Workplace Assertiveness: Can We Speak Up When There’s Inequality?

Communication and boundaries with authority figures.

Christine Green
Relational and Procedural Skills
7 min readOct 3, 2024

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Being assertive and setting boundaries at your job can be a challenge. When the boss makes all the decisions with little or no input from subordinates, you might hesitate to speak your mind.

When working for someone other than yourself, you will be limited in what you can communicate and the boundaries you can set without risking negative repercussions.

Businesses are not democracies. Their operation is not based on equality and employee representation is only assured when a labor union exists.

The hierarchy structure of businesses is not necessarily bad, but unfortunately, the inequality allows for the abuse of power.

Corporate executives call the shots. Their accountability is to shareholders, not stakeholders — their role and priority is to turn a profit, which doesn’t always benefit those at the bottom of the ladder.

However, many corporate leaders understand the value of employee input and display empathetic leadership. They know that happy employees are productive and loyal.

Corporations have a Human Resources Department that, at least theoretically, welcomes and handles employee questions and concerns.

Companies that don’t have an HR department must rely on their managers to establish workplace norms and ensure ethical behavior.

Without a designated HR person to go to, asserting yourself can result in a reprimand, or retaliation from your boss even if you make a reasonable request, and communicate it appropriately.

Depending on your boss, unsolicited assertiveness can also result in getting fired.

Assertiveness Also Means Setting Boundaries
Workplace boundaries can be tricky because they range from small and simple to large and complex.

The smaller boundaries can be attempted through direct communication with the co-worker or boss with whom we wish to set a limit.

Explain to your co-worker that your comfort zone is a bit wider than most people’s, and you, therefore, need more distance when having a conversation at the coffee station.

Let your boss know that you are fully committed to your job and don’t mind a few text messages outside of business hours, but your weekends need to be your own and you therefore will not be responding to emails or text messages beyond the work week.

Without assistance from HR or the use of a formal complaint process, trying to set boundaries at work might be unsuccessful.

The extreme of workplace boundary-setting is to quit your job. That might be necessary if you experience sexual harassment or other inappropriate or abusive behavior from a supervisor or co-worker and have no safe option for reporting it.

Can We Ever Be Assertive with Our Boss?
Assertiveness with our superior at work requires strategy and carefully crafted messaging.

Depending on your relationship with your boss and their personality, you might be able to speak your mind, at least to a certain extent.

Start with a small issue and schedule a time to talk. Email your boss to make an appointment. Ask for 10 minutes of their time,and try to stick to that timeframe so that they know you are true to your word.

During the meeting, if you are having a productive conversation that needs more time, acknowledge that you agreed to keep it to 10 minutes and ask if they have the availability to spend a few minutes to wrap things up. You’ll usually be able to sense if you are pushing it or if they are happy to continue the discussion.

The good thing about making an appointment is that it formalizes your communication and will get you better results than an unannounced visit to their office. Your boss will take it more seriously and you are less likely to catch them at a bad time.

Scheduling an appointment can also lay the groundwork for future check-ins, especially with a boss who tends to avoid communication (too busy or always on the go).

Regular interaction with your boss can help you develop a positive relationship with them, which is a good idea even if you don’t like them. Staying in touch helps maintain a connection and can provide clarity about your role. It establishes a format for a future bigger ask.

Practice the delivery of your message, even for a small issue.

It’s important to spend time composing your message. Rehearse the conversation so that you can speak clearly and succinctly. Keep your cool. Being cordial and respectful will more likely get you what you want.

If you plan to ask for something significant (like a raise) schedule a time to talk with your boss that is convenient for them and when you know they will be the most relaxed and receptive.

If you have critical feedback about something in the workplace that you think can be improved, I recommend that you first ask your supervisor if they are open to input.

Deliver your message clearly and maintain a friendly demeanor. Don’t simply compalin or just say what’s not working. Take time beforehand to reflect on the issue and bring ideas for how to fix the problem or make improvements.

Come to the conversation with curiosity rather than simply judgment. Express your concern but be open to the possibility that you don’t know the whole story. Ask questions, keep an open mind, and be flexible. Be willing to change your mind once you are aware of the bigger picture.

If you still have concerns after your boss has provided more information or explained the policy, tactfully share your perspective and offer solutions. Volunteer to help implement the changes you have recommended.

You’ll be more likely to get buy-in if you suggest changes that don’t require much from your boss. If you have ideas that will make life easier for them and you are willing to oversee the changes you will be more persuasive.

Once your boss has made a decision, accept it. Don’t continue to argue. To do so is challenging their authority and it’s not your place. Operating within a hierarchy can be difficult but the structure must be respected. If you offer that respect and work within the chain of command you will be far more successful than those who buck the system. If you’ve ever been in a supervisory position, you will understand this.

How to Ask
Once you are in the meeting and have your boss’s full attention, be direct. Your ask must be crystal clear and succinct.

Say something like, “I’ve been here six months. You know my value after watching me complete several projects on time and to your specifications. I’m here to request a 15% raise.” Then wait.

Don’t keep talking. Don’t say anything else in an attempt to justify the ask.

Do not fill the silence. Wait for their response.

If your boss wants to know more they will ask you. If they open a discussion you can present your case after you hear their first response.

Too often when those with less power ask for something they don’t wait for a response but do too much talking which only serves to let the boss off the hook regarding a direct answer. They’ll let you ramble until you run out of steam. If you continue to talk that clues them into any insecurity you feel about the ask and they might use that against you.

An assertive ask is short and specific. A confident person makes their request and then waits for a response. The waiting is an expression of your assertiveness. By waiting you communicate that you mean business and expect an answer.

That doesn’t mean your boss will respond with a yes or no, but it does position you as a serious self-confident person. It sets the tone in a subtle but unmistakable way.

Assertiveness Role Models
In the video below a candidate is being assertive during a job interview in a popular TV show that aired on September 19, 1970. This is fiction but is probably not far from what some of us have experienced. It was more than impressive for a woman in 1970 to be this assertive with a potential boss.

The character Mary Richards asserted herself to her boss often on the show. In real life, however, you might not be able to assert yourself as successfully as Mary did.

Your boss can make decisions without consulting you. While you may not be happy with their choices you will be expected to carry out their decisions without question.

The boss gets their way 100% of the time — unless they choose not to.

The British TV series The Diplomat on Prime Video features a workplace in the British Consulate office in Barcelona, with a more level playing field. Diplomat Laura Simmonds has a close friendship with her colleague Alba Ortiz. Laura is Alba’s boss, but the two share details of their personal lives and interact almost as equals.

Ortiz often asserts herself to her boss, but when necessary, Simmonds reminds her who’s in charge, and clarifies the chain of command with her decisions and explicit instructions for carrying them out.

The most effective bosses trust their subordinates and interact with them with compassion. Those leaders are self-assured and therefore don’t engage in power-over behavior.

Fans of Star Trek: The Next Generation will remember First Officer Will Riker and other Starfleet officers asking Captain Picard, “May I speak freely, sir?” Picard would always grant the request because he was a confident leader who trusted his officers. He valued their opinions and wanted to hear their experience. He was also humble enough to know that he had blind spots.

Captain Picard was receptive to his team’s feedback but was also a good role model for solid boundaries. He did not tolerate insubordination or inappropriate behavior. He was emotionally mature, as were his officers. Everyone understood the chain of command and skillfully communicated with clarity and respect.

The series was an excellent model of good communication, great leadership and effective management. It showed how hierarchy can work well for those at all levels. Unfortunately, not many bosses have the maturity or the relational skills to manage people as effectively as Captain Jean Luc Picard.

Christine Green coaches those who aspire to be more assertive at 
work and wish to strengthen their boundaries. Learn more

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Relational and Procedural Skills
Relational and Procedural Skills

Published in Relational and Procedural Skills

Essays on essential skills for effectiveness at home and at work. Relational skills like Assertiveness, Boundaries. Equanimity & Conflict Resolution. Procedural skills like Organizational Process & Planning, Facilitation, Decision-Making & Leadership skills that include them all

Christine Green
Christine Green

Written by Christine Green

Skills Coach. Strengthen your boundaries, speak up & be heard, communicate with compassion: https://christinegreen.com/