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The Complete Guide to Working Remotely In 2024

Updated: Jan 2

I just talked with my client, John. He’s the only person on his team who works 100% remotely: it’s not his company’s normal culture but they made concessions for him because he was such a rock star candidate (taking a small bow, thank you!). When he scored the job, he was thrilled that they agreed to a remote work option. But now, he thinks being the only person who is not in the office is hurting him. And… he might be right.

“I’m noticing that I’m not being invited to meetings,” he told me. “I’ve been disinvited from at least one meeting. They used to love me. These days, I’m getting a lot of people saying ‘Sooo, John, what do you do again?’”

Remote work has as many pluses and minuses as on-site work. Remote workers tend to get things done faster due to the lack of distractions. They might reclaim five to 20 hours a week that they would otherwise be spending pointlessly in their cars.

But it was clear that John was suffering from one of the pitfalls of being a remote worker, especially in a company with a strong “onsite” culture. He was missing out on the hallway conversations, the frequent “let’s grab a quiet bite to eat” opportunities to bond with his colleagues. Most importantly, he was invisible to his boss.

So how do people like John stay visible, relevant, and competitive?

What to do when starting a remote job

Start 100% in the office for the first three months.

Not everyone can do this. But if you can swing it, I highly recommend you spend your onboarding first 90 days in the office. While you’re clocking in in person, make an earnest effort to get to know everyone, so that they progress through the “Know You, Like You, Forgive You” pathway. If your colleagues think of you as a random bobbing head on a Zoom background of a Caribbean beach, you’re not going to spring to mind when promotions are discussed. And even if you work your tail off and deliver the goods, being remote can conjure an unfair—but understandable—sense that you’re somehow less involved and committed, and that can negatively impact your performance reviews.

There’s a common sales adage that people buy from people that they “know, like and trust.” In the context of selling yourself as an indispensable employee, if you’re a remote worker, they might know you exist, but they’ve never had the opportunity to Like You. If they never have the chance to Like You, chances are that when you mess up (and we all do), they might be less inclined to trust or forgive you. We tend to give people the benefit of the doubt when we like them.

You can still create very strong trusting relationships if you aren’t able to show your face in the office. And that starts with a solid first 90 Days.

You own your first 90 days.

M. D. Watkins wrote a great international bestseller, a comprehensive guide called The First 90 Days. In it Watkins lays out not only the steps but the outcomes of your first 90 days. But time and time again, I hear from clients that their HR team has a great onboarding program for them.

But just because an onboarding “program” has been prepared for new employees, with shiny presentations and nifty quizzes to pass, doesn’t mean it’s right for you. Those plans are explicitly not personalized, and while they can give you a few clues to your new company’s norms and practices, they’re generally bland, basic, and nonspecific.

My client, John said: “HR had a great onboarding outline for me and I felt great because I completed all items well within the 90 days.” Having been in HR for over 20 years, I can only say this—you are in charge of your own onboarding; not them. Never leave this to HR or your boss or anyone else. You know what you need. You know what you don’t know. Find, or ask for, a mentor if that’s appropriate. Shadow a more experienced teammate. Ask questions that aren’t covered by the shiny video presentation from HR. This is your process.

Walk in lockstep with your key stakeholders.

The goal is to set a cadence with your boss, your peers, and your team (if you have people reporting to you) that makes your role and the goals of your role crystal clear. I call it: Walking in Lockstep with your key stakeholders. You are brand new. You can ask a gazillion questions and ask to meet with people at a regular frequency.

You have three key stakeholders. Your boss, your peers—and your team members, if you are a people leader. People tend to excel in one of these relationships, but flail at another. Be a little self-examining and be honest with yourself about where you might need to make an extra effort if you want those know/like/trust benefits.

Vision of your role.

Have you ever created a vision statement of your role? This is not your job description. It’s the description that is not written. It’s a great idea to actually spell out, in writing, your vision of your job.

Glean this from what you know, what your boss has said, what your peers have said. Write it down in one paragraph. Run it by your boss and ask them if you’re correctly assessing where your role fits in and what it does, with the understanding that things change. Bring them into the conversation so that what you modify incorporates your boss’ feedback. It’s a great way to be sure you’re on the same page, which is especially important for remote workers.

Projects and goals.

Now that you have a vetted one paragraph statement, a vision of your role, list the top three to four projects that are on your plate right now.

Project 1: Complete my Onboarding.

Description of success: Complete all required and requested items on my 90 day onboarding checklist by XX/XX/XXXX.

Current status: 25% completed

Project 2: Launch New Asset Library

Description of success: Obtain 100% understanding of and use of the new Asset Library of the marketing team by XX/XX/XXXX.

Current status: 10% completed

Do the same for Project 3 and 4. Now on one page, you have a vision and four top projects. This becomes your Dashboard. Send this to your boss 24 hours before your weekly check-ins as a gauge of your progress. This assures your boss that even if you’re not physically in the office, you’ve got your eye on the ball. It might seem simplistic, but the dividends are real.

Build project plans.

On Page 2, you can flesh out the details of each project. This should feel familiar, like other project management tools that you’ve possibly used in the past. If your boss wants details, you have them ready to provide.


As you complete a project, don’t delete it from your dashboard; just move it to the back of your now growing project document. So when your one year anniversary review comes along, you have a current status report of where you are… and a record of how you did it. Your manager will feel confident that nothing is slipping through the cracks, and will be more inclined to see you as a team player even if your body isn’t physically in the building.

Making an impression in a remote-first role after the first 90 days

What if you’re well beyond your first 90 days? Would it potentially feel a bit odd to start “onboarding” yourself even if you’re well past that first 90 days? Yeah, maybe! And guess what: you should probably do it anyway. Think of it as “rebranding” yourself. The truth is, we do that many times throughout life, and it does work. As soon as you start to speak and question and interact in a different way, people will begin to see you in a different light.

If you’re a remote employee and starting to feel like things are happening without you, that you’re being left behind, I highly recommend that you dust off your first 90 day outline and create a strategy to re-engage.

And once you get promoted into a role of influence, I recommend you figure out ways in which you can engage your remote team members on your team so that they can get the same Know You, Like You, and Forgive You benefits as other in-person employees.

When it’s time to ask for a raise….

Honestly, the worst thing an employee can do is to never ask for a raise. You should get used to doing it, you should be assertive about doing it. And… you should be wise about when and how you do it.

One of the potential drawbacks to remote work is that you might be less prominent in the minds of your management team, simply because you’re not literally in front of their faces every day. Another is the common prejudice that remote workers do less. This can make it especially hard to know when, and how, to talk about a pay increase.

If you’re a remote worker who can physically come to the office, you should plan on doing that when the time comes to negotiate a pay increase. If you can’t swing this in person, definitely do it on video, not in an email or a Teams chat. Your manager will take you more seriously and will also see that you are taking it seriously. Video adds an element of connecting with the other person.

Make an effort if you’re doing this over a video call: make eye contact. Don’t show up in your jammies. Practice what you want to say if you are someone who gets flustered in the face of a zoom screen. Have facts at your disposal—this is one of the reasons for keeping an ongoing record of your completed projects. Demonstrate your strategic thinking by casting the raise as something that will serve the company and not just you personally. And temper your self-advocacy with a willingness to be flexible: make sure your manager knows your salary isn’t the only possible negotiation point—maybe there are enhanced benefits, or a title change, or increased people leadership, or other negotiation points you can leverage.

So when should a remote worker ask for a raise?

  1. When you’ve done something amazing! Timing is so important. Ask for a raise when you’ve hit an outta-the-park grand slam bottom of the ninth 2 outs and your team is down by 3 points. Your manager will be inclined to agree you’ve earned it.

  2. When you have many months, years of documented performance! This is one great reason, beyond staying organized, for you to track your accomplishments continuously.

  3. When the company is on an upswing! Now is the time to ride the wave. If your company just posted strong quarterly earnings and there’s a growth mentality in the air, managers are much more likely to give a warm reception to pay raise conversations.

Mistakes to avoid when asking for a raise (as a remote worker)

These hold true for in-office workers as well, but when you’re remote you often need to be extra attentive. As obvious as these might sound, you’d be amazed at how often managers deal with the following highly avoidable irritants:

  1. Complaining. Don’t ask for a raise because someone else got one and you didn’t. Or stage a drama about how you can’t pay your bills. Or whine that it has been two years and you’ve thought you “should have one” by now. This is guaranteed to annoy most managers and backfire on you. Don’t indulge in public complaining; unfortunately, people don’t like feeling guilt-tripped and they tend to remember unpleasant interactions more vividly than pleasant ones.

  2. Asking When Things Are Bad. Timing is key. Asking for a raise when the economy is down or the company isn’t meeting financial objectives is honestly pretty tone-deaf, and will serve the dual purpose of irritating your manager and making you seem like you don’t understand what’s going on at your company. Oh, and if your organization is laying people off? Read the room; asking for a raise in the middle of a round of layoffs is a great way to put yourself on the drop-kick list. Sometimes your managers genuinely want to give you a raise but cannot get budget allocated for it. Laying people off sucks for managers; don’t make it worse.

  3. Asking in the middle of your annual review. Sounds like the perfect time, right? Wrong! Why? There is a bucket of money allocated during the set review periods and your opportunity is limited when there are many mouths to feed. Managers tend to feel good when they feel they are helping, guiding, or giving employees what they need. Putting them in a corner in the middle of your performance review, when they are unlikely to have the ability to spontaneously reconsider your salary, is counterproductive.

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