Retrospective 101: Maximizing Lessons from Past Projects

One silver lining for every project is the wisdom you receive from it—whether it’s a total success or an abject misstep. This is true of all the small moments within the project, along with those nuanced interactions with your clients. There is always a lesson.

The question is, however, is your company or agency extracting the most knowledge and insight possible from its experiences? Unfortunately, the answer is likely no. In the business world, there is often a rush to move on to the next project without giving a team a chance to pause and reflect on their recent experience.

This is why project retrospectives are essential—they provide a flexible yet structured way of reviewing and refining your project process, and this article will tackle precisely how you can accomplish this.

What is a Project Retrospective?

A project retrospective is a holistic review of a completed project. It’s dedicated time for reflecting on what went well and what could have been done differently. It’s also a time to consider what can be improved upon.

Historically, project retrospectives have been mainly used in the IT sector. Now, however, the practice is finding utility across many different sectors, especially for small businesses and creative agencies where nimbleness and adaptability are non-negotiable, and every project’s outcome can have a massive impact on reputation and client trust.

Leveraging Data and Tools for Effective Retrospection

Since, nowadays, pretty much all sectors work with copious amounts of data, it’s no wonder project retrospectives have become indispensable. If a retrospective fails, it can very often be blamed on the lack of concrete data or even the lack of ability to grasp and process that data properly.

Before you dive into the numbers, it’s imperative that you begin with understanding which key performance indicators (KPIs) influenced your project’s outcomes. Some metrics like customer satisfaction (CSAT), time-to-market (TTM), and even backlink analysis results can tell you how well your project team performed.

Observing click-through rates or referral traffic from your link-building campaign, for example, can show you how well it’s performing and contributing to your project’s marketing goals. You can then use this information to adjust your marketing plan accordingly.

In addition to traditional campaign or sales-related metrics, a project retrospective should also involve input on:

• Time tracking: Businesses can determine areas that are being used efficiently or inefficiently by analyzing how the time was spent across specific parts of the project.
• Task management: Looking into task completions and delays can provide insights into bottlenecks and potential areas for training.
• Milestone reviews: Were all milestones achieved on time? If not, what were the common challenges faced? Milestone reviews can lay bare strategic issues faced during the project.

Traversing Tech: Project Retrospectives Beyond IT

As we mentioned before, retrospectives have their roots in the IT sector. That said, nowadays, their utility spans far beyond the tech world. Various industries, from healthcare to construction, have adapted this practice to glean insights from their own unique workflows.

Even in fields like medicine, teams are finding value in conducting retrospectives to understand the effectiveness of their campaigns, optimize patient engagement, and fine-tune their B2B marketing strategies with the power of LinkedIn analytics and other data.

You’ll notice that the more niche a project is, the more important a retrospective is. But no matter the field, niche topics always require more precise data, making leveraging all possible channels a top priority.

Then again, even big names are taking advantage of retrospection tools. For instance, Paymo’s time-tracking software and other project management solutions are used by Adidas, NYU, and Accor Live Limitless — far from tech-only organizations and also far from niche brands.

Regardless of the sector, the goal is the same – continuous improvement. It’s about recognizing that no matter how successful a project seems on the surface, there’s always something to innovate on.

Business Culture: Building a Retrospective Mindset

If retrospectives aren’t ingrained into your organization’s culture, you can’t truly count on them being very effective. It isn’t enough to just schedule a meeting after the project so it can be another checkbox ticked. Your company (or at least your project team) must have a mindset of constant learning and improving.

1. Fostering Open Communication

Sometimes, in smaller companies or agencies, there is a hesitancy to speak up, especially if the feedback could be viewed as negative or critical. Given the choice, most people choose non-confrontational measures. But this can spell failure for a retrospective. Every team member must feel empowered to share their views, regardless of how unpopular they may be, and they can do so with:

1. Safe spaces: You need an environment where team members know they won’t face adverse consequences just for expressing their views. This goes double for new team members who will be less confident about dissenting from their coworkers.
2. Facilitated discussions: If there is a facilitator in your organization, they must be impartial at all times. Their role is simply to ensure everyone has a chance to speak and that the conversation remains constructive and helpful.
3. Usable feedback: As a corollary to the previous point, encourage your staff to give their feedback as constructively as possible. Try to get them to focus on what can be done to improve, not just on what failed (“it’s bad” vs. “I believe we can do x,y,z”).

2. Embrace the Failures

No company has a 100% success rate for projects. Some will fail. What matters is how you respond. Failures must be embraced as learning opportunities, usually more so than successes. Foster this by:

• Celebrating the lessons: Instead of lamenting bad results, get your team to learn how to celebrate the lessons learned. It’s a great way to destigmatize the idea of failure and help your team focus on what can be used to benefit your projects going forward.
• Documenting everything: Keep detailed records of both successes and failures. A repository of past projects, especially failed ones, is invaluable for future attempts. These can be particularly handy for small business owners who may not have the luxury of repeating mistakes because of limited resources.

3. Bridge the Knowledge Gap

Retrospectives are great at showing the existing gaps in the team’s knowledge or skill sets. This is not a negative. It provides a fantastic roadmap for training them:

• Regular training: Upskill sessions should be done regularly. This could be anything from training on the new software tool to learning about project management best practices for project managers. Constant learning is how you help immunize your team against the spread of future project failures.
• External insights: Sometimes, you need an outsider’s perspective. Don’t think twice about inviting a client or industry expert to share their insights during your retrospective. Teams often have the issue of being unable to think outside the box due to the time spent in it, and sometimes, a fresh face is all you’ll need to set things straight.

4. Keep the Momentum: Continuous Improvement Cycle

A single retrospective is just a drop in the ocean. Making it a consistent practice—a holy discipline—is how you continuously improve, especially if you implement:

1. Regular scheduling: Don’t wait until the end of the project to schedule the retrospective. Hold mini retrospectives at certain milestones. This allows for rapid course correction and fewer errors overall.
2. Action items: Every retrospective ends with precise and usable goals. Give them deadlines. Give those deadlines consequences. This way, the retrospective doesn’t just remain on paper.
3. Reviews and refinements: The retrospective itself should be open to review and refinement. Ask for feedback on the process itself, including tools used and format. The process itself must evolve along with your team.

Financial Reckoning: Evaluating Cost and ROI

Financial considerations cannot be avoided when assessing project profitability and performance. This means poring over budgets, costs, revenues, and the return on investment (ROI). Cash flow management is one often overlooked but highly impactful aspect. It can make or break your project, and if it’s threatening to break it, you must think of quick solutions.

For instance, if the project faced liquidity issues, techniques such as invoice factoring could help maintain a steady cash influx so that all tasks continue without a financial hitch. Or you could organize business expenses into tax-friendly categories so you understand your spending habits and can reduce your total tax bill.

Despite all the creative workarounds and strategies, nothing beats having a thorough financial review. For small businesses and agencies where budgets are tight and every penny counts, every project’s financial implications become important, which is why you must focus on the following:

• Budget analysis: Did the project stay within the budget? If not, what caused the excessive expenditures? Were they justifiable in the context of client demands? Or was there a problem with estimation or managing resources?
• Return on Investment (ROI): The immediate financials may be fine, but what added value did the project provide? Did it open doors to new market segments or strengthen the brand?
• Opportunity costs: What other projects or opportunities were passed over for this one? In retrospect, was this the right decision?

Practical Application: Making Retrospectives Work for You

Understanding retrospectives is one thing; effectively implementing them is another. Here’s a quick guide to help you get the most out of them.

1. Start with Clear Objectives

You must know what it is you want to achieve. Are you looking for process inefficiencies? Or to understand the team’s morale throughout the project? You need clear objectives to have focused discussions and move forward.

Let’s say that your team’s goal was to increase the conversion rate of the company’s landing page by 20% within the next quarter.

This goal is specific, measurable, achievable, relevant, and time-bound (SMART).

During the retrospective, the team can analyze the marketing processes that led to the current conversion rate and identify areas for improvement.

The team will go through the following checklist of marketing processes that lead to better conversion rates:

• Create dedicated landing pages for your paid advertising campaigns
• Shorten your forms
• Include social proof
• Track how people interact with your site
• Add live chat
• Use a CRO planner
• Optimize each location where conversions can happen
• Use text-based CTAs within blog posts
• Increase trust and remove friction
• Be creative with your mobile marketing
• To understand user behavior, use website surveys, heatmaps, customer calls, customer support tickets, and session recordings.
• Focus on designing killer calls to action (CTAs)
• Incorporate social proof, clear CTAs, mobile-first design, and prioritize user experience

Now, the team can discuss what worked well in the previous quarter and how to replicate those successes in future campaigns.

They can also discuss aligning their goals and strategies with the company’s vision and mission.

2. Embrace Diverse Tools

There is a whole world of useful software solutions out there. You could use a mood board for the design team or a financial dashboard for budget insights. The point is to have all usable data accessible and understandable. Ideally, you should look for something that lets you manage multiple projects, ensure time efficiency, and track payments all on one platform, such as Paymo.

Dashboards can be little delighters when they help you zone in on your work for the day:

Paymo’s “My Day” takes a look at your daily tasks to help you focus

3. Involve Everyone

A retrospective isn’t just for the project manager. I’ve already discussed why bringing perspectives from outside the company is a good idea, but don’t be afraid to include employees from other departments. You can better understand the project when you have a diverse range of voices.

Here are some concrete examples of how to involve everyone in a retrospective:

• Start Stop Continue Retrospective: This retrospective style generates an immediate list of practical ideas for continuous improvement. Using a timer, you can timebox discussions to keep the conversation on track and the retrospective on course. Make the most of your presentation mode and drill down into ideas at the brainstorming, grouping, as well as discussion stages of your retrospective. Keep your team agreements in view during your retrospective and give people “silent time” to write, read, and respond to what is being presented.
• KALM Retrospective: This interactive sprint retrospective idea allows team members to share their perceived value of the various aspects of the sprint. Suggested icebreaker questions for KALM retrospectives include “When have you kept calm and carried on?” and “What would be beneficial if you had less of it in your life?”. Need to turn one of the ideas into an action item or team agreement? You can do it directly in TeamRetro and turn a comment into a proposed action or team agreement.
• Sprint Retrospective: This retrospective is a golden opportunity for your team to express themselves. It’s imperative that we learn how to listen to them. Sometimes teams get bored when they don’t see changes or actions based on past retrospectives. Other times, the team lacks the motivation to fully express how they truly feel about how the project is progressing. At the end of a retrospective, everyone involved should decide on the action items that should be taken to improve future sprints.

To involve everyone in a retrospective, creating a safe and inclusive environment where everyone feels comfortable sharing their thoughts and ideas is vital. Encouraging everyone to participate should be the primary objective.

Documenting their input should also be a top priority, as you will want to act upon suggestions. Using facilitation techniques that create rules about what you can do at certain times can also help to create structure around the conversation.

4. Stay Time-Bound

Retrospectives can drag on longer than they should—it’s one of their pitfalls. It’s best to stick to a time frame to mitigate this delay. Usually, 60-90 minutes is more than enough to address concerns. Follow-up sessions can always be scheduled afterward for special issues.

Here are some tips on how to stay on time or keep a retrospective under 2 hours:

• Timebox your meeting. Set a specific time limit for each retrospective phase and use a timer to keep track of the time. This will help to ensure that the meeting stays on schedule and that each topic is given the appropriate amount of time.
• Collect feedback in advance. Ask everyone to submit their thoughts asynchronously before the retrospective begins. This will save time during the meeting and allow the team to focus on discussing the most important topics.
• Stick to the agenda. Follow the agenda set before the meeting and avoid getting sidetracked by unrelated topics. If new topics arise, write them down and address them in a future meeting.
• Assign a facilitator. Appoint someone to facilitate the meeting and keep the discussion on track. The facilitator can also ensure that everyone has a chance to speak and that the meeting stays within the allotted time.
• Prioritize action items. At the end of the retrospective, prioritize the identified action items and assign them to team members. Ensure the action items are specific, measurable, achievable, relevant, and time-bound (SMART).

By following these tips, teams can stay on time and keep a retrospective under 2 hours. It is important to remember that retrospectives should be productive, practical, enjoyable, and engaging for everyone involved.

5. Act on the Insights

A retrospective without action is a waste of time. Assign a team member(s) responsibility for every insight or action item. Use tools to track the tasks to ensure they are acted upon. This is how you ensure the retrospective isn’t just completed on paper.

Let’s say the team failed to increase the conversion rate of the company’s landing page by 20% due to lack of trust and increased friction. The team identified four action items to be done in this respect and assigned owners for these tasks to be done:

1. Simplify the landing page design to make it more user-friendly and easy to navigate. Remove any unnecessary elements that may cause confusion or distract the user from the main call-to-action (CTA).
2. Optimize the page load speed: Improve the page load speed to reduce the bounce rate and increase the time spent on the page. Compress images, reduce the number of HTTP requests, and minimize the use of plugins and scripts.
3. Test different CTAs: Test different CTAs to determine which resonates best with the target audience. Use clear and concise language that communicates the value proposition of the product or service.
4. Use social proof: Use social proof to build trust and credibility with the target audience. Include customer testimonials, reviews, and ratings on the landing page.

Using a task management tool of your choice, you would then transfer what was jotted down during the retrospective into an actionable task list with due dates, priority, and assignees:

In Paymo, tasks can be grouped by task lists, due dates, or priority

6. Revisit Past Retrospectives

It’s valuable to look back on past retrospectives every few months—it’s the reason you’re recording them, after all. So ask yourself: Have the identified challenges been addressed? Have the solutions worked? If not, it’s time to try another line of attack.

7. Stay Flexible

Structure is important, but each project is unique. What works for one retrospective may not work as well for another. Therefore, it makes sense to be adaptable and willing to change the approach based on your team’s current parameters and feedback.

Conclusion

Retrospectives offer companies and agencies an anchor of reflection. They do this best when companies can find and use the right tools while fostering good communication and sticking to a set schedule.

Past retrospectives serve as a snapshot of what worked and what didn’t and provide companies with a ton of data they can use to sharpen their project process and constantly improve their projects and their training resources.

By consistently looking back, teams ensure they’re always moving forward in the right direction, learning from the past, and building a brighter, more efficient future.

First published on October 23, 2023.