I write on things that interest me: product management, startups, and leading a fulfilled life.
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School accountability frameworks measure schools on the aggregate performance of current students on standardized tests rather than the growth students demonstrate between years. As a result, “school quality” measures can fluctuate up or down based on the preparedness of incoming students even if the actual instructional quality remains constant. Read more ›
As humans, we have 24 hours a day to spend as we choose: socializing, sleeping, eating, and - sometimes - learning. What convinces people to dedicate hours, days, or even years to the pursuit of learning? Here are some of the most common reasons - learners may exhibit multiple at a time or move between them, but if you are designing experiences to encourage learning you should be intentional about which ones you emphasize. Read more ›
It’s exciting to help a company expand into a new customer segment or line of business, but it’s also daunting - where do you begin? Expanding on my earlier writings, this post offers a roadmap for going from a vague direction to a compelling, high-confidence product strategy in the space of a month. Read more ›
Empowered product teams form around a charter: a long-term objective or significant customer problem that the company wants to address. As ambitious as the goals may seem at first, teams can and do complete their charters; leaders need to recognize this and step in to prevent the team from languishing without clear direction. Read more ›
On the way to building a hugely successful company, most startups will need to expand from their initial product-market fit to a portfolio of successful products. Building a new business in an established company is similar to building a brand-new startup, but has some unique nuances that can make or break the initiative. Read more ›
Like startups, new lines of business in existing companies typically go through a consistent lifecycle. Comparing these to the stages of a startup can be a convenient shorthand for understanding the maturity of the idea, expected challenges, and level of investment. Read more ›
When you want to change policy, show, don’t tell. Start by creating the change within your local environment, demonstrating the benefits, and encouraging others to try it. Once you’ve proven out the playbook and earned enthusiastic support, then advocate for a formal policy change. Read more ›
As product+engineering+design (PED) teams grow from 2 to 15+ people, they tend to face similar challenges and adopt similar structures and processes to support their growth. By outlining some of the best practices I’ve seen for teams of different sizes, I hope this post helps others stay ahead of challenges and identify strategies for dealing with growth. Read more ›
When writing long-form informational content, state your main point first and then reinforce it with additional detail and arguments. Neither you nor your readers should need a “tl;dr”. Read more ›
The decision to build a particular feature or pursue a certain goal is at the core a prioritization decision: should we go down this path as opposed to all the others. It is considerably easier to make a good decision if those alternatives are presented explicitly, rather than just the single-pronged “should we do X?” Read more ›
Time, cost, quality - for any project you can specify hard constraints on at most two of these factors; where the third ends up will depend on luck and skill. Read more ›
Many startup founders end up tying their sense of self-worth to the success of their company. This is dangerous in good times and crushing when things go south. If you are close to a founder whose startup is struggling, try to make them feel like a loved, valuable person independent of their business. Read more ›
Our former head of engineering Raul once shared this wisdom: a junior engineer will say “we can’t do that, it’s impossible;” a senior engineer will say “we could do that, but here’s the impact to the business if we do…” Read more ›
“You are not your user” is a common adage in the world of product and design, and is particularly true when building products for K-12 schools. In the fall of 2019, I gave a talk at EdSurge Immersion on my favorite “you are not your user” insights from five years of working in edtech. Read more ›
Before starting on a new project, teams should write down target metrics that they expect to hit if the project is successful. A helpful format is to measure and set goals around the following three metrics: are people aware of the project, are they using it as expected, and is it producing business outcomes. Read more ›
Low fidelity paper prototypes and wireframes are great for feedback on usability, but realistic looking high-fidelity prototypes like mock screencasts are much more effective at assessing desirability of new products. Read more ›
When building a new product, first find the burning customer problem, then tie it back to a business objective. Too often teams focus primarily on the business needs – e.g. “we want to convert MAUs to DAUs” or “we want to sell into larger enterprises” – rather than the customer needs, resulting in motivated reasoning and mediocre products. Read more ›
From New Year’s resolutions to diet or exercise routines, there are behaviors I know I want to do, and yet when given an option I don’t always choose what I know I want. This is surprising! To resolve this contradiction and convince myself to act in my own best interest, I use a notion of “persuasive memory” Read more ›
In taking a product from conception to release, a product manager is bombarded with feedback, ideas, and constraints all pulling in different directions. A unique and essential responsibility of the PM is to make sure that the product that comes out of this gauntlet still makes sense as a coherent whole. Read more ›
Getting a first job as a product manager can feel like a catch-22: most companies will only hire product managers with prior product management experience. If you want to be a product manager, there are three paths that I’ve seen: landing an Associate PM role at a big tech company, joining a company in a “product adjacent” role, or taking a “generalist” position at a small startup. Read more ›
Customer-facing teams are inundated with feedback from customers, and in turn tend to inundate product managers with far more requests than can be prioritized. A simple technique to maintain a reasonable backlog while making customer-facing teams feel empowered is to ask each team to identify and advocate for their top two, and only two, product requests. Read more ›
As products mature, I like to start “layering” goals and objectives so that our efforts this quarter help us achieve our annual plan, which in turn will get us closer to our 3-5 year vision. To build these long-term plans with my team, I first start by getting everyone on the team to create an artifact I call the “3x2x1” that promotes long-term thinking, forces tradeoffs, and helps people persuasively express the direction they think the team should take. Read more ›
One of the best ways to improve your product is to ask your newest customers what they think your product does, and then make it a reality. Read more ›
Every few years, a new diet becomes popular: Atkins, then Paleo, then Keto, then Gluten-free, each one developing a following of people who swear the diet helped them lose weight. My unsubstantiated theory: while each diet makes grand claims about its underlying science, I suspect these diets work, at least at first, for a much simpler reason: they make it hard to find food. Read more ›
Leveraging concepts about debt from the financial industry, such as “interest rates” and “maturity” can help business, product, and engineering leaders find common ground when debating whether to build the quick, hacky version of a project, or take the time to build it the right way. Read more ›
Being data driven can help your company ship better products faster. You can cultivate a data driven culture in your company in four stages: stimulate curiosity, quantify past wins, estimate impact of projects in flight, and finally use data to prioritize future efforts. Read more ›
A good gauge for product success is whether customers are “pulling” the product into being with their requests, or whether the company is “pushing” the product along in search of growth. This is a easy, practical way of determining if you’ve found product-market fit. Read more ›
Most companies want to be "data driven," but there are few concrete, prescriptive guides to what this actually means. This is an opinionated framework derived from my experiences and conversations with other startups. Read more ›
For the last 6 months at Clever, we have organized our engineering teams around the type of user rather than the part of the product. The result has been increased collaboration, deeper insights, and an explosion of new product ideas. Read more ›
"If you assume both people are intelligent and rational, then the only way you can have a disagreement is if you are looking at different data." Read more ›
This is one of my favorite presentations, and forms the basis for much of the way I think about early-stage product management. I recommend going through it every few months to keep the lessons fresh. Read more ›
Why is it that websites require you to reset your password, instead of just reminding you what it is? After all, they check your password when you enter it, can't they just look it up? It turns out the answer is no - websites actually don't know your password, and instead use a technique called "hashing" to check if what you log in with matches what you set when you created your account. Read more ›
Giving positive feedback is easy; it’s much trickier to provide critical feedback in a way that improves the end result without diminishing the sense of ownership of the person working on it. In situations with designers, engineers, and direct reports, I’ve found one technique that works well is to focus on identifying issues rather than offering solutions. Read more ›
Time cannot be found nor had, it can only be made. The difference between the attitude of "I didn't have time" and "I didn't make time" is substantial: if you think of time as something you have to make, you assume ownership and responsibility for your time in a way that many people often avoid. Read more ›
Express your ideas with conviction, but be willing to drop them and adopt better ideas as they come along. The best leaders and organizations are those that are pragmatic. Here at Filepicker.io, we say "Strong Opinions, Weakly Held" – a concise and effective way of encouraging active debate and the meritocracy of ideas. Read more ›
If you are a programmer working on a startup, force yourself to spend a day working where you don’t write any code. Seriously, do it, and make it a habit — you and your company will be greatly benefited. The time’s I’ve done it here at Filepicker.io have paid off in spades. Read more ›
A number of developers have asked recently why Filepicker.io passes around everything as URLs, and to me the better question is why more serivces don’t pass everything around as URLs. Read more ›
Many conversations about the future of computing revolve around the eventual fate of the “File.” After all, most tablets and phones don’t show the user anything that resembles a file, only Apps that contain their own content, tucked away inside their own opaque storage structure. Read more ›
Or "How I Learned to Stop Worrying and Love the MVP." Read more ›