The first, most integral part of pursuing your business’s Second Act is a really excellent brainstorming sesh. You know the feeling: Whiteboards! Coffee! The term “blue sky” being thrown around like Bushwackers on Broadway! Once you decide you’re open to (or maybe desperately need) a major change, a session like this is typically the next step.
Here’s the problem: brainstorming sessions are usually the worst. The absolute worst. For one, generating ideas for a major pivot is a lot of pressure, which is not conducive to creative thinking. For another, just gathering the team in a room on a whim and saying “seriously y’all, think blue sky! Give me some ideas!” isn’t enough to inspire truly creative, boundary-testing thinking from your team.
When I set out to write this piece, I thought it was going to be a simple advice roundup. I’d just consult the trusty Internet, pick the tips I liked best, and consolidate them for you all here.
Instead, I got to the end of Google and realized: I still have no idea how the hell to run a brainstorm that doesn’t suck.
Almost immediately after that, I found myself in precisely the position I just described—having to lead a brainstorming session around a core business problem with the whole team. And I still didn’t know where to start.
Teaming is a fellow Nashville startup that gives leaders the tools they need to grow healthy teams. The platform helps teams align on direction and values, make decisions and commitments to reach shared goals, and strengthen team relationships. I might be biased, but it’s pretty rad.
When I asked Kate for her thoughts on mistakes I should avoid while leading this session, she said, “The biggest mistake I've seen leaders make when leading a brainstorm is going in thinking they can run a perfect one. These sessions are hard and messy. They are also a learned skill by everyone who participates in them, so they take practice.”
So, practice I did. And happily accepted a lot more advice from Kate. What resulted is the following advice on leading brainstorms that don’t suck, tried and tested by the Gun.io team with Kate’s expert guidance.
Let’s talk raw numbers. The pizza rule isn’t new to anyone, but it’s worth repeating here: if you have more people than you could feed with a pizza in the meeting—particularly if you plan to generate ideas live—it’ll be tough to make real progress. Break into smaller groups if necessary.
Then, organize your brainstorm groups to optimize for creativity. If you’ll need to divide folks into multiple sessions, try cross-teaming—create brainstorm groups with a member or two from each team, rather than putting the product team together, the marketing team together, and so on. Different combinations of minds will get folks out of their usual roles and thought patterns.
If cross-teaming doesn't work, try putting all of the usual leaders in one group, and everyone who’s typically a bit more reserved in another. Switching up the team dynamics can solicit totally different outcomes.
As for timing, Kate suggests choosing a time that will allow your team to compartmentalize everything else they have on their minds that day so they can focus on the creative task at hand. Here are some of her best tips to do this:
When I asked our newsletter readers for their best advice for leading a brainstorm, the most common response (in classic developer fashion) was: don’t.
“They only favour quick thinkers, which is not the whole population,” one reader wrote, recommending instead that the facilitator send out the question a week in advance to give folks time to generate ideas. Another added that anonymity is key: sharing anonymous ideas means “nobody is afraid of being shamed for proposing a ‘bad’ idea,” and ensures that the usual suspects won’t steamroll the conversation.
Whether we realize it or not, we all put our ideas through a subconscious “how will this make me look?” test before we share them. The thoughts we share with others are just as much about how we want to be perceived by the group as they are about the value of the idea itself.
Recently, our team at Gun.io was trying to crack a pretty tough growth question. Knowing that self-consciousness kills creativity, we asked for anonymous idea submissions in a simple Google survey. Then, a few days before the meeting, we categorized and shared out the full, unedited idea list in another Google survey, asking folks to upvote and leave comments on ideas they wanted to discuss further in the brainstorming session to come.
Keeping the submissions blind not only helped us hear from everyone, but also prevented unconscious bias from informing which ideas, at face value, we thought were most exciting. It took the pressure off being perceived as the most innovative person at the brainstorm, and instead facilitated more meaningful conversation.
I know it can feel very High School English Class-y, but as a former teacher, I promise you: we use prompts because they work. Sometimes you have to get a bit silly to generate the best ideas. Here are some of our favorites:
While it might seem counterintuitive to blue sky thinking, if you don’t identify the real constraints you’re working with upfront, they’ll creep into your teams’ subconscious, unchecked. Kate shares that at Teaming, this is the most important part of their brainstorming process:
We need to leave our constraints at the door—our own personal constraints, and our perceived team and company constraints. This is the hardest because it requires a lot of awareness of each constraint. There are constraints we're aware of like money or time, but there are a lot of constraints that we're unaware of, too. Tips for helping team members do this are:
A team that doesn’t feel safe or appreciated in the course of a normal workday won’t miraculously feel comfortable sharing ideas in a brainstorm, just because you meticulously planned an awesome session.
Show your team that you genuinely want their input by removing yourself (the manager) from the decision-making process. I had an old boss who was notorious for gathering everyone in a brainstorm, asking for hours of our time, when he actually already had the solution in mind. After we all shared ideas, which were met with disinterest at best, the sessions inevitably devolved into a means to generate buy-in for his idea.
To avoid this, Kate recommends placing the power of the final call in your teams’ hands, not yours:
As managers, we're responsible for the team's performance, but the team is responsible for the work, and therefore they should decide how to do it. I recommend that the manager set a goal or target and let the team go off and decide how to achieve it together. The team will be more bought-in and more accountable for achieving what they set out to do than if you were involved in the decision-making process to begin with.
The most important thing when removing yourself from the decision-making process is to be sure that every person on the team feels comfortable coming to you if they get stuck. Also, when the team walks you through their decisions, try to ask open-ended questions rather than directed ones. For instance, 'can you tell me the considerations you made for this decision?' is a lot more powerful than 'have you considered X?'
Kate’s most important ingredient in the formula for an amazing, creative team is psychological safety. Teams that are afraid of failing or disagreeing with each other tend to generate (and act on) small, “safe” ideas. If what you’re looking for is bigger than that, you’ll need a team that feels psychologically safe.
Psychological safety on a team means that it's members aren't afraid to fail, they are comfortable engaging in conflict with each other, they take risks, they share ideas before they're fully formed, and they know how to share feedback with each other.
Creating psychological safety is hard. It requires daily attention to interactions between team members and being a self-aware manager. Here's a few general tips for creating psychological safety:
Creating the right conditions for creative thinking is the most important job of a leader. Don’t be afraid to experiment with the strategies laid out here—even (and especially) if this is completely new for your team. Let us know what you try, or if you have ideas we didn’t include; we’d love to learn from you!
Posted by Faith BensonLinkedIn Twitter Website