How DevOps and Agile Team Leaders Can Organize a Successful Workshop

I’m a strong proponent of hybrid working.

Requiring a strict in-office presence can be hard on many employees with long commutes, family caretakers, or people with physical disabilities. The collaboration needed by Digital Trailblazers, especially ones leading DevOps and agile teams, is rarely achieved by jumping from meeting room to meeting room or expecting people to develop meaningful relationships at the water cooler.

Sacolick, StarCIO Agile DevOps Workshops

During the pandemic years, DevOps and agile team leaders had to adjust their collaboration practices to support remote work. I’ve previously written about how to conduct remote sprint reviews and retrospectives and other tips for hybrid work for agile and DevOps teams.

Today, Digital Trailblazers must be more strategic about collaboration and decide why, when, and how to organize in-person and hybrid meetings. Executives and leadership groups often do this through workshops and offsite meetings to bring people outside their day-to-day responsibilities and focus on collaboration, problem-solving, and decision-making. Digital Trailblazers, especially DevOps and agile team leaders, should consider workshops as a critical tool to enable hybrid work while empowering team and cross-team collaboration. 

Why DevOps and agile team leaders schedule workshops 

Am I alone in this belief that in-person meetings and workshops can help Digital Trailblazers accelerate transformation and improve collaboration with DevOps and agile teams? I’m not!

“As with many engineering teams, in particular, many of our engineers are hybrid or fully remote and, with that, comes a separate set of demands, so it’s important to get the balance right on in-person meetings,” says Naggi Asmar, chief engineering officer at Matillion. “Ultimately, hybrid and remote team leaders must be agile and willing to adjust their leadership style to best fit their employees’ needs. Whether developing better communication, improving collaboration, or being more intentional with face-to-face time, businesses must be open to adjusting their approach to accommodate today’s global workforce.”

Here are several reasons to schedule workshops:

1. Channel emotions toward creative collaborations

“In the realm of hybrid work, mere office presence is not the same as meaningful collaboration,” says Marko Anastasov, co-founder of Semaphore CI/CD. “Do gatherings reignite passion, synergy, and innovation?”

In other words, workshops can help teams raise their emotional intelligence (EQ) and drive creativity – two key elements needed to drive innovation, and that’s often less effective when done on Zoom, Microsoft Teams, or through the drudgery of in-office meetings.

2. Realign organizations on mission and goals

There are good reasons why sales organizations schedule at least a once-a-year gathering. Digital Trailblazers should also consider yearly offsites, full-team get-togethers, and workshops aiming to align on yearly objectives.

 “To build a great engineering culture, the entire team should get together once a year for at least three days,” says Jim Gochee, CEO at Blameless. Use this time to align on shared goals, to educate and train, and to build connections. I’ve successfully used this approach for over a decade.”

StarCIO Vision Statement Template

For medium and large enterprises, CIOs, CTOs, and CDOs should consider gathering the entire DevOps and agile team organization to create meaningful self-organizing standards, discuss learning objectives, and review vision statements of digital transformation objectives.

3. Solve problems and improve communications

Grant Fritchey, product advocate at Redgate Software, shared several reasons you might want to schedule workshops and offsites to address common challenges facing DevOps organizations and agile teams.   

  • When making the initial social shift necessary to DevOps, an offsite helps the team establish a newer, better means of communication. 
  • If you attempt to move your established processes into new technologies, an offsite where people can focus and brainstorm may also be useful. 
  • If you suffer a major outage or problem with your process, an offsite as a way to understand what went wrong and how to fix it can benefit from the focused, face-to-face communication that being away from the office can provide.

Plan the workshop: Agenda, attendees, and homework

At a recent Coffee with Digital Trailblazers, a LinkedIn audio event I host on Fridays at 11am ET, we discussed several best practices for organizing offsites and workshops. Executing a meaningful workshop where people walk away with deeper relationships and the group solves key problems requires planning.

Coffee with Digital Trailblazers hosted by Isaac Sacolick Digital Trailblazers!  Join us Fridays at 11am ET for a live audio discussion on digital transformation topics:  innovation, product management, agile, DevOps, data governance, and more!

  1. Define an agenda – Speakers at the Coffee Hour recommended identifying the desired outcomes and then working backward to define the approach. What decisions are needed? What problems do you want attendees to focus on and aim to solve? What types of relationship-building are useful, especially if people can’t meet frequently?
  2. Identify the attendees – Do you want a wider audience so that more people are part of the process or fewer to drive more efficient decision-making and problem-solving? There are a couple of schools of thought, whereas some agendas require a more inclusive group, and others benefit from collaboration by a specially selected team. The workshop organizers should discuss and agree on an approach.
  3. Assign responsibilities – Organizing a workshop requires one or several people with the following responsibilities:
  • Sponsor - to finalize the objectives and target outcomes
  • Agile project manager – to oversee the timeline and deliverables by the meeting organizers
  • Logistics organizer - to select the location, invite attendees, handle travel, plan for meals, and manage other event logistics
  • Content coordinator – to create a program that aligns with the objectives and outcomes
  • Facilitator – to run the workshop and lead collaborative discussions
  • Supporters – to “read the room” and recommend any changes to the agenda and to take on smaller table/team-level facilitation roles
  • Scribe – to capture parking lot items, decisions, and follow-ups 
      Digital Trailblazer by Isaac Sacolick
    1. Create attendee materials -  This should include work attendees must do before the workshop, such as required reading, data analysis to ground the discussion, and presentations you expect people to make. A best practice is creating a post-workshop checklist for attendees and teams to follow up after the event. 
    2. Review the plan – Even though responsibilities are assigned, the planning team needs to coordinate on meeting location, agenda, communications, and who’s doing what at the event. Consider what materials you need at the meeting, including screens, mikes, and whiteboards, and whether you want attendees to use their laptops or phones. Another question to resolve is whether you are hosting an all-in-person or hybrid event where some people can attend remotely.

    During the workshop: What to look for and when to pivot

    The best well-laid plans should be open to real-time adjustments and pivots. Below are twelve considerations:

    1. Are there unforeseen logistic issues that require some adjustment to the agenda?
    2. How will you adjust the agenda when bad weather impacts your plan or when really nice weather distracts attendees? 
    3. Was the agenda too ambitious, and do people need more time to work through the program?
    4. Were enough networking breaks scheduled, or do you want to extend the networking time?
    5. Does it look like people are learning and enjoying themselves, or should you step back from the business agenda and focus more on the attendees’ needs? 
    6. How will you champion the best ideas, contributions, and behaviors to influence others?
    7. Are conflicts becoming overwhelming, and should the organizers table stressful discussions for another time, place, or smaller group?
    8. Who’s responsible for reaching out to quiet participants or silent detractors who aren’t participating? 
    9. What is your plan if an attendee becomes unruly and distracts the group from the agenda?
    10. What happens if a leader elects to “pull rank” to control the conversation? 
    11. Who takes charge to ensure a positive outcome if there’s a blow-up moment?
    12. Who decides how to handle a crisis that may require a major pivot or cancellation of the workshop?

    After the workshop: Keys to success are in the follow-ups

    Here’s where workshops miss the mark:

    • The organizing team doesn’t regroup and conduct a retrospective.
    • Communications on decisions are emailed but not recorded in platforms to share with wider audiences and institutionalize.
    • Follow-ups are emailed but never recorded in the platforms used by teams and attendees to track progress.
    • Post-event checklists are distributed to attendees, but the timeline and responsibilities for reviewing them aren’t in place. 
    • Leadership-level communication is an afterthought; they’re left wondering whether the event was valuable to attendees and delivered on promised outcomes.
    • There’s little discussion on when, why, and how to follow up on the next in-person gathering.

    Bottom line: Big offsites and workshops are expensive and are outliers to standard meetings. Significant good can come from them, but the value is in the follow-ups. The to-do lists and decisions need to be folded into the appropriate tools to ensure that short and longer-term actions aren’t lost in emails and documents.

    If you need help organizing your offsite or workshop, let me know, and please review our Driving Digital Workshops.

    Isaac Sacolick
    Join us for a future session of Coffee with Digital Trailblazers, where we discuss topics for aspiring transformation leaders. If you enjoy my thought leadership, please sign up for the Driving Digital Newsletter and read all about my transformation stories in Digital Trailblazer.

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    About Isaac Sacolick

    Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.