Hiking the Annapurna Circuit

My wife and I hiked the Annapurna Circuit in April 2018, and it was one of the best trekking experiences of my life. Each day felt different, there was sheltered accommodation, and the hiking through the largest mountains in the world was truly epic. On the highest day we hit 5,416m (17,760 ft) via the Thorong La Pass. We preferred this trekking experience to Mount Kilimanjaro because it was less of an ‘up and back’ and felt more relaxed.

Here are a few recommendations:

  • Guide/Porter: You don’t really need a guide or a porter but it’s a nice way to support the locals, and is inexpensive. A porter is more useful than a guide. On some of the harder days, carrying a day pack makes the hike a lot easier than carrying all your gear. You can sort this out easily when you arrive into Kathmandu, through your hotel.
  • Gear: Don’t overpack. You can re-use good quality ski gear (here are my tips – make sure to layer) and the packing list is similar for clothing for Kilimanjaro. A good sleeping bag is essential to stay warm on the huts on the way. Pack some blister pads. Use hiking poles.
  • Add on the Ice Lake day hike in Manang: Stay two days in Manang. You can do laundry here and watch movies at the ‘cinema’. The Ice Lanke was a really awesome day, albeit a little challenging (4,600m and about 8 hours long). One of my favourite days of the trip. We were supposed to go to Tilicho lake but the path was closed because of avalanches.
  • Complete the “half circuit” and fly back: Our trek was 15 days, and we started in Besishar and ended in Jomsom, where we flew to Pokhara a little over half through the full circuit. A lot of the research shows the last half of the circuit as a bit of a ‘grind’ with cars on the road adding to a less pleasant, more dusty experience.
  • Hang out in Pokhara after to relax: This is a chill, hippy city in Nepal. We had massages, good food, did some yoga and a few relaxed hikes and boat rides. We also treated ourselves to a nice hotel. It was wonderful to spend 2-3 days here relaxing after the trek.
  • Lodging: Accommodations are all pretty similarly priced in the villages along the way. If you arrive earlier, you’ll get a better pick of the available rooms. We were also able to “shower” (mostly out of a tap or bucket) every few days.
  • Food: Pack some chocolates, or other tasty snacks but know that you’ll have hot meals for lunch and dinner along the way and plenty of places to stop for tea. I’d recommend eating mostly vegetarian, and mostly Dal Bhat.
  • Leisure: Get a local sim card so you can communicate on the trail (no-wifi) and bring your Kindle to read in the evenings. Bring a deck of cards too. The scenery is epic but modern phones can probably suffice, unless you’re an avid photographer.

I also like the Kathmanduo blog which is well written and has a lot of details, but is a little old (2011).

Here are some photos of the trip!

‘Fresh Faced’ early in the trip
K2 In the Background (I think)
Ice Lake Hike

Epic Views Every Day
Vistas
Tea House Life
Little Bridges on the pass
Throng La Base Camp – cold!
Throng La Pass – the highest day
Throng La Day
Last few days of the trek
Unhappy to be on the tiny plane

Productivity Tip – Text Shortcuts

My favourite recent productivity tip is using text replacement which is built into to MacOS natively (System Preferences -> Keyboard -> Text). These rules also sync with iOS so you can use it on the go with your iPhone. It’s native in the operating systems so you can use these shortcuts in whatever program you’re using (iMessage, WhatsApp, Email, Google Docs etc).

I’ve set up about 20 text shortcuts and use them many times a week. I set up the shortcuts to begin with “>” which makes them hard to trigger accidentally and also lets me to use words/phrases that are easy to remember. Some examples:

  • Phone number: >ph
  • Address: >add
  • Intro thank you and to bcc: >intro1
  • Intro nice to meet you: >intro2
  • Schedule a call with me: >schedule with Calendly link

I had Alfred (paid product) for this previously, but it’s a step function worse because it’s not deeply integrated with both MacOS and iOS. The only benefit from Alfred is that it supports Rich Text (formatting) and the ability to add text with links – I now just put links in brackets. I has previously also used canned responses in Gmail but this method is superior.

It does take a little bit of time to set up and get familiar to using the shortcuts but once you get going it’ll save you a ton of time.

Trends Accelerated by Covid-19

Covid-19 has led to significant changes in how we live, work, and interact with each other. In some cases, they have accelerated trends that were already in motion, and in other cases forced changes that we did not anticipate or expect.

In the next few years, I think we will go through a rapid pace of innovation and re-imagination powered by entrepreneurs, and here are a few trends I’m excited about and interested in exploring further.

Distributed Work

The best summary I’ve read on the acceleration of distributed (not in person) work is this one from the CEO of Automattic, Matt Mullenweg where he talks about change happening slowly, and then all at once driven by this catalyst. Automattic has been fully distributed since its inception, and Matt has been a champion of distributed work for years and the benefits of accessing a global talent pool, and working asynchronously.

The #WorkFromAnywhere Podcast series led by the folks at Greylock is also excellent and CEOs of companies like Box, Quora, Okta, Figma and Zapier speak about their transition to working from anywhere.

I’m particular excited about the tooling that will be developed, both in terms of specific software as a service products to drive much better distributed collaboration, but also the underlying plumbing that ties all these tools together.

ECommerce

This article from Ben Evans on the growth of eCommerce is a must read. The UK went from 20% to 30% eCommerce penetration and analysts say that Covid has accelerated the growth of eCommerce by 5 years. This is dramatic, and will change the way may of us purchase, discover new products, and how creators distribute their products.

This also changes the nature of distribution/logistics and the entire supply chain. Companies like Shopify and Amazon have doubled their market cap (adding over $60BN, and $850BN (!!) of value respectively to shareholders since mid March 2020).

Major Cities

The nature of major cities and concentrated urban areas is going to evolve. I wrote about my thoughts on megacities recently here, and I also liked this piece from Fred Wilson about how a reset was much needed in NYC and how the city could evolve into something better. Many of my friends have ‘accelerated’ moving to their ideal living areas and and left places like NYC and London. My wife and I, having just had our first baby, are asking ourselves the same question – is it worth staying in NYC if we don’t intend to stay longer term? The pandemic has forced a conversation we likely would not have had for a few years.

Flexible Work

I believe that the best creators and experts are no longer going to need a ‘normal job’ and will be able to work flexibly and monetize their unique skills talents much better than before, and this will be socially acceptable and maybe even celebrated. I like the writing from Li Jin (Atelier Ventures) about the Passion Economy and Unbundling of Work from Employment (which I also opined on here).

Startups will create innovative tools, and platforms to help craftspeople to discover projects, collaborators and showcase their work (e.g. Contra). Much of the benefit that we get from a ‘normal job’ (e.g. competitive healthcare insurance plans, retirement accounts, etc) will also be available to creators through saas products.

Building Relationships

As humans, we yearn to build new relationships and deepen relationships with folks that we already know. Traditionally we’ve built these relationships in person with repeated interactions and meaningful collaboration on projects. Being forced into lockdown has forced us to explore alternatives.

I’ve personally been experimenting with platforms like Enrich (curated network of similar executives), Fractal (1×1 matching with other product people), Village Global Events (with startup founders and investors), and am starting the On Deck Angel Fellowship soon. These are all digital communities with fairly niche audiences, which I think will become more common.

I’m hoping that these will lead to meaningful relationships and collaboration and also improve the chance for serendipity despite not being able to spend time with folks physically. I’m excited that these platforms could open up the possibility of meeting interesting people all over the world, and not just limited to my place of residence.

I’m not sure how this will play out with larger conferences, where most of the value is in relationship building and improving the probability of serendipitous connections often through extended hang out time (often over meals and drinks). I expect that recreating much of the value will be possible, but will require some first principles thinking.

In my own recent experience, I wrote about how the funeral for my grandfather was actually much more inclusive and rich because it was virtual and allowed for more people to attend that were close to him (like his sisters).

Personalized Services

Folks who provide coaching, classes or specialized services are all going through a similar, accelerated transition.

Companies like Peloton have successfully taken spin classes and made them virtual, allowing both synchronous and asynchronous (on demand) classes with world class instructors. Each class can now be attended by step function more people which greatly improves the ROI for each class.

Experts providing specialized, personalized services like physiotherapy, child psychology, lactation consulting can all increase their addressable customer base and people who are in need of very specific services can access a larger pool of specialists which is better for both groups. They both need tools to make it easier to discover each other, and improve the experience of booking and transacting (e.g. Ribbon Experiences).

Digitial Payments and Services

Digital payments and digital services (e.g. digital hr, or payroll) to help businesses transact with their customers and run their teams will also see more new users, and increased adoption. I think these products will be ultimately sticky even after Covid-19 because they function better both in person and remotely, and allow for more flexible customer and employee interactions. In my personal investments in these areas I’ve seen increased volumes and good retention through the pandemic.


These are just a few areas where I’ve personally observed changes in my own life or with folks close to me, and I’m excited to learn more and closely track how these trends evolve.

Hiring Product Managers at Scale

In this post, I summarize a process that I recommend for hiring product managers at a midsize or growth company, adapted for a distributed hiring environment (most applicable to a company that will hire multiple product managers).

I’ve hired and trained over 40 product managers over the course of my career, and this draws on my experience as a product hiring manager and team lead.

Internal buy in and scope of role

When hiring product managers (PMs) at a mid size company the most important thing is to have internal support from the executives and the design and engineering partners. There should be a strong desire to hire PMs to help build better products in a better way and to bring in more structure and systems to the product development process.

Once there is buy-in from these stakeholders, organize the teams into sensible working groups (e.g. by user journey such as onboarding/growth or by key metrics such as conversion/retention or by product line).

I prefer a matrix structure (although has tradeoffs) where PMs ‘own’ each of these areas in partnership with a design and engineering lead (with around 5-10 engineers per PM, depending on the project). I also suggest that engineers and designers report into their own functional leads and PMs direct the scope and priorities of the projects.

Hiring process

It’s essential to have a clear hiring process and system both for the sake of your internal team and for the candidates. Most companies are incredibly disorganized about hiring, but a little bit of work can save a lot of time in the future, especially when hiring many folks for the same role.

Internal Team 

  • Recruiter: There should be a consistent point of contact for the candidate during their application process – ideally a recruiter. The recruiter communicates with the candidate, lays out the hiring process clearly, and moves them through the process. They act as a liaison between the hiring manager(s) and the candidate. They often do the initial resume screens and have an essential input into hiring because they get to know the candidate so well. 
  • Hiring Manager: The hiring manager is the person that is hiring for the role. They are the person who ultimately makes the decision to recommend the candidate as a ‘hire’ or ’no-hire’. This is typically a senior product leader.
  • Interviewers: Each interviewer should have a clear set of criteria that they use to evaluate the candidate. The interviewers should be excellent at the functional areas that they are evaluating candidates and hold the quality standard for the organization. The best people should be involved in late-stage interviews and this should be a core part of their job description.

Hiring Process

  • Resume screen: Internal and external candidates should submit a Resume / LinkedIn profile which should be screened upfront (recruiter + hiring manager). Candidates who pass this phase should move to a conversation with the recruiter, followed by the hiring manager.
  • Interviews: Interviews should consist of a standard set of, very well calibrated questions that can be asked by a variety of interviewers representing the different development functions (e.g. design, engineering, product, marketing). A structured hiring guide improves consistency and calibration, and can reduce bias from the hiring process
  • Central Tool/ATS: Interview feedback should be stored in a central place/tool (e.g. Greenhouse or Lever) and each interviewer’s feedback captured clearly (with a hiring recommendation). This allows us to both evaluate interviewers and the candidates – e.g. some interviewers bias towards higher or lower scores.
  • Written Exercise: If you are hiring in a distributed environment, try to find candidates with strong communication skills (particularly written skills) and clarity of thought. All candidates should complete a written exercise as part of their recruitment process which could include:
    • Break down a product you love – what you like, what you don’t like, how you would make it better (1 page)?
    • What is your favorite technological shift and why?
    • Write a ‘product spec’ to address a specific problem that the company has (better if it is a real problem).
  • Trial: If possible, ask the candidate if they would be open to a two-way trial (which is compensated) where they try and solve a real problem and collaborate with an internal team. This is time consuming (20-40hrs for the candidate, 5-10 hours internally) so very few candidates should go through this process if you decide to incorporate trials. You may filter out some good candidates because of the time commitment, but candidates who join are more likely to be successful.
  • References: I think that final candidates should be referenced checked by the hiring manager, especially if there are open questions. Backchannel references are the best (but avoid people at their current company) otherwise, ask the candidate for references. Here are some questions that I like:
    • How do you know the person? (gauge depth of relationship)
    • What are their strengths?
    • What are their areas for development?
    • What percentile would you put them in relative to similar folks in their position?
    • Would you hire them again?
  • Decision: For borderline candidates, the panel of interviewers should have a sync or async discussion – e.g. a private recruiting slack channel for hiring. The hiring manager is ultimately the decision maker. From start to finish, try and keep this process fast (e.g. under one month, and track the throughput).

Candidate experience

Candidates should have a great experience, understand how they are being evaluated and have consistent clear communication through the process.

  • Hiring Criteria: Candidates should understand the criteria by which they are being evaluated and the steps in your hiring process – this should be a templated email or a public blog post that you can send to product candidates.
  • Point of Contact: Candidates should have a clear point of contact (ideally the recruiter), to ask any questions about timelines and next steps.
  • Acceleration: If a candidate performs very well in early interviews or comes in through a trusted referral, they should be bumped up to the top of the queue or potentially skip steps so you don’t lose great people because of slow process.

How to Assess

When hiring, it’s important to be explicit about the skills you are looking for, and get a sense for where candidates are truly exceptional.

Here are the dimensions that I think you should use to assess candidates in the interview process:

  • Analytical Ability: AB Testing, Interpreting metrics, Data-informed decision making.
  • Product Judgment: System design, UX design to solve user / business problems.
  • Leadership: Inspiration, Influence, Empathy, Communication.
  • Execution: Prioritization, Getting things done when you say you will.
  • Technical Ability: Earn trust and respect from engineers as partners. Some roles will have a higher technical bar than others.

Each person on the interview team (3-5 people) should be responsible for evaluating the candidate along a subset of the interview criteria to create a balanced view. Ideally interviewers would ask the same questions to each candidate to calibrate their answers. I suggest that each interviewer test at least 2 dimensions of the list.

I suggest looking for candidates with an exceptional ‘A’ level strength, particularly in harder to learn skills like analytical ability and product judgement. I much prefer ABC candidates over BBB candidates because it’s possible to design complementary teams with AAA skills in aggregate.

Candidates should also demonstrate strong domain knowledge, and passion for the product, company and the customer. If they have prepared, it goes a long way (and it’s surprising how many candidates are ill prepared). If a candidate teaches me something new, or helps me challenge my own assumptions, that is wonderful. 


Appendix: Other resources

Google Criteria

  • Product Design: User experience, Design driven problem solving.
  • Analytical ability: Fluency with numbers, Using data to drive product decisions, dashboard design.
  • Technical ability: Understand technology and fundamental computer science principles.
  • Strategy: Go to market, Competitive analysis.
  • Culture: Googliness, Kindness, Leadership, Empathy.

Facebook Criteria

  • Leadership and Drive: Influence, Self-starting, Motivation, Persistence.
  • Execution: Goals, Metrics, Prioritization. Understand, Identify, Execute.
  • Product Sense: A design exercise to solve a specific user or business problem.
  • Engineering fit: Do engineers want to work with you?

Product Manager Articles

Here are a few articles about product management as an appendix, in case they are useful.

Hiring your First Product Manager

When you’re running a small startup, you may ask yourself when to hire your first product manager and what you should look for in the candidate. This is a question I get from founders fairly often.

Startup founders in technology companies usually are great at least one of the following things; making stuff and selling stuff. Few individual founders are great at both, but most successful founding teams are excellent at both.

In the early stages of your startup, when you are trying to find product-market fit, you do not need a product manager. As founders (at least one of) you should be the product people at the company – obsess about the product, spend time with customers, drive the product roadmap, etc.

When you have found product/market fit and you are starting to scale, is when you should hire your first product manager. This person can run the day to day product development and allow you (as the founder) to step back and focus on fundraising, product strategy, hiring, and important partnerships. This person should bring you significant leverage. 

Many founders think they need a ‘Head of Product’ first – I don’t think that is right. I would not hire a super experienced product person who expects high compensation, owning the entire product vision and strategy or brings in ‘this is how we do things’ from their background.

Instead, I would look for an early/mid stage in their career, who is a strong executor and is high potential and can grow with the company. This person should be passionate about your product, users and you should be excited about mentoring and working closely with them (as founder/CEO). 

If this person ends up doing a great job at the execution, they can take on more product strategy from you as you build mutual trust and respect. If they are not able to scale in this role, you can bring in more experienced folks to lead the organization. Replacing a product manager is much easier and less expensive than a head of product.

My Home Office Set Up

My current home office set up is a little bit makeshift as we are living with our in-laws (temporarily). I figure that a lot of people would be in a similar situation and thought it would be worth documenting and sharing as I’ve already helped a few friends and family members with their home office.

I’ll share the details of my set up and then summarize some practical tips that apply to most people.

Home office Front View
Home Office Side View

My Set Up

My set up is optimized for using a Macbook Pro 13 inch as the computer, and so this will only really apply to mac users.

  • Monitor: In my opinon, this is the most important part of your setup. I have an expensive LG 5k monitor with a built in HD camera ($1,300). If I had a less generous monitor budget from work, I’d get a 4K monitor, like the Dell one ($500) I recommend below, with an additional HD camera clipped to the top.
  • Keyboard: I use a mechanical keyboard as I like the action, and it makes me feel like more of an old school gamer. I use the Keychron K2 Wireless Keyboard ($80) with a red switch which is a bit quieter than the blue switch (although the louder ones are more satisfying).
  • Mouse: I use the Logitech MX Master 3 wireless mouse ($100). It’s super comfortable, has lots of customizations and is way superior in ever way to the Apple mice in my opinion.
  • Headphones: A great pair of headphones is essential. I use Bose QC 35 II noise cancelling bluetooth headphones ($280) just because I’ve had them for 5 years. They are really comfortable and have great sound, but the microphone sucks so use them with the wired mic if you are not going to get an external mic. If I was to replace them, I’d go with the Sony WH-1000XM3 ($240) which seem to be a one of the better picks in the market right now.
  • Samson G-Track Pro mic: I’d recommend either my Samson G-Track Pro ($130) or the Blue Yeti (Nano, Yeti or X are probably all fine) which are USB condenser mics and easy to set up and use with great audio. Watch out for room echo – if this is an issue, switch to a USB headset mic, like a recommend below.
  • Desk mat: I really like having a desktop mat. They are inexpensive and increase the friction for your keyboard and mouse keeping them in place while giving you a nicer surface to rest your hands. I use this Yikda Leather Pad ($14).
  • Stand for monitor: It’s important to have your monitor a t the right height and I like a stand that lets me put my laptop under the monitor to save some desk space. I just picked one from Amazon and ended up with this AboveTEK Stand ($45).
  • Wireless charger: I use this Anker one ($12) which is useful to charge my phone and AirPods without a lot of additional cable clutter. I like just being able to drop my devices on the pad to charge.
  • Desk plant: Plants can apparently reduce stress and improve mood. I got these succulents from Lula’s Garden as a gift and like having them on my desk as they are low maintenance as well.
  • Candle: I love having candles on my desk. I find them soothing and like the smell. I like the Aquiesse candles ($32) as they are both high quality and last a really long time. Highly recommend.

Note: my desk and chair were already in the house, and repurposed for my home office.

Universal Advice

Here are a few of my most practical tips when setting up your home office:

  • Monitor: Get a decent monitor (4k), you can get pretty excellent ones for the Macbook Pros like this 27 inch Dell 4k (~$500) with a USB-C cable that can be used to both charge your computer and be the display/data connection. I bought this for my father in law and think it’s great. This is the thing you stare at all day, so don’t skimp here. Make sure the monitor is positioned high enough so your eyes are in the center of the screen when you sit upright.
  • Video camera: Good quality video helps you seem clearer because you are! The cameras on Macbooks suck, and are 720p, not even HD, so if you do get an external monitor then definitely get a camera that clips to the top of your monitor. I use my fancy camera or the built in camera on my monitor. The one I see most recommended is the Logitech C920, but I’ve not used it myself.
  • Light source: Face a light source with either a lamp on your desk to light your face or a window. If you are by a window, make sure that the sunlight does not hit your face directly as it’s annoying and distracting.
  • Audio: Good audio is so important for distributed work. I did a full write up comparing a bunch of options here. A wired USB headsets with a mic that is a consistent distance from your mouth is the best option for most people. This is one we recommend at Automattic. Here is another audio comparison from Matt, the CEO of Automattic.
  • Chair: I’m still researching the best value chairs (my current one was lying around the house), so don’t have a practical suggestion but you sit in this all day, so get something comfortable and adjustable that allows you to have good posture.

The rest of the stuff is really dealers choice in my opinion, and icing on the cake. For a long time I did not have an external keyboard and mouse and just used my Macbook keyboard (or mouse), which worked really well and was space efficient (see below).

Using the Macbook as a second screen and keyboard

I also use a mirrorless camera (see below) but it’s a bit less frictionless so I don’t use it all the time. I set up the camera above my laptop screen, with the camera above the screen because this keeps my eyes closer to the lens without it looking like I’m very close to the floor. It also helps me focus on the conversation better.

With the mirrorless camera setup

Hope this helps you level up your WFH set up, and let me know if you have any tips for me. Oh. and make sure you have good internet, or none of this really matters 🙂

Evolution of Megacities

I live in New York City, and have been thinking about how I think large, densely populated cities (in developed markets) will evolve after Covid-19. I don’t think the soul of the city will change, and reading Here is New York (by E.B. White) from the 1940’s affirms this, but I do think the city will go through an evolution over the near to medium term.

New York City has gotten more and more expensive which has resulted in it shrinking (net population loss). The growth of the suburbs continues to be good (across the US) particularly from immigrants who tend to have less disposable income and seek better value for money. This podcast episode with Alex Danco and David Perell also is a fun discussion on the subject that is worth checking out if you’re interested in the subject.

The continued rise of eCommerce/delivery, distributed work and autonomous vehicles, are all shifts that are likely going to accelerate changes in megacities (some of which were catalyzed by physical distancing).

Fully distributed or partially distributed is a particularly powerful trend as many technology and finance jobs may no longer require living in places like NYC as a prerequisite but can still pay the same wages.

Here are a few of my predictions:

  • Offices centered around collaboration, not individual contribution: Office in the future will look different. I imagine they will have more meeting space, and more collaboration space versus single person desks designed for individuals. These collaboration spaces will be shared, and only a portion of the company will be in the office on any given day.
  • Less office space, more (and larger) residential spaces: Individual contribution work will happen outside the office, and much of it from home or other flexible work spaces (coffee shops, shared office space). Office space will be repurposed into residential space or other gathering (e.g. bars or restaurants) or ‘multipurpose’ spaces. Homes will be larger to accommodate flexible working spaces or dedicated offices.
  • More young people, more old people and fewer families: Young people love densely populated places, and so do healthy empty nesters. Megacities will have more of them particularly as empty nesters are fitter and healthier for longer. The food, culture and nightlife scene will become even more vibrant.
  • Growth of the suburbs around megacities for families: Families all move outside the city epicenter, where dual-income parents can still easily go to their offices for occasional collaboration sessions (e.g. 1-2 times a week) but spend most of the time working from their home. The quality and comfort of these homes becomes even more important for families. The transport from homes to offices becomes even easier and faster because of driverless cars (5-10 years away).
  • More pedestrianized, car free zones, and even more delivery: Purchase of ‘staples’ happens more and more via delivery vs. in person and ares of the city (e.g. Flatiron) become fully pedestrianized and cycle zones with delivery permitted during certain windows.

I don’t have any real unique insight into this topic, beyond personal interest. I’ve spoken to a number of business owners who are not extending their office lease, and also a number of friends (particularly with families) who are leaving the city for the suburbs.

I would personally not invest in real estate in Manhattan over the next few years until we see how it’s going to shake out. I think that investing in the city suburbs, and in ‘up and coming’ cities with net population growth, growing income/capital and with great culture but lower cost of living is likely still a solid call.

Performance Management

This post will summarize my personal learnings for managing performance in both a distributed and non-distributed environment. I recently hosted a discussion on ‘Remote Performance Management’ with engineering and product leads at other companies (through Enrich) and these were some of the topics we covered.

Performance management in a distributed environment is very similar to working in person, except you need to rely more on measuring actual contribution, and more written communication. 

It can be very draining for a team, and for managers in particular, to deal with performance issues on their teams. If these are not dealt with quickly, they can fester and affect the entire team. It is important to have a clear path to gather data, diagnose and solve for the productivity and for the ‘health’ of your team.

1. GATHER INFORMATION

Start by gathering data to figure out if there are performance issues.

Your Gut: Most of the time, you know if someone is performing well. Trust your gut and use it as the starting point. Write down examples of issues you observe in a document so you can spot repeated patterns. In a distributed environment, it can take longer to calibrate your gut – you can’t ‘feel’ the energy of a person or a team as easily, so you need to rely on the output of teams. The more teams work out in the open (public by default), the easier it is to understand their output.

Team: Ask for feedback from folks who interact with the person closely – peers, direct reports, other functions. This can be more casual or part of a broader discussion if you don’t want to cause ‘alarm’. You can also ask your HR rep to help gather feedback for you as well. 360 degree feedback tools are also really valuable for managers and teammates to give feedback on each other.

Data: Try and figure out objective measures of output – communication metrics (e.g. Slack stats, public posts and comments), projects delivered, GitHub commits can all help paint a picture of productivity. It’s important not to use these metrics as the starting point for performance management – they are simply a useful tool to help validate or invalidate hypotheses. If people feel like they are being ‘watched’ they will not like it, or try to game the system which is not where you want them to focus.

2. DIAGNOSE ISSUE

Once you have established there is a performance issue, the next step is to unpack the why behind the issue.

Capability vs. Effort : I start by trying to understand if there is a capability problem or a motivation problem and use this simple matrix. Folks who are high capability and effort should be rewarded, and folks who are low capability and effort should be transitioned out of the company quickly.

This image has an empty alt attribute; its file name is impact_effort_matrix_brainstorm_-_brainstorm.png

Manager / Team Fit: The individual may just not fit in well with the team culture or have a good rapport with their manager. Once a manager has ‘lost faith’ in someone on their team, it’s very hard to regain faith without a team switch.

Project Fit: The individual may not enjoy or be well suited to the type of work they are doing. This person might have a capability or effort issue, and in most cases this requires a move to a different role or to a different project. 

3. IMPLEMENT CHANGES

Once you’ve diagnosed the issue, the next step is to figure out a path forward. Many new managers simply avoid having these hard conversations because they are awkward and can be difficult.

Communicate clearly: Communicate performance issues clearly with the individual and then lay out a clear path forward with areas for improvement and timelines. This step comes before a formal performance improvement plan (PIP) which is more serious to developmental feedback.

Termination: If you have reached the point of termination, then be clear, direct and kind. Schedule a short in person meeting or video call, and get straight to the point. Often HR is involved in this call, and at some companies they are responsible for this meeting.

Team / Role / Project switch: If the individual is new to the company and has performance issues, and you suspect they are in the wrong role, wrong project or have fit issues with their current manager or team then you should allow one switch to give the person another shot. If the performance issues are persistent, then they should be let go from the company.

Permission to leave: Often, an individual was the right fit for the company or for a role at a point in time but given the stage of the company’s growth, or a shift in the nature of the work this person may not be a good fit any more. As a manager, you can give this person the ‘permission to leave’ and they will be able to find a place outside your team or company where their skills are better suited. It’ll be better both for the individual and the company.


Managing Distributed Teams

At Automattic, I lead a fully distributed product development and engineering team. This post will cover some of my personal practices for managing teams and if/how this is different in a distributed environment. These practices are probably more useful to newer managers running distributed teams for the first time.

I recently listened to Matt (Automattic’s CEO) and Raj Choudhury’s (Prof at Harvard Business School) discussion about the future of distributed work and the ‘Work from Anywhere’ movement which were the inspirations for writing this post.

DISTRIBUTED PRACTICES

The principles of managing a distributed team are the same as managing a team in person, but a few of the practices are different. People are still people, whether they are sitting right next to you or halfway around the world.

Here are a few practices that I’ve found helpful:

  • Trust: Start from a place of trust. Assume positive intent in written communication, and assume your team is working and trying their best regardless if they are sitting right next to you or they are working from home.
  • Expect Asynchronous Communication: Don’t expect a response immediately, even over chat tools like Slack. Learn how to use Slack asynchronously, and set the same expectation on your teams. I deleted Slack from my phone (because I would miss things), and close Slack on my computer when I want to remove distractions. I respond to messages in batches, and use the reminder feature if I need to come back to something later.
  • Focus on Output: Don’t falsely assume someone is more productive because they work longer hours (even when working in person). Focus on the quality and quantity of the work produced by an individual vs. the number of hours worked.
  • Clear Goals, Roles, Expectations: Develop clear goals and a shared understanding of the ‘why’ behind these goals, roles and responsibilities and what is expected of managers (and their teams) in terms of output. Extreme clarity here leads to more empowerment, not less, in my experience (one of my takeaways from Essentialism, by Greg McKeowen, which I recommend).
  • Project Kick Off: For new projects, with new groups of people working together or working across different teams it’s good to get alignment right at the start. I suggest experimenting with a kick off call with project stakeholders and participants followed by a written summary. The call may be difficult to schedule, and less conducive to working across time zones. but project kick offs are infrequent enough that I think these calls are worth it.
  • “Grab a Room”: If you sense a real time conversation is going off the rails in Slack and if it was in person you would ‘grab a room’ to chat it through, do the same over Zoom for 10 minutes. It helps if your team is not inundated with regular meetings so this can happen more seamlessly. I personally also leverage ‘office hours’ to skip level meetings a few times a quarter. 
  • Hiring: When hiring folks who are distributed, put extra weight on the quality of their written communication and their ability to work in a self directed manner. Documentation becomes even more important in a distributed environment.
  • Feedback: Give frequent, specific feedback both positive and developmental over Slack or in your regular 1x1s (both personal and project related). Write up more thoughtful feedback every 6-12 months. We all have recency bias in the longer reviews, so I keep a record of the small pieces of feedback in a running document. At Automattic, we have a tool called ‘Kudos’ which allows folks to send public thank you messages to a few colleagues a month. It’s a nice way to show appreciation.

MANAGEMENT DURING A PANDEMIC

Managing a distributed team during a global pandemic (Covid-19) requires greater care and empathy. Many folks who are working from home had it forced on them and it may have felt jarring. They may have additional responsibilities of looking after their children, caring for sick/old folks or dealing with loss either directly or indirectly. There is also a psychological toil that is hard to quantify, and simply not knowing when we will return to “normal” can weigh on people. As a manager, simply recognizing these issues explicitly and then being empathetic to their circumstance can go a long way.

I would encourage your teams to take the time they need for self care, and be accommodating to more flexible hours. If individuals or teams are going to experience a productivity hit, adjust goals accordingly (and publicly) as long as your business can afford it. It will pay off in the long term with improved happiness, productivity which will translate to better employee retention.

I’ve noticed extra output from some folks who are now simply working more to fill the extra time they have, and less output from others who are more affected. Teams realize and recognize this asymmetric contribution and much like any small community there are times where we need to contribute more to help out our colleagues. That’s ok, as long as it’s not permanent.


For more on this area check out the companion post around managing performance.

This series from Greylock is excellent as well – https://greylock.com/workfromanywhere-podcast/

Cycle Touring in New Zealand

In 2015, I went on a 5-week bicycle tour around the South Island of New Zealand with my cousin, Hanif. It was a great trip and I have really fond memories of exploring the country on two wheels. Most people do a similar route in a car, but if you have the time and are looking for an adventure, I highly recommend cycling.

We had a real sense of freedom on the road. We stopped when something piqued our interest, had very few possessions and lived simply (mostly staying in hostels). The long rides put me in a meditative state and gave me the time and space to appreciate the beauty around me while improving my fitness.

Preparation

Our preparation involved three main components:

  • Camping v.s. Hostels/Hotels: The main decision you should make before the trip is if you want to camp vs. stay in a hotel or hostel. We opted to stay in private rooms in hostels which was about $40 per night per person. After a long day on the bike, a nice hot shower, a soft bed and laundry were worth the cost to us. You also save on a ton of extra weight as you don’t have to carry all the camping and cooking gear on your bike, which makes it much lighter. If you have the means, I’d highly recommend staying in hostels along the way (confirmation bias).
  • Gear: Gear planning was a very important part of the trip. It was important to pack really light because everything we brought had to be carried on our panniers. Our bikes (Surely Disc Trucker) were touring bikes made out of steel (not carbon) because they are easier to repair in case something went wrong. We rented this and the panniers from Natural High in ChristChurch. We used this gear list as a starting point and did not pack any of the camping stuff. We ended up with this list, and bought most of the stuff for the trip. We bought high quality Gore bike gear (see the matching blue jackets in the picture below) and almost no casual clothes. The merino wool base layers were also great. The rides and the conditions can be really tough, and having good quality equipment really helps – so splurge a little.
  • Route: The best resource for planning the route was Cycle Tour New Zealand. My friend, Paul, did a similar trip a few years before us and he was the inspiration to me for going on this adventure. His advice was invaluable and we ended up doing a shorter route than him which we documented in great detail here in case it’s useful for others. We usually cycled for about 3 days in a row averaging about 40 miles a day, and then took a rest day where we hiked, white water rafted, canyon swung, heli-hiked on a glacier, played golf, tasted wine and generally relaxed. 40-60 miles may not sound like much but the roads are hilly and our bikes were heavy.
  • Fitness: Before the trip, we tried to ride our bikes in SF and NYC, do squats and lunges but it was not sufficient and we were SO sore after the first few days. At the end of the trip we were definitely stronger and fitter and could ride for much longer but we certainly felt like we could have been in better shape before the start of the trip.

Highlights

The scenery was absolutely stunning and extremely varied throughout our cycle ride (in April/May). There were some days where it was below freezing and other days where it was like a summer day. We were in the mountains, on the coast, in semi arid terrain but most of the time we saw beautiful farmlands with mountains in the background.

The people were also so chill and friendly – one of our fondest memories was being befriended by a group of hunters who shared all their beer and lamb with us (sparing us squashed cheese sandwiches for dinner) and by the end of the night we were their ‘Maori Brothers’.

A very common scene

Queenstown

Queenstown is the most fun place we visited. We loved it here and did all the touristy things like jetboating, canyon swinging (like a bungee jump + swing) which was scary AF, golfing at Arrowtown, and enjoying good food and beer. A highlight was day hiking the Ben Lomond Saddle trail which was challenging and had great views. The ride from Queenstown to Wanaka up the Crown Range mountains was an absolute beast and our hardest ride together.

Abel Tasman

Abel Tasman is all the way on the North West side of the island and it is amazing! We kayaked in the water and hiked on the trails around the beaches and coves and it was a really nice change from all the long days of cycling. We spent 2 full days exploring here and loved it.

Abel Tasman

Fox Glacier

We stayed at a nice b&b here after a long ride in and spent the next day heli hiking on Fox Glacier. It was a little cheesy and touristy but it was really fun and we felt it was worth it (despite being the most expensive thing we did all trip).

Lake Tekapo

Lake Tekapo was one of our first stops and it was such a nice little town with a relaxed vibe and a tasty Japanese restaurant (Kohan) with a great view. We hiked, played tennis and generally really felt at peace on our rest day here.

Lowlights

Magpies

I’m frightened of birds (mainly crows) and I was constantly freaking out that the magpies that we saw on side of the road would swoop at me and attack me. This apparently only really happens from Aug-Oct when their chicks are hatching but there are attacks all year. Every time I saw them I was nervous, but in the end was never attacked.

Check out this terrifying video!

Harsh weather

On some days, the weather was really harsh but it’s all part of the fun. On the days with really terrible thunderstorms and heavy rain we opted to take a bus instead of survive through 4-6 hours in those conditions and on other days we just powered through. In all we were very lucky with the weather. When Hanif left and I cycled solo for the last 5 days I had my hardest day completing 70 miles from St Arnaud to Renwick against with intense headwinds. I could have used my buddy to keep me motivated on that day.

Milford Sound

I thought the Fjords at Milford Sound were over-rated and it was a really long day trip from Queenstown. We felt like cattle being herded on a very scheduled trip, and the scenery was not as impressive as other parts of our trip. It was the only time we felt like we were on a ‘touristy’ trip after spending most of the time on our bike adventuring. I would suggest skipping it.

Milford Sound

Overall, this was an amazing trip that felt like it was off the beaten path and was great for my mental and physical health. I’d recommend it to anyone who is looking for a really great adventure and has the time, but definitely do it with a friend or family member.