Stop Being the Office Doormat: Why Assertiveness Training Changed My Entire Career

The moment I realised I'd been agreeing to impossible deadlines for three years straight was the same moment I discovered the coffee machine had better boundaries than I did.

There I was in 2019, sitting in yet another meeting where I'd just nodded along to taking on four additional projects while my current workload was already making my eye twitch. The coffee machine, meanwhile, had a bright red "Out of Order" sign and wasn't apologising to anyone about it. Brilliant.

Here's what nobody tells you about assertiveness: it's not about being aggressive or turning into some corporate bulldozer. It's about finally treating yourself like you'd treat your best mate - with respect, clear communication, and the occasional firm "no thanks."

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The Australian Way: Assertiveness Without the Attitude

After 18 years as a workplace trainer across Melbourne, Brisbane, and Sydney, I've seen every flavour of communication disaster imaginable. From passive-aggressive email chains that could power a small suburb to meetings where grown adults communicate entirely through strategic throat clearing.

But here's my controversial opinion: most assertiveness training is rubbish. Complete rubbish.

The standard approach treats assertiveness like it's some sort of personality transplant you can download from a weekend workshop. "Just be more confident!" they say. Right. Because confidence is something you can pick up at Bunnings between the snags and the power tools.

The reality? Assertiveness is a skill. Like learning to drive or mastering the perfect lamington recipe - it takes practice, patience, and the willingness to stuff it up spectacularly a few times.

Why Being Nice is Slowly Killing Your Career

I used to think being accommodating was my superpower. Always available, never complained, took on extra work without asking for more money. I was basically the human equivalent of a golden retriever - eager to please and terrible at recognising my own needs.

Then I got promoted to senior consultant and realised something terrifying: my people-pleasing had created a monster. My team expected me to say yes to everything. My clients thought my time was infinitely flexible. Even the office cleaner assumed I'd stay late to let them in because I was "always here anyway."

The wake-up call came during a project review when my manager said, "You know, we never worry about overloading you because you never push back." Not a compliment. An indictment.

Research from the Australian Psychological Society shows that 67% of workplace stress comes from feeling unable to speak up about unrealistic expectations. That's not a communication problem - that's a boundary problem.

The Art of the Strategic "No"

Learning to say no effectively is like learning to parallel park - everyone thinks they're terrible at it, but it's mostly about technique and timing.

I remember the first time I turned down a project that would have required working weekends for six weeks straight. My hands were literally shaking as I said, "I appreciate being considered, but that timeline doesn't work with my current commitments."

The response? "Fair enough. When could you realistically start?"

That's it. No drama, no career-ending consequences, no office politics apocalypse. Just a reasonable conversation between adults.

The secret sauce isn't in the words you use - it's in believing you have the right to use them. Which brings me to my next unpopular opinion: most people aren't struggling with assertiveness because they don't know what to say. They're struggling because they don't believe they deserve to have boundaries.

Dealing with Difficult Conversations (Without Losing Your Mind)

Conflict resolution isn't just about managing disagreements - it's about creating space for honest dialogue before things blow up.

Here's where Australian workplace culture gets interesting. We're brilliant at indirect communication - the raised eyebrow, the strategic pause, the "I'll think about it" that really means "absolutely not." But when it comes to direct, respectful confrontation? We'd rather eat Vegemite with a spoon.

I learned this the hard way during a project in Perth where I spent three months tip-toeing around a colleague who was consistently missing deadlines. My British directness was battling my adopted Australian niceness, and the result was a communication style that confused everyone, including me.

The breakthrough came when I realised that assertiveness isn't about being un-Australian. It's about being respectfully honest rather than politely dishonest.

Consider this scenario: Your colleague consistently interrupts you in meetings. The passive approach is to quietly seethe and complain to your partner over dinner. The aggressive approach is to publicly shut them down mid-sentence. The assertive approach? "I'd like to finish my point, then I'm keen to hear your thoughts."

Same outcome, completely different energy.

The Emotional Intelligence Factor

What's fascinating about working with corporate teams is how often emotional intelligence becomes the missing piece in their assertiveness puzzle.

You can teach someone the perfect script for requesting a deadline extension, but if they can't manage their own anxiety about the conversation, they'll either avoid it entirely or deliver it like they're announcing a funeral.

I once worked with a brilliant IT manager who could negotiate million-dollar contracts but couldn't tell his team when their behaviour was inappropriate. Not because he didn't know what to say, but because he was terrified of being disliked.

We spent six months working on what I call "emotional preparation" - essentially teaching him to have the difficult conversation with himself first. Once he understood his own triggers and motivations, the external conversations became manageable.

This is where most corporate training falls short. They focus on the mechanics of assertive communication without addressing the emotional foundation that makes it possible.

The Workplace Politics Minefield

Now, let's talk about the elephant in the boardroom: office politics.

Every workplace has unwritten rules about who can be assertive with whom, when, and how. The key is learning to navigate these dynamics without compromising your integrity or your sanity.

I've seen too many good people damage their careers by being assertive at the wrong moment or with the wrong person. Usually because they mistook being right for being strategic.

Take feedback conversations. Being assertive with your peer about a missed deadline? Generally fine. Being assertive with the CEO about their communication style during your first week? Career limiting move.

The art is in reading the room, understanding the relationships, and choosing your battles wisely. Sometimes the most assertive thing you can do is wait for the right opportunity rather than forcing the wrong one.

Building Your Assertiveness Muscle

Like any skill worth developing, assertiveness requires consistent practice. You can't expect to go from doormat to diplomatic overnight.

Start small. Practice saying no to low-stakes requests. Express preferences about where to grab lunch. Speak up in meetings when you have something valuable to add.

The goal isn't to become some corporate warrior who challenges everything. It's to develop the confidence and skills to stand up for yourself when it matters.

I tell my clients to think of assertiveness like a muscle - use it or lose it. But also like a muscle, if you try to lift too much too soon, you'll pull something and be worse off than when you started.

The Gender Factor (Yes, We Need to Talk About It)

Here's where things get complicated, and where my experience working across different industries has shown some uncomfortable truths.

Women who are assertive are often labelled as "bossy" or "aggressive." Men who are assertive are called "leaders" or "decisive." This isn't news to anyone who's worked in an office in the last decade, but it's still worth acknowledging because it affects how assertiveness training needs to be approached.

I've had female executives tell me they've been told to "smile more" in meetings where their male counterparts were praised for their "strong leadership style" while displaying identical behaviours.

The solution isn't to avoid being assertive - it's to be strategically assertive. Understanding your workplace culture, building alliances, and choosing your communication style based on what will be most effective, not what feels most natural.

It's not fair. But it's reality. And acknowledging that reality is the first step to working with it rather than against it.

When Assertiveness Goes Wrong

Let me share a story that still makes me cringe.

Early in my consulting career, I was working with a Sydney-based company that was struggling with team communication. Fresh out of my assertiveness training certification, I was convinced that everyone just needed to be more direct.

I encouraged a quiet team member to speak up about their concerns with their manager's micromanagement style. They took my advice, had the conversation, and were subsequently performance managed out of the company within three months.

The lesson? Context matters. Timing matters. Workplace culture matters. And sometimes, the most assertive thing you can do is recognise when the system isn't set up to reward honest communication and adjust your strategy accordingly.

That experience taught me that assertiveness without wisdom is just professional suicide with better communication skills.

The Remote Work Challenge

These days, with hybrid and remote work becoming the norm, assertiveness has taken on new dimensions. It's harder to read body language over Zoom. Email tone is more easily misinterpreted. And the boundaries between work and personal life have become as blurry as a Melbourne winter morning.

I've noticed that people who were perfectly assertive in face-to-face interactions sometimes struggle to translate those skills to digital communication. The same message that would land well in person can seem harsh or demanding in a Slack message.

The key is adapting your assertiveness style to the medium. Over-communicate context in written messages. Use video calls for sensitive conversations. And for the love of all that's holy, pick up the phone occasionally instead of having a seventeen-email debate about project timelines.

The Long Game

After nearly two decades of helping people find their professional voice, here's what I've learned: assertiveness isn't a destination, it's a practice.

There will be days when you nail the perfect response to an unreasonable request. And there will be days when you agree to organise the office Christmas party even though you're already planning three other events and your eye is twitching again.

The goal isn't perfection. It's progress. It's building the skills and confidence to advocate for yourself more often than not. It's creating workplaces where honest communication is valued over polite accommodation.

And sometimes, it's just about being as clear about your boundaries as that out-of-order coffee machine.

Because at the end of the day, the people who respect your boundaries weren't going to be problems anyway. And the people who don't respect your boundaries were always going to be problems, regardless of how accommodating you tried to be.

Your career, your wellbeing, and your sanity are worth the occasional uncomfortable conversation. Trust me on this one.