On Enthusiasm

Kevin Kelly writes that enthusiasm is worth 25 IQ points. I wholeheartedly agree.

Watch this video by Casey Neistat and tell me you can't feel the enthusiasm he has for his city, his work, and his craft. It's palpable. It's also what makes him who he is: all of his videos have this infectious energy.

I've been thinking a lot about interviewing, and have come to a simple conclusion: I would rather work with someone who is enthusiastic than with someone who is smart. So much so that I am willing to tolerate meaningfully worse intelligence if they bring overwhelming energy and enthusiasm.

Taking this to the margin, does it matter what your degree is? Where you went to school? Your resume? Where you did your last internship? Honestly, no. If you can show up and prove that you are bringing energy, enthusiasm, positivity, and a hunger to do better, I'm sold.

It's really not that complicated.

Of course, this is really a reflection on me: this is a way to tell myself to be more enthusiastic.

At the end of the day, I really like my job. I mean, I really like my job. So much so that I commit a ridiculous amount of time and effort towards it, and care deeply about the products we are building being successful.

But now and again, I get down, I get depressed, I feel frustrated, and (to my great shame) I sometimes give up.

That's not me at my best, but it is the truth.

Then I think about Casey. I think about Kevin Kelly. I think about myself 10 years ago, and how pumped I would be to know I've ended up where I am right now, and how badly I would want to keep that going.

So I pick myself up, dust myself off, apologize to myself and others for being a (temporary) quitter, and I get after it with a white-hot intensity and a positive attitude.

Enthusiasm. Enthusiasm, enthusiasm, enthusiasm. Bring that energy, bring that hunger.

Nothing else comes close.

Interview Questions

Fun Questions

  • What makes you really angry?
  • If I spoke to your best friend, what is one word they would use to describe you?
  • If you had to ride an animal into the Battle of Helm's Deep, what animal would you ride and why?
  • If you were an action figure, what two items would you come with?
  • How much sawdust can you put into a rice krispy square before people start to notice? How would you figure this out?
  • What are the top 5 websites you visit every day? What is your favourite way to gather information? What subreddits or blogs or instagram accounts or TikTok stars do you follow?
  • Who is your professional role model, and what do you like about them?
  • If you could choose one fictional character to be your mentor, who would it be and why?
  • Why did you choose this university? Why did you choose this program?
  • What is your secret to productivity?
  • What advice would you give to yourself graduating high school?
  • What was your first job, and what was the most important lesson you learned from it?
  • You are unexpectedly gifted a day off in the middle of the week. What do you do with it?
  • Your house is on fire (animals and people are safe) but you can grab 3 items. What do you grab?
  • What is the best gift you've ever received?
  • What is your favourite quote?
  • What are the last 5 books you read?
  • What are the open tabs on your computer right now?
  • Describe your day up to this point.
  • What's something weird or unusual you did early on in life?
  • What important truth do very few people agree wtih you on?
  • If you were a product, what would your value proposition be?
  • How did you prepare for this interview?
  • What's a conspiracy theory you believe? What makes it interesting?


Product Questions

  • You've just been hired as the first PM at [well-known product, like Instagram]. There are no metrics of any kind yet. What sort of data would help you determine the health of this feature?
  • Tell me about a time you advocated for somethign that others did not believe in. How did you develop convinction even when others didn't have it? How did you get enough organizational buy-in to allow you to move forward with the initiative?
  • Why did you choose to work at the last company? Why did you choose to leave?
  • Tell me about a time when you were certain about a product or feature and you turned out to be wrong.
  • Tell me about a project you worked on in the last two years that you are most proud of. Provide the context, actions you took, results, and learnings.
  • How would you explain product management to a stranger?
  • A customer tells you they want a new feature. How do you decide whether it is worth building or not?
  • What was your most successful product as a Product Manager?
  • What makes a successful launch?
  • What are the qualities that differentiate a good product manager from a great product manager?
  • Do you have any technical skills that set you apart from other applicants?
  • Is consensus always your goal? When should you strive for consensus and when should you not?
  • How do you make decisions with data? How do you make decisions without data? In what contexts?
  • Tell me about a product you used today. What did you like about using it? What would you change?
  • Think of a product you hate to use. How would you improve it?
  • What are the trends you're paying attention to? What excites you about them?
  • Give me a prediction about this trend 10 years from now. What do you think will happen? Why?
  • Tell me about a time you failed professionally. What happened, where did you go wrong, and what did you learn?
  • Is Facebook succeeding? Why or why not?
  • Our indoor camera is not selling very well. What is one change you would make to improve sales?
  • Will OpenAI surpass Google in terms of daily searches? If so, when? 
  • Pick a product you love and use often - what is their secret sauce? Why do you think they are so much more successful than competitive products?
  • How do you gather and prioritize customer feedback?
  • Can you describe a time when you had to pivot or change direction of a project?
  • How do you stay updated on industry trends and emerging technologies relevant to product management?
  • How do you practice your craft in a similar way to how a musician practices scales? What do you do regularly to get better?


Soft Skill Questions

  • How do you communicate with executive leadership?
  • Who do you respect most for their leadership ability and why?
  • What do you look for in a manager?
  • Should engineers speak with customers? Why or why not? In what circumstances?
  • Why do you want this job? 
  • Why should we hire you?
  • What does success at the end of this co-op term look like for you?
  • Tell me about a time you disagreed with a colleague. How did you resolve the conflict?
  • Who is the best manager you've ever had? What made them successful?
  • What's the most important factor for you in looking for a co-op?
  • What's the question you wish I asked?
  • What is your strategy to accomplish great things? Do you work every day? Extra hard during the week? What does your weekly cycle look like?
  • How important is charisma for a product manager?
  • If you were hired and then we get to the end of your co-op and it does not go well, why would that be?
  • What are 3 words your best friend would use to describe you?
  • How ambitious are you?
  • Can you give me an instance where you perceived a team problem at work and stepped in to fix it? What exactly was your remedy?
  • Would your previous boss say you were so good they would work for you?
  • What is the most important trait of high performer?
  • Out of what I see on your LinkedIn and your resume, what are the things you are trying to emphasize? What are the things you are trying to hide?

Running Up That Hill

I run on average 3 times per week, and my typical run is either from my house to Point Pleasant Park and back - about 15 km - or to the Dingle and back - about 5 km. Which route I take is highly dependent on how much time I have in the day, how I'm feeling, and how much pain and suffering I hope to inflict on myself that day (just kidding, but not really).

On my run this morning, I felt groggy, my knees hurt, my calves were screaming, and I was struggling to keep up even a gentle pace. It was a beautiful sunny morning, the light through the trees was ethereal, and I was rocking out to some great tunes. So no excuses at all for being lazy.

Then I hit the big hill.

There's a hill from the Dingle, at the bottom near the ocean, up to the gate entrance to the park. I've had an internal duel with this hill since I moved to Nova Scotia, and it has become my nemesis. Chuck Klosterman has this amazing description of arch enemies vs. nemeses.

A nemesis is someone you battle but secretly like, someone you'd miss if they were gone, someone who ultimately makes you better: Batman and Joker, Roy Kent and Jamie Tart, Captain America and Ironman, Adolf and Rudolf Dassler who founded Adidas and Puma respectively. 

An archenemy is someone you hate deeply to your core, who you would piss on their grave, whose very existence riles you up: The Avengers and Thanos, The Jedi and Emperor Palpatine, Greta Thunberg and any oil company executive. 

This hill is my nemesis. It makes me better, but does it ever frustrate me.

On a good day, I can make it to the top over the course of about 1 song on my playlist, say 3:30. On a bad day it might take me two. But recently I've noticed I'm improving because I can make it up the hill without stopping, whether it is fast or slow.

I've also noticed a change in my posture and general feeling towards this hill. I take a loop that goes through the magical forest, down a beautiful tree-lined trail, along the seawall, to the beach at the bottom, and then this hill is the tax I have to pay at the end to get home. It's not pretty, it's not that fun, the pavement is cracked and the street is not wide enough for all the cars that go by. I've had this feeling of begrudging acceptance towards this part of the route since I moved here.

Until today.

Something changed where I hit the bottom of the hill and suddenly felt so alive, so ready to perform at my best, that is was almost intoxicating. I cranked Lose Yourself by Eminem, and absolutely demolished this hill, setting a new record for myself in the process. I reached the top and instead of gasping for air, felt like I could turn around and do it again. Something about the persistent challenge of striving to do better, and knowing this is the hardest part of the journey, forced me to bring out my best and push myself.

There's something beautiful about this metaphor: the struggle is what makes us our best. Going further, it's not the flat, easygoing part of the journey that we remember or ultimately demands the most of us, it's the big inclines, where things get really hard, that we shine the brightest.

The lesson here is to embrace, and attack, the big hills in our life.

I've been feeling frustrated with one particular recurring meeting I have with our exec team, which often feels like a chance for them to beat us up for an hour. It clicked for me today that it's just the work version of the Dingle hill. These meetings are often where I am at my best, where the best of my work comes through, and even though I don't always shine the brightest or leave feeling my best, it is the struggle that makes me better.

So I need to keep reminding myself: don't shy away from the big hills. Embrace them. Attack them. Show them what you're made of, even on your worst days.

Because one of these days you're going to totally crush it, and you'll make it to the top a champion.

Process, Relationships, Brains


I have a mental model on how to solve sticky problems that boils down to this hierarchy: start with the process, then lean on relationships, and then trust individuals to use their brains. Processes help to build frameworks and mental models for repeated problems to be solved in standardized ways. The value of building a process is often to improve repeatability and/or speed, while removing the “human element” from the problem. Things like Agile, Weekly Meetings, Product Requirements Documents, and Meeting Agendas are processes that outline ways of solving repeated problems regardless of who is involved. In areas where these fail, we need to lean on relationships. See my note below, but in many cases, we can overcome gaps in process by having strong relationships with our counterparts. Lastly, if both process and relationships fail, we trust each other to make thoughtful decisions on our own in our areas of expertise, giving each other the benefit of the doubt.

3 Types of Editing

In this interview with Tim Ferriss and Seth Godin, Seth describes how there are three types of editing: copy editing, line editing, and developmental editing.

Copy editing is reviewing a document for grammar and accuracy. This is where spellcheck in Microsoft Word shines.

Line editing is reviewing sentence-by-sentence for precision to the larger context of the document. I think of this as "is this sentence written in the best possible way?" and ways to smooth out your voice for the reader.

Developmental editing is reviewing the holistic context of the document and whether it is making a compelling argument. This is answering the question "what is the change you seek to make?" and how well are you doing that? This is about moving paragraphs or chapters around and adding or removing context to make the story resonate more with the audience.

I've found distinguishing between these three types of feedback incredibly helpful, and further, that different people are better at providing different kinds of feedback.

First, spellcheck and Grammarly are excellent tools for copy editing, and with these tools so readily accessible, it's impossible to forgive poor copy editing. However, it's worth stating that no one reads a document and changes their behaviour because the copy editing was excellent. This is table stakes. In fact, Seth describes how he hires an editor to copyedit his work prior to sending it to his publisher for further edits. I think that's a great tip to reflect on: have a tool or someone you trust copyedit your work before sending it out for more serious revision.

Second, have someone you know is an excellent line editor review your work. I work with a particular executive who is relentless for line editing, which can be good and bad, but ultimately makes every sentence in the document as strong as it can be. Great line editing reviews every statement and asks "how could this line be stronger?" and line the beams in a bridge, improves the strength of the document as a whole. Two ways to do this: have a details-oriented colleague go through your document line by line and make edits. Alternately, the tip I prefer: give yourself 24 hours between writing and editing, because these are different functions in your brain and you need the space, and then review every single line in reverse, asking the question "could this be better?"

Third and most importantly, have a mentor, peer, or trusted friend read your document and reflect back on whether it resonates. This is by far the most difficult kind of editing but is priceless in the pursuit of excellence. Having someone who can see your work for what it is striving to be, internalize that goal, and then reflect back ways to reorient your structure to be more impactful can be the difference between good and great. I've read so many books that desperately needed developmental editing: the concept is excellent, the stories are mediocre, and it drags on too long. A developmental editor will help you transform not just the sentences on the page, but the whole way you're constructing your argument. 

Lastly, a few warnings. 

Asking for the wrong type of feedback from the wrong type of person can be painful. Despite our best efforts, some people genuinely think highlighting the spelling mistakes and nitpicking your data will help improve your writing. It might, but in my experience, that is not the most impactful area to focus on. It seems that some people never quite overcome this hang-up, as if it is deeply rooted in their personality, so don't fall down the rabbit hole of trying to get all the details right without first understanding the context.

Humans are storytellers. As compelling as a series of strong data points connected linearly in an argument is, you want your work to resonate on an emotional level because that is where change comes from. Very seldom does cold, hard data make the change we're looking for. We all believe the stories we tell ourselves, and without that connective tissue, your argument can't hold weight. 

In the words of Simon Sinek: Start with Why. In Seth Godin's words, what is the change you seek to make? In my words, what is the problem you're trying to solve? Begin there. Get the big picture right first, and then sweat the details. Don't lose the forest through the trees.

AI as UNBPI

I listened to this interview between Tim Ferriss and Kevin Kelly and he described ChatGPT in a way I really resonated with: as the Universal Personal Intern. His analysis is that ChatGPT is effectively culminating the wisdom of the crowd into a series of tools that is capable of providing the same level of work you could expect from an intern: highly adept at producing a high volume of mediocre ideas that then need to be tuned and adjusted before they are ready for primetime. He then described it as "not bad", or the universal not bad personal intern (UNBPI). 

I really like this assessment and it aligns with my own (limited) experience with using ChatGPT. 

I've been astounded as the proficiency and usefulness of ChatGPT as a whole, and it really is a step-change in the level of functionality that is publicly available (for free!) to anyone who wants to use it, but I must agree with KK on this: the quality of output is just not that high.

There are countless stories of it "hallucinating" and confidently presenting false information, or writing complete essays that are built on false pretenses and misunderstood sources. This is dangerous for those who don't understand what they are doing, and expect the system to be more reliable than it is. It's like giving a power tool to a pre-teen: it's incredibly powerful, but only useful if used correctly.

However, the way I like to think about ChatGPT is as a first-year intern, or something that is fully capable of producing elementary analysis of complex topics and providing that information back to me to make a decision. I consider it an assistant who is able to quickly search the internet for what currently exists, and provide options for review. I would never allow this system to publish without review, hence my comments above, but it is incredibly effective as a generative tool.

So here are a few things I've used my UNBPI for in the last month:

  • Creating recipes that align with my target diet
  • Creating a workout plan based on my goal of running a marathon this year, taking into account my schedule
  • Creating templates for standardized documents, like product requirements documents and executive proposals
  • Researching competitive products and their positioning within the market
  • Producing a list of blog post ideas related to various topics, and headlines on those topics
  • Writing a SQL query to accomplish a specific task I couldn't figure out on my own (side note: ChatGPT as a paired coding tool is unbelievably powerful, this is worthy of its own blog post)
  • Producing ice breaker questions for our team summit and fun interview questions for candidates
  • Reviewing, editing, and summarizing blocks of text to condense them and make it easier to read

Going forward, I believe AIs (plural, because they are different kinds of machines) will influence our world in new and unexpected ways, but I tend to agree with KK that they are going to be incredibly adept at a limited range of things, requiring a more holistic review by humans.

Great as an intern, poor as an IC. 

On Co-op Students

I've had the privilege of hiring several co-op students in my career. I'm trying to be less biased on the co-op process in general, so here is what I look for when I hire a co-op, what I measure them against, and my best advice for co-op students in general. 

Hiring Co-op Students

I'm trying to be more specific and less biased here, so here's my shortlist of character traits I look for and ultimately evaluate against:

  • Being a fully-formed human being: emotionally mature, independent, willing to grow 
  • Quality and depth of thinking, bonus point for showing their process
  • Disagreeableness, willingness to present unconventional perspectives and back them up
  • Problem-solving, specifically around ambiguous or no-right-answer questions
  • Communication skills: oral, written, graphic
  • Resilience, can take tough feedback and improve accordingly
  • Grit and resourcefulness
  • Curiosity, humility, and willingness to learn
  • Product intuition, or an intuitive sense for what works and what doesn't in the chosen field
  • ENTHUSIASM - in the words of Kevin Kelly, worth 25 IQ points - would much rather have someone mediocre on paper who really wants to work here than a genius who doesn't

Green flags:

  • Entrepreneurial or startup experience
  • Experience working in a minimum-wage job
  • Strong opinion on something unconventional or unpopular
  • Having worked or lived abroad, speaking another language
  • Proof of having taken the initiative towards personal growth (ie courses, YouTube tutorials, books, etc.)
  • Learning in public: a portfolio, blog, social media account, or other public proof of learning or experience
  • Past experience in the role, or something similar
  • Asks great questions at the end of the interview

Things I don't care about:

  • Brand names on your resume - I'd even go so far to say working at a brand name company (Apple, Google, Facebook) can be a net-negative in my experience, but I don't hold it against folks highly, especially this early in their career
  • Grades / signs of intelligence - if you've made it this far, you're smart, moving on
  • Discipline or Field of Study - PM is pretty discipline-agnostic and we'll teach them the Product side if we need to
  • Extra-curriculars - unless it applies to the points above, not important for me
  • Level of experience - I put some weight into what experience can build in terms of maturity and proof of capability, but a young superstar will outperform an older dud every day of the week

Red flags:

  • Lack of humility or a know-it-all attitude
  • Does not ask any questions at the end of the interview
  • Clearly focused on the wrong things, like salary, prestige, or influence 
  • Unclear on why they want the role or their career direction
  • Poor quality of thinking
  • Poor communicator
  • Speaking poorly of a past manager, company, or colleague
  • Lack of maturity
  • Lying 
  • Overexaggerating their impact 
  • Boring

Process:

  1. Submit a resume for review. I will often ask for examples of work to accompany, including a portfolio, website, social media account, or any other public proof that you are capable of doing what you said you could do.
  2. Interview. I will often ask a series of questions to evaluate: communication skills, enthusiasm for the role, fit within our team, and (for lack of a better term) general vibe. This is often a test of whether I feel I would enjoy working with you for extended periods of time.
  3. Project. Sometimes this happens before the interview, but I ask candidates to do a task for me to demonstrate their skills. This is not meant to be timed, or put them under tremendous pressure, but rather to evaluate them at their best. Best-case-scenario this is included in the job posting. I am ultimately evaluating their depth of thinking, technical ability, communication skills (written, graphic, etc.) and enthusiasm for the role (ie do they do the project or not?). This is the best way I've found to evaluate performance, and comes highly recommended from a mentor and friend (HT: Gilad).
  4. If required, additional interview.


Evaluating During The Co-op Term

I do my best to present clear guidelines on how I evaluate all of my co-ops at the beginning of their term, so there is no ambiguity around what I expect. It is a failure on my part as a manager if we get to the end of the term and disagree on the evaluation. Having a template to work from gives clear guidance on what success looks like, how performance is evaluated, and ultimately how to achieve the target we are both aiming towards. To be clear, I want all of my co-ops to achieve an Outstanding (or at least Excellent), and setting clear targets on how to do that is helpful for both of us.

At ecobee, we have 6 company values that I use to measure against. The bullet points listed are my measure of the Outstanding level, but often I will look for the individual to find ways to not just meet the criteria below, but shine beyond what is written.

Cultivate Curiosity

  • Student actively seeks opportunities to develop skills in specific areas of interest. For example, taking initiative on potential projects/tasks to work on or maximizing 1on1s with a diverse range of people 
  • Courageous and humble in requesting and gathering feedback
  • Receives feedback well and responds taking action

Aim for Impact

  • Achieves meaningful outcomes for the business within their co-op term
  • Proactively identifies areas of impact
  • Prioritizes effectively and communicates this proactively to their manger

Think like an Owner

  • Student is independent and has exceptional self-management skills 
  • Able to solve difficult problems on their own
  • Presents thoughtfully curated options and a recommendation when a decision requires additional feedback
  • Adapts effortlessly to changing priorities

Give Respect and Build Trust

  • Completes deliverables on time at an exceptional quality, and builds a reputation for being dependable
  • Preemptively unblocks work items by asking for support and/or clarification, well ahead of deadlines
  • Builds strong relationships with colleagues
  • Student is an essential core member of the team and provides unique value through their role. Employer would be delighted to have the Co-op return for full-time. 

Work for the Planet

  • Preemptively aligns work with core sustainability initiatives
  • Proactively identifies areas for improvement in sustainability-focused initiatives

Start with the Customer

  • Deeply internalizes product goals and initiatives
  • Proactively identifies areas for improvement in customer journey and create a plan to resolve
  • Begins with “what would be great?” and finds ways to achieve this goal without compromising on user value


Advice for Co-ops

  • Have a long-term plan. Don't pick your next co-op based on what is shiny and new and pays the best, pick your next co-op based on how well it aligns with your long-term goals and intended career trajectory.
  • Go through the side door. Some companies rely on the typical co-op system to vet candidates and find the best option, but in my experience, the best candidates are the ones who want to work with you so badly they are willing to bypass the whole system to make this happen. Huge bonus points for finding a way to circumvent the system and stack the deck in your favour.
  • Big risks equal big rewards. I did a co-op term in Germany, and that was a step-change for me personally and professionally, and helped me to eventually work on a cool project with a friend, which led to starting a business, which led to Venture for Canada, which led to getting my first job at Mosaic, which led to my second job at Nymi, which led to where I am now. Taking the risk of doing a co-op overseas, getting paid effectively nothing, in a country I did not speak the language was a crazy thing to do in hindsight, but it set the stage for future success. Now is the time for you to take bigger risks.
  • Learn in Public. This blog is my way of learning in public. I obviously don't have all the answers, but it is a chance for me to show my work and my process, and get something out into the world. Having a public portfolio, or something that demonstrates your ability, will take you much, much further than a line on a resume. If you can demonstrate your passion by putting your work out into public, risking criticism and ridicule, you will hit another gear of growth. I wish I did this earlier.
  • Show your passion. I want to work with people who want to work with me, plain and simple. I wrote above that enthusiasm is worth 25 IQ points, and I firmly believe that is true. By the time you get on the shortlist of people being considered, everyone is excellent, and the deciding factor is often determined by who wants it more. Show how passionate you are, over and over again, and good things will come to you.
  • Gain life experience. My first criteria above is about being a fully-formed human being, and it's a bit tongue-in-cheek, because there's no way you're going to be fully-formed at this phase in your life. It would be somewhat disappointing if you were! However, the best way to grow quickly into a professional, or someone who is fully-formed in the workplace, is by (ironically) gaining life experience. There's lots of ways to do this, but here are some of my favourites: travel, take a class in something that scares you, do a project that feels way too difficult and publish about it, start a blog, meet new and interesting people, make great art. 
  • Get good at communicating. Presenting information, either written, verbal, and in a presentation to a group, are vital life-long career-spanning skills. The sooner you can become excellent at all forms of sharing ideas, the more successful you will be. There are many amazing resources about this, including books, YouTube videos, and courses, but by far the best way to be a better communicator is to practice. Having a blog is (effectively) free and allows you get more reps in, but I would highly recommend building a feedback cycle. This could be hiring an editor, finding a mentor who will review your work, and/or having a friend or loved one provide feedback. Bonus points if you learn to use AI for this.
  • Take great notes. The best lifehack I've found for career growth from co-op to fulltime is to be the person in every meeting who takes notes, captures ideas and action items, and shares them afterwards with the team. Make this a habit and build a reputation of doing this, and you will be invited to more important meetings. More important meetings = better projects = more responsibility = faster path to success.
  • Ask more questions. One of my biggest criticisms of co-ops in general is they don't ask enough questions. No one expects you to know what you're doing. I would rather spend 5 minutes answering your questions (bonus points if I can do that async) than having you spend 5 hours heading in the wrong direction. Being explicit, specific, and thoughtful about what questions you ask and why will help fast-track you from flailing, unknowledgeable intern to confident, competent employee. Further, developing a set of default questions to ask of all projects (timeline? success criteria? priority?) will help you greatly. This is especially true in an interview. Don't ever leave an interview without asking at least 5 really good questions. Prepare these ahead of time.
  • Leverage the hot new tools. When I graduated, social media was in its heyday, and many of my older colleagues were not yet on Facebook or understood the marketing power of tools like LinkedIn, YouTube, and Snapchat (is that still a thing?). Being a huge nerd, and a millennial, I was effectively an expert at all of these at an early age, but wasted my opportunity to make a meaningful gap for myself. The hot new thing right now is AI, and I can tell you with confidence it will change everything, so the sooner you get comfortable with it as a tool, the more useful you will be. Understanding its advantage and disadvantages, and when to leverage its capabilities, will put you a step ahead of colleagues who are older and more experienced in other ways, leveling the playing field. Double-down on your strengths.
  • Above all else, find ways to be useful. Remember that this opportunity is not about you. You are gaining valuable experience and skills along the path of fulfilling your actual purpose: being useful to the company that hired you. No matter how much HR nonsense is spewed your way about how companies care about investing in their employees, don't forget that you are not the main character in this story. In the words of Zig Ziglar, you can have everything in life you want, if you will just help other people get what they want. Help your team first, and yourself second, and it'll all work out in the end.

Operating Principles

This is a shortlist of my personal operating principles.

#1 Make a Proposal

I’m a firm believer in starting with a proposal rather than a blank page. As product managers, our responsibility is to guide the team towards experiences we believe to meet our customer’s needs, and this often starts with us making a proposal and revising as new information arises. We often juggle requirements and perspectives from different teams, all of which is important to factor into our decisions, but I have seen time and time again in my career that starting with a proposal (even if it is a SWAG) is the best way to align disparate groups together. It is my expectation that by default, any problem or decision is accompanied with a proposal, even if it is a draft. This is a great article expressing a similar mindset (Level 4). One of the side-effects of this principle is you must be willing to put yourself out there and get bruised along the way, which takes courage and discipline. I personally have never had a proposal document come back from management without dozens and dozens of comments, which is very much to be expected, but requires a thick skin. The trade-off of making a proposal is getting your ego bruised along the way, but the best leaders take this is in stride, putting the quality of the product higher than the optics of being right.

#2 Lead with Relationships

I’m a firm believer that great teams build great products, and I personally choose to lead with relationships in the way I interface with teams. My expectation is that we treat each other with respect and candor and hold each other to account, but also get to know each other as people. We’re not robots, and despite our best efforts everyone we work with is a human underneath (at least for now), which means we need to be mindful of personalities, emotions, ways of working, and context. This is sometimes referred as Nemawashi, which in my mind translates to “having the conversations before the meeting”. This is the art of being a strong product manager, and something I expect of the people I work with and manage. I’ve seen consistently in my career that leading with relationships will buffer other issues.

#3 Clear Thinking Starts with Clear Writing

I like to think I’m a decently intelligent human being, but I am very confident I am not nearly as smart off the top of my head as I can be when I write things down. The ability to edit our thoughts over time is one of the markers of the advancement of the human race, and something we should leverage extensively. By default, and in almost every case, the correct action is to write your thoughts down. I read much faster than I can listen, and editing is much easier than writing, so when in doubt put your thoughts into a document. Seth Godin also notes that written documents allow us to transcend and overcome the barrier of time, which is a cheap, effective, underrated superpower we should leverage more often. 

#4 Ownership and Responsibility

Product Managers often wear 3 hats: Product as owners of requirements and stewards of customer value; Product as leaders within the program; and Product as caretakers, who clean up at the end of the night and turn off the lights once everyone has left. My rule of thumb to act like an owner: if this needed to happen tomorrow, what could you do to make that happen?  Tactically, this means we should strive to do the following: set clear expectations on roles and responsibilities within the organization, and work with stakeholders to ensure this is upheld; delegate responsibility and hold others accountable to it; if something falls through, lead with a posture of picking it up for the time being with expectations to delegate in the future.

#5 Sense of Urgency

I stole this from Thomas Keller: everything that is worth doing, is worth doing with a sense of urgency. Deadlines are one of life's greatest tools, and highly underrated in my opinion. Acting like everything we are work on is due imminently is the best trick I've learned to ship work that matters. I demand of myself and those around me that we move quickly and with purpose on everything we do, whether it is due in minutes, hours, weeks, or years. The moment I stop acting in this way, the quality and quantity of my work falters, without exception. When in doubt, act like you're already late, work hard, and then ship.

#6 Decision = Argument + Evidence

I learned this during my time at Mosaic: every decision can be boiled down to an argument, which is a proposal on the way the world works or should work and how we plan to get there, and supporting evidence. Decisions without evidence are prone to failure, and show a lack of discipline in the decision-making process. When we push for decisions without backing them with evidence, we are believing that luck or fate or circumstance will bail us out. Decisions without strong arguments are often easy, low-hanging fruit, that is not worth the time we allocate to them. If a decision is so easy to make that you can do so without a strong argument, you should make it and move on. This shows a lack of courage within the organization to surface the contentious points and debate the stuff that matters. This simple formula has also been useful to indicate, with no feeling of personal attack, that a decision requires more work before it can be made. Saying "a decision = argument + evidence, and some of those pieces are missing here" is a criticism of the work, not of the person, and encouragement to regroup and try again. 

Know What You Want

Apr 4 2021


“Life punishes the vague wish and rewards the specific ask.”
— Tim Ferriss

Knowing what you want is a superpower.

Most people don't know what they want. Ask what they want out of life and they will respond with something vague and unhelpful like "I want to be happy" or "I want to be successful".

Defining precisely, unambiguously, what you want, is the first step in getting it.

The second step in getting what you want is making a plan, but in my experience most people struggle with the first part.

Making specific asks is a skill that can be learned, and it takes will and effort. Putting in the time to understand specifically what you are asking for is the hardest part.

In my experience, most people don't put in the emotional labour to understand specifically what they want. Until recently, myself included. Here's a simple test: why are you working where you are working? If you can't answer that, you probably haven't put in the work.

In high school I got a job at a banquet hall so I could pay for a trip to Italy. I wanted to go to Italy because I had never been on an overseas trip without my parents, and wanted to see the world on my own terms (sort of). I got a job washing dishes to pay for it.

I ended up loving that job and stayed there for almost 4 years. My specific ask changed from "pay for trip to Italy" to "work in a job I enjoy doing, to save up money for university". The day it was no longer fun and I had saved up enough for first year, I quit.

Knowing what you want puts guard rails around your decisions. It's the first part of long-term decision-making, and helps give clarity on why you are taking the steps you are taking.

This happens in the business world all the time: entire roles are dedicated to understanding what users want and need. This people are often called Product Managers.

Generally, roles can be broken into 3 categories: requirements, process, and management.

Requirements roles are any job where you are responsible for parsing ambiguous asks into specific outcomes. Product Managers do this, but often so do Engineers, Designers, Marketers and Salespeople. Emotional labour in the modern era is usually focused on this step.

Process roles are execution focused: now that we know what we want, how do we give it to people? This may also be Engineers, Designers, etc. and often folks who are earlier in their career. This transition from 'how' to 'what' is a big part of growing into a senior role.

Lastly management roles focus on organizing and supporting the people doing the other two.

The lines are rarely this clear and most roles have more than one category, but it's a good way to think about it. Doing the hard work of translating what people want into actionable requirements is not easy, but it is fundamental to success.

YCombinator's motto is 'Make Something People Want'. If it's good enough for the most successful accelerator program of all time, it's good enough for you.

Here are some strategies I have found helpful:

  1. Ask Follow-up Questions.

    What do you want out of your career? I want to be rich. What does rich mean to you? To be financially stable. What does being financially stable mean? Making $4k per month and having no debt. Keep asking until you have specifics.

  2. Spend Time Alone.

    The world is noisy and your deepest desires are whispers. Spending time alone, in what Ryan Holiday refers to as Stillness, is fundamental to uncovering these needs. Run, meditate, walk in the forest; whatever helps clear your head. Do it more often.

  3. Get Another Perspective.

    Ask your closest friends these hard questions about you. They can act as a mirror; it might be distorted or blurry, but it's reflecting some part of you back. It's often surprising what it reveals. Example: what are the activities that bring me joy?

  4. Keep A Log.

    Journaling is a powerful tool to understand yourself, but a simple log of things you like and things you don't can be just as revealing. What activities bring you energy? How do you feel after eating carbs? Does this person make you happy often? Find the patterns.

  5. Set SMART Goals.

    Specific, measurable, actionable, realistic, timely. This is a great filter to put your answers through. I want to be rich fails. I want to be debt free and own my home by age 40 might pass. Set a clear target. You can't hit what you can't see.

Of course, execution matters, but there are a million external resources to help with that. Knowing what you want is an internal battle only you can win. So start fighting.

What do you want?

Think Longer

Mar 27 2020


“The only reason for time is so that everything doesn't happen at once.” - Albert Einstein


An early mentor at one of my internships gave me the advice to “Think Longer”. It might be the best piece of advice I failed to take seriously.

During university, life happened in 4 month increments. 

Every 4 months alternated between school and internships. Thinking ahead meant considering the next term before it happened. During a school term, you would interview for your internships, and during the internship you would pick your classes for the next term.

This made life rather simple. At the beginning of a term you had clear goals and objectives: work hard, learn as much as you can, and don’t fail the class or get fired. This system became so deeply a part of our lives that we would joke about the mythical “5th month”: the feeling to be in a job past the 4-month deadline.

When I graduated, I joined an early-stage hardware company called Mosaic Manufacturing. I moved to the big city, rented an apartment, and began my career. I had mastered the 4 month project cycle and thought it would apply to my first job. I quickly realized the problems we were solving required years of development. 

My plan was to build a product with Mosaic, and then leave for bigger adventures. I expected it to take 18 months. I remember meetings where we confidently said things like “We should have this in production in 9 months.” How naïve we were.

4 month cycles didn’t apply in this new paradigm. I ended up working at Mosaic Manufacturing for over 3 years before moving to Nymi where I’ve been for the last 2. I never thought I would live in Toronto for a combined 5 years of my life, but that’s how these things go.

Looking back there is a clear trend that I was too naïve to see: the time horizon gets longer.

In grade school, life happened days at a time; in high school, weeks at a time. University happens 4 months at a time, and when you graduate and get your first job, the projects will take years, so that’s how you’re likely to start thinking about your life.

Now that I’m 5 years into my career, I’ve started seriously thinking about what the next 5, 10 and 20 years looks like. Careers tend to happen in decades, and when you think about having a family and doing work that lasts, time horizons can look even longer.

Over the course of a career, your time horizon will grow organically. 4 month chunks will grow into projects, years will grow into decades. Long-term thinking is a superpower, and for most people, it takes a lifetime to come to this realization. You can short circuit that development by starting now.

Long-term thinking forces you to consider lasting consequences. It encourages losing the battle in order to win the war. 

A classic example is investing: don’t spend your money now, put it away so it will grow and be worth more later. 

But perhaps a more subtle example is relationships: asking yourself if you would want to be in a relationship with this person for the next 20 years is a powerful filter. Naval Ravikant has encouraged his followers to “play long-term games with long-term people”. For me, this means finding people who are willing to stick things out when times get tough. 

Even in business, long-term thinking flexes its effectiveness. Warren Buffett’s investment strategy has famously been to buy and hold, and hold, and hold. He buys into companies for the long term. 

For me, the most difficult area to apply this was my career. In finding my first job, it was nearly impossible to think about how it was going to affect the trajectory of my professional life. I was far too concerned with paying my student loans to think about my legacy.

Coming straight out of school, it’s easy to think that the rest of your life will happen in 4 month increments; that planning your life one season or quarter or project at a time will get you where you need to go.

In my experience, that is not true. 

It’s tempting to chase that next promotion, to optimize for the shortest path up the hill, only to discover you have arrived at the top of the wrong mountain. 

Without the clarity to think about where you are going, it’s easy to find yourself led astray.

As your career unfolds, you’ll begin to realize that each step on the journey takes you closer or further away from the person you want to be. One day you’ll wake up, older, experienced, and nowhere near where you expected to be.

Setting aside time to think about the future on a regular cadence is a strategy I have found incredibly useful. Asking the question of where I want to be when I’m 50, 60, or 80, has provided consistent clarity on the path, and helps me look past the daily difficulties. Pausing, and asking the question “Will I be proud of this choice in 20 years?” is often enough to give you a nudge in the right direction. Doing this consistently, day after day, is how to build a life you are proud of.

The future is full of uncertainty, and planning can often feel like a fool’s errand. Many of your best plans will run aground on the rocks of could-have-been. You’ll have to change and adapt and roll with the punches. But all of that said, nearly every bad decision I’ve ever made can be distilled down to thinking too short-term. Consequently, nearly every amazing decision I’ve ever made was a long-term choice. 

Long-term thinking is the only reliable strategy I know to predict the future. 

So my advice is this: think longer. 

Slow down. 

Take a deep breath. 

Don’t sweat the small stuff, and it’s mostly small stuff.

Plan, even if everything is bound to change.

And start thinking about your life in decades, because the decades are going to come faster than you think.


Thanks to Dylan Trebels and Emma Bartel for editing drafts of this essay.