Google sometimes drops the ball because Google is a massive company

The other day I finally subscribed to Connected, a great consumer tech podcast, and in their most recent episode, Federico rants about the inconsistent feature support across Google’s iOS apps. (He ranted about it 2 months prior, and the rant still stands.) They’ve failed to provide consistent support for now-core iPad features, including support for the iPad Pro’s bigger screen and Split View. How can you write in Google Docs and do research simultaneously without split view?

Not even being sarcastic. I have to imagine it’s really annoying and hard. If I had an iPad Pro, I’d probably agree with him; in fact I’d probably stop using those apps altogether until Google made them work for me. It sucks even more to notice that Google has updated some of their apps with support for these features. But why not the others, arguably the ones that are the most widely used purely in a productivity context?

I was listening to his rant on my way into work – a place of work where I am one of over 4,000 employees. I started thinking about the different projects that are in flight at any given time within my company and reminded myself: I have no idea who is held accountable for some of those projects. Who knows if they have the same priorities that I do? In just nine months at my current company, I’ve had to deal with multiple fits and starts around projects that involved multiple key teams, only to find out that those teams suddenly had to prioritize these same projects completely differently than mine, due to other external factors beyond my control.

Google is an even more massive organization. It has over 10,000 employees working on any number of products or initiatives. There are teams of hundreds dedicated to Google Docs, Google Sheets, Google Drive, even just the different iterations of messaging (Hangouts & Voice & Chat across all platforms). Each of those teams contain different people, each with strengths and weaknesses and a certain propensity to work harder or less hard than others, or even make occasional mistakes. They also may have different priorities, backlogs and possibly even internal politics.

We have to remind ourselves that each of these factors may translate into different results per product. I would bet that Drive (which coincidentally I think is one of the best Google apps on iOS) has a lot more of its core functionality together and had the capacity to fit split-view support into its roadmap shortly after it was announced. Docs (or more specifically, Docs for iOS) is probably run by a different team that still hasn’t been able to prioritize one of these features. Or perhaps they have it built and in a testing phase, but some QA analyst ran into a massive, crippling bug that Spilt View caused in Docs for iOS but was not a problem in the other iOS apps. Maybe there’s another feature they’ve been pushing for that took precedence over Split View or caused a UX problem when rendering on the larger iPad Pro screen.

Remember when Google+ finally got its Material Design update for iOS almost a year after it did for Android, even after people declared it dead? Why does the Google Analytics, one of the most widely used Google business tools, have a terrible iOS app with an outdated icon and no 6+ screen support? When was the last time anyone tried out Google Earth for iOS? Did you even know that Google has a dedicated Street View app separate from Google Maps? Who decided to make that?

These apps are different priorities for different teams under the same friendly Google brand, so we can’t be surprised when their adoption of features or design principles aren’t totally consistent.

Managing a product roadmap is hard. Managing a roadmap for a single product that plays nice with the roadmaps of other products under a single company is exponentially harder. As frustrating as it can be to see individual products under a brand fall behind others, it’s worth reminding ourselves about these difficulties – especially with amazing new features on which we rely in some contexts of our daily lives.

Eight months, in an office

10 months ago, I was living what I thought was a dream: working remotely for a decently-buzzed tech startup where I was the lead product guy. I could work in my underwear, start and end whenever I wanted, have free reign to work and travel wherever I pleased.

Then in May, said startup laid me (and pretty much everyone else) off with a week’s notice.

I had seen this coming for almost a year for various reasons I won’t get into – but what did surprise me was the ease of getting back on my financial feet. Those of us who got laid off were offered a new job pretty quickly by Wayfair, an e-commerce giant also based in Boston. So that’s where I ended up.

Eight months later, I find myself finally in my element again. The first three months in this job were total culture shock: I was uncomfortable around so many people, all of them wanting to talk to me all about the work and nothing but the work. I was frustrated with having to commute to an office at all, let alone walking down the street like I would regularly do in New York.

But over the last few months, I figured out a rhythm to make it work for me. It’s certainly not a perfect situation – but then again, what job is, really? – but I’ve had some time to reflect about being in an office again.

(Disclaimer: this is primarily about the experience of working in an office environment, particularly after a stint in startup culture, and is in no way intended to be a reflection of the work I do, or my employer, at all.)


Wayfair employs thousands of people and has an office right next to Copley Square in Boston. When you walk into the office for the first time, it’s hard to not feel like you’re part of something massive, given just how many people are flocking to the Copley Plaza complex between 8 and 9am. You’d think one of the stores in the Copley Plaza Mall was having a blowout – nope, these are just Wayfair employees trudging into work.

After a few weeks, though, the awe of big company size and impact turns into drone-like fatigue…especially as wintertime sets in. Droves of sleepy, freezing employees passing through subway turnstiles, huddling underneath half-broken umbrellas and avoiding puddles of slush (and being forced above ground to avoid MBTA construction), just to stare at a PC screen and talk in corporate-speak.

Simply having to be at the mercy of weather sucks. When I was working from home, if it was snowing out, I could just stay inside. I technically have the facilities to work from home in my current job, too – so it can be frustrating to eschew all this technological capability just to be present in the office culture. Wayfair has offices in several locations around the US and Europe; I can’t tell you how many times I questioned my battling of snowstorms to get into the office, only to sit on calls with my Berlin colleagues all day.

That said, if you’re stuck on calls all day at home, you might never leave the house. Get this: working in an office forces you out into the world. This is something I completely took for granted as a remote worker – I would occasionally run out to a coffee shop for a while to get stuff done, but nothing was more comforting than parking it on my couch for 9 hours straight save bathroom and lunch breaks.

Speaking of which, when you begin to compare home-work and office-work life, tiny subtle details start to surface about your lifestyle. For instance, The cost of your utilities start to become something you scrutinize monthly – I drastically underestimated how much I was spending to run electricity and heat during the ’14-’15 winter while working at home. Finding food to eat in an office is a really hit-or-miss thing, depending on where your office (or home) is located. I have the benefit of being right near Copley Square, where food trucks and solid restaurants abound. My last office job was in an awkward part of East Cambridge, MA, where our best culinary options were in a mall food court. At home, you’re really at the mercy of your grocery list or what (if any) restaurants are nearby; back in NYC, this wasn’t a problem, but in quieter parts of the world, this could certainly be a drawback.

Everyone who Product Manages knows the difficulty of trying to herd cats – oops, I mean colleagues – toward a shared product vision, and this difficulty is only amplified when doing it from afar. Being in the office ensures presence from everyone who matters, including my/yourself. I find myself more productive overall, simply because I had face time with colleagues working on projects with me – and no at-home distractions, like my guitars or my television. I can also use my commute to unwind and/or focus on things I’d never be able to focus on given those distractions. I’ve started writing again simply because I have over an hour of “free time” on the train every day.

Working in an office can be painfully social. To avoid talking only about the work, you need to find common interests with your colleagues: in Boston, it’s generally assumed that this is Boston sports. If you’re not actively following the Bruins/Pats/Sox (or worse yet, following another city’s team) you’re already at a disadvantage. I’ve come to develop a personal brand around music snobbery, pop culture savvy and a more casual tone, which people seem to appreciate outside of my general apathy for sports.

Once you figure your general vibe out, though, working in an office can be delightfully social. You actually start to make friends and engage in social conversations and outings you never would’ve had sitting at home or in a coffee shop all day long. Sure, there’s spontaneity involved with serendipitously meeting new people at your local coffee shop, but there’s something equally spontaneous in the side conversations that happen at work. My aforementioned music snobbery may manifest itself during a discussion of weekend plans, which may lead to a colleague/friend to check out a band with.

And what happens when the work gets to be too much, and you find yourself stuck at the office all day? Isn’t that the beauty of working wherever you choose? What about those giant cultish companies who directly incentivize their employees to spend all waking hours at the office, or even sleep there?

Well, so, you can just leave. If there’s more work to be done, and your company has a VPN, you can catch up on work at home after having a lovely dinner at a reasonable hour with your significant other. I’ve come to realize (again) the importance of balance – not necessarily the lofty, unattainable “work/life balance” construct of 9-5, but finding a personal balance where I’m challenging myself and working hard, but not burning myself out and still finding time to reflect and find fulfillment elsewhere in my life.


Certain parts of the tech/startup industry paint office culture as a thing of the past, rendered unnecessary by new collaboration technology. Fully-distributed organizations are popping up everywhere, promising uber flexibility and balance. I admire these companies’ ability to embrace technology to try and bring more happiness to their employees – though it is certainly not perfect either. Remember that distributed companies (or remote work at all) is a fairly new concept, far from perfected by any one organization – and the larger the company is that you work for, the harder it is to adapt the necessary processes and technology to enable that flexibility.

All in all? I certainly don’t hate everything. My commute is sometimes frustrating, as can be the work, but that’s part of dealing with everyday life. I genuinely like quite a few of my colleagues (both in and outside of work), which after being remote for a while is quite refreshing. And I’ve achieved a balance that, at least for now, I’m happy with.

The question I now find myself asking more frequently is: where does this go? Do I advance up the food chain of a strong brand with its corporate quirks, or do I keep my hand in some things that could result in more personal freedom? What will ultimately make me a better, happier person?

Well, how many licks does it take to get to the center of a Tootsie Pop?

The problem of task managers

Wunderlist, Trello, Todoist, OmniFocus. 2do. Things. I have to imagine that most smartphone users haven’t even heard of these apps. That's probably why there's such an apparent subculture around each one. The average person will never break into the most beloved apps, and those who do will defend it to no end.

So why don’t so many people, who presumably have things they need to do in their lives, use one of these tools? For all the people that do try a project management tool, why do so many underutilize them?

Everyone has a smartphone, and most of them probably use stock functionality (read: Reminders & Calendar) to keep track of their daily lives on that smartphone. However, Reminders rarely has accountability – what if you forget to set a reminder time? What if you miss the location-specific notification by the time you’ve left? What if some to-dos are dependent on others and you can’t check them off the list until some other thing you neglected gets done?

Are the to-dos I’m getting reminded about even a good use of my time right now?

What about the big important complicated things I want to do?

How do I even break those things down into the little to-dos to put in my list?

What does that mean to me in the big picture?

The average person doesn’t want to (and almost certainly can’t) think through all that stuff, even though they potentially have implications on their daily lives.

This conundrum, in the workplace, is basically why project and product managers exist. Product managers help to figure out the right things to focus on and why; project managers make sure they happen so you, Mr. Stakeholder Guy don’t have to worry about all the little details.

Personal assistant apps exist, even virtual ones, to remind you of upcoming meetings and tasks – so why haven’t we developed a “personal product manager” that takes your big goals in life and helps you break them down and focus on the most achievable pieces of said goal?

I think about the big things that I want to eventually do in my life – get married, build a company, buy a house, be a notable musician, other things – there’s a ton of knowledge of what to do to make those things happen on the Internet. But parsing all that information is a nightmare – you’re basically relegated to Google searching or starting with blogs/resources you trust and vetting the content endlessly until you end up with a series of tasks, which may or may not be in order, prioritized or even possible. Then, you have friends and/or family as a resource, which may contradict your online findings (or even each other). I don’t even want to think about the difference between my dad’s opinion on starting a business compared to my previous employer.

Productivity apps can’t do this thinking; it’s not what they’re designed to do. 2do, one of my favorites, requires a whole lot of task creation and organization in order to be truly useful. and People have said that about Evernote, too. Trello is great for visualizing projects in a board format, but it doesn't tell you what should populate that board and what of that stuff needs to get done in order to make BIG AMAZING GOAL X happen. (That's probably why they've started collecting and sharing sample boards for various use cases.) The thought process around focusing the idea into discrete pieces hasn't been productized for personal lives.

I wonder if this is why productivity apps aren't ubiquitous – because they exist to humor the details of lives instead of boiling them down to what’s important.

Misanthropy in product management

When I started product managing, I quickly came across and fell in love with the Cranky Product Manager blog. It was everything that I had just started to experience as a new PM — the constant fight for attention in the roadmap, the terribly-defined feature requests, the working ridiculously late for reasons I couldn’t really justify for myself. That blog is no longer active, but the feelings are still alive in many of the PMs I talk to around Boston and NYC — and they haven’t really gone away for the most part.

In my five years managing products I’ve learned to separate my work frustrations from my personal life, not burn myself out and communicate better — yet I’m still at the mercy of external forces: stakeholders not being honest about their requirements, teams not communicating with each other, salespeople overpromising to clients, founders falling back to buzzwords, people being lazy.

And you’re ultimately accountable to deal with all that as the product owner.

This photo intentionally left blurry to signify my hand-shaking frustration.

With all the hyper-positive blogging out there about exciting new products, startups and giant companies doing great things (which I love, don’t get me wrong), it’s worth remembering that in many cases, Product Management is largely a tough, punishing, thankless job, and I’ve found that it’s a little more manageable when you reduce your trust in people just a little bit. This isn’t a bad thing, really — we’re reminded as product builders to test out others’ hypotheses, second-guess user feedback, question assumptions and your options are to blindly follow or question. Both of which lead to a frustrating and/or misanthropic end.

Don’t get me wrong — I love building and managing products, solving challenging problems, and creating awesome user experiences. But I have a little less faith in people as a result of that passion.

(That’s probably why so many PMs end up trying to build their own products instead of building for others. Maybe I should finally try that.)

Want to learn more about who I am and what I do? Go to my website or tweet at me and we’ll hang out.