4 Important Questions To Ask Your Boss This Year

Ahh, bosses. Either we love them or hate them. Regardless of how you get along with your boss, one fact remains: your career rests significantly in his hands. Collaboration and respect, therefore, must best define your working relationship.

Managing and communicating with your boss at a comfortable level may be a tricky art, but this shouldn’t stop you from getting the most out of him or her. After all, successful people only get what they want when they chase it. More importantly, bosses aren’t just there to tell you what to do. Ultimately, they have the utmost responsibility of developing and grooming the people who will take their place once they move on. And that’s you.

If you’re aiming for greater heights in your career this 2020, consider the following areas you should be asking and discussing with the boss:

1. How is our working relationship going?

This question may sound painfully awkward but remember that an all-star team is always built on the foundations of trust and transparency. If you’ve been reporting to your boss for quite some time, the start of the year is the perfect moment to agree on your working styles and preferences.

Your questions may be anecdotal or suggestive, depending on past circumstances that you felt caused some tension or ambiguity. For most fresh graduates or junior managers who are still struggling to read “between the lines,” here are some questions you can ask your boss upfront:

Are you okay with my pace of work (for example, am I taking too much time to submit reports? Should I speed up?)

Do you feel that I am properly keeping you in the loop with all the project updates?

Do you prefer to be copied in all the emails?

Could you let me know if I’ve been asking too many questions from you?

Should we have a project list discussion every Monday so I can align queries from you on a regular basis?

Remember that the feedback process is a two-way street, so this is also the fitting opportunity to provide feedback to your boss. For example, tell him to be more specific about deadlines if he keeps missing out on this – and tell him that this is disabling you to identify which projects must be prioritized.

You may also raise your concern if you’re an early bird, and he’s the nocturnal type who goes to the office late and goes home late – and tell him that you cannot stay too late in the office because you have post-work responsibilities.

Of course, not all of us will encounter this easy breezy situation. Most established multinational companies espouse this culture of open communication while newbies in the circuit are still catching up.

This is a very sensitive conversation that must be dealt tactfully and gracefully. Make sure to practice your statements, get opinion from friends, and contemplate on the right choice of words before you bring these up to your boss.

2. Where am I excelling? What do you think are my strengths?

What sets successful people apart from the rest of us? They know their strengths. They are obsessively and consciously aware of what they're good at. They make decisions, choose careers, and create events in life based on those strengths.

Unfortunately, most of us aren’t aware of our strengths. I challenge you: list down your 5 self-perceived strengths, ask a friend to list the same things about you, and compare notes. They won't likely match – proof that many of us are poorly self-aware of our strengths.

This 2020, take the time to find out what those career-related strengths are. Your boss, more than anyone else in the office, will know you best. During your one-on-one discussion, ask your boss which areas have you been performing well in.

Have you demonstrated good leadership skills? Then ask for more projects where you can lead more people even if they don’t report to you. Do people often commend you for efficiently organizing office events? Then look into volunteering in projects where you can assert this strength.

Understanding where you’re good at (on top of knowing your areas of weaknesses) can lead you to answers on how to climb the ladder faster: do your strengths match the job position you want? Is this the best company or industry that will appreciate your strengths? Are you happy with the strengths you have today?

3. How can I progress to the next level?

Great bosses will take good care of your career as long as you deliver. But not everyone will be lucky enough to have good bosses who will treat you like their own children. Many bosses will just be too busy for you. Sounds harsh? Millions of people have quit their jobs for the same reason. Don’t be a victim of this.

This 2020, know that progressing in your career requires shouting it out to the universe. If you want to get promoted, get a salary raise, or be rotated to a different department – make sure you vocalize it. Say it to your boss. Make sure he’s aware that your eyes are nowhere else but on the prize.

When you sit down to discuss your new projects for 2020, make sure you tie them all back to your career: what do you get if you successfully accomplish these deliverables?

This question, of course, will give birth to other questions:

What is the company’s process for getting promoted anyway? Will these sales accomplishments be enough to get you a salary raise?

Or do you need to showcase behavioral competencies such as leadership and networking skills?

Who will be part of the deliberations for your promotion?

Think of it this way: asking your boss about your points of improvement will also make her accountable about her promises. If she tells you that you need X, Y, and Z to get promoted, you will always have this “term of reference” to go back to when the promotion season comes. 

4. What’s your plan for me? Where do you think my career could be headed?

Just like Hollywood, your boss is a talent manager and you are his star. You are Luke Skywalker and he is Obi-Wan Kenobi. You are his prodigy, the successor, the next in line. And even if you’re not yet the one (because someone else may be first in line), you deserve the right to be molded to become a productive asset of the company like all employees should. Your boss is ultimately responsible for your learning and development in the company. Likewise, your failure to improve is also his failure.

This 2020, demand your boss to provide a concrete, measurable, and reachable program on how to improve the skills needed for your career. If you’re 27 years old and soon expecting to be promoted with a team of junior managers, how will your boss prove to his own boss that you’re ready to lead a team?

We’re not just talking about sending you to 2-day leadership seminars. Rather, your boss is expected to design a program, with a specified timeline, which trains and tests your abilities to prove that you’re ready for a bigger desk.

No one else in the company is in the best position to make this magic happen, but your boss. In the same way that citizens have the right to demand quality life from their government, you also have all the rights to demand a good career path from your boss. Ask direct questions:

What higher positions can you aspire for if you excel in this role after 2-3 years?

Do you have the opportunity to be rotated to a different department or perhaps another country?

Can she give you an overview of projects in 2016 that will make you understand better your role and value in the company?

I personally believe that there are two reasons why an employee fails to get promoted even when the time is due: his manager failed to develop him, or he was wrongly hired.

Don’t let the first case happen to you. Steer the wheel yourself when you can because there is no one else more responsible about your career but yourself. When you have a boss or a company who has no morsel of interest in developing your career, then you have a very compelling reason rethink about your situation. 

At the end of the day

Your boss is your ally to your success. Believe that there is goodness in every person’s heart and that the desire to bring the best out of people (just like any “parent”) is something that your boss has surely thought about.

But you need to help and guide him as well. You need to assert and vocalize what’s bugging in your mind or what’s beating in your heart. Be fair to your boss and don’t expect him to second-guess every gesture you do at work.

In most cases, he is simply just as busy as you thanks to the projects tasked by his own boss. So say it now or forever hold your peace. The definition of success may just be a word spoken away in your case. Good luck!

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Jonathan Yabut is the Season 1 Winner of the hit Asian reality show, "The Apprentice Asia" and served as Tony Fernandes' apprentice in AirAsia for 1 year. Jonathan today is the managing director of his own marketing & talent consultancy firm (JY Consultancy and Ventures). Dubbed as Asia's worldwidest motivational and business speaker, he has spoken in 15 countries and 28+ cities around the world. To date, he has published 3 certified best-selling motivational books in Philippines, Malaysia, Singapore, Indonesia, and Vietnam. Visit his website www.jonathanyabut.com or e-mail [email protected] for media inquiries and speakerships.