How to Conduct a Successful Retrospective

I think we all have been sitting in a meeting and thinking that it’s a waste of time. While most of our meetings have now been done online, keeping the focus and engagement is even harder than before. Over time, after analyzing customer meetings and our own meetings in Weekdone, I have come to some conclusions about how to run useful retrospectives. Even though most of those learnings are based on OKR retrospectives, I have found those simple principles useful during any kind of meeting.

If you are wondering why should you even have retrospectives, I would like to know how else will you analyze and learn from the past together as a team or company to make better decisions in the future?

“The ability to learn faster than your competitors may be the only sustainable competitive advantage”

Arie De Geus

How do conduct valuable meetings that don’t feel like a waste of time?

Learning starts from the right mindset

You only learn if you are ready to learn. That means there has to be an open and learning-oriented culture in the team and in the company in general. People have to be able to admit their failures without being afraid of being strongly criticized. Achieving this culture takes time and trust in the organization.

There’s a huge difference between criticism and constructive feedback. Criticism is just looking back and pointing the finger, repeating that the person has failed, and just making them feel bad about it. Constructive feedback or even constructive criticism is about looking into the future, what do you see that the person could do better next time and how? What ideas and support could you share to help that person to achieve it? What would you do differently and why?

What you need is not to blame someone but to figure out how everyone could avoid such mistakes in the future.

Plain criticism is not welcomed but constructive feedback needs to be given and it needs to be accepted by the receivers. It’s not about WHO’s idea is best but WHICH idea is the best for your organization. People have to be able to admit that “well I thought this will work but it didn’t”. It’s fine! You just need to try something else and it’s important to stop when something isn’t working. And as T.Edison said, “I’ve not failed. I’ve just found 10,000 ways that do not work”. Finding things that do not work for your company is also progress if you understand why they didn’t. It’s gained knowledge!

Opinion or feedback doesn’t follow the power hierarchy. The opinion is a point of view that is generated based on the role we are and what kind of past experiences and knowledge we have to analyze the situation. The power hierarchy just changes from which angle the situation is experienced but not the value of the opinion. The same goes for feedback. Each feedback and opinion is valuable if it’s backed up with facts and can be explained. People need to feel safe to share their opinions and honest feedback. That means their answer can’t be later rejected based just on their position or even worse their job can’t be threatened if they say honest things that maybe managers do not want to hear. To learn, we need to be ready to accept the feedback no matter where it is coming from.

To get valuable answers you need to ask the right questions

It’s hard to evaluate anything if you do not know what you are supposed to look for. If you ask the right questions that nurture people’s thinking, you might learn many interesting things. We will give you some questions for different purposes, you can find them below. You do not need to answer them all, choose what is relevant for you and what clicks in your people’s minds.

Keep in mind that answers need to be discussed! When we say it out loud, it requires us to think our sentences through and formulate the answer that we are planning to give. Already in this process, we actually evaluate and analyze a lot more than when it happens just in our head.

Discussion is important because we all evaluate the same situation from different angles based on the knowledge and experience that each individual has. More opinions mean that we are able to get a deeper and fuller understanding. By discussing our points of view we can connect the dots between different things and make conclusions about why something has happened or what might influence it. Remember, it’s constructive feedback and not just judging people’s opinions. At the end of the discussion, the group should agree on common learning points.

Here are some examples of questions you can ask during an OKR or some other retrospective:

Questions about the process

  • How did the team generally perform? What did we achieve?
  • How was the quality of the OKRs (goals) that were set? Did they help the team make some improvements?
  • Did we prioritize our goals enough? Were people working on them?
  • Were people aware of the roles and responsibilities they had? Did they feel that they knew what to do?
  • How often did we discuss the progress? Did we have enough regularity and consistency?
  • How can we be better at setting goals next quarter? What do we have to keep in mind?

Questions about success

  • Why were we successful with achieving the Objectives?
  • Was it intentional or did it just happen?
  • What kind of actions brought the highest results?
  • Are there things that we can improve even more?
  • Can we use what helped us succeed in some other areas as well?
  • What are the key takeaways from our success that we can share with others?

Questions about failures and challenges

  • If we failed, then why? What did we try and why do we think it didn’t work?
  • Most likely something did fail. If it wasn’t the desired result in general that we missed, it was some kind of action that didn’t bring any results. So, what doesn’t work for our team/company?
  • What were the major challenges?
  • Why did those major challenges appear? Can we prevent them in the future? How?
  • What kind of knowledge or experience might we be missing? How can we gain it or did we already?

Questions about the future

  • What are the key things we learned and have to keep in mind while making decisions in the future?
  • What kind of new opportunities have we noticed?
  • What should we as a company or a team start doing? Or what should we continue doing?
  • What should we stop doing?

As a summary, remember to have an open and honest but respectful culture, share constructive feedback, ask the right questions, and have valuable discussions to complement the answers.

And if you are wondering what animal is the OKRs I have been mentioning, then I personally believe it’s the most logical and successful goal-setting framework. It’s used to drive innovation, growth, and improvements. If you are interested, you can learn more here.

Originally published at




OKR coach. I am interested in how businesses work and how to help them to improve. Writing about OKRs and other related topics.

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Mirell Põllumäe

Mirell Põllumäe

OKR coach. I am interested in how businesses work and how to help them to improve. Writing about OKRs and other related topics.

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