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Tailor your message

Everyone has a preferred style of communication: Some people are direct while others are emotional; some are casual while others are formal; some prefer a lot of detail while others prefer a high-level overview. Thoughtful (and successful) communicators know the chain of command above them and understand the communication style of every senior leader and executive—all the way to the top of the organization. Read their emails carefully, watch how they communicate to the organization and ask those who interact with them frequently about their preferences.
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Think like an executive

One of the most common mistakes that people make when communicating with executives and senior managers is failing to understand what is and is not important to them. Ultimately, they care about execution and anything that promotes or inhibits the organization’s ability to achieve it. Framing your message in these terms will get their attention and help them reach the conclusion that you are like-minded and focused on business outcomes.
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Prepare for the unexpected

It may sound a bit like an oxymoron, but employees should prepare for a chance meeting with an executive. Executives and senior managers are quite used to challenging the people around them, and if you are not prepared, an impromptu hallway conversation could do more harm than good. It is a mistake to assume that impromptu conversations are casual, because where business is the topic of conversation, it’s a serious discussion, whether it appears to be or not.
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Know the right place and time

An idea, any idea, is not going to come across well if it is delivered out of context or if it is delivered in an inappropriate way. Develop various situation-appropriate messages in advance. The company picnic may not be the place to discuss specifics of a product line you would like to develop, but could be an opportunity to introduce your concept at a high level. Be prepared with details, however; asking next level questions is instinctive for many executives.
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Be yourself

No one comes across as sincere or intelligent when they are putting on airs. Executives generally have pretty good radar when it comes to obvious posturing and people pretending to be something they are not. Sincerity is critical for establishing trust, which is the basis for meaningful communications and relationships with executives. Their decisions are only as good as the information you give them, and executives need to know they can count on you.
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