Five Innovation Strategies I Use to Brainstorm with CEOs

Ideation requires divergent thinking

Joni Abigail
Feb 16 · 6 min read

I’ve had the good fortune to sidestep the corporate ladder throughout most of my career.

Nevertheless, my preference for nontraditional roles has still provided numerous opportunities to work closely with a number of entrepreneurs and CEOs. My first few jobs fresh out of university were with startups; small team size meant I was in natural proximity to founders, privy to meetings that would have otherwise been above my pay grade.

I didn’t have much industry experience or technical knowledge, and at first I was cast into the role of the token girl in tech, getting shopped out to model products at trade shows. But in the background, I was steadily leveling up my soft skills in strategic thinking and problem-solving. As cliché as it sounds, I learned to ask valuable questions and challenge assumptions, and the founders and directors started paying attention.

Today, those same skills serve me in my ghostwriting assignments for more CEOs and entrepreneurs. A ghostwriter’s job isn’t the straightforward regurgitation of ideas into a coherent format; oftentimes, I act as a sounding board for ideas, and sometimes I actively coach people through problems. I ask unexpected questions, add new perspectives, and find common threads in the bigger picture.

From company vision-planning to product design and marketing campaigns, these are some of the most effective strategies I’ve used to steer conversations towards innovation.

#1 Start by Dreaming Outrageously Big

Too often in strategy meetings (or any type of meeting), the vibe is all-work, no-play. People come together to solve a Very Important Problem or to develop a New Product™ like their lives depend on it. These meetings are unproductive, stale, and a total drag.

First of all, innovation requires risk-taking. When the room is too serious and there’s too much pressure to produce good ideas, people aren’t willing to take risks. Everyone benefits from safe space to dream up silly, outrageous things. Loosen up and have fun.

Second, when you throw out all the rules and constraints, you limber up your brain and make room for new ideas and solutions. How can you think up something new if you operate within the parameters of what you assume is possible?

Ask the impossible, million-dollar questions:

  • What if money were no object?
  • What if technology weren’t a constraint?
  • With all the right contacts, we could ___.
  • How have trends and the industry changed, allowing us to ___?

#2 Draw Everything You Can

Writing is excellent for fully-fledged concepts, but drawing is best when you’re trying to ideate. Here’s why:

Writing is a linear product—a stream of information that moves in one direction and thrives on the logical flow of information. The process of constructing something linear encourages you to focus on how ideas fit into that one-way flow. But when you’re spouting ideas, you don’t know where you want to arrive yet. Ideation requires divergent thinking.

Diagrams and mindmaps are great because you can always add to them, and it’s not a big deal to scribble things out or draw extra arrows. They keep your ideas in a liquid state, which is what you want until you move onto figuring out how to action them; as soon as an idea crystallizes, it’s hard to melt down into raw material again.

#3 Now Put a Frame on It

So you’ve cracked the world wide open and you have your ideas. Now what?

Fear of a blank canvas is a very real phenomenon. Without a brief, people often don’t know where to start; without a plan, they also don’t know where to finish. This is partially why writing prompts are so effective, but the principle applies far beyond artists and writers.

Creativity with too much freedom leads to frills: wasted time and budget, excessive design and features, and still not enough focus. Innovation thrives within constraints — but not the status-quo assumptions you held before the initial brainstorm session.

As innovation thought-leader Marty Neumeier puts it, “A tightly structured brief will generate energy; a wide-open one will drain it . . . A problem well-framed is a problem half-solved.”

This is his four-step formula for framing a problem:

  1. Write a problem statement. Write a brief summary of the problem, and describe what will most likely happen if it goes unsolved.
  2. List the constraints. What creative limitations does the problem present? Are there time limits? Funding limits? A knowledge gap or barrier in technology? These dictate boundaries you’re working within.
  3. List the affordances. These are the creative possibilities that can find gaps in the boundaries you’ve just defined. Who’s on your team or in your network that you can recruit for help? What’s the gap in the market? Can you create the tech that’s causing a barrier? Constraints and affordances work together to help you find all the possible paths through the problem.
  4. Visualize success. The problem statement describes the result of inaction; now describe the outcome of your solution if it’s successful. What do things look like in a year? Five years? Ten?

#4 Use Oblique Strategies

Sometimes when you hit a wall or run into a creative block, the best thing to do is to flip an idea on its head.

Brian Eno and Peter Schmidt, musician and multimedia artist, first published Oblique Strategies in 1975 after talking over some creative roadblocks they were encountering. The product was a deck of cards, each card with an unusual constraint designed to put unexpected parameters on a project so that they could think more laterally about problems that arose.

Here are some examples:

  • Only one element of each kind
  • What would your closest friend do?
  • What to increase? What to reduce?
  • Ask your body
  • Work at a different speed
  • Gardening, not Architecture
  • Honor thy error as a hidden intention
  • Not building a wall; making a brick

You might be wondering what any of that is supposed to mean, but that’s the point. By applying a new constraint to a problem context, your brain has to adapt and come up with a creative response. Eno and Schmidt’s constraints are particularly applicable to music, but you can still apply them or even come up with your own set.

#5 Embrace the Mess

Research shows that mess may actually facilitate creativity, and I’m a big believer in the idea that our physical state often reflects our mental state on some level. In a sterile room, focus becomes singular; in a cluttered room, attention moves to options.

Here’s the way I see it:

You’ve probably heard of or experienced “flow state.” It’s basically when you get really in the zone, do a lot of deep/productive work, and barely notice time passing. But once you break your concentration, it can be hard to get back into it.

Messy artists’ studios and writers’ desks are the preservation of flow state. Everything is left exactly as it was when they were in the middle of their groove. By returning to the same physical space, it’s easier to reenter the same mental space, and they don’t pack up properly until they’re at a good stopping point.

The same is true for business innovation. Startups are chaotic, but that’s how they move so fast. Remember how I said you want to keep your ideas in a liquid state earlier? Startups keep all the balls in the air; larger, older corporations, on the other hand, get so tied up in dotting the i’s and crossing the t’s that they lose momentum

The mess is part of creative work — don’t fight it.

Final Thoughts

It can be daunting to bring these strategies into meetings when you’ve never practiced them before, so start small.

Try them out alone on a personal goal or project; innovation-thinking isn’t only relevant to the business domain. If you had unlimited cash, what would you make or do? What does your ideal network of people look like, and what could they help you with?

Dream big, and go from there. When you learn to let go of assumptions, turn ideas inside out, and find novel ways around creative roadblocks, you can come to solutions you never knew were possible.

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Joni Abigail

Written by

Linguistics nut. Living memoir. Lost and found.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +785K followers.

Joni Abigail

Written by

Linguistics nut. Living memoir. Lost and found.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +785K followers.

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