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 😋)


“Partnership Feeler” Meetings

Organizing productive meetings with clear-cut purpose, contained to your team and company is challenging enough.

Then there are the partnership feeler meetings.

The purpose of the partnership feeler meetings is to establish a personal connection with a potential partner company while brainstorming ideas for possible collaboration, ideally within thirty minutes. It’s a tall order, especially for folks who are not born salesmen.

Compared to other forms of meetings, it comes with a few twists:

  • Lack of a prior connection makes it impossible to tailor the meeting to the preference of your counterparts.
  • Various stakeholders on both sides are curious and it could be useful to include them, but only a few participants contribute during the meeting.
  • Abstract meeting goals that frequently boil down to trying to find something to talk about in subsequent meetings.

The structure of the feeler meetings usually consists of:

  1. Pre-meeting. One person from either company initiates a meeting; people are looped in and invited; agenda is set.
  2. Small talk. At the onset of the meeting, people from both sides try to break the ice.
  3. Going over the Agenda. The meat of the meeting where ideas for collaboration generate before the meeting are discussed.
  4. Follow-Ups. Follow-ups of the most promising ideas are identified.
  5. Post-Meeting. Teams from both companies internally discuss their feelings about the meeting and potential next steps.

Nailing the partnership feeler meeting is a sum of excelling at executing the individual parts. Let’s examine them individually.


Keep the circle of participants from both sides as small as possible. People frequently join because they’re curious about the other company, but they have limited stake in the meeting. Being overly inclusive leads to large meetings with lots of uncomfortable silence. Make it clear that no definitive decisions will be taken during the meeting and you’ll keep notes and distribute them afterward. This disclaimer helps quell people’s fear of missing out and gives them an easy out of the meeting.

After you have the participants list, reach out to participants from your company and brainstorm ideas together. This will lead to stronger ideas and better engagement during the meeting. Sometimes you won’t avoid creating a presentation solo, but it’s always better to make it a team effort, even if others’ contributions are only symbolic.

Once you have the agenda ready, send it to all participants well ahead of time (at least a day, ideally more). This helps the partner company form an opinion on ideas and creates a bit of healthy pressure on them to come up with counter-ideas. Once you know that the other side has done a lot of prep, you don’t want to look bad by going to the meeting empty-handed.

Also, always prepare slides or other visual assets that you can share as agenda during the meeting. They help immensely with focusing the discussion and injecting a sense of momentum.

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Small Talk

Most partner meetings start with small talk that focuses on either very general things (weather, season, etc.) on sharing tidbits about how each company works.

If you can, direct the small talk into talking about your respective companies. You can quickly gain bits insight into how the other company works and set expectations for yours. Small talk is a great opportunity to understand the planning cycles or organizational quirks of the peer company and share yours. If you can make this discussion happen, it can become the most valuable bit of the entire meeting. Whether the other company runs weekly sprints or if they execute top-down quarterly plans will have a big impact on your future relationship. Getting this information early is a win.

The fewer participants you have in the meeting, the better the small talk opportunities. Making fun of the process quirks is something people are understandably not comfortable doing if large portions of their company are present. Keep in mind that you also need to be comfortable sharing.

Lastly, don’t skip introductions.

Going over the Agenda

This part is similar to other kinds of meetings.

Ensure that the conversation is inclusive, and everyone is comfortable with sharing ideas as well as asking questions.

Keep in mind that the goal of these meetings is to generate ideas and establish rapport. Sticking to the agenda is less important compared to other types of meetings. If the meeting derails into an unstructured discussion, it’s a good signal that rapport is being built and ideas are flowing. If you tend to be a stickler about sticking to the agenda, loosen the reins a bit for this meeting.


If you succeeded during the Going over Agenda portion of the meeting, you have several concrete actionables in your meeting notes. Take a few minutes to recap the actionables for both sides and ensure that it’s clear who is responsible for the follow-ups.

Asking companies you’ve just met for deadlines might not be possible. Still, by sharing a specific timeline for individual actionables you’re responsible for and asking participants from your company for the same, you can maximize the chances that the partner company will commit to a specific timeline for follow-ups as well.

It’s helpful if you can formulate the actionables as concretely as possible. “Discussing with engineering and sharing which of the ideas are in principle doable” beats “Thinking about it more and regrouping in two weeks”.

Besides being more useful generally, concrete actionables make it easier to inquire about progress from either side should there be a lack of communication in the weeks following the meeting.


After the meeting itself is concluded, it’s useful to reach out to participants from your side to gauge the overall feelings and ensure alignment on the next steps. In most cases, you shouldn’t need another internal meeting to do the debrief; a few messages can do the trick just as well.

Don’t forget you’ve committed to provide meeting notes to people not attending the meeting. Take a few minutes right after the meeting to polish the notes and write a meeting summary, sharing it with all participants in the meeting and with any people who expressed interest. The longer you wait with this step, the longer it’ll take to clean up the meeting notes. You start forgetting nuances of the meeting the minute it ends.

Lastly, ensure you’re tracking follow-up items in the appropriate place. If they’re only in the meeting notes, it’s easy to forget them. Adding them to your task manager or the team issue tracker will help follow-up more consistently.

In Closing

Don’t worry if you feel like some of the partnership feeler meetings aren’t productive. You can do everything right; some meetings will still be unproductive. Not all partnerships are meant to be. Walking away with an understanding that the company is not a good fit is a valuable takeaway as well.

Regardless, excellent preparation and a positive attitude go a long way and positively impact the value you get out of these meetings, helping you find the best companies with which to partner.

Cover image credit: Photo by 🇨🇭 Claudio Schwarz | @purzlbaum on Unsplash


Engaging Your Interviewer

We’ve been looking for Windows devs to help us work on our Todoist for Windows 10 app.

I want to share a few tips on how to have a good interview. They’re based on my interviews of around 50 people. If the tips feel basic, you’re probably already making a consistent strong impression during an interviews!

For the busy crowd, the tips are:

  1. Prepare Good Questions
  2. Go into Specifics
  3. Provide Criticism
  4. Have a Conversation
  5. Don’t Ramble

1. Prepare Good Questions

This is a big one. Lots of candidates have no questions. Not about the role, not about the culture, not about our tech. It’s a red flag for a few reasons:

  • The candidate didn’t prepare for the interview. It might not be true, but a lack of questions creates that impression.
  • The candidate doesn’t care about our specific company. We’re looking for people excited to live our culture and build our products.
  • The candidate lacks curiosity. Again, it might not be an accurate assessment. But when you go through our blog and products, at least a few questions should pop up.

Thoughtful questions give you more information about us. They also serve to show your qualities as a prospective colleague.

Great questions are many, here are few common themes:

2. Go Into Specifics

Some candidates are reluctant to talk about the technical details of their work. It gives the interviewer less information to assess a candidate’s technical prowess.

I sometimes share this feedback with candidates. They frequently say they were afraid to stay within the interview time constraints. The best candidates demonstrate their expertise while keeping their answers concise.

Interviewer: “Can you share a technical difficulty in your last project and how you overcame it?”

Interviewee — Bad Response: “We were working with a large codebase that was very complex. Our biggest challenge was to try to simplify it. We worked for a few months on making the overall architecture more simple. We successfully made the app more maintainable.”

Interviewee — Good Response: “We inherited a monolithic codebase. It was tough to introduce new features without unintentionally changing behaviors of other parts of the system. So we broke the code into smaller components while using a DI container. We picked Unity because the interception feature is cool; we use it for a few cross-cutting concerns. Do you use a DI container in the Todoist UWP app?

3. Provide Criticism

It’s very hard to be critical of what the interviewer says. You want to make a good impression and are afraid that the interviewer won’t like you if you criticize them. If they get offended, you’re better off looking for a different job anyways.

Candidates that offer constructive criticism during a job interview impress. Giving feedback during an interview shows you enjoy both providing and accepting feedback. Willingness to express criticism under challenging conditions an essential quality for companies that want to keep improving.

For more on how to provide good feedback, give the Radical Candor book a shot.

4. Have a Conversation

This one is the hardest to do, especially if you’re not a great conversationist. But if you manage to draw the interviewer into a discussion, you will make a strong impression.

Aside from creating a strong impression, there are other benefits. Having a fluent conversation reveals more about company culture and engineering values. In cases where the interviewer is your future team lead, you can get a much better sense of what kind of boss they’d be.

If you don’t feel like a skilled conversationist, here are a few great tips from Sean Plott, one of YouTube’s engaging storytellers.

Sean’s Conversation Tips

5. Don’t Ramble

Rambling answers are common during job interviews. The interviewer asks difficult questions, and the interviewee doesn’t always have a crisp answer at hand. It’s easy to start answering and come up with the rest of the answer on the go. Don’t do this.

If you get a hard question, follow a three-step process:

  1. Take a few breaths; organize your thoughts.
  2. Answer the question.
  3. Stop talking.

Step three is the most difficult one. You will inevitably come up with more imaginative ways to answer the question as you’re answering and want to share it. This approach frequently results in hard-to-understand trains of thought from the interviewer’s point of view. It’s better to finish your thought and let the interviewer engage if they choose to.


When having interviews, try to be engaging and give the interviewer enough information to make a fair assessment.

Adopting these tips can also make the interview a fun experience; instead of a tense and stressed-filled one.

If you notice you’re having a good time while the interview is happening, you’re on your way to getting a great job. The best interviews are the ones where everyone learns something.

Cover Image Credit: Photo by Juri Gianfrancesco on Unsplash