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  • Writer's pictureDarren Cody

Embracing The Uncomfortable: There Are Stupid Questions. Yes, You Have To Ask Them


Picture it: a meeting room buzzing with developers, and amid coding discussions, I blurted out a seemingly ridiculous question. 'Hey SCRUM Master (Peter), what the hell does a Poker Party have to do with us coding these new requirements? We can drink and smoke cigars while I take your money after work.' Cue laughter from everyone in the room, including myself. Little did I know, that 'stupid' question would become a pivotal moment in my journey as a non-technical Product Manager.

  1. I was non-technical and had never worked with developers before that first year

  2. I unknowingly asked a very important question for a Product Mangaer to understand fundamentally.

  3. Everyone in the room laughed.

This moment, one year into my role, encapsulated the essence of my journey – from being a non-technical newcomer to embracing the uncomfortable. I was navigating uncharted waters, having never worked with developers before, and this question unwittingly propelled me into a 'new' comfort zone, one that was undeniably uncomfortable but necessary for my growth.

Even though the timing was inappropriate to ask what a “Poker Party” has to do with our Backlog Planning meeting, I was politely explained that Poker Planning has to do with Agile Development Method. All (or some) of the Developers working on this project would estimate the size of the requirements based on a point system, typically using the Fibonacci Sequence, which refers to the level of effort.

A more senior developer will play a 3 for a User Story or Epic, and a more Junior will play an 8. Everyone doesn’t know who plays what number except for the Organizer who will accept the estimate of effort, provided everyone has the same guess, and if now, per our example, a discussion will begin to address the suspicions of it taking longer or quicker.

I wanted to write this blog post after speaking with both potential and current clients at Marketplace Studio because the common theme is the lack of understanding from a technical point of view and a few cases of lack of confidence. 

Whether you are or choose to work at Marketplace Studio or another agency or hire your own, I believe it is important to gain the skill of constantly forcing yourself out of your comfort zone. 

Before continuing, let’s reflect and recall a memory of when someone in a group of people you were with had asked a ‘stupid’ question.

  1. What was your response to that person?

  2. How would you feel if you had that reaction?

  3. How do you create a work culture that invites ‘stupid’ questions by reframing it as someone being engaged and curious about a given topic?

My Journey: From Declining to Embracing the Role of Product Manager

Short story, short – I was non-technical and lacked the confidence to lead Product, let alone a Dev team. Yet, here I am, Darren Cody, Co-Founder at Marketplace Studio, once a Cold Caller terrified to interrupt strangers' workdays. I've navigated roles from SDR to Account Executive, revealing the power of stepping out of my comfort zone.

In 2014, as an SDR, I faced rejection and harsh responses daily, being told to “fuck off” or to “kill myself”. It wasn't pleasant, but it taught me a valuable lesson – the world doesn't end with an unannounced call. This discomfort pushed me to manage SDR teams and eventually become an Account Executive. However, 'Darren Honest,' as my colleagues dubbed me, meant demoing competitors' software when it was a better fit. My manager did not appreciate it as much as those lost sales did.

Shifting to Customer Support, I gained a crucial skill: User Empathy. Handling live chats akin to a screamed-in pillow, I felt the impact of every bug or urgent update. This laid the foundation for my journey as a Product Manager.

Fast forward, I was offered the role of Product Manager and Development Manager at a rent-anything marketplace. Initially declining, I embraced the challenge, armed with fundamental knowledge and a determination to learn on my feet. I became a green sponge, unafraid to ask 'stupid' questions, to learn, fail, and iterate.

Google became my sword and shield (GPT/Bing - Please take advantage of these!). Every conversation, every private Slack chat with devs that I could be looped in on, I soaked up knowledge. It wasn’t easy, constantly having the compelling feeling of being an imposter, but it is my testament to the transformative power of embracing discomfort.

Fun Fact: Killing Your Ego Makes You Uncomfortable & Vulnerable 

First, no matter how much you know, how smart you are, the size of your budget, and the time you have, your first production launch will NEVER be what the market 'wants.' In the following lines, we explore the discomfort and vulnerability of navigating assumptions, ego, and the invaluable lessons learned during those initial product development stages. Let's dive into the unpredictable journey of building a marketplace and the transformative power of setting aside ego for evidence and insights.

With my strong domain expertise in the rental industry, I believed I knew and understood exactly what needed to be designed, what questions to ask, and how to build our mobile app. Yes, you can laugh, or gasp because you’re doing this now. 

Let’s just say, we launched an MVP with little User Testing, Persona Insights, or integrated adoption analysis tools to even know how ‘great’ it was post-launch. I’m sure you can guess how it went. 

For our first booking, on the fresh recently-debuted, and anticipated app, I had to first explain (in person) how to rent an item, and then basically did it for the User. Yes, not the best start! Did that make me reflect on my decisions or was my ego at an all-time high to not prioritize a thorough investigation? 

Eventually, we would come to understand after embedding Pendo into the mobile app that our funnel conversions were not as great as we expected. 

I assumed that because a large, successful marketplace for short-term rentals had a 21-step process for listing a property, people would invest a similar amount of effort, time, and patience into listing a $50 item for rent. Well, the ROI is not the same, we can leave it there but to be clear, people did not convert as well as expected until V2 rolled out. That was a game-changer.

Soon, we were introduced to Design Thinking, a methodology of building a product that essentially leaves everyone’s ego in jail during the duration of the Sprint and lets evidence and insights dictate the way the product is designed and later developed. 

I had to understand that I was not building this marketplace for me; my wants or my needs. Even expected our Users to have the same understanding or assumptions as me because I was highly knowledgeable in that domain. No. That isn’t how Product Management is done, at least what I’ve come to learn for me. 

The marketplace is a business, a business requires an instream of revenue to stay operational. People providing the money need to be prioritized above internal egos. However, having a fine-tuned Product Vision and Strategy will lay this to rest. 

Unraveling the Unknown: Navigating 'Stupid' Questions in Design Thinking

Climbing the st of innovation requires a willingness to explore the unfamiliar, question the unquestioned, and, yes, embrace the uncomfortable. In our journey through Design Thinking, we unravel the power of 'stupid' questions as guiding beacons, transforming uncertainty into opportunity. Let's traverse this uncharted territory together, where discomfort becomes the catalyst for profound insights and groundbreaking solutions.

Design Thinking Sprint Steps:

  1. Emphasize

  2. Immerse yourself in the user's experience of creating a listing. Conduct interviews, observe user behavior, and gather insights to understand their needs, pain points, and motivations. Create Primary User Persona Cards based on the identified user archetypes, capturing key attributes, goals, and challenges.

  3. Define

  4. Clearly articulate the challenges and opportunities discovered during the empathize phase. Define a specific problem statement related to the Create Listing Process that the team aims to address. Use insights from the Primary User Persona Cards to inform and tailor the problem statement.

  5. Ideate

  6. Brainstorm and generate a wide range of creative ideas to improve the Create Listing Process. Encourage a free flow of ideas without judgment, fostering a collaborative environment for innovation. Refer to the Primary User Persona Cards to ensure ideas resonate with the identified user needs.

  7. Prototype

  8. Develop a tangible representation of your ideas for the Create Listing Process. This could be a wireframe, a paper prototype, or a digital mockup. The goal is to create something that allows users to interact with the proposed solutions. Ensure the prototype aligns with the preferences and behaviors outlined in the Primary User Persona Cards.

  9. Test, Refine, Test

  10. Gather feedback on the prototype by testing it with actual users. This step involves observing how users interact with the prototype and collecting insights on its effectiveness. Iterate based on user feedback to refine and enhance the Create Listing Process. Validate changes against the expectations set by the Primary User Persona Cards.

  11. Implement

  12. Take the refined solution from the testing phase and implement it into the actual Create Listing Process. This may involve collaboration with development teams, adjustments to user interfaces, and integration of new features.

  13. Learn

  14. Reflect on the entire Design Thinking Sprint. Evaluate what worked well, what could be improved, and what insights were gained throughout the process. Document key learnings that can inform future iterations or other projects. Use the Primary User Persona Cards as a reference point for understanding user preferences and needs during the learning phase.

Asking a question is typically because you don’t understand or require clarification on the topic. The idea of a 'stupid' question is that an answer may seem obvious to some, but clearly, not to the person asking. The fear I had originally was just being embarrassed or laughed at by my peers and, more importantly, my team. Enter Design Thinking, a methodology that not only mitigates this fear but transforms questions into powerful tools for innovation.

It wasn’t until I read a book authored by Adam Grant, that he was prompting the idea to act as a scientist, proposing a question (hypothesis), investigating its potential, and iterating until validated or disproven. Design Thinking echoes this scientific approach, providing a structured path from the opening statement to evidence-gathering and decision-making. It's not just confined to product development; we apply it across our business, from planning service offerings to crafting effective paid ads. Design Thinking offers a more efficient way forward.

The great thing about this method is that it isn’t confined to only product development. We use it for most of our business and marketing decisions, from planning the service offerings at Marketplace Studio to the type of paid ads we create. Why spend the money on ads only to find out after the money is gone that they don’t work, and then change them and restart the burning cycle? 

There must be a better way! Thankfully, there is. Design Thinking.

From 0 to 0.1 - Uncovering The Unknown

At Marketplace Studio, we work with a range of industries, entrepreneurs, and founders who are domain experts and believe a marketplace can relieve some of the pain in the industry. Two examples come to mind, personally, GridBid which is a marketplace based in Texas where Homeowners can source quotes for home generator sales and installation from reputable companies. The Project Garage is a marketplace for DIYers to get personalized advice from Trade Professionals about a project they are stuck on.

GridBid and The Project Garage stick out because, in terms of knowledge or domain expertise, I am without a doubt, a 0 in both regards. With that being said, our team was still being trusted to design and build their marketplace on Sharetribe. 

The question was, how do I become knowledgeable enough in these industries to build a great MVP? I knew absolutely nothing about home generators, and I am a computer person, not a handy person. This has happened with the majority of our clients, whether it's the industry or their unique approach, it requires a new level of understanding and information to design and build the solution they’ve dreamt about. 

For GridBid, we started with building the Brand first which allowed us to to uncover a silhouette of the users we were going to design the following feature for, the Quote Submission Form for a homeowner. 

  • Why is GridBid especially important to Texans and not elsewhere in the country?

  • What types of generators work to power homes during power outages?

  • What’s involved in the installation of one?

  • What’s the current solution to the problem?

For The Project Garage, it was more related to the Category Taxonomy and the hierarchy of the subcategory attributes which would later allow for an excellent search and discovery UX. 

  • What is the difference between a red seal and a journeyperson?

  • Do people need a license to do that type of work?

  • What question would a DIYer ask to get help from this type of Pro?

Some may not think the questions listed above are examples, but I sure did when I was in a meeting with experts who hired Marketplace Studio to design and build their marketplace. 

Context & Expertise: The ‘Stupid’ Question Equalizer

Stepping into the complexities of unfamiliar industries, I often found myself confronted with questions that might be perceived as 'stupid' by experts. Yet, it's precisely in these moments that the significance of context and expertise comes to the forefront—a leveling force for all questions. 

All of our clients at Marketplace Studio are experts in their domain and vary in a range of technical savviness. It is the perfect mixture of knowledge and passion that results in a beautiful dynamic and turns it into chunks of code. 

This post explores personal experiences, ways to overcome the fear of embarrassment or rejection, and the importance of getting outside of your comfort zone. If you are not comfortable or not in an inviting environment, write down your questions and use a search engine or AI tool to investigate the answer. Knowledge is just a keyboard click or tap away.


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