Thinking

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#21: Boost idea generation by 10x with these 6 prompts


Today, I'll share with you 6 powerful generative prompts designed to spark innovation and elevate your team's brainstorming sessions by 10x. I will also share with you 3 steps to facilitate the session with your team.

In today's fast-paced world, fostering creativity within your team is essential for staying ahead. Back in 2010, an IBM survey of 1,500 CEOs revealed that 60% of them identified creativity as the most crucial leadership quality for the future . This underscores the importance of encouraging innovative thinking within our teams to propel our companies forward.

 The Challenge: Mediocre Brainstorming Sessions

Despite the recognized importance of creativity, many brainstorming sessions fall flat. At their worst, they can even turn toxic. Why does this happen? One significant reason is a lack of planning.

Why most brainstorming sessions fail:

  1. lack of clarity on the customer problem to be solved

  2. Using verbs instead of nouns for brainstorming

  3. Lack of generative prompts

  4. Misunderstanding brainstorming as a chaotic shouting match

  5. Stopping too soon and not pushing for quantity

  6. No strategic warmups to shift a team into the right mindset

For this post, I am going to focus on #3: Lack of generative prompts. (I started writing about all 6 but the newsletter got WAY too long.)

 

The Power of Generative Prompts

The success of a brainstorming session hinges on the questions posed to the team. Asking a vague question like, "What ideas do you have?" often results in a deafening silence because it's too broad and unfocused. Instead, consider using targeted, generative prompts to guide the discussion.


6 GENERATIVE PROMPTS TO ELEVATE YOUR BRAINSTORMING SESSIONS

Let’s use a concrete example to showcase the 6 prompts.

Example: Volunteer retention in K-12 classrooms

A few years ago, I worked with a national non-profit focused on increasing the recruitment and retention of volunteers in K-12 classrooms. Their goal was to attract professionals to volunteer and teach students, and they needed fresh ideas to achieve this.

We ran a series of brainstorming sessions, using these six generative prompts to guide our discussions and generate innovative solutions.

 

The 6 Prompts

1. Amplify the Good

What is great about the current experience that we can elevate?

Example: Professionals always enjoy the in-person connection they feel with students. So, we could ask:

How might we enhance the value that professionals feel during their face-to-face contact with students, and create this experience even before they step foot into the classroom?

 

2. Remove the Bad

What is a pain point in the experience? What would happen if we completely removed it? Go for extremes here to push the brainstorming.

Example: Scheduling is always a pain. So, we could ask:

How might we eliminate the need to schedule professionals to volunteer in the classroom altogether?

 

3. Challenge the Status Quo

What is a clear and standard assumption about the experience? How can we challenge it?

Example: Teachers need to be present to manage the classroom. So, we could ask:

How might we create a classroom experience that doesn’t require a teacher's presence?

 

4. Create an Analogy

What are companies or experiences outside of your industry that we can leverage? Who else solves your problem in a similar way?

Example: Many modern software companies use subscription models and tiered services to attract and retain customers. So, we could ask:

How might we retain classroom volunteers similarly to how Netflix keeps users engaged with their streaming services?

 

5. Explore the Opposite

What is something that is true about the experience? What if we did the exact opposite?

Example: Teachers teach students. So we could ask:

How might we make a learning experience where students are in charge of teaching the classroom?

 

6. Use Adjectives

What are powerful adjectives to inspire the experience?

Example: Inspired by Brene Brown’s teachings on vulnerability. So, we could ask:

How might we create a brave and vulnerable classroom management experience?

 

How to facilitate the brainstorming session:

Step 1: Prepare “How Might We” (HMW) questions in advance

Begin by creating a set of "How Might We" (HMW) questions based on the 6 generative prompts. Involve your team members in this process to generate a wide range of questions. Aim to prepare 10-20 HMW questions to ensure you have plenty of options during your session.

Note: the HMW phrasing is very intentional:

  • How: This signals a focus on concrete solutions, moving beyond the abstract or philosophical “Why.”

  • Might: This word invites possibilities and openness, avoiding the pressure of should or must. It emphasizes exploration over finding the "right" answer.

  • We: I didn’t say You or I. This emphasizes teamwork and collective effort, reinforcing that brainstorming is a collaborative process.

Step 2: Brainstorm using one prompt at a time

Allocate 2-5 minutes to brainstorm each HMW question. Display one question prominently on your whiteboard and let the team focus solely on that specific prompt. If a question isn't generating ideas, don't hesitate to switch to another one from your prepared list. Remember - you have 10-20 of them in your back pocket!

Step 3: Schedule regular breaks

Brainstorming can be mentally exhausting. Plan for breaks every 30-40 minutes to maintain high energy levels and creativity. Monitor your team's energy and adjust the schedule as needed to keep everyone fresh and engaged.

 

Summary

"How Might We" prompts are powerful tools for dissecting problems and generating creative solutions. By using these prompts effectively, you can make your brainstorming sessions more productive and reduce the risks of falling into unproductive patterns. Embrace the collective creativity of your team and watch as innovative ideas flow more freely.


Take Action

Now that you have these powerful tools at your disposal, it’s time to put them into practice. Start by preparing your "How Might We" questions and involve your team in this creative process.

Remember, the key to successful brainstorming lies in thoughtful preparation and intentional phrasing. Encourage your team to think broadly and push boundaries. Schedule your next brainstorming session today, and watch as these generative prompts unlock new levels of innovation and creativity within your team.

Don’t just read about it—take action and transform your brainstorming sessions into a powerhouse of ideas!

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#11: Accelerate complex problem-solving through weekly 4hr sprints


I am going to share with you a way to lead internal projects that accelerates problem solving, especially when you need a cross functional group for decision making and evolution.

 

Work rarely gets done in meetings.

Let’s be honest. Real work rarely gets done in meetings. The reality for most people I work with is that they are back to back all day in updates, check-ins, 1:1s, and weekly reports and have to find quiet times in the evening to do the critical, complex thinking. There are other reasons why work rarely gets done in meetings:

  • meetings are usually too short to dig into anything meaningful

  • poor facilitation

  • lack of prep work to drive impactful conversations

  • missing key individuals or customers for input and feedback

So, we have a meeting to decide on next steps and schedule another meeting. And on and on we go. No wonder why so many of us are burned out!

There is a better way: the 4hr sprint.


ACCELERATE COMPLEX PROBLEM-SOLVING THROUGH WEEKLY 4HR SPRINTS

Stop meetings. Start 4hr sprints.

A few years ago, I was working with a 100-year-old manufacturing company that wanted to implement a new internal risk management tool. (I promise you it was a lot more exciting in real life than that 1-liner!)

The idea needed buy-in across Sales, Operations, and Customer Success all with limited capacity and who usually work in siloes.

Old way:

  1. Create a 50 page presentation with the approach.

  2. Go to each VP to sell the idea.

  3. Hire a consulting firm or make an argument for new headcount.

  4. Wait weeks or months to get started.

New way (what we did):

  1. Created a 4hr weekly working session.

  2. Went to each VP to ask for exactly 4hrs/week of time from key team members for 3 weeks. Not a minute more.

  3. Didn’t hire anybody but activated facilitation skills.

  4. Waited 1 week to get started.

 

Inspired by Google Ventures

This isn’t a new concept. The concept of Sprints was popularized by Google Ventures as a 5-day process to go from problem definition to tested ideas with customers.

I love leading a good 5-day sprint. It’s fun, immersive and intense.

It also is impractical for most day to day teams, which is why I prefer a 4hr weekly sprint cadence.

 

Benefits of this approach

  • Reduces context switching: Stops the mental fatigue of constantly switching between problems and context every 30 min

  • Accelerates problem solving: We aren’t waiting for the right meeting or "a workshop" to start evolving the work, we are just starting.

  • Increases team connection: The longer work periods allows people to get to know each other, especially who work in separate teams

  • Increases productivity: This isn't a meeting. we are doing the work, people!

  • Allows for breathing room: Instead of a traditional 5-day sprint that forces ideas in a short period of time, spreading out the work gives space your brain to digest the content from the week before

 

When to use it

I tend to use this approach when:

  1. there is a discrete problem to solve or idea to evolve

  2. you need to bring a cross functional team together

  3. they have limited time to work on the problem

  4. leadership is asking for quick results

  5. you have access to customers/stakeholder for feedback

  6. the team has facilitation skills to lead the process

 

How to design a 4hr sprint

Here is a sample agenda:

Hours 1 and 2: Recaps + Active Problem Solving

30 min: Recaps, strategic warmups and time to connect

Why?: Participants are probably coming from another meeting and need time to fully arrive, get their head into the game, remember past context, and focus on what to expect in the next 4 hours.

90 min: Focused time for problem solving. Design flare, explore or focus frameworks depending on your workshop goal

Why?: Without visual frameworks, you are going to lose people and you risk everyone just talking, no action. Simple fill in the blanks and prompting questions can get people into action. This is also the core of connecting your workshop goal to tactical activities

 

Hour 3: Break + Prep for stakeholder feedback

30 min: Break.

Why?: Because we are humans, not robots. Invite them to spend 5 minutes to make sure there are no fires happening with their other work and encourage a walk, food and hydration. Do the same for yourself.

30 min: Prep for customer/stakeholder feedback

Why? So the team feels just prepared enough with the right questions to ask to evolve the work you just did

 

Hour 4: Stakeholder Feedback + prep for next week, feedback

30 min: customer/stakeholder feedback.

Why?: Reduce the time from creation to constructive feedback to accelerate the work. Don’t wait for another meeting. Invite them into the mess. Show them the unfinished work to evolve your idea. Also, having customers and stakeholders in the room gives a reason for your team to stay the whole time :).

30 min: Debrief on the feedback and make a plan for the next 4 hr Sprint

Why?: Because teams always love the post-feedback chit chat on what they learned. It creates engagement and excitement for the next working session.


Agenda template I always use

Need help creating and managing your agenda? Here is a free Google Sheet template that I have used for 10+ years to design your next workshop. Feel free to steal it, use it and make it better.

 

Results from the 100-year-old manufacturing client

We reduced time to market by 75+%.

When we worked in this way, the 100-year-old manufacturing client would normally get a functional tool in front of their internal customers in 12+ weeks.

We did it in 3.

We got the right team, right facilitation and right prototyping mindset to drive action in days and weeks. Not months or years.

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#06: 3 steps to drive weekly experimentation


Here are 3 strategic steps that propel teams from nervous waiting periods into continuous product development.

Step 1: Anchor to a Learning Goal

Step 2: Design an Experiment

Step 3: Ask for the Evidence

 

You don't need permission from others to get started.

We have all been there. We have a new project at work. There are lots of unknowns and you are unsure how to get started. So, you wait.

  • You wait for direction from the senior leader.

  • You wait for budget approval.

  • You wait until someone tells you that you have a good idea

  • You wait until the “alignment meeting”

  • You wait until the key stakeholder is back from vacation next week

  • You wait for the perfect conditions to get started.

Focus on learning and experimentation instead

There is a better way to activate a team. And it involves new language and behaviors around learning goals and experimentation. Some of the benefits are:

  • Creates action with the team

  • Turns unknowns into knowns

  • Creates a structure for the team during ambiguity

  • Allows for safe risk-taking to build confidence


3 STEPS TO ACCELERATE EVIDENCE-BASED EXPERIMENTS

Step 1: Anchor to a weekly learning goal

Here are 3 examples from projects I am leading/coaching and the blockers I experienced:

Example 1: Governance dashboards: waiting on senior executive buy-in on strategic direction

Example 2: Product Scoping Templates: debate on whether we have the right solution

Example 3: GenAI for Support data: waiting for budget approval from a business stakeholder

At first glance, each scenario would require the team to wait for approval, direction or buy-in. Yes, we need those from leadership but they don’t have to derail us from taking action in the week.

So, instead, ask your team:

What do you want to learn this week?

You can think about your learning goals through the lens of customer desirability, business viability or technical feasibility?

desirability: does your customer/user want it?

viability: is it valuable to the business/organization

feasibility: can you actually make it?

Based on the 3 examples above, here are my learning goals this week:

  1. Governance dashboards: What kind of data do senior executives want to see for their product governance structure? Is this even the right audience?

  2. Product Scoping Templates: Would an internal discovery team find a 1-page template helpful to clarify their product scope?

  3. GenAI for Support data: Can a GenAI solution make the analyst team more efficient?

Framing these questions as learning goals creates a sense of curiosity and wonder. It helps surface the main unknowns in the project or product direction.

Time-boxing it to 7 days sets expectation of the amount of time we, as a team, are going to be thinking about this question.

Once you have the question framed, it is time to take a new approach on how to learn it:

Step 2: Design an experiment to gather evidence

I am very purposeful on the language of experimentation vs ‘the answer.’ Language matters here.

Experiments evoke imagery of a scientist in her lab trying different chemical combinations out to see what works. Trial and Error. Exploration. Making to Learn.

If you recall, all my project examples are waiting for approval or budget, so we have to be scrappy to test our learning goal to keep moving.

What we are trying this week:

Governance Dashboard

Learning Goal: What kind of information do senior executives want to see for their product governance structure? Is this even the right audience?

Experiment: Async message to 2 execs with Excel charts with fake data about their teams and ask them to take an action.

Product Scoping Templates

Learning Goal: Would an internal discovery team find a new 1-page Template helpful to clarify their product scope?

Experiment: A 55 min workshop the following week to get 5 teams to use the new Template and ask for live feedback.

GenAI for Support data

Learning Goal: Can a GenAI solution make the analyst team more efficient with their support database?

Experiment: Take the most popular support question and make up 3 different answers and feed them to analyst to see their reaction.

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Note, all the above examples involve getting some first-hand evidence toward your learning goal. Push your teams to get real data - this is what is going to drive decision making and next iterations of your project or product.

Crafting the right experiment is part art and science. There are lots of frameworks and examples out there.

I am currently using the Say/Do framework in the new book: The Experimentation Field Book

 

Step 3: Ask for the evidence at next week’s meeting

One of two things will happen.

  1. The will run the experiment

  2. They won’t run the experiment

Both are helpful.

If they run the experiment, you have data to talk about! What did you learn? How did it go? Are we on to something? What are we missing? It will be a very constructive meeting and will help inform your next iteration to start back at Step 1: What do we need to learn this next week?

If they don’t run the experiment, you say: "Great! What prevented you from running it?"

Typically, reasons fall into a few categories:

  • No access to data

  • No access to customers/users

  • I didn’t know how (capability)

  • I didn’t have time (capacity)

As the team lead and meeting facilitator, you are now getting weekly evidence to evolve your product or surface team blockers.

Either one is helpful and actionable to de-risk your strategy your idea. 

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