let us be excellent at resting

We are so excellent at working. Let us also be excellent at resting.

My yoga teacher said this once in a class some time ago. I remember being amused by it at the time but the more I've thought about it since then, the more I've come to appreciate the power of those words. 

The need to work hard is a concept that I imagine most successful people espouse. And of course, how can you succeed without putting in the effort necessary to do so? However, I think that after some point, the effort you put in isn't proportional to the value you get back. This can manifest itself in different ways: resentment, a drop-off in quality, even the inability to complete the work. Whatever these indicators are for you, it's important to recognize as they're happening and find your path to rest. But then what?

In a typical yoga class, as the class comes to a close, we start to transition into savasana, or corpse pose, which is exactly what you might expect it to be. After this process of resting and resetting, I find that I approach the rest of my day with more joy because of it. And in the context of product management work, there's one thing I always do after my professional savasana, namely strategic planning.

As a PM, there's always tactical work that needs to be done and there's a hit of satisfaction at completing those kinds of tasks. That instant gratification doesn't really come with strategic tasks but these are often the most important projects that a PM needs to make time for, whether that's defining the long-term roadmap, identifying the next big area to focus on, or planning the future teams that will need to built out and their rationale. This is what allows you to make huge leaps forward, rather than taking small incremental steps.

It's hard to get into the zone on this kind of thinking when your brain is focused on completing tactical work but making the time for rest helps cleanse the brain. Then, following that up with focused time for strategic thinking can really help you get to the next level of your product and set the stage for the future.

impractical etiquette

“Let it be hoped that impolite New York will wake up before it is too late and resort, not to its etiquette books, but to common sense and natural kindliness, which, after all, are two things always at the bottom of real courteousness.”

-- The New York Times, 1907

As our world has evolved and become more mobile, what we consider "appropriate" has greatly changed. It sometimes feels like people experience the real world through their phones. Whether it's checking email out at dinner, walking through a museum looking through the camera or talking to someone on the toilet (not me, but I have heard this happen in public restrooms...), smartphones have redefined communication. And with the rise of wearables, all these devices fundamentally change societal expectations of how people should interact with each other.

But when it comes to evolving notions of interaction in a mobile world, it seems like wedding etiquette hasn't changed at all. Despite the fact that the amount of mail handled in the US is steadily going down (see this awesome USPS chart), and your phone is almost certainly the most practical and ubiquitous way to reach you (although not by calling), people seem genuinely shocked that we're planning to send our wedding invites digitally. 

As a PM, I hate inefficient workflows. Forget the material cost of sending nice paper invites (invites, envelopes, liners, stamps, etc.), which isn't actually my main concern  Instead, just think about the sheer impracticality of sending invites:

• get everyone's mailing addresses (do you know where anyone lives anymore?)
• put all the addresses into a spreadsheet
• print out all the labels or handwrite every address
• stuff the envelopes
• seal the envelopes (and hope that this doesn't happen)
• put everything in the mail and hope it doesn't get lost

That doesn't even include the work on the guest side to RSVP and then on our side to actually track the RSVP and the nagging to RSVP. Let's also not forget the communication back to the venue. I could go on but I think you get the idea.

Instead, our digital invitations hook up to our mobile wedding app and existing cloud-synced contact lists, auto-track opens and responses, allow customized questions, and directly add everything into a spreadsheet that can be sent to the venue with one click. If anyone doesn't RSVP, we can email, text or call them to nudge. From a product perspective, there is no question how much this flow is improved by software. Normally, people would cheer the lack of paper, the productivity improvement and the overall ease for every party involved. And yet, there are an astounding number of people who believe sending digital invitations is disrespectful - a major faux pas.

There are interesting sentiments at play here relating to (im)permanence and communication, which I'll save for another post. For now, I'm going to brave the naysayers and send out digital invitations anyway. I hope our guests appreciate it. :)

And as a follow up, here's a great piece from The Atlantic about evolving telephone etiquette.

being dangerous

As I've approached opportunities in my career, one thing that's always been important to me is that each new job or project is in a space that I know nothing about. Whether that's going deep into a new product area, or starting a completely new job in a different industry, I've always enjoyed an opportunity to learn new content.

And each time I start something new, that feeling of ignorance is a driver to learn as much as possible and become a subject matter expert in a short period of time. However, as I've been working on building out my consulting business, I find myself peeling back a bit more and rather than becoming a true subject matter expert, it feels like the right knowledge line is knowing just enough to be dangerous.

Normally, this would seem like a bad thing. However, I've found that knowing just enough to be dangerous causes me to ask questions that only true subject matter experts can usually answer. What this means is that when I'm working with companies, my "dangerous" questions either help reveal areas where people need to go deeper or clarify the understanding for everyone in the room.

Obviously, Google, Wikipedia and research reports (Gartner, Forrester, etc.) are the first sources but reading a lot of content doesn't quite go far enough. Part of being dangerous is not just knowing the content, but also absorbing it by applying it in context. To get quickly up to speed on a new area, I've found the following approach to be helpful:

• create your 30 second description of the area and tell it in a compelling way
• identify key blogs in that space and read the most popular articles on those blogs
• create the list of high-level topics that an expert would know in-depth
  • for each of those topics, create the one to two sentence description
• know the 3-5 top competitors and how each seeks to differentiate
• identify the challenges that companies need to solve to succeed
• create a list of successful parallels/metaphors in other spaces

Clearly, this only scratches the surface but I've found that for me, it provides a great framework for helping startups to go deep and be truly dangerous rather than just superficially so.

beyond the tip of the iceberg

Typically only one-tenth of the volume of an iceberg is above water. The shape of the underwater portion can be difficult to judge by looking at the portion above the surface. This has led to the expression "tip of the iceberg", for a problem or difficulty that is only a small manifestation of a larger problem.

One of my colleagues at Redpoint, Mahesh Vellanki, recently posted a great article on key elements of good consumer marketplaces. In addition to these things, I think great marketplace companies build great products that solve the problems below the surface.

The consumers of on-demand startups usually use only the consumer-facing app. Unless they are part of the supply chain or work at the company, people aren't aware of the products that serve the supply side or the ones that employees use to manage the company. However, these products are equally, if not more important, because they connect all the actors in the marketplace and drive all the vectors of the company. 

Building great supply side and marketplace products face a number of challenges, including:

• lack of good product and design patterns
  • Unlike consumer apps, these products aren't easily downloadable. You might need paid accounts to sign up, and people generally aren't posting screenshots of these products on the internet. Also, if these are internal products for employees, they contain sensitive information and would need to be thoroughly scrubbed before someone could even consider posting them. Fundamentally though, these products are a competitive advantage for the business so sharing them broadly isn't what companies are likely to encourage. 
• lack of user knowledge
  • A key part of being a good PM is walking a mile in the user's shoes. It's hard to be a true test user of these products and their flows without immersing yourself in the role for some period of time. Given the demands and constraints of a PM's time, making the time to do this, critical as it is, often gets pushed to the wayside. As a result, the people developing these products don't always have the strongest understanding of how these products can be most effectively used.
• catering to all levels of expertise
  • These products have users who are just starting out and must quickly get up to speed (first day on the supply side, first day as a new employee) as well as extremely experienced users who have been on the system for years. Intelligent products will understand the level of experience of the user and adapt themselves appropriately, using wizard interfaces and quick templates or advanced controls depending on the person. In creating these products, the PMs and designers need to have a deep understanding of what tasks need to be accomplished and how much guidance needs to be provided by the product to finish those tasks quickly and accurately.

Despite these challenges, great marketplace companies have built great products behind the scenes. So, when looking at marketplace companies that aim to scale big, it's critical to look at the products beyond the tip of the iceberg. Because even the sexiest consumer mobile app in the world can't make up for a disorganized supply chain and chaotic operations. 

mobile commerce musings

Most (if not all) on-demand companies would never have existed were it not for smartphones. Mobile phones allow us to satisfy the need for instant gratification and on-demand applications because they're always with us. Sometimes, it's for the better (check in for your Southwest flight exactly 24 hours before) and sometimes it's for the worse (checking work email when out at dinner with your partner).

Of course, a big part of the power of mobile is being able to pay with your phone, not necessarily directly with Apple Pay but even just to be able to store mobile card credentials and then easily access/add/change them in apps. That's what makes the Uber experience feel so frictionless - get in, ride and get out. However, again with the notable exception of Apple Pay on the iPhone and Apple Watch, I'm not aware of how people are using some of the unique features of a smartphone to enable commerce. These include:

• ubiquity
  • it's always on you (except of course when the battery is dead)
  • it's always on others (battery exception as above)
  • US smartphone penetration was 76.6% in early 2015 according to Comscore
• camera
• contacts
• location

You could argue that some of these features can also be accessed on the web, which is true, but in no way are all these features as accessible and accurate as they are on mobile. Also, you're hardly going to whip out your laptop at an in-person retail experience. Given that, here's a first pass at some products that I think could make for interesting mobile commerce ideas:

1. pay with friends
   • You pay the full cost of an item and then add friends who are supposed to chip in for the item from your contact list. The cost gets automatically split and you get refunded back to your bank account directly through ACH. I could even see this turning into a reverse credit card lottery game for credit card reward optimizers. Among a group of friends, everyone's vying to get their credit card to be the one that "wins" because they'll earn all the rewards, whether cash back, travel miles, etc. It can be an ongoing game that tracks stats among friend groups and amplifies engagement through other features. 
2. pay by picture
   • Snap a picture of a receipt with your camera, which then OCRs the info and allows you to tip and confirm payment. This would be nice at busy restaurants or bars because you wouldn't have to wait for a server or bartender who's slammed with requests from other customers, especially if you're in a rush. There are some problems here in that it's now on an honor system. That might be solved by also having you manage the order through an app (a la Coaster or Open Table pay), guaranteeing that the venue has your card info and authorization for some specified period of time. If you walk away without paying, the card can still automatically be charged. This is a tricky thing to get right from a UI and experience perspective though.
3. pay at a location
   • At major venues like stadiums or arenas, people tend to get spendy because of food, beverage and merchandise. They also often buy these tickets online. Detecting your availability at a specific location for an event could automatically launch a catalogue specifically for you and for that event and allow you to buy those items from the comfort of your seat. At an appropriate moment for a break/whenever you get a ready notification, you go to a separate area where you can just scan your phone and unlock a locker with all of your purchases inside. No waiting in lines, no receipts and it gets automatically charged to your card. This one clearly requires the most operational work but if it leads to greater and more frequent spend, it might still be worth it. It could also be considered a premium feature that's only unlockable by people with elite credit cards such as an AmEx Platinum.

If any of you are aware of companies that are doing similar things or have other interesting plays in this mobile commerce world, I'd love to hear about them so please send my way.