The Friday List at #neato – 2015.05.22

A few interesting articles I’ve bumped into this week, curated from my Pocket and shared for your enjoyment. I read some cool stuff this week around new use cases for the Apple Watch, real-life startup soap operas, and Slack’s product/market fit. Happy Friday!


“How the Apple Watch is opening up new ways to communicate”

There have lots of back-and-forth commentary on how hard the Apple Watch is to use, how the interface is weird and non-standard, etc. It’s great to see a more expansive look at how wearables will impact different groups of users.

“731 Slack Users Reveal Why It’s So Addictive”

A good look at what users find so compelling about Slack, and a set of analysis that highlights how important product/market fit is.

“Clinkle Implodes As Employees Quit In Protest Of CEO”

I learned about Clinkle and its storied past a few months ago and find the saga super interesting. Massive early funding, unclear product direction and a discerning amount of secrecy have caused this to be what sounds like a terrible experience for their team.

“Workflow Hints At The Future Of The Watch As A Computing Platform”

Another post about the Apple Watch, can you tell I’m getting mine soon? I think it’s fascinating to see lightweight workflow scenarios that could really change how we use mobile and wearable computing. IFTTT changed how I used my Android when I first got it and apps like Workflow could open up similar scenarios for the watch platform.

A Product Manager Should Be The Most Curious Person In The Room


image (C) Tauntaunwampa

I was talking earlier this week with a new product manager on my team. It was our 1:1 and we were discussing his latest project. It’s the first big product area that this PM has taken on and it’s very important for our next release, so we were using our conversation to make sure everything was on-track. I was peppering him with questions after he shared his update:

“How do you feel the project is going?”
“What challenges have you hit working with your feature team?”
“Is the spec ready for review?”
“Okay, can you show me the diagram for the main use case that you’re stuck on?”
“What about this part of the lookup, can we also double-back with the phone number?”
“I just thought of these two uses cases, have you considered them?”
“What’s left between now and the spec review?”

Later that same day I was in a feature team meeting discussing the status of a new product offering. The lead developer was sharing his detailed update, which included a few specific areas that had risk and ambiguity.

“Why did you choose that implementation path?”
“Will this scale if we 10x the amount of users in a year?”
“Is there a faster way to do it?”
“What if we added more resources?”
“What are the biggest remaining risks?”

Folks who have worked with me before know that I love to ask questions. A lot of questions. 🙂 The questions I asked during the 1:1 with my PM (and their resulting answers) helped me quickly understand the status of the project and where he was blocked. It also set the stage for the type of information I’d want to hear in the next update I get about the project. He and I then spent a few minutes talking about questions, curiosity, and why they’re both so important for Product Managers to be effective in their careers.

Awesome Product Managers have an unrelenting sense of curiosity. They’re equally curious about the latest competitive apps, their own project statuses, industry news, how a piece of backend technology works, the reason a bug occurred, or why a partner team is late on delivering. A great PM should use precision questioning to drill into every conversation and problem to understand what is really going on and what they can do to move things forward. This can reveal gaps in use cases, technical knowledge, or even a partnership agreement that need to be addressed.

Checking for curiosity is critically important when evaluating a PM for a role on your team. Many parts of my PM interview process, from the “What’s your favorite app?” question all the way through the product design case study, are used to see how curious the candidate is. Do they start out the case study by immediately jumping into a solution on the whiteboard based on something they know, or do they open with a set of questions back to me to help understand what they don’t know.

Ultimately your use of precision questioning as a PM must be balanced with the amount of investigation and discovery you do on your own. You will also gain a lot of experience over time simply from being in more and more product cycles.

The simplest way I can frame this advice? Don’t wait if you’re curious about why something is. Get curious and ask the question.

The Friday List at #neato


A few interesting articles I’ve bumped into this week, curated from my Pocket and shared for your enjoyment. This week was full of good reads on growth strategies, the health benefits of standing desks in elementary schools, and why some men lie about working so much. Happy Friday!

Should Your Kids’ School Have Standing Desks? These CrossFitters Think So

I’ve had a standing desk for eight years and love it. My back, legs, and overall body has felt better compared to when I sat in a chair. Have you ever tried it?

“Why Some Men Pretend to Work 80-Hour Weeks”

This was a really interesting study. I often feel compelled to work as much as possible (read = I enjoy working), but it needs to be my choice. Corporate cultures that prevent you from making that choice can be really damning to overall employee health and productivity.

Google will reportedly let Android developers A/B test apps on Google Play

At Contactive we tried to test our Google Play descriptions but had to do it manually (and sequentially). This will be really helpful for app developers as they can quickly test pricing or description content.

A Founder of Secret, the Anonymous Social App, Is Shutting It Down

I don’t think it’s wrong that the founders took $3M each and bounced out. Isn’t that better than running a company into the ground?

The Friday List on #neato

A few interesting articles I’ve bumped into this week, mostly curated from my Pocket and now shared for your enjoyment. This week saw some Apple Watch UX predictions, an interesting AMA on Windows Metro, and a discussion on whether you should be penalized for showing up late to Crossfit. Have a great Friday!


Here’s Why You’ll Hate the Apple Watch (and the Important Business Lesson You Need to Know)

Nir Eyal makes a great point about something super simple: being able to easily tell the time with the Apple Watch. I’m excited to get mine (June pre-order!) and will see if this is as big a problem as he say.

Ex-Microsoft Designer Explains the Move Away from Metro

I’ve always been a fan of Paul’s site since my early days at Microsoft. I worked on various products that were either impacted by, or a part of, the Metro effort and this article makes me feel equal parts annoyed and relieved.

Why Big Data Matters To Every Business

I really like Bernard Marr’s commentary on the state of the tech industry. This isn’t a technically deep article but covers the landscape of big data and it’s relationship to business strategy and the internet of things.

Burpee Penalty in the Gym: Smart Tool or Stupidity?

My gym, Crossfit South Brooklyn, doesn’t have a penalty if you show up late to class. I think if you show up later than 5 minutes you can’t join (since you miss the warmup and lessons). I have visited gyms in other places that have burpee penalties. What do you think?

How I Grew My Network By 142 People Last Month


I’ve always loved meeting new people. My mother will recall that when I was a child I would walk around the play area at my kindergarten school, offering up whatever toy I had in my hand to other kids in an attempt to get them to share and play with me back. It’s been 30 years of meeting new people since those days back in kindergarten, and I can honestly trace all of the internships and jobs I’ve ever had directly back to a specific person in my network. I actually share the story of those connections during a talk I give annually to my old high school, “Shaking Hands: How I Networked My Way To A Career I Love”.

I also love using systems and processes to help make my work and life more productive. Over the years I have evolved the way I network to try and make it as efficient and fun as possible. A friend recently asked me how many new people I met last month, and I think I startled him when I said very quickly and specifically “142”. Yes, I track how many new people I meet each month, thanks to a few tags in LinkedIn and, of course, a process. 🙂

Here’s the thing, though: you don’t have to be an extreme social extrovert to grow and benefit from a great network. I believe with a little process, a few funny nametags, and a touch confidence, anyone can grow a great network.

I believe there are three parts to building and nurturing a great network:

  1. Set goals.
  2. Make a plan, get prepared.
  3. Be diligent, follow-up.

1. Set Goals

What are you networking for? Having crisp goals makes it so that you maximize the time and effort you spend growing your network. It’s okay to have multiple goals, but don’t have too many or you will lose focus. These goals will then help you plan out the content, people, and events you need to be most effective. My current networking goals are:

  1. Hire a new Product Manager at ThinkingPhones.
  2. Find new business partners for a specific product at ThinkingPhones.
  3. Find new business partners for Perspyre.
  4. Grow my network in the NYC startup community.

For each of my goals, I write down a 2-sentence “opener” that I can use when talking to someone about them. For my goal of hiring a new PM at ThinkingPhones, I use:

“I’m looking to hire a PM with five or more years of experience to join our NYC team and focus on building our new UC and big data clients. I’d ideally like them to have experience building mobile apps and working with remote teams.”

Now whenever I bump into someone at an event I have these quickly queued up in my head and ready to go.

2. Make A Plan, Get Prepared

Once I’ve set my goals for the quarter I then create an action plan to actually get me in front of the people that I need to meet. I have been using this plan for my “Grow my network in the NYC startup community” goal:

  1. Attend 2-3 Meetups each month.
  2. Connect with 5 new people at any Meetup or event I go to.
  3. Have coffee with one new person from the NYC startup community each week.

As part of my early morning routine, I check the Meetups each day to see if there are any interesting events to go to. There’s also a decent amount of sponsored parties by larger tech companies that serve as great networking events, like the recent customer party that Mixpanel held in Tribeca. There are lots of articles and tips on how to network effectively at these types of events, and one of my personal favorites is to put a second nametag on (when they let you write your own on those “Hi, my name is” ones). I put the second one underneath the first and usually write “Ask me about PM jobs” or “I like bacon”, as they usually elicit a more direct opening and give the other person a reason to come over.

#1 and #2 are really in service of #3, helping me get those individual “purple” meetings setup. I prepare for an individual networking meeting (usually at coffee at Ground Support Cafe, love those almond milk lattes) by thinking about the following and writing them down in LinkedIn on that person’s profile (in the Notes tab):

  • What’s an interesting news event, blog, or other fact that’s relevant to that person?
  • What do I hope to get from this person?
  • What can I offer them in return?
  • Is there anyone I know who would make sense to introduce to this person?

3. Be Diligent, Follow-up 

I’ve gone through all of this trouble to find, setup and prepare for these great conversations with new and interesting people – but what’s the point of doing it if you don’t follow-up?! I believe that following-up is one of the most crucial parts of any effective networking strategy, and it takes dedication and a system to do so well. I use LinkedIn as my personal CRM system, so after every networking meeting I write down the following either immediately (if possible) or that evening into that person’s LinkedIn profile:

  • Where we met
  • What we talked about
  • What I said I would give/send/share with them
  • What they said they would give/send/share with me
  • If and when we’re meeting up next (set a reminder)
  • Tag them with the month I met them (how I calculated 142 people last month)

After I write all that down I then send them an email following up and thanking them. Boomerang lets me schedule that message to return later.

Lastly, in order not to let my new contacts go cold, I spend time every Monday morning reviewing the connections I made that month and looking for opportunities to help them. This could be an introduction to a colleague or friend, sharing a cool article that’s relevant to them, or asking how an event went that they told me was coming up. Sometimes I don’t have anything to share with a particular connection and that’s okay – I try to be as genuine as possible and only reach out when I think it’s worth it. If you use the Reminders feature in LinkedIn this is super easy since you’ll get an email each morning with a summary of your tasks.

This is just what works for me. The methods and tools that I use in service of my networking goals are just that: methods and tools. Effective networking is really about the goals: if you have good goals, you can use any smattering of tools from my list or others to help accomplish them.

I’d love to hear what tips, tricks, and tools you all use to network effectively. And if you want to meet for an almond milk latter, hit me up!



How I Actually Get Work Done At Work

It’s here.

One of those miraculous days where you only have a few meetings, no travel, and there are some open spots on your calendar. Incredible! You can almost feel the productivity you’ll achieve during those open blocks of time: writing that PRD, reviewing that crazy long marketing deck, or finally taking that one-hour training course you’ve been pushing off for two months. You settle into that first open spot and get ready to rock.

But then the inevitable happens.

Your new email notification dings. You switch to Gmail to check it and, what the hell, while you’re there you’ll answer two more real quick. You see Skype bouncing in the doc, so you check it to see who you hit you up. A quick pit stop to check Facebook and Twitter, and before you know it’s 33 minutes later, you’re four articles into a click hole on Buzzfeed learning useless but hysterical facts about falconry*, and the open hour on your calendar just lost 50% of it’s potential productivity. You might as well write off the rest of the hour if you work in an open office or co-working space, since you’ll inevitably be asked a question from a colleague that turns into an impromptu meeting. You turn back to you computer and realize you’ll have to finish whatever you were working on at 8pm that night when you get home.

What the hell happened?

In the words of the infinitely-wise Sir Arnold Schwarzenegger, “You lack discipline!”** It’s not your fault; our entire digital condition is designed to alert us in real-time about almost everything, making it so we can barely keep focused on a single task, project, or document. For a while I thought I could pull off multi-tasking like a boss but then realized that I definitely couldn’t (and science says neither can most people).

A few weeks back I shared a post about why I wake up at 4:22am. Through the use of a few goals and a basic structure for my morning time, I made it easier to be more disciplined about how I spend that time – so I don’t get up early and just waste it browsing Twitter. I use the same concepts planning my day that I do in my morning routine: set some goals, block off the time, and setup my tools to help me be productive. Using these concepts I feel like I can (usually) get work done, at work, and not feel like I wasted too much time being randomized.

I firmly believe that you need to allocate the appropriate time to every task or else you’ll never get them any of them done during the day. I also believe that you can’t let notifications define how you spend your time. So, to start, here are my tactical goals for each workday:

  1. Output high-quality deliverables (can be written and verbal)
  2. Support my team (employees and co-workers)
  3. Support my management
  4. Learn something new

How I structure my day


7:30am – 8:00am :: Triage and Prep
While eating breakfast at home I read through my inbox, scanning for emails requiring significant work and creating tasks for them in Asana. If the email needs long response I will Boomerang it for 9:30am. If it’s quick, I shoot off an answer. This is the basic “Getting Things Done” methodology that I’ve followed for years. The last step is crucial: for everything in Asana that is due today, I make sure it is has the appropriate time blocked off on my calendar – as an actual appointment.

9:30am – 10:00am :: Email
All of the emails that need a thoughtful response but no other work go into this time.

10:00am – 12:00pm :: PWT (Personal Work Time)
I keep the mornings blocked off to crank out large deliverables, like PRDs, contracts, or competitive reviews. During PWT I “go dark” (I’m a spy movie junkie) by eliminating all notifications. More on this later.

12:00pm – 12:45pm :: Lunch
I try as hard as I can to eat lunch away from my desk and with the team. With the amount of meetings I have this is often the best time during the day to catch up with the team, chat socially, and hopefully laugh a bit at some bad geek jokes.

12:45pm – 1:00pm :: Break
I hate going right back to work after I eat, so if it’s not terrible outside I will go take a lap or two around the block. I usually leave my phone in the office and try to do nothing but soak up a little of the city, clear my head, and get ready for the afternoon.

1:30pm – 2:00pm :: Work Email, Skype, Personal Email
Quick check on work email following the same methodology from the morning spot. I think take the remaining time to check my personal email and various social network accounts.

2:00pm – 5:00pm :: Meetings
This is where I focus on supporting my team and my management. I put all of my 1:1’s with my directs into this time period (once a week), plus any brainstorming or sync up meetings with our various teams and offices.

5:00pm – 6:00pm :: PWT
I usually get a spurt of creative energy later in the day, so I keep a PWT blocked off during this hour to crank through more meaty tasks from Asana. If I don’t have the creative energy that day I use this time to do a bunch of smaller tasks that have queued up in Asana (checking in with customers, investors, etc.).

6:00pm – 6:30pm :: Learning
I use this time to review internal wiki articles, trainings, or other work-related information that I want to read and review.

6:30pm – 7:00pm :: Email and Cleanup
A last pass through emails, creating Asana tasks and moving unfinished time blocks around the next few days.

This doesn’t hold true for every single day given that meetings, travel, and other natural causes can introduce unavoidable change, but I keep to it about 90% of the month. The change that most often happens is I have to slide stuff around during the day to accommodate last-minute meetings. The key here is to be disciplined but flexible. Just because you can’t accomplish something in the time you originally scheduled doesn’t mean that you just hope you’ll find the time later: grab the blocked off time and move it to a new spot where you know you can get it done.

How I setup my machine to get work done

In my “What I Use 2015” post I covered a few of the awesome tools and apps that help me be productive. Here’s a few setup-style tricks and hacks that I use to help me stay focused, especially during PWT.

I use color coding as though my life depended on it. I find that it helps to make my calendar glance-able, and also let’s me visually audit my time to see if I’m spending it in the right places. I use colors for 1:1’s, working sessions, etc., but the most important are Red for Customer Interaction and Blue for PWT.

Multiple Chrome users
I have three user accounts on Chrome on my work laptop: Work, Personal, and Demo. We can ignore Demo since it is for demo’ing our product. In Work, I have all of my work accounts for ThinkingPhones, my Gmail, JIRA, and other accounts are all logged in here. I do not have Facebook or Twitter logged in to this user. In Personal I have, well, all my personal stuff like email, Twitter, FB, etc. I do not have my work stuff logged in there. This makes it so that when I’m cranking on work tasks in the Work persona I won’t easily open a Facebook tab and get lost in the feed.

Multiple Mac desktops
I have multiple Mac desktops setup for, you guessed it, Work, Personal, Demo, and an extra one for Tools. On Work is my Chrome persona for Work, Personal gets the Personal persona, etc. Tools contains our VPN client and terminal windows that I don’t want taking up space in the Work desktop. I have also setup certain programs so their windows open on certain desktops, so iMessage, Spotify, etc. all open on Personal while Evernote and Skype open on Work. This means that I have to make a fairly conscious effort to switch desktops just to check Facebook, Twitter, or iMessage. It sounds annoying to deal with but this has been the single biggest productivity hack I’ve had since the creation of MEATS (my version of GTD).

For all group chats, I turn off notifications and set it to alert me only if my name is mentioned.

Chrome notifications
I turn off all notifications for Gmail’s inboxes.

Whenever I’m in PWT, I flip the Mac Control Panel setting to ‘Do Not Disturb’. I will usually turn it off afterwards, but sometimes I like the quiet and I leave it off for the rest of the day. 🙂

Mac Clock
I set the system clock to announce the time at the top of every hour. I find it a helpful metronome to make sure I haven’t drifted focus, and also to stop and take a break for a minute to shake my legs out and stretch.

For You

Much like with my 4:22am morning routine, this style of working is definitely not for everyone and you can (and should!) come up with the hacks, tweaks, and structure unique to you that will make your days more productive. I’d love to hear any thoughts, feedback, or tricks you have in the comments, thanks!


*As an aside, falconry is pretty legit (link) and someday I’d love to try it.
** Bonus points if you know what movie that’s from.

Why I Wake Up at 4:22am


I was having lunch with some co-workers last week and the topic of morning routines came up. Everyone was sharing what time they woke up, how much they liked or hated it, and the things they did immediately after their feet hit the floor. The conversation turned to me with the question of “Someone told me you get up super early, is that true?”

I’m usually hesitant to tell people what time I wake up in the morning. Sharing the time usually causes whomever I’m speaking with to say something like – emphasis usually theirs – “Seriously? WHY WOULD YOU GET UP THAT EARLY?”

That happened last week. When I told my coworkers that I voluntarily wake up at 4:22am every weekday they looked at me like I was crazy. They shared that familiar sentiment of shock and curiosity, colored with the appropriate observation of “WHY!? We don’t have to be at work until 9:15am.”

Let me explain.

Mr. Wizard

I’ve been a morning person since I was a little kid. As a young nerd I would stay up past midnight every night reading my Hardy Boys novels or writing programs in BASIC on my Apple IIGS (I really miss that computer). In the mornings, my parents would come downstairs when they woke up and often find me sitting by myself at 5:30am in the kitchen, eating Captain Crunch and watching back-to-back episodes of Mr. Wizard before getting ready for school.

There are numerous articles and guides that support the idea that mornings are a time when you’re more creative, energized and productive. The Journal of Applied Psychology even has a study that indicates a strong positive correlation between proactive people and morning people:

“Morning people were more proactive than evening types, and people with small differences in rise time between weekdays and free days were also more proactive persons. Sleep length (on weekdays and on free days) and total time spent in weekend oversleep did not show any relationship with proactivity. These results suggest that morning people are more proactive than are evening types.”

Before I share more, let me say that I do not believe that people who wake up at 8am (like my wife) are more lazy than others, or that people who need more sleep are some form of productivity laggards. The same study I shared above also highlights how differences in circadian rhythms, metabolism, and other individual factors strongly influence the amount of sleep you need and what time you need to wake up. Sleep length and times, like nutrition and many other things about our bodies, is inherently different across each of us and requires personal experimentation to maximize it.

I do believe that even if you’re not a ‘morning person’ in the traditional sense you can hack the early part of your day to make it more productive.

Being Principled

Like my email triage system and many other personal productivity hacks, I’ve spent a non-trivial amount of time ‘tuning’ my morning routine. I don’t want to get up early and waste the time reading Twitter and Instagram (which would be super easy), so I designed my mornings around these principles:

  1. Get chores out of the way
    I don’t get home until late and I hate coming home to chores (like taking care of the cats).
  2. Get my head on straight
    Plan my day, get my calendar in my head, and know what I’m doing that night.
  3. Get smarter
    Spend undistracted time learning new things. Get my tech news fix and re-share content.
  4. Get healthy
    Exercise and eat some good food.

The times below represent the goal state for how I want to spend my mornings. I think I do it with about 90% consistency. I believe that part of having a good morning routine is listening to your body and knowing when it’s telling you things like “Hey, you’re sick. You need to sleep in today.”, or the lovely “Yo dude, that fourth scotch last night was one too many. Take an Advil and go back to bed.”

The Routine

4:22am – Alarm goes off.

I set if for 4:22am because I believe that waking on the quarter or half hour makes it easy to say “I’ll just sleep for another 15 (or 30) min.” Sleeping an extra eight minutes feels less useful to me and incentivizes me to get up. I take those next eight minutes to actually wake myself up, trying to do it slow and with some degree of mindfullness. I sit up, clear my head, throw some sweats on, and put my contacts in.

4:30am – Chore duties.

I feed the cats, clean their water bowls, scoop litter, etc. We have three cats so this actually takes a few minutes. I’ll brew some coffee in parallel and also fill a giant bottle of water to drink before class. I run the laundry (I wash and dry, Amy folds), and do a little light vacuuming (with a quiet dust vac – I save the Dyson for weekends).

4:40am – Learn.

I’m trying to re-learn Italian this year, so I spend 10min every morning using Duolingo to practice different lessons. I found that it wakes my brain up and gets my Duolingo score up for the day. I then try to practice another 10min sometime during the day.

4:50am – Read.

I spend about 15min reading tech news sites. I like to read articles on their actual sites so I use a Chrome bookmark folder called “Daily Industry Review” to auto-open these sites and then click through them. I try to read 1-2 articles per site and will use Hootsuite to schedule them into my Twitter and LinkedIn feeds. Long articles get sent to Pocket for reading on the train.

5:05am – House logistics

I use this time to update our budget, take care of our rental properties, and deal with any household logistics that I need to via email. This is mostly managing our budget in the excellent YouNeedABudget software, emailing tenants about any issues, and reviewing notes from homeowners meetings.

5:15am – Plan my day

I spend the last 10min of this part of the morning reviewing my calendar for the day. I move personal and work appointments around as needed and generally get my head around where I’m going to be and who I’m going to be meeting with.

5:25am – Get to the gym

Get ready for the gym and bike to Crossfit. I usually get there about 15min early to stretch and warmup.

6:00am – Workout / Blog

I workout at Crossfit South Brooklyn on Mondays, Wednesdays, and Thursdays during the week, and both Saturday and Sunday on the weekend. Tuesdays and Fridays are rest days in our gym’s Crossfit programming, and on those days I use this hour to work on my blog.

Back when I first joined Microsoft I was single and had no after-work responsibilities. So I used to go to the gym after work but then wouldn’t get home until 11pm, all awake and energized from exercising. No bueno if you’re trying to get quality sleep (more on this later in the post). After a few months of dating Amy she asked me to not spend two hours per night at the gym instead of hanging out with her. A valid request, and my change to morning workouts happened pretty shortly thereafter. I quickly found I loved getting my workout in during the morning, a sentiment that has only gotten stronger since switching to Crossfit several years ago. It makes me feel energized, and I don’t have that nagging feeling of “damn it I have to go to the gym tonight” throughout the day.

7:15am – Cook, Eat, Triage

After I bike home from the gym I cook a quick breakfast for Amy and I. I’m usually starving since I work out fasted and will make (for myself) a four-egg scramble with bacon, sausage, and veggies, usually with yogurt and blueberries on the side. Yum. While I eat breakfast I take my first look at my work email, reviewing urgent threads and seeing what came in overnight. I keep Inbox Zero so anything in there is either new from the last 12 hours or returned by Boomerang.

8:30am – Head to work

Leave for work. I *love* the R train.

9:15am – Daily standup

Arrive at work for the daily scrum standup. Try to seize the day.

Small Goals, Big Results

As I mentioned earlier, this routine represents my ideal morning and I think I’m able to do it without about 90% consistency. The 10% is from things like traveling, being sick, having gone out the night before or having stayed up super late working. The times and structure for how I accomplish these task has come over time. A big part of the evolution has been setting small goals that work towards a bigger one. Many years ago I was waking up at 5am but I wanted to try waking up earlier. I knew I’d like an extra 30min in the morning, but that’s a big jump and also has a lot of impact on your evening. So I started small: my goal was waking up at 4:45am twice a week, then after a few weeks it became 4:30am, then after a few weeks I spread that out to all five weekdays. More recently that has worked with tasks like Duolingo, and even finding the optimal time to leave the house for the subway.

Count All The Sheep

If you’re still reading this (sorry it’s so long), you’re likely wondering what time I go to sleep since I wake up at 4:22 in the morning. When I was a kid doing the Captain Crunch + Mr. Wizard thing in the AM I was sleeping between four to five hours a night. My father is the same way and we’ve both maintained about five hours of sleep per night throughout our lives. I’ve never been tested but I’m fairly sure I have some variant of the ‘less sleep’ gene.

My goal for the past few years has been to keep improving the quality of the sleep I get by making small hacks and tweaks wherever possible. There’s a lot of good research and plenty of articles that describe how it doesn’t matter how much sleep you need – whether you’re an 8hr person or a 3hr person – it’s the quality that makes such a big difference and enables you to be more productive in the morning and the rest of the day. Unless I’m working late or am going out with friends, I’ll try to get in bed at 11pm on weeknights. Here are some of the hacks I do to get try and keep my sleep quality high:

  • No coffee after 3pm during the day. I’m uber sensitive to caffeine and only need my two cups in the morning.
  • No naps during the day.
  • I try to avoid using my computer or iPad for the 30min before I get into bed to reduce the amount of blue light pulverizing my brain. I have F.Lux running on all my devices to help with winding down when I need to work late.
  • I try not to eat my dinner right before bed.
  • I have a tablespoon of almond butter right before bed to help balance out my blood sugars.
  • I drink one full glass of water.
  • I spend about 15min reading on my Kindle Paperwhite after getting in bed.
  • I’ve found that using a sleep mask helps me a lot. A great side effect is that I’m now conditioned such that when I need to sleep in random places (redeye flights, trains, etc.), I pop the sleep mask on and literally start to get tired. #pavlov

The Reason

The best part about having a productive morning? When I leave work I feel like there’s nothing left for me to do except drink a glass of scotch, hang out with my wife and friends, or binge-watch House of Cards.

What’s your morning routine like?

* picture at the top from

Eat Your Dogfood


“Employees should use the products and services produced by the companies that employ them. They should be emphatic fans of their company’s products. Nothing less.”

— “How to Get People to Eat Dog Food” by Ethan Mayers at AlleyWatch.

I remember when I first heard the question “Are you dogfooding?” shortly after arriving at Microsoft in 2004. I was puzzled for a second about why anyone would not use their own company’s products, especially when they were on the product team that was building them.

Fast forward a few months to the mid-point of the Outlook and Exchange 2007 release. Our dogfood email environment would periodically go completely down for days at a time and we would resort to using IMs and our bug reporting system to exchange important messages. I remember that some of our execs were not in the dogfood environment, but when they heard about the issues we were having they asked to be moved in their with us. They wanted to see for themselves what was going on and to give us a little pressure by having their dogfooding right next to us. Want a quick way to get your day-to-day product stability in shape? Inject a few executives and put their real email on the line and you’ll get blunt feedback, ‘fo sure.

My point here is not that we were in terrible shape in early Office 2007 engineering (we weren’t), nor that we weren’t dogfooding (we all were), or that execs are the best way to do Q/A (they’re not). My point is that as a product manager it’s easy to get stuck staring at the trees and to forget about the forest when working on a specific feature in a larger product. It’s something that can happen more frequently as startup teams get bigger and product managers get more specialized.

In another example from that team, I remember being heads down working on a specific and critical issue in Instant Search in Outlook (one of my features), and I assumed that someone else was seeing the reliability issues I was having with sending email in this specific configuration. I remember bringing up one of those reliability issues to the team that owned Mail Transport, and they determined that it was the specific way that I setup Outlook that was causing the issue (it was having multiple POP accounts loaded into a profile while searching across profiles), and no one else on the team was seeing it because it was setup- and timing-related. It was a critical bug because many of our customers would eventually have a setup similar to mine and therefore could have been susceptible to the issue once we rolled out the new feature.

As teams get bigger and more specialized it’s critically important that product managers dogfood their specific feature or product. It’s equally important, if not more so, to make sure you are always dogfooding end-to-end experiences outside of your feature ownership and across the entire breadth of products you build. You should also look for unique ways to get a fresh perspective while dogfooding. For example, we found that by adding the execs in at a time of difficult product stability during Outlook 2007 development, we were able to inject some “new eyes” into our day-to-day work and get some great objective feedback. This also helped us get dogfood coverage on features like Delegate Access, a setup that only happens when someone else manages your inbox and calendar in Outlook (a setup very unique to VP-level and higher users). In another case, we asked the entire product team to unplug their mouse for an hour to try and use Outlook via the keyboard only, helping us find a bunch of good bugs in our accessibility code.

Here on the Contactive team at ThinkingPhones, as our products get more complex and our team grows, we continue to dogfood every day and constantly come up with new ways to get those fresh perspectives. One of our favorites are weekly team-wide dogfood bashes to help get fresh eyes on new areas of our code. One of our product managers puts up a whiteboard, cranks the music (usually 80’s workout montages from Spotify), and everyone writes the bugs they find up on the board. We sometimes award “most interesting bug” and other fun prizes. You’d be amazed by what you can find with that kind of intense focus. We also have a “Bugs” email alias that gets traffic at all hours of the day, as we have all adopted the habit of sending screenshots and bug reports the minute we see them. We find that these types of efforts help increase the focus of the whole team on the quality of our products.

Our goal at ThinkingPhones is to be proud of our products and deliver amazing experiences to our customers. We believe pride comes from quality, and quality comes from eating your own dogfood.

Yum.  🙂

Blind Spots, Transitions, & A Book Review: “The First 90 Days”

first 90 days book cover

A few years ago I switched teams inside of Microsoft and joined the Office 365 group inside of the Exchange team. I was jumping in mid-release and as a manager, so I had to get up to speed on my own responsibilities and that of my team. If you know me you’ll understand when I say that my first day was about creating lots of lists: who to talk to on my new team, documents to read, customers to talk to, etc. I love lists, and I love tasks. Since I was joining a big team with peers who had several directs themselves, I put together a big complicated list that mapped each of the PM’s in our larger team to their project and their manager. I found this helpful because I always like to ‘see the big picture’ visually. I shared it with my peers and my manager and asked them to update it since I had made guesses about some of the projects, telling them we could use it as a reference across the team. I didn’t get a response after a week and pinged them again. No response. Huh.

A few weeks later during a peer feedback session I got a response from a colleague that has stuck with me clearly ever since then: “I really enjoy working with Michael, but when he first joined the team he immediately tried to get us to use this complicated way of keeping track of our directs and their ownerships. I didn’t have a need for it and got annoyed that he kept pushing for it.”

Whoa. That wasn’t me. I wasn’t the guy who pissed people off while I was trying to help them. Or was I? What I realized was that sometimes my personal organization processes and styles need to be just that: personal. The point? Transitions are super tough and involve a million little things changing at once, and it’s easy to forgot areas of your personality that are already weaknesses when dealing with larger parts of the transition.

Now about this book. I feel the same way about self-help and self-training books that I do about the types of in-person training I’ve attended while working for big corporations: if I feel like at least 70% of the time I spent attending/reading was valuable then it wasn’t a total waste of time. That may be a cynical way to think about it, sure, but I’ve been burned in the past by overly-drawn three day training sessions where the entire time you’re wondering “WHAT IS GOING ON?!”, and then there have been rock-star ones like “Situational Leadership” that I still discuss and use almost every day in my job.

“The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter, Updated and Expanded” easily meets my 70% rule for being a great book and I believe can help with transitions in your career.

The first time I read it was when I left Microsoft in Fall 2013 and was on the recommendation of my best friend Vinny Pasceri, a fellow Microsoftie who knows a lot about transitions between startups and big companies. It was immensely helpful while I was making the transition to work at Contactive because of how well it structured the process of feeling like I had 9 million things to learn at once. Most importantly, it hammers home the idea of not making lots of quick, bad decisions because of lack of information that then inhibit your ability (and reputation) to do long-term good in the organization.

I re-read the book this January as we were going through the acquisition process with ThinkingPhones. It was faster the second time around and I was able to skim through parts that weren’t as relevant, but I found it a good refresher of some of those “blind spot” challenges that can be easy to hit in a new transition.

The book has a LOT of frameworks in it, and sometimes I feel like it tries to straddle the line too much between being a step-by-step training manual and a good reference of ways to approach situations. I tend to be very example-driven, so I wished it had more of the mini case studies to support the various frameworks. I stopped trying to fill out the (many) worksheets as I was reading it and instead allocated 30 minutes each week to pick a section and make actions items for myself based on it.

I didn’t find any framework or set of steps that was completely foreign to me. I did, however, find the single most useful outcome of reading the book to be getting way more honest about what my weakness are in times of transition, like trying to force old ways of work into the new one, and forcing me to write them down in order to be mindful of them.

The book is focused on senior-level management positions in large organizations making big transitions, and only really pays passing mention to startups. That’s not a blocker for making this a usable book by almost anyone making a transition in an information worker role, especially one in management, since the frameworks and methodologies are non-specific.

4/5 for me.



Contactive Joins ThinkingPhones


“The Coffee” – Aug 2013

I remember it well. It was the end of August two years ago and I had taken a long weekend to visit my parents in NY. Amy was travelling with her girlfriends, so I had a few days by myself to hang with the fam and visit some friends in the city. After a weekend of BBQ’ing and relaxing at my parents’ house, I spent Monday doing a catch-up tour of sorts in NYC by meeting up with some friends and colleagues in Silicon Alley. I love these kinds of conversations with people in tech; they’re not interviews (I wasn’t actively looking), but they help me stay connected to the startup world and (at the time) to what was happening outside of Seattle in tech.

My last coffee of the day was with an old colleague named Iñaki Berenguer. We met when he was at Microsoft many years ago and had kept in touch periodically over the last few years. We met up at the Pixable offices in SoHo and had a coffee on a very worn (but loved) couch. Iñaki had just sold Pixable, so after a few minutes of catch-up about the acquisition he said “I want to tell you about this new thing we’re building. It’s called Contactive.”

Change is hard. For Amy and I, change like “Move across the country” and “Leave your friends and life and job of over ten years” was something we talked about in our five-to-ten year plans, but never really thought would happen. I hadn’t found the right reason to make the change.

Up until then I had spent my entire career building software to make people more productive. I’ve always been inspired by helping people work better, faster, and ultimately (hopefully) happier. It was awesome to work at Microsoft right out of college; I was 21 years old and got to build experiences into Microsoft Office that were later used by millions of people. Serious nerd-rush. Over the years I became obsessed with bringing social collaboration and productivity into the enterprise, cutting my teeth on partnerships with LinkedIn and Facebook, and was amazed at how big the opportunity space was.

So when Iñaki described what the beta version of Contactive did, and more importantly what he thought it could become, I had one of those ‘eclipse’ moments when you see things align in a super-crazy way:

…an early stage startup
…focusing on social and big data
…in NYC
…with a crazy smart team
…needing a product guy with enterprise software experience

You get the idea. 🙂

Fast forward two months later: Amy and I are living in Brooklyn, I left Microsoft and am now employee #7 at Contactive in NYC. It happened so fast that for the first few weeks I still woke up on Seattle time to go to work. We’ve since settled in and have loved every minute of our new lives here in NYC.

Our mission at Contactive was to make our users as prepared and productive as possible for every conversation they have. Over the last 2+ years, we have worked non-stop to build a strong big data platform, a brilliant team of 20 people, and a solid product with over 1 Million users. Along the way we also launched Klink, our enterprise offering for optimizing communications at large enterprises.

Today, we are excited to announce that we are joining ThinkingPhones, the market leader in Unified Communications as a Service (UCaaS). By joining ThinkingPhones, we can move another step forward in closing the gap between the world of big data and telephone communications, to increase the productivity and efficiency of communications.

Screenshot 2015-02-04 09.16.08

It is an honor and a privilege to join ThinkingPhones. Over the past few weeks I’ve had the chance to get to know Steve, Derek, and the rest of the team at ThinkingPhones. The’ve all been working together for over ten years and have started several successful companies together before ThinkingPhones. It’s clear that they really enjoy working together and have built a supportive and fun place to work. I am also supremely impressed by the agility, passion, and innovation they bring to the space.

I would be remiss not to thank a few folks for supporting me on this journey the last few years. My wife, Amy, for her willingness to uproot our life completely and move to NYC. My parents and family, for their unwavering support and sounding board over the last two years.

Most importantly, I thank my fantastic colleagues here at Klink. We are a family as much as we are a company, and it’s been a pleasure to work and sing terrible karaoke with them.

You can read more about the acquisition here. Thanks!


Screenshot 2015-02-04 10.28.06