A prompter's guide to embracing whimsy

Injecting whimsy unlocks our curiosity, strengthens collaboration and leads to unexpected potential. How to develop a just-try-it mindset with AI.

There’s a lot to be said for the potential of AI as a factor of our mindsets, and not just in whether or not we’re open to adopting it. By playing with the ways in which we process information or approach problems, we encourage non-traditional patterns of thought. The same types of patterns that create a memorable brand (what’s a Google?) or ground-breaking media (really, a movie told out of order?).

But what can that look like practically? Enter: whimsy. Injecting a playful approach now and then opens up layers of benefits, the least of which are extended curiosity and the best of which are foundation-shaking insights.

Let’s talk about whimsy, why we need it, and how we invoke it with the help of AI.

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Key Takeaways

• Being whimsical brings emotional benefits to both individuals (like higher creativity) and groups (stronger relationships)

• Whimsy can be injected into any role or career, where light actions can bring unexpected and outsized benefits

• Shift your mindset to embrace experimentation in AI prompting, using exercises like "Role Reversal" or "Adding Limitations"

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Why do we need whimsy?

For starters, whimsy emphasizes light actions with lower risk and un-guaranteed (but possibly high) reward.

Being whimsical brings emotional benefits by allowing us to:

1. embrace our creative side

2. find joy in the mundane

3. strengthen personal relationships

4. make challenging conversations easier to navigate

5. bank personal good will

6. increase emotional resilience and gain a more positive outlook

Whimsy leads to deeper connections and shared experiences. And the light-hearted nature of it can be a powerful tool to foster inclusive and innovative workplaces.

Sidebar about whimsicality and collaboration

Where collaboration is involved, whimsical acts are, by their very nature, delighters. But if we’re working off stereotype, a sense of levity and creativity can be characterized as “unfocused”.

We can be resistant to that sense of curiosity, especially in the workplace — some groups and cultures unknowingly shut it down when:

• lead collaborators are resistant to change

• we embrace routine for the sake of routine

• they ignore or pushback against emotional verbiage

• those evoking whimsy are stigmatized

As individuals, it falls upon us to stay open and even lead by example. Let’s look at how we can flex the muscles that make us better at indulging the whimsical. But first…

What does whimsy look like?

Here’s what whimsy looks like in different roles. For each case, I’ve also added perceived benefits (split out into best-case and worst-case benefits).

Whimsy in product management

1. Themed Meetings

   • Best Case: Can become infectious and contribute to culture.

   • Worst Case: Makes meetings enjoyable and boosts morale.

2. Creative Roadmaps

   • Best Case: Adds personality to information, and thereby the product.

   • Worst Case: Makes plans more engaging and visually appealing.

Whimsy in software engineering

1. Easter Eggs

   • Best Case: Adds a unique identity to the product and employer brand.

   • Worst Case: Boosts team morale and creates a fun culture.

2. Fun naming conventions

   • Best Case: Creates an “in the know” element that immediately brings in new engineers.

   • Worst Case: Exhibits a creative work environment, aiding in job satisfaction.

Whimsy in marketing

1. Quick-hitting campaigns

   • Best Case: Captures audience attention and creates outsized reach.

   • Worst Case: Your audience’s reaction tells you something new about them.

2. Inside jokes in content

   • Best Case: Increases engagement and brand loyalty for those in the know.

   • Worst Case: Exhibit a sense of personality, add the tension of curiosity.

Whimsy in leadership

1. Inspirational humor

   • Best Case: Humanizes the company and encourages top-down authenticity.

   • Worst Case: Humanizes leadership and sets a positive tone.

2. Fun recognition programs

   • Best Case: Better recruitment pool when invigorated employees share the company.

   • Worst Case: Boosts morale and acknowledges employee efforts.

Exercises to fuel whimsy and curiosity with AI

Whimsy is an underrated superpower in how we lift the potential of AI. And it stems from a simple question: “What if I try this…?”

The beauty of that question is, with AI we can try in seconds. Then we can re-write and try again (in seconds). This act of trying is a step into uncharted territory and uncharted territory brings unexpected (and potentially transformative) results.

How can we manufacture opportunities to be whimsical with AI? Here are five prompt exercises to get you started, all applied to a more basic prompt geared to create a meeting title and agenda.

Create a concise meeting title and agenda given the following meeting objectives.

* Objective 1: [Primary objective]

* Objective 2: [Optional objective]

For my agenda, please create:

1. Meeting Title: Name of the meeting

2. Objectives: The goals of the meeting

3. Agenda: Rough timing breakdown of meeting components

Exercise 1: Role reversal

Take the perspective of someone outside the realm of the task at hand.

Create a concise meeting title and agenda given the following meeting objectives. Please write this agenda as if you are a high school football coach trying to fire up his team at halftime.

* Objective 1: [Primary objective]
* Objective 2: [Optional objective]

For my agenda, please create:

1. Meeting Title: Name of the meeting
2. Objectives: The goals of the meeting
3. Agenda: Rough timing breakdown of meeting components

Exercise 2: Use incongruent formats

Another way to mash up things outside the realm of the expected.

Create a concise meeting title and agenda given the following meeting objectives. When writing the agenda, write it as if you are giving an elevator pitch on Shark Tank.

* Objective 1: [Primary objective]
* Objective 2: [Optional objective]

For my agenda, please create:

1. Meeting Title: Name of the meeting
2. Objectives: The goals of the meeting
3. Agenda: Rough timing breakdown of meeting components

Exercise 3: Introduce a child-like element

Adding more of a child-like perspective can inject a sense of wonder or even simplicity.

Create a concise meeting title and agenda given the following meeting objectives. When writing the agenda, do it with the wonder of a six-year-old who is excited for this meeting.

* Objective 1: [Primary objective]
* Objective 2: [Optional objective]

For my agenda, please create:

1. Meeting Title: Name of the meeting
2. Objectives: The goals of the meeting
3. Agenda: Rough timing breakdown of meeting components

Exercise 4: Add limitations

Limitations can take a lot of forms, but one of my favorite is to restrict it from using words or phrases it might otherwise rely on.

Create a concise meeting title and agenda given the following meeting objectives. When writing the agenda, please do NOT use the following words: "We", "Help", "Positive".

* Objective 1: [Primary objective]
* Objective 2: [Optional objective]

For my agenda, please create:

1. Meeting Title: Name of the meeting
2. Objectives: The goals of the meeting
3. Agenda: Rough timing breakdown of meeting components

Exercise 5: Genre flipping

A great example would be to take the workplace element and flip it on its head.

Create a concise meeting title and agenda given the following meeting objectives. When writing the agenda, please do it as if the meeting is happening in a scene from a mystery movie.

* Objective 1: [Primary objective]
* Objective 2: [Optional objective]

For my agenda, please create:

1. Meeting Title: Name of the meeting
2. Objectives: The goals of the meeting
3. Agenda: Rough timing breakdown of meeting components

These exercises can A) give you a better idea of how prompting and whimsy go together and B) will offer a chance to practice.

The mental barriers to integrating whimsy

Why do we hesitate to be whimsical? That’s an important question. Common things that block us: the desire to conform, fear of failure, perfectionism (or messiness aversion), and equating uncertainty with wasted time.

We can fight these barriers by adopting a test-happy mindset built around fast experimentation. Embrace a test-first mindset by:

• Lightening your expectations

• Staying opened (or even trying) to be surprised

• Leaning into the “what if” scenario

Balance freedom with structure. Redefine the conversation. Keep open to unexpected outcomes. At the end of the day, just try stuff. The more we embrace whimsy, the higher our own threshold for creativity.