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.

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.”

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.

Digital Trailblazers!  Join us Fridays at 11am ET for a live audio discussion on digital
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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 

4. 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. 
5. 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.

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.