Insider tips for Agile retrospectives that make a difference

Written by Rina Nir

Culture is like the wind.

Rina Nir


Jun 14, 2024


For Project & Product Managers


From the Harvard Business Review, a wonderful quote about culture: “Culture is like the wind. It is invisible, yet its effect can be seen and felt. When it is blowing in your direction it makes for smooth sailing. When it is blowing against you, everything is more difficult. “(by B Walker and S Soule). K15t has culture blowing in their direction and propels them to Atlassian Marketplace greatness. I discovered that Agile retrospectives is one of the strong winds pushing their ship ever forward.
In my quest for retrospective wisdom, I sat down with with Anshuman Dash. Dash is the COO at K15t and one of their facilitators. What struck me was how ingrained feedback loops and retros are in their culture. To illustrate their importance, K15t has historically encouraged Dash and others to participate in intensive facilitation training programs. The investment is significant, often taking key leaders like Dash out of their daily work for weeks in order to hone their facilitation skills and integrate their learnings back into the company. In addition to retrospectives, they learn how to facilitate change and transformation at every level and context of the organization, from quarterly team retrospectives to new innovation exploration at company Team Weeks.

10 tips for successful  retrospectives

With such a wealth of knowledge and experience, Dash had some tips to share. I condensed his advice into ten highlights.

  1. Team size: 6-8 people is the sweet spot for an effective retrospective.: To leave an impact and make great change, you need everyone’s voice to matter. A group of 20 is not going to make for a good retro due to time and attention span limits. Need a reminder for the perfect size? Follow Jeff Bezos’ two-pizza team rule: “We try to create teams that are no larger than can be fed by two pizzas.”
  2. Create agreement early on: As Neal Taylor mentioned, setting the stage is critical. Dash suggests that the retro opener should also include an agreement on tshared guidelines. Be respectful, let everyone voice their opinion, we can take breaks if things get too difficult, and so on. As needed, the facilitator invokes this agreement, to get us over any bumps in the road.
  3. Everyone needs to be heard: Retrospective should avoid the trap of group thinking, or the trap of letting the loudest voice dominate. Introverts or newbies may come up with the most useful insights and we desperately want to hear them. The agreement (see above) sets the scene, but it’s the facilitator who creates the space and the atmosphere to ensure we hear these voices.
  4. Allow time for self reflection: Retrospective playbooks call for prompting the team. The classic one, is to ask the team: “What went well? What could have gone better? hat we should stop?”. The key point here is to give some time to ruminate. Don’t rush people to fill their post-it notes. Some of the best ideas take some time to emerge.
  5. Don’t shy away from difficult conversations: Even with the best teams, friction is natural and interpersonal dynamics can affect productivity. As a facilitator, do not run away from these situations. Your job is to help the parties work out their differences and help dissolve the tension. Key is to let everyone be heard. Sometimes this means a pre-retrospective 1-on-1 meeting with each person. This ensures that people know that the facilitator is fully informed and also that they have had a chance to talk things over. During the retro itself, if tension is high – it’s ok to take a break, even for several days. Convene again when people have had a chance to reflect and calm.
  6. Train the facilitator: Dash still remembers how his training helped him shift his state of mind and attitude. He says: “The majority of the workshops were about building yourself as a tool for facilitation. How do you create that environment where others can feel safe and would freely share? How do you ground yourself in difficult situations?”
  7. Make retrospectives fun. It helps people fully arrive at the retrospective, and turns it into something people are looking forward to. Watch the video to hear about one cool example of a game some K15t teams use. (video)
  8. Be careful not to turn retrospectives into the only place where challenges are discussed. If John thinks that Monika needs to prepare Jira Stories better before assigning to him, he’d better bring it up with her. That may lead to immediate improvement and could be kept out of the retro.
  9. Real data can drive better insights. At the stage of bubbling insights, it’s good that people have solid data to reflect upon. For example, a Jira Snapshots table on a Confluence page (link to, can show people how their pre-sprint intentions worked out. How did the scope change and what eventually was delivered, or to quickly identify the worth noting stories in the Sprint
  10. An agile retrospective is only as good as the actions and follow up. Capture the actions in a way that is visible and that is easy to integrate with the day to day work. It’s handy to capture actions on a Confluence page. Action owners can update the status as they make progress on actions. Putting everyone on the same (Confluence) page.
a Jira Snapshots table on a Confluence page can show people how their pre-sprint intentions worked out

a Jira Snapshots table on a Confluence page can show people how their pre-sprint intentions worked out

A few last words

These gems of experience can provide a blueprint for better retrospective. But Dash’s most important point is underpins all of this. In his own words: “Just trust the process. Retrospectives, are a great way to collect feedback and then improving on it. Retro after retro, week after week, month after month, quarter after quarter. I have seen it happen time and again, turning teams into a well-oiled machine. Even for the skeptics: Get in there. Once you’ve created the space, just trust the process, follow the basic structure and the best practices. You’ll see, it will help.”

Trust me, this is solid advice from an insider.


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