Calendars show you events. They don’t show you reality.

When we moved from paper to digital, we copied the model exactly. An event has a name, a time, some notes, and a place. That’s it. Forty years of software evolution and the calendar on your phone works the same way a paper planner did in 1985.

The problem is that events don’t exist in isolation. They have transitions. And for anyone managing a family, those transitions are where the stress lives.

Take a travel soccer game. It’s on the calendar at 4pm. Simple enough. But actually getting to that event looks like this: uniforms and cleats have to be located and packed, water bottles filled, snacks pulled together, chairs grabbed from the garage. Your kid’s team warms up 45 minutes before kickoff, and the field is 40 minutes away. You’re looking at a 2pm departure.

That 4pm game is a 2pm game. Your calendar doesn’t know that.

It’s not just sports. A dentist appointment at 10am means leaving at 9:30, find parking, walking in, and filling out the form they hand you every single time even though you’ve been a patient for years. A 7pm dinner reservation means everyone dressed and out the door by 6:20. A morning meeting means prep the night before.

Every event on your calendar has a transition that isn’t on your calendar.

That’s the gap. And it’s where families fall apart, where people feel perpetually behind, where the day that looked manageable on a screen turns into chaos by noon. We planned for the events. We didn’t plan for the reality around them.

Calendars need to evolve. Not with more features or AI suggestions (without context), but with a different philosophy entirely. Stop treating events as isolated points in time. Start treating them as the center of everything they actually require.

Stop scheduling events. Start scheduling transitions.

Until then, your calendar is just telling you what’s happening. It’s not showing you the plan.

Software development was never the hardest part of building a software business. Strategy was. And everyone rushing to build their first app right now is about to learn that lesson.

For decades, building software was the bottleneck. The barrier to entry. The reason you needed funding, a technical co-founder, or a dev team before you could even get started. That barrier kept a lot of people out, but it also hid something: the real challenge was always strategy. Most people just never got far enough to find that out.

Now AI has removed that barrier. And every app that exists today is about to face an explosion of competition. If your product can be described in a detailed prompt, someone can build a simple version of it in a week or two.

Features are no longer a moat. Code is no longer the advantage.

Strategy and distribution are.

Not strategy as in a pitch deck with a TAM (Total Addressable Market) slide. Real strategy. The kind that answers one question: what unique value are you bringing to the market that nobody else is?

Not “better.” Not “faster.” Not “more features.” Unique.

Because if you’re building the same thing as everyone else, AI just helps you arrive at a crowded market faster. You end up in a cluster of identical products fighting over the same users, racing to the bottom on price or features.

The goal isn’t to compete. It’s to maneuver around the competition entirely. Find the open space. The gap between what people actually need and what’s currently available to them.

But even unique value isn’t enough if nobody knows about it. Distribution determines whether anyone ever sees what you’ve built. Audience. Community. Trust. Relationships.

And if you think setting up an AI agent like OpenClaw to automatically market your app is the answer, think longer term. We’re already drowning in spam. AI-generated marketing is only going to get more intense. The noise is about to become deafening. Real distribution is built on real trust, and that still takes time.

Building is the part I love. But I’m spending more and more of my energy on the two questions that actually determine whether any of this matters: what unique value can I offer, and how do I help people discover it?

AI changed how we build. It didn’t change the strategy game. It didn’t change how humans discover and trust new products. That part is still slow, still personal, and still the real work.

The hardest part of juggling parenting and building software isn’t the work itself.

It’s the context switching.

Product strategy → bus stop pick up → homework → sibling mediation → listen to what happened at school → back to my desk → map out the evening → code → check traffic → get the kids ready for sports → get everyone out the door.

That’s not a bad day. That’s a Tuesday.

And for a long time, I let it beat me up. I’d sit back down at my desk after the afternoon chaos and wonder why I couldn’t just “lock in.”

Then I realized something.

I context-switch 15+ times between 3pm and 6pm. And I was treating it like a personal failure instead of what it actually is: an operational problem. One that at work, I’d have real tools to solve. At home? I had a shared Google Calendar and a group text.

So I started treating my household like I’d treat any high-performance team.

I pre-brief my kids on the evening schedule the same way I’d prep a team before a sprint. When everyone knows the plan, the chaos drops.

I used to check Google Maps every day before leaving and make mental calculations to make sure we got to events on-time. Now I’ve built a tool that syncs travel time into our family schedule with traffic estimates. What a game changer. No more, “What time do we need to leave?”

“I thought you were getting them.” That sentence used to run our household. Now we have clear assignments for every pickup, drop-off, and practices. No assumptions. No last-minute scrambles in the group text.

I didn’t get less busy. I got more intentional.

The context switches don’t go away. But the right systems and the right tools turn the most overwhelming part of your day into the part where you can finally breathe.

Authoritarian leaders are toxic. I should know. I was one.

My first job out of college was managing a team of software engineers. My degree helped me handle the project management side of the role, but the people side? I was on my own. Like most people in that situation, I looked to my own past experiences to fill the gap. I’d had a mix of managers prior to becoming one, but the idea that I needed to be a “strong” one seemed to win out.

I was a terrible first-time manager.

I made all the classic mistakes. Micromanagement. Over-control. Resistance to giving anyone more independence. A fragile ego. Intimidation. Threats of consequences. Praise was rare. Criticism was abundant. No questioning the direction. No pushback tolerated.

The people I managed hated me, and for good reason.

When I asked my support system outside of work what to do, the advice was predictable: the employees were the problem. Fire them. Make examples. Show them who’s in charge.

Terrible advice. I knew deep down I was the problem. I just didn’t know where to go from there.

My grandfather was an avid reader. I always marveled at how much knowledge he’d accumulated over the years, across all kinds of topics, all on his own. So I turned to books.

No single book solved my issues. It was a combination from different fields that helped me understand what managing people actually is: it’s coaching.

A good coach pushes the team toward independence. Builds people up. Gives clear, honest feedback on how to improve. When things go wrong, takes accountability instead of looking for someone to blame. Lets go of their ego. Listens. Asks questions. Builds real connection. Pitches in when the team is stuck. And learns how to read the room: most of the time, let the team make the call. In critical or emergency situations, when fast decisions matter, that’s when you step in and decide.

Leaving Zillow was hard, not because I was walking away from a career, but because of the people. My team was amazing. I felt a deep connection with them. The authoritarian manager I started out as had disappeared. In his place was someone I’d spent over a decade becoming.

Parenting taught me the same lesson all over again. You can’t use one style. You learn. You evolve. And early on, I saw that the authoritarian approach isn’t what most situations call for. It’s a weak form of leadership hiding behind a strong face. It’s easy to reach for. And it always turns out badly in the long run.

There is a time and a place for authoritarian leadership. Emergencies. High-stakes decisions that need to move fast. But as a default mode? It’s a shortcut that costs you everything that actually matters: trust, creativity, loyalty, and the kind of team that makes something worth building.

“The project Dad’s been working on isn’t going to work out. I have to start over.”

Their faces dropped. They’d been hearing about it at dinner for months. They were excited. They were rooting for me.

And now I had to tell them it failed.

Here’s the thing nobody warns you about when you build something as an entrepreneur with a family: the hardest audience isn’t investors or customers. It’s your kids.

They don’t care about product-market fit. They just know Dad was working on an idea and they see him as the best at what he does. So naturally, this idea in their eyes could grow into something BIG. Like, you know, Mr. Beast league success.

But after the initial disappointment, something happened that I didn’t expect. It opened up one of the best conversations I’ve ever had with my kids. About failure. About what it actually means to try something hard.

We talk about failure a lot in our house. Not making a competitive team. Missing a soccer goal. Failing a test. Making a poor choice.

But this conversation was different. Instead of what might feel like a “lecture” from Dad, they got to see me in a deeper, more meaningful way.

I told them about all the things I got wrong before building Naked Apartments. The bad ideas. The false starts. The moments I was sure I wasn’t cut out for this.

And I told them the truth: every single one of those failures was necessary. Including this one.

Not in a motivational poster kind of way. In a real, practical way. Each one taught me something I couldn’t have learned any other way.

Starting over isn’t fun. But I’ve done it so many times. And I know something now that I didn’t know when I started down this path 25 years ago. The starting over IS the work. It’s what entrepreneurship is all about. It’s not a detour. It’s the path.

My kids will fail at something big in the future. And when they do, I want them to remember this conversation. Not because Dad had all the answers, but because he didn’t. And he kept going anyway.

“There’s a difference between knowing the path and walking the path.”

Six years ago, I walked away from a great role at Zillow.

No dramatic exit. No manifesto. I just realized I was missing it. The stuff that actually matters.

My kids were growing up fast. And I had a choice: keep climbing, or stop and be there for them.

Two moments helped me make that decision.

The first was a bus ride home from work one evening. I realized that at the rate I was going, I would never get to see my kids play sports, be their coach, or be there for the milestones that matter most. I was almost never home. And when I was home, I wasn’t really there.

The second was Rich Barton, Co-Founder of Zillow, speaking at a company all-hands in Seattle. He described with great enthusiasm a cherished memory of making his kids breakfast every morning, something he called “The Breakfast Club.” It sounded wonderful.

In that moment, I realized I wanted a life filled with those memories. So, I chose to be there.

In the years since, I’ve been investing, managing real estate, and giving back to the community. I also went right back to what I love. Building tech. Not for a company’s roadmap. For people.

I won’t pretend I have some big success story to share yet. I’m still in the middle of it. Still building. Still figuring it out. Learning and growing.

But here’s what I do know: I didn’t miss it. The breakfasts in the morning, the chorus concerts, the soccer games, the many “firsts.” I’ve been there for all of it and with more to come.

“Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”

Over the years, I’ve been asked countless times “What’s your secret for managing a remote team?”. Most are expecting a magical tip that would make the whole remote thing easy.

What I’ve learned over the past decade is there are no simple tips that make managing any team easy. The majority of management principles and lessons you learn to be an effective manager for an office environment are highly relevant for remote work. They just need to be adapted.

I’ve found that remote work can be a great force multiplier. Better communication, productivity, and employee happiness are some of the great benefits. However, I’ve also seen bad leaders get amplified in the worst possible ways. Under a bad leader, the effects in a remote environment can quickly cause employees to become demotivated, increasing their anxiety and levels of stress.

What is most disturbing to me right now is that there are tools being built by companies to empower poor leaders. Tools to literally track keystrokes, watch what an employee is doing via a webcam, and time tracking based on computer activity. It’s absolutely crazy.

After I left Zillow Group, I spent a lot of time reflecting on what made Naked Apartments so special. Inspired by Principles by Ray Dalio, a book I read a couple of years ago, I decided it’d be good to start documenting my learnings for my own clarification and further refinement. If other managers find this helpful, all the better.

I’ll continue to refine this list moving forward as I learn more.

Organization

For a manager to be successful, an organization needs to do their part in putting the appropriate framework in place to help a manager make the right decisions in the best interests of the organization.

1) Define core values and principles

By setting clear values, it allows teams to work cohesively and provide purpose. Most importantly, values help to shape a company’s culture.

In terms of hiring, values and principles provide a roadmap in decision making for future candidates. Without it, you’re allowing each team to figure it out on their own, resulting in a patchwork of values across the organization. This inevitably leads to misalignments and infighting.

2) Foster an environment of diversity and inclusive

Managers and their teams are tasked with hiring and retaining extraordinary employees. If those teams are only looking at a select portion of the population, they won’t be hiring the very best.

Hiring employees from a range of different social and ethnic backgrounds and of different genders, sexual orientations, etc., helps provide a company with a rich culture and varying perspectives.

One of the reasons I personally love all-remote companies is the ability to hire from around the country and even the world. It really opens the door to true diversity. Embrace it in your organization and you’ll quickly see the wonderful benefits.

But a diverse workforce is only part of the puzzle. Organizations need to also create a welcoming environment where all employees are treated fairly and with respect. Additionally, everyone should have equal access to opportunities and resources. If your company is running a hybrid of remote and office employees, this last point will be particularly challenging.

3) Prioritize wellbeing of employees

There is a never ending list of ways to help make employees healthy and happy in any work environment. An organization’s job is never done, as there are always ways to improve.

3.1) Provide flexible schedules and mean it

Many organizations tout flexible schedules, which is a great way to increase employee happiness and quality of life. Sadly, it’s an empty promise at many companies. They want employees at their desks for normal business hours, plugging away.

It’s a huge quality of life game changer that will increase your employees happiness and wellbeing if done properly. So trust your employees to do the right thing.

3.2) Watch out for overwork

It’s counterintuitive, but remote work causes people to overwork, not slack off. Separating home and work is difficult for even us with years of remote work experience. It’s so easy to get caught up and lose track of time.

3.3) Set clear written expectations around work hours

To avoid overwork, make sure to be clear about how many hours you expect employees to work remotely and how to handle flexibility in their schedule.

3.4) Demand employees take time off to recharge

A lot of companies offer unlimited vacation days. Again, an empty promise in most cases, causing employees to take way less time off. Add in remote work and you’ve got a recipe for burnout.

The organization needs to encourage and at times force employees to take downtime.

3.5) Create human connections

It’s easy to get lonely while working remotely. I feel fortunate that I have a great partner and beautiful children to have as a support system. Not all employees have a support system at home, so it’s important for organizations to foster internal networking events (virtually and in-person).

3.6) Provide and encourage participation in mindfulness programs

While there are a lot of benefits to remote work for employees in terms of mental health, there are also many downsides. Because of this, I believe it’s important that organizations provide programs to employees that will help them effectively cope with the highs and lows that come with it.

Manager

As a manager, in addition to the principles below, you will need to champion the organization’s principles.

1) Trust employees

If I only had one principle I could follow from this section, it’d be this one. If you’ve spent the time to hire an extraordinary employee, they should trust them to do their job. They are experts after all.

As a manager, it’s not only important to trust your employees, but to show you trust them. Actions speak louder than words.

2) Give employees long stretches of uninterrupted time for deep work

A major benefit of working remotely is the chance to avoid long commutes and office distractions. Many employees report greater productivity due to remote work, since they’ve got more control over their time. On top of productivity gains, some studies have shown that long stretches of uninterrupted time gives employees less stress.

The productivity gains are all washed away the minute a manager attempts to give themselves meaning by scheduling a slew of meetings for their team. So, next time you get the urge to schedule a meeting, try sending an email instead.

3) Utilize efficient and effective communication for remote work

With your team working in isolation, there is no chance of them overhearing a verbal conversation in the office, so it’s even more critical than ever for information to be free flowing between individuals and teams. It is your role as a manager to help breakdown silos of information and make sure things are transparent to the team.

3.1) Default to written communication over verbal

Information gets lost over time with verbal communications. Written communication can be later referenced and provided to employees who weren’t present in the original discussion.

3.2) Practice being succinct in your writing

We all add a lot of extra unnecessary words into our communications with others. When an organization shifts to mostly written communication, it’s important for everyone to shorten their writing to allow more content to be consumed throughout the day. Succinct writing starts with leaders.

3.3) Set clear expectations

Nothing is worse than receiving a one sentence response to an ambiguous problem with unclear direction. Clarity of information is paramount, even if you sometimes need to sacrifice being succinct.

Also consider the psychological effects of unclear expectations. Remote employees will be less likely to reach out for help and you won’t be able to see their body language, which might usually highlight a person who is struggling with a problem. Without clear expectations, employees could start resorting to cognitive distortions, spend more too much time working, or undergo undue stress.

3.4) Provide timely and contextual performance feedback

It’s easy to forget to give praise or constructive feedback when you don’t see someone everyday.

Now put yourself in your employee’s shoes.

You’re working in isolation. Weeks go by without any feedback. You make some silly mistakes. Still, no feedback. You have a successful product launch. Zip, nadda. You start to question if there is something wrong. “What if I’ve been doing more things wrong?” “Is my manager upset with me?”

A great employee can become completely demoralized in a matter of weeks because of lack of communication on your part. This happens already for many manager-employee relationships in office settings. The problem gets amplified in remote environments with people being in isolation.

3.5) When you need a meeting, run it effectively and with purpose

For many people, it’s just easier to hash something out over a video chat or call. If you’re going to interrupt a person’s day, make sure it’s worth it. Otherwise, you’ll be reducing employee engagement, along with productivity.

4) Evaluate and promote employees based on productivity and creativity, not “face time”

In an office environment, it’s so easy for a manager to monitor an employee’s time at the office to gauge how hard they’re working.

Have you ever seen an employee who is acting as if they’re working hard, but aren’t doing their fair share? I’ve worked with MASTERS of this dark art. They could stretch a task that usually takes hours over many weeks, artfully making it seem as if they were solving world hunger in the process.

Working with colleagues like that made it clear to me that productivity and quality are two of the most important factors in a performance evaluation. The time spent at a desk is meaningless. Output is important.

The problem is many managers don’t really understand what it takes for their employees to effectively do their job, so they fallback on what’s easy. Facetime.

What I love about remote work is it forces you to grade on output. There are no other good alternatives.

To grade an employee on their work, you’ll need to have a broad understanding of what it takes to fulfill the job. By no means should you need deep knowledge.

5) Foster internal networking and connections

In an office environment, it’s easier for networking and human connections to be created organically. Between “Water cooler” conversations, passing people in the hallway, sharing meals together, and face to face meetings, it’s fairly easy to get introduced to people around the office.

In addition, a manager will usually help make some initial connections for an employee during their first few weeks on the job. After that, it inadvertently falls on the employee. Take away the office and the employee will struggle.

In a remote work environment, it’s the manager’s job to step up and not only make an employee feel welcome, but make sure they get to know the right people in the company to effectively perform the duties in their role. This should extend past a new employee’s first few weeks on the job.

5.1) Use weekly video calls to create human connection

Nothing beats meeting in person, but video is the best alternative we have in remote work to make human connections.

What I personally enjoyed most was having a Monday morning call with the Naked Apartments team where we spent time connecting with each other on a personal level and not focusing on work.

5.2) Optimize socializing around team’s preferences and needs

Finally, each organization and team are different. There will not be a one size fits all way to socialize remotely. Your goal is to make people feel comfortable in an environment where they can be their true selves.

5.2.a) Collaborate with the team or an individual on what type of meeting format and time makes them feel most comfortable

Ask them their preferences and let them vote on it.

5.2.b) Schedule networking meetings during office hours

Employees have a life outside work. Don’t make them choose between personal relationships, like family and co-workers.

5.2.c) Make sure the team knows work can be put on hold without ramifications

It should be made crystal clear that deadlines will be moved to accommodate for lost productivity because of a meeting.

5.2.d) Make events fun. Don’t talk about work

6) Assume good intent

One of the downsides to moving to written communication is you lose a vital aspect of communication, which is body language.

That’s a big deal.

Is this person happy or sad, frustrated or being sarcastic? It’s impossible to tell with text alone. The use of emojis can help, but it’s not a replacement to seeing someone in person.

Because of this obstacle, you should always assume good intent until proven otherwise.

7) Conduct weekly 1-1s

Remote work can be isolating, so for some, a weekly one-on-one is something an employee will absolutely look forward to, even if they’re an introvert.

Some all-remote companies allow weeks or even months between 1-1s, which works for their cultures. Personally, I’ve noticed that most employees enjoyed the weekly calls, even to just say hi. Human connection is important.

8) Promote a culture of documentation

I’ve never been on a team that hates having existing documentation to aid in projects, especially when a project was inherited by the team.

Now ask that same team to document their project on top of their existing deadlines and you’re likely going to get in some heated debates.

From what I’ve seen, it’s usually a problem of getting started and facilitation. Many individual contributors simply don’t have the time to think through outlining and organizing thoughts of a big project.

This is where you come in. Help get the team started and add some documentation of your own. You’ll be amazed how quickly your team will jump in and start contributing. Overtime, things will get messy and outdated. Pitch in to keep it organized.

Your efforts won’t be wasted either. Employees will find answers to questions faster, allowing them to get more done. An added bonus is they won’t be distracting other team members with basic questions.

As your organization brings in new employees and teams are reorganized to meet the growing demands, this documentation will serve as a way to ramp up new members.

Through trial and error, I learned some hard lessons in supporting new and junior employees while building my first company, Naked Apartments, in 2009. It was also my first time taking the plunge with managing an all-remote company, along with my fellow co-founders. Turns out, many of the lessons we learned can and should be applied to any work environment. They’re just that more critical to adopt when your employee is working from home, isolated from other team members.

Tips

👋 Make new team members feel welcome on their first day

There is absolutely nothing worse than starting a new job and being ignored for the first week or two, having to introduce yourself to other employees in the company who you stumble upon. As you might imagine, it’s 10x worse in a remote environment.

We found it helpful to introduce them in two ways on their first day.

1. Introduce them formally over email or slack

   Before their first day, ask them a series of questions that gives the team an understanding of their background, personal interests, and what makes them excited to work at your company. Share the results with the team on the employee’s first day.

   Don’t forget to mention their title and where they’ll be making an impact to the organization in the coming months.

2. Schedule a group video chat for a more personal and informal introduction

   Our weekly team call was every Monday, so it was a perfect time to introduce a new team member.

📦 Send them company swag

It’s simple as it sounds. Swag is a big deal to remote employees. The money is absolutely worth it and will make remote employees feel connected to the team and company.

I found that you get the highest satisfaction if you can get it sent out in the first week or two of them joining the company. Make it part of your onboarding checklist so you don’t forget.

🤷 Don’t expect socializing to happen organically

In a remote environment, a new employee doesn’t have the same opportunities to socialize as someone in the office. For example, meeting others in the hallways, lunchrooms, and social events.

As part of the onboarding process, it’s your role as a manager to schedule introduction video calls for their new employee to meet people around the company.

Junior employees might be hesitant to reach out too. So treat them the same as new employees. Help them socialize.

🔦 Provide team members with a great documented onboarding process

In a remote environment, the onboarding materials should be documented as much as possible. This investment is absolutely worth it, especially as you scale the organization.

Benefits of a good onboarding process:

• They’ll appreciate the initial support
• It will help them ramp up and be productive in their role quickly
• Offloads responsibility from other employees to help get an employee up and running
• Sets the bar of quality and expectations on day one around documentation
• When they find something missing during the process, they can contribute and add value to the organization early on

This is something you and your team should agonize over. It’s really that important. There are always ways to improve the experience, so keep making it better with each new team member that goes through it.

💪 Pair them with a senior team member

Let’s face it, your onboarding will never be comprehensive. Pairing your new employee with someone in the same role will give them an opportunity to ask deeper technical and project related questions that aren’t covered by onboarding documentation.

Additionally, during the interview process, it’s not likely that you’ve uncovered some skill gaps for this new employee. Since you don’t hire solely based on skills alone, this shouldn’t be a problem! But, let’s make sure those gaps get filled.

If you didn’t make those gaps clear during the interview process, make sure it’s known in their first week. You, as their manager, should work with them on a written plan, which will be handed off to the senior pairing with them.

For junior employees, this pairing is especially important to help them become a productive team member without a lot of stress and anxiety.

☑️ Check-in daily for an initial period of time

Think back to your first few weeks at a new job. They’re exciting and also overwhelming. It’s even more difficult when you’re alone at home trying to figure it all out.

Another team member and yourself should check-in daily with the employee for the first few weeks or until there are clear signs that the employee is settled in.

Let me be clear though, “Checking in” doesn’t mean having a formal meeting, making the employee list out everything they’re working on. Instead, it should be a slack message or something very informal that gives the employee an opportunity to share they’re having difficulties with something and need help. A simple, “hey, how are you doing today?” is fine. Don’t be overbearing.

📹 Use video as much as possible

First and foremost, it helps you build a personal connection with the employee. Nothing beats meeting in person, but video is the best alternative we have in remote work.

Additionally, it’s very difficult to understand a person’s frame of mind by just listening and certainly impossible over slack. With half of human communication being body language, seeing your employee over video will help to uncover any issues they might be otherwise hesitant to share.

So, if you sense there is something off, don’t hesitate to ask the employee if they’re alright. If there is, offer up your support.

☎️ Weekly team bonding video call

One of my favorite parts about working at Naked Apartments was having a Monday video call to share our weekend adventures and do “show and tell”.

It’s important to schedule a weekly meeting for small talk and fun, giving people time to connect on a personal level. Work related team meetings (like stand ups) and 1-1s with a manager don’t count.

😂 Setup “water cooler” chat rooms

Your team should be encouraged to have fun talking about things that are not work related. Simulating the “water cooler” is important for morale and creating human connections.

Create #random (or similar) slack channels purely for banter. Use emojis and memes freely (work appropriate of course) to help create that human connection. Encourage these new employees to join and nudge them into conversations if they don’t do it on their own.

🧠 Include them in brainstorming discussions right away

Too often, new or inexperienced employees are left out of brainstorming sessions because of their lack of institutional knowledge. The fear is that they will slow down the team, asking basic questions.

It’s a silly fear, since you’d be missing out on something way more important. A fresh perspective. Invite them in. Let them share their thoughts and they’ll learn something along the way too. You’ll be surprised at what happens, I know I was.

🏝 Encourage them to take breaks and end their day at a reasonable time

Burnout is a big problem in remote work, especially for new and junior employees who are trying to impress their teammates and manager through sheer brute force. As their manager, you need to keep a very close eye on this.

It’s also a good idea to encourage new hires to schedule a vacation in their first 6 months. It sets a good precedence about your values as a company and encourages taking breaks.

During the summer months, you might want to give employees Fridays off (i.e. Summer Fridays) to enjoy the beautiful weather. This forces employees to take time off and recharge. This was especially important for us at Naked Apartments, since the prior months were usually the busiest time of the year for our company.

📅 Set expectations around availability and scheduling

• What time do people tend to work here?
• What does flexible hours mean to this company?
• If someone sends me a slack message when I’m done for the day, do I need to respond?
• How about emailing during off hours?

When you’ve got an all-remote company, there is usually someone working at all hours of the day, because of timezone differences. Setting expectations is important so people can understand when they need to be available, allowing them to fully enjoy their personal time.

In addition, you may want to define overlap time to allow for synchronous discussions (like team meetings). That overlap time should work best for the majority of the team. 2 - 4 hours of overlap worked well for us at Naked Apartments.

📋 Start them on small projects and then ramp up

I get it, you’ve got some big initiatives you want to crank out. Avoid the temptation. Don’t throw a new or junior employee into the deep end. It’s overwhelming starting a job by itself, so don’t make it harder.

Instead, use this opportunity to:

• Build up confidence with some small wins
• Get them accustomed to team processes and workflows
• Provide them time to fill in those skill gaps and learn the institutional knowledge needed to be productive
• This is a great time for a manager to continue to learn an employee’s strengths and weaknesses

😢 Don’t forget to include them

I think this is especially important for companies that have a mixture of remote and office employees. I experienced the pain my team went through vividly when they were left out of events after the acquisition of Naked Apartments by Zillow. Trust me, no one intentionally left them out, but I’m sure it felt that way to them.

Whether it’s an all-hands meeting or an office happy hour, make sure to include them and make them feel accommodated as best you can.

For in-office happy hours for example, schedule a virtual happy hour to share a drink together and celebrate wins. They might miss the physical event, but they’ll appreciate the social interactions.

🤝 Conduct weekly 1-1s

Give enough time

First off, your 1-1s should be longer for these new and junior employees compared to senior team members, since they need more support. I found that an hour a week is usually long enough.

Keep the same schedule

• 1-1s never should be cancelled by you.
• If they cancel frequently with you, dig in to make sure they aren’t having problems

See how they’re doing personally

Make sure to ask good questions to help dig into how they’re adjusting to working from home and their new role in the company.

Develop your employee

Make good use of the time you have with them to discuss a development plan to help them in their career goals and increase their performance. No matter if they’re alone at home or in an office, they’ll love that they’re learning and on a great path.

Adjusting to a work from home lifestyle doesn’t happen overnight. That transition takes time and is not easy, even with all the wonderful information available to us about working from home. The world is in turmoil right now and so are employees. Many of us are feeling uncertain about the future, are lonely, and overwhelmed. Our emotional states are compromised, whether we’re able to admit it or not.

When things are chaotic as they are right now, it’s also incredibly difficult to be a people manager. As a manager, you try your best to keep the team together, productive, and spirits up. The worst thing you can do as a manager right now is to push your team to be more productive. Your team needs emotional attention, not project management optimizations during this pandemic.

So instead, I encourage you to schedule a weekly video call with your team. There is a catch of course. Don’t talk about work during this call. No project or status updates. Don’t share company news. Don’t create meeting notes. Nothing work related. Just chat like a group of friends.

Take advantage of these turbulent times to bring your team closer together and allow them to create stronger relationships with each other. Talk about how everyone is adjusting to their new schedules. Allow people to vent and be frustrated. Support them and encourage the team to support each other. Share weekend stories. If you see something interesting in a team members background, see if they’d be up for a “Show and Tell”. In general, just have fun.

The beautiful thing about this weekly video call is you’ll discover something wonderful, as did I when I built my last company. Each week, you’ll begin to learn new and more personal things about your team members. Things that those team members would have likely never shared in an office atmosphere. You’ll get intimate peaks into their personal world where they’re most comfortable being themselves, not a facade they put up to blend in. It’s amazing.

Companies try to artificially create off sites and team building exercises to emulate building relationships. They work to some degree, but none of those activities come even close to helping build relationships as these weekly video calls did for us.

I implore you, please don’t stress about productivity right now. Seize this moment to bring your team closer together. They’ll be stronger for it once this pandemic is over.

The penalties for hiring the wrong people can be enormous. So it’s critical that you, as a manager, put a great deal of effort into creating and continuously refining your interview process with the goal of finding exceptional people. In the pursuit of finding great people, your focus areas for evaluating candidates will be one of the most important ways to differentiate between the best and worst candidates.

It’s not uncommon for a new manager to focus exclusively on skills required for the position. They craft their tests to determine if the candidate has knowledge in a particular programming language, framework, and other technical areas. As they begin interviewing, they’ll get a false sense of security when they find many people who can’t complete the test, thinking that they’re doing a good job of filtering out poor candidates. Then, one candidate will come along and breeze right through the test. They think to themselves, “Wow, this person must be amazing”. So they quickly hire them.

After a month or so on the job however, the manager gets feedback from their team that this employee is difficult to work with and close minded. Now the manager has got their work cut out for them. They’ll need to work with the employee on their soft skills and try to align them on the team’s values. These rarely change for most people. So not surprisingly, the employee gets upset over they’re managers feedback. And the problems only get worse from there.

Our job as managers is to avoid these sort of problems altogether, by putting together a team that works incredibly well together. Team members should play off each others strengths and weaknesses, while also sharing common values. To accomplish this, you’ll need to instead focus your evaluations on values, abilities, and skills (in that order).

Values are a person’s principles or standards of behavior. For example, a person might value the ability to move quickly or continuously learn new technologies. If your organization is at odds with a candidate’s values, there will always be tension in the relationship. So it’s important that your organization defines and documents its own values. Your team should take those values and rank them based on what’s most important to their groups particular needs. The more values that are aligned, the higher the likelihood the candidate will excel in the team and organization.

Abilities are the things that come easy to people. Their inherent talents. For example, a person can be detailed oriented or inversely able to look at the “big picture”. Certainly, anyone can be detailed or see things from a higher level. But those who don’t have those abilities need to work extra hard to have the same level of quality. Incorrectly evaluating these will result in your time being spent constantly monitoring the consistency of quality for an employee, which is unlikely the best use of your time.

Values and abilities aren’t areas you can question a candidate about directly. Imagine asking a candidate if they value moving quickly. What is the probability they will answer that they value moving slow? Low. Candidates are unlikely to admit they lack an ability. Worse, some mis-aligned candidates will tell you they agree with your values, but will do everything they can once hired to change them. This will require you as a manager to create tests that evaluate on default behaviors, while also assessing their track records. For example, when your organization values continuous learning, you should be asking how they’ve demonstrated it previously. You could also ask them to share resources they’ve recently used to gain a new skill. If the candidate has difficulty coming up with examples, it’s a big red flag.

It’s understandable why managers gravitate towards skills evaluations. They’re straightforward to test on. Just remember though, skills are also the easiest area for an employee to improve upon. Great employees will be excited to take on new learning challenges. All you’ll need to do is allocate some time for them to gain those skills, either in projects or through dedicated time. Evaluating on values and abilities is more difficult up front, but it pays large dividends in the end, making it worth the extra work.