Hi everyone - after a small hiatus, I’m back with another post to share how we run CS Ops internally at Gainsight. If you missed the first post, you can check it out here. I discussed how we run our quarterly planning and sprint processes. Today, I’ll be discussing one of my favorite tools to foster learning within our team - Retrospectives!

In the ever-evolving landscape of customer success, staying ahead means continuously adapting and improving strategies and operations. Incorporating regular retrospectives into your CS Ops team can help achieve this goal. These retrospectives foster teamwork by providing a space where team members can share without judgment and find common ground in their work.
 

Why Retrospectives are Valuable
 

Retrospectives foster a culture of continuous improvement and teamwork. Through regular check-ins, teams can analyze what worked well, what didn't, and formulate action plans for the future. This not only promotes efficiency but also nurtures a more collaborative and transparent work environment.

There are many different types of retrospectives that can be incredibly valuable:

• Sprint Retrospectives: While not a primary focus of our internal operations team, we do make an effort to share one thing that worked well and a learning point at the end of each sprint demo.
• Project Retrospectives: These are valuable after large projects, whether they went really well or off the rails. Learnings can be found in both successes and failures!
• Quarterly (or Interval) Retrospectives: These are my favorite, and they will be the focus of this post.

Quarterly Retrospectives

• Timing: End/Start of Quarter, 1-2 sessions
• Audience: Direct reports and/or cross-functional teammates
  • For our retros in customer success operations, which includes Gainsight Admins, our enablement team, and support operations.
  • We plan to include our entire post-sales operations team on a less frequent basis in the future.
• Format:
  • Icebreaker (15 min)
  • Reflection (20-30 min), typically 2x/year
  • Retrospective Exercise (45 min to 1.5 hours)
• Setup: We usually conduct our retros virtually using Miro to facilitate the meeting. Miro offers a range of great templates to get started or to create your own!

Reflection

During the reflection session, we ponder over four questions to get the team in the right mindset for what follows:

• What are you most proud of?
• What impact have we been able to deliver?
• What did you not accomplish this past year but wish you could have?
• Which people or teams have assisted you in achieving your goals this year?

Retrospective
We've utilized various retrospective formats in the past - “Start, Stop, Continue,” “Rose, Bud, Thorn,” “Keep, Problem, Try” - all very similar, with “Start, Stop, Continue” being the most successful in my experience .

Each teammate gets assigned a virtual “sticky” color and can add comments to others' feedback. We attempt to group similar feedback to maintain an organized board.

Here’s an example of a retro our team completed a few years ago (easier to read than some of our bigger boards . It’s exciting to see the changes we’ve implemented over the years that started in these discussions!

Low/High Feasibility & Low/High Impact Scale
We wrap up the session with “dot voting” where each teammate gets three dots to vote on the most impactful ideas in their opinion. We then chart the top-voted ideas on a graph, pinpointing those that are feasible and high-impact to select the highest impact with reasonable feasibility. Individual owners are assigned to these top choices, which then find a place in our roadmap planning for the following quarter.

Tips for Effective Retrospectives

• Be Constructive, not Critical: Foster a positive setting encouraging open sharing sans fear of backlash.
• Actionable Insights: Steer discussions towards actionable insights rather than just scratching the surface.
• Document Findings: Consistently document the findings and decide on the feedback to be incorporated in a roadmap for future improvements.
• Have fun!: Remember, this is a chance for the team to bond in a relaxed setting. Perhaps play some music while the team brainstorms to keep the energy upbeat!

I’d love to hear more about what type of processes you’re leveraging internally to build an environment of constant learning and improvement!