#311: English Small Talk with Your Boss | Build Rapport and Credibility

Looking to make a positive impression with your boss but you never know what to say in conversations?

What questions should you ask? What’s appropriate? How can you build a stronger connection?

You’re not alone in feeling anxiety and uncertainty about striking up a conversation with executives at work. 

It’s completely normal to feel a bit intimidated. After all, these are people who often have a lot of experience and hold positions of authority. 

Today, I’m going to show you how simple it can be to start a conversation with your boss, make a positive impression, and even build a rapport that could benefit your career in the long run.

We’ll go through some easy-to-use tips, strategies, and questions that you can use to feel more comfortable and confident in these interactions. Whether it’s at the coffee machine, in an elevator, or during a company event, you’ll be ready to engage confidently and effectively.

So, if you’re ready to turn those awkward moments into opportunities, let’s get started on transforming how you communicate with your senior leaders. You might be surprised at how simple it can be!

English Small Talk with Your Boss | Build Rapport and Credibility

Three Small Talk Tips to Keep in Mind:

Your boss is human.

• He/She has interests, feelings, and thoughts. Start by asking how their day/week is going. 

Keep it heavy on professional, light on personal.

• To keep your conversational interactions work-appropriate, stick to professional topics related to your work, experiences, learnings, or company for most (think 80%) of your conversation.
  
  From time to time, your small talk discussions with senior leaders (think 20%) could focus on establishing a connection through shared interests like podcasts, articles, world events, books, life experiences, etc. 

Embrace brief exchanges. 

• Your boss is busy and may not always have the energy or time to invest in a full-blown conversation with you. Most importantly, they’re human and may also feel the same way as you about striking up a conversation.
  
  Be open to fluctuations in the depth and length of your conversations with senior leaders. 

Step #1: Plan Ahead

You’ll likely have a moment with your senior leader at a conference, at an after-work event, just before you start a meeting, etc. 

When you expect to run into them, it’s useful to think through what you want to share, ask, and communicate. 

In your preparation, consider the following questions: 

• Where will we be? 
• How much time do we have? 
• What is the purpose of the gathering or event? (Why are we meeting?)
• What do they know about me? 
• What topic would be appropriate to discuss?

Most importantly, ask yourself:

What key message would I like to communicate to my boss? Do you want your boss to

• Learn more about your expertise?
• Receive an update on an ongoing project?
• Know more about your motivation/drive?

Once you’ve made notes on these, consider the topics that would be most relevant and appropriate to discuss with your senior leader within a specific context. 

For instance, it would be inappropriate to talk about your kids if it’s irrelevant to the current conversation.

However, if it’s a more social meeting, you might focus more on their hobbies/interests. 

To get the conversation started, here are some common questions that may be useful:

• What did you think about the presentation? Did you enjoy it?
• How is your day going so far?
• I noticed you’re reading X, how is it?
• How was your trip to X? 

Step #2: Relax, Listen & Connect

Sometimes, we can’t always plan out our conversations. We may bump into our boss unexpectedly. 

When this happens:

Relax & Analyze. 

As you smile and greet them, take a deep breath to relax. At the same time, remind yourself of the time and place. 

Then, start by asking how their day is going. 

This is your opportunity to actively listen for interesting bits of information that could help you connect with them. 

For instance, they mention the day has been quite busy due to a project you’re familiar with.

In this case, you may respond with your experience on the very same project.

Or, compliment them on how they handled a particular issue and share why you found it impressive.  

If they happen to mention the day is going well and they’re on their way to pick up their kids from school…

You might mention that your kids are in school too and ask about the age or interests of your boss’s kids.

Listening for and following up on these bits of information will help you find a connection.

The quality of the connections you make will make the conversation more interesting, help you easily build rapport, and ensure you leave a lasting impression. 

Read the Room

A final note here is to always read the room! 

To read the room means to pay attention to the subtle, non-verbal cues that provide information on the energy, emotions, and/or thoughts of others. 

If your boss seems relaxed and interested, keep sharing details and speaking. 

They may show their interest through their body language and questions/responses. 

However, if their responses are curt, short, and/or they’re not paying attention, it’s your sign to end the conversation politely. 

Step #3: End on a Positive Note

When you’re ready to end the conversation, it’s always a good idea to wrap up the conversation on a positive note.

Here are a few great phrases for wrapping up conversations:

• It was wonderful talking to you. I hope you have a great day. 
• Thanks for the great conversation. Enjoy the rest of your day. 
• I hope we can talk more about X soon. Have a good day!
• Thank you for your time. I enjoyed our conversation.

When ending the conversation, it’s always a good idea to connect back to your key message through your actions. 

Example: Maybe you and your boss have a great conversation about a podcast you’ve both been listening to. If your key message was to connect with your boss, you may end with, “I know you have a busy day so I don’t want to take up all your time, but let me know what you think about the next episode — I think you’ll love it!”

This allows you to keep the conversation open and continue to build rapport the next time you speak to your senior leader. 

Sample Dialogue #1: 

Imagine you run into a senior leader you’ve met once before while taking the elevator. 

• You: Good morning Annie, how are you?
• Annie: I’m well, thanks. How are you? 
• You: Great! I am just on my way up to a client meeting to finalize the details of the new campaign. Have you seen the updated draft?
• Annie: Oh! You know, I did take a brief look. The colors look great. How has the client been so far? 
• You: She’s been helpful and gave us free creative rein. I love working with clients like that. 
• Annie: I hear you! It sounds like you enjoy creative projects. 
• You: Absolutely! Well, this is my floor, but I hope we can chat about the project again soon. Let me know what you think of the final draft.
• Annie: Will do. Have a great day!
• You: You too!

In this scenario, I start with a friendly greeting and stick to work-related topics. At the same time, I also reveal a little bit about my work interests. My conversation is brief and I also end on a positive note of connecting with the senior leader again in the near future.

Sample Dialogue #2: 

Perhaps, you meet your senior leader for the first time at a company retreat and decide to make small talk with him/her. 

• You: Hello Greta, my name’s Sue. I just joined the marketing team a few months ago. 
• Greta: Oh, hi Sue. It’s lovely to meet you. I’ve heard good things about you.
• You: Oh, that’s wonderful to hear! Are you enjoying the retreat so far?
• Greta: Absolutely. I always look forward to getting to know everyone in the company and these retreats are great for that. What about you? How are you enjoying your first company retreat?
• You: It’s been wonderful. I’m grateful for the opportunity to meet people who I’ve only seen in Zoom meetings. It definitely contributes to feeling more connected as a team.
• Greta: I’m glad to hear that. It’s exactly the intent. I look forward to getting to know you more throughout the next few days.
• Annemarie: I am looking forward to that as well. Enjoy the rest of your morning.
• Greta: You as well.

In this scenario, I introduce myself to a senior leader and share relevant information about myself. I don’t pepper her with several questions, either. Instead, I focus on responding to her questions and pay attention to when it’s time to end the conversation with a positive note on future opportunities to connect.

After you’ve watched the video, practice what you’ve learned!

Consider these questions:

1. How would start a conversation with a senior leader at an after-work dinner? What would be your key message?
2. What if you run into this senior leader in the break room? How would your conversation change?

You can share with me in the comment section below.

~ Annemarie

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