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The old saying goes that insanity is doing the same thing over and over again, and expecting different results. And this is, unfortunately, what happens in a lot of organizations.

There’s a specific way of doing things that everyone’s used to, and it feels too cumbersome to challenge the status quo, even if it’s not the most efficient process.

That’s where sprint retrospectives come in. By pausing every sprint to look back and ask “hey, what worked this sprint? What should we change?”, you’re encouraging conversations and action that will ultimately make your team more effective and efficient.

But, like any meeting, there are challenges to be cognizant of when conducting sprint retros and best practices to ensure no one’s time is being wasted. In this article we’ll look at:

What’s a sprint retrospective?

Let’s start at the beginning. For those who are new to the concept of agile teams and the scrum methodology , a sprint is a defined period of time to complete a set amount of work. Usually, sprints range from 1-4 weeks. At Hypercontext, we run weekly sprints for our engineering team and bi-weekly for our marketing team.

A sprint retrospective is a type of agile meeting that happens at the end of each sprint. Its purpose is to review work that’s been accomplished, what wasn’t (and why), blockers, scope creep, and to identify what’s working and what’s not. Scrum Masters or Engineering Managers will then use that information to help inform the next sprint.

But remember, the goal of this meeting isn’t to live in the past. In fact, it’s quite the opposite. It’s to learn from challenges, like recurring blockers or inefficient processes, and apply those learnings in the future.

While sprint retros are more commonly used by software development teams running agile meetings, the concept can be applied org-wide. The importance of stopping regularly to reflect on what’s been done and how to move forward is true for all teams.

The benefits and challenges of running sprint retros

Below, we review the challenges of sprint retrospectives and the benefits of overcoming them.

Challenges of a sprint retrospective

1. Lack of follow-through

As mentioned earlier, the purpose of this meeting is to identify learnings and put them into action. If nothing’s done after the discussion, there’s really no point in having the meeting, to begin with. Make sure you take meeting notes so you don’t forget about what decisions were made, and hold everyone accountable by assigning action items after each meeting.

2. Dwelling on the past

While the sprint retro is meant to review the past sprint period, try not to dwell on things that didn’t go well. Or, worse, spend this time playing the blame game. Doing these things is a waste of everyone’s time and you’ll quickly find yourself in “this meeting should have been an email” territory. Instead, acknowledge what didn’t work, come up with solutions as a team, and course correct.

3. Not enough time

Everyone has a busy schedule, and sometimes it’s difficult to stop for a second to reflect. This is especially true when you’re taking away valuable time from individual contributors on your team. Instead of writing code, they’re spending that time in a meeting. Use that hour wisely.

Feeling like you don’t have time to add another meeting to your calendar is a common challenge of sprint retrospectives. But, your sprint retro is an opportunity to recognize wins and understand what’s not working so you can adjust your actions. This will ultimately save your team a lot of wasted time and frustration. That’s why it’s essential to make them a habit.

Benefits of a sprint retrospective

The reason why so many development teams have overcome the challenges listed above is that they’ve also seen the benefits listed below. With regular sprint retro meetings, your team can:

1. Identity issues early

By taking the time to review your work and processes at regular intervals, your whole team’s ability to come together to identify issues at the very start, before they have time to spiral.

Without these recurring touchpoints, it’s harder to flag small issues. Your team may second guess whether it’s worth calling a meeting or sending an email over a minor problem. But molehills can turn into mountains and, with a recurring retro, there’s an easy opportunity to nip issues in the bud early.

2. Iterate, iterate, iterate

The Agile framework is all about constant iteration. Just because you set out to do something at the beginning of the quarter, doesn’t mean you should continue to work towards that if it doesn’t make sense. There may turn out to be a better way to reach your goals. By meeting every few weeks to review your sprints, your team has the opportunity to re-evaluate and re-adjust regularly.

3. Create a culture of feedback and accountability

Creating a culture of accountability is incredibly important for your product and for your company culture. Running a sprint retrospective, and using the agile methodology in general, helps foster a sense of accountability and ownership.


With consistent check-ins to review work that’s been done, everyone on the team has a clear line of sight into how the work they’re doing impacts the bigger picture. It drives a greater sense of ownership and accomplishment across every individual on the team. Plus, these conversations are great for keeping the team aligned on what’s expected of them in the long term and within that next sprint.

4. Facilitate collaboration

Two brains are better than one. Sprint retros provide the opportunity to review what may have gone wrong and brainstorm how to remedy it together. It’s also an opportunity to continually find better ways to work together to optimize team performance. Effective team communication doesn’t happen magically. It needs to be consistently worked on, and the sprint retrospective is a perfect opportunity to do so.

Some questions you can ask to facilitate feedback from the team include:

  • What should we start, stop, and continue doing?
  • Is there anything that would be productive for me to re-explain to our team?
  • What’s a problem we have on our team that I might not know about?
  • How could we improve cross-functional collaboration at our company?

Tips for how to run better retrospective meetings

While what works for one team may not work for another, there are a few core best practices that should be followed in every sprint retro:

1. Use an agenda

Using a collaborative meeting agenda is a best practice for every productive meeting , and the sprint retro’s no exception.

Sprint retro meeting agenda
Sprint Retro Meeting Agenda

The role of the agenda is two-fold.

First off, it helps keep your meetings on track. We’ve already identified that dwelling on things gone wrong is one of the greatest challenges of sprint retros. Having an agenda set up in advance, with clear time allocations and items that need to be covered will help keep the meeting on track and focused.

Second, an agenda allows the whole team to show up prepared. When everyone can see what’s being discussed and can add to it ahead of time, it’ll allow you to make the most of the hour you have together. No circling back is required.

2. Assign next steps and follow-through

It’s important to document everything in your meeting notes and assign the next steps. That way, when it comes time for sprint planning , you’ll have more information to work with, based on what worked (and didn’t) in previous sprints.

Sprint planning template
Sprint Planning Template

The biggest mistake you can make is thinking you can remember everything without writing it down. Humans are forgetful by nature! Make sure you take notes during this meeting, so you can easily refer back to them.

What’s more, identify who’ll be responsible for next steps and assign a timeline. It’s all about accountability.

Pro tip: Assign next steps to one individual to avoid confusion or moments where people assume someone else is working on things (and then nothing gets done). You can apply the Directly Responsible Individuals (DRIs) accountability framework to your team.

3. Use the right tools

You’re likely running your sprint retrospective virtually or as a hybrid meeting, which can pose some new obstacles. At the beginning of 2020, McKinsey reported major challenges remote agile teams faced, including:

  • Difficulty driving complex problem solving with content-heavy whiteboarding
  • Presentation issues when sharing content
  • Decentralization as a barrier for dynamic communication

But these obstacles can be overcome, with the right tech stack. Here are some tools to consider leveraging for your sprint retros.

  • Video conferencing tool: Unless your whole team’s working in the office, you’ll need a video conferencing tool to run your sprint retrospective. By now, you likely already have a video tool you’re partial to. In case you don’t, some commonly used ones include Zoom, Google Meet and Teams.
  • Collaborative agenda: A meeting agenda is essential to a successful meeting. You can go the more old-school Google Docs route, or try a meeting agenda software like Hypercontext to run collaborative, organized, and focused meetings.
  • Project management tool: While you won’t use your project management tool to run your sprint retro, it can be helpful to pull it up to reflect on what’s been done over the course of the last sprint and make notes for the next. Some popular tools include Asana or Jira.
  • Whiteboarding tool: With tools like Miro , you can document results and key processes, then embed live boards into your favorite project management tools and wikis. This will make planning for future sprints easier.

5 Questions to ask in a sprint retro meeting

To help structure your sprint retro meeting, here are 5 questions you can add to your sprint retrospective meeting agenda .

1. What did you work on this sprint?

This is a great question to open up the meeting with. But the answer should be more than just telling, it should be showing. Take this as a time for each team member to demo their work.

After each demo, get buy-in from the rest of the team. Is there anything that needs to be changed or reiterated for the next sprint?

2. What anchors are holding us back from achieving our greatest work?

On the Hypercontext software development team, we like to use the Sailboat Framework to facilitate this discussion. This is the time to uncover blockers that held you back from soaring the last sprint. We tackle two things during this agenda item:

  1. Rocks (risks): What are our potential risks and obstacles?
  2. Anchors (delaying issues): What’s caused us major bottlenecks or has inhibited our progress?

Try to encourage everyone to contribute to this discussion.

3. What’s propelling us forward?

Carrying on with the sailboat theme, what’s pushing your team forward? In other words, what worked well last sprint that you should make an effort to continue to do in the weeks to come.

Once again, try to encourage the whole team to add their thoughts. One way to do this is by asking everyone to share one thing that went well.

4. What are the icebergs on the horizon?

If the Titanic is the first thing that comes to mind when you think of icebergs, you’re not alone. But icebergs don’t need to be disasters. They can also be beautiful! What’s on the horizon, good or bad, that you should be mindful of when moving forward? How can you start proactively planning with these things in mind?

5. Who deserves a shout-out?

It’s been a long sprint, and it’s important to recognize the team and individual wins—big or small. Shoutouts shouldn’t only come from the manager, they should come from everyone on the team. Encourage recognition for behaviors your team values. For example:

  • Did someone go above and beyond to help a team member?
  • Did someone share something helpful in your Slack channel?
  • Did someone produce exceptionally high-quality work?

This is more than just a feel-good item. Recognition is an important part of employee engagement and motivation.

Wrapping up

Running a sprint retrospective every single sprint may seem like overkill in your busy schedule. But, hopefully, after reading this article you understand why they’re such an essential part of running an agile team. Don’t dwell on the past, rather use these recurring meetings to get a pulse check on what was accomplished, what’s working, and what can be improved for the next sprint.

Taking an hour once a sprint to run a retro with your team will ultimately save you a lot of time and inefficiencies in the future.

By: Graham McCarthy

Graham McCarthy (1)

Graham is the CTO & Co-Founder of Hypercontext , a suite of tools to help leaders and their teams streamline objectives, meetings, and morale into one workflow. He’s an experienced technical leader with a demonstrated history of working in the computer software industry, specifically in SaaS startups.

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