How to do Retrospectives That Don’t Suck

Let’s be honest: many retrospectives can feel uncomfortable, like a waste of time, or just generally “Meh”. Maybe your team goes through the motions, complains about things they can’t change, or sits quietly while a few dominant voices steer the conversation. Or maybe your retros are working—You are tweaking the process, tracking metrics, and trying to keep the process running smoothly—but it still feels like the ROI of time investment isn’t there, or you know the team are not tackling the real issues.

If you are the one facilitating, you’re probably dealing with the tension between knowing retros can be powerful but you may be experiencing them as dull, frustrating, or the team are just tolerating the meeting. If so, it probably looks like that time would be better spent on “real work.”

Consider: There Are 3 Levels of Retrospectives

Level 1 retros are the ones nobody likes doing. They may be dysfunctional, lifeless, or just not that beneficial, and they generate little insight or energy. This is where most people give up and cancel the meeting, or they agree to do it every other sprint, or once a quarter, or annually–And who can blame them?

I recommend aiming for Level 2, where the retro becomes a structured review of the system of work. The team takes an impartial, objective, and empirical (evidence-based) view of the process–a bit like acting as scientists–reviewing data, forming hypotheses, and running experiments to improve how they deliver. This can create steady gains—But beware of becoming complacent. Over time, even a level 2 retro can flatten into a boring level 1 ritual.

Practical Steps to move from Level 1 → Level 2 (Make it Worth Doing):

1. Make the purpose clear: Start every retro by reminding the team why you're here: to learn from what happened and improve how we work together.
2. Timebox complaints: Acknowledge frustrations, but steer the team toward what’s actionable. Ask: Is this within our influence? What can we experiment with next sprint?
3. Use structure: Rotate formats (Start/Stop/Continue, 4Ls, Timeline Retros, etc.) to keep things fresh and guide focused discussion.
4. Equalize voices: Use silent writing (e.g., sticky notes or online boards) before open discussion. Try round robins so everyone speaks at least once.
5. Work to create alignment, not agreement: It is not necessary that everyone on the team agrees with exactly how to solve problems (or even what the problems are in the first place.) But it is important that team members be willing to support and empower the direction that is chosen, however that is decided. If you are acting as a scrum master or manager, you may be able to cast a deciding vote, but try to get the team to dwell in the facts and data, while giving space for experience, intuition and interpretation.
6. Track and follow through: Pick one or two concrete actions and check in on them next retro. Visible progress builds credibility and trust in the process.

What’s Beyond Level 2

Maybe you’re already doing something that sounds like Level 2. If so, great! But there’s more juice to get out of this recurring meeting.

Level 3 retros are focused on the human aspect of the process, especially communication and experience. In addition to optimizing the system of work, a level 3 retro is intended to cultivate the phenomenon of “teamwork”—as a living, committed, complex group of humans.

At this level we are acknowledging that the team members not only perform the work, but they have an experience of the work, which impacts and shapes performance. If the experience of the work is “great” then you’ve got nothing to worry about. But when the experience is dull, draining, frustrating, anxious, stressful, overwhelming, etc. and if that is never discussed, then it’s likely that this less-than-optimal experience can get “stuck” with people–leaving them disempowered, frustrated, and “alone”--having to just “get by” week after week in survival mode.

A level 3 retro is a space where team members can express what was hard, what didn’t work, what they hope not to deal with again (or at least not deal with all by themselves.) Maybe the team wants to put something in place to prevent the same thing happening in the future—maybe not—but most importantly the team and team members are heard, known, and given the space to let that stuff go and move on. The retro can also be–and probably should be–a place where the team can be acknowledged and “known” for their specific contributions and accomplishments in the previous sprint.

At this level of retro, the goal shifts from just improving output to building trust, connection, and safety. The most valuable thing that can happen in a retro like this might not be a clever process tweak—but a breakthrough in communication, which might look like a moment of honesty, where someone shares what they’ve been holding back, and the team leans in rather than getting distracted or resisting. I’d like to suggest what limits performance is not merely process and knowledge, but the quality and strength of relationships on the team. A level 3 retro is working on the level of relationship building.

Practical Steps to move from Level 2 → Level 3 (Mature as a Team):

• Actually Listen to Who is Speaking: There is a culture in tech companies that working on other things and responding to slack while in meetings is not only normal and OK, but advisable and necessary. There’s lots of reasons for this, but if there’s one meeting where I recommend that you do nothing else but be present with what people are saying, that’s a level 3 retrospective. You might request that people mute their slack, and not work on other things for this meeting. If there’s a deadline, or a shit-happens, or something that is more important than focusing on the retro, encourage them to excuse themselves and go handle that thing, even if they think they can multi-task. Otherwise, request that the team be fully present and that they give each other the respect of listening to what is being communicated.
• Make Sure People are Acknowledged: In addition to brainstorming “what what well and what didn’t” have one of the categories be “Kudos” or acknowledgements, and START with this section during the open discussion. Make sure the team gets the space to acknowledge and celebrate each other. Especially when you start the conversation with acknowledgement, you will find that it lightens the mood and creates the necessary level of relatedness to get into more difficult conversations about what’s not going so well.
• Create emotional safety: Open with a simple check-in (“How’s everyone doing?”). Model vulnerability yourself as a facilitator. Keep communication informal (being overly formal can inhibit freedom of communication.) Allow people to participate at the level that is comfortable to them. Encourage authentic participation while respecting boundaries. If you are everyone’s boss, consider nominating someone else as facilitator (make sure they are willing and up to the task of facilitating a conversation where their boss is one of the participants).
• Ask human-first questions: Not just “What didn’t work?” but: “What was hard about that?” or “What are we not saying that might be useful to say here?”
• Listen for what's not being said: Pay attention to body language, silence, or repeated patterns. Gently invite quieter voices in: “<Person’s Name> Anything you’ve been sitting with or anything you want to share?” Give space for unexpected contributions–Ask: “Is there anything else you want to say about that?”
• Ensure to facilitate and name dynamics: If certain people always speak first or dominate, call it out respectfully. “Hey, I noticed that we’ve heard a lot from you in this session, let’s make sure others have a chance to contribute their thoughts.” If that person is you, try doing a retro where you ONLY facilitate and don’t act as a participant. Tell the team what you’re doing, so it’s not weird.
• Celebrate courage: When someone shares something real, vulnerable, or risky, thank and acknowledge them. That might sound like: “Hey, thanks for sharing that difficult/vulnerable/unpopular take–I got something out of what you said.” Even if it’s tough to hear, that moment can make the team stronger if handled gracefully.

Sort Yourself Out Before the Call: If you are having a bad day, are upset about something (work related or not), or are otherwise not in the frame of mind to deal with what could be tricky conversations to facilitate, prioritize taking care of yourself. Drink some water, have a nap, touch some grass - but be proactive, because whatever is going on with you as facilitator is going to be the emotional backdrop of the conversation.

Bringing It All Together

Start with intention. Make space for the human side of work. And expect big returns on this investment over time. Look for things like alignment, stronger relationships, and meaningful progress on work that had been stagnating and stuck— this is worth far more than a few tweaks to a Jira workflow.

What level have your retro’s been? What are you shooting for now? Let us know!