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Kevin Oubridge

Blue Chip Coaching Limited


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16 Questions that Will Change Your Life (and Help You Win More Coaching Clients)


There’s a well-worn sitcom routine in which two single people meet on a blind a date. One of them, desperate for a loving relationship, can’t help blurting out the history of previous failed relationships and how much they want marriage and children. It’s too much, too soon, and there’s no second date.

I most recently saw it played out on an episode of The Big Bang Theory! Penny set Raj up on a date with a friend of hers.

It was a disaster!

What is wrong with you? The friend screams at Penny after the date. What is wrong with you? Penny later screams at Raj. What is wrong with you? Raj screams at his reflection in the mirror when finally alone.

It’s sad but also funny because it’s something we can all relate to. With coaches it’s not love they’re looking for, it’s clients. But with both it’s about relationships and it’s easy to make a mess of things when you first meet.

What's wrong with you?

Well, you might not ask that of yourself after failing to win a new client. But you will certainly feel frustrated and, after several failed attempts, you can get a little desperate. You end up asking potential clients to ‘marry’ you almost before you’ve told them your name. Or maybe you settle for having a pleasant chat, hoping they’ll ask you to ‘marry’ them. Not surprisingly, neither approach works.

Your aim with the first conversation with a potential client is to find out whether there’s value for both of you in scheduling a second conversation. Ask about their work situation. Give them some information about your services. You’re certainly not at the stage where you should be trying to walk down the aisle or sell them anything.

The second conversation might be to move things towards a more formal meeting, where you discuss the potential clients work situation in depth and how you can help them. Or it can sometimes be the more formal meeting itself. It depends on how good you are at building the relationship and, of course, whether your potential client is a genuine prospect or not.

By asking the right questions you can quickly sort the genuine prospects from the rest. You can then focus on building the relationship with people who you have a good chance of converting to paying clients. But what questions should you ask? Here’s my top 16:

1.   Can you tell me more about your role?

You’ve met a potential client, you’ve exchanged names and what you do.

Now what?

The best way to engage anybody in conversation is to show interest in them without getting too personal. So ask them to tell you more about their role. Not only will they be pleased that you are interested, they will know what to say. It’s their role after all. The thing they spend most of their waking hours doing or thinking about. They will have lots to tell you.

It’s an easy opening for you and your potential client.

2.   How long have you been doing it?

Having got your potential client talking, nudge them along with simple follow-up questions.

This is a useful question because it takes them away from the here and now, with all its detail, and gets them thinking a bit more about the context of their role.

3.   Where were you before?

This question is again useful for nudging your potential client along. It gets them thinking about how things used to be compared to how they are now. What they liked and disliked about their last job, and how they feel about their current situation is.

It provides a bit more context for both of you.

4.   What prompted you to move?

Perhaps a slightly more challenging question. It’s more personal, asking your potential client to tell you about themselves, rather than purely about their job. Getting personal at the right stage is a good thing. It helps build rapport, which is essential for the relationship longer term.

It may also be an area your potential client doesn’t want to get into. Not in itself something that would make you think they are not a genuine prospect, but a sign that they may not be.

Challenging your potential clients in this way either moves the conversation along or tells you where the initial boundaries are.

5.   I know your company is focused on driving initiatives to improve productivity at the moment. Is that something that comes under your remit?

Now you’re getting interesting! This question is useful on a number of levels.

Firstly, it directs the conversation to a specific area. Of course, you need to have done your research, enabling you to know what the company is focusing on. Plus, you need to make sure that the area you direct the conversation to, is where your expertise lies.

It’s got to throw up challenges that you can help them with.

Secondly, it helps you determine whether you are talking to a genuine prospect or not. If they say no, it’s nothing to do with them, maybe they are not a good fit for your coaching. Don’t write them off totally at this stage though. There may be other areas which are under their remit you can help them with.

Lastly, if they say yes, it gets them thinking about real problems they have in their role. When they answer yes to this question they are no longer talking generalities, they are talking about what keeps them awake at night.

6.   Tell me more.

Okay, this isn’t a question but it is an incredibly useful link. It keeps your potential client talking, giving you useful information to help you understand if they are a genuine prospect for you or not.

‘Tell me more’ is a standard coaching question that you can use repeatedly at all stages of your marketing and selling process. It’s so easy. Very powerful and extremely effective.

7.   Driving change on the important initiatives is a real challenge for rapidly expanding businesses like this one. Leaders are so often pulled into firefighting that focusing on the right things that make a difference to results can be almost impossible. How have you been able to square this circle?

This is a technique I picked up from Shelly Rose Charvet, Words that Change Minds. It’s a lot to get out. Don’t worry about this though, your potential client will benefit from a break from doing all the talking. They will also have to engage fully to understand and give you their answer.

Of course, you should use an appropriate example for your target market, but the question at the end remains the same.

And what a good question it is!

The previous two questions got your potential client to think about the challenges they face. This question gets them thinking about how they are tackling those challenges. If you have built rapport and trust this is where they will open up to you, maybe telling you they haven’t managed to square the circle. If they begin to share important information with you, you know you are making progress.

8.   And how is that affecting you?

Another useful follow up question that gets your potential client to open up a bit more. It can reveal some of the emotions connected with the business issues.

You need to listen very carefully here. Does this person sound like someone who needs your help? Is what they’re talking about something you can help them with?

9.   What does it stop you doing?

After a certain amount of introspection around their problems, you are now getting them to look at the outcomes they want. They may be very clear what they are prevented from doing, meaning they may be frustrated by their problems. On the other hand, they may not have much of an idea what they can’t do, meaning they are bemused by and adrift on their problems.

Either way, tell me more!

10.   What’s the impact of not being able to do this?

Now you’re getting down to the nitty gritty. You’re picking up on the most significant thing that their problems stop them from doing and getting them to think of the wider impact. This is important because you’re starting to get them to evaluate the full cost of their problems. This not only shows them how much they need your help, it also demonstrates to them the value they will get from working with you.

There's a whole string of supplementary questions that you can use to drill into this further. Here are just a few:

How does it impact your team?

How does it impact your customers?

How does it impact your target numbers?

How does it impact your manager’s targets?

How does it impact your objectives?

How does it impact your manager’s objectives?

How does it impact business results?

11.   How important is it for you to attend to this issue?

They may give you a short answer but it will be heartfelt. You’ve taken them from a polite greeting to telling you their woes and how much they are hurting them. It’s a lot to get off their chest and they may feel delighted as well as energised and focused.

12.   And how urgent is it?

If attending to this issue isn’t urgent and important there is probably no requirement for you to help fix it. However, if they say it is urgent or it needs sorting out before they can do anything else, this is a good sign for you. You have helped them to this point and they are therefore likely to want to continue the relationship.

13.   May I tell you a little about what I do?

Use your Elevator Pitch to describe your ideal client and when you would work with them. This is your first opportunity to really build your credibility. Listen closely for whether or not your messages resonate.

Do not talk about how you deliver your service. As a rule, the prospect isn’t interested in that just yet, it’s too early in the conversation.

Be able to talk about the results clients typically get when they work with you. Have some relevant case studies you can share.

Does it sound like the prospect might be looking for the kind of help you offer? By now you will have a good idea of how interested they are in continuing the conversation.

14.   Does what I do sound like it might be of use to your organisation?

There comes a point where you have to raise this subject. So make it direct. If they say no, you’ve given yourself every chance of winning their business and got a straight answer. This will save you time pursuing this potential client, only to find out much later that they’re not interested. And you’ve done it with a brief conversation.

If they say yes, you need to have your next step planned. You could either offer to send them something of value, such as an article you’ve written. Or, if the signals are right, you could offer to set up a more formal meeting to dig a little deeper into their situation.

Try to rush things and you could blow it. However, move too slowly and you could also lose the opportunity to move on to the next step.

It’s your call here.

15.   I have an article you might be interested in. Can I send it to you?

Offering your potential client something of value to them is a good way of continuing the relationship beyond first contact. A ten mistakes article or one that explains how you’ve helped previous clients works well. If you haven’t got one, write one. Or use someone else’s, making sure you credit them properly.

If they say yes, get their contact details and say:

And if you don’t mind I’ll call you next week to get your reaction to it?

The thing to remember here is that, having promised to send them an article and to follow up with a call, you must do both. And don’t be put off if you can’t get them on a call at the first attempt. They will be busy. It doesn't mean they are not interested.

Keep trying!

16.   How would it be if we set aside some time for you to think about this issue in more detail? I’m in London 3 days a week and I offer a free, 90 minute consultation. During the session we would explore the bigger picture and then drill down into the detail of what your part of the business needs to get better at in order to address your problems. Would that be of use to you?

It may be too early to offer your potential client a more formal meeting. Sometimes, however, it’s the natural thing to offer this as a next step. If they need a little more persuading you could try:

I’ve worked with a number of leaders in similar situations and they report just being able to step back from the firefighting, even for a short time, illuminates where their focus should be and how this can help them deliver improved results, faster. Would that be of use to you? 

Such meetings are an excellent way of giving your prospect an experience of your service and, ultimately, for winning their business.

With practice, using these questions will become second nature for you. Of course, real life isn’t how I’ve written it in this blog post. This conversation may take place over several weeks or even months, involving multiple telephone, email and in-person connections.

The key thing to remember is that your aim with all potential clients is to first determine if they are a genuine prospect. If they are, your next step is to get them to agree to an in-depth meeting where you can find out more about their situation and tell them a bit more about your services.

If you can do that, you may hear wedding bells!

Want to learn how to grow your coaching practice?

Download The Alligator’s Bite - it's FREE! I reveal the step-by-step process you can use to win Blue Chip coaching clients and build long-term relationships, where you win further business year on year. You’ll also receive regular Blue Chip Tips blog posts to your email.

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Kevin Oubridge


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