From time to time I work with promising, small startups who are not ready for their first PM but are looking for product expertise to guide them towards product-market fit.

Recently, I was working with a startup that focuses on helping their enterprise clients identify employee engagement issues. Since they felt comfortable in their current core product, they were interested in expanding their product into something they believed would be complementary to their core value proposition: providing advice to corporate leaders on how to take action to fix/mitigate/reduce HR/personnel issues, which would then boost employee satisfaction.

Being a bootstrapped and small startup, expanding their product line would be risky, especially as they have a small developer team and could either work on improving their core product, or work on this new advice system that would enhance their product value, deepening their retention hooks, and further differentiate themselves from their competitors.

The team was also very excited about incorporating machine learning into their advice system, allowing them to scale the service to match their current customer base and their future base.

After internally talking through the risk of working on a new product feature and the opportunity risk of not exploring the new product feature, the team was confused on how they should proceed.

That’s when they called me…

Once I was caught up, I could see the dilemma they were in. There was a lot of value in guiding corporate leaders on next steps, and if they could prove their system did provide such value, they could use their core product to measure the change in employee satisfaction based on their advice!

So how could they potential explore this new advice system and reduce the huge risk of getting it wrong?

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As a Product Manager, I love having One on Ones, or 1:1s as I like to call them, with my direct manager, whether it’s a Director or VP of Product or the CEO. On a bi-weekly cadence, we get thirty minutes, or more if needed, to connect on a number of topics affecting myself and my team in the present, as well a chance to talk about the future including my growth and the company’s future.

Over the last few years, I quickly realized a byproduct of these conversations: fewer surprises during my formal reviews. The One on Ones gave my manager and myself enough time to identify and nip issues in the bud before they blossom to cause havoc. Not only do I look better in those reviews, but my manager is even happier.

The format of One on Ones is geared towards a manager and their direct report, which is probably why most Product Managers don’t have One on Ones with their team members.

And I think that’s a tremendous lost opportunity for Product Managers. Here’s why:
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Marc Andreessen famously stated “software is eating the world“, and very few doubted him on that. But I think there is a new king in town: Artificial Intelligence.

Every day we are hearing of amazing new applications of AI (check out Business Insider’s cool list here) that are slowly changing the world, or sometimes quite rapidly.  More recently, Google has been able to turn those low-quality Street View images from Google Maps and make them beautiful, all using AI with no human interaction.

As always with new, revolutionary technologies, we have the constant fear that our jobs we’ll be replaced by that technology. It’s no different with AI. AI will kill the need for humans in some blue- and white-collar jobs, and hopefully be starting with the dull and dangerous jobs. My sincere hope is that AI will do a number of things for the human race:

  1. Increase our life span by taking over the aforementioned dangerous jobs such as mining, adding more safety automation into our lives such as autonomous vehicles, and help provide more accurate diagnosis of diseases earlier and even assist in determining leading indicators of potential diseases.
  2. Lower the overall cost of living as machines are more efficient, and so the cost of creating goods and services should decrease. AI can also help us be effective agriculture-wise to help increase harvest sizes and decrease waste.
  3. Allow humans to spend more time not working in two ways: take over the mundane aspects of our jobs (the “dull” components) and assist us in our work helping us make better decisions, produce higher-quality work, and thus allowing us to go home sooner.

Out of those three above, I think #3 will directly show those worried about AI’s impact on our jobs that AI is more useful than dangerous, and it’s designed for your benefit. Eric Schmidt recently shared the same sentiment when he mentioned a McKinsey study stating that 90% of jobs are not fully automatable, meaning AI will be there to help, not replace.

(I couldn’t find the mentioned McKinsey study with that particular fact, but this could have been it)

So how can AI help me as a Product Manager go home sooner?

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As Product Managers, we’re always looking to validate our ideas as early as possible before investing more into them, and then actually proving our features are providing value as intended, either by watching our users’ behaviours through metrics, or qualitative feedback.

When solving small problems (or building small features) it might make sense to immediately build the solution if you have enough conviction from your problem and solution discovery process, and it’s small enough that you can kill later if the feature misses the mark entirely.

But for larger problems, which may require a larger feature set to solve, you may need more conviction before building the entire feature/solution set, and that’s a good thing; nobody wants to waste months building a feature nobody uses.

One strategy I’ve often used is to A/B test the smallest version of the feature. That might seem like a “duh, of course” moment, but the question I’ve always contemplated is, what is the smallest version of the feature?

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As designers, whether we are Product Managers, Product Designers, or in HR, there are consequences of what we do, and often we’re okay with that. Uber knew it would be taking away jobs from existing taxi drivers, travel search engines like Hipmunk and Kayak knew they were making travel agent less relevant, and Hotmail, Gmail, FedEx, and UPS knew they were making the postal service less necessary. Isn’t the point of incremental innovation and disrupting incumbents to provide a better product/service at the same or lower price?

But what about the unintended consequences? I wager that many of us do not spend the time deeply thinking of how our actions and products affect the world.

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It’s a start of a new year, 2017 to be exact, and you might have decided that 2017 is the year you jump into Product Management. Excellent choice (I’m biased, of course)!

Getting into Product Management is not easy. I often joke that it’s simpler to become a doctor or a lawyer than to become a Product Manager. Unlike law and medicine, there’s no formal education program (yet) that will guarantee you’ll become a Product Manager. In other words, to get into Product Management, you have to be in Product Management. No company out there will just hand the reins of their product’s future, and most likely company’s future, to just some random person who applied to their PM job posting and somehow got through the HR interview.

Product Management is one of the most difficult positions out there: not only do you need to find out what the market needs and deliver it, but you also have to consistently manage/handle everybody who has an opinion on what you’re doing and what you should be doing…in the most delicate, diplomatic way possible! And that’s not even the crux of being a PM, so what is? Your ass is on the line every single day!

Although it can be stressful, I think it’s the most fulfilling position I’ve had, and it’s something I can see myself doing for the next 5 to 10 years easily!

So how does on get into PM? There are two ways I’ve seen it done:


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Recently, I got a chance to start a business with an old friend of mine. We went for ten months before I realized that particularly business was not the right for me.

In those ten months, I learned quite a lot, and it gave me proof that I have the stomach to handle the intense startup roller coaster. There were definitely some dark days…

Here’s what I learned from my “failed startup experience:”

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When I co-founded IT Werks, I was coming in as the product and marketing guy, and because we had no outside investment, I would only get paid when we closed new clients. My partner has been B2B sales for the past ten years, but we also needed to invest heavily in the development of our product, which he was far better suited than I was.

In other words, I would be the sole breadwinner for the team.

Last time I was in a sales-focused role was between 2004 – 2007, when I was an “Electronic Sales Associate” as Staples and still in high school.

Surprisingly (or maybe not), I was crushing that role and trained new hires who were often older than me in how to sell. I did well because I was honest with my customers, I refused to hustle people and make them pay for things they didn’t need, and I could simplify complex technology into simple terms to help them understand what they needed and that they didn’t. Apparently, I was so good that some of my customers tried to get me involved in their pyramid schemes so they could get richer…even at 16, I couldn’t fall for that crap.

Shift forward nine years later, time to get into sales again. This time, in a B2B role working with small business owners.

But this time, I was failing miserably…

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We’ve all heard stories of how folks have gone on these amazing traveling experiences, maybe swam with dolphins, did some insane yoga moves on the edge of a cliff, or enjoyed a pastry at a Parisian cafe with views of that famous monument. But the craziest, most incredible part of their story: either their flight or their hotel was free, or even both!

And whenever you ask them how they did it, they would usually something like “my points, of course!”

Umm okay…

I’ve always been a cash-back-credit-card kinda guy as I felt I can do more with straight up, cold hard cash then I could do with points. And, I always booked my trip three weeks to two months before my departure date using search engines like Hipmunk, which always showed me lower prices than the credit card travel portals. So, why would I trade in $1 for a mile or a point, which was sometimes worth $0.01?

But as I kept on hearing more stories, and even signing up for Bryce Conway’s American-focused points blog 10x Travel, my curiosity now reached a point of no return: I needed to try this!

So being who I am, I decided to try a 1-year experiment where I would ditch my cash back credit card for a points-based one. This post will detail how I ended up in Bali for free(ish).

 A little warning…

Before we continue, you must promise me you’ll only try what I’ve done if and only if you meet the following conditions:

  1. You’ve got a Very Good credit score right now: 725 or higher. Here are some places you can check out your score for free in Canada: CreditKarma, Borrowell.
  2. You are not in debt.
  3. You will NOT spend more than you currently
  4. You know I’m not a financial expert/guru, and I’m not accountable for your actions

Okay, now that we’re done with the legalish stuff, let’s jump in!

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These series of posts are based on my recent experience with starting a startup, and how I went about it with my partner to get us both on the same page for us to develop a strategy we both believe in and can execute on.


If you’ve been following my posts, at this point you know why you’re doing this, who is your ideal customer and target market, and what problems you want to solve for them.

And you’re probably demanding when are we going to start building a solution, because you already have a solution in mind, or have even started building one. So in this post, we’ll start looking at what we need in our solution.

But first…we need something: your value proposition.

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