How To Win With Your New Boss Or CEO

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How To Win With Your New Boss Or CEO

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The night before your first day in a new job is scary.  It’s normal not to sleep as well as you normally would and the anxiety sets in about how to make a lasting impression on your new workplace. We travel through life constantly trying to impress our superiors. Whether it be as a child trying to impress our parents, at school trying to impress our teachers or on the field trying to impress our coaches – it is part of our DNA to constantly impress and fit in. In adulthood, it’s all about impressing your boss!

You thought the tough part was behind you when you spent endless hours writing and tweaking your resume and cover letter. Not to mention the preparation and nerves of the interview process which followed. However all that was just pre-work for the hard part, as your journey actually starts on day 1. 

As a CEO myself, I have seen my fair share of new employees attempting to win me over. I’ve seen the good, the bad and the ugly so here’s what I think you should do to make your first day / week / month as smooth and successful as possible!


Be early on your first day

Not just your first day, but your second day, your third day and beyond! Every boss likes punctuality. You don’t want to give management a reason to challenge your commitment within the first week of your new role.  Aim to arrive 20 minutes before your shift starts – This gives you time to factor in traffic, parking, and of course to find the local coffee shop! Walking into the office 15 minutes before your shift begins gives you the chance to scope out the office, find where you will be sitting and locate where the toilets and tearoom are. Once you get to know your colleagues, then you can do the morning catch up around the coffee machine to avoid drawn out chats in your workdays.

Don’t be afraid of your boss 

Pop in to say good morning, if they are on the phone, give them a smile and wave.  Little things like this endear you to your manager.  It is a positive for team culture.  Don’t fear management – they are human too. 

Get to know your boss

You prepared for the interview, right?  You researched the company and the job so that you could impress with your passion. So do the same with your boss! Find something that they are interested in, take notes on what they like and dislike and find out what they like to do outside of work. Don’t be afraid to tap into their personal life because no one is all work and no play. Do they have kids? Do they play a sport? What AFL team do they barrack for?  Do they have a dog? Where do they holiday?  Amongst all of that you will find a connection that will allow natural banter.


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Common courtesy goes far  

At the end of the day, ask the question “what can I do/is there anything I can help you with before I head off for the day”.  Chances are there will not be, however the gesture to help will not be forgotten.  At the end of the first day telling your boss “I really had a great day” is also a compliment that reassures them you are coming back.

Take notes

One of my favourite things to see is when I call a staff member into my office and they come with a notebook and pen. My team know I am going to ramble things off to them and ask about it later so taking that initiative to listen to your boss and listen properly by taking notes is a massive win. Within your first week you will be overloaded with information so what better time to write it all down and read over it later. Make sure they are legible, usable and beneficial.  This will show your boss you are keen and interested and if you reread them overnight you may have questions of clarification that will help your learning and increase the pace in which you retain information.

Stay off your phone and socials

Do not log into your socials or pick up your mobile to text during work hours – you can tell your family and friends about it later. Nothing is going to break your connection quicker than being attached your phone.


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Admit to your faults

With time you will get to read your boss’s moods and their ability to cope with pressure.  Always be a dedicated and honest employee,  if you make a mistake or you forgot to do something it’s OK to admit up to it.  The best thing you can do in this situation is to learn from it and create a to do list, write it in your diary and highlight it off as a personal reward of achievement.

Really get to know your boss

After a week or few months in your new role, start to gather up the confidence to really get to know how your boss likes to work. Learn how they prefer to communicate, whether it be email, phone, or walking into their office. By the time you master these small things you will be dropping a coffee off to them, asking if they want messages taken for the next hour to take pressure off, or even offering to pick them up a sandwich at lunchtime. All these little things tells them are observant!

Seek solutions to problems

Don’t rely on your boss to fix everything when a problem arises. If something has gone wrong and you know about it, take initiative, roll up your sleeves and try to address the problem. Don’t whine about it or try to avoid it, seek ways to solve problems and come to your boss with a solution or no problem at all!

Demonstrate long term interest

Show your interest in the business and where the business is going. You may be young, middle age or at the later years of life but it doesn’t mean you can’t show your commitment to the company. Constantly learn, ask questions and most importantly don’t be afraid to ask for feedback. Overtime you will develop into a valued employee and hopefully you’ll acknowledge your boss as a key support in your growth and development.



Written By
Chris Sacco

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