The path to innovation is rarely straightforward. Divergent thinking is a mindset that encourages us to consider multiple solutions and break free from conventional approaches when they aren’t serving our needs.

Divergent thinking doesn’t tend to be part of our day-to-day conversations, perhaps because it requires us to challenge ingrained habits and beliefs, pushing us outside of our comfort zones. We’re much more comfortable with incremental improvements. They’re easier to propose, measure, implement, and are implicitly less risky. While these step-by-step changes can bring about progress, they usually keep us operating within our existing frameworks.

Engaging in divergent thinking by asking “what if?” to theoretically eliminate what’s perceived as a hard constraint can lead to meaningful and transformative changes, pushing your team toward greater productivity and effectiveness.

How to spark divergent thinking

A good prompt can help spark divergent thinking. My favorite prompts focus on two concepts:

1. Securing a better future
2. Improving the unspoken tradeoffs of today

Both types of prompts encourage us to interrogate why we are doing certain things and not doing others. It’s okay, and even encouraged, if the prompts seem fantastical or absurd. Extreme thinking is the whole point.

The payoff can be considerable. Here are two examples of how divergent thinking led to a large impact on organizations I’ve worked with in the past:

• How similar do development and production need to be? In this instance, we reconsidered the constraints we assumed around the local development version of the front-end build and ultimately agreed that we didn’t actually need to use the same tech in development vs. production. The resulting actions reduced front-end build times from minutes to seconds without sacrificing production quality.
• How could we achieve this without a pull request? Here, country managers wanting to run simple experiments were bottlenecked by engineering resources. In response, we built a tool that allowed country managers to test certain changes without relying on engineers, unlocking a flood of valuable experiments.

How prompts can solve problems 

Let’s delve into a few provocative prompts designed to kickstart divergent thinking in your teams.

“What would it take to not have to do X anymore?”

This question encourages us to look ahead and imagine a world free from our current pain points. Envisioning this alternate reality is easier said than done, especially given the pressing demands of software engineering work. The team might be so entrenched in daily firefighting that it overlooks the issues that, if solved, could significantly improve their workflow.

For example, consider a recurring problem like flaky tests. While teams may tolerate them as an unavoidable nuisance, asking this question can lead to an in-depth analysis of the root causes and potentially to a more reliable testing suite.

“If only X, Y would be so easy — why haven’t we done X yet?”

This question might be uncomfortable because it challenges the status quo and implicitly criticizes past or current decisions. But it also has immense potential to unlock new efficiencies. For instance, if manual code reviews are a bottleneck, why hasn’t automation been introduced into the process?

While the initial thought might be resource constraints or lack of expertise, further exploration might reveal that the real obstacle is an unwritten rule or an unfounded fear that automated checks could never match human scrutiny. This realization could lead to a trial phase for automated code review tools, changing the dynamics and speeding up the deployment pipeline.

“What would happen if we stopped doing X?”

This question is particularly powerful but also intimidating, as it challenges some activities and roles within the team. An example may be opting to abolish certain types of meetings. Things to consider, in turn, would be how the team’s coordination and product quality is impacted.

The answer may reveal that some meetings are more ritualistic than functional, leading to reevaluating their necessity. This exercise can help focus team efforts on activities that genuinely add value, which is a step change in becoming more effective.

“We often say no to requests for X – what would make it easier for us to say yes?”

This question directly confronts the limitations and boundaries of engineering teams. For example, if a team regularly says no to incorporating new technologies due to the necessary learning and implementation time, what could change this?

This question may lead to discoveries about resource allocation, workflow inefficiencies, or even larger organizational bottlenecks. Implementing a solution could involve better project scoping, upskilling the team, or perhaps rethinking the entire product development process.

“X is a valuable thing we could do more of, if only Y”

This prompt focuses on valuable activities that could be even more so. Teams often zero in on problem areas, overlooking opportunities to amplify what works well. This question nudges the team to think about barriers that might be holding back optimization and expansion, and it serves as an invitation to envision a future where those barriers are removed.

Rather than identifying what's broken, this question asks what’s stopping a team from elevating areas of strength that can drive meaningful change. Discussing these “if only” scenarios helps the team understand what could improve an already productive system.

The right time and place

When should you be asking these questions? Not in your daily stand-up, that’s for sure. These sorts of conversations require space and time. Consider integrating them into quarterly planning sessions or dedicated brainstorming meetings.

If you find one-off sessions productive, you might also consider setting time aside on a regular cadence for a divergent thinking exercise. Before the meeting, solicit topics from the team that would benefit from some fresh perspectives. Come up with a shortlist that everyone on the team can contribute to beforehand, and get input from the team’s stakeholders too.

On the day of the session, start with a quick reminder of why divergent thinking is useful and that the goal isn’t to leave the meeting with concrete plans, but to explore as many different angles as possible. You could introduce provocative questions for each shortlisted topic during the discourse to encourage divergent thinking. Brainstorm and discuss to identify ideas that seem most promising and worth exploring further.

After the meeting, summarize the ideas that came up and what the next steps are. The next time you hold one of these sessions, you can also review any progress that’s been made on the ideas since the last meeting.

Empathy and reflection

Asking questions that inspire divergent thinking can stir up strong feelings. When scrutinizing past decisions, be empathetic to those who made them. This may be you, your team members, or people who came before you. Assume that they were the best possible choices given the information, resources, and constraints at the time. If the aim is to foster a culture where people feel empowered to suggest innovative ideas without fear of criticism, then a compassionate, understanding approach is essential.

These aren’t quick conversations. Make sure there’s time for in-depth discussion, and set ground rules like “no bad ideas” to ensure everyone feels secure enough to speak their minds. Exploring these topics will go best if you take into account:

• Psychological safety: The team needs to feel secure in expressing thoughts that may counter existing norms or practices.
• Time for reflection: Plan to set aside focused time for these questions. Their value doesn’t lie in quick answers, but in the thoughtful dialogues they initiate.
• Actionability: The aim is not just to question but to change. Gather action items and owners, and plan to schedule at least one piece of the resulting work in your next planning cycle. 

Be divergent

When you weave these questions into your team’s discussions, you cultivate a pattern of thought that aims for transformation, not just incremental change. It’s a vital step in the journey toward greater engineering effectiveness.

By making these questions part of your team’s DNA, you’re committing to doing better work and rethinking how that work gets done. And in the world of software engineering, that can make all the difference.