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The One Conversation That Can Instantly Improve Your Career

Originally published by Lindsey Pollak 27 June 2017

Do you generally prefer emailing, texting or talking on the phone? Do you love it when people write their whole message in the email subject line or does it make you cringe? How do you feel about voicemail? Emoticons? Infographics?

What these types of questions reveal is commonly known as your “communication style,” that is, your preferences about how people ideally should communicate with you. And understanding other people’s communication styles is essential to building successful working relationships with them. But, oddly enough, it’s a topic we rarely discuss.

This is a mistake.

Understanding the communication style of your colleagues, clients and — most importantly, your boss — has a lot bigger effect on your short- and long-term career success than you might think.

There are so many choices for communication —  and so many ways it can go wrong

Communication is a lot like today’s professional dress code: The options have exploded, and there are fewer rules than ever. That means that what’s appropriate depends on your particular workplace, industry norms and the specific person you’re interacting with.

Back in the day, we had just a few choices for communicating — write a letter, send a memo, walk over or pick up the phone. Now in addition to those stalwarts, we have email and texting, plus upstarts like bitmojis and Slack. (You don’t “Slack” at work yet?  You might soon; as a recent article in New York magazine said, “Slack…is likely either as integral to your workday as email or you have never heard of it before.”)

These endless options are a major reason that communication has become so complicated. There is literally no way to guarantee what method another person might prefer.

Not sure how your boss (or any VIP) likes to communicate? Ask!

I recommend becoming the world’s leading expert on how the people important to your career prefer to communicate. This is especially true of your direct boss: There is no better use of your time than knowing his or her preferences.

Sure, you could study her communication for clues to what she likes, but it’s easier and more effective just to ask directly. As Henrik Edberg recently wrote for The Positivity Blog, “Ask instead of guessing. …. This will help you to minimize unnecessary conflicts, misunderstandings, negativity and [wasted] time and energy.”

Cover everything, once and for all, in a style conversation

How exactly do you ask how your boss and other VIPs like to communicate? I recommend the “style conversation” approach. I give 100% of the credit for this concept to Michael Watkins, who wrote about it in his classic book The First 90 Days. He recommends having this conversation at the beginning of any new work relationship.

Depending on your needs and company culture, here are some topics you might want to cover in a style conversation with your boss, an important client or any VIP you come across in your career:

  • What form of communication do you prefer for routine matters? (e.g., face-to-face, phone, email, etc.)
  • What about emergencies? (My assistant, for example, texts me only if there’s an urgent message, like a cancellation or client issue. That means that when I power up my phone after a speech, I don’t have to check my email right away because I know from my texts if anything is urgent.)
  • Can I respond quickly from my phone or do you expect longer, grammatically correct messages?
  • Do you generally prefer a summary or all the background? (I have a client who sends two versions of some emails; one is a summary she calls “TL; DR. The “too long, didn’t read” variant hits the high points for a quick scan, then underneath she adds in the background for those who want more detail.)
  • How often should I communicate routine information or updates? (e.g., as it happens or one weekly summary)
  • What kinds of decisions should I consult you on and which can I initiate myself? For example, can I schedule meetings for you?
  • What is your preference for being copied on emails? Someone shooting for inbox zero might want fewer emails coming in; other managers want to read all the emails, or at least all client communication. Some people don’t read anything on which they are cc-ed.

Don’t make people guess about your preferences

By the same token, if you’re the boss, you will be a much better leader if you tell other people how to communicate with you. Some creative examples I’ve heard lately:

  • One executive with crazy busy mornings prefers status updates sent in the afternoons so they don’t clutter her email box or get lost.
  • One client likes to answer emails on Sunday afternoon, but makes clear to his team that he doesn’t expect a response that day so they don’t feel pressured to interrupt their weekend.
  • A millennial manger I just met schedules one hour of open-door morning office hours on his daily calendar. It provides accessibility to his direct reports, but also saves his day from being interrupted by constant requests.
  • A former boss of mine would become annoyed if someone used a cryptic subject line in an email (making it harder for her to scan messages on her phone), so she shares her preference for descriptive subject lines with new employees right off the bat.

These little quirks are exactly the reason that a style conversation can benefit everyone. If you truly want to be heard, you have to communicate the way someone wants and expects it. And, when you are in the more senior role, you can ease your employees’ jobs by expressing your own preferences.


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