We are all guilty of asking “how are you?” at the beginning of every conversation and then responding “good, how about you?” and getting another “good, thanks” in return. Unsurprisingly, this greeting doesn’t really lead us anywhere meaningful; especially in a time when building a personal connection is harder to do through our screens.

Today’s blog post is focused on how you can start your conversations with better questions so that you can have more meaningful conversations with others.

#1 – What will make your day great?

Sometime last year, I tried asking this question instead of “how are you?” and it got a pretty positive reaction from my peers! This is a better question to ask because it gets the other person to do a quick reflection on how their day is going so far, and what would make it great (focusing on the positive). I’ve gotten some good responses like “I would like to fit in a workout session by 5pm” or “I am looking forward to having dinner with my family”… But my favourite response was “My day is already great because I am meeting with you!”

#2 – How has your [relevant topic] been going these days?

This question helps you demonstrate that you have been listening to your conversational counterpart in the past and have picked up on some of the hobbies, interests, or projects that they have been working on. Asking a more tailored question shows that you are invested in their lives, and can provide a gateway for them to share some new learnings or challenges that they have been facing in their endeavours. Some topics that you can chat about would be:

  • Home projects (e.g. home renovations)
  • Hobbies and habits (e.g. shopping on Amazon, playing chess, etc…)
  • Kids or parenting (there’s usually a lot to talk about here)
  • Books, movies, or TV shows (this is a fun topic)
  • Work projects and initiatives (keep an eye out on what they are involved in)

#3 – What are you looking forward to this weekend?

The one thing that we all have in common is that we love the weekend (which is usually too short). No matter what day of the week it is, we can always look forward to talking about our plans for the weekend. Asking this question is also great for collecting information that can help you ask Question #2 in the following weeks when you catch up with them again. If it’s a Monday or Tuesday, you could also ask what they have been up to over the weekend, but this may fall flat and end up with a “nothing much, how about you?” response.

#4 – What is something exciting that has happened to you recently?

This is an interesting question to ask during COVID-19 lockdown times since there isn’t too much going on, but you never know, maybe your coworker is super excited about the new Instant Pot or Air Fryer they just ordered off of Amazon! If this question doesn’t lead to much of a response, you can always fall back on Question #3 and ask them what they are looking forward to instead.

#5 – What are you looking forward to accomplishing this [time period]?

Similar to Question #3, this is a timely question since we are early into a new year and we can get a better understanding of what some of their goals are, and perhaps talking about how we can support them. If it’s later on into the year, you could always ask what they are looking forward to accomplishing in the week or month to get a better sense of what is important and relevant to them during that period of time.


There you have it: 5 easy questions that you can ask instead of “how are you?” in your next conversation. Speaking from experience, it will be tough to break out of the habit of parroting those 3 words (sometimes they just slip out of your mouth), so be patient, but be persistent!

Here is to a 2021 filled with better conversations and connections with the people in your life!