When I started my first salaried job, I was excited and thought it would be like my previous work. I started working at 14 mowing lawns and working in fast food. I even had started my own entrepreneurial endeavors. So, at 23, I thought I was ready. I remember my supervisor telling me, three times in the first two weeks, “‘Salaried’ means you stay until the work is done.” At the time, it felt like she must have had lots of lazy hires before me. Now I realize it was also a lesson in culture. She was telling me, explicitly, what was expected in that organization. Beyond the details of my job, she was showing me how to be part of the workplace.

A few years later, I nearly lost a different job because of an email I sent to the CEO. I had carefully laid out a case for something I believed in. It was logical. Detailed. Backed by things he’d said about the organizational values. Citing previous conversations. What I didn’t realize was that it came off as defensive. Blunt, even. I had made no effort to understand the pressures he was under or the bigger organizational dynamics at play. And I had chosen possibly the worst medium possible for such an important communication: email.

Why Logic Without Context Isn’t Enough

My near-disaster with that CEO email taught me that the way disagreement works isn’t always obvious. I’d been on multiple debate teams in high school. I knew how to argue a point. So I approached this disagreement like a debate – here’s my position, here’s why you’re wrong, here are my supporting arguments. But that’s not how organizational disagreement typically works. And unlike in my high school debates, I didn’t seek to get all the information. I just knew my point of view.

I discovered that Stephen Covey’s Habit 5 — “Seek first to understand, then to be understood” — isn’t a theory. It’s real-world tested.

Most workplaces have much more going on than you can see from your individual perspective. And, rather than just pointing out problems, it’s important to first seek to understand the context and constraints you might not be aware of, then collaborate on solutions. Your ability to identify problems can be incredibly helpful. But pointing them out isn’t enough. It’s also important to come with enough curiosity to see if the problem is really a problem, or simply a lack of context.

When you’re new, you’re missing years of context. That decision that seems obviously wrong to you now might make perfect sense when you understand the budget constraints, the previous failed attempts, the client relationships, or the strategic priorities that haven’t been communicated down to your level yet. Learning to ask “help me understand the reasoning here” instead of leading with “this won’t work” can save you a lot of grief. And, as in my case, possibly your job.

Your Last Job’s Communication Doesn’t Necessarily Work in the New Job

It’s easy to assume that once you get the job offer, you’re in. But really, saying “yes” to the job offer is just the beginning. Every organization—whether it’s a 10-person startup, a nonprofit, or a Fortune 500 company—has its own communication culture. How people ask for things. How decisions are made. What “collaboration” actually looks like. And none of that is usually in the onboarding packet.

A comment from leadership coach Kim Nicol recently struck a chord: many young professionals get their first workplace experience in kitchens or food service. In those environments, communication is fast, blunt, and constant. You shout over the noise, move quickly, and expect immediate action. That’s what keeps the line moving.

But that doesn’t translate directly to an office—or a Zoom room.

In startups, things move fast too, but the expectations around communication are murkier.

• Do you just drop a meeting on someone’s calendar? Should you DM them first?
• Do you make a call? Or do you text first?
• What does “ASAP” really mean here? Is it “within the hour” or “by end of week”?

These aren’t dumb questions. In fact, asking them early on can help you avoid the kind of misunderstandings that can quietly stall your progress—or worse, damage your reputation.

Remote Work Makes It Even Harder

The challenge becomes even more complex when you’re working remotely. You miss so many of the subtle cues that help you understand how things really work – who stays late, who grabs coffee together, how the energy in the room changes in different types of meetings. You’re not overhearing the casual conversations that often reveal the real dynamics. This means you need to be much more intentional about cultural learning when you’re remote.

If you’re starting a new job (especially your first salaried one), here are a few things that can help you figure out how the culture really works:

1. Watch and Listen Before You Leap

Don’t assume you know how things are done. Be intentional about observing. How do people communicate in meetings? Are Slack messages formal or casual? When someone needs help, do they send a group message or pick one person? If you’re remote, this takes a little more intentionality—scroll through public channels, read email threads, look at how leaders talk to the team. This quiet listening is cultural gold.

Pay special attention to how disagreement happens. Do people challenge ideas directly in meetings, or do they take conversations offline? How do senior people respond when their ideas are questioned? What language do people use when they have concerns? The difference between how people communicate with peers versus up the chain tells you a lot about hierarchy and expectations.

Watch also for what behavior gets rewarded. And what behavior doesn’t get corrected.

All of this observing does not require you to behave the same way, especially if the communication is confusing, manipulative, or reinforcing systemic inequity. But it does give you clues as to how to play the game in your new position.

2. Ask: “What’s the Best Way to Reach You?”

This simple question shows respect and maturity. Some people love impromptu messages. Others want you to email first, then schedule. I’ve worked with executives who appreciated a heads-up before calendar invites and others who preferred I just “grab a slot.” Unfortunately, there’s no universal answer. Not even in the same office. But asking shows you care about their time and your success. And can help you get things done with less hassle than your co-workers.

3. Get Curious About Decisions

If something surprises you, a policy, a shift in plans, a “no” to something you expected a “yes” on, take a breath before reacting. You could ask yourself questions like:

• What am I not seeing?
• What bigger pressures might be at play?

Better still, ask someone you trust in the organization to give you context. I’ve found it’s important to be truly curious. Not asking with a chip on your shoulder. This humility goes a long way and what you learn will help you long after this job is just a bullet point on your LinkedIn profile.

This is especially important when you think leadership is making the “wrong” decision. Before you craft that email explaining why they’re mistaken, remember that you’re missing context they have – budget constraints you don’t know about, payroll pressures, regulatory requirements, client relationships, strategic priorities that haven’t been communicated down, or previous attempts that failed for reasons you’re unaware of.

4. Be Mindful of Tone, Especially in Writing

According to the 2025 Critical Conversations in the Workplace National Study, 60% of workers say a misunderstood text message has caused them hours of pain and distraction. Email and chat tools are also notorious for stripping away tone. What you think is direct and efficient might read as cold or aggressive. Early on, it’s better to err on the side of warmth and clarity. Add the greeting. Use a kind signoff. And if it’s a sensitive topic, maybe don’t email at all—ask for a quick chat.

When you do need to raise concerns or disagree with something, lead with understanding rather than opposition. Instead of “I disagree because…” try “I want to make sure I understand the full context here…” This approach has definitely saved me from repeating my CEO email disaster.

5. Don’t Let Remote Work Make You Passive

In a physical office, you learn culture by osmosis. You can overhear people in the hallway. You can see how people react in real time. Remote work takes that away. So you have to recreate it intentionally. One approach may be to set up quick 15-minute coffee chats with coworkers. Or possibly ask your manager if you can shadow a few meetings. Tell them you want to understand how the organization “thinks.” This proactive mindset will help you build trust faster than just doing what’s assigned.

Pay extra attention to timing patterns when you’re remote. Do people respond to messages immediately, or is end-of-day normal? Are there unofficial hours when people seem to be offline? How quickly do people start video calls – right on time or do they chat first? These patterns reveal cultural norms and expectations that aren’t written down but guide the work.

6. Understand How Company Size Changes Communication

Small organizations often feel more informal, but that doesn’t mean anything goes. You might message the CEO directly in a startup, but there’s still usually a right way and wrong way to do it. The communication might be more casual, but there are still unspoken rules about respect and decision-making.

Larger companies typically have more established patterns and clearer hierarchies. Information might flow more formally up and down the chain. There might be specific procedures for raising concerns or making suggestions. Neither approach is right or wrong – they’re just different, and it’s important to adapt accordingly.

7. Take the Long View

One of the hardest lessons I’ve learned is that your intent doesn’t always equal your impact. You might mean well. You might even be right. But if you bulldoze or bypass or fail to adapt, you can do real harm. Communication isn’t just about getting your message across—it’s about building a reputation, creating trust, and helping get work done. And that takes time.

The most valuable skill you can develop is learning to read the room – or in remote work, learning to read a video call or Slack channel. Pay attention not just to what people say, but how they say it, who speaks when, and what kinds of responses different communication styles get. These patterns repeat across situations, and once you recognize them, you can adapt your own style to fit what works in that environment. Or, if you don’t want to adapt to the given style because it’s based on systemic inequity, you’ll be able to more shrewdly communicate despite that environment.

You don’t have to get everything right immediately. But being curious about the way your workplace communicates and intentional in how you show up can set you apart in ways that skills alone won’t.

Because how you work with people is just as important as the work you do.

And sometimes, that starts with a simple question: “Hey, how do you prefer to handle meeting invites?”