How to Brainstorm New Ideas

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1. Make it safe to contribute ideas
   The best way to do this is encourage risk taking and acknowledge that some ideas will fail and that's acceptable. The people I know who are the most creative are also the most prolific when it comes to idea generation. And some of those ideas are, objectively speaking, total crap. But there are so many good ideas generated in the process, it really doesn't matter.
2. Go for quantity
   One of the basic tenets of brainstorming is that you need to generate a lot of ideas. In order to encourage that, you have to refrain from evaluating ideas during the initial phase. You simply write every idea down, no matter what you think of it, and then try to generate more ideas. You can always winnow down the ideas later on to chose the best ones to work on. But judging raw ideas as they are suggested is the surest way to kill a brainstorming session.
3. Make it a team sport
   Often in meetings there's a tendency to have one person present and others passively watching or worse, critiquing. That's not a good way to generate ideas. Instead, it's better to break up into smaller groups and give them a short period of time (20-30 minutes) and ask them to generate ideas. Then you need to make sure that everyone is contributing. It's a participation sport folks! You're not there to be a spectator. Not only will you generate more and better ideas, people will actually enjoy the meeting and feel that they contributed something.
4. Cross-Pollinate
   Sometimes if all of the people working on a problem are from the same background you'll run out of ideas. Call in someone with a different perspective. When we've done successful brainstorming sessions at offsite meetings, the best ideas come when you mix up groups across disciplines and force people to explore ideas and problems outside of their area of expertise. Invite the salespeople into a product brainstorming session. Heck, invite the finance team. You might get ideas that you'd never get from engineers.
5. Get down from the mountain
   If you find yourself short of creative ideas maybe you're too isolated. Get out of the ivory tower, the executive suite, or from behind your computer screen and get out into the real world. I have found going out to see customers and just asking about their problems is a tremendously useful way to generate ideas. Conferences are also good; you can see what other people are doing and consider how to apply other ideas to the problems you have.
6. Consider it as an experiment
   Sometimes when the stakes are very high, it's easy to end up paralyzed. In those cases, it can be helpful to approach potential solutions as experiments. You test them out for a period of time and then you'll know whether it works or doesn't. In most cases you can "undo" the experiment if it doesn't work out. But be sure to know what you'll measure to know if the experiment is a success. It might be product downloads or new customers acquired, but make sure you have some basis for knowing whether the experiment succeeded or not. And sometimes even if it fails, you'll have learned something you can do differently.
7. Take a break
   This is counter-intuitive, but it's sometimes the best way to break through on a tough problem. If you're too entrenched in a problem its sometimes hard to be objective or open to a radical approach. In those cases, it makes sense to take a break and engage in some other activity. For me, the best way to come up with ideas is to go out for a run by myself and just see what ideas come to me. For other people it might be a walk around the office building, a hike, a bike ride or a leisurely drive. Anything that gets you out of the mode of intense concentration into a more receptive way of thinking will work.
8. Be optimistic
   Sometimes the only difference between achieving success or failure on a problem is the belief that there is a solution and the willingness to continue to make the effort to strive towards it. And every failure along the way is just a stepping stone. Personally, I think it is better to be an optimist in life than a pessimist or even worse, a cynic. Besides, who wants to hang out with a pessimist?

As before, I've stopped this "Top 10" listing short to encourage others to share their observations on how to come up with creative ideas.