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Victoria here, Girlboss’ executive editor. 👋 |
Confession: I used to wait in the Google Meet waiting room until I saw at least two other people in the meeting to avoid awkward small talk. 🫣 But now? I don't mind a little "how was your weekend?" chatter, even if things feel a bit awk. Turns out, there's a whole science to getting through small talk with your boss (and maybe even enjoying it?) that doesn't involve white-knuckling through the pain… and smiling through gritted teeth. 😬 And we'll teach you how below. 👇 |
Other stuff the Girlboss team is yapping about on Slack: |
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💼 Job of the day: Needing an excuse to move to Canada? 😉 Aritzia is hiring a Senior Designer, Digital Product Design in Vancouver, to help shape the digital experience for this iconic brand. The perks are pretty sweet, too, including the famous employee discount, an in-office gym, 24/7 wellness support, and 16 weeks of paid parental leave. |
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What’s next is almost here. |
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On July 16th at 1PM ET, beehiiv is going live with a look at the future of publishing, audience growth, and digital business. |
What started as a newsletter platform has evolved into something much bigger: a place where creators and brands can grow, monetize, and own their audiences without stitching together half the internet to make it work. |
The next chapter starts live at the Summer Release Event. |
Join us to see what’s coming next. |
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How to Make Small Talk with Your Boss (Without It Being Painfully Awkward) |
The dilemma: “How do you make small talk with your supervisor without it being awkward? I've been working with him for five months now, and I will say we've gotten less awkward, but there will still be awkward moments when I don't know how to continue the conversation. Help!” |
The answer: Melody Wilding, an award-winning executive coach, keynote speaker, and author of Managing Up: How to Get What You Need from the People in Charge. Check out her free on-demand training course, 5 Steps to Speak Like a Senior Leader. |
POV: You log on to a meeting 15 minutes early, hoping to knock out some emails. Your manager joins, and now it’s just the two of you. You ask how their weekend went and exchange pleasantries. But then there are still ten minutes on the clock, and it's already feeling capital-A awkward. 😖 |
Whether it's that pre-meeting dead zone, a shared elevator ride, or an unexpected few minutes together in the hallway, here’s how to turn small talk with your supervisor into something valuable, and dare I say, enjoyable?! |
🦜 Whip out a good opener |
Often you feel weird about the exchange because you were caught off guard. So have a few conversation starters in your back pocket: |
Reference a project you're both on: “So, are you feeling good about where [project] is heading?” React to something happening in the office or industry: “Did you see that article about [trend]?” Loop back to something they mentioned before. “Hey, how did things with [client/stakeholder/situation] turn out?” |
😶 Keep silence at bay |
Most people default to nervously rambling when a conversation hits a quiet patch. Flip it and pose a follow-up question to your boss so they continue carrying the conversation. |
Say they mention they just got back from a work trip. You might ask: |
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🫳 Drop a detail about yourself |
Small talk can be a great opportunity to shape how your boss sees you. When they share something, bridge to a quick, relevant detail about your own results or expertise. |
For instance, “That's such a good point. I ran into something similar when I was leading the product rollout. We ended up [brief result], which was huge.” |
🍝 Pepper in the personal |
Not every exchange has to be about work. A good rule of thumb: aim for 80% professional, 20% personal. That 20% is what makes you a human being to your boss, not just a direct report. |
If they mention they tried a new Italian restaurant, you might add: “Oh, I love that spot. Have you been to [another place in the next city over] yet? It’s fantastic.” |
Small talk is where bigger career growth is built. Having a manager who advocates for you and pulls you into high-visibility opportunities happens a few minutes at a time. |
Got a work problem you need help with? Drop it here, and the answer to your question could be featured in an upcoming newsletter. 📬 |
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What Team Girlboss has been loving lately. |
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💎 Jenny Bird’s Summer Sale is on now, with 25% off select styles. Executive Editor Victoria has her eye on this mixed metal chain anklet. How gorgeous would it look with a sexy strappy sandal and a handkerchief-hem midi skirt? Swoon! |
🌚 For the girlies who wake up sweating even with the AC on full blast—this Petite Plume pajama short set (in the cutest floral pattern) will be your new go-to. It’s made from 100% Pima cotton in a finer, breathable weave that doesn’t wrinkle or pill, so you stay cool while you snooze.* |
✏️ Your hunt for the perfect lip liner stops here. Social and Editorial Intern Alicia swears by this one from Make Up For Ever in Endless Cacao—it glides on smooth, blends like a dream, stays put, and the precise, sharpenable tip means zero feathering. |
⚽ Want to dress the part of a World Cup fan without looking like you're literally headed to the stadium? Nuuly's Summer of Soccer collection has vintage jerseys, reworked kits, and one-of-a-kind upcycled pieces (including finds from Depop seller Zain the Goat). |
🏴☠️ Pride Month may be over, but we’re still celebrating by watching all of the great queer TV shows you recommended! So many of you suggested Our Flag Means Death, an HBO show about a pampered aristocrat who abandons his life of privilege to become a pirate in the early 18th century. |
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