Tactics for Asking Good Follow-Up Questions

by Richard Davis

Whether you are looking to hire someone, decide whether to trust someone, or enter a business partnership, the better you are at judging people, the better off you will be. Unfortunately, most people are just plain bad at reading others. Several decades of research among psychologists has indicated all sorts of blind spots, biases, and judgment errors we make in assessing people. Much of that research has focused on the mental processes we use to interpret what we see or hear. But errors also occur way before that – the problem can begin with the questions we ask to understand people in the first place.

When you want to get a read on someone, what questions do you ask? Most people have go-to questions. The ones I hear most often are open-ended questions like, “What are your greatest strengths and weaknesses?” “What do you want to be doing in five years?” and “What motivates you?” Some savvier questioners ask behavior-based questions, like “Tell me about a time when you….”. Sounds great, right? Now, ask yourself if you have ever once actually learned the truth about someone by their responses to these questions. How many times have you relied on people’s responses to these questions only to see later that those responses meant nothing at all? Most people ask a question like this and then move onto another topic, seemingly satisfied that they heard what they needed to hear. In reality, they learned nothing about the other person.

In my experience conducting interview-based assessments for the last 12 years, I have found that this is because the first answer to one of these questions is only marginally helpful and may even be irrelevant. Yet most askers simply accept what they hear (good or bad) and, without asking any follow-ups, move on to the next topic on their list.

But the key to understanding people lies in the follow-up question. In my experience, there are two major reasons people don’t ask good (or any) follow-up questions. First, many interviewers aren’t actually paying close enough attention to ask detailed follow-up questions. To ask a good follow-up, you need to pay very close attention to how the interviewee responds to your initial question, and then build on his or her answer. The second reason most people are hesitant to probe is out of fear of offending the other person. But being polite isn’t the same thing as letting the other person off the hook.

Ask a follow-up that will help you really uncover what you are seeking to learn. Be curious, and you will be amazed what you uncover. Here are three types of follow-up questions that will enable you to understand more about a person:

1. Ask your original question again, slightly differently. Don’t be afraid to ask the same question twice. If I am interviewing someone and the person either deflects my first question or doesn’t give a real response, I will often say, “Let me ask you this another way…”. It is effective because you communicate that you are not letting the person off the hook, but you’re allowing them to save face by at least implying that maybe your initial question just wasn’t clear enough. It is a highly effective method of extracting a real response that will actually be predictive of behavior.

Caution: just make sure you change the way you phrase this second question, otherwise it can seem adversarial. The key is to ask the question another way, and declare that you are doing so.

2. Connect their answers to each other. One of my favorite strategies to understand people better is to link their responses to something they said earlier. I’m not talking about an attempt to catch someone in a lie, but instead connecting the dots between their answers. Good judges of character do this naturally – they listen intently, and tie what they hear to something said earlier in the conversation. Ask something like, “Oh, that’s like the time you…?” or, “Is that what you meant earlier when you said…?”. Beyond allowing you to understand the person better, it communicates that you are really listening, and actually provides meaningful insight to the person by pointing out a connection that he or she may have not even seen. It allows you to synthesize information rather than just hear it.

Caution: Overusing this can make you seem like a police detective seeking a “gotcha” moment. Avoid saying things like, “But that’s not what you said earlier…” What I am suggesting is to synthesize rather than interrogate.

3. Ask about the implications of their answer. When people answer a question without being particularly revealing, or by giving a very safe answer, what do you do? For instance, when asked about greatest weakness, someone says, “I’m a perfectionist” or “I work too hard.” Rather than accept answers like that at face value, seek to really understand the person by asking about the implications of their answers. With a self-proclaimed perfectionist, you might ask, “How does your perfectionism play out in the workplace?” or “What are the consequences of your detail orientation?” And don’t stop there – keep asking implication questions until you are satisfied you know what you need to know about the person.

Caution: When asking about implications, avoid being a litigator and turning them into leading questions. Instead, truly be curious about the behavior and what its effects are.

Coming up with a great list of questions is only the first step in conducting an in-depth interview. It’s the follow-up questions that will really tell you who you’re dealing with.

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