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Brainstorming Doesn't Have to Suck - Here's How To Make it Work

Brainstorming Doesn't Have to Suck - Here's How To Make it Work

“Move fast and break things” mantra is written across whiteboards of startup offices everywhere. Startup teams are repeatedly told to execute more ideas quickly, yet the lack of knowledge of how to generate compelling ideas in the first place causes bottlenecks in shipping new product features, or worse crappy ideas that will certainly fail quickly.

Generating useful ideas requires preparing for the meeting by understanding the problem being solved for the people using the product.

Preparation: The people using your product 

In preparation for the meeting, talk to the people who use your product to understand who they are and why they use your product. Slack chats and emails will tempt you, but spending time digging into your product data and customers will pay larger dividends.

Split your time analyzing qualitative data (think Net Promoter Score survey, customer support emails, calling a frustrated customer) and quantitative data (funnel drop-off rates, conversion rates, average order value) and build a comprehensive view of your customer. 

The quantitative data tells you what is happening and the qualitative data tells you why it’s happening.

If your data is lacking, gather a group of five people and observe how they use your product to understand their lows and highs with the product. In the meeting with your team, reinforce how the customer thinks of your product by using the colloquial language your customers use when describing the product.

At RetailMeNot, we called this page “Your Profile” until we repeatedly heard customers call it “My Wallet” because it’s where their rewards are stored. By listening to the words they used and updating the label, we saw higher visits to the page. 

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Preparation: The people you work with 

It’s not skills or experience that creates the most successful teams, it’s psychological safety which is the ability to generate ideas without fear embarrassment or retribution from team members, according to a study by Google. It’s critical to build trust with your team before brainstorming because it will lead to higher contribution in the meeting. Employees are routinely asked to do tasks at work that they will be surprised when someone genuinely asks how they are doing. An effective team member forms strong alliances with the other people on their team. Before the meeting, grab coffee and have 1x1’s with your team leads. Like understanding the behaviors of your customers, it’s valuable to do the same with your team members. Ask about what’s challenging them on the project and how you can help. Listen intently without offering advice. Ask about their weekend plans, and then follow up on Monday asking specifically how those plans were. Learn when they like to have meetings and schedule them during these times.

Meeting Day: The Problem  

Arrive to the meeting early, before anyone else has arrived, and write out the key problem the product is solving and the goal of solving this problem on the whiteboard. Adjacent to the product and goal, add two customer quotes and details about these customers using personas.

Since we are wired to think from our perspective, building personas for your customers helps team members think about ideas that work for the personas, not for themselves. A persona includes things like name, location, relationship, children, job, hobbies, behaviors, desires, and needs. Add supplemental quantitative data, like graphs or stats you discovered in preparation for the meeting. Visuals reinforce the problem and the person and serve as fuel to kick off creative thinking. Start the meeting by reciting the information on the whiteboard to engage visual and verbal learners.

Once the room is familiar with the context of the meeting, begin the brainstorming process. 

The first half of the meeting is devoted to divergent thinking - as many ideas as quickly as possible, bold and crazy, without elaborate detail. Like improv comedy, encourage people to respond with yes and build on ideas, no matter how crazy, instead of restricting ideas during this half. Encourage 10,000 foot view thinking with broad, open-ended questions like:

  • “How might we make it easier for Susan to buy from us?” instead of boxing in with solution-oriented questions like “can we fix the checkout screen?”

  • “How might we..”

  • “Couldn’t we just..”

  • “What does the world look like if we…”

  • “What would make this easy?”

Time-box the team to generate as many ideas on the whiteboard as possible. After the first phase of idea generation is over, set a timer for three minutes of silent time to avoid groupthink for each member of the group to review the ideas.

Give each person three sticky dots and one minute of silent voting to stick dots on their favorite idea, the one that best solves the problem for the person with the problem. It’s not about the coolest idea (save it for a hackathon), and it’s not the time to rank ideas based on business goals (which comes later). 

The second half of the meeting is devoted to convergent thinking which means narrowing down and refining the ideas. As the moderator, read out loud the ideas with the most votes. Save all the ideas for later with a picture, and erase the “losers”.

As a group, identify the remaining ideas' themes and differences the remaining ideas have with each other to narrow down further. Ask questions like:

  • “How are these ideas similar?”

  • “How do these ideas differ?”

  • “What connects these two very different solutions”

Next, add details to the ideas.

  • “How would this work”

  • “How does our customer find this? How do they use this?”

  • “If this worked, what went right?”

  • “If this didn’t work, what went wrong?”

  • “What has to happen for this to work well?”

  • “What known unknowns do we need to figure out?”

  • “Are there known unknowns we can’t resolve until testing and launch?”

Add a handful of details to each idea. After adding detail to the solutions, distribute more sticky dots and conduct a final round of quiet voting to identify the top winner(s). Recap the winners back to the group before ending the meeting. 

Post-Meeting

Document the list of stack ranked ideas in an easily accessible place for the team. Distribute this document within 24 hours of the meeting ending while the meeting is fresh on people’s mind. Celebrate the ideas generated by the team. 


Now you have ideas, and you’re ready to move fast and break things.

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