How to Make Agile Work for You

When you think of agile, what do you think of?

Most people think about building a prototype quickly and testing them with users. Once you have feedback, you iterate on your product and test again. It’s about velocity.

Unfortunately,  far too many organizations “go agile” before they deeply understanding the problem they’re solving for. They prioritize speed over everything.

This of course comes at a cost. You can prioritize speed but if you aren’t solving a real problem, your solution will fail. And it’ll likely take many more iterations to get to a viable solution.

So how do you make agile work for you?

Start slow to go fast.

Spend more time defining the problem up front. Use a design thinking process to build empathy and spend time with your customers. Once you have a direction, run a design sprint to align your team and come up with possible solutions to test.

Amazon is famous for going slow to go fast. They clearly define the customer problem through significant customer research. Jeff Bezos was even known for being “The Chief Slowdown Officer” to make sure new ideas were well vetted.

Of course, I’m not recommending spending months and months researching your customers before you launch. You should at least get to a point where you’ve spoken to 5-10 potential customers and understood their core challenges. You may also want to use frameworks such as the Value Proposition Canvas to help you identify the jobs, pains, and gains of your customers.

If you’re looking for ways to test out a new product or idea, I’d love to help. Book a complimentary strategy call here or shoot me an email at

3 Steps to Calibrate Your Product Before Liftoff


If you shift the nose of an airplane by a few degrees, a plane leaving Los Angeles for New York 🗽 will end up in Washington D.C. 🏛️

You probably won’t notice it on the runway. You might not even notice it until you’re in the air. Seemingly small mistakes early on make a big impact on the long-term.

It’s the same with product development.

If you’re not testing and validating your ideas, you’re putting your product and your business at risk. If the average development cost for a quality app ranges between $100,000 to $1,000,000 dollars, that’s a significant investment in resources. Not only that, if you consider the opportunity cost, the true cost of building the wrong product could be much higher in lost revenue.

The good news is that you have the tools to calibrate the direction of your product. It requires more upfront work but it’s better than having to course correct midway, or worse, after you’ve launched your product.

1️⃣ Identify and understand your “best-fit” customers.

If you already have raving fans, spend time with them and have them tell you why they love your product. These “best-fit” customers are who you should be building your product for.

If you don’t have an established customer base, it’s too early to commit to a big build and launch. Take the time to speak with the people you want to serve and seek to understand their challenges intimately as you get ready for the next step.

2️⃣ Prototype and test with real customers.

Spend a week to quickly prototype your idea. The prototype doesn’t have to be a finished or polished version. It just needs to look “real enough” so you can collect meaningful feedback from prospective customers.

3️⃣ Iterate until you’ve met customer needs.

Be prepared to accept that v1 of your prototype might not hit the mark. You’ll need to keep on iterating until you’re able to satisfy your customer’s needs. Make sure you have a process for iteration so you can be consistent with the way you incorporate customer feedback.

You’ve now spent your time understanding your “best-fit” customers, you’ve prototyped multiple times with real customers, you’ve incorporated feedback into your product. Now it’s time to launch with confidence.

Of course, this isn’t the end of it. The product build itself will require adjustments that will involve your product, marketing, and sales team as new information comes in. If building a product that customers love and is like building, flying, and landing a plane, we need all hands on deck.

Write to me in the comments below what challenges you’re facing with building your product, and I’ll send you some suggestions for how you can point it in the right direction.

5 Steps to Get Your Positioning Right

Before you invest money into selling or marketing your product, take the time to figure out your positioning.

You might be thinking… well, I’ve got my messaging and branding down, I’m good to go, right?

Not quite. Positioning is very different from your messaging and branding.

Positioning done right will help inform your marketing and sales messaging downstream. It clarifies how your product is the best in the world at providing some value that a well-defined set of customers care a lot about.

Positioning expert, April Dunford, has an excellent process that I recommend checking out. Here’s a high level of it:

1️⃣ 🛠️ – Competitive Alternatives

First, understand your product’s competitive alternatives. If you didn’t exist, what would people do?

Go beyond just your competitors and include what people will continue to use if they maintain the status quo.

2️⃣ 💪 – Unique Capabilities

Second, clarify your unique capabilities. What have you got that competitors don’t have?

Think about your features and functions that make you unique.

3️⃣ 💵 – Value Generated

Third, figure out the value you create. What’s the impact that your unique capabilities create for customers?

Clarify the tangible and intangible ROI they will get from using your product.

4️⃣ ✂️ – Customer Segment

Fourth, determine the customer segment you’re going after. Who are the actual customers that are a really, really good fit for what we do?

Try to be as specific as you can based on the knowledge, experience, or research you have.

5️⃣ 🥇 – Market Category

Fifth, specify the market category you’re playing in. What is the definition of the market you intend to win?

Think about this from your customer’s perspective. If they were to buy your product under an existing “line item” in their budget, what would it be?

Whether you’re building out a new product or need to reimagine a new pathway for an existing product, take the time to establish your positioning.

Trust me, your sales and marketing team will thank you for it.

For further reading on this topic, I highly recommend April’s fantastic book, Obviously Awesome. 👌💯

The 4 Core Principles of the Design Sprint Process

And how it drives more innovation than meetings.

When it comes to innovation, meetings don’t have a great reputation. Research compiled by TED shows that “50% of people find meetings to be unproductive” and “25% of meetings are spent discussing irrelevant issues.”

There’s real economic impact for bad meetings too. According to the same research from TED, “executives average 23 hours per week in meetings where 7.8 of those hours are unnecessary and poorly run, which is equal to 2 months per year wasted.”

Take a moment to imagine the cumulative impact of wasting 2 months for your team and business (!!)

Underlying the symptoms of ineffective meetings are cognitive biases that are inherent in collaborative work. In particular, I consider the below biases the Four Horsemen of innovation failure:

  1. Confirmation bias – we seek out information that supports what we already believe.
  2. Anchoring bias – we rely too heavily on the first piece of information we receive.
  3. The halo effect – we allow our impression of a person in one domain to influence our overall impression of the person.
  4. Optimism/pessimism bias – we estimate a positive/negative outcome based on our mood.

So how do we organize better meetings that develop better ideas?

Enter the Design Sprint process

The Design Sprint was developed by Google Ventures to prototype and test any idea in just 5 days. Instead of spending weeks or months building something in a vacuum, you validate an idea with real customers within a week. It essentially allows you to fast forward into the future so you don’t waste time and money going down the wrong path.

What’s beautiful about the Design Sprint is that it neutralizes much of the impact of the Four Horsemen by, ahem, design (no pun intended). The creators of the sprint, Jake Knapp and John Zeratsky, thought carefully about the ways to remove biases by creating a process that allows for innovative ideas to emerge.

Without furtherado, here are the 4 core principles of a Design Sprint:

1. Together, Alone

The biggest misconception of innovation is that “group discussions = great ideas.” While group discussions are valuable, they often lead to the most outspoken or senior person – sometimes both – influencing the opinions in the room. 

The biggest misconception of innovation is that “group discussions = great ideas.”

Both of these situations have a chance of triggering cognitive biases such as the anchoring bias (e.g. the first person that speaks steers the discussion in a certain direction) or the halo effect (e.g we allow a senior leader’s expertise in one area to influence our thinking on an area they might not have experience in).

In constrast, when we create time for individual thinking during an innovative process, we level the playing field. It allows introverts to collect their thoughts without being distracted and extroverts to refine their ideas before they share them.

In a famous example, Amazon’s Jeff Bezos is known for providing everyone time to read a memo at the start of a meeting before discussing it. He understands that many on his executive team don’t get a chance to read the memo let alone think deeply about it.

Meanwhile, in a sprint, everyone is given time to brainstorm their own ideas prior to a group conversation. In fact, much of thinking in a sprint is done alone to avoid biases that may arise from sharing ideas too early. Even voting on the best idea is done anonymously.

While it may feel unnatural to be together, yet alone in a group setting, it’s important that everyone gets time to formulate their own ideas and opinions.

2. Tangible > Discussion

Many of us have sat in on meetings where we seemingly get agreement from everyone only to discover that days or weeks later, we need another meeting to clarify what we originally agreed upon! This can be a frustrating time suck and increase tensions within the team.

The second principle, Tangible > Discussion, is to use visuals to help people express and assess ideas. Visuals do three things:

A) It forces the presenter to clarify their idea;

B) It reduces the chance of confusion or miscomunication; and

C) It provides the team an opportunity to build on the original idea and provide tangible feedback.

You don’t have to be an artist to leverage visuals. It can be as simple as a few boxes, circles, stick figures, and/or arrows.

In a sprint, we use exercies such as a Four-Step Sketch or Storyboarding to clarify ideas and share them with the team. These activities create space for participants to flesh out their ideas and visualize them without feeling intimidated about sketching.

So, if you’re sharing an idea or concept in your meeting, try to make it tangible. For example, if there’s a key idea you’d like to walk the team through, sketch it out and share it with the team. If you’re working remoately, you can leverage online whiteboards like Miro or Mural to help you capture key ideas or sketch out a concept for the team.

3. Getting Started > Being Right

I can almost guarantee this is where you’ll get the strongest resistance from your team. As human beings, we seek out information that matches our beliefs. The confirmation bias is real folks!

The challenge for any creative process is how we can solve a problem we’ve never solved before. Relying exclusively on our past experiences or knowledge won’t be enough.

In a sprint, the goal is to move fast and gain momentum. The point isn’t to come up with the perfect prototype but something good enough to test and learn from. We’re essentially placing an educated bet on what we think might work.

[In a Design Sprint], we’re essentially placing an educated bet on what we think might work.

This is where having a reliable process to generate and select the best ideas truly matters. If you have a structured process that allows for unbiased idea generation and selection, your team will likely be more comfortable trusting the best idea to emerge.

The good news is that with a sprint, you’ll be able to see what works and what doesn’t work within 1-2 weeks. So having your own process that provides a rapid feedback loop from idea to testing will give your team more confidence that they’re going in the right direction.

As Eric Ries, author of The Lean Startup, wrote, “the only way to win is to learn faster than anyone else.”

4. Don’t rely on creativity!

The final principle is a little provocative. After all, isn’t innovation all about unleashing people’s creativity?

Yes and no – the truth is probably somewhere in the middle.

Creativity is a fickle thing. Some days we’re in the mood where inspiration strikes like lightning and some days we’d rather be tucked comfortably under the warm covers of our beds.

Don’t rely on creativity is a reminder that we can’t afford to wait for our creative muse to appear in order to do great work. The best way to innovative is by testing and learning then testing and learning some more.

A process like the Design Sprint helps us avoid the optimism and pessimism bias because we’re not relying on our daily mood for inspiration. As a team, we commit to a process that will help us clarify our direction forward.

What’s next?

If there’s one thing I hope you takeaway from this post, it’s that process matters when it comes to designing your collaborative meetings.

As a leader, your role is to orchestrate innovation by providing your team with the space to generate new ideas and synthesize them into an actionable plan. By having clear principles and a process for innovation, you give your team the best chance to innovate.

Whether you’re running an actual Design Sprint or looking to design better meetings, I hope the 4 principles will help you create the space for better ideas to emerge.

If you’re interested in learning more about a Design Sprint, I encourage you to reach out to me for a 25-minute virtual coffee or come out to one of my future workshops to preview a sprint experience.

A Step-by-Step Process to Build Your Customer Profile

“Don’t find customers for your products, find products for your customers.”

– Seth Godin

If you’re responsible for your company’s growth strategy, you probably already know how important it is to have a clear customer profile. When you have an intimate understanding of your customer’s wants and needs, you’re more likely to choose the right strategy to grow your business.

The constant socioeconomic shifts due to new technologies, cultural expectations, demographic changes, etc. also means customer needs are constantly evolving. Many companies have some sort of customer profile but the above shifts mean they might already be outdated.

The global pandemic is a prime example of major disruption that may have shifted your customer’s behaviours. In a very short period of time work-from-home became an employee expectation, and virtual offerings (e.g. classes, events, etc.) became the alternative for in-person activities. If a company didn’t catch onto this change in their customer profile quickly, they would’ve been left behind.

So wherever you are with your customer profile, here are three simple steps to get started:

1. Schedule Five Customer Interviews

As good as your business model may be, it cannot and will not survive forever…That means you must constantly gather information on shifts in your competitive environment, especially those that might affect the behaviour of your primary customer.

– From a Harvard Business Review article Choosing the Right Customer (2014)

That’s right. Just five interviews!

There’s research from the user experience space that shows that testing only five users reveals over 75% of usability issues. Discovering 75% of usability issues gives you a great head start on building the right solutions. You can get more insights from talking to more customers, but you’ll see diminishing levels of return on that time.

Let’s say you schedule five customer interviews for 25-minutes each. That’s slightly over two hours of time spent better understanding current issues customers are facing. It’s little upfront investment for reducing risk and clarifying your value proposition.

If you already have an existing customer base, you’ll have plenty of potential interviewees to choose from. I would suggest selecting those that you believe from your ideal customer base.

To know if a customer is ideal or not, imagine growing your business by 10x the number of customers. Would you want ten times more of that customer? If you answered yes, then you’ve identified a good ideal customer.

If you don’t have an existing customer base, you can invite people in your network for an interview. Think about people who are decision makers in their roles and the type of people you’d love to work with and provide an offering to.

If you’re a B2B company, I would suggest these five interviews to be focused on the key decision maker. If a VP of Sales is your key decision maker, focus on scheduling interviews with people with that title. Uncovering their pain points should be your priority above all else.

Step 1 is complete when you’ve identified your five customers you’re going to talk to. Once you’ve identified those folks, it’s onto Step 2.

2. Prepare Your Interview Questions

Your interview questions likely depend on your product and your relationship with the customer. However, there are some standard questions you can ask. I’ve modified these questions from Value Proposition Design by the Strategyzer group.

There are three key themes you’ll want to cover in your interview:

  1. Responsibilities
  2. Pains
  3. Gains

Responsibilities are the core jobs and tasks that the customer has. It may also include things that might not be in their job descriptions. Here are some sample questions:

  • As the [insert title], could you talk a little bit about the core responsibilities you have?
  • Outside of your expected responsibilities (i.e. your job description) what else do you have to take on? Is there anything that’s surprising you?

Pains are the main issues and challenges they face. The pains usually hinder or prevent the customer from executing a strategy or getting a job done.

  • What are some of the things that frustrate or annoy you the most?
  • What are some of the risks you’ve taken that you were worried about? Are they typically financial, social, or technical risks? Or something else?

Gains are what success looks like for the customer. They’re likely specific goals they need to achieve, or things that allow them to create an ideal environment to be successful.

  • What solutions or ideas really work for you? Why do you think those solutions work well?
  • What would make your life a lot easier? What do you wish you had right now?
  • If money or budget isn’t an issue, what do you dream about doing? What might you invest in?

The questions above should be more than enough to pull some interesting insights from your customers. It’s also important to trust your intuition. If something that your interview said piques your curiosity, you might want to ask a follow-up question to explore an underlying need or challenge that the interviewee has.

The conversation should take around 25 minutes. If you need more time and the interviewee is engaged, it may be appropriate to ask for another 5-10 minutes to wrap-up the interview.

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3. Visualize The Customer Feedback

Once you’ve run at least five customer interviews, it’s time to review and compile the information. The Customer Profile Map from Strategyzer is a good place to organize the information. In addition, in order to organize the information you collect, I suggest using a virtual whiteboard tool like Miro to visualize the map.

The Customer Profile Map from Value Proposition Design by Alex Osterwalder

For each section, I aim for about 12 sticky notes. Sometimes there’s more and sometimes there’s less. As long as you have about 8-12 data points, that should give you a good sense of the customer profile.

Once you’ve conducted five interviews, it’s time to compile the maps into one unifying map. This is where it’s helpful to use a tool like Miro. You can group the stickies into specific themes and create a holistic version of your customer profile.

Example of a completed Customer Profile Map.

Following the above steps will give you a good sense of what are your target customer’s key priorities. So go out there and interact with real customers! Here are a few more quick tips before you start the interview process:

  • Ask if the interviewee might be open to you recording the conversation. This will help you go back to the recording if you missed anything. It’ll also be an opportunity to share direct customer insights to your team.
  • Don’t spend too much time on the customer responsibilities/jobs at the start of the interview. Spend most of your time uncovering the pains and gains.
  • Have one person who is consistently at all your interviews. Ideally this is the project owner for this Customer Profiling project.
  • Wrap-up the interview by asking if they have any favourite resources that they follow or consume (e.g. books, magazines, blogs, thought leaders, etc.) on a regular basis. These are great resources for you to follow as well.

P.S. If you’re looking for help developing a customer profile, I’m happy to help. You can fill out this contact form to schedule a conversation.

Good to Great: The Hedgehog Concept

This post is part of a series on useful business concepts to help build more resilient, innovative companies in the world.

The Hedgehog Concept comes from Jim Collins’ bestseller Good to Great: Why Some Companies Make the Leap and Others Don’t.

In the book, Collins shares insights that his team gathered across five years of research to try to understand what are the universal distinguishing characteristics that cause a company to go from good to great?

The research led him to 28 companies that outperformed the composite index of some of the world’s greatest companies including Coca-Cola, Intel, General Electric, and Merck.

The Hedgehog Concept comes from an ancient Greek parable: “The fox knows many things, but the hedgehog knows one big thing.” Foxes pursue many ends at the same time and see the world in all its complexity while hedgehogs simplify a complex world into a single organizing idea.

The research suggests that great companies are hedgehogs. They’re the companies that can see what is essential, simplify the mission, and ignore the rest.

How do we apply The Hedgehog Concept in our business? Collins shares the diagram below to help companies find their sweet spot:

  1. What you can be the best in the world at (and, equally important, what you cannot be the best in the world at).
  2. What drives your economic engine.
  3. What are you deeply passionate about.

It’s crucial to note that becoming the best in the world is not about willing your way to the top. Just because you had years of success with your core business, doesn’t mean you can be the best in the world. If the market has shifted and the competition pivoted years before you have, it may mean it’s time to make the difficult decision to go down a different path. Great companies were able to realize this sooner than the good comparison companies that Collins studied.

Finding the sweet spot for The Hedgehog Concept isn’t easy. According to Collins, it took four years (!!!) for the good-to-great companies to clarify their Hedgehog Concept. It’s an iterative process and one that will require dialogue, debate, testing, and analysis on what’s working and what’s not with your team.

The Hedgehog Concept is not necessarily a new concept. There are other ideas out there that are similar (The Blue Ocean Strategy, for example) but it’s an important one to bring to the table and have an honest conversation about in your organization.

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Start With Fun When You’re Choosing Your Target Customer

One of the most important things you’ll do early on when you’re designing a go-to-market strategy or launching a new offering is deciding on your target customer.

It’s an important first step because the customer you choose will also dictate how you build your product or service, and the way you market it.

At the same time, I know it can be a challenge to settle down on an ideal customer profile to work with!

If you’re launching something new, you might not have enough information about potential customer needs or you might not want to pigeon hole yourself to the wrong target audience too early.

That said, it’s important to start somewhere and have a hypothesis you’re willing to test. “Spraying and praying” your sales & marketing effort doesn’t work — especially when you’re limited in time, money, and energy.

If you’re having this type of challenge, take a moment and open up your favourite writing tool. I’ve outlined four key questions below to help you get closer to finding your target audience. This activity should take about 30-60 minutes of initial reflection.

1. Who will you have the most fun working with?

You might be wondering why “fun” is at the top of this list. After all, if you’re trying to build a business, and fun really has no place for something so serious… right?

I’d argue that elements like fun, creativity, and joy should be at the top of any important project you take on. In our adult years, we’ll spend more time with our colleagues, teams, and clients than we do with our friends or family (!!!), so why spend that time working with people you don’t genuinely enjoy spending time with?

When you ask yourself this question, an interesting shift happens. Instead of focusing solely on the industry, size of the company, title, etc. of an ideal customer, your focus shifts more to the type of person and organization you’d enjoy working with. In marketing terms, we shift our focus from demographics to psychographics.

When I ask myself this question, a few follow-up questions about my ideal customer emerge:

What are they like? 

What motivates them?

Do they care about the people around them and the culture they build?

Do they value integrity and creativity?

Is the work they do more than just a “job” for them?

Obviously it’s more challenging to find people with a matching mindset than it is to look up someone with a specific title or in a certain industry or company size. 

At the same time, we have more effective tools available these days to attract like-minded people. This blog is a good example of that. If you’ve read my piece this far, it’s likely you care about the same things that I do.

So take a moment to think about the people you might enjoy working with the most. Imagine you have five open seats around a table. If you were to form an advisor panel with these five customers, who would you want in those seats?

2. Who can you create the greatest impact with?

This question is all about the value proposition of your offering.

When you think about impact, what you’re really asking is whether your product or service will solve your customer’s problem. So it’s crucial you spend time developing a solid customer profile and understanding their pains and gains.

Here are the key questions to consider when you start this process:

  1. What jobs are they trying to get done?
  2. What pains are they experiencing?
  3. What gains are they looking for?

If you asked them about their current challenges or concerns, what might they say to the following questions?

  • What are the main difficulties and challenges you encounter? Do you have difficulties getting certain things done, or meet resistance with particular jobs for specific reasons?
  • What do you find too costly for your business? What takes a lot of time, costs too much money, or requires substantial efforts?
  • What negative consequences do you encounter or fear? Are you afraid of a loss of face, power, trust, or status?

On the other side of the ledger, what might they say to things that they want or desire?

  • How do current value propositions delight your customers? Which specific features do they enjoy? What performance and quality do they expect?
  • Which savings would make your customers happy? Which savings in terms of time, money, and effort would they value?
  • What would make your customers’ jobs or lives easier? Could there be a flatter learning curve, more services, or lower costs of ownership?

By going through these questions, you’ll likely get a better picture of whether your product or service will meet the needs for your customers

(For further reading about this topic, I recommend reading Value Proposition Design by Alex Osterwalder for a step-by-step process to create a strong value proposition for your product or service.)

3. Based on your experience, which clients do you understand best?

If you have past experience working in a particular industry or segment, this is a good time to think about where you can leverage this. You already have a good sense of what the challenges look like for this group and you might be able to achieve early success by targeting this group.

One thing I think about is the Blue Ocean Strategy developed by Renee Mauborgne and W. Chan Kim. Instead of fighting for a spot in a highly competitive market (i.e. red ocean) how can you create a unique offering where you create the demand (i.e. blue ocean).

By thinking about the combination of which clients you understand best and mixing it in with a unique offering, you might be able to create a blue ocean for your business.

4. Who would it be most profitable to work with?

Finally, take a moment to think about profitability. 

Insights here could come from your past experience working with different customer segments, research that’s publicly available, conversations with colleagues & peers, or anywhere else you can think of.

Industries that are experiencing substantial change or growth might be a good group to target as they often have unmet needs or opportunities where you can create a Blue Ocean Strategy around.

Profitability doesn’t just mean how much gross revenue you can generate with a customer base. If you have a customer base that’s difficult to work with, you’ll likely be spending a lot of time providing customer support or post-sale services that will eat into your profits.

Which clients will be the most satisfied with your offering just as it is? If customization is required, what parameters can you set so that you’re not modifying every last detail?

Putting It All Together

Whether you’re a leader in Sales & Marketing collaborating with your Product team to create a new offering or you’re an business owner keeping up with new customer demands, it’s important that you nail down the target customer first. I hope the questions above sparked some ideas and thoughts for you to further explore!

Finally, it’s worth keeping in mind that all of this is a balance, and the questions above should encourage you to establish principles rather than rules with who you work with. Principles help guide your decisions and are more adaptable than rules which tend to be more rigid. Regularly working with all parts of your business to keep your ideal customer profile will be important as well as major events or shifts in the market may change the expectations and behaviours of your customer.

What was most useful for you in this article?

What has worked for your business in deciding on a target customer?

I’d love to hear your comments and thoughts below.

P.S. I’m running a workshop on Tuesday, November 10th at 12pm EST to help leaders frame any business challenge. We’ll use fun, interactive activities to help you figure out what your key obstacles are and how you can solve them. If you’re working on any BIG challenge or project, I hope you’ll join me there.

How to Reframe Obstacles as Opportunities for Curiosity

Space is a heck of a place to run into problems.

In the 1995 movie Apollo 13 there’s an iconic scene in which NASA Flight Director, Gene Kranz, (played by Ed Harris) draws a map of the Earth and Moon on a blackboard.

It had been two days into the mission when an oxygen tank failed aboard the spaceship causing an explosion in the main service module. Without the module operating, the crew had to move to the lunar landing module as a lifeboat.

In the scene, Kranz gathers the mission operations team and draws a map of the flight trajectory that the damaged Apollo 13 would need to track to return back to Earth safely. It was a simple map for a complex problem.

Over the course of the next five days they would have to navigate a series of obstacles that required the crew and the mission operations team to find creative solutions. Anything and everything was on the table.

Every time a new problem emerged, Kranz gathered his team around the blackboard to discuss the challenge around their central goal: get the crew back home safely.

Reframing Obstacles as Opportunities for Curiosity

It’s easy to spend a lot of time thinking about what’s going wrong or what could go wrong. But maybe there’s a better way of looking at obstacles? 

In fact, problems themselves can be an opportunity for creativity and innovation. When teams can gain clarity about the problem and break it down into questions to find answers to, we might just create the space for innovation to happen.

Here’s an activity to try with your team at your next (remote) meeting called Starting at the End.

It sounds obvious but one of the most forgotten steps when launching a new project is clarifying the objective. Even taking the first 30-60 minutes of a project to talk through these questions as a group can help clarify the direction and rally your team around a common goal.

Here’s the first question:

  1. Why are we working on this project or problem?

Take your time with this question. Beyond the obvious answers around hitting certain metrics or deliverables, there may be some deeper whys that emerge from you and your team that create an emotional connection to the problem you’re solving. Just like the mission operations team rallied around “get the crew home”, this will be your team’s core motivator.

  1. Where do we want to be 12-18 months from now?

Depending on the scope of the problem, you may want toggle with the timeframe here. Maybe it’s 6 months or even 5 years? Personally, 12-18 months is a sweet spot if you’re looking for a balance between an aspirational goal while also being focused on tangible milestones you want to achieve.

  1. Imagine we travel into the future and our project failed. What caused it to fail? What went wrong?

Now we switch gears. In the first two questions, we painted a picture about what success might look like, but now we want to look at the obstacles in the way.

Note that after you pose this question to the team, it’s natural that the energy in the room might dip. Uncertainty is uncomfortable especially if it’s a project you’re excited about. But it’s important to embrace this tension and make sure everyone in the room has a chance to share what they might be worried about before we move onto the final step.

  1. To reach our goals, what questions do we need answered?

This is the last, and the most important step.

Now that we have a list of challenges we might encounter, we’re going to reframe them into questions. Problems create uncertainty but interesting questions help activate curiosity.

Problems create uncertainty but interesting questions help activate curiosity.

Here’s how you’re going to phrase the questions: “How Might We…” 

How Might We (HMW) questions transform the mindset of your team by helping them consider  the possibilities. We’re all so wired to fix things, but what innovation needs is more curiosity and space to explore. Here are a couple of examples of transforming some existing obstacles & assumptions into HMW questions:

Solving a Big Problem? Consider a Five-Day Design Sprint.

The activity above comes from a process designed by Jake Knapp and John Zeratzky called a Design Sprint. In fact, it’s one of the first activities you’d do in the sprint to gain clarity on what you’re trying to solve.

Here’s what that process looks like:

  1. You spend the first day identifying your goals and mapping the current process for your key stakeholders. 
  2. On the second day you focus on ideating and unleashing your team’s creativity. 
  3. On the third day, you decide on the ONE area you want to prototype a solution for. 
  4. And by the time Friday rolls around you’re actually testing your solution with real clients.

Thinking five days is too short to prototype a new solution? Take this example of an insurance company that condensed 6 months of meetings & discussions to come up with a prototype in 5 days.

The best part is that not only are you reducing risk, you’re saving time. One of the characteristics of the VUCA (volatile, uncertain, complex, and ambiguous) world we live in is that the rules change quickly. If your launch timeline isn’t reaching your audience quickly, the project itself may be too late.

How Are You Thinking About Problems?

On April 17th, 1970 – five days after the launch – Apollo 13 splash downed in the South Pacific. Although fatigued from dehydration, the crew was alive and in good condition. It was an amazing achievement given how dire the situation was only days ago.

It doesn’t take rocket science to figure out how to solve a problem but we do need a good framework to help us get started. If you’re just about to launch a project, give the activity above a shot and see if you can reframe your obstacles into HMW questions. Your team will thank you for the simple switch in the mindset from uncertainty to curiosity.

P.S. I’m running my second workshop on October 23rd for creative leaders (like yourself!) to bring more fun and innovation to solve your BIG problems. Registration is capped at 10 people and the last session sold out. So grab your ticket early and I hope to see you there!

How I Unpacked What I Really Wanted to Do With My Career

For the past few years, I’d had a nagging feeling that the work I’d been doing was not the work I was meant to be doing. I mean, I was pretty good at it and felt generously compensated for it, but it just never felt right. Maybe you’ve felt this before as well. 

After spending a summer of conversations and reflections, I’ve decided to commit to the pivot. I’m calling it the “commivot.” (Okay, maybe there’s a better word for it!)

As anyone who’s made a career pivot before knows, it’s scary. And just that much scarier when it means you’ll be venturing into the world of entrepreneurship.

If one does not know to which port one is sailing, no wind is favourable.


This post is about the process I went through in deciding to make the shift. I’ve been working with an incredible career coach, Andrea Fruhling, Founder of Doubleknot Works, and with her permission, I’ve shared how we created clarity for my next big move.

For those of you who are thinking about making a change, I hope you find this post helpful. It’s a personal account of my experience but I’ve tried to explain the activities so you can do them yourself.

And even if you aren’t in the process of shifting, I hope it helps spark some ideas on how you can craft a career that brings you more creativity and fun.

First, a bit of context.

For a year, I’d been talking to my former employer about the idea of moving on from the organization. The role in sales I’d been in for a couple of years just wasn’t for me. It was scary to talk about it to my boss but she was incredibly supportive of the idea, and we discussed a timeline for my transition.

What’s that saying about plans? Turns out they don’t always go as planned.

Long story short, the timeline was cut short when I was let go in May. As those who have experienced a layoff know this, it’s not easy being let go – even if you’d been planning on moving on at some point. And for a couple of weeks I was licking my wounds and relied on my friends and family for their support as I worked through my emotions.

Deep inside, I knew this was the right thing. Sure, it wasn’t my choice to leave at that time (especially during a global pandemic!) but I was all-in now. I was pushed off the plank and now I had to learn how to swim on my own. As cliche as it sounds, it’s a liberating feeling when you know you have your own destiny in your hands!

Reflection #1: What do you do for fun?

I started to work with Andrea in June. I decided to work with a career coach because I knew the pivoting process wouldn’t be easy. I’d be facing resistance everyday as my “lizard brain” would make me look for the safest and comfortable option. If I was going to commit to this transition, I was going to need help.

One of the first activities we did together was sharing what I do for fun in different situations. Instead of approaching situations in my default way, what if I could make decisions and face challenges in a fun or innovative way?

We looked at all aspects of my life including approaching unemployment, work life, going to the gym, podcasting and blogging, managing my finances, and my relationships. I wrote down what I typically do in my default mode followed by what I’d do if I was approaching it in a fun or innovative way.

What feels fun, creative and innovative for you?

One of the first few questions Andrea Fruhling, my career coach, asked me

As I worked on this list, a few themes emerged about myself:

  • I like variety in challenges and learning something new in the process. (If someone paid me to be a student for life, I’d take that offer in a heartbeat);
  • I enjoy collaborating with other people to identify the root cause of a problem and developing potential solutions;
  • I love the early stages of strategy development – brainstorming, discussing and planning;
  • I enjoy working in small teams that have a high level of trust and collaboration;
  • I love learning and using my discipline (probably my greatest strength) to diligently work towards acquiring a new skill;
  • I enjoy work that’s more “project based” as I get to start fresh with a new challenge I can tangle with.

These realizations weren’t new. I knew many of these things, but it was helpful to write them out and see the patterns emerge on a Google Doc. To add to that, asking myself the question “what work will be fun, innovative and creative for me?” became a powerful question to guide my career planning process.

Inspired by my conversations with my career coach, I mapped out my career journey thus far.

Reflection #2 – Prioritize what matters to you

The second activity that was really useful was ranking my Workplace Attractors. These are elements of work that drive our sense of fulfillment. She walked me through the list below and asked me to rank them in a pyramid structure.

  1. Innovation (doing something new)
  2. Work Fit (finding work that fits my interest, values, etc.)
  3. Relationships (working in a group, interpersonal connections)
  4. Learning (opportunities for growth, professional development, new challenges)
  5. Contribution (sense of purpose and meaning and doing work that has meaning)
  6. Security (financial, having benefits, position security)
  7. Flexibility (time off for other needs and work/life balance)
  8. Recognition (being appreciated for what you’re doing)
  9. Responsibility (being trusted to take on responsibility)
  10. Location (physical space, healthy workspace)

After some back-and-forth, here’s what mine ended up looking like this:

What was surprising to me was how “Work Fit” landed at the very top of the pyramid.

In the past, I’d chosen to work for organizations because I believed in their mission. My first job out of university was in a small town in Mozambique doing microfinance work. I then followed that up working at a youth focused social enterprise. 

Making an impact (i.e. contribution) was an important part of my career story, but it turned into the only story I was telling myself. While I wouldn’t change a thing about my career journey so far, reflecting on this made me realize that I was sacrificing the other attractors for contribution.

So it makes sense that Work Fit now takes the top spot in my career search. I want to do work that lines up with my strengths and skill sets I want to develop. That’s not to say other elements are not important, but it’s important for me to prioritize the ones that will drive the most fulfillment in my next role. This will sustain enjoyment over the long term.

Reflection #3 – Connect emotionally with your path

The third and final activity we did was one that I’ll call “The Perspective Shift.”

Andrea asked me to set up my living room with three separate chairs. Each chair represented a potential career I was interested in. I’d been considering a wide variety of ideas including exploring design thinking, coaching/consulting, taking a mindfulness teacher certification, etc. 

As I sat in each chair, Andrea asked me to share how it felt being in that chair. Going through the process with each career option which allowed me to think about the aspects of work that got me excited. It also brought up potential questions I’d need to answer to better understand each option.

I have to admit, it felt a bit weird doing this activity. There were so many unknowns and it felt uncomfortable to talk about each career option when I hadn’t even taken the first step. Not to mention I’m in my living room talking to myself and a couple of empty chairs.

But looking back, I realized the point of the exercise was to feel what it might be like to commit to a path. We often ignore our feelings in favour of our thoughts. I’m particularly bad at this as I tend to over analyze and forget to trust my gut.

By visualizing what it might be like to go down a path, it helped me uncover a strong interest I had in a concept called design thinking. I didn’t know much about it but I knew it had to do something about using a process/framework for creative problem solving. Based on the “what I do for fun” exercise I had done earlier in this process, the idea of tackling different problems and understanding root causes got me very excited about exploring this topic further.

This is the real secret to life – to be completely engaged with what you are doing in the here and now. And instead of calling it work, realize it is play.

Alan Watts

In weeks following this activity, I took an introductory course on the topic from a leading design thinking agency in the world and started connecting with a variety of people who are in the space.

I was able to start answering the questions I had in my head about this topic and began to build more confidence that this was the right path forward. All it took was a bit of visualization and connecting with my gut feeling to get me started.

Three Key (+ One Bonus) Lessons

So there you have it – three reflections that helped me work through my commivot! There’s a lot that I shared above so I’ve summarized the key lessons learned below:

  1. Discover what your “North Star” is and remind yourself throughout the process. For me, it was about pursuing work that feels fun, creative and innovative. If you put aside making money, what might fun look like to you? If you could design your own role from scratch, what would you do?
  2. Do the Workplace Attractors exercise and stay true to the workplace attractors that are important to you right now. Be mindful of the “career story” that you’re telling yourself. E.g. I studied “x” so I have to be “x”. Many of the most successful people in the world started in a field that had no direct relation to the work they do today.
  3. Invest in a career coach. A good coach will be there to provide a framework, question unhelpful stories about yourself and hold you accountable to taking action. If Michael Jordan had a coach throughout his career, I’m pretty sure we should all have one too.
  4. Finally, be patient with yourself. Arriving at a decision to pivot took me time. Do the exercises, research your options and let your subconscious mind do work in the background. Build the courage to take that first step.

If you’re working on your own career pivot, I hope you found this useful. I’m happy to be a resource if you’d like to talk about it. Please feel free to reach me at

P.S. I’m running my first virtual design thinking workshop on Friday, October 2nd. (Yes, I’m putting my money where my mouth is!) If you’re interested in a simple process to inspire more creativity and collaboration at your next (remote) team meeting, I’m sure you’ll find it useful. You can learn more about the event and purchase your tickets here.

Book Notes | The Courage to be Disliked

By Ichiro Kishimi and Fumitake Koga

ISBN: 1501197274

Year read: 2019

How strongly I recommend it: 10/10

This book is structured as a conversation between a young man and a philosopher. Over five nights they talk and debate the meaning in our lives through the lens of Adlerian psychology. I didn’t know anything about Adlerian psychology until this book but it struck a deep chord in me. If you feel like you’re struggling to find direction in your life or want to establish a clearer framework on how to live a fulfilling life, this book might be for you.


Don’t focus on what I don’t have. Focus on making the most of the equipment that I do have.

My past experiences and traumas don’t have to dictate who I become. I can have the courage to change my own life.

Don’t give myself the excuse that because “I don’t have this or can’t do this” that I’m incapable.

Adlerian psychology differs from Freudian psychology because it denies trauma as a deterministic event in one’s life. We have to deny trauma if we’re going to move forward from them. Not to forget it but to not let it prevent us from having the courage to change.

Being a part of a society means that having interpersonal relationships is unavoidable. We must learn to accept and deal with interpersonal relationships.

Problems in our lives emerge because we avoid or fail to deal properly with interpersonal relationships. And the truth is that we will get hurt in these relationships and will hurt others along the way too.

Knowing this, some people go as far as disliking themselves to avoid interpersonal relationships all together so they won’t get hurt. They give themselves an excuse to dislike others so they won’t get hurt.

Competition cannot be the core of any good relationship. A feeling of inferiority is healthy if that competition is against one’s ideal self rather than a comparison to others.

Part of the feeling of inferiority is accepting the “imperfect me” just as I am. When we’re learning something new – and we’re always learning – we must accept we are imperfect but that we are capable of changing that.

There are two objectives for behaviour: to be self reliant and to live in harmony with society.

There are three categories of interpersonal relationships: “tasks of work”, “tasks of friendship”, and “tasks of love”. We have no choice but to confront them when attempting to live as a social being. These, all together, are our “life tasks”.

One must not seek recognition or reward from others.

One must seek to separate tasks that belong to themselves and others.

The way to separate tasks is to ask yourself, “who ultimately is going to receive the result brought about the choice that is made?”

In addition to knowing who will ultimately receive the results brought about the choice that is made, one must allow others to experience the emotions that come with the separation that is created. You don’t and can’t own the emotions of the other person – that is theirs to experience.

It all starts by building horizontal – not vertical – relationships.

Having worth is about being beneficial to the community around you. Someone who is beneficial to their community is someone who has a concern for others, builds horizontal relationships, and takes the approach of encouragement.

The goal of interpersonal relations is to achieve “community feeling.”

If a relationship can breakdown just because you raise an objection, then it’s not the sort of relationship you should be in in the first place.

People who hold the belief that they are the centre of the world always end up losing their comrades before long.

When you feel like “I am useful to someone” it gives you the courage to live.

You can’t just build a horizontal relationship with one person in your life. Even one vertical relationship can seep through other areas of your life. You must have the courage to assert what needs to be asserted in all relationships in your life.

Self acceptance is about accepting “one’s incapable self”. It’s not about lying to yourself, but it’s also not about simply accepting the fact that you’ll always be incapable. You believe that you can change yourself but you’re not lying to yourself about your current abilities.

The key ingredient to changing your “incapable self”? It’s about courage. We don’t lack ability – we just lack courage to change what we can change.

Affirmative resignation (accepting what you are now but knowing you can change) doesn’t automatically lead to community feeling & contribution to others. The second key concept — confidence in others — is critical to recognize at this point.

From the standpoint of Adlerian psychology, the basis of interpersonal relations is founded not on trust but on confidence. It is believing in others without any set condition whatsoever.

“Doubt” cannot be the foundation of any relationship. Suppose you doubt your colleagues, friends, family, and partner? There’s no doubt they’ll detect your doubt in your voice, eyes, and demeanour. They’ll soon realize that you don’t have confidence in them. Building a positive relationship with that feeling of doubt will almost certainly prevent any deep relationship from forming. This is why we have to start with unconditional confidence in others.

Unconditional confidence is about making the relationship with the other person better and building a horizontal relationship.

The courage to overcome the fear of being taking advantage of comes form self-acceptance. We have two options: to believe or to doubt. If we’re aspiring to see others in the world as comrades, we only have one option that makes sense.

There are two objectives for behaviour: to be self reliant and to live in harmony with society. The two objectives of psychology that support these two behaviours is to consciousness that I do have the ability and the confidence in others.

For a human being, the greatest unhappiness comes from not being able to like oneself. The feeling of being “beneficial to a community” or “being use to someone” is the only way that one can feel like they have self worth.

Happiness is the feeling of contribution. You might never know how you contributed to someone’s life but that’s not important. All we need is the subjective sense that we were useful to someone.

The courage to be normal. This is what must be emphasized rather than the desire to be special.

Life is a series of moments. When we cast a dim light on the past or future, we’re forgetting to appreciate the beauty in what’s happening before our eyes.

If life is a series of moments and the goal is to dance in each moment, the objective isn’t to move forward to a destination in that moment. You’re dancing for the sake of dancing, enjoying it, and being present in that moment.

Life in general has no meaning. We must assign our own meaning to our life.

Adler’s compass – his North Star – is making sure we point ourselves in the direction of “contribution to others”. When we’re making a contribution to others, we’re going in the right direction.

Someone always has to start. Others might not be cooperative but that’s not up to you. I should always be the one to start.

The world is simple, and life is too.