Jeff, I don’t appreciate you asking me that question

“Jeff, I don’t appreciate you pressuring me into joining happy hour last Friday”

I was stunned and confused. It was my 3rd week in the sales team at Google and I didn’t expect to be scolded like this by a colleague, much less by someone two levels more senior.

But before we get ahead of ourselves, let’s give a little bit of background.


  • Do not run away from awkward conversations. The problem(s) will not magically disappear.
  • Colleagues will respect you more for having the courage to have the awkward conversation, not less.
  • 99% of the time, resolving a misunderstanding through an "awkward" conversation will lead to a stronger relationship between you two
Pro tip: You can comment directly on this post if you have questions or feedback

Onto the debrief

When I was younger, I enjoyed going out. I grew up in Hong Kong so nightlife was a huge part of my adolescent years.

Ah, the good old days

I joined Google Hong Kong back in 2016; I was 24 years old and was one of the youngest hires in the sales team.

I would go out drinking and clubbing on Fridays, Saturdays, and sometimes even Wednesdays (Google search ‘Wanchai Wednesdays’ to get an idea of how the nightlife scene is in Hong Kong), and I would invite my colleagues out as well

After a particularly stressful week, I started to go around our floor asking teammates whether they would like to go for happy hour

A colleague - Let’s call him Adam - was just coming out of a meeting room so I called out, “Hey we’re going for a drink, want to come?”

“No, I’m okay.”

“Aw come on, we’re all going!”

“No Jeff, I don’t want to.”

I shrugged and said, “Okay, your loss,” and proceeded to have a pretty fun night.

Fast forward to Monday

I receive a message over Chat -

“Jeff, I don’t appreciate you pressuring me into joining happy hour last Friday. I made it clear that I didn’t want to go and I felt uncomfortable having to justify my actions in front of the team.”

I was stunned, confused, and hurt. I thought I was being inclusive and nice. Who wouldn’t want to go for a drink on a Friday?

I went home that day and complained to my then-girlfriend, who said: “Yea but that’s your preference Jeff. How could you assume everyone likes what you like?”

A deeper conversation ensued and an hour later, I came to a simple conclusion: I was wrong, I should apologize, but dam, do I hate awkward conversations.

The next day, I asked Adam for a quick chat, which he agreed to. We found an un-used meeting room, and I said,

I’m sorry about Friday. Just because I think going out is fun doesn’t mean everyone else would too. I didn’t take your feelings and preferences into account and I shouldn’t have pressured you so publicly in front of the entire team…

I will never forget what Adam said next,

“Jeff, I used to LOVE clubbing man. Hell I would hit up LKF (Lan Kwai Fong) every chance I got. But now that I’m married, I’m definitely more the sleep at 10PM kinda guy. So I get it, I really do. I appreciate your apology, and honestly I didn’t expect you to do this. Let’s forget about it.”

Looking back, this apology was one of - if not the - most awkward conversations I’ve had during my time at Google. I’ve never been good with these types of talks and I usually pretend the problem will go away by itself.

In this case, having that chat was one of the best decisions I’ve ever made. We got along so well after this “incident” that Adam became my de facto mentor for the next 6 years (and he still is to this day).

Now, Adam is not only a senior leader within the sales organization but also a direct stakeholder of mine (I’m in the marketing team).

On a practical level, had that conversation not happened, my marketing projects might not have had the same level as support from the sales team.

On a personal growth level, I wouldn’t have gotten over my fear of having awkward - but necessary - chats, and I wouldn’t have benefited from 6 years of mentorship.

The next time you find yourself in a situation where you know the “right” thing to do is to have that hard conversation (with a friend, family member, partner, or colleague), don't run away from it.

Let your emotions settle for a few days, sure, but after that, prepare a few talking points, have that conversation, listen to their perspective, and put the problem behind you.

Adam, if you’re reading this, I really really hope you don’t mind me sharing this story. But, on the off chance that you do, I’m ready for another “awkward” conversation 😏

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