Thursday, Jun 4, 2020
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How to small talk with big bosses

So, you find yourself at the table, in a car, on the airplane or somewhere else with a very senior executive from your organization. If you previously had very little interaction, seize the opportunity to get to know them as a person. This tends to make for a better working relationship.

If you feel a little nervous because you don’t quite know what to talk about, here are a few tips to help the conversation go smoothly.

Firstly, remember this is an opening to make an impression or become an enigma. Choose the first. However, do not confuse making an impression with trying to ‘big yourself up’ or trying to prove your worthiness.

Assume equality. You may be very junior in your position or accomplishments, however, you are no less of a human being. Senior executives put their pants on one leg at a time too. We all share the same universal needs of humanity. We all need to feel significant, a sense of belonging; we crave variety, love and connection. When it comes to being human, we are all equal. There is no need to kowtow.

Relax. If you are uncomfortable, you can make others uncomfortable. Rest in knowing though your worlds may be miles apart, there is commonality in being human. Look for something in common. You may be able to connect on sports, food, travel or family. Most people love to talk about their kids; they love their teams, their pets and their hobbies. Steer clear of religion and politics.

See what you can learn. If you get the chance to sit with someone who has already attained what you strive to accomplish, there is nothing more complimentary than asking questions that show your respect for what they have achieved. Questions like ‘How did you get started?’ ‘What were your biggest challenges?’ and ‘How are things different today?’ can start an interesting dialogue. Plus, you can glean invaluable information while giving the big boss the joy of talking about him or herself. You will probably come away with a better appreciation for your senior, your company and your industry.

Find out their vision. A question like, ‘Where would you like to see the organization in the next five to 10 years?’ may give you a vantage point that is not typically shared at your level. Seeing the big picture can help you to better understand why certain decisions have been made, the needs for the future and the role you would like to play.

Be ready to share how you may be able to help execute that vision if you are asked. Your personal growth should support the goals of the organization.

Be engaging and engaged. Believe it or not, being engaging does not mean doing all the talking. You should do very little talking and lots of listening. Being engaged means listening actively. Put your cell phone away, give your undivided attention and read non-verbal cues. Your boss may not want to talk throughout an entire flight. Allow them to lead the conversation. If they pick up their phone, pull out a book or log onto their laptop, stop talking. They may have planned to do other things during that time frame or maybe they just don’t want to talk. So, pay attention.

Remember, small talk done right can pay big dividends.

My next small group coaching session begins June 7. Send me an email if you would like more information on developing your communication skills for career and business success.


• Kim Welcome is the CEO of Influential Voice. A communication trainer and coach, she assists businesses and professionals to achieve their goals by helping them to develop deliberate, skillful, polished communication skills. Contact: or call 242-225-9013.

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