways you could access it. From the full document, worksheets, editable google guide, to more creative visuals and resources you could all find it at our website which would be available for all for free. 

Yes, we are making these resources free in order to help more innovators have an inclusive innovative workplace and collaboration no matter who they work with. We hope that this guide could be the start of many new insights and discoveries and collaboration. And as any iteration goes, there is always going to be room for improvement. 

Please reach out to us if you have any other suggestions, questions or thoughts that you want to add. We love to hear from you and we can’t wait to see how this could empower you and your community. Thank you for taking a moment to read our back story reflection and using the guide to empower your team and project!

A few more thoughts that my co-authors want to share with you!

Monica: What do you hope users would feel using this Playbook?

Daniel A. Friedman

I hope users would feel like they had found a resource and tool that spoke to them, in terms of being applicable to the situations they actually find themselves in. Also it would be great if people could feel more focused or less stressed, knowing that by being thoughtful in their online collaborations they could have an impact on their lives, teams, and projects!

R.J. Cordes

I’d hope they’d feel a little more prepared to tackle work as part of a remote team, and, most importantly - not alone.

Monica: What are other guides you think would help other innovators incubate new ideas?

Daniel A. Friedman

In terms of resources that can be returned to again and again while incubating new ideas, there are many options and we mention some in the further reading section of the IDP. Specifically, during the phase of developing ideas, one idea is for each innovator to return to books that were inspirational on their journey, even if not directly related to the type of idea being incubated. For example, when developing ideas related to creating a car, the innovator could return to their favorite works related to why they entered the area of car development, perhaps poetry related to technology and movement. Using these personal favorites as "guides" could help deepen the meaning of the project, and provide some contrasts to the types of readings that might otherwise be technical or required for the work. 

​For me, my first choice for an always-returnable guide would have to be "Synergetics: Explorations in the Geometry of Thinking" by R. Buckminster Fuller in collaboration with E. J. Applewhite!​

Monica: How can users use the Catechism and the Playbook?

R.J. Cordes

The great thing about Catechisms is the simplicity, you could answer the questions on your own to get a better understanding of projects you’re already a part of or you could get your team to answer them as a group to build alignment. It’s recommended you keep a common, versionable document with the questions and answers to make sure the team can always go back, but that doesn’t mean you can’t do it in a notebook. The same applies to the Playbook itself, which is full of good questions you and your team can answer to drive alignment and innovation.

Monica: Any other final thoughts?

Daniel A. Friedman

Not right now, happy to address any other questions or provide more information. Looking forward to continuing the collaboration and seeing how the IDP turns out.

R.J. Cordes

I think it’s important to remember that the Innovator’s Catechism found in the book was created as a result of someone saying “hey, the Facilitator's Catechism doesn’t really fit my discipline very well, what adaptations would make it valuable?”, and that the Facilitator's Catechism came from Daniel and I saying the same of the Heilmeier - innovation on process is still innovation, don’t be afraid to look at anything in the playbook and question how it might work for your team, for your discipline, or for your personal workflow - and change it. We’re all learning by doing, and you never know who may benefit from you sharing what you’ve learned.

About the Author

Picture of Monica H. Kang

Monica H. Kang

Monica H. Kang, Founder, and CEO of InnovatorsBox® and Author of Rethink Creativity is transforming today’s workforce through the power of creativity. She helps companies rethink culture, leadership, and team development by making creativity practical and relatable regardless of industry or job title. She has worked with clients worldwide including Fortune 500 companies, higher education, government, and nonprofits. Monica’s work has been recognized by The White House, Ashoka Changemakers, National Minority Supplier Development Council (NMSDC), and Women’s Business Enterprise National Council (WBENC). Prior to InnovatorsBox®, Monica was a nuclear nonproliferation policy expert. She holds an M.A. from SAIS Johns Hopkins University in Strategic Studies and International Economics and a B.A. from Boston University.

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