Chicago Certified LeSS Practitioner April 27-29, 2026

  James  5 mins read.

April 27-29: Get Tickets

Course Agenda

The morning of the first of three days will be used to establish the overall context of the system modeling activities which follow. This will be done through a small amount of lecture, combined with both small and large group discussions.

Once the stage is set, we will transition to thoughtful analysis of the impact of different organizational design decisions on adaptability and value delivery using system modeling. Following each incremental framework-agnostic advance in our understanding, we will map concrete aspects of LeSS into our increasingly enlightened understanding of organizational system dynamics. The system modeling brings deeper insight, while mapping this insight into LeSS facilitates better retention along with an understanding of how to act on what is being learned.

We will continue to incrementally advance our depth of understanding using system modeling for the majority of the three days. Towards the end of the third day time will be spent: coalescing the whole of our enhanced understanding; providing guidance on how to move forward; and orienting participants on how to navigate a wealth of additional information.

DAY 1: Setting the Stage

The first of three days will be used to establish the overall context of the system modeling activities which follow. This will be done with a small amount of lecture, but primarily via small and large group discussions and exercises. We’ll follow this thread through the entire 3-day event.

  • Introduction
  • Avoiding Taylorism
  • Estimates, not Commitments
  • People are Valuable
  • System Optimization, not Local Optimization
  • Discovering Value
  • Implications of multiple Product Backlogs

DAY 2: Seeing Simplicity through Systems Modeling

On the second day, we will take what we learned about Systems Modeling on Day 1 and use those tools to understand:

  • Benefits of Cross-Functional Teams
  • Product Breadth Considerations
  • Private Code Impedes Technical Excellence
  • Managing Cognitive Fullness
  • Requirement Area Sizing Considerations

DAY 3: Modeling decisions through Systems Modeling & LeSS

As we continue to advance our depth of understanding using system modeling, the third day will be spent coalescing the whole of our enhanced understanding, providing guidance on how to move forward, and orienting participants on how to navigate a wealth of additional information.

  • Product Breadth and Adaptability
  • Avoiding Middlemen
  • LeSS Complete Picture
  • Structure Drives Culture
  • Adoption in your organization
  • Extended Q&A

After course completion

Each participant will be a Certified LeSS Practitioner and will get an account on less.works. Here one can find additional information about LeSS, share course information, and stay in contact with the other course participants.

All participants get access to the book: Large-Scale Scrum: More with LeSS

U.S. Air-Force Specifics

This course is listed in the United States Air Force’s Education and Training Management System (ETMS). More details are available here.

Participant Testimonials

LeSS Adopters

LeSS Logo Sheet by Sector

Travel Logistics

Arriving By Air

Chicago is served by two commercial airports, O’Hare (ORD) and Midway (MDW).

O’Hare airport is a huge international airport with non-stop flights to almost anywhere on the planet. O’Hare is a hub for United Airlines and American Airlines.

Midway is a regional airport which is a bit closer to downtown Chicago than O’Hare. Southwest Airlines operates most of the flights into Midway.

Arriving By Amtrak

Roomette

A direct Amtrak route can be a wonderful low-stress choice for travel to and from downtown Chicago. This is especially true for anyone living in the mid-west. Only direct cross-country routes on Amtrak tend to make sense.

Detailed Travel Logistics

See the following pages for additional travel details:

Training Venue Details

I have reserved a hospitality suite at Sheraton Grand Chicago Riverwalk, 301 E North Water St, Chicago, IL 60611.

I strongly suggest you ensure any hotel room reservations you make at the Sheraton Grand Chicago Riverwalk can be canceled without penalty. To explain, there is always a chance of discovering more course demand than the current amount of reserved space can sustain. In that eventuality, the search for larger last moment space with availability can result in the course being relocated to another downtown hotel. I don’t think this will happen in this case, but it is good to remain flexible when running a public course. I am always careful to configure the ticketing system not to sell more tickets than my current event space can support; only raising the ticket count once appropriate larger event space is confirmed.

Hotel room prices in downtown Chicago tend to rise quickly. Therefore, it makes sense to reserve your hotel room early, just make sure you can cancel and relocate if needed.

Taking the Blue Line on the elevated train from Chicago O’Hare Airport (ORD) to the State/Lake station will put you within a 16 minute walk or a short cab ride of the hotel.

If you are traveling via Amtrak, you will arrive downtown at Amtrak Union Station. The Amtrak station is a 10 minute cab ride from the hotel.

Meals

I will be providing lunch for everyone. I anticipate we will eat lunch at table service restaurants within a short walk of the venue.

Printable Flyer

I have created a printable flyer for the course. This can be useful for posting in a physical break room or other similar areas. Consider adding a note to have other people in your company come talk to you about the course, especially if you are planning to attend yourself.

The second optional page of the flyer details which mid-west cities are particularly good candidates for traveling by Amtrak rather than flying. This is particularly true of Milwaukee, Minneapolis/St. Paul, Detroit, St. Louis, and Kansas City.

Tickets

April 27-29: Get Tickets