Impressing your boss, CEO, soft skills, communication, hard skills
SKILLS DEVELOPMENT / 14 December 2016
Caught in the Elevator With your CEO? Tips to Help Impress Your Boss’s Boss
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Gisel Malek
Content Marketer


The clock strikes noon and you are gleaming with joy! It’s time to leave your desk and head over to that new taco stand you’ve been meaning to try! You start walking towards the steel elevator doors, push the down arrow and wait patiently as you catch up on some text messages from earlier in the day. The door slowly opens as you proceed to walk towards the corner of the elevator, hoping to stop for nobody on your way down. You hear that dreadful “ding” and hope that just once you won’t get stuck in a room with ten others. Someone walks in - but not just anyone, the CEO! Your mind starts racing, and you wonder “Should I say something?” Should I just smile and make sure they get off first?” You do know that you want to be engaging and possibly even set up a meeting at a later time to discuss your future, but...silence takes over.


“DING!” You look up and see you have finally approached the lobby and the door slowly opens, painfully slow as if to ask “are you sure you don’t want to take these last few seconds to make an impression...any impression?” But it’s too late! You smile and nod in acknowledgment as the CEO of your company just walked out of the elevator door and turned the corner in the marble lobby. 


Don’t let this happen to you! 

Here are some suggestions to best handle yourself should you ever be stuck in a moving metal box with a high-level executive from your company:


Situation Awareness

You might be in a room with others and tempted to start up a conversation with the CEO. It’s obviously ideal if it were just the two of you, but that may not always be the case. This is not to say you shouldn’t say anything, but definitely strategize what you are going to say and when you bring it up. Timing is everything. 

If he/she is talking to others

Find a moment to chime in (if appropriate) whether it be a smart or funny comment, or to give your opinion. Don’t interrupt the conversation they are having for selfish reasons - it would be seen as an act of rudeness. If you don’t see an appropriate time to chime in, definitely let it pass. It would be better to wait for another opportunity than to force an existing one. But, if you do have the opportunity, just work on your timing. If you are nervous, breathe and try to relax. Think about what you are about to say and make sure it’s what you actually want to say. 

How to successfully chime in on an existing conversation in 2 steps:

1. Use your body language to your advantage. Make it known that you want to be heard by leaning in with your body and making direct eye contact. You may naturally get invited into the conversation if they pick up on it. 

2. Add to the conversation. If you have some information that you think would add to the quality of the conversation, you would be putting yourself in a good position to get included in on the conversation. Or, interject just long enough to introduce yourself and make a good first impression on the CEO letting he or she know you are not shy, care about the company and have drive - all good things to showcase!

If he/she seems to be working:

You may find that your CEO seems to be deep in thought or taking notes. Whether it’s just the two of you or if there are others in there, it is important to not interrupt them if they are preoccupied. However, if you can sense that they would be open to a friendly hello, I would take the opportunity to keep it short and sweet. It really depends on the work that they are doing and whether or not they seem open to a hello. Every situation will read a little bit differently according to the person, so be extra perceptive in these situations. For example, if they are working but say something like, “TGIF!” it would be safe to assume that even though they are busy, they would be open to surface conversation. However, if there is no eye contact being made then it is safe to assume that the situation doesn’t present itself with an opportune moment to catch their attention. 


Get the Conversation Started

The worst thing that can happen is being left with a feeling of regret that you didn’t say anything at all. If you get to the point where you are introducing yourself - follow these best practices to be able to weave into a conversation more easily. 

“Who is your daddy and what does he do?” - Kindergarten Cop

It is important to introduce yourself to him/her and mention what you do at the company. Walk over with a firm handshake and simply say, “Hi, my name is John Smith and I am the Head of purchasing. It’s a pleasure to meet you!” Your CEO will likely reciprocate the salutation and perhaps even ask you a question or two. Most CEOs would love the opportunity to get to know the people that are the backbones of their company. 

“Remember? She’s just human - just like you and me!” - I Love Lucy

The most important thing to remember is that at the end of the day, they are human just like you. No need to get star struck, especially since most of the time they like to know more about the people working at their company and encourage conversation. Getting hung up on the hierarchy difference will only make your executive feel uncomfortable as well, making it more difficult to make a positive impression on them. Speak to them like they are someone you would report to on a regular basis, with confidence, respect, and poise. 

Research is creating new knowledge - Neil Armstrong

You just found out your CEO came back from an exotic vacation and you ask about how it went. They seem excited to talk about it. Score! As a new hire or even someone who has been with the company for an extended period of time, you never know when you will run into the CEO of your company or where. It is a good idea to be aware of what is happening in your company at all times, so should an opportunity arise to meet your CEO, you would be prepared. Taking it a step further and learning more about them and who they are can help as well. For example; reading a book they may have written can make for an excellent opportunity to break the ice. 


Make the Conversation Count

An elevator ride is never a long one and so those 30-60 seconds really matter a lot when trying to have a quality run in with your boss’s boss. Follow these best practices to make the best impact in the amount of time allotted. 

Depending on where you are in the company or what position you hold, it is considered pretty noble to ask for a meeting with the CEO, especially if you have some great ideas or want them to know you are interested in advancing with the company! The meeting can be as formal as in the conference room with VPs or as casual as grabbing some coffee across the street. The point of the meeting is not to advance yourself right away, but to let them know who you are, what you do and where you would like to go. If you are a more senior level employee, you may want to share your thoughts about the department you work in and how you can help make it better. Or, if you are a newer employee, simply, just let them know how much you like the company and your plans for moving up, and you will see how much your tenacity is appreciated. 

It doesn’t hurt to do your homework ahead of time and find out what is happening in your company - in fact; it’s highly encouraged.  If you happen to see your CEO just did a PR piece or was featured somewhere, it would be a wise decision to offer your congratulations or to say something like this: “ I saw your interview with such and such company and found your viewpoint on “X” topic really fascinating.” Not only will they be enlightened to know that their people are really staying connected with company happenings, but you will stick out in their minds, making it easier to ask for that future meeting or, maintain your confidence level for future run-ins.


These tips are directed at people in the workplace. However, don’t exclude yourself if you don’t currently have a job. Having practice working with mentors at companies that are looking to hire can really help with getting your confidence up when it comes to talking to people in higher positions. It’s like with everything else, the more practice you have, the better you will get at it!

If you want even more tips, read here for more great posts!