Leadership Remote

Hard Work

The best way to grow professionally in remote leadership positions is to proactively take over hard work in adjacent domains from your peers or boss. You will expand your ability to execute complex cross-team initiatives and prepare for the next step in your career.

This is the idea that stuck with me the most from reading An Elegant Puzzle. Let’s go deeper.

What Is Hard Work?

Hard work is:

  • Any work nobody is asking you to do.
  • It doesn’t look fun; nobody is rushing to do it.
  • Work outside of your domain and comfort zone.
  • Poorly defined, with loose criteria of success.
  • Requires functional skills you don’t have.

Example 1: You’re an engineering lead. Your scope is to lead the development of an API and accompanying docs. In one of the technical leads meeting, you learn that the company is gearing to revamp the budgeting process. This change will have a significant impact on all technical leads. Someone should represent engineering in the process. The head of the engineering org is swamped. Taking responsibility for representing eng’s interests is hard work.

Example 2: You’re a customer success manager. One of the technical teams is a frequent source of bugs that you hear from customers; long bug resolution times make some customers abandon the product. This is a frequently discussed topic in the company, but there’s no obvious resolution. You proactively offer to help the technical team improve their backlog management and find an effective triaging process. You don’t know much about the technical teams’ internal processes, but you have a great understanding of customers’ priorities. Crossing the team boundary to the other side and finding a solution within another team is hard work.

You can probably come up with several examples like this within your company without much thinking. All of these represent hard work.

Why Do it?

Aside from flexing your problem-solving muscle, hard work confers several benefits that are hard to find elsewhere:

  • Understand Other Teams
  • Understand Your Boss
  • Grow Your Horizontal Expertise

Understand Other Teams

Taking jobs in adjacent domains enables you to understand other teams at a level you can’t attain by reading docs or attending meetings. If your company doesn’t have a rotation program for managers, taking on hard work is one of the best ways to become a part of other teams within the company temporarily.

By moving work through other teams, you learn their cultural norms, what makes them tick, and their process.

This knowledge is a superpower when executing cross-team projects with ever-increasing complexity, a frequent expectation of all managers.

Understand how other teams spec out work, prioritize and schedule enables you to tailor information to their needs when the time comes. You will find yourself collaborating with them with little time to getting to know each other; serving information in the right way makes collaboration easier.

You will also understand how other teams operate within the context of your company. You will discover many tricks and strategies on how to work within your company’s system effectively. This information is specific to your company, so other teams are one of the only ways to source it.

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Understand Your Boss

In many cases, taking on hard work means easing your boss’s load in one way or the other. Frequently hard work takes the form of representing your broader organization within the company or helping other teams within your org. These are workloads core to your boss’ role.

By executing hard work, you’re working on tasks that’d be your bread and butter if you were promoted into the next position on the company ladder. Hard work allows you to build an “ahead-of-time” experience that provides a peek at what’s next. Will it be a route you’ll end up liking? You’ll also make a stronger candidate in your company or others when the opportunity arises.

Even if you’re not gunning for your superior’s position, micro-dosing their workloads into yours can work wonders for your mutual partnership.

By taking your boss’s viewpoint, you can much better appreciate their points of leverage and uphill battles they’re facing. This new information helps you understand where you can offer valuable help and, conversely, what your boss can deliver to you. Your 1:1s will become more engaging as suddenly you share several workloads and challenges, sparking exciting conversations and lessons you can apply back in your home team.

Horizontal Expertise

If you’re a lead, you should already be exceptional in your functional domain.

But to take the next level in your career requires more. You need to become a versatile leader with a broad set of knowledge in many functional areas – from marketing through product management to financial management. After all, the higher echelons of leadership are all about cajoling a diverse set of teams into pursuing a shared vision, goals, and process. Understanding individual vantage points is essential.

There’s no better way to ramp up quickly in a ton of functional areas than collaborating with other teams in the company within their domains.

When working with other teams, you’ll take part in their daily decision-making and pick up on considerations unique to the specific team. You’ll gain new vocabulary for discussing particular kinds of problems. And you’ll understand why they balk at seemingly minor asks.

All of this information will become immensely valuable in the future when you try to align your team’s resources, strategy, and execution tactics with other teams. The ability to appreciate specifics that matter to other teams enables you to take them into account ahead-of-time instead of becoming predictable scope creep mid-way during a complex project that’s already late.

Where to Find It?

If you’re convinced that hard work is worth tackling, where can you find it within your company?

This is where things get easy. There is a lot less competition for hard work.

In meetings, company chat, and anywhere else your company communicates, look for phrases like:

  • “It’d be great if someone…”
  • “We could really use…”
  • “We we’ve been talking about this for six months already…”
  • “There’s no responsibility for…”

These are all hidden prayers for someone to pick up the flag and run with it. In many cases, they’re loosely formulated as the person uttering them doesn’t have the time to specify the problem and required steps to solve it in detail. (this is a core part of dealing with hard work after taking it on)

Every time you hear these prayers, think about if the problem at hand sounds like a good learning opportunity, and if the risk that it brings is acceptable.

Try to prod a bit for more information before offering help, but most of the time, you will need to take a leap of faith and offer up a firm commitment.

If you manage your time well, you should always have a bit of slack time available for unexpected work. If you don’t, taking on additional work outside of your core scope is a great opportunity to improve your downward delegation ability and transfer some of your current responsibilities to your team temporarily (and hopefully make the changes permanent).

Note for Remote Leaders

In remote settings, we tend to have less organic collaboration and low-touch interactions with other teams. The social bonds that become bridges for organic collaboration between teams are weaker, and opportunities to strengthen them are scarce.

This scarcity makes hard work all the more valuable in remote settings. It’s one of the few tools to consistently increase ties to other teams and getting insights that allow you to find cross-team synergies that help your company thrive.

In Closing

As you take on hard work consistently, you accumulate essential knowledge that makes it easier to execute more of it. You enter the virtuous circle of collaboration where a robust internal network enables you to take shortcuts to success, becoming a ninja facilitator of the company’s most complex workloads in no time.

If this sounds great, you probably already have a couple of ideas about where you could make an impact. Commit and start your growth through hard work!

Photo by Thomas Marban on Unsplash (much like omakase sushi, hard work comes loosely defined and with high expectations 😋)


Becoming a Native Remote Citizen

In this post, I’m trying to summarize the pitfalls of working from home without the remote-first mindset I’ve experienced. I’m also adding a few tips that worked for me over the years. They helped me at various points of my remote journey. I hope others will find them useful as well!

This year, I’ve seen many of my family members and friends transition to working from their homes full-time. In most cases, their workplaces were not built for remote-first and now embrace the always-online culture. Hearing their experiences reminded me of how tough is the journey from working in the office to being fully-remote.

I’ve had the luck to work at Doist since its relatively early days. We’ve built Doist as a fully-remote company from the ground up. This advantage gave us the luxury to develop our culture and process from the ground up to complement remote work’s strengths and avoid its pitfalls.

We’re not the only ones; other great companies like ZapierGitLab, or Toggl together form a community of remote-native companies. Remote-native companies vary in many aspects, but they frequently emphasize two aspects of their culture:

  1. Asynchronous communication whenever possible. The belief that preferring longer-form but slower forms of communication produce better outcomes while taking less toll on their workforce by removing the “always online” requirement.
  2. Work-life balance. The belief that working 12+ hours a day is not sustainable and will hurt both the employees and the company in the long-run.

Asynchronous communication and work-life balance are tightly complementary. Work-life balance is hard to achieve with constant requests for meetings and phone calls from dawn to dusk. Asynchronous communication is likewise hard without minding work-life balance; slipping into DMs is just too comfortable without a mental block in place.

Unfortunately, many companies transitioning to online-first culture are altogether eschewing both asynchronous communication and work-life balance.

Late-night pings or Teams or Slack are commonplace, and so are meetings scheduled in the previously-sacred lunchtime. The amount of meetings has not decreased; online meetings are even more draining compared to in-person ones. To top it off, many people end up working longer hours, creating the perfect coctail for burnout.

A less talked about but crucial aspect of working from home while eschewing async communication and work/life balance is an impact on the family. Doing homework while your mom is going through a series of heated meetings in the other room is a draining experience for the kid. And for the rest of the family as well.

In short, lots of companies are going remote but are not picking up remote-native practices, hurting their people and themselves in the long-run.

In companies where the big picture is hard to influence, I’d like to share a few practical tips that helped me over the years, from two distinct perspectives:

  • Individual Contributor Tips. Tips you can apply individually, without requiring broader buy-in first.
  • Team-Wide Tips. If you can influence your team (being the team lead helps, but it’s not necessary), these tips could come in handy.

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Individual Contributor Tips

Talk to your team lead. The first thing I recommend. It’s your team lead’s job to make sure you have the best possible conditions to succeed. If the new team meeting interferes with you needing to pick up your kid from school, it’s your team lead’s job to figure out a solution. If you’re exhausted by all the Zoom calls, ask your team lead to work on a team process that’s less meeting-heavy.

Ask for an agenda before accepting a meeting. If you can, explicitly ask for a written agenda before accepting a meeting or a call. If the other person can’t present an agenda, try to politely postpone the meeting until there’s one. Even if you fail in delaying the meeting, you have created an expectation for next time, resulting in fewer meetings down the road.

Comment on the agenda before the meeting. If you get an agenda before the meeting, try to reply to it with what you’d say during the meeting and ending the email with something along the lines of Let me know if you’d like to discuss further; otherwise, we could skip the meeting? Most people want to skip meetings as much as you do; make it as easy for them as possible.

Delay responses to unimportant requests. If you get lots of DMs from specific people asking you about things they could quickly solve themselves, intentionally delay your answer. This is frustrating for the other person in the beginning, but you motivate them to self-solve. In the long term, the stream of messages slows to a trickle; everyone is better off.

Unapologetically exit overtime meetings. If you have a problematic meeting scheduled for 30 minutes but routinely running for 60 minutes, try to schedule one of your meetings to follow the problematic one. This allows you to exit the first meeting at the 30-minute mark gracefully. Be explicit that the meeting was scheduled for 30 minutes and that you have another meeting coming up. Doing so generates pressure on the meeting organizer to run the meeting better and not go overtime. 

Have a hobby with scheduled events. Having hobbies with fixed time slots (language lessons, music band practice, etc.) that are hard to cancel is incredibly helpful to help to build the crucial work/life boundary.

Most of the tips are about adding small bits of friction to reduce the frequency of interruptions. If people contact you, they should feel a bit of pressure to come prepared.

Team-Wide Tips

If you can effectively influence your team or set policy, you’re well-positioned to improve your team’s well-being and long-term productivity.

Model individual contributor behaviors. If you start rejecting meetings without an agenda and make it clear that it’s ok to not respond within five minutes, as suggested above, your team will quickly follow and adopt the same behaviors.

Create a “Meeting Best Practices” document. Early during my time at Doist, we created a policy for conducting meetings that enshrined best practices like “no meetings without an agenda” or “all meetings last a maximum of 60 minutes”. This made it clear that meetings have limits. Having a similar policy on the team level can improve the meeting culture as well.

Designate a specific person to run team meetings. If you have a person in the team who enjoys running meetings and can devote energy to it, ask them to run team meetings. In many cases, this person will not be the team lead. If you can find a great person for this job, you’re giving the whole team a role model and a mentor for running effective meetings.

Promote a culture of sharing current stress levels and emotional challenges. By openly talking about your mood, stress levels, or health problems and encouraging the whole team to do the same, you can create a team culture of caring for each other and cutting folks slack when they’re not at their best. Team members are great at supporting each other through burnout or other work/life balance issues, but they need to know that it’s happening.

Model, document, and share. As suggested in the book An Elegant Puzzle by Will Larson, once you find behavior that works and spread it in your team, consider evangelizing it beyond your team as well. Other parts of the company will be happy to adopt battle-tested solutions to problems they’re also likely facing.

In Closing

Becoming a remote native is a journey. Working remotely has many great perks, but setting firm boundaries early in the process is essential to preventing burnout down the line.

Solid boundaries take time to build, especially within companies new at remote, but they pay off with sustainable personal and team performance in the long-run.

If you’re new to remote, take care of yourself, and be honest about your limitations to your team as well as to yourself.

Image Credit: Photo by XPS on Unsplash