There is no amount of online research that can match the value of asking questions to real live people. You can Google til your fingertips are blistered, lurk in forums until it starts to feel kinda creepy, or even ask your best business buddies what their experiences have been with clients.

But nothing will come close to the insight and intel you’ll gain when you focus your attention on asking more questions. You’ll know what makes your clients tick, what success means to them, and uncover the absolute best ways to deliver it to them on a silver platter.

Crack that code and you’re on your way to better results, raving clients, and more referrals than you can shake a stick at.

Asking just any old questions won’t cut it though…it’s gotta be the right ones, at the right time.

During The Consult Stage

When you’re just getting started with a new potential client, your main focus in your line of questioning is to learn more about their needs and wants, what their priorities are. By uncovering this information early on, you can take a pre-packaged offering that’s 90% of the way there…and customize to be a surefire hit.

Some questions to try:

What one thing absolutely must happen for this project to be considered a success?

And then you’ll know what you need to deliver. Shout out to Jules Taggart for inspiring this one!

Where do you see your business/life 1 year from now?

Clear vision? That means you’ll have neat metrics to hit. Fuzzy vision? You may be more of a mentor or coach than a nuts ‘n bolts service provider for them.

How did you hear about me?

Random? Then they may not know much about you, or what you offer, so educate them. Referral? They’ve heard the (great!) stories – it’s now less about education, and more about execution.

Pro Tip: Being genuine, and actually giving two hoots about what the potential client is telling you is crucial. These first conversations will form the foundation of your future working relationship, so make sure you engage fully.

During The Negotiation Stage

Huzzah! The client is keen to work with you. Now to seal the deal, and hash out the details. Asking questions at this stage serves two purposes. First, it helps you move the conversation from ‘Yes, I’m really interested’ to ‘Yes, I’m in!’. Second, it opens up a world of flexibility for you to get creative in finding a solution for any contractual or commercial disagreements.

Try these questions:

What’s the element of the proposal that’s holding you back from saying yes?

When a client is hesitant to sign on the dotted line, we often assume it’s related to price. Don’t! Instead, asking this questions gives them the opportunity to share what the realy hold up is. Timing? Features? Or yes, maybe price.

Can you please explain the change you’ve made to the contract?

When a contract comes back with a few tweaks, but no explanations, it’s best not to assume why they were made. Book a call, and go through each change asking this question. Make note of the answer, then make your yay or nay decision.

What are some of the drivers behind this solution not working for you?

A.K.A. A more elegant way of asking ‘Why did you say no?’. If you’ve asked for something in your contract, and have heard a no, don’t give up. Find out why you got a no…so you can find a way to turn it into a big fat yes.

Pro Tip: Don’t rush through this process. Negotiations take time. Trust me. It’s better to spend a few extras days or weeks in this zone of discomfort, than to take on a client or project under terms that will leave you feeling flat later on.


During The Active Client Stage

Sale made. Ink dry. Time to just keep your head down and churn out the work, right? Wrong. Continue to be engaged with, and enthusiastic about your client’s project by keeping in touch and asking more questions to guide the work that you’re doing. This will help you stay on the right path, tweaking as you go – rather than finding out you missed the mark after allllll the work is done.

Give these questions a shot:

How do you feel about the direction we’ve taken so far?

The drafts or progress reports you’re providing may technically hit the mark, but you need to make sure that your client is still on board with the direction, and that they’re feeling good about what’s happening.

What can we do to get comfortable moving ahead with Option A?

Sometimes, you need decisions. And sometimes, clients don’t like to make them. Follow-up to that radio silence by guiding them through the process. Maybe there’s nothing that can be done to get them into Option A. Super. Then let’s get them into Option B instead…because we gotta keep moving this forward.

Phase 1 of the project is nearly wrapped up. Can you please confirm that the Phase 2 payment will be arriving on the 20th?

Matching the work you’re doing to a payment plan is a great idea – no money, no work. However, when that next payment runs late, it can throw off your whole project timeline. There’s nothing wrong with asking for a confirmation of that next payment as the due date approaches.

Pro Tip: Clients may be asking you a whole bunch of questions about status – and handling those can get in the way of actually doing the work. Proactively arrange for weekly or bi-weekly check ins with your client as their opportunity to ask questions and provide feedback.

During The Wrap Up

Whew. The project is done, your sessions wrapped up, and everyone is a happy camper. Right? This is a great time to make sure by asking for feedback on your work.

Take these questions for a spin:

What results do you expect to see in the next 6 months as a result of our work together?

Some of your work may yield immediate results, but often the benefits only mature a few weeks or months later. Asking your client to predict what lies ahead for them is a great indicator of how confident they are in what you’ve done for them, and makes for great testimonial copy.

Is there anything that I could have done to make your experience or result any better?

Continuous improvement is the name of the game. Even small pieces of feedback will help you refine your process and performance to best match your clients’ needs. Be open to hearing it…and implementing changes though – no one likes to give feedback just to have it blatantly ignored.

How are things going? What’s the Next Big Thing on your horizon?

A month or so after completing your work together, reach out and ask the client for an update. Did the predicted results manifest? Are their customers raving? This is valuable information. Being curious about their next moves in business is also valuable…because it may uncover a need for your work!

Pro Tip: Following a successful gig, one of the biggest and best questions you can ask is “Do you know of anyone else who would be a great fit to work with me?” It takes serious courage to come right out and ask for referrals – but it’s worth it.

There’s no hard and fast rule about what questions you need to ask. Or who you need to ask. Or what the absolute best phrasing of those questions is. Sometimes an open-ended questions works, and sometimes a simple yes or no does the trick. Mix ‘em. Match ‘em. Find what works best for you, your business, and your clients.