Let's ask better follow-up questions

When I watch and read a great interview, I notice something. The interviewer typically accomplishes to 'square the circle' in a particular way: they manage to follow-through with their plan of questions, while building their questions on what the other person said.

It's hard to understate that skill and I take a lot of joy when see it in action. You can quite easily tell a junior interviewer from a senior one by their ability to ask great follow-up questions. Some people just barrel through their script, ignoring golden nuggets that the guests shared and pushing through their agenda, while others are able to connect what was just said to where the interview needs to go.

It is here where interviewing and coaching skills overlap. Good follow-up questions are a sign of respect. They show that you actively listen, you're actually processing what the other person shared. The good news is that this is a skill we can all practice.

Instead of jumping to the next idea/topic/thought after someone speaks, try this simple technique: pick up on a specific word or phrase they used, especially one with a bit of energy or emotion behind it.

Example from work:

Someone opens up to you and says, "I'm struggling to make a meaningful plan here."

❌ Moving on: "Okay, thanks for sharing. I mean it. I hope it works out. But let's move on to the next agenda item though, given we have so much to discuss..." (Dismissive)

✅ Acknowledging: "I heard you talk about a plan. What exactly are you referring to?" (Good, shows you heard the other person.)

✅ Deeper Dive: "You mentioned meaningful. What makes a plan meaningful to you?" (Explores a word that is more likely connected to emotion)

✅ Connecting to Context: "Thank you. I hear that meaningful plan is a real struggle. I want to help, at the same time we have a meeting agenda right now that we agreed to. Could we discuss this particular struggle a bit later today?"

(acknowledges and holds the ongoing meeting on track)

When we make an effort to build on what was just said, it sends a strong signal. In fact, it's an amazing feeling when somebody does that with you. The best conversationalists you know and like are likely very good at this skill that easily flies under the radar.

Try it out in a conversation this weekend or in the coming week. Good luck...and let me know how it goes!