How to talk to your company’s leaders as an entry-level worker

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From random run-ins to scheduled meetings, this is how to hold your own with company leadership.

They’re older, they’re busier, and oftentimes, the fate of the company you’re working for depends on their decision-making. So as an entry-level employee, why would you talk to leadership in the first place?


Here are a few dos and don’ts for speaking with management to make sure they remember you for the right reasons.

Do: Introduce yourself when they’re free

Don’t: Force it and interrupt them to do so

Whether it’s your department head or even a member of the C-Suite, chances are, you’ll eventually run into a company leader around the office that you’re hoping to talk to. These random run-ins are actually fantastic opportunities to say hello and introduce yourself—as long as they’re not busy or mid-conversation

Forcing an interaction could backfire, so avoid interrupting them at all costs

Do: Express appreciation for working at the company, and what you like about your job

Don’t: Criticize the company or complain about your job

If you work in a smaller office, and you frequently see members of the leadership team in common areas, introduce yourself and make a great first impression.

Since your face time is limited with company leadership, first impressions really count. If you’re positive, that’s the impression you’ll leave. If you complain about workload or something else, you risk being written off as negative.

Do: Be willing to meet with them if they want to learn more about you

Don’t: Be pushy to try and schedule a meeting

If you have the desire to sit down with company leaders, it’s likely you have a lot to say. You might want to suggest changes to the technology investments the company is making, have a proposal for a new product feature, and also want to ask them how they got to where they are in their careers.

As much as you might want to ask them for a meeting and then immediately hop on their calendar when you’re back at your desk to make it so, the better approach is to be interested and flexible. Saying something like, “I’d love to grab a few minutes of your time, whenever you’re available, to learn more about X,” communicates that you’re flexible, sensitive to their busy schedule, and inquisitive (not self-interested).

Do: Be concise and on message

Don’t: Cover everything in one conversation

When you do get a meeting with a company leader, pick one topic and be concise. Company leaders are exceptionally busy people, and may only afford you a few minutes at a time, so they’ll appreciate your efficiency

What’s an easy way to start the meeting? Have a go-to question prepared that you can easily call upon to break the ice and start the conversation flowing.

What types of questions should you ask? If the meeting is to learn more about the company, two example questions are: Why do we do this thing this way? and How did the company make the decision to execute this strategy?

Do: Jump at opportunities for face time

Don’t: Take rejection personally

Senior staff receives hundreds of emails per day and have just about as many meetings. It’s very likely they won’t get back to you at first, but that’s okay.

S/he may be busy or otherwise unable to meet, It’s almost certainly not personal.

In this case, it’s worth reaching out again in a few weeks’ time to see if their schedule has opened up. If they have an assistant, try going through him or her, as assistants usually manage leadership’s calendar.

If they say no, don’t get discouraged. Because of their jam-packed schedule, even if senior leadership does get back to you, they might decline the meeting

And hey, even if they decline the meeting, you’re now on their radar. The door is rarely ever closed.




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