How to have a good relationship with your boss when you’re working remotely

Four best practices to help you work well with your boss when you don’t see them face-to-face all the time.

What does her Slack message *really* mean?It’s easy to second-guess yourself when your boss pings you. You want to have a good relationship with your boss — but it’s not always the most natural of things. And that difficulty only increases when you’re working remotely.

When you don’t see your boss face-to-face all the time, the room for miscommunication, misinterpretation, and misalignment expands. You can’t read body language. You can’t go tap your boss on the shoulder to ask a question. You can’t even show her with your physical presence that you are, yes indeed, working.

Yet maintaining a good relationship with your boss is crucial. According to Gallup, “managers account for at least 70% variance in employee engagement scores.” You’re less stressed when things are going well with your boss — so you want to be particularly thoughtful about managing that relationship while you’re remote.

The good news is that this is a common scenario faced by 1,000+ managers in The Watercooler, our online community for leaders from all over the world. Based on their conversations, I’ve pulled a few tips on how to maintain a good relationship with a manager while working remotely…

Proactively share progress

For your manager, understanding what progress you are making on your work is surprisingly opaque. Your manager is often juggling quite a few tasks — be it working with a client or negotiating a partnership — and they want to know what you’re working on ideally without having to hover, check-in with you constantly, be “Big Brother” about it. As emphasized by leaders in The Watercooler, this desire to know what you’re working on is only heightened when you’re remote.

To help shine a light on this for your manager, proactively share as much detailed progress as you can. This can come in the form of writing up a bit more granularly in your bullet points in your weekly summary about the project. Or it can come in the form of you even volunteering that you send her a daily summary of what you accomplished that day. Helping your manager understand the results you’re achieving brings them a ton of ease and peace of mind to their job.

Play detective about their working style

Working well with someone has a lot to do with understanding how they like to work. What are their preferences and habits? What’s the way they’re used to having things done? As a remote employee, not seeing your manager face-to-face, it’s very easy to unintentionally annoy your manager or do something that isn’t within their zone of what they’d prefer. When you know their working style, you can better calibrate from afar how to communicate with them, work with them, and deliver above and beyond what they expect.

To get a sense of their working style, here are some questions you can ask them:

  • What do you value most in a coworker?
  • Who in the organization do you admire, and why?
  • Do you like time to think something over, or do you prefer to talk about it right away?
  • When do you not like to be interrupted during the day?
  • Are you a morning, afternoon, or a night person?
  • Is there anything you feel like you might be a little more particular about than most?
  • What, if anything, worries you or keeps you up at night about the company?

Try asking one (or more) of these questions during your next one-on-one conversation, when your manager asks you, “Do you have any questions for me?”

Rigorously clarify expectations

Arguably the most challenging part of any working relationship — regardless of if you’re remote or not — is to get on the same page in terms of expectations. Do you know what is expected of you, and does your boss know what is expected of her? Often times, when you’re both in-person, these expectations can be hashed out over time: You listen, observe, learn, ask others around you, and pick them up. But when you’re remote, because of limited in-person interactions, those conversations might not come up as readily. Accordingly, it’s imperative for you to ask questions that clarify, uncover, and confirm what these expectations are.

Here are some questions you can ask your boss to start to clarify these expectations:

  • What things will I need have accomplished this year for you to view me in this role as “successful”?
  • What does quality work look like to you?
  • What should standard working hours be for both of us?
  • What is the best way to contact you during those hours?
  • What form of communication should be used to communicate with you during that time?
  • What’s the expectation of how quickly I should respond when you reach out to me during those working hours?
  • What form of communication do you prefer when there’s a hard topic or conversation? (E.g., In writing, over the phone, video call)
  • If I need your attention on something urgent, what form of communication do you prefer? (E.g., Slack, an email, a phone call)
  • What do you consider “urgent” versus “not urgent”?
  • If I have any feedback for you, how would they prefer you receive it: In writing, over the phone, or during a video call?
  • If I have a suggestion about something, how would you prefer you receive it: In writing, over the phone, or during a video call?
  • If I have a questions, what form of communication should I pose the questions to you? (E.g., In writing, over the phone, during a video call)

One Watercooler member also recommended to have a small cheat-sheet with remote communication expectations with best practices like:

If you are going to be offline to take care of some personal things during the day, please notify your direct team on their Slack channel.

If you are planning to work at odd hours schedule for a few days please let everybody know up-front.

Make time to get to know them — in person or over video

When you work in the same physical location as your boss, the opportunities to build trust and rapport are plenty. You can chat with them over lunch and ask them about their hobbies, or go grab coffee in the afternoon and catch up what’s been going on in their life recently. Even bumping into them in the hallway of the office and giving a friendly “hello” fosters a sense of affinity between the two of you. When you’re remote, those moments of social interaction no longer exist. For managers who are working with remote employees for the first time, this is often a shocking and noticeably absent part of a boss-employee relationship.

In the Watercooler, leaders had some recommendations to make sure you’re still getting to know your manager on a personal level (feel free to suggest them as ideas to implement with your manager):

  • If you happen to live nearby your manager, try quarterly in-person lunches.
  • Once a month or once a quarter, have coffee over video for 30 minutes to an hour to chat about life. (Here are some icebreaker questions if you’re never really sure what to talk about or what to ask your manager.)
    Video is always on for calls (unless there is a tech reason)
  • Take a few minutes to catch up on life during the beginning of a one-on-one meeting.
  • Twice per month, during your one-on-one meetings over video, chat about whatever they want to talk about. It usually covers a bit about work or maybe just catching up on what is happening in their lives.
  • Do video chats instead of just calls. Many Watercooler members recommended this. They often ask that people turn on the video and “it makes a huge difference.”

While never easy, focusing on these four areas as a remote employee can help better your relationship with your boss tremendously. If you want, you can even use this article as an excuse to start the conversation and perhaps try a few of these ideas. (For example, you could send an email saying: “I read this interesting article about working well remotely, and thought we might want to try turning on video more often instead of just doing phone calls…”)

These tips have worked for our Watercooler members — I hope they work for you too.


P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew)

How to influence company culture from the bottom-up (not just top-down)

A better company culture can start with you – not just the CEO.

“Culture starts from the top,” it’s often said.

But is that really true?

Surely, it is easier to influence company culture when you’re at the top. As a CEO, founder, or business owner, people are already looking to you for example and guidance around what’s important within the team. (I wrote a bit about how you can influence culture as a leader here.)

However, being a leader in the company is not required to influence company culture. If you’re an employee or a middle manager and you’re frustrated with the status quo in your company, all is not lost.

Culture has nothing to do with what your job title on your business card says.It has everything to do with your beliefs, words, and actions as an individual.

Culture is made up of people after all — people who decide what artifacts, espoused values and beliefs, and basic underlying assumptions are true for a team. Any one person can influence culture, not just the CEO.

Regardless of what position you hold in the company, here are few ways you can create an environment for the culture you want to take form:

Model what you’d like to be true of your team.

Let’s say your CEO isn’t great about being responsive to emails and showing that she’s listening. If responsiveness is something you think should be a part of your company’s culture… the question is, how well do you respond to your own emails? When in a one-on-one or a meeting with your team, do you yourself do a good job yourself of listening to and responding to others’ requests? Look at yourself, first and foremost, as a starting point for the kind of company culture you aspire to have.

The power of modeling what you’d like your company culture to be is two-fold: (1) You make it known and visible what can be improved. And (2) if things start going well and your colleagues are really loving what you’re doing, someone — the CEO, founder, or business owner — is going to notice. She’s going to say, “Hmm maybe we all should start doing what you’re doing.”

In other words: Show what you’d like to better in the organization — don’t just wait for it to happen.

Dissent is a responsibility.

If there’s something you think could be better in the organization that the team should adopt to improve the culture, speak up. As an employee, dissent is a responsibility. Voice it respectfully, especially when the opportunity to give feedback presents itself. For example, in your last one-one-one meeting, when your manager or CEO asked you what could be improved, did you share a thoughtful answer?

Culture can only be intentionally shifted if it’s intentionally talked about.

It’s important to do this in private — no leader likes to be “blasted” in front of the company about what you think she is falling short of. (You can read more about how to give difficult feedback to your boss here.)

It’s also important to share your suggestion in the context of the team — and not just your own individual interests. For instance, it’s easy to say that you think the culture should be more open, especially around financials, because you think it’d help you better negotiate a raise. But instead, if you can share why transparent financials would help everyone on the team feel more bought on to what the company is trying to accomplish, the likelihood of others embracing what you’re looking to change increases.

Give space, grace, and gratitude to leaders.

It may take time for the rest of your company to catch on to how you’re trying to influence the company culture for the better. You may even get questions or resistance for why you’re doing things a certain way. Don’t be deterred.Understand that change takes time — especially cultural change, not to mention change that happens from the bottom up. Understand that your leaders are juggling many priorities, and that it may take repeated action for them to take note.

You can also thank your leaders in the meantime for the things they do that already reinforce and support the kind of culture you desire as an employee.There’s a lot of talk of the importance of employee recognition — but manager recognition is just as important. Leaders aren’t thanked very often, so it goes a long way to help solidify the culture you’re want to have, when you show appreciation for the things you already think are headed in the right direction.


Influencing culture from the bottom-up, and not just the top-down, is possible. Though, it may be more difficult and take more time to manifest, it’s an important route to seek as an employee or middle manager. If you can slowly yet steadily put energy behind shifting the culture, you not only make things better for yourself, but for others as well.

As an employee or middle manager, a better company culture can start with you.


Improve your leadership through actions – not words

If you’re looking to improve your management style, consider how action-oriented your leadership style is.

The quickest way to improve your leadership skills is to live this phrase:  “It’s not what you say that matters — it’s what you do.”

I observed the truth of this old adage, firsthand, about six years ago.

At the time, I wasn’t CEO of Know Your Team. I was an employee at another company.

As an employee, I remember making a suggestion to our CEO about how we should market a new program…

I’ll never forget how casually it was brushed aside.

I remember asking our CEO a question via email about a new idea I had, and if it was something he’d be open to…

I’ll never forget that he never responded to my email.

I remember pitching a new approach to thinking about our website to our CEO…

I’ll never forget how defensive he got about why things were the way things were.

The dismissal, inaction, and defensiveness said to me loud and clear: I don’t want your feedback. I don’t plan to do anything with it.

We often forget as leaders how much our actions say — or don’t say.

Suffice to say, I never spoke up and offered honest feedback after those instances, going forward.

Studies have found that the biggest reason for why people don’t speak up at work is because they believe it is futile. Employees don’t think anything will happen with their feedback… so they don’t give it.

I am living proof of that statistic.

If you want honest feedback, you must act on the feedback you’ve gotten in some way. Prove to employees it’s worth their effort to be honest with you.

No matter how many specific questions you ask or how well you receive the feedback, what you do with that feedback will always carry more weight than anything else.

“Lead by example” or “Lead from the front” are common sayings we like to read in management books and nod our heads to. But do we internalize and actively practice those sentiments enough?

If you’re wrestling with the questions of how to better retain your employees, how to improve your company culture, how to cultivate more honest feedback from your employees… Action is the answer.


The 3 Key Elements of Company Culture — And Why They Really Matter

Let’s look past the buzzword and define the key elements of organizational culture.

“Culture” has become the ultimate buzzword these days.

Everyone wants to “improve their company culture.” I see the word frequently littered across the headlines of countless of articles, book titles, and conference talk topics. Leaders also seem to talk about it all the time: CEOs say company culture is their first or second most-important priority as a leader.

Yet for as much we seem to talk about it, do we really know what culture is?

If we want to influence our company culture, we have to start with a keen understanding of what culture actually is.

What is company culture, really?

“Culture is the way we do things around here.”

You may have heard this before. It’s how prominent organizational consultants Terry Deal and Allan Kennedy defined culture in the 1980s. Culture is the thing you can’t necessary touch and feel — it’s the invisible binds and unspoken rules that enforce “how people do things around here.”

However, this definition can be insufficient at times. “The way we do things” feels awfully vague and amorphous, especially when it comes to thinking about how to intentionally create a company culture we’re proud of.

As a result, our attempts to influence culture get muddled. We conflate culture with surface-level relics, confusing culture with “Things To Make People Feel Good.” Think ping pong tables and happy hours and free lunches. Sure, those are part of “the way we do things” — but it doesn’t explain why you’re doing those things. Culture includes that why.

Let’s take a look at culture a few levels deeper.

Three levels of culture

Edgar Schein, another prominent organizational scholar, defined culture as having three levels:

Artifacts

This is the level of culture closest to the surface. Artifacts are things you can see, touch, smell. Ping pong tables, happy hours, and free lunches. It’s also the office layout, the logo rebranding you just did, and your company holiday party. This is typically what we think of when it comes to company culture.

Espoused values and beliefs

One level deeper are your espoused values and beliefs. These are the things you think you believe and say you believe. It’s the mission statement you wrote together as a company, the code of conduct that’s in your employee handbook, or the six core company values your CEO talks about during your all-staff meeting.

Basic underlying assumptions

This is the final, core layer of culture. Basic underlying assumptions are the things you actually believe. For example, at Know Your Team, we have a basic underlying assumption that we must be honest, regardless of the personal cost. So when we made a big mistake a few years ago, we proactively shared it with our customers, even it meant risking losing them. Our basic underlying assumption steered our decision-making and how “we do things around here” — ultimately, driving our culture.

Our basic underlying assumptions are the foundation of culture. If we can influence our basic underlying assumptions, we can influence culture.

Why this matters

More often than not, there’s a misalignment between this final layer — the basic underlying assumptions — and the espoused values and beliefs and artifacts. The things you actually believe, versus the things you say you believe and the things you do to show it.

Perhaps the most glaring case has been Uber. A company that no doubt had artifacts as “proof” that they valued their employees — lavish office parties and state-of-the-art offices. A company that had 14 cultural values it touted, including that employees should “be themselves.” And yet the basic underlying assumption persisted: Win at all costs, by any means necessary. We saw this in countless of examples of questionable ethics and sexual harassment issues ignored. At its core, Uber’s culture was rooted in this aggressive, toxic mindset — and that manifested in how they treated their people, regardless of what superficial artifacts or espoused values they trumpeted.

If you’re looking to truly shift your company’s culture, you have to zoom in on this last and final layer: Your basic underlying assumptions. What you truly believe — not always what you say or outwardly show — is what drives your company’s culture. This should be your focus as a manager, CEO or employee.

Changing your company culture is not about just changing the artifacts. Getting beer taps installed in the kitchens doesn’t make your culture more friendly. Nor does building an onsite gym mean your culture all of sudden cares about employees’ health and well-being.

Changing your company culture also isn’t about just changing the espoused values and beliefs. Saying at all-company meetings, “We believe in honesty and transparency” or writing “We believe in diversity and inclusion” on your career website doesn’t automatically make those things true. Changing your company culture is about tapping into the core beliefs of each individual, understanding what their basic underlying assumptions are, and creating an environment where those can be listened to, brought together, and reacted to.

How do you exactly do this? Read How to Influence Company Culture as a Leader.

Until then, I hope we can take a minute to look past company culture as not a cliché — but an opportunity to precise, perceptive lens to examine figure out how to make our organizations better.

If we can understand company culture, we can improve it.


7 ways to prepare for an effective one-on-one meeting with your manager

Got an upcoming one-on-one meeting with your manager? Consider a few of these tips in preparation for it.

Many managers say flat-out that their biggest frustration is when employees are not prepared for a one-on-one meeting.

Yikes, really?

Over the past four years, I’ve heard countless of managers, CEOs, and business owners say a version of this to me:

“During a one-on-one, I’ll ask a question and there’s silence on the other end. Or they’ll use it as a complaining session and it’s clear they haven’t been thoughtful about what feedback they’re offering. The lack of preparation just kills me.”

As an employee, this may be somewhat surprising to hear. We often underestimate how vexing it can be for a manager when we don’t come fully prepared to a one-on-one meeting.

I know I didn’t prepare for any of my one-on-ones, six years ago, when I was an employee. Out of fear, anxiety, and a bit of dread for what the conversation was going to be like, I pushed my impending one-on-one meeting out of mind.I didn’t think about what I wanted to say in the weeks (and days) leading up to it. “Was it really worth putting in the energy to do so? Nah…” I thought to myself. So I decided against it. As a result, when my boss asked me, “What do you think could be better in the company?” my answer was vague and not meaningful.

In the moment, it felt like the safe and comfortable thing to do. But truth is, I only hurt myself. I bungled my opportunity to influence real change. And, I only further frustrated my boss, who was perplexed that I seemed dissatisfied but never vocalized my concerns outright.

Eventually, I left the company. But I dearly wished I’d approached those one-on-one meetings differently — with less passivity and more positivity. I wish I would’ve seen those one-on-one meetings as an opportunity instead of an obstacle. I wish I would’ve seized those one-on-ones as a moment to engage and dig deeper with my manager, instead of using them to create distance and fester in apathy.

In the six years since being an employee, now as a CEO myself, I’ve since learned the power of preparing for a one-on-one. It’s not just managers who should be preparing for them, but employees too.

Knowing what I know now, here’s what I wish I would’ve considered when preparing for a one-on-one meeting with my then boss…

Share what’s been most motivating to you.

Managers crave to know what they should be doing to help you do your best work. After all, a manager’s ultimate job is to create an environment that enables you to tap into your own intrinsic motivation. During your one-on-one, make sure you share what tangibly has been most motivating to you while at the company: What’s been your favorite project? Who was someone you really enjoyed working it? Why was what you were working on so invigorating to you?

Reveal what’s been draining and demotivating to you.

As an employee, it’s always tough to bring up a critique of the company — especially if it’s about your own manager’s habits and actions. You’re worried it’ll be misinterpreted as “complain-y,” that your manager will take it personally, and that it could affect your career progression. Or perhaps worst, you’ll put in all the effort of sharing your feedback and nothing will happen. While all of those scenarios might be possible outcomes, what we must remember is that if we don’t talk about it, our managers will never know about it. The little things — whether it’s your manager interrupting you during meetings or always asking you to stay late — add up. They gnaw away at your ability to feel energized about your work. If you don’t say something, then who will? When you do speak up and vocalize tough feedback, look to approach the conversation with care, observation, fallibility, and curiosity. It’s a hard, delicate path to travel. But it’s a worthwhile path if you want your work environment to become better.

Explain how you want to stretch and grow.

Your one-on-one with your manager is your chance to let her know how you’d like to be further pushed and challenged in your role (or outside your role). Take time to reflect on what you’d like to improve or work on professionally. Perhaps it’s something more broad, like learning to be more patient and strategic in your thinking. Or maybe it’s much more about gaining a specific skill, such as becoming a better writer. Suggest potential projects for how you’d like to grow in those areas, and see if your manager has any ideas around it. Ask your manager for advice on what books, classes, or people you should be talking to help you pursue the greater learning you’re looking for.

Highlight what you’re grateful for about the company, work environment, or how your manager has treated you.

Giving feedback during a one-on-one isn’t just about zooming in on the bad.It’s the perfect time to point out the good, especially the good things your manager has done or said. Think about what your managers does that your previous manager at another company never did. What are the things you want to make sure she knows you don’t take for granted? Be specific, and say thank you. Not only will it help boost the morale of your manager (who needs the positive support, as being a manager can be a thankless job in some ways), but it helps guide your manager to double down on the things that you appreciate.

Consider what’s been confusing or concerning to you in the company.

Are you concerned that the company is growing too fast, and losing some of its original culture? Are you confused why the company decided to change its vision midyear, when things have been going so well? Consider leveling with your manager about what uncertainty is weighing on your mind during the one-on-one. It’s much more challenging to try to bring it up those questions outside of a one-on-one meeting — so take advantage of the fact you have dedicated time to discuss bigger questions about the state of the company with your manager.

Suggest one thing you see as your greatest shortcoming, and what you want to do to actively compensate for it or improve on it.

During your one-on-one, your manager is bound to share some constructive feedback in an area you could get better. While intimidating at times, it’s a good and helpful thing — and something to prepare for. To help make the conversation easier for you both and to show that you’re actively looking to improve, offer some thoughts yourself about moments you wish you would’ve handled differently. This could come in the form of goals, such as, “I want to find ways to ask more questions when interacting with customers,” or observations of areas you want to strengthening, such as, “I have a tendency to rush some of my projects, and I want to find ways to focus more on quality instead of speed.”

Prepare 3 to 4 questions to ask, to help you better understand how to focus your efforts going forward.

In case your manager doesn’t ask questions that cover everything you’d like to cover, you’ll want to have a few questions prepared. Here are some examples of questions you can ask that’ll help you better understand how you can improve as an individual contributor, and help your manager understand what she can be doing better as well:

  • Do you see any untapped potential in the work I’m doing? An area you think I could be pressing a bit harder in or exploring deeper?
  • What’s been frustrating or confusing about working with me? Where do you see the greatest opportunity for me to improve?
  • What’s the biggest challenge you feel you face as a manager? In what ways can I be helpful in overcoming or facing that challenge?
  • What worries you most about the team?
  • What are you most proud of the team having accomplished?
  • In what ways have I saved you time or made your job easier? What can I be doing to do more of those things?
  • Where do you see the team or company a year from now, and what I can do to help make sure we achieve that vision?
  • What are the biggest challenges you foresee the team or company facing in the upcoming year?

This may feel like a lot. I might recommend taking 30 minutes or so to reflect on some of these items, and even writing out some questions, yourself.

But keep in mind that the more you put into a one-on-one, the more you can get out. While a thirty-minute or one hour meeting doesn’t seem like much, it’s an opportunity to create a better relationship with your manager, to improve the work environment around you, and be plain happier in your job.