The unspoken power dynamics of Calendly
"You're asking me for a favor, and you want me to schedule around you? GTFO.β

π Hey, itβs Wes. Welcome to my weekly newsletter where I share frameworks for becoming a sharper marketer, builder, and founder. If youβre not a subscriber yet, hereβs what you missed:
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In this weekβs newsletter, weβll 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:Β 12 minutes
Imagine youβre a 22-year-old founder cold emailing Marc Andreessen to say, βI want to meet you. Pick a time from my Calendly.β
Imagine youβre a salesperson sending mass DMs to busy managers to say, βIβm spamming you, but my convenience takes precedence.β
Imagine being a candidate reaching out to a hiring manager to say, βI want to pick your brain for free, but we should prioritize my schedule.β
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 hereβs a question: How do you use Calendly without seeming like a pompous jerk who thinks their time is more important?
Why this matters
Iβve heard folks say they want to use a calendaring tool, but are worried it will be awkward. In the past few years, thereβs been debate (including this viral tweet) about whether calendar links are a power move.
Hereβs 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 itβs important because:
Power dynamics exist. Scheduling is simply one expression of power dynamics. If you brush it off here, youβre 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 youβre not aware of how theyβre perceived, they could be turning off customers without even knowing it.
If youβre a small organization, you donβt have many leversβyour words are one of the few levers for shooting your shot.
If youβre 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 thingsβlike scheduling a meetingβimpacts the way youβre 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, youβre 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 youβre more powerful. This is why people can feel put off. They might not be able to articulate this, but itβs because youβre breaking a norm.
Therefore, you need to counterbalance by sounding friendlierβthe extra warmth signals that youβre coming from a good place and not trying to dominate. If itβs not your intent to seem demanding,Β it's even more important to avoid giving the wrong impression.
For example:
Before: βLetβs schedule a call. Here's my availability.β
After (if youβre close in power): βI'd love to schedule a call. Would any of these times work for you?β
After (if thereβs 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?β
Phrases like βfor the sake of ease,β βdo you mind,β βwould you want to,β βtake a look,β and ending on βyouβ all sound friendlier.
I recommend phrasing as a question when possible because itβs more polite than a command sentence structure. If you read your writing in a robot voice, youβll see how command sentence structures inherently sound, well, commanding.
The β afterβ versions are slightly longer, and that's intentional. I'm not optimizing for being concise at any costβI'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 personβs Calendly because itβs clearly centered around them. This is what I do in 90% of situations if Iβm asking for the meeting. Iβll say:
βDo you have a Calendly? Happy to pick from that, or I can send over a few times is thatβs easier.β
For example, hereβs a note I sent via Twitter DM recently:
There are situations when youβre 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 thatβs easier for you? Happy to pick from your calendar too so let me know.
This works because youβre 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, Iβll first ask, βCan I get your advice on something?β If they say yes, Iβll send more information. This feels more respectful of the personβs 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 doesnβt 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, theyβll βsure, send it over.β
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: βI'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.β
After, shorter option: βI'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 thatβs easier for you.β
Within a few short sentences, Iβve shown that Iβm happy to schedule around the other person:
βIβd love to schedule a callβ is friendly and enthusiastic. It shows good faith.
βDo you mindβ is slightly wordier than βcould you,β but weβre not optimizing for being concise at any cost. Weβre optimizing for a positive reaction from our recipient. βDo you mindβ sounds self-aware and humble.
The βmightβ in βmight work for youβ is stylistic. You could go without it, but I like adding it because it comes across a bit warmer.
βHappyβ and βyouβ are good words to start and end with because the eye is naturally drawn to the first and last words of a sentence.
βWhatβs best/most convenient/easiest for youβ 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 heardβand more likely to actually pick a time from your calendar.
If youβre 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, βReally? I'm doing a favor taking this meeting. Why am I scheduling around you?β You don't want your prospective customers to come away with this negative reaction. Most people wonβt admit to thinking this because it makes them appear petty, but it doesnβt 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 isnβt about whether power dynamics exist. They do. Itβs about how they come into play in moments you might not realize, and the repercussions if you misread.
People want to feel respected. We donβt like when people (especially people in no position to make demands) demand things of us. Thereβs a lot of upside to erring on the side of being more polite. Thereβs a lot of downside to misreading a situation and coming across as entitled.
If youβre a respectful person, itβs a shame if your recipient thinks youβre entitled. You may lose opportunities before you even have a chance to interact. Luckily, once you know the underlying logic, itβs simple to add warmth to your note. Here are additional scripts you can mix and match:
βHereβs my Calendly in case any of these times work, but feel free to send over your link and I can pick from there.β
βPlease let me know if you have trouble finding a time and we can definitely figure something out.β
βFeel free to send your Calendly, or let me know if I should send mine if thatβs easier.β
βWould any of these times work for you to connect in the next few weeks? Happy to work around your availability, so let me know.β
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 youβre flexible, accommodating, and value your recipientβs time.
Remember: People donβt owe you anything. They donβt owe you a meeting. They donβt owe you their time. They donβt owe you a response. If youβre 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 doesnβt hurt to be warm eitherβit makes you appear gracious.
Case studies: Four real-life examples
Here are examples of scheduling exchanges, including with people who are successful enough that youβd understand if they were demanding. But they are approachable and humble, so itβs no wonder they are so well-loved.
Nir Eyal, best-selling author
Notice how warm Nir is. When he shares his Calendly, he says βfor the sake of ease,β which is humble and unassuming, even though he's more famous than many random people Iβve 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 Iβll send some times to see what's good for you.
Notice I said βI'll send some times overβ to take on the responsibility of scheduling and to make his life easier. I didnβt 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 βto see what's good for youβ 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 thereβs even a slight chance the person might be rubbed the wrong way from a Calendly link, I wonβt do it. Itβs 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
βFor the sake of easeβ is humble and self-aware
βDo you mindβ instead of βcould you.β βCould youβ 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 βyouβ
Proactively acknowledging if she has trouble finding a time that Iβm 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 Mavenβs platform today.
Example of a note that almost works, but not quite
The note below is from a reader. Iβm thankful he shared it because we can dissect it and learn from it. Hereβs 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. Itβs definitely decent, and he does some things right.
Pros of this note:
Phrases like if you happen to, Iβd love to, quick, in case itβs convenient for you are easy to skim and feel considerate.
I can tell heβs 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 donβt 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 didnβt mean anything bad by this, but Iβm withholding the benefit of the doubt because itβs not guaranteed with your reader.
Iβll make myself available - Wow, Iβm so glad youβll make yourself available for the meeting you wantedβ¦ 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. βJust grabbing a timeβ isnβt the hard partβthe hard part is whether to block off time in my packed schedule to meet with you. You want to honor that, not downplay it.
Iβm being a bit of a stickler on purpose because I want to point out how this note could be read, especially by a stranger whoβs hearing from you for the first time. You can still say the things he says here because itβs 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. Thereβs a spectrumβobviously donβt 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 "Okβ 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.
Iβve heard investors tell their founders not to use Calendly when fundraising because itβs easy to accidentally have prospective investors think youβre on a high horse. So founders may want to manually schedule to avoid the slight chance that investors thought you might be "playing high.β
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 theyβre 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 itβs not obvious who should accommodate whom.
Takeaways and action items
Itβs 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 youβre an asshole, you win the battle but lose the war.
If youβre asking for a meeting, err on the side of being polite.
Offer to pick from the other personβs Calendlyβor 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 youβre more powerful, you can be more direct.
Sending a calendar link might disrupt your recipientβs expectations, so counterbalance by adding more warmth than usual to your note.
Iβd love to get your help growing our community of thoughtful, rigorous operators. If you found this valuable, consider subscribing if you havenβt already, or take a moment toΒ refer a friend. Use your unique link here:
Thanks for being here,
Wes Kao
PS See you next Wednesday at 8am ET.
Thanks you for your post! Intuitively knew it, but helpful to sharpen messages. π
Just yesterday I had this internal debate.
Finally, I sent my scheduling link but added: βIf you donβt find a suitable spot, please let me know your availability.β