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March 31, 2021 · 10 min read

5 tips for brainstorming sessions that don’t suck

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 brainstorming sessions that don’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.

So, I reached out to my personal board: our weekly newsletter readers, who always have good advice up their sleeves, and my friend Kate, co-founder of Teaming.

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 team with Kate’s expert guidance.

First, think critically about the invitation: who’s on it, and when?

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:

  • Plan the sessions on an average day—a day that’s not the busiest day, but also not the lightest day either, like Friday afternoon.
  • Make sure the team knows ahead of time that you’re going to ask them to escape from the day-to-day during this session, so they can mentally prepare.
  • If you let the team know a blue sky brainstorming session is coming up, I actually find it best not to share what we’re going to brainstorm about. I find that we’re all less likely to come into the brainstorm with an agenda when we don’t know what it’s going to be about.
  • Lead a 2-minute meditation at the beginning of the meeting to help clear their minds. (The first few times you do this, it will probably feel weird. That will pass.)

Try soliciting blind idea submissionsbeforethe session.

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 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.

Play with different meeting structures and prompts.  

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:

  • Try asking for bad ideas first.Use this as a warmup after you illustrate the problem, and take the first five minutes to share out bad ideas only. It’ll get everyone loosened up, laughing, and importantly, actually thinking about the problem. (Thanks, Hubspot, for the tip!)
  • Kate recommendsremoving profitability from the equation and asking: what would the best solution be if we didn’t care about making or even losing money—just making our customers happy?
  • Play with time horizons: ask, what would the best solution be if we had to solve this by next week? What if we had ten years to do it? Take a timed five minutes to solicit ideas for each.
  • Much like pulling a 9 card in Kings Cup, try going around the circlea set number of times—say, five—and asking everyone to share an idea each time, even if they think it’s a bad one. This takes the pressure off trying to make every idea groundbreaking and allows folks to build naturally off of each others’ ideas.
  • Try to set a goal number of ideas to generate, so it doesn’t feel like a destination-less exercise. If your team is particularly busy and you’re asking them to dedicate time to this session, not having a sense of purpose or final goal can make them check out and start itching for their phone.

Identify the constraints you’re working with upfront. 

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:

  • At the beginning of the session, share with your team that unknown constraints will creep into the session. All we can do is be aware of them, verbalize them, let the awareness expand our thinking, and move forward.
  • I think there are some good questions to ask the team to help them get outside of current constraints. ‘If money were no object…’, ‘If time were no object…’ ‘If you could do anything, what would it be?’
  • If you feel like the session is stalling out or you’re collectively stuck, it might be because of a constraint that hasn’t been verbalized or let go before the session. In this case, I find it best to take your last idea and put it through the ‘5 Whys.’ Take the idea and force yourself to answer ‘why?’ after every previous answer.

Build the right foundationsoutsideof the brainstorm. 

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:

  • Stop blaming. Placing blame anywhere signals to people on your team that you’ll blame them for a mistake if you haven’t already.
  • Ask for feedback often. It’s the only way you’ll get better as a manager and it signals to the team that it’s okay to ask for feedback rather than needing to have all the answers.
  • Remind yourself before every conversation (on Zoom, Slack, or otherwise) that the person you’re talking to has a lot of opinions, beliefs, and feelings that aren’t the same as yours. And that you need those differences to be an effective team.

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!