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

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

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

Know how to approach management to make a great impression.

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?

“Because they are likely doing the thing you’re aspiring to do in the future,” says Mary Ryan, associate director of The Hodges Leadership Center for MBA Programs, at UNC Kenan-Flagler Business School.

Well played, Mary.

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!

“If you see a company leader out and about, introduce yourself, including a 30-second description of who you are and what you do,” says Deborah Scaramastra, career coach at Discovered Path in Seattle. “If the leader seems open to chatting, take a few minutes to ask some questions, and if it's going particularly well, ask to schedule a 15-minute follow-up to learn more.”

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

“Don't approach them in an awkward way, such as by interrupting a hallway chat or—holy Moses—in the bathroom,” warns Scaramastra.

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. Alina Basina, global head of talent and human resources at Jobbatical, outlines how this went down for her:

“I was in my early twenties when I was working at Google, and I really wanted to meet Sergey Brin, the co-founder. But I was a nobody in a sea of thousands of super talented employees—until one day, I saw Sergey walking past me and I just went for it! I introduced myself and spoke about my appreciation for the opportunities Google had offered me. From then on, I knew that I could always give a friendly wave hello to Sergey and that he would, at least, have an inkling of who I was.”

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.

“To overcome the tendency to over-talk and appear anxious or not confident, it is critical to have the 'three-minute version' of your message prepared in advance,” says Elizabeth Freedman, executive coach at Bates Communications, a global consulting firm. “Audiences at all levels are overwhelmed with information, so the ability to keep things simple, clear, and short has a far greater impact.”

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,” suggests Susan Gilell-Stuy, a corporate executive coach at Leadership Compound in Mountain Lakes, New Jersey.

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?” recommends Ben Friedman, co-founder of All Set, a Boston-based start-up.

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,” says Scaramastra. “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.

“The worst anyone can do is say no, and the potential upside of engaging with senior leaders is worth the possible rejection,” says Scaramastra.

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

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