3 Things You Should Do When Asking Someone for Their Time

Do you suck at scheduling meetings?

Luis Vazquez
6 min readAug 20, 2020

How many meetings have you attended in your lifetime?

Too many meetings to count.
— your brain answering that question.

Yeah, you won’t even try to count them. Okay, let’s narrow it down further. I’m willing to bet you’ve had at least 3 meetings in the last 5 days. And I’m almost sure you initiated and scheduled at least one of those meetings.

You’ll have meetings for the rest of your life — no matter how you feel about them.

Asking for someone’s time simply comes with the territory of freelancing. You’ll initiate meetings with prospects, clients, collaborators, and sometimes, a good old fashioned business crush.

Time is precious. And we should treat it as such — especially when asking someone for their time.

How Good Are You at Asking for Someone’s Time?

The reality is that most people are horrible at scheduling meetings. Maybe you do too and don’t know it.

Check to see if any of the following rings true for you:

  • It takes you more than 2 interactions to schedule a meeting. Every interaction chips away at the “yes” you’re looking for.
  • You write more than 7 sentences when asking via email — it better be less than that via text!
  • You rarely meet with people out of your league. In this case, “out of your league” means whomever you’re intimidated by.

If any of those scenarios are true for you, it’s time to change that.

You’re Probably Asking The Wrong Way

Yes, people are indeed busy and important. But don’t use these facts as excuses. Instead, frame your approach accordingly. Plus, if these things were truly an obstacle, then we’d have little use for coffee shops and restaurants. And we both know the world doesn’t work that way — even for us introverts.

If people aren’t giving you their time, then you’re probably asking wrong.

What? I’m polite. I’m clear and direct. How on earth am I asking wrong?!

Before you beat me with a stick for defamation, let’s dig into 3 things you should do when asking someone for their time. I’ll make it up to you by providing some examples too.

1. Incentivize Them

When you meet with someone, by default, you’ve withdrawn your time from everyone else in the world — including yourself — for the duration of that meeting. The same applies to someone who agrees to meet with you. Neither of you can be in more than one place at a time.

It’s quite special if you think about it. This is why it’s only right to justify the meeting by providing some kind of incentive.

This is easy as a freelancer. If you truly aim to serve through your business, then a meeting with you is always beneficial. When you meet with someone, remind them of that benefit.

What changes for them after the meeting? What will they get from you that will propel them forward? Specify as much as you can.

Sometimes, you’ll meet with people who won’t benefit as much as you do from a meeting. That’s okay, but don’t let it be the norm. In such a case, at least offer to buy them food or coffee in exchange for their time.

The point is to communicate that you understand the preciousness of their time. It’s your job to convince them you won’t waste it. On the contrary, you’re worth every bit of their time.

Stereotypical Approach:

Let’s meet and talk more about what you need.

Better Approach:

It seems like I can help you with problem x. Let’s meet and talk more about specifics. Meanwhile, I’ll make a list of questions and possible high-level solutions. We can discuss them when we meet.

Do you see the difference?

The stereotypical approach is too vague. Talking about someone’s needs doesn’t guarantee a time well spent — even if you’re a boss freelancer.

The better approach is specific. It gives a “worth your time” kind of vibe and paints an attractive picture of progress.

2. Propose Two Meeting Times and at Least One Meeting Place

I have a good friend who started freelancing a few years ago. Every time I see him, he asks to meet with me for advice on this and that. I always agree to meet with him but we never end up meeting.

Do you know why?

Because he hasn’t given enough thought to the details of scheduling the meeting. It doesn’t make sense for me to coordinate our schedules. I’m not asking for his time. He’s asking for mine. It’s his job to figure out the when, where, and why.

I promise I’m a good friend, even if I’m putting him on blast, heh.

If you want meetings to happen, then always propose two meeting times and at least one meeting place. You’ll prevent a lot of back and forth interactions, which drain people.

Be decisive with proposing times and places. Do the hard work for them.

I blame laziness and insecurity as the two main culprits of indecisiveness — especially when scheduling meetings. Lazy people want someone else to decide the details for them. Insecure people don’t want to propose details out of fear of rejection.

Stereotypical Approach:

When are you available to meet?

Better Approach:

Does Wednesday at 11 am at coffee shop X work for you? Or does Thursday at 2 pm (same place) work better?

The stereotypical approach is passive. It asks an open-ended question and makes the other person work too hard. It doesn’t seem right that someone should figure out the details of a meeting you’re requesting.

Also, a meeting place is yet to be discussed. This will add the dreaded back and forth interactions that dwindle the chances of a meeting.

The better approach does the exact opposite. You’re asking the person to choose an option — that’s easy. If the time or place doesn’t work, most people will follow your lead. They’ll propose something that works for them. This eliminates any back and forth interaction upfront.

3. Make It Easy for Them

This last tip gets to the heart of this article. People lead busy lives. They don’t want complications. So, whatever you do, don’t complicate their life. They will avoid you like a plague — are those even avoidable?

How can you make it easy for them to meet with you?

Let’s cover some basics that will make their lives easier and work to your advantage.

Send a calendar invite

People sometimes forget to add events to their calendar. It’s such a manual process for most of us unless you use an AI assistant such as Siri, Alexa, or Google.

Do you really want a prospect or client to go through the trouble of opening up their calendar, searching for the day, then the time, writing the event name, and then eventually, having to decipher the spelling of your name? Or would you rather just have them click “yes” to a calendar invite?

Having your name on someone’s calendar is a privilege. A person thinks twice before double-booking. They’ve declared themselves unavailable to everything and everyone else except you for that time slot.

Another advantage is that they’ll receive a nice little reminder beforehand, which leads to the next tip.

Send relevant information ahead of time

I can’t tell you how many times I’ve attended meetings with no clue what to expect. It’s not because I’m a procrastinator or a mess, either. It’s because I’m busy and keep track of many things — just like you.

Sending a meeting agenda gets everyone on the same page. You can add it to the calendar invite you sent when asking for their time. Attendees will receive an email when the event has been updated.

The key is to help the person prepare for the meeting. The meeting will naturally spark deeper and more focused conversations. It’ll also shorten or lengthen your meeting time in good ways.

Lastly, choose an accessible location

Don’t make people work harder than they need to.

If you live across town, then do most of the driving. Choose a place where it’s easy to find parking unless the person is walking distance from the meeting location.

If you’re meeting online, then choose easy-to-use software. Don’t make someone sign up for something they’ll only use once. Zoom meetings are the new norm since COVID19. Use that.

People like smooth transitions and hate complications.

Embrace a Better Approach

Mastering the skill of asking for someone’s time is game-changing. Meetings can deepen relationships and move projects forward.

If you learn to ask right, people will gladly meet with you.

Be decisive, be considerate, and make things easy for others. These are great qualities to have in general. Incorporate them when asking for someone’s time. People will gladly share their time with you.

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Luis Vazquez

I write stories about cities, freelancing, and facing your demons. Current projects: mightyintrovert.com