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Assertiveness in Action - Challenge #5

Better Said Newsletter 004

Read time: 7 min

Topics covered: Assertive Communication, Setting Boundaries, Soft Skills

Welcome back to another edition of the Better Said newsletter! In our last four newsletters, we delved into the world of assertive communication, exploring its importance and how it serves as the cornerstone for effective goal setting. Before we dive into our main topic for today, let's take a moment to reflect on your performance in last week's challenge. We asked you to slow down, ask 3 open ended questions and practice your curiosity.

Quick Reflection

  • Was there a time of day that you found this to be easier?

  • Were there certain people you found this easier with?


Today I've pulled 2 scenarios to outline what needs to be considered and written out example emails and conversations points you can model after.

This week’s challenge (30 min)

Read the scenario and pretend you were in that situation. Role-play how you would handle it.

  • Write out your compass

  • Action steps

  • Dialogue in an assertive tone

Setting the SCENE-ario

Now, let's shift our focus to today's exploration. We'll be examining three distinct workplace scenarios, each presenting a unique set of challenges. While you may not find yourself in the exact same situation, these scenarios are designed to resonate with adjacent experiences that many individuals encounter. The first scenario involves being new to a job and the second addresses discomfort caused by a co-worker.

The common thread running through all three scenarios is the writer's discomfort, stemming from uncertainty about their own desires and expectations. Often, individuals grapple with questions about appropriateness, making assumptions about others' expectations, and neglecting their internal compass. While empathy and consideration are valuable, navigating through life without a steady compass can be challenging. That steady compass is knowing what you want.

As we explore these two scenarios, our approach will be to first outline the non-negotiables – the aspects requiring clarity – and identify areas where compromise may be possible. Subsequently, we'll guide you on effectively and professionally communicating these considerations with the involved parties. This communication should be honest and serve as a foundation for creating positive and constructive outcomes.

Scenario 1 - He kind of follows me

I became friendly with a male cowoker. I am female. He is in a different department but at times we work together and see each other daily. We never were more than friends even though I think at times we both desired to.

Ah the old "will they, won't they".

We had an argument and there was some office gossip about us being more than friends especially since I would about monthly get only him coffee/breakfast. This resulted in our manager pulling me in her office saying he felt uncomfortable and to stop and just not talk or engage with him as necessary work related.

Okay, so you got a clear request from your manager on professionalism.

It’s been a couple weeks but now things are different. He sees me walking and will smile. He seems to email or reach out to me and it is work related but it is almost like he wants to. A few times I am with a group of coworkers and he will come to them and start talking and if I move to a different group he will go to the other group as if he is following me. If he sees me coming he will wait longer than most to hold the door for me. If I see him coming down a hall and go the other way or go down a different hall so will he.

I'm wondering if he got the same message as our writer. If not, there may need to be some clarification so everyone knows what's going on.

He also hangs out at times in places he know he will find me. He will also stand near me and seems interested almost like listening in to my conversations and who I talk to. When we had trash for a work lunch I was helping clean up and he basically insisted in putting plates in the trash and gave me this chivalrous nod and mini bow. I’ve never seen him act this way towards me before.

He's being cute. If he knows it's putting your job at risk, that's not cool. If it's based off assumptions, you need to talk to him.

To me he is acting like he has feelings/a crush on me or wants me to engage with him. I may have feelings for him and I do miss the friendship but I also don’t want to get in trouble and it’s confusing . What should I do?

It's important to take stock. The writer is confused because on one hand, keeping her job is important, don't want to get on the bosses bad side and be unprofessional at work. On the other hand, the flirting is fun. If you aren't sure if you are into this guy, you shouldn't start. It can get messy quick and if your arguement has already sparked issues, it's not a great sart before the relationship and even formed.

Non-negotiables: Your feelings of safety at work. Your job security.

Clarification: Is a friendship or more outside of the workplace you would like to rekindle?

Compass: His behavior at work is putting your job into jeopardy, let's come to a mutual understanding.

Here is how the conversation can go:

You: Hey, could I grab you quickly? I have something I'd like to discuss with you.
Captain Chivalry: Sure, no problem.
You: Listen, I wanted to address our working relationship. I was recently pulled aside by my boss regarding some rumors spreading about us, as well as behaviors noticed by him and our coworkers around the office. He made it clear that this type of behavior is inappropriate, and I was wondering if you received the same message.
CC: [He says his peace]
You: So, moving forward, I want to make sure that we maintain a professional demeanor. I've noticed some behaviors that seem exclusive to interactions with me. I just want to come to an understanding that these behaviors will not continue in the future.
CC: Wait, what do you mean? What behaviors do you feel are inappropriate?
You: I don't want to give an entire laundry list, but just a few examples I've noticed are that you insist on helping me out, like picking up the trash after lunch or holding doors longer than usual. While the gestures are kind, it also makes me feel uncomfortable because I'm very aware that we have eyes on us.
CC: Oh, okay. I'll be more aware of this moving forward.
You: Thanks for being understanding of this.

Scenario 2 - My contract isn't what I expected do I sign it?

I applied for a job, clearly stating my evening availability and desired hours. During the interview, we discussed this, along with pre-booked holidays, and they assured me it was fine. However, upon receiving the contract, it states "zero hours - business needs." When I expressed concern, they mentioned accommodating everyone but cited a small client base for now. They didn't request my holiday dates, and I have until Monday to sign.
  • Worried about unscheduled shifts and the availability of requested hours.

  • Initial understanding that my pre-booked holidays would be honored.

  • The probation period is three months, contemplating whether to sign and hope for the best.

  • Fear of signing and losing control over the assigned hours.

  • Paid for a DBS check, won't be reimbursed until after probation.

  • Currently have another job, but feeling deep into this new one after training.

  • Feeling the company wasn't honest from the start, unsure about the next steps.

Appreciate any advice. Thank you.

Not a great sign if a company is unclear but sometimes companies will have verbal agreements but don't write it down. Sometimes they don't honour them and there is nothing wrong with wanting to get something in writing to protect yourself.

Non-negotiables: Pre-booked holidays need to be honoured.

Clarification: Are my assumptions about the unscheduled shifts and availability of requested hours going to be honoured? Is this a company I should trust?

Compass: I need reassurance that the verbally agreed upon information to be confirmed in writing whether it be in as an amendment to the contract or in an email.


Subject: Contract Discussion

Hey [Recipient's Name],

This is [Your Name]. I've thoroughly reviewed the contract, and I'd appreciate the opportunity to discuss some aspects and phrasing that have raised concerns for me.

I'm available on Tuesday from 10:00 a.m. to 12:00 p.m. and on Wednesday from 9:00 a.m. to 11:00 a.m. Please let me know if either of these times works for you. If not, kindly suggest an alternative.


[Your Name]


You: Hey, thanks for taking the time to address my concerns. I'll keep it brief, understanding your workload. Firstly, during the interview process, we discussed the honoring of my pre-booked holidays, specifically from February 14th to the 23rd. I noticed there hasn't been a follow-up on this, and I wanted to clarify.
[Allow them to respond.]
You: Additionally, my other concern pertains to shifts and the availability of requested hours outlined in the contract. Given my commitment to this team, it's worrisome that the contract allows for my retention without assigning any hours. Would it be possible to amend the contract to include a minimum of X hours per week? While it need not be explicitly stated in the contract, I'd appreciate having my availability documented in some written form to solidify our verbal agreements.
[Allow them to respond.]
I hope, as you navigate through these instances involving concerned Redditors, you gain a deeper understanding of the boundaries of assertiveness. It's fundamentally about safeguarding the respect you hold for yourself and others, while providing sufficient context and information for informed decision-making. Ultimately, you cannot control or compel others to bend to your will; all you can do is carefully consider what holds importance for you and where you choose to take a stand.

Challenge This Week:

Mock the conversation that outlines the boundary in your mind for the following scenario.

Explosive Personality

You have a co-worker who lost their temper in the middle of the meeting. 

Their design was not implemented in the method they envisioned and they explode at the engineers as they give the update and reasoning why it can’t be executed. 

They are rude and downright insulting, calling the engineers ‘useless robots’.

You are one of the more senior players at the table, what do you say?

  • Write out your compass

  • Action steps

  • Dialogue in an assertive tone

As this concludes the last newsletter of the month, our focus will shift to another skill in the coming month, leaving assertiveness behind. However, it's crucial to remember that practicing assertiveness is an ongoing endeavor that extends beyond the current theme.


Thanks for reading issue 004 of my weekly Better Said newsletter. For those of you who are new to my newsletter, Better Said, discusses the following three goals: (1) Elevating crucial soft skills, (2) Reaching career milestones, and (3) Creating ethical leadership.

Here’s how we can stay in touch:

1. You can find me on LinkedIn and on my website,  

2. If you are curious about working with me, you can book a free consultation where I will help you outline your goals and co-create a growth action plan with you whether or not we decide to work together.


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