- Part 4 – page 4

What strategic thinking questions work when you don’t know what’s coming in a conversation? Specifically, what can you ask to learn, explore, diagnose, and adapt recommendations, without knowing what opportunities and issues the other party will mention?

I was on a call like that recently. After a month-long gap in chatting, we talked with a client about current initiatives. The call featured new, important news in multiple areas.

During our talk, we identified multiple valuable ideas. While that didn’t surprise me, I ALWAYS appreciate having several solid ideas waiting in the wings. I can share them if no other ideas come to mind. Developing the ideas in advance depends on prior insight into topics or issues. Without that, it falls completely to asking the right strategic thinking questions to stimulate productive ideas.

9 Strategic Thinking Questions to Improv

What strategic thinking questions worked?

Strategic Thinking Questions can help you handle when the more familiar route is closed down.

That was something I asked myself after the call to attempt to turn strategic improv into a more formal script for future calls. Here are the questions (I think) I asked myself during the call to generate ideas:

In a situation with a clear, positive outcome

  • How was the positive outlier different?
  • How or where can we recreate that difference?

When several things all performed well

  • What was the comparable about the things performing similarly well?
  • Who or where can we make more things like that?

Seeking to leverage already-developed capabilities

  • Where might we have a recipe already completed that’s the same or close to the same for a new situation?
  • Are there instances where we’re neglecting things we already know will work?

Seeking to expand the range of active participants

  • Who else can we involve to help us?
  • Who has a self-interested motive to help us now, in exchange for a future opportunity?

Expanding the impact

  • What can we to do to make other parties successful?

This isn’t our first list of improv strategy questions. It probably won’t be our last.

Contact us and let us know what situations demand that YOU are better at strategic thinking question improv. – Mike Brown

FREE Download - 49 Idea Magnet Questions for Attracting Amazing Ideas

Mike Brown

Founder of The Brainzooming Group, and an expert on strategy, creativity, and innovation. Mike is a frequent speaker on innovation, strategic thinking, and social media.

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“Sitting down to think up big ideas is a really great way to freeze your brain out.” That’s so true. It’s also how author and entrepreneur, John Jantsch, introduced his Duct Tape Marketing podcast where we discussed Idea Magnets, powerful creative thinking questions, and the path to amazing ideas.

John Jantsch has been a marketing icon for years, and a personal model for me since before I started The Brainzooming Group. While still in the corporate world, my career coach, Kathryn Lorenzen, pointed me toward John’s work with Duct Tape Marketing. As a fellow-Kansas Citian, Kathryn said to look at how John was building writing into an entire business model.

Discussing Creative Thinking, Big Business Ideas, and Idea Magnets on the Duct Tape Marketing podcast.

Since that time, John’s reach and impact through Duct Tape Marketing have continued to grow dramatically:

  • Forbes has chosen the Duct Tape Marketing blog as a favorite for marketing and small business
  • John’s Duct Tape Marketing podcast is a top ten marketing show on iTunes
  • The Wall St. Journal, New York Times, and CNNMoney frequently cite John’s perspectives on small business
  • Duct Tape Marketing trains and licenses independent marketing consultants, coaches and agencies on the use of its system around the world

Given all that, I was incredibly honored when John reached out to feature Idea Magnets – 7 Strategies for Cultivating & Attracting Creative Business Leaders on his podcast.

Listen to Mike Brown discuss Amazing Ideas on the Duct Tape Marketing Podcast
During the show, we discussed:

  • The difference between being creative and having a creative thinking process
  • Ways to build a team (whether formally or informally) with all the attributes to generate amazing ideas
  • Using targeted questions to achieve the impact you are looking for in leadership and business

Listen to our fast-paced conversation and get a new take on Idea Magnets, creative thinking, and how you can use questions to inspire and implement for impact! – Mike Brown

Buy Idea Magnets on Amazon

Mike Brown

Founder of The Brainzooming Group, and an expert on strategy, creativity, and innovation. Mike is a frequent speaker on innovation, strategic thinking, and social media.

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I’m fascinated with how to expand your creative thinking skills through powerful questions. My fascination goes back years. Since starting Brainzooming, we’ve especially seen how the right questions make it easier for people to generate ideas they wouldn’t otherwise imagine.

While working by myself on our marketing plan, I realized a new way to think about creative thinking questions. When you don’t have anyone around to help push your thinking, creative thinking questions stand in for the person who routinely asks, “Hey, have you thought about it THIS way?”

When I was a corporate marketing VP, multiple people would dependably and constructively challenge my thinking. Some were co-workers; others worked at our advertising agency or were freelancers in our marketing department. No matter where they lived organizationally, asking me if I’d thought about something in a different way was ALWAYS valuable.

Questions provide detours to your creative thinking skills, routing them in new ways.

As an entrepreneur, you don’t necessarily have a big team to engage for creative thinking. That’s where, when you are working solo, the right question can stretch your creative thinking in dramatic directions. A question can be the perfect vehicle to challenge and expand your thinking in highly productive ways. I think of great questions as providing detours to creativity and strategic thinking. They make you go a different route than you’d originally considered.

Are you recharging your creative thinking skills with these new questions?

Energize creative thinking skills with 49 powerful questions for amazing ideas.

If you could use the help of a surrogate for that Have you thought about it THIS way person, download a FREE copy of our latest Idea Magnets eBook with questions to lead to amazing ideas.

We developed the questions in the eBook from our experiences with Brainzooming clients and studying creative thinking skills of well-known innovators. These creative thinking questions will stretch, shift, constrain, exaggerate, and re-orient your thinking to help you boost your creativity, EVEN IF you are working all by yourself.

I’d love for you to enjoy the benefits of the same resource we’re using to grow our business!

And when you get 49 Questions, let us know how you put it to work  to boost your creative thinking skills!  – Mike Brown


Mike Brown

Founder of The Brainzooming Group, and an expert on strategy, creativity, and innovation. Mike is a frequent speaker on innovation, strategic thinking, and social media.

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“On Monday, we’re having our meeting. It’s like D-Day to decide what happens next. I’m thinking about how to manage the conversation. I wondered if there were a better way to ask, ‘What do you think should happen next?’ other than asking ‘What do you think should happen next?’” That message was on my phone at 10:39 p.m. Sunday evening. It is from a friend and client. She’s staring down a strategic conversation with her board today.

The important strategy question?

Keeping the organization’s core initiative going, changing it dramatically, or shutting it down.

4 Ideas for Managing a Critical Strategic Conversation

Managing a critical strategic conversation is something to plan for in advance.

To answer her question, there are four ideas for structuring the critical strategic conversation on what the initiative’s future should be.

1. Gain a sense of individual perspectives before the critical strategic conversation.

I always want to understand upfront what each person is thinking. We use this information to shape the discussion. You can gain early insights through personal conversations, surveys, or online collaboration (where the entire group is participating but not seeing others’ answers). If something prevents developing that early understanding, I’d design the group’s strategic conversation to gain a sense of individual perspectives before group discussion happens.

One way? Create a worksheet or exercise with several questions that individuals complete at the start. After recording individual ideas, then they share their input. From the initial written perspectives, you can understand and manage how perspectives change during the meeting. You may also get a true sense of perspectives before hearing others’ views changes what people are willing to say in the meeting.

2. Address potential biases early, if possible.

Group members may make assumptions or believe certain things are so important or so harmful. These beliefs may bias their perspectives. If possible, remove these points. In this situation, the person asking the big strategy question will likely exit the organization based on the group’s decision. That could bias certain peoples’ perspectives. She’s already addressed by providing a pre-determined time window for her departure. Nobody need worry about the decision forcing her out of a position she hoped to remain in for years. Diffusing bias points can free up the strategy conversation dramatically.

3. Split the group into smaller ones with similar perspectives.

If the group is clearly divided, split it into smaller groups sharing share similar viewpoints (in this case, perhaps, groups that have landed on continuing, dramatically changing, or stopping the major initiative). Ask them to collaborate and recommend a course of action for their assigned scenario. Have them briefly describe their recommendation, the rationale (including upsides and risks), any assumptions they’re making, what they think will have to be done to start implementing the recommendations, and critical success factors. Doing this before full-fledged group discussion can create a physical representation of the recommendations. This physical depiction (perhaps on flip charts) leads to a more clear and concrete strategic conversation.

4. See if recommendations change as the scenario changes.

After gaining the individual or small group perspectives, describe a few variations in the scenario. See what happens if the personal stakes or other big factors change. Potential variations you could pose in question form include:

  • What if you had to devote 50% more time than now to accomplish this recommendation?
  • Suppose you had to raise money for this recommendation?
  • What if the initiative’s leadership had to change?
  • Would you be willing to invest two years to accomplish your recommendation?

There you have it.

You have an insider’s view of our phone conversation today. You also have a resource for the next time you must manage a critical strategic conversation that feels like your organization’s D-Day. – Mike Brown

Looking for Fresh Insights to Drive Strategy?

Download our FREE eBook: Reimagining the SWOT Analysis


“Strategic Thinking Exercises: Reimagining the SWOT Analysis” features eleven ideas for adapting, stretching, and reinvigorating how you see your brand’s strengths, weaknesses, opportunities, and threats.

Whether you are just starting your strategy or think you are well down the path, you can use this eBook to:

  • Engage your team
  • Stimulate fresh thinking
  • Make sure your strategy is addressing typically overlooked opportunities and threats

Written simply and directly with a focus on enlivening one of the most familiar strategic thinking exercises, “Reimagining the SWOT Analysis” will be a go-to resource for stronger strategic insights!

Download Your FREE eBook! 11 Ways to Reimagine Your SWOT Analysis

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Mike Brown

Founder of The Brainzooming Group, and an expert on strategy, creativity, and innovation. Mike is a frequent speaker on innovation, strategic thinking, and social media.

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How are you doing, doldrums-wise? Do you feel like you’ve lost your business mojo and aren’t sure about ideas for getting your mojo back?

If that describes where you are right now, here is a bit of good news. Based on multiple conversations we’ve had with business people in their 30s to 50s, you are not alone.

The common refrain: I’m working my butt off, I’m continually crazy-busy, but never feel as if I’m doing great work. I’m getting by, that’s all; and I’m wondering what the point is.

Not surprisingly, the concerns we hear are decade-specific:

  • Thirty-somethings are wondering what the work, the stress, and the anxiety are about — and whether any of it is worthwhile.
  • Those in their forties are looking at automation’s threat. They are trying to determine how long it is before AI and robots replace them and stay a few steps ahead.
  • The nearly universal concern for the fifty-year-old group? Whether they have a hope of staying relevant through the rest of their careers as everything constantly changes.

Quibble with the specifics if you must. But consider for a moment the people you know in the workforce. Don’t these sentiments hold up?

Ideas for Getting Your Mojo Back by Decade

getting your mojo back and being a star in your career

It seems everywhere that the pace is faster, expectations are always rising, and it’s challenging to deliver and celebrate stellar work. Too often, it can seem as if you’ve become so focused on shipping that raising the bar gets shuffled to the bottom of the pile—and sometimes, it’s more about swerving to avoid crashing into the bar.

What can you do?

For starters, here is our been-there-done-it-for-years advice by decade for getting your mojo back.

30-Somethings: Focusing on What Matters to You

One way to bring meaning to your work? Look inward for the meaning and direction that don’t seem to exist in the swirl of work craziness around you. When you anchor your professional course to what matters in your life, you can better make deliberate career decisions that stay true to your priorities.

It may sound like a ridiculous prospect. But we have a lot of personal data to back it up, and two things are crucial for making the strategy work:

  1. Knowing what’s most important for you to accomplish to excite and motivate you
  2. Actively creating the flexibility and diversity to allow yourself control over your career’s through-line

When it comes to identifying what’s personally important, mine questions such as these for potential answers:

  • What motivates you every day?
  • Where do you find the greatest joy, fulfillment, and contentment?
  • What long-lasting, significant things do you want to accomplish?

Relative to maximizing your flexibility and diversity, think through:

  • What are the smartest / most fruitful intersections of what’s important to me, my skill set, and market needs? (Venn diagrams are useful here.)
  • What skills might I need to develop for the next thing I’ll do after this job?
  • How can I manage my finances to give me the strongest possibilities to leave a regular paycheck behind temporarily if a job pushes me away from what matters for me?

Combining a clear view of where you want to head with the agility to quickly make big changes prepares you to make career moves that maximize personal fulfillment and minimize the anxiety of figuring out where your next paycheck will come from.

40-Somethings: Staying Ahead of the Neighbors (aka Bill “Robot” Jones)

When the dinosaurs walked the earth (okay, really when the 1800s turned into the 1900s), a major league baseball player named Willie Keeler uttered his memorable success formula, “Keep your eye on the ball and hit ‘em where they ain’t.”

While Keeler didn’t have a clue about AI, his advice is brilliant when devising a personal strategy to stay ahead of robotics and automation. Futurist Bernard Marr, in a Forbes online article, shares a two-part future career strategy:

  1. Look ahead to where automation is headed
  2. Develop (soft) skills in the areas where robots and AI will struggle to perform for the foreseeable future.

One quick test Marr offers to identify where humans will continue to retain an edge over automation (according to Stanford’s Andrew Ng): mental tasks that take the average human more than one second to complete.

If your job requires mental complexity beyond simple THIS-input-leads-to-THAT-output functions, you’re on stronger footing.

When it comes to areas where bots will struggle, Marr suggests developing any of these skills:

  • Empathetic personal communication
  • Critical and strategic thinking
  • Vision, creativity, and imagination
  • Technology management and maintenance
  • Personal physical skills

Want to go deeper in rethinking what you can do? Intriguingly, the skills Marr outlines are very close to the list of strategies in Idea Magnets – 7 Strategies for Attracting and Cultivating Creative Business Leaders. Maybe TODAY is the day to finally get your copy on Amazon and jump start retooling your career.

50-Somethings: Clarify What You Are Giving Up

In your fourth or fifth career decade, you were expecting (we know) a senior-level job that would let you coast to retirement. If you have that, WHOA! Good for you!

But if you realize that the careers you studied in school no longer exist, you have a big decision to make: Are you going to go out loudly or quietly? (Please note: by “loudly,” we don’t mean “complaining ceaselessly about how hard you work at your age and how everything needs to stop changing because it’s inconvenient.”)

getting your mojo back doesn't involve blah-blah-blahing about things changing

Going out loudly means actively and enthusiastically embracing the learning you need to stay relevant for the next ten to twenty years. And that simply will not be one-and-done learning; it will involve perpetual updating and adaptation.

How will you free up the time and mental space for that? Answer two questions:

  • Ask people in the workplace (and maybe at home) who will be brutally honest: What behaviors and practices do you see me doing that don’t really contribute highly meaningful value any longer?
  • Ask yourself: What things have I said for years that I want to do, but haven’t done, and now know that I’m never going to ever do?

Take your answers and give up on those things. This will create room to throw yourself into the new learning and development you must do to stay relevant into your sixties and seventies.

Take Action

Yes, last year moved by frantically fast. This year will be exactly the same. Identify your most significant career anxiety source. Craft a simple strategy to re-energize and get closer to back on top ASAP.  – Mike Brown


Mike Brown

Founder of The Brainzooming Group, and an expert on strategy, creativity, and innovation. Mike is a frequent speaker on innovation, strategic thinking, and social media.

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Were you bombarded with emails in the last week all about coming up with your special focus word, personal exploration, or individual success plan for the new year?

EVERYONE seemed to be on the same program based on our anxiety about hitting the ground running with the simplest way to focus our attention throughout the year. One email even offered an automated word-of-the-year generator, just in case you are unable to imagine a word to shape the next 12 months.

creative thinking questions can target your focus areas for the year

The reason I don’t immediately unsubscribe from these emails? When it comes to focus and preparation exercises, it’s a numbers game. You look at a lot of them, a couple resonate, you follow up on maybe one or two, and you hope that something sticks from the reflection you do. The more of them you have hitting your inbox, the more likely you are to do SOMETHING beneficial, even if it’s basic.

How about Creative Thinking Questions?

What are we suggesting for looking ahead this week to map your professional horizons for the year?

Planning we did in December for Idea Magnets helped identify what I thought might be valuable. Since it’s tough for planners to do their own planning, I turned it over to Tara Baukus Mello to pick the approach we used to plan.

To prepare for the in-person planning, Tara forwarded creative thinking questions that looked out from today to more than a decade into the future. It was twenty pages of questions. While the document was daunting, working with a fresh set of questions forced me to think about completely new opportunities and issues. And that’s always the goal with strong set of creative thinking questions: to push you to explore important (often overly-familiar) areas more deeply and with fresh thinking.

8 Creative Thinking Questions to Focus Your Year

Tara’s exercise prompted me to adapt the eight questions below from our free eBook, 49 Idea Magnet Questions to Attract Amazing Ideas. This subset provides a helpful way to focus in particularly on what’s important for the year ahead.

Spend a few minutes with the questions and record your initial thoughts. Come back to them early next week to see if you’d expand or modify your answers.

  1. If I’m always working with the same people, what can I do each day to increase the diversity of individuals I interact with to stimulate new thinking?
  2. What is something that everyone in our industry has known for years would provide great value for customers that nobody has ever done that we can do in 2019?
  3. What are the boldest moves I can imagine challenging ourselves with in 2019? (Are they bold ENOUGH? Just checking.)
  4. What can we do to reduce by 1/3 or 1/2 the list of projects and activities that seem important but are genuinely blocking greater future success?
  5. What’s stopping us from asking for favors and help from people that we have no business trying to talk to?
  6. How can I better address a big problem by undoing the problem instead of putting another fix on a previous fix?
  7. What scary and risky things did we say Yes to in 2018? Which ones do we need to say Yes to in 2019?
  8. If I wrote the year-end recap for 2019 right now, what dramatic expectations would it point to that we need to address this year?

What’s Next?

After you’ve completed a couple of passes through the questions, then what?

That depends on what will work best for you to stay on top of goals and strategies.

I recommend placing the list in as many places (physically, electronically, and/or mentally) as necessary so that you regularly and frequently see your answers for a quick read. Doing this helps to refresh your memory without trying to be overly beholden to early January thinking that may very naturally need to change over the course of 2019. Yet even if it does, you’ll have a sense of the direction you started with at the start of the year!

If you want the OTHER 41 questions, grab your free copy of 49 Idea Magnet Questions to Attract Amazing Ideas for questions you can use and return to throughout the year. – Mike Brown

FREE Download - 49 Idea Magnet Questions for Attracting Amazing Ideas

Mike Brown

Founder of The Brainzooming Group, and an expert on strategy, creativity, and innovation. Mike is a frequent speaker on innovation, strategic thinking, and social media.

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I surprised a CMO the other day, telling her something she was NOT expecting to read in an introductory email. Here’s the story.

A long-time friend was making an introduction between one of her current clients and me. The focus was her firm needing to develop its brand strategy. Following up the initial email exchange, I shared this:

“If you are looking to accelerate branding development, we use a streamlined process that is highly collaborative. This lets you, as the brand owner, actively participate in shaping the innovative, on-target strategy and implementation plan. Our approach isn’t tailored for every company. Should you want to explore how our branding development approach might work, we’d welcome a call to explore possibilities, if you see that as a logical next step.”

She emailed back within minutes, wanting to clarify if I REALLY meant to write that our approach ISN’T for every company. If that were the case, she said she was very intrigued.

Brainzooming Isn’t for Everyone

I responded to her question:

“Our approach to fun strategic planning ISN’T tailored for every organization. Let me explain.

“I created what became Brainzooming while I was on the client side. We wanted to be highly-engaged with our outside strategy partners. They wanted to maintain a black box approach, however, sucking all the information from us, then retreating by themselves to dream up “creative” branding ideas. We wasted significant time briefing agencies on our strategy only to find our knowledge about customers and markets didn’t translate to the branding work they presented. Then, we’d have to redo what they’d done.

“Because I grew up on the client side, we have tremendous respect and appreciation for the insights that exist within an organization. That’s why our approach is all about collaborating with a client’s management group, broader team, and even outside audiences to build on their understanding. We bring our experience, tools, and time-efficient process to the table. Combined with the brand’s initial insights, it’s a potent combination for on-target strategy.

For organizations that valuable broad collaboration, we deliver fantastic results. For management teams that simply want an outside partner to go off and come up with all the ideas and pitch them, we aren’t a good fit.”

A Fun strategic planning process isn't for everyone.

Why am I sharing this?

I don’t typically write much about what we do for clients because I realize that’s not why you read Brainzooming articles.

Yet, many executives have been beating their heads against the wall trying to more actively engage their employees and customers to shape strategy. They can’t find partners who get that vision and want to collaborate to make it happen. We know that, because that initially describes almost EVERY Brainzooming client.

This probably doesn’t sound like your exact situation.

If it does describe your frustration with being unable to develop strategy in a new way, then you owe it to yourself to contact us for a chat – sooner than later.

Helping executives engage their most important audiences in developing better, more on-target, and highly actionable strategies is at the very heart of what we do very well. We can end your frustrations. Plus, it will be fun for you – and your team. I guarantee that! 

You can email me at Mike.brown@brainzooming.com, call me at 816-509-5320, or reply here. Let’s start making your vision come to life – now!


fun-ideas-strategic-planning11 Ideas to Create a Fun Strategic Planning Process!

Yes, your strategic planning process can be fun . . . if you know the right ways to liven it up while still developing solid strategies! If you’re intrigued by the possibilities, download our FREE eBook, “11 Fun Ideas for Strategic Planning.”

Download Your FREE eBook! 11 Fun Ideas for Strategic Planning

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Mike Brown

Founder of The Brainzooming Group, and an expert on strategy, creativity, and innovation. Mike is a frequent speaker on innovation, strategic thinking, and social media.

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