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Getting Your Clients to Pick a Time Instead of Asking “What Time Works Best For You”

by Sean

What time works best for you? is the catchphrase of many freelancers and small business owners. Clients love when you’re flexible and take into consideration their busy schedules … right?

As it turns out, this seemingly innocent question annoys clients and may even put your business’s potential on pause.

It’s time to find out why!

Why Clients Hate That Question

Here’s how this client interaction typically plays out:

You: What time works best for you?

Your client: (Smiles politely) Let me check! (Hastily flips through dozens of pages in their appointment planner to search for the next free time slot that fits your schedule).

Sure, they don’t seem bothered by the question.

But that’s only because it’s rude to roll their eyes and sigh!

So what is it about this question that fuels silent rage inside your clients?

Let’s find out.

We All Have Busy Schedules!

Is your upcoming weekly schedule completely bare?

Are you willing to meet at odd hours like 8 a.m. or 10 p.m.?

Let me guess—you answered “no” to at least one of these questions (hopefully, both).

When you ask your clients what time works best for them, you’re tossing your calendar on the backburner. A future meeting—and a potential sale—is only going to happen when they can find 30 spare minutes to lend you.

Yes, each client matters, but leaving your week wide open for the sake of convenience for one client may put all of your other responsibilities on a temporary hold.

Avoid the Email Ping-Pong

Let’s assume you work 9 to 5 Monday through Friday. And for argument’s sake, let’s say you try to keep your meetings under 30 minutes.

That makes 80 potential time slots a week.

You confidently fire off that “Pick a time” message to a client and get a vague “How about Tuesday at 3?” in response.

Tuesday afternoon is no good.

“I can’t do Tuesday. What about Wednesday at 4?”

Try again!

Email ping pong is a logistical nightmare flooded with one new email thread after another (and the occasional rogue spam filter). You may be dozens of messages into an email chain before you decide that Monday at 11 fits into both of your schedules.

And that’s assuming neither of you gives up halfway through.

Time Zone Mix-Ups Can (and will) Happen

When you run a virtual business, it’s easy to forget that your clients aren’t always in the same state as you, let alone the same time zone!

Translation: Time zones can be a real pain in your side.

Here’s an example:

The time difference between the East and West Coasts is three hours. If your client in New Jersey says 8 a.m. works for them, and you live in Oregon, you better be in the mood for a surprise 5 a.m. phone call!

And unless you’re willing to memorize each clients’ time zone, your only other option is to do the conversions before scheduling each meeting.

It’s a lot of extra (and unnecessary) work!

They Don’t Know the Answer

Scheduling meetings would be easier if everyone worked 9 to 5 and did the same thing every day. But about 10% of people are independent contractors just like you!

In other words, they may not be able to give you an immediate answer.

At least not right now.

So when you ask this question and don’t accept “I’ll let you know” as an answer, can you really be surprised that clients get frustrated?

You want your clients to have a great first experience, right?

Then stop asking this question!

Related: 11 Mistakes Most New Freelancers Make That You Should Avoid

What Do You Have to Lose?

How to schedule meetings

We get it—bad habits can be hard to break.

And as a creature of habit, it might take you ten weeks (or longer) to completely ditch your old catchphrase and develop a better routine.

Is it even worth the effort?


And here are a few things you risk by keeping this phrase in your vocabulary:

Most Important to You: A Client

Let’s face it.

The more you anger, frustrate, or annoy your client, the less enticed they’ll be to schedule a future appointment with you—let alone book a paid session.

And technically, they don’t have to.

Unless you’re the only local yoga trainer or rodeo photographer, your clients aren’t stuck working with you. If scheduling an appointment with you is a hassle, you could guide your clients right into the arms of your fiercest competitors.

One persistent question could risk a paying client and a negative online review.

Accidentally Overbooking Your Schedule

As independent contractors, we get schedule-happy! A serious client agrees to meet, and in the name of business, we impulsively accept whatever time slot they offer.

The problem is that you can accidentally overbook your schedule.

Now you’re in quite the predicament.

Do you reach out to the new client again and tell them that the time they chose actually doesn’t fit your schedule after all the back-and-forth emails?

Or do you cancel your pre-existing session with a current loyal customer?

Preferably … neither.

But think of it this way:

If you can’t handle a menial task like scheduling, why should a client trust you with their $3,000 photoshoot or to manage their business’s finances?

Your reputation may take a serious hit.

What’s Left of Your Sanity

You’re not the CEO of a major corporation. Nor do you have dozens of representatives on standby ready to take over for a conference call when your schedule is jam-packed.

You’re just one person.

And all you have are 24 hours.

The mental gymnastics of finding available meeting times that don’t overlap with your currently scheduled sessions can drive you crazy. And overwhelming your mind can eventually take a toll on your quality of work.

Don’t let it … ditch the question!

Related: 10 Keys to Effective Client Interfacing

What You Should Say Instead

Okay, so now you know what you shouldn’t ask.

But that question has been your go-to scheduling lead-in for years now.

And you risk revenue by walking away from your first meeting with a client without a future appointment penned into your calendar.

Fortunately, the appointment-scheduling thing wasn’t the problem.

It was your approach.

Revamp your scheduling process by asking the following questions instead:

“I’m Free _____ , Do Any of Those Times Work for You?”

Imagine going to a brand new restaurant, not receiving a menu when you sat down, and then having the waitress ask, “What would you like to order?”

You’d probably ask, “What would you recommend?” And the waitstaff would likely read off the Thursday night specials to narrow down your choices.

Do the same things with your clients. Pick a time when you currently have openings in your schedule.

For example, you could say:

“I’m free Tuesday between 12-4, Wednesday from 9-11, and my schedule is completely open on Friday. Do any of those times work for you?”

This narrows down your client’s choices and allows them to compare certain time blocks to their own schedules.

Note: Try to stagger the times, if possible. Some people may not have any prior engagements on Tuesdays and Thursdays, while others aren’t free until after 4 p.m.

“Do You Have Time for a Quick 15-Minute Meeting?”

If a client assumes your meetings are an hour or longer, they’ll be looking for a free hour in their own calendar. Not everybody has a free hour, and clients may end up pushing the meeting off for weeks under a false assumption.

But a 15-30-minute meeting … that’s far more reasonable.

Here’s how you can phrase it:

“I was thinking we could meet for a quick 15-minute meeting this week. Can you fit me into your schedule?”

Chances are, your client has a little extra time during their lunch break or in-between their own appointments to give you a call.

How Would You Like to Meet?”

Face-to-face meetings are great for building a strong relationship the first time you meet a client. After all, there’s no digital equivalent to the firm handshake, steady eye contact, and shared smiles from an in-person appointment.

But this is not always realistic, especially with the ongoing COVID pandemic and lengthy travel times needed to get to a central meeting location.

So, change the scope of the question to:

How would you like to meet?”

Then give your clients several options like:

  • Phone call
  • Video call (Google Meet, GoToMeeting, Zoom call, etc.)
  • Conference call (if you want other independent contractors on the line)

Try to avoid text, chat, and email conversations if you can. It’s easy to misconstrue these written messages, and it could take hours to “finish” your digital meeting rather than a brief 15-minute phone call.

Is Square Appointments enough for your business? Get the facts in our Square Appointments review.

“I Was Thinking We Could Meet at _____  on _____. Can You Make It?”

Some clients prefer that you be even more specific about when you’d like to meet. After all, some people just aren’t confident in their decision-making skills.

Ask about a more specific time slot.

Here’s an example:

“I was thinking we could meet at 11 a.m. on Friday to plan out the next session. Does that time work for you?”

Of course, that exact phrasing isn’t required.

You can finish the question with “Will you be able to make it?” or “Are you free at this time?” Or you can take even greater control of the scheduling with, “I’m going to pen you in for Friday at 1 p.m. Is that okay with you?”

Sometimes a yes/no question is better than an open-ended question.

This phrasing works best with the clients you already know to be indecisive. Steer clear of this one for new clients that you’re still getting a feel for, as it could trigger the back-and-forth meeting slot debate that you’re trying to avoid!

Easier Ways to Schedule Meetings

You already have enough on your plate.

Between the lead generation, project estimates, and doing your actual work, you put your ROI and efficiency on the line when scheduling takes longer than necessary.

The good news is that there are easier ways to schedule meetings, and there are a lot of tools that can make your life as an independent contractor a heck of a lot easier.

Is Acuity right for your business? Learn more in our Acuity Scheduling Review for Freelancers and Contractors

The Best Apps for Scheduling Meetings

Efficient ways to schedule meetings

Scheduling meetings can be so hectic that you’ve even wondered, “How much does it cost to hire a personal assistant?”

But while hiring a virtual assistant or a social media manager can certainly help you scale your business, it might not be the smartest choice right now.

Before you bring on any new team members, try using one of these high-end scheduling apps to get your calendar under control. There’s no longer a need to keep a hard copy of your schedule!


Bloom is one of the most efficient scheduling assistant tools to invest in as an independent contractor or small business owner.

All you have to do is send out a link to your calendar through your marketing emails, Facebook page, or Instagram profile. You can even publish a client intake form on your website and book meetings there.

Then, your client can fill out the required fields and select the time that best works for them. Bloom will automatically pen their appointment into your schedule in real-time and send both of you email reminders up until the day of the meeting. No more overbooking appointments, playing phone tag, or being stood up by a forgetful client.

Quick, easy, and affordable! No more scheduling nightmares!

Try Bloom free for 14 days!

Facebook Business Appointments

Anybody who owns a startup or is an independent contractor needs a Facebook Business page. These pages also happen to make scheduling meetings a breeze.

Thanks to the Appointments feature, you can set your availability, make your openings visible to clients, and allow them to schedule meetings directly in the app.

Facebook will then automatically add this new meeting to your Google Calendar.

All without having to dial a single phone number!

Google Calendar

You might already use Google Calendar to track your upcoming client meetings.

But did you know that you can also open up your calendar for clients to choose their own appointment slots? Send out a welcome email to your client and let them choose a time that works best for them.

When they book an appointment, Google automatically sends them a reminder along with a printable schedule (in case they’re old school).

Regular Calendar invites were so last year.

Check out our reviews of some other popular scheduler apps for iOS and Android:

Calendly | Square Appointments | Acuity Scheduling | Dubsado

Creating Blocks in Your Schedule Strictly for Meetings

The last thing you want as an independent contractor is to let your clients run your life. You schedule conference times that fit into their calendar and sacrifice your prized free time to keep the opportunity of a sale alive.

Don’t sell your soul!

Instead, block out times in your schedule that you can dedicate strictly to meetings.

Nothing more, nothing less.

If Thursday rolls around and your meeting slots are still open, use that time to ensure next Thursday is full. Spend the hour generating leads or calling past clients to ask about referrals.

How does Calendly compare to other scheduling tools? Find out in our 5 best Calendly alternatives review.

Scheduling Meetings in a Timely Manner

Try to schedule meetings too far out, and either you or your client will forget about it. Or, one of you will make the embarrassing mistake of overbooking.

And let’s be honest, some of us don’t know what we’re doing for lunch or this weekend, let alone an entire month from now.

We call it “living in the moment.”

But if you try to schedule your meeting an hour or even a day in advance, you run the risk of showing up unprepared or without an open spot in your client’s schedule.

Pro tip: Look for the sweet spot—about a week out, if possible.

Sending Off Meeting Agendas Beforehand

When you get the dreaded “Hey, we should talk” message from your significant other, sheer terror sets in.

It could be a surprise trip to Disney, but they also may be trying to let you down easy.

Meetings and appointments can be nerve-wracking for new clients, especially if they’ve never booked services with someone in your industry before.

The solution: Send out a meeting agenda beforehand, laying out the topics you plan to discuss. That way, your client can breathe a sigh of relief, won’t be caught off guard, and can arrive at the meeting having done their homework.

See also: The Best Time Organization Hacks for Freelancers


You risk a lot by asking clients, “What time works best for you?”

Finding a mutual opening in both of your schedules can be frustrating for all parties involved.

So next time you catch yourself asking this anger-inducing question, rephrase it.

Say, “I was thinking we could meet at ___ on ___. Can you make it?” instead.

Or even better … rely on your CRM to seamlessly schedule your future appointments with clients—without the headache of asking, “What time works best for you?”

Bloom isn’t just another piece of scheduling software—it’s an all-in-one CRM solution. Learn more about pricing options and find out how Bloom can help you grow your business!

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