It’s my first day at a new gig. I’m sweating bullets in a freshly ironed suit, feeling like a lame duck in a pond full of swans. I’ve just been introduced to my new boss, and let me tell you, I was nervous as a long-tailed cat in a room full of rocking chairs.

So, what’s the moral here? When you’re the new kid on the block, it’s easy to feel like a fish out of water. But, trust me, it doesn’t have to be like that.

Why? Because asking the right questions can make all the difference. It’s like having a secret weapon or a cheat code to navigate the perilous asteroid fields of the boss galaxy. It’s about understanding their expectations, their style, and what makes them tick.

You know, the same way you’d take a deep dive into the blueprint of a complex piece of machinery before you start fiddling with it. You’d want to know what each cog and wheel does, wouldn’t you? The boss is that complex piece of machinery.

The Power of Connections

You ever hear that saying, “It’s not what you know, it’s who you know?” I know, I know, it sounds like something your Uncle Joe would say while knocking back a cold one at the family BBQ. But Uncle Joe might be onto something.

When you’re starting a new job, networking is more important than a decent coffee machine – and that’s saying something. This is where our first question comes in: “Who outside the team should I meet?” Sounds simple enough, right? But, trust me, this question is a game-changer.

Let me tell you a story. Back in the day, when I was a greenhorn at a Fortune 500 company, I asked my new boss this question. He pointed me towards Suzy from Accounting. Now, Suzy wasn’t part of our team, and I didn’t directly work with her. But guess what? Suzy knew everything about everyone. She was like the office Oracle.

Talking to Suzy gave me insights into office dynamics that I wouldn’t have got otherwise. She knew who was a team player, who was just there for the free doughnuts, and which departments we could count on for support. Knowing all this helped me navigate the murky waters of office politics like a pro.

So, don’t underestimate the power of connections, folks. Asking this question shows your new boss that you’re not just some lone wolf. It tells them you’re interested in being part of the bigger picture, and you’re not afraid to reach out and connect with others. And believe me, that can make all the difference in the world.

Language of the Leaders

Okay, time for some real talk. Communication in the workplace is like playing a game of telephone. You remember that, right? You whisper something to the person next to you, they pass it along, and by the time it gets back to you, “I like your new haircut” turns into “Buy a new parrot.” Yeah, it’s a mess.

So, our second question to the new boss should be, “How do you prefer to communicate?” You’re not asking this to get brownie points, folks. It’s about understanding their style and adapting to it. Maybe your boss is a face-to-face kind of person, or maybe they prefer email updates. Heck, they might even be one of those Slack junkies.

Let’s jump into the time machine for a sec. One of my first startup gigs, I had this boss, let’s call him Dan. Dan was a great guy, but boy, he hated emails. If you sent Dan an email, it would just disappear into the void, never to be seen again. But get him in a room for a five-minute chat? Man, you could conquer the world.

If I hadn’t asked Dan about his communication preference, I would have been shooting emails into the ether, getting frustrated, and probably knitting myself a nice little anxiety blanket. So, do future you a favor and get clear on this from the start.

Remember, communication is the key to success – in your job, in your relationships, hell, in life. Speaking the language of your leaders isn’t about losing your voice. It’s about making sure your voice is heard.

Rhythm of Feedback

Alright, alright, alright. Now that we’ve got the communication thing down, let’s talk feedback. It’s like your mom telling you to clean your room – you might not want to hear it, but it’s necessary. So, the third question to ask your boss is, “How can we establish a regular feedback cadence?”

Feedback, my friends, is the breakfast of champions. It’s the compass that keeps you sailing in the right direction. Without it, you’re just a rudderless ship, bobbing aimlessly on a sea of uncertainty. So, don’t shy away from it. Embrace it.

Let me tell you a story. When I was just a rookie in the corporate world, I had this boss who was like a silent movie – zero feedback. I’d deliver a project, and all I’d get was a nod. Nada else. Was the nod good? Bad? Did it mean ‘great job’ or ‘you’re on thin ice, buddy’?

I finally mustered up the courage to ask for more substantial feedback. I was expecting a torrent of criticism, but instead, I got constructive insights that helped me level up my game. I learned that feedback isn’t a personal attack, it’s a growth opportunity. It became my secret weapon to climb up the corporate ladder faster than Spiderman scales a skyscraper.

So don’t be that guy or gal who’s afraid of feedback. It’s your road map to improvement, your ticket to the big leagues.

Remember, the path to greatness is paved with feedback. Be brave, ask for it, and let it guide you to your ultimate potential.

Being the Team’s Superhero

So, you’re all settled in, you’ve got the lay of the land and you’re getting the feedback you need to level up. But are you really contributing to the team in the best way possible? That’s where the next question comes in, champ. You need to ask your boss, “How can I best support the team and add value?”

Being the superhero isn’t about leaping tall buildings in a single bound or shooting webs from your fingertips. It’s about using your unique talents and skills to add value to the team. To be the superhero, you don’t need a cape, but you do need to know where you fit in.

Let’s take a trip down memory lane. When I joined my first startup, I was a jack-of-all-trades in a team of specialists. I could do a bit of this, a bit of that, but I wasn’t sure where I fit in. I felt like Robin in a team full of Batmans – useful, but kinda out of my depth.

So, I went to my boss and asked him that million-dollar question. He told me something that’s stuck with me till this day. He said, “Geoffrey, you’re not here to fit into a box. You’re here to create your own.”

That was my eureka moment. I realized that being a jack-of-all-trades was my superpower. I could bridge gaps, I could understand different perspectives, I could translate tech-speak to marketing lingo and vice versa. I added value by being the glue that held the team together.

So don’t just aim to fit in, strive to stand out. Find your superpower, and use it to take your team to the next level.

Walking in the Boss’s Shoes

Ever wondered what it feels like to be at the helm, to make the tough calls, to steer the ship through a storm? If you have, then you’re already one step ahead. Asking your boss, “What would you do if you were in my position?” is a powerful way to understand their perspective, and it can open up a world of insights.

Now, you might be thinking, “Geoffrey, why would I want to put myself in my boss’s shoes? I’ve got enough on my plate!” And I get that, amigo. But here’s the thing: understanding your boss’s perspective isn’t just about empathy – it’s about strategy.

Years ago, I worked with a boss who was a tough nut to crack. Seemed like he lived on a different planet. Mars, maybe. We just didn’t see eye-to-eye. Finally, I plucked up the courage to ask him that question. “What would you do if you were in my position?”

His answer? He wouldn’t have done anything differently. But he explained why he had made certain decisions that I had disagreed with. His reasons made sense when I looked at things from his perspective. Suddenly, Mars didn’t seem so far away.

That question didn’t just help me understand my boss better. It made me a better leader. I learned to look at problems from different angles, to consider different viewpoints.

When you ask this question, you’re not just trying to get into your boss’s head. You’re showing them that you’re thinking critically, that you’re willing to learn. And that can earn you some serious brownie points.

The Diamond in the Rough

Alright, let’s talk about potential, your potential. Everyone’s got it, but not everyone knows how to tap into it. So, how do you carve out that diamond in the rough? You guessed it. Another question for the boss, “How can I further develop my potential?”

You see, asking this question tells your boss that you’re not just a clock puncher. You’re someone with ambition, drive, and a desire to grow. You’re not just satisfied with doing the job – you want to excel at it.

Let’s rewind a bit. At my first startup, I had a team member, let’s call him Jack. Jack was a sharp guy, but he wasn’t exactly setting the world on fire. One day, he asked me how he could develop his potential. That threw me for a loop, but in a good way. I saw a spark in Jack that I hadn’t seen before.

We talked, brainstormed, and eventually, we figured out that Jack’s strength was in strategic thinking, not day-to-day operations where he was stuck. So, we made some changes, played a bit of job Tetris, and before long, Jack was leading our strategic initiatives.

That question, that moment of ambition from Jack transformed his role in the company. And it taught me an important lesson as a boss: never underestimate the potential of your team members.

By asking your boss how to develop your potential, you’re giving them a chance to mentor you. And believe me, good bosses love that. It’s like asking a chef for their secret recipe – they’ll be flattered, and you’ll get some valuable insights.

So, don’t be afraid to ask about your potential. It could be the question that launches your career into the stratosphere.

Becoming the Better Version of You

Ever looked in the mirror and thought, “I could do better?” Well, guess what, we all have. But the real question is, are you brave enough to ask someone else, especially your boss, “What could I be doing better?”

Listen up, folks. I’m not gonna sugarcoat it – asking this question takes guts. It’s like willingly stepping into the boxing ring knowing you’re about to take a few hits. But remember, the most valuable lessons often come from the hardest knocks.

Flashback to my days in the corporate grind. I was a fresh-faced exec, eager to prove my worth. I thought I was killing it until I asked my boss, “What could I be doing better?” Let’s just say the feedback was a punch to the gut. It stung, and not just a little. But it was a reality check I needed.

It wasn’t about the sales numbers or project timelines; it was about my approach to work. I was so focused on checking boxes and achieving goals that I lost sight of the people behind the numbers. My boss highlighted the importance of empathy, of understanding my team, and fostering an environment of collaboration rather than competition.

I took that advice to heart, and it transformed my approach to work. It was no longer about just getting the job done; it was about making the workplace better for everyone. And guess what, not only did it improve my working relationships, but it also improved our team’s performance.

Asking your boss, “What could I be doing better?” is a golden opportunity for growth. It shows that you’re open to criticism, eager to improve, and committed to your job. It’s a question that can turn you into the better version of yourself.


We’ve explored the 7 stellar questions that’ll light your path to success. These questions aren’t just some random junk; they’re the keys to unlocking better communication, understanding your role, and building a stronger connection with your new boss.

Asking the right questions can be your compass, guiding you through the uncharted territories of new jobs and new bosses. With these questions in your back pocket, you’ll be better equipped to navigate the workplace and, ultimately, shine like the star you are.

Remember, the universe is vast, and the opportunities are endless. Don’t let fear or hesitation hold you back. Embrace the unknown, ask those questions, and boldly go where you’ve never gone before.

About the Author: Geoffrey Byers
Geoffrey is one of the world's foremost Designers. He is also a Serial Entrepreneur, Author, Speaker, and Mad Scientist. Hypothesis-Driven experimentation is his love language.