The Art of Follow-Up: Asking Questions That Keep Conversations Flowing
+ keep scrolling for the question that I want to ask every morning
“What I want to work on is follow up questions,” a reader wrote to me recently.
It’s a good observation—a really great question can launch a conversation, but the conversation is more than the question. So how do we find the magic that lets us continue a robust conversation?
Last week’s post addressed half this question with the reminder of how we need to show up in the conversation.
This week we address what comes next. Once the conversation has started, how do we keep it going?
Questions and next steps for deeper conversation
Great conversation is unpredictable. If you knew exactly what was going to be said, you wouldn’t need to have the conversation.
But just because something is unpredictable doesn’t mean you can’t show up prepared. I keep these ideas in my back pocket to help me deepen a conversation, increase my understanding, and get to the heart of a topic.
Tell me more:
Early in a conversation, it’s important to make sure you’ve heard what needs to be said or shared.
“Say a little more,” or “tell me more about that” can be great prompts to get your friend or colleague to elaborate.
Repeating back the last few words someone says is another great tool for getting more information. It is a simple signal that you want the speaker to continue. For example:
Friend: Last night was rough.
You: Rough?
Friend: Yeah. My daughter came home from school mad and …
Make connections:
Once the details are on the table, it’s often time to take the conversation deeper. Questions that help you connect the topic to other experiences or work are a great way to do this.
A previous post on integrative questions offers a lot of thoughts on how to do this well. In short, your goal is to explore a connection between the current context and something else.
What does the dip in sales mean for our overall plan?
How could we get through the most important things on our to-do list and still have a relaxing weekend?
How do your memories of your father influence how you want to parent?
Listen with your gut:
Great follow up conversations are often found in your gut rather than in your head.
Pay attention to body language, to what is NOT being said, to the tone of the conversation. Then ask a question based on these observations.
You’re saying you can get everything done, but I sense you have concerns. Am I right?
I notice we haven’t talked about the impact on our existing customers. What are your thoughts?
Probe at places where you aren’t aligned:
It’s healthy for colleagues and family members to see things differently. When you hit on an area where differences exist, probe for more understanding:
Will you walk me through the approach you’re recommending?
I can tell you feel strongly about this, and I respect that. Will you help me understand more?
Summarize and check for understanding:
Looping is a communications technique that involves summarizing what you’ve heard from another person, and then asking, “Did I get that right?”
Looping is great for tense conversations, because it helps people feel heard, and it ensures you’re understanding the real message. But it’s also great for evolving a conversation— especially a conversation that has meandered. Use your summary to call out the key messages, check for understanding, and then ask something like, “Okay, what else?”
Active listening is required
Finally, it bears mentioning that active listening is essential for any of this “doing and being” to work.
How often are you in a group Zoom meeting where someone asks a question that was just answered? Or when someone changes the direction of a conversation because they were focused on their perspective instead of the group’s conversation?
Having a great conversation means giving your full attention.
The skill of great conversation requires practice. Try these ideas, and then use the comments below to tell me what you do, after the initial question, to make great conversation possible.
BONUS QUESTION
My friend and fellow Substack newsletter author Garrett Bucks has given himself a challenge that is worthy of our consideration. It’s beautifully simple:
I'm going to start the day asking “how am I going to either deepen an existing connection or build a new one?” I’ll then end the day by asking myself how I did.
That’s your bonus question of the day. How will you deepen an existing connection or build a new one?
Leave a comment and let me know what your challenge will be.
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Photo by LinkedIn Sales Navigator