10 revealing questions to ask an expert before you hire them

Congratulations! You’ve decided to get some expert help in your business, either to do something you can’t do yourself, or something you don’t want to.

Now you just need to decide who to work with. However, if you don’t have specialist knowledge in a field yourself, it can be a challenge to know whether someone is really up to the job.

The good news is that you don’t need to learn their skills first. Instead, the key is to ask insightful, open, questions that will uncover their ways of working and experience.

Whether you’re looking for a web designer, a marketing consultant, a mailing house or someone to edit your podcasts, here are 10 powerful questions to get to the heart of how someone works and whether they’re going to be right for you.

1. This is the outcome I want. What problems or challenges might you anticipate in achieving it?

It’s important to be very clear about the final result you want from someone. Once you’ve decided that, asking them about possible challenges will help you see whether they’ve understood what you want, whether you need to clarify it further, or whether they simply aren’t expert enough to understand whether what you want is realistic or not.

2. What are the things most likely to go wrong along the way?

Be wary of anyone who pretends that everything always goes swimmingly. Expect someone to be able to explain the biggest risks, or the best things to do to avoid them. For instance, a mailing company may have experienced that getting a corrupted data file from a client is a common problem, or that a lot of people being involved in making a decision can delay things. You can develop the conversation by asking how to avoid those situations, or what you would both need to do if those things happened. A lack of detail may well indicate a shortage of experience.

3. What would success look like to you?

This is normally a question a good supplier might ask you. But it can be worth turning it round to reveal their motivations and understanding. A web developer saying, ‘building you a website that you can update easily, and that doubles your mailing list’ would show that they’d listened to you, and be far more convincing than someone answering, ‘building you a website that you like’. It also shows what’s important to them. If someone highlights quick, effective communication as an element of success, but you’re invariably slow at answering messages, you may not be right for each other.

4. What do I need to do to make the process run smoothly?

Any expert needs to have your involvement. A good collaborator will be able to explain how you can help to make things run well. This is invaluable information for you, as the last thing you want is to be responsible for things going wrong because you weren’t aware what you needed to do.

5. What time commitment will you need from me to make this work as well as possible?

A mismatch of expectations is a recipe for unhappiness on both sides. A printer might need you to be present (overnight, and at the other end of the country) for the first print run of your new catalogue but just want regular short phone calls after that, while a coach may advise that you need to plan in two hours a week for the next three months for the best results. Getting things clear upfront will help you understand if it’s right for you.

6. What should I do if I’m unhappy with the way things are going?

It happens. Things go wrong. You want to work with someone who seems genuinely comfortable with the idea of potentially difficult conversations. If they’re comfortable with the question, it’s a good sign they’ll be comfortable dealing with the situation.

7. What isn’t included in your package?

You’ll probably ask what is included, but it’s always asking what isn’t. Will extra phone calls between meetings be charged for? What about travel? Reversing the question can help them remember things they may not have thought to mention.

8. What happens if we need to change my brief?

Projects change and evolve all the time, but if it changes the amount of work, it’s likely to change your bill. Agree how many changes, revisions or extras are included in the cost, and what happens if things go beyond the brief. Do they tell you as you go along, or do you only find out when you get the invoice? You’ll also get a sense of their approach: will changes be a hassle, or a normal part of the process?

9. How do you think you can make a real difference to my business?

This is a good way of checking whether they understand what your business is, and whether what they want to do is the same as what you want. If they don’t get it, it might suggest that you haven’t communicated it well enough, or you might have an uphill struggle to work with them. Look for enough specific information in their answer to show that they understand what they need to do, and how they will go about it.

10. What do you look for in a great client?

You’ll get the best work from people who really want to work with you. Most people want clients who share their values and approach. See if what they say resonates with you. If their answer sets off alarm bells, it probably means you’re not the right fit.

Have some other great questions? Let me know in the comments!

Be the change that you want to see. Step into your leadership.


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