The unspoken power dynamics of Calendly

"You're asking me for a favor, and you want me to schedule around you? GTFO.”

Dec 13, 2023

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In this week’s newsletter, we’ll cover how to send a Calendly link without seeming entitled. This might seem minor or tactical, but power dynamics exist in your daily work and being aware of them will make you a savvier operator. Enjoy.

Read time: 12 minutes

Imagine you’re a 22-year-old founder cold emailing Marc Andreessen to say, “I want to meet you. Pick a time from my Calendly.”

Imagine you’re a salesperson sending mass DMs to busy managers to say, “I’m spamming you, but my convenience takes precedence.”

Imagine being a candidate reaching out to a hiring manager to say, “I want to pick your brain for free, but we should prioritize my schedule.”

Obviously, this sounds absurd. And yet exchanges like these happen every day. Every day, good people accidentally shoot themselves in the foot because they sound entitled asking people to schedule around them.

So here’s a question: How do you use Calendly without seeming like a pompous jerk who thinks their time is more important?

Why this matters

I’ve heard folks say they want to use a calendaring tool, but are worried it will be awkward. In the past few years, there’s been debate (including this viral tweet) about whether calendar links are a power move.

Here’s my take: If you're making an appointment at the doctor's office, of course you'd expect an automated appointment system. But if you're pitching to customers or investors, you might rightfully feel self-conscious asking them to choose a time that fits your schedule.

This might seem minor, but it’s important because:

Power dynamics exist. Scheduling is simply one expression of power dynamics. If you brush it off here, you’re likely missing it in other instances that are more significant.
Multiple times a day, dozens of your employees are pitching, emailing, and DMing with folks outside your company. If you’re not aware of how they’re perceived, they could be turning off customers without even knowing it.
If you’re a small organization, you don’t have many levers—your words are one of the few levers for shooting your shot.
If you’re a larger organization, you want to be mindful of your brand as you scale. Some companies seem warm and human, whereas others seem sterile, bureaucratic, and cold.
The way you come across for seemingly small things—like scheduling a meeting—impacts the way you’re viewed by others. They are tacit clues that indicate your finesse, self-awareness, and level of judgment.

I wrote an internal-only version of this post in 2021 when calendaring links were less popular than they are now. I shared it with my team to teach employees about power dynamics in writing. Even though Calendly is more widely accepted now, this is a good way to explain underlying power dynamics that occur in daily communication.

Power dynamics exist. Ignore them at your own peril.

When you ask your recipient to pick around your schedule, you’re implicitly asserting a power dynamic. Traditionally, the less powerful person accommodates the more powerful person. You might be trying to be proactive and efficient by sending a calendar link, but this action has the side effect of implicitly asserting you’re more powerful. This is why people can feel put off. They might not be able to articulate this, but it’s because you’re breaking a norm.

Therefore, you need to counterbalance by sounding friendlier—the extra warmth signals that you’re coming from a good place and not trying to dominate. If it’s not your intent to seem demanding, it's even more important to avoid giving the wrong impression.

For example:

Before: “Let’s schedule a call. Here's my availability.”
After (if you’re close in power): “I'd love to schedule a call. Would any of these times work for you?”
After (if there’s a big differential in power): "I'd love to schedule a call. Would you want to take a look and see if any of these times work for you?”

Phrases like “for the sake of ease,” “do you mind,” “would you want to,” “take a look,” and ending on “you” all sound friendlier.

I recommend phrasing as a question when possible because it’s more polite than a command sentence structure. If you read your writing in a robot voice, you’ll see how command sentence structures inherently sound, well, commanding.

The “ after” versions are slightly longer, and that's intentional. I'm not optimizing for being concise at any cost—I'm optimizing for getting a yes. If it takes a few extra words to sound self-aware and humble, I'm doing that. Some of the wording might sound almost too warm in isolation. But given the context that you are asking folks to pick around YOUR schedule, you need to counterbalance by being a bit nicer about it.

Offer to pick from their Calendly

If you want to be conservative, the safest bet is to offer to pick from the other person’s Calendly because it’s clearly centered around them. This is what I do in 90% of situations if I’m asking for the meeting. I’ll say:

“Do you have a Calendly? Happy to pick from that, or I can send over a few times is that’s easier.”

For example, here’s a note I sent via Twitter DM recently:

There are situations when you’re scheduling a bunch of similar meetings (for example, customer calls), and the power dynamic is a bit more even. In that case, it might be more acceptable to share your Calendly first. If you want to be conservative though, you can break your ask into two parts:

Should I send over my Calendly if that’s easier for you? Happy to pick from your calendar too so let me know.

This works because you’re getting their buy-in first, then sending your calendar link. Breaking an ask into two parts is helpful in other situations, too, and is generally an underutilized tactic. For example, I try to do this when asking for advice. Instead of sending a long email or text, I’ll first ask, “Can I get your advice on something?” If they say yes, I’ll send more information. This feels more respectful of the person’s bandwidth, and gives them a chance to reply before you off-load onto them.

If you think doing this in two steps is inefficient or creates more work for your recipient, it doesn’t really. Not all emails are created equal. Most people reply very quickly to emails when they know what they want to do. If they get your note, they’ll “sure, send it over.”

More importantly, who cares about efficiency is the person feels miffed? The goal is to get a yes. If an extra email increases the chances your recipient feels goodwill toward you, keep your eyes on the prize.

Anatomy of a respectful ask

The script below looks simple, but I want to dissect why it work so you see the levers at play:

After: “I'd love to schedule a call. Do you mind taking a look to see if any of these times might work for you? Please let me know if you have other dates in mind. Happy to schedule around what's best for you.”
After, shorter option: “I'd love to schedule a call. Do you want to see if any of these times work for you? Happy to pick from your Calendly if that’s easier for you.”

Within a few short sentences, I’ve shown that I’m happy to schedule around the other person:

“I’d love to schedule a call” is friendly and enthusiastic. It shows good faith.
“Do you mind” is slightly wordier than “could you,” but we’re not optimizing for being concise at any cost. We’re optimizing for a positive reaction from our recipient. “Do you mind” sounds self-aware and humble.
The “might” in “might work for you” is stylistic. You could go without it, but I like adding it because it comes across a bit warmer.
“Happy” and “you” are good words to start and end with because the eye is naturally drawn to the first and last words of a sentence.
“What’s best/most convenient/easiest for you” emphasizes prioritizing your recipient.

Overall, the note comes across as respectful and conversational because we stuffed it with positive keywords that pop when you skim.

A note like this works for many types of interactions, including with folks outside your team where you want to put your best foot forward. The outcome is the recipient feels seen and heard—and more likely to actually pick a time from your calendar.

If you’re asking for a meeting, err on the side of being polite

When people are too curt with their Calendly links, sometimes I have a visceral reaction of, “Really? I'm doing a favor taking this meeting. Why am I scheduling around you?” You don't want your prospective customers to come away with this negative reaction. Most people won’t admit to thinking this because it makes them appear petty, but it doesn’t make the reaction any less real.

Recognizing this is even more important if the other person thinks they are more powerful. An abrupt note will feel more jarring for them, whereas someone less powerful would assume they should schedule around you anyway.

This isn’t about whether power dynamics exist. They do. It’s about how they come into play in moments you might not realize, and the repercussions if you misread.

People want to feel respected. We don’t like when people (especially people in no position to make demands) demand things of us. There’s a lot of upside to erring on the side of being more polite. There’s a lot of downside to misreading a situation and coming across as entitled.

If you’re a respectful person, it’s a shame if your recipient thinks you’re entitled. You may lose opportunities before you even have a chance to interact. Luckily, once you know the underlying logic, it’s simple to add warmth to your note. Here are additional scripts you can mix and match:

“Here’s my Calendly in case any of these times work, but feel free to send over your link and I can pick from there.”
“Please let me know if you have trouble finding a time and we can definitely figure something out.”
“Feel free to send your Calendly, or let me know if I should send mine if that’s easier.”
“Would any of these times work for you to connect in the next few weeks? Happy to work around your availability, so let me know.”

If you read these in a robot voice with no facial expressions or tone of voice, it still sounds friendly. You don't know if your recipient is reading your note on a bad day or in a surly mood. That's why you need to write in a way where the words themselves convey warmth. If there's a chance of misinterpretation, rewrite it.

These scripts are all ways to achieve the same goal: to get the time savings of sharing your Calendly link while showing that you’re flexible, accommodating, and value your recipient’s time.

Remember: People don’t owe you anything. They don’t owe you a meeting. They don’t owe you their time. They don’t owe you a response. If you’re making a request to someone who could say no, it behooves you to make them want to engage with you. And if you happen to be the more powerful person in a dynamic, it doesn’t hurt to be warm either—it makes you appear gracious.

Case studies: Four real-life examples

Here are examples of scheduling exchanges, including with people who are successful enough that you’d understand if they were demanding. But they are approachable and humble, so it’s no wonder they are so well-loved.

Nir Eyal, best-selling author

Notice how warm Nir is. When he shares his Calendly, he says “for the sake of ease,” which is humble and unassuming, even though he's more famous than many random people I’ve interacted with who are demanding.

Lenny Rachitsky, Substack writer, podcaster, investor

Here's what I said to Lenny via iMessage when I first met him in November 2020:

Hey Lenny! It's Wes from Didactic (the original name of my company Maven). Want to do a call about your potential course this week? Let me know and I’ll send some times to see what's good for you.

Notice I said “I'll send some times over” to take on the responsibility of scheduling and to make his life easier. I didn’t want him to have to do more work because (a) I was the one asking for the meeting and (b) any friction could delay setting up the conversation. Then I intentionally ended with “to see what's good for you” to reinforce that I want to prioritize his schedule.

When Lenny replied, he proactively acknowledged the awkwardness of him sending me his Calendly. He says "the awkward but still handy Calendly." This is pretty endearing, especially for someone of his stature, and speaks to why so many folks root for him.

Note to a high-profile customer

I dug up my initial email to a high-profile instructor that our lead investor at First Round Capital introduced us to. I shared my Calendly with this instructor because I felt confident that my note was warm and enthusiastic enough.

For me, it comes down to how my target audience will receive the note. If there’s even a slight chance the person might be rubbed the wrong way from a Calendly link, I won’t do it. It’s simply not worth decreasing the chances of closing a sale if we might start off on the wrong foot.

There are several details in here that added warmth without relying on a single exclamation mark. How did I do this?

Establishing my admiration of their work and our mutual connections
“For the sake of ease” is humble and self-aware
“Do you mind” instead of “could you.” “Could you” is more concise, but being concise means nothing if your intent gets lost in translation because your recipient felt like you sounded demanding.
Ending the paragraph on “you”
Proactively acknowledging if she has trouble finding a time that I’m happy to pick from her calendar

The instructor ended up picking a time and we had an amazing call. This individual is still a thriving instructor on Maven’s platform today.

Example of a note that almost works, but not quite

The note below is from a reader. I’m thankful he shared it because we can dissect it and learn from it. Here’s the note:

"If you happen to have 15 minutes in the coming weeks, I'd love to have a quick Zoom or phone call. Shoot me an invite and I'll make myself available. (And in case it's convenient for you, here's my availability calendar, you can just grab a time)."

On the surface, it seems to check all the boxes. It’s definitely decent, and he does some things right.

Pros of this note:

Phrases like if you happen to, I’d love to, quick, in case it’s convenient for you are easy to skim and feel considerate.
I can tell he’s putting forth effort, and if I give the benefit of the doubt, he seems like a sincere dude.

Cons of this note:

The premise of the ask itself: I don’t have full context, but this sounds like a cold pitch. If so, your recipient could be getting dozens of coffee chat requests per week. So this is a bigger ask than you think.
Shoot me an invite - I have to shoot you an invite? I thought you wanted this meeting. I know the writer didn’t mean anything bad by this, but I’m withholding the benefit of the doubt because it’s not guaranteed with your reader.
I’ll make myself available - Wow, I’m so glad you’ll make yourself available for the meeting you wanted… Again, I know the writer meant to be gracious here, but it can sound like he thinks he's doing me a favor.
You can just grab a time - Making something sound easy can backfire because it diminishes the effort involved. “Just grabbing a time” isn’t the hard part—the hard part is whether to block off time in my packed schedule to meet with you. You want to honor that, not downplay it.

I’m being a bit of a stickler on purpose because I want to point out how this note could be read, especially by a stranger who’s hearing from you for the first time. You can still say the things he says here because it’s not egregious. Or you can take 30 seconds and fix anything that might be misread.

Playing high vs playing low

Years ago, I saw this video of a Stanford Graduate School of Business professor talking about the psychology of power and influence, especially the concept of playing high vs playing low. Playing low is where you acknowledge the other person is more powerful than you are.

When I talk about acknowledging power dynamics and being respectful, I'm not saying you should be overly deferential or ingratiating. There’s a spectrum—obviously don’t go to the furthest end of the spectrum and make yourself seem more junior than you are. Your note should be friendly, but direct and professional. In general, I tell my team to assume you're more equals than not equals because you don't want to give away your power unnecessarily. But at the same time, use word choice to help show warmth and signal that you are aware of the dynamics.

For example, the CEO of a publicly-traded company might reply in one to three words to you. Does that mean you should only write "Ok” when replying to their emails? No, that would feel weird and disrespectful. Does that mean you have to write a 750-word gushing essay as a response? Also no. Use your best judgment, while erring on the side of warmth when in doubt.

I’ve heard investors tell their founders not to use Calendly when fundraising because it’s easy to accidentally have prospective investors think you’re on a high horse. So founders may want to manually schedule to avoid the slight chance that investors thought you might be "playing high.”

Substitute “On Deck” for any other institution with 21-year-old founders

Surprisingly, many successful people are warm and gracious. It's usually tech bros who reach out with an entitled attitude.

A few questions to consider as you assess the power dynamics:

Who is more powerful?
Who thinks they’re more powerful?
Who needs the meeting more?
Who is asking and hoping for a yes?
Who is in a position to say no?

The bigger the power differential, the more you should lean toward being respectful. The closer the power dynamics, the more you can be a bit more casual in your communication because it’s not obvious who should accommodate whom.

Takeaways and action items

It’s shockingly easy to have misunderstandings in written text. Examine how you send calendar requests. You may want to share this post with your team, so you can align on how to put your best foot forward when scheduling with clients, customers, etc.

Takeaways:

Many people are happy to use your Calendly if you ask in a thoughtful way.
If using a tool would make scheduling faster but your recipient thinks you’re an asshole, you win the battle but lose the war.
If you’re asking for a meeting, err on the side of being polite.
Offer to pick from the other person’s Calendly—or get permission first, then send your Calendly.
The bigger the power differential, the more you should be accommodating. If there is no power differential (you are peers) or you’re more powerful, you can be more direct.
Sending a calendar link might disrupt your recipient’s expectations, so counterbalance by adding more warmth than usual to your note.

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Thanks for being here,
Wes Kao

PS See you next Wednesday at 8am ET.