This happens to be my last year of being in my 20s. Recently, I was haphazardly pulled into a game of ‘We Are Not Really Strangers’ with a close friend I’ve known for more than a decade during our staycation. And as we powered through the prompts, this question was raised, “What part of your life do you miss the most?”. She instinctively reminisced the time when she was 18, young, wild, free, and seemingly unstoppable. When I had the same prompt to answer, it dawned upon me that there was no better time than present day. I had never been more assured, confident, and seemingly unstoppable than now.

There was immense gratitude I felt at that time, to God, to myself, and to the circumstances and opportunities that have led me to where I currently stand in my career. I remember my early days in editorial: feverishly ambitious, anxious, and constantly on the precipice of denotation. Like every wide-eyed fresh graduate, the natural instinct was to feel small, like a fly on a wall, and submissive to every single order barked my way. Pouring in the long hours without fair compensation felt completely reasonable; after all, I was at the bottom of the food chain and needed to pay my dues. At that time, while those years carried many deep-seated insecurities, the experience was also necessary. Many lifelong lessons were learnt, about the industry, about adulthood, and the realities of what made a successful publishing business. However looking back, I did wish those dog days were better spent with a little more assurance and self-worth intact. Most of the time, I was too afraid or too insecure to simply ask.

To sum it all up, the fear of being unworthy ruled the formative years of my publishing career. And it wasn’t until a few years ago, that I started to value my own efforts and achievements sans the need to hear it from my peers or superiors. That changed everything for me — I grew happier at what I was doing, shook off the fear of losing my job, and was bold enough to initiate chats with my boss to talk about my future in the company.  The ball was always in my court, I just didn’t know it yet. And as much as we hope for bosses and supervisors to care for our growth and success, that should never fall entirely on their shoulders nor we should we hold them to this expectation. It’s our responsibility to look out for ourselves and seek out opportunities — whether it be a higher position, moving on to another company, or taking a sabbatical in search of a better self. And no matter the outcome of that, being the one to initiate will keep us moving and better informed to plan our next steps.

Below, three enterprising companies from the tech industry — TikTok, Chope, and Bumble lay down their tips on how to grow and succeed in a company, as well as how to tackle asking the “difficult” questions.

“It’s been quite a while in my current role, what are the next steps to take if I’m thinking of progression?”

Dinesh Balasingam, Chief Business Officer at Chope stresses on defining what you’re looking for before anything else. “When you have a better idea of things like the responsibilities you’re looking to take on, the industry you’d like to explore, or even the markets you’d like to experience working with/in, it’ll help you better determine your next role. And at times, the title doesn’t need to change for that to happen. If you’re in a fast-growing company or start-up and you’re in a more senior position (i.e. GMs, C-suite), it could often mean a slew of new opportunities within your existing role. According to him, setting goals and a timeline would be helpful, especially when your desired role and current skillset might not be a match. “Set a timeline for yourself to get to that point and do what it takes to work towards those goals.” Lastly, create and use your network. He adds: “Having frank conversations with people in similar roles or companies you desire can be extremely helpful to give you a better, and sometimes a less romanticised, idea of what you’ll be getting yourself into. Don’t have someone like that in your circle? Platforms like LinkedIn are a great way to build these connections. Just remember to be polite and respectful of the people whose DMs you’re sliding into!”

“How do I prepare for an appraisal with my boss?”

According to Doreen Tan, User & Content Operations Manager from TikTok Singapore, it’s important to understand the company through and through before diving into your career plans.”Kickstart the conversation by learning more about the company’s long term growth strategy to better understand how you can contribute in your role. Self-evaluate your strengths and possible areas of improvements by having all the necessary facts and figures, including recent achievements and milestones. Focus the conversation on how you can add value to the business, that will be a big win for employers. Don’t forget to express gratitude to your leaders and  be open to feedback on what could have been done better.”

Balasingam recommends having a notebook where you list successes in real-time and also areas you’d like to be better at. “Be vulnerable and self-aware. It’s important to be cognisant of things you could have done better, highlight areas where you’re seeking more mentorship in, and voice concerns you might have about your current workload or work environment in a constructive manner. If 360 reviews aren’t an existing practice, go get feedback from colleagues you work with.” He also recommends speaking to co-workers who you aren’t friends with.”They tend to be more candid and can offer an alternative perspective.”

Lucille McCart, APAC Director at Bumble believes that having a conversation is never wasted. “Remember that sometimes you might ask for something and not receive it straight away — and that is fine. A conversation is never wasted because you have signalled to your employer what motivates you and what is important to you, and those opportunities may present themselves in the future.” She also explains why it’s important to be open in hearing constructive feedback — “Improving your performance and growing professionally requires you to hear what you can be doing better just as much as what you are doing well.”

“What’s the best way to tell my superior that I’m feeling overworked?”

According to McCart, “I think it is really important to just be honest. After such a long period of working from home and under unprecedented circumstances, more and more employers are conscious of the impact this has had on their employees and how they can create a work environment that encourages people to take breaks. Some people are less inclined to take sick days or annual leave while working from home or in lockdown, but time for yourself is crucial for both your mental health and
professional performance.”

For a practical approach, Balasingam suggests providing solutions during the conversation. “Be deliberate when communicating what responsibilities you’ll have to drop or delegate in order to better succeed at the tasks that matter. There are times when it’s less about the workload, but more about lack of training and tools to get the work done in an efficient manner, so be sure to address the right issue.” He also advises seeking input from colleagues or friends in other companies with a similar role, to determine if the workload makes sense. “If it happens to be the norm, ask for tips on how to manage better or gain the experience needed to have it no longer be a struggle.” To make it more official, come up with a timeline to resolve the issue. “Good bosses tend to be aware when their team is overworked, and often it’s being experienced across the board due to factors outside their control (e.g. COVID). That said, it’s important to work with them to determine how long you’ll need to shoulder the additional load. Having a larger than desired workload at times is often part and parcel of a job, but timely resolution to the issue when it does come up, is what will make these difficult times more manageable,” he says. 

Finally, there’s never any shame to approaching the matter. Tan sees this realisation as taking a step forward instead of backwards. “Cut yourself some slack and don’t judge yourself too harshly. Recognise that being candid and honest about your limitations is ultimately a sign of growth and self-awareness.” She concurs with coming prepared with solutions — speak clearly and steadily whilst voicing out your concerns, be mindful to not sound like you are complaining and frame the conversation to ask for guidance.”