Three Questions for Transformation

Transformation doesn't have to come from outside your company. Picture this: a simple framework that not only acts as a catalyst for profound change but also enhances your leadership prowess. Intrigued? Let's explore the transformative realm of retrospective meetings and unveil the secret to continuous improvement.

Retrospective meetings exist in many forms including “lessons learned” meetings, agile retrospectives, project post-mortems, after-action reviews, debriefs, and pre-mortems. You may also be familiar with its cousin, “shame and dishonor,” where people shift blame and assign disgrace; that meeting is far less helpful, but widely practiced sadly. 

As much as retrospectives can be painful, I have a confession: I love them. You should, too. Here’s why:

Transformation is a powerful act for any business. Whether the transformation is digital, business, operational, or process, it marks a powerful opportunity to drive meaningful improvement. A retrospective offers a team and a company a chance to do that without bringing in a team of expensive consultants. It brings together fresh observations from the people who know the business as well as anyone. Think of a retrospective as a chance to do a “mini” transformation.

Retrospectives are fueled by data (when they are actually done – and they often are skipped in my experience). Beyond project data, the most common tool I’ve seen for input is a survey. Post-project surveys serve as invaluable tools for gathering qualitative feedback, insights, and lessons learned. Leaders often try to make this data quantitative by assigning scales such as A - F, 0 - 10, 1 - 5, Strongly Disagree to Strongly Agree. Surveys have practical outcomes including accountability, transparency, communication, opportunities for improvement, and more. 

Also, surveys are typically terrible.

It’s not your fault! Crafting an effective survey is exceptionally challenging. It’s difficult to select a scale that works. Normalizing responses is a pain. Writing questions that avoid bias in wording is an art form. People design surveys for a living, and there’s a good reason why. It’s hard.

In my experience, simplicity is key to a good survey. To drive periodic and meaningful transformation through the retrospective, you need a streamlined approach. Here is one example I have successfully used, focusing on just three questions that yield profound insights and foster meaningful improvements. Each question is tied directly to an outcome.

Here’s what I focus on:

1. Improve Your Team

We want a survey that will have an immediate impact on the current team (or individual contributors who will join new teams). Gathering feedback to improve current processes, address challenges, and celebrate successes directly contributes to the team's growth, collaboration, and efficiency. Your job is to be responsive to members' experiences and adapt quickly to optimize performance.

Here’s the question I use: 

"What specific challenges and/or successes most stood out to you on this project, and how can we leverage your insight for future projects?"

Here’s why I like it:

• Open-Ended: Allow respondents to express their thoughts freely without being constrained by predefined options. There are no leading statements or predetermined options that might influence their responses. Encourage them to share their unique perspective without the constraint of your available options or as a throw-in “anything else” question at the end.

• Specific: By asking about “specific challenges and/or successes”, the question prompts respondents to pinpoint exact situations or aspects of the project. Context helps. By encouraging respondents to consider their insights in the context of future projects, the question promotes a collaborative mindset.

• Solutions-focused: The question goes beyond identifying problems; it also asks respondents to suggest how their insights can be utilized for future projects. This forward-looking approach fosters a sense of collaboration and encourages respondents to think constructively about solutions.

2. Help Future Teams Doing Similar Work:

We want a question that provides insight for future teams. Think of this as a message in a bottle. I’ve often belonged to teams where people recall that “person X did something like this 3 years ago” or “team Y worked with that vendor last year”. Your success in future efforts should not be predicated on detective work. Be the person X and team Y you wish you had. It promotes knowledge sharing, prevents the repetition of mistakes, and accelerates the learning curve for subsequent teams. It also recognizes the interconnectedness of projects and teams over time.

Here’s the question I use: 

"Reflecting on our experience, what advice would you give to future teams working on similar projects, and what do you wish you had known?"

Why it Works: 

• Perspective-Based: The question encourages respondents to reflect on their own experience. By focusing on advice derived from personal experiences, the question elicits practical, positive, real-world insights. Respondents are likely to share advice grounded in the challenges they faced and the strategies that proved effective, offering tangible recommendations for future teams. The question implicitly encourages a mentorship mindset.

• Identifies Gaps: The question's second part, asking about what respondents wish they had known, targets knowledge gaps or areas where previous teams might have struggled. This insight is invaluable for anticipating challenges and proactively addressing them in future projects. It’s also not limited to specific experiences because it asks what they wish they had known.

• Avoids Hindsight Bias: While the question asks about what respondents wish they had known, it does not impose a hindsight bias. Instead, it invites respondents to consider their potential advice within the context of the project timeline, allowing for a balanced perspective on challenges and opportunities. This question seeks advice that is practical, relevant, and actionable for future teams. 

3. Provide Insight to the Larger Org or Company:

Insights gained from individual projects can inform strategic decisions, influence company-wide practices, and contribute to a more informed, agile, and adaptive organization. Retrospectives are among the most powerful opportunities to influence transformation for a company. The insights gained are curated and equitable insights from teams for continuous improvement.

Here’s the question I use: 

"What impact do you believe this project had on our stakeholders and clients, and what insights should we share for future initiatives?"

Why it’s a great question:

• Stakeholder-Centric Focus: By directly asking about the project's impact on stakeholders and clients, the question emphasizes the importance of considering external perspectives. Respondents are prompted to assess the project's outcomes empathetically from the stakeholders' point of view, ensuring a client-centric evaluation.

• Forward-Thinking: The question focuses on the long-term implications of the project and its potential impact. Focusing on future initiatives, encourages forward-thinking and strategic planning, ensuring that the organization learns from the current project to drive future success. By asking for insights to share for future initiatives, the question taps into respondents' analytical skills. Respondents are prompted to distill overarching themes or patterns from the project's impact, offering actionable insights for shaping future strategies and initiatives.

• High Level: I said three questions, so this is cheating a little, but you can ask this same question before the retrospective meeting to get insight AND after to distill thoughts further after minds meet. Because it has a client-centric focus and forward-thinking approach, it can be helpful to revisit after a retrospective workshop to further document project outcomes and inform strategy.

Conclusion 

A retrospective is a powerful moment for intentional reflection and presents an opportunity for improvement of team performance, to reduce risk for future project teams, and to drive transformation for the organization.

The three fundamental questions presented here provide an architectural framework for fostering transformation. Simplicity, often overlooked in the complexity of survey design, becomes the cornerstone for meaningful leadership insights. The journey toward improvement may not be glamorous, but it is undeniably necessary! 

Embrace the power of collective intelligence and ask these three questions before your next retrospective. Use the insights gained to find common themes, outliers, and diverse voices in your organization. Embrace the mini transformation! 

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