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Writer's pictureMr Money TV

Sip Sip Hooray! Career Advice You Missed from Our Live Session!


Two men drinking stout.
Peter & Frankie cheering with the crowd.

Two weeks ago, we teamed up with Guinness for an incredible live event, where we dove deep into workplace dynamics and offered career advice tailored for new employees and fresh graduates. From relationship-building strategies to managing expectations with your boss, this session was filled with actionable tips that you can apply right from day one on the job. Here’s a summary of the key points discussed:


Guests in the event
Mr Money TV audience enjoying the event!

Building Trust in Your First Month on the Job

For fresh grads, the emphasis was on establishing trust as the foundation for a strong relationship with your boss. To kickstart this, one critical approach is to make a positive impression within the first month:


  • Showcase Who You Are: Use the shortest time possible to demonstrate both your professional skills and your personality. Don’t be afraid to let your bosses & colleagues know what kind of person you are because at the end of the day, they’ll trust someone they know rather than not.


  • Engage with Your Boss: Fresh grads tend to be quiet and reserved, but open conversations with your boss can make a world of difference. Help them understand your thought process and build trust by sharing how you approach tasks.


  • Be Transparent About Weaknesses: Don’t hide your areas of improvement. Instead, ask quality questions and focus on learning from feedback. In contrast, try to avoid boasting about what you ‘can’ do as well! Imagine yourself in a situation where you’ve constantly mentioned something you can do but end up failing. It will only decrease the trust people have in you.


  • Bond Beyond the Office: Sharing a drink (responsibly!) can improve workplace relationships significantly. When alcohol is involved, we tend to lower our guards and be more open to expressing ourselves. These are the best times to get to know your boss as a person and understand their values.


Men having a discussion
Audience participation!

Navigating High Expectations Without Prior Experience

A common concern is dealing with bosses who expect self-sufficiency and results usually expected from seasoned professionals. Here’s how we suggested managing this:


  • Clarify Expectations: Avoid basing your perception solely on what colleagues say. Sensationalized information often spreads through office gossip, so focus on feedback directly from your boss.


  • Manage Expectations Proactively: Nearly 80% of success in the workplace is about managing expectations. If you’re assigned a project, inform your boss early on where you may face challenges and seek their guidance. In the end, it also covers yourself if you fail because you’ve already informed them of your challenges ahead of time.


  • Seek Resources: Don’t hesitate to ask what resources or support you can access to improve the process and meet expectations. Without the necessary resources and support, it will be a tough road to thread in your journey of growth.


Happiness & laughter
Laughter & joy from the audience!

Knowing When to Reassess Your Fit in the Organisation

Another question tackled when it’s time to reassess working hard to please your boss or fit into the organization:


  • Align Goals: Within your first five years, it’s vital to explore what kind of professional you want to become. Evaluate if the company’s objectives align with your personal career aspirations. 


  • Question the Value of Your Role: If your current role doesn’t help you grow into that person, it may be worth reconsidering your position. If it does, and you’re simply facing challenges, assess whether the goal is truly unattainable or if it’s something you need to persevere through.


A woman covers her face
Don't worry if you're shy, we got you covered!

Handling Bosses Who Don’t Recognise Your Work

One of the last questions discussed was how to interpret a boss who doesn’t acknowledge an employee’s independent achievements:


  • Understand the Motivation: Sometimes, bosses may feel threatened by employees who outperform them or display strong problem-solving skills. This can be more common in corporate settings where competition is high.


  • Corporate vs. Startups: Unlike startups that value and cultivate talent to solve problems, some large corporations might breed a sense of competition. In these environments, bosses may worry about their position rather than nurturing talent.


A group photo with happiness & joy
Mr Money TV group photo with the audience!

These were just a few of the insightful questions we covered that night. Attendees enjoyed even more off-camera discussions, which provided exclusive insights for those who joined us live!


If you missed out, don’t worry! We recorded & edited the session on YouTube for those of you who feel FOMO! So drop by our channel to watch the video, and give us a like & subscribe to stay notified on future events. Plus, if you comment the number of times we say our tagline, “Sip Sip Hooray!”, you stand a chance to win a FREE exclusive omakase dinner!



Click here to let us know if you’d be interested in future events—don’t miss the chance to be part of our next exciting discussion!




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