Over the course of several weeks, I'm showing you how to apply design thinking and principles to your career planning and development. The series of posts so far is here. 

We've gone through the Discovery and Intereprepation phases, gathering information about your career challenge, looking for themes and framing possibilities. Now we enter into the Ideation phase, where you are generating ideas that you could experiment with in the next phase. 

Up to this point, your career design work may have been largely solitary. Although you may have talked to a select group of people to test out some of your assumptions or to gather information, I find that most of the time, people do discovery and interpretation on their own, especially if they are considering some big career moves. 

Ideation or brainstorming, however, is an activity that really benefits from having more minds working on the issue. Other people can bring in different perspectives and experiences and the give and take of a discussion can be very valuable. 

Here's how to tackle Ideation:

1. Invite a core group to help you brainstorm.

The first step is to gather a group to help you brainstorm. Ideally, this is 4-6 people whom you trust. These individuals don't have to be in the same industry or occupation--in fact, it can be beneficial to have some people from very different careers in your group. 

Let them know what you are doing and why you need their help and ask them to give you about 60-90 minutes of their time to help you brainstorm. This article on The Art of Asking has some great advice that you can use to plan for your invitation. 

2. Prepare for your brainstorming session.

Think about what you want to get out of your brainstorming session. Go back to your original challenge statement and to the opportunities you have been identifying and try to come up with some focused brainstorming questions to work with. For example, if you've been thinking about starting up a side business as a way to bring in income, you might have people help you brainstorm about your best options for a side business or refine a specific side gig idea. 

Next, prepare a space to work in. Pull together some flip chart paper and markers and some Post-It note pads. I've also found it can be helpful to have some Play Doh around--there's something about the kinesthetic connection to doing something with your hands that can help people think. And of course snacks--maybe even some wine or beer, depending on the time of day when you're planning your session. 

3. Brainstorm!

Once you get your group together, give them a brief overview of your design challenge, the highlights of what you've been discovering and then introduce your questions. Be careful that you don't get bogged down too much in giving your whole story--just focus on the relevant highlights that will give the group some context for your session together. 

Discuss the rules of brainstorming:

• Defer judgement.
• Encourage wild ideas.
• Build on the ideas of others--think "and," rather than "but."
• Stay focused on topic.
• One conversation at a time so that all ideas are heard.
• Go for quantity.
• Try being visual--how can you sketch your ideas?

Depending on the personalities of your brainstorming partners, it can be helpful to start with a few minutes of quiet brainstorming where people write down some of their initial thoughts and ideas (good for introverts) before you get into brainstorming conversations. 

Keep your brainstorming session to no more than 45-60 minutes (minus the time you spend on the initial problem introduction and the brainstorming guidelines) so that you can maintain the energy.

Try to have fun with it. Move around, laugh, be willing to get a little crazy. Sometimes the best ideas come from what at first seems silly or completely "unrealistic."

As you brainstorm, be sure to document your ideas on the flip chart and/or Post It Notes. Don't be afraid to draw your ideas. Visualizing can be helpful. 

4. Select Promising Ideas

Once you've had a chance to toss around some of your ideas, end your brainstorming session by selecting promising ideas. In the end, of course, the path you choose will be your decision. But it can be helpful to work with your group to get a sense of which ideas have the most energy and opportunity. 

Have the group help you cluster your ideas--maybe there are several related ideas that you can pull together into a more coherent possibility. 

Then talk to your group about your sense of the ideas that are evolving--which ones seem to have some "juice" and feel exciting? Which ones don't feel like they'd work for you? Ask the group to really listen to you talk and to look for where they see you light up and feel passionate. 

Also ask them to push you a little on the ideas that you may dismiss--is it because they really aren't the best ideas or might it be because they would push on your growth edges and maybe seem a little too risky or terrifying? If it's the latter, then maybe they can help you explore some of these concerns. 

End your brainstorming session by summarizing everything you've discussed, being sure to capture all key ideas, questions and thoughts. 

In our next post, we'll talk about finishing up the Ideation phase with a reality check and evolving your idea for the Experimentation phase.