Workplace Red Flags To Look Out For

Alexa Uy, Content Writer Intern

Another one from “Sam”

We all hope for workplaces where we can apply our knowledge, learn new skills and do good work. But how can I look for workplaces that provide this?

“What are some workplace red flags you’ve seen so far?” Now that my circle of friends have all come of internship age during polytechnic or post-junior college, I wanted to see how they were doing at work. To gather intel, I took to Gen Z’s favourite place to share—Instagram story question stickers.

The responses came quickly. “A ‘fast-paced’ environment.” “Unsolicited gossip about other coworkers.” “Bosses trying to get up in your personal business.”

Too often, we find ourselves in gatherings where our friends air grievances about their workplaces, but no one in the group has good advice on how to resolve them. Some of us might be the ones facing issues, but other than complaining, we don’t know how to find other more productive ways to move forward. 

But instead of burying our discomfort, how might we identify workplace red flags, and how might we prepare ourselves to better deal with these situations?

In this article, I share two kinds of common workplace red flags to look out for. Further to that, read on to pick up some tips on how you can better prepare yourself to handle them if and when they come up!

2 types of workplace red flags

1. Unrealistic expectations and boundaries around workload

“It was my first day, and as soon as it hit 12pm, they asked me to work the front counter alone, without any briefing,” my friend A (they/them) shared about their first experience working in retail as a secondary school student.

Even if the job description had proclaimed it would be a “fast-paced environment”, they had expected to at least receive some help navigating the system. “It's almost always a euphemism for ‘we’re going to stress you out and you have to take it’,” they joked.

G, fresh out of an internship, had a similar experience with colleagues disregarding the company procedure of checking with her supervisor before assigning tasks to her. “With many people giving you small tasks, it builds up.” And, as an intern wanting to maintain good relationships with coworkers, she found it hard to say no.

Being an intern, she felt she was a “shared resource”. Thus, she was hesitant to raise it to her supervisors. Still, juggling these tasks with her actual responsibilities was challenging. “I was staying until 9, 10pm to help out with events unrelated to my job scope,” she said.

2. Workplace social norms and interactions that cross the line

Sometimes, “business casual” can get too casual. In a close-knit workplace, it can be “difficult to recognise” when coworkers cross the line from friendly to inappropriate, G said. Often, her boss would text her about topics unrelated to work, both during and outside working hours.

It’s a hard balance to strike. “They’re my friends, but we’re also working together,” she told me. Where would she draw the line? Would doing so make her a killjoy?

The verdict: “It was fun, but it definitely affected my productivity. I had to stay on-task and try to only be informal after work.”

Another respondent, Jeremy, revealed that at work, he would receive unsolicited and unwelcome questions about his relationship status, among other personal questions. Both of my friends felt uncomfortable around these blurring of lines between work and personal life, the formal and the informal; but neither of them knew how they might voice their concerns, or even if it would be appropriate to do so. As the youngest in the workplace myself, I could understand why it might be hard to know how to navigate the new norms of social interaction, let alone speak out when you might be uncomfortable.

One of many responses from “Alewyn”

On the extreme end, a mean-spirited company culture is another issue. Hearing “Alewyn” describe her internship, I got the impression her workplace was not unlike a minefield—she needed to tread carefully. She seemed armed with endless examples of her colleagues and superiors making comments based on others’ appearance, and even race, behind their backs. Even worse, coworkers’ personal issues were fair game for gossip.

One of her higher-ups, for example, made a remark about a certain employee needing a “unique size” while issuing uniforms. This was shrugged off by everyone else, and nothing was done about it—much less the other microaggressions that “snowballed” into a bigger issue, said Alewyn.

“It’s a huge red flag when the leaders of the company ignore and perpetuate this behaviour,” she told me. “It sends a signal to everyone else that it’s acceptable.”

Dealing with these red flags

While definitely easier said than done, here's some tips and lessons I’ve gathered, from the collective wisdom of my friends and I, as we successfully “graduate” from our first internship experiences. At Bold At Work where I interned, I learnt that it is oftentimes important to start with knowing yourself, and starting with that as a foundation for moving forward. 

1. Know yourself and your needs

When you’re feeling stuck, take a step back and reflect on what you want and need from a workplace. As someone with a sensitive temperament, for instance, I know I would crumble in an environment where harsh criticism is a norm.

Looking back on her internship, Alewyn realised that fairness and justice are important values for her at work. This would be something she would consciously look out for at her next workplace. For she knows it is important to her that she work somewhere with leaders who are held accountable for their actions—are aware of their subconscious biases and open to feedback about their shortcomings. 

As for A, while they don’t regret having worked in that retail role, they understand now they work well with some guidance and structure in place, especially as a fresh hire. As such, whether a company has a proper onboarding system and process in place, would become an important question to ask and something that they would look out for, at their next workplace.  

On my part, I am glad for the opportunity for this internship, to have been able to learn more about myself and the work environments I am likely to thrive in, so I can be armed with this knowledge as I navigate my choice of future workplaces. So if like me, you’re just done with an internship, do not miss the opportunity to ask yourself what matters to you at work and what you’re learning about what you most need to thrive in a workplace. You can try out the Bold Values Sorting Activity, and use it as an opportunity to process your internship experience and how these values showed up, or not, at work!      

Once you're in tune with your own needs, you can pivot in the right direction for the next step of your career. Not only that, but you'll be better able to make clear requests and draw boundaries regarding work expectations. 

2. Know your strengths (and points of weakness!) and prepare yourself accordingly

Alewyn’s strength lies in reading the room and adapting her behaviour to make others feel safe. When dealing with “difficult people”, she confided, she deploys an arsenal of psychological tactics like lowering her voice and mirroring others’ body language to quell tensions in the room.  She knows her strengths and she is able to deploy them well in helping her anticipate and handle the workplace situations that arise. 

As for G, she is aware that her trait of being agreeable, will put her in a bind if she is unable to say no when she needs to set boundaries.  

“I try to be accommodating and put my best foot in front of others, but now I know how to be firm and give a hint that I'm busy,” said G, describing herself as a “people pleaser”. She is learning and practising “agreeable” ways of saying no.

It is important to know your own tendencies and plan ahead for tricky situations that may arise, and build up your muscle for how you would handle them!  As with any difficult situation, it could help to call upon your greatest strengths to help you come up with ways to manage it in your own unique way.    

The takeaway

It’s easy to feel powerless in an unpleasant work environment as a part-timer or intern, especially when the problem is deeply entrenched in the company culture, and you feel like you don’t have much say in the matter. 

Still, it doesn’t mean there’s nothing you can do.

Every internship and work experience is a learning opportunity. And the most important thing to take away is understanding more about ourselves, what is important to us, and how that might show up at the workplace.  Armed with this self-knowledge, we can also be prepared, to become a strong advocate for ourselves, whether now or in the future!


Are you an impact-focused organisation seeking to understand what your ideal candidates seek in an employer? Or perhaps you would like to find out more about the 3A survey for employee empathy, to better understand what Good Work really means to them.

Find out more about Bold’s offerings for social impact organisations here or drop us a note at hello@boldatwork.sg to get a brochure!