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Design & Innovation Roundtable Playbook 

Guidelines for Chicago Design & Innovation Roundtable Gatherings

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Who we are

Leaders--director level and above--with responsibility for design, digital, and/or innovation in an established organization. While “established organization” is a broad identifier, it means that the habits of design thinking and innovation are not in the founding DNA of the organization, and it has been successful for some years. This creates the double-task of leading our practices and being advocates for change more broadly in our organizations.

Companies who are quality and people-focused.

People who are known and trusted by at least one current member.

What we get

Catharsis, validation, support, ideas, access to more experiments, camaraderie, relationships, information, debates, personal life experience sharing 

Which characteristics matter for membership?

  • Decision-making responsibility and accountability at a high level in your organization.

  • Company has been established for some time (5+ years) and is mid-market to enterprise (generally 500 employees and up).

  • Open and trusting nature.

  • Active participation in storytelling.

What are our agreements to each other?

  • Attend 75% of the monthly gatherings in a calendar year. Joining the Roundtable is a commitment to the other members to peer learning and sharing, and requires consistency in the group.

  • Confidentiality and integrity.

  • Respectful communication among peers in a lightly-facilitated meeting.

  • Be generous in sharing what you know, and humble to learn from others.

  • You are never required to share company or personal information you aren’t comfortable sharing. Passing is always an acceptable practice.

  • Organizing gatherings, assistance, and even business collaboration outside of the monthly meetings is welcome.

  • No selling or recruitment at Roundtable meetings.

  • Formal invitations to join the Roundtable go through the Roundtable Lead. All members are encouraged to nominate / introduce someone who would be a good member.

Meeting Logistics

Each Roundtable has a host company assigned to coordinate that meeting. While the Roundtable previously met in host offices--and may again in the future--we currently meet on Zoom. The host collaborates with the Roundtable Lead to:


  • Confirm the meeting location, date, and time

  • Establish a focus topic for the roundtable

  • Prepare a “spotlight” presentation on their own company, team, and work

  • Facilitation of any pre-meeting homework for each company 

  • Procurement of an outside expert presenter or facilitator (if/when the group decides one is desired) 

Meeting location 

Currently via Zoom.

Meeting dates/times 

Currently monthly on the fourth Friday from 12:15pm to 1:30pm central time.

Communications leading up to the event 

The Roundtable Lead and the host are the quarterbacks for all communication leading up to the event. They are responsible for ensuring everyone knows: what’s happening, who’s attending, what homework is required (and by when), etc. While we hope all Roundtable members appear are relatively active in Slack, one or two “formal” communications via email are likely a good practice to ensure everyone receives key communications. Email is often easier to reference after the fact if you end up sending final logistics and agendas. 

Facilitation of any pre-meeting homework for each company 

We’ve often ask Roundtable members to share experiences and insights related to the focus topic, or bring a particular challenge or success to the group. These can be shared in advance via a Google doc or sheet. Past questions have include:

  • Updates, what’s been going on?

  • Biggest accomplishment since last meeting?

  • Most significant learning since last meeting?

  • Highest priority for next 6 months?

  • What would you like help from the group on?

Lightly facilitate meetings 

By default, the Roundtable is lightly facilitated by members and the Lead. Assuming there is not an outside presenter or facilitator, someone from the host company should plan to provide the light facilitation required for the “standard” Roundtable meeting. 

Facilitation works as follows: 

  1. Introductions (if needed) and updates since last meeting

  2. A “spotlight” readout on the host company and team

  3. Framing up the focus topic of conversation for the month

  4. Lightly directing the conversation to ensure many voices are heard

  5. Wrapping up: sourcing possible focus topics, voting on next month’s topic, and selecting next month’s host.

Interested in being a part of the Design Thinking Roundtable? Contact Highland President Jon Berbaum to learn more.