CHAPTER 2

WHAT MAKES A GOOD QUESTION?

WORKING ON THE premise that it’s a good idea to ask questions, while recognising the various reasons that we don’t naturally do so, how do we get good at it? I’ll approach that question on three levels. In this chapter, I’ll talk through what makes an effective question, or what might be the right sort of question to use in a particular situation. Then in Chapter 3, I’ll discuss some of the underlying traits that will help us become good at questioning. And in Chapter 4, I’ll work through some ideas to help make this a habit or default setting. The Appendix will provide a few example questions that can be used in different situations — from innovating, to selling, to managing a team member.

Effective questions

A question that helps you achieve a desired outcome is an effective question. Usually, that means it gets someone thinking about a problem that needs solving, or about an opportunity that may be worth pursuing. It’s a question that forces them to think and, ideally, guides them to think in a useful way.

In most cases, that will mean helping them to think in a way that is valuable to them and helps them to progress with some aspect of their work. Sometimes, it can mean helping them to think in a direction that is intended to serve the wider business or other stakeholders in it. For example, it may mean helping them to understand why certain policies are in place, why certain standards have to be upheld, or why certain tasks have to be completed. Of course, the specific situation will partly determine what question is likely to be most effective.

In almost all situations, there is simply not only a single correct question to ask. In fact, in most cases, it is a longer conversation, inclusive of several questions, that will achieve the desired outcome. Later in this chapter, I will introduce the question funnel, which helps explain the way that different types of questions work together and how to use the right questions in the right sequence. However, before looking at the overarching funnel, it is worth understanding some of the common types of questions and the principles that apply most often.

Open questions

In most cases, open questions will generate more thought than closed questions. By open questions, I’m referring to those that cannot be answered in one word or those for which the answer is not simply yes or no. Of course, such closed questions are often necessary — they can make a point, and they are used countless times to attend to details and less significant matters. However, as a way of engaging in meaningful conversation, as a way of helping someone think more deeply about something, or as a way of influencing someone, they only have a small role to play.

In most cases, open questions will generate more thought than closed questions.

Open questions usually begin with:

‘Why …’

‘What …’

‘How …’

Or a phrase such as, ‘Tell me about …’

Open questions demand fuller consideration and thought than closed questions and will often trigger deeper insight as a result. The thinking process required to answer such questions can be the most valuable part of the conversation.

Returning to that dismal winter’s day, how might John have approached his conversation with Sarah (his boss) differently? How might he have prompted her to listen to him and consider his perspective? Let’s think what might have happened if John had asked Sarah a question such as, ‘What do you see as the greatest strengths we should be focusing on?’ and then followed up with a question such as, ‘How would you recommend dealing with our primary internal challenges?’ Had he asked those questions and then given Sarah appropriate time to respond, would she have just ignored him? Probably not. Would she have had to give the matter some consideration and provide an answer? Most likely.

How about John’s conversation with Harry (the head of delivery)? How could John have prompted Harry to consider the need for increased production? What if John had started with a very general question such as, ‘How are things in your world, Harry?’ and then led into ‘Where are you seeing the biggest opportunities to increase volume?’, ‘What are the primary changes you’re focused on in your operation at the moment?’ and ‘How best do you think we can maximise output?’ All could be relevant questions to get Harry engaged with the subject of increasing deliveries. Most importantly, all are open questions, and Harry would have had little option but to give them thought, provide answers and engage with the subject.

As a general principle, it is almost always most effective to begin with open questions. At other stages of the conversation, usually later in the conversation, closed questions become useful and can certainly serve a valuable purpose. The transition from open to closed questions will be discussed later in this chapter.

Difficult or confronting questions (kidney questions)

It is worth noting at this point that often the most difficult questions are also the most effective questions for helping someone to think differently, understand more deeply, and have breakthroughs. These are the questions that require the most thought and, sometimes, are the most confronting to the person answering. These are the questions that are often followed by a particularly awkward silence. A great questioner will celebrate that silence — the more awkward, the better.

Often the most difficult questions are the most effective questions.

For example, if you’re working with one of your team members on their development and they’ve been struggling to hit targets, a series of questions such as the following may be worthwhile.

1.So, tell me what you’ve been most focused on improving in your work processes.

2.How’s that been going?

3.If that isn’t working, what else could you be trying?

4.If you’re not able to hit your targets next month, what other alternatives should we consider?

Depending on the precise situation, any of these questions could be challenging for your team member to answer. Any of them could require serious thought to come up with strong ideas. The silence exists because the person answering the question has to think deeply and engage their mind fully. This is exactly what you’re looking for. So, embrace the silence and don’t interrupt! Don’t try to fill the silence with words, or with potential answers; keep quiet until the person comes up with a reply.

One of my early coaches used the expression ‘kidney question’ in this regard. These types of questions are most useful when trying to drive a significant change of behaviour in someone, and they stem from the basic level of human motivation. Put simply, humans are subject to two fundamental motivational forces — pain avoidance, and goal achievement. We will typically make changes either to escape something bad or to move toward something good.

Which one of these is more powerful? For almost all people, it’s pain avoidance. Because survival from danger was such a significant part of our evolutionary process, pain avoidance developed as a much stronger driver for most people. So, when trying to influence somebody to change in a manner that you know will be good for them or the business —  but they are not readily recognising nor embracing —  the process of asking very open questions is often about finding their pain point or their challenge. Put another way, the process is helping them to identify the problems with their current situation or the problems that might arise in future from it. It is an exercise in finding their kidneys.

Once that point has been identified, more directive questions, or sometimes even closed questions, can be used to really emphasise the pain point. This is like metaphorically twisting the knife to make the kidneys bleed. In the series of questions listed previously, if it was becoming apparent from the answers that the team member was not coming up with any solutions and was making no progress in their development, a fifth and closed question could be added to bring real emphasis to the problem. Such as, ‘Well, in the absence of progress, or any ideas for improvement, is there any realistic chance of you hitting your targets?’

When to use open and difficult questions

Helping someone to make a substantial change to their behaviour is perhaps where this technique of finding someone’s kidneys is most commonly required. As a professional coach, it can be invaluable. As a manager developing their team, likewise. For example, when speaking with Bob about adopting the correct sales process, John might have started with the open question, ‘Tell me about your sales conversion over the last few months, Bob.’ He could then have been slightly more directive with a question such as, ‘Which parts of our company sales process have been working best for you?’

If Bob had not been using the company sales process, this would likely be a short answer. (He’s found Bob’s kidneys!) John might then follow up with questions such as, ‘What impact on the business will it have if you keep going like that? What do you think the impact will be on you, your bonus and even your future here?’ And now Bob’s kidneys are bleeding! Pain relief can then be provided through a question such as, ‘How might you go about addressing this and improving that outlook?’ I make light of a serious subject here, but this is all done in an attempt to assist Bob in becoming more successful — something that is surely in his best interest.

Similarly, in some sales situations, where substantial change is required from the prospective buyer, the use of such kidney questions can assist in helping the prospect to recognise their own need for change. For example, when John was meeting with Alex, the bank CIO, John should have asked open questions about the bank’s current systems to identify any problems or areas in which John’s system would provide a better solution. Upon finding such a problem area, John could then have dug deeper with questions such as, ‘How much is that problem currently costing the bank?’, ‘What will be the impact if that problem continues for another year or two?’ Or even, ‘How is that problem impacting you personally, Alex?’ Such kidney questions would likely have helped Alex to recognise the value in exploring a different system. They would almost certainly have been more effective than John’s approach of just telling Alex about his product and its qualities.

From building a successful coaching business, I learned that for us to be able to help someone, we had to help them recognise their problems before they had any chance of solving them. Kidney questions were often the best way to enable that. Yes, it would be momentarily awkward, even painful, but it was always done with the positive intention of enabling us to help them.

Goal-oriented questions

Seeking these pain points is usually an effective way to motivate change in someone. At the same time, it is worth recognising that some people are very goal-driven. That is, they’re as motivated by goal achievement as they are by pain avoidance. In addition, it is often the case that uncovering pain points will create a level of discomfort that, while not enjoyable, may be insufficient to drive the desired change. In light of these considerations, it is always sensible to also have a list of goal-oriented questions. Generic examples of these might include:

Where are you looking to get with this?

What will success look like in this?

What would the ideal outcome look like here?

What’s your ultimate goal with this?

These will all help to sway people who are goal-oriented, as well as motivating anyone answering them.

The question funnel: how to dig deeper

As discussed previously, as a general principle, think about using open questions first. As the conversation progresses, you may then start to use slightly less open, or more directive questions, to dig deeper into a particular topic. For example, when managing a staff member, you may simply start with a wide, open question such as, ‘How’s your day going?’ The answer to that question may immediately highlight a subject about which you should dig deeper.

For example, your staff member may answer, ‘Fine, but I’m having real problems with a couple of my team members.’ At this point, you know that your next question should be directed at the team member issues. Alternatively, the answer may indicate very little — ‘Fine thanks,’ would not be an uncommon response. Either way, it is appropriate to dig deeper, still with an open question but now with a slightly directive question — directive as to the subject you’d like to explore.

The next question may be something like, ‘Tell me a bit more about how your team members are doing.’ While not actually a question, this statement still serves the purpose of requiring thought and a considered answer. You are now directing the conversation to a particular topic, but still asking the type of open question that generates real consideration and mental engagement.

The process of digging deeper is an invaluable skill to master and quite a simple one. It can be as simple as using a few prompting statements or questions. ‘Tell me more about that,’ ‘Why is that the case?’ or ‘What’s the impact of that?’ are examples of statements that can be used again and again in almost any situation.

Eventually, in the course of the conversation, it often becomes appropriate to ask an entirely closed question. This may be to clarify a point, or it may be to emphasise a point. For example, perhaps you’re in a conversation with a member of your sales team and you’ve established, through more open questions, that they’re not utilising your defined sales process. As a result, their conversion rates are down, as are their overall results. A couple of questions such as, ‘Do you think these results are helping you and the company?’ and ‘Do you think this is leading you to your bonus?’ would be effective in bringing emphasis to the point.

In a sense, think of the overall questioning process as being like a funnel. Begin with wide, open questions (the top of the funnel), gradually direct the questions toward the most relevant areas (the narrowing of the funnel) and then bring strong emphasis with closed questions if required. In your attempt to influence someone, you are trying to narrow their focus to the most important point(s) and have them think properly about those points. That too can be seen in the funnel — when they have the aha moment or reach the vital conclusion, they have exited the base of the funnel.

Questions that enable change

With the image of the funnel in mind, what is happening as you move down the funnel? Assuming you are trying to influence the person you are talking to and wish for them to take a particular action or adopt a certain behaviour, then you are trying to make them change. As we’re all aware, that isn’t always easy! As a general principle, people don’t enjoy change, typically preferring the comfort of what is familiar to them.

In order to achieve change in someone, there are a couple of things that must occur: they must be motivated to change, and they must understand how to change. In line with this, you will benefit from directing your questions at these two requirements. Asking someone questions that uncover the problems or pains of their current situation and that highlight the positive benefits of a possible future situation will help the person to recognise the reasons to change. This is the motivation part of the process and, as ever, will be most effective if you can ask questions that permit the person to recognise it for themselves.

In my experience, there is almost no amount of telling that will achieve the same result as helping a person to work it out for themselves. Then, asking questions that enable them to come up with the new course of action, or different behaviours to adopt, will clarify for them how to change. In both cases, it is the focus on helping them to come up with it themselves that is most effective in actually achieving the desired change.

Planning the questions to ask

So far in this chapter, I’ve focused on some general principles about how to ask effective questions. Not surprisingly, the precise questions that will be most effective in any given situation will vary from situation to situation. So, while it is valuable to master the general principles, it is also vital to come up with good questions specific to a situation.

While it’s not usually difficult to come up with these questions, it does require effort. If you know you have an important meeting coming up, or you know there is someone you need to influence, set aside time in advance to prepare some specific questions. Whether that’s before a sales meeting, a meeting with staff, a negotiation with a prospective partner or other such meeting, the time spent in preparation will pay off in spades. Simply write down a handful of open questions to use and a couple of more directive (but still open) questions to use on the specific topics you’d like to discuss during the conversation. Then practice them for a few minutes (familiarity and muscle memory will make the delivery of those questions so much more effective), and you’ll be ready to go.

In the end, coming up with appropriate questions should be quite straightforward. It will always come from the following thought process.

1.Do you want to influence this person?

2.If yes, how do you want to influence them? That is, what is it you want them to do?

3.To make that change, what will they need to think? What, specifically, will they need to realise or understand?

4.What series of questions will help them reach that realisation or understanding most swiftly?

It’s as simple as that!

The importance of listening

The final word on asking good questions isn’t about questions at all. No discussion of questioning skills would be complete without mentioning the skill of listening. Weak listening skills can very quickly ruin the effect of even the best questions. So, what do good listening skills look like?

Weak listening skills can very quickly ruin the effect of even the best questions.

Put simply, good listening skills look like listening. That is, they don’t look like talking. The first step in listening well is to ensure that you’re listening and not talking. I’ve already mentioned the potential power of silence. In all cases, for your questioning to be effective, you must allow the other person to answer. And you must allow the other person to think about their response — remember, it is that thinking that is often even more valuable than the answer itself. So let them think and let them answer.

There is a great saying in sales that can be applied to many other conversations as well: ‘The prospect drinks their coffee cold. The salesman drinks it hot.’ The point being that a good salesperson asks good questions and the prospect does most of the talking, so doesn’t have time to drink their coffee while it’s hot.

How can you improve your skill of listening, apart from not talking as much? There are definitely techniques that can elevate the effectiveness of your listening. Some basics might include:

maintaining good eye contact

nodding at appropriate moments to indicate that you’re hearing the other person

using positive confirmation of what you’re hearing will encourage further thinking and talking on their part (for example, simple statements like, ‘That’s great.’ ‘Tell me more …’ ‘That’s interesting.’ ‘Wow, fantastic.’ ‘Perfect.’)

repeating back what you’ve heard as a way of confirming you’re listening or summarising what you’ve heard

asking follow-up questions, which demonstrates that you’re hearing the other person and also serves to prompt further responses.

These will all help to increase the effectiveness of your questioning by demonstrating the quality of your listening. However, the first step upon asking a question is to stop talking. Just listen.

The first step upon asking a question is to stop talking. Just listen.