The Last Mile of Scheduling: Why AI Agents Will Replace Your Calendar App

Scheduling is a staple business activity, similar to payments or email. We do it every day, several times a day. Nothing strange about it: our very life revolves around our schedule. Time is a main and inevitable measure and anchor for all our activities.

At the same time, scheduling isn't a particularly intellectual endeavor. If anything, it's more of a chore. You are not creating any value: you're just administering time so two or more people can meet and discuss something.

According to Calendly's 2024 State of Meetings report, this administrative burden has reached staggering proportions. 43% of respondents are spending at least three hours a week just scheduling meetings — that's up from 36% the previous year. For a professional earning $100,000 annually, that's $1,500 worth of time spent just on calendar coordination. Multiply that across the workforce, and we're looking at well over $100 billion in scheduling overhead alone.

So the question one may have – why the hell isn't this thing automated yet?

The Calendly Era: Availability Links as a Partial Solution

So far, the last word has been availability sharing services like Calendly or Cal.com. Over the last 5 years, these services have quietly revolutionized scheduling, becoming the de-facto industry standard and saving millions of hours.

The problem comes, as it often does, with the "last mile". There is a whole bunch of personal stuff that becomes tricky once we want to reflect it in something as limited and two-dimensional as a calendar. When is our focus time – if it's not at the same time from day to day? Which people do we want to meet asap and which would we'd rather schedule for next week – to keep our immediate calendar open for more time-sensitive stuff? How flexible are we about scheduling meetings over lunch? How much of our availability do we really want to show to a stranger?

Take a real example: You're a startup founder with three different types of meetings – investor pitches (which you want to prioritize and schedule immediately), customer discovery calls (important but can wait a few days), and vendor meetings (lowest priority). Your Calendly link shows the same availability for everyone. The result? Your calendar gets clogged with vendor calls while an investor has to wait until next week.

Or consider this scenario: You're most productive in the mornings and prefer to keep that time for deep work, but you'll make exceptions for C-level executives or urgent customer issues. Current scheduling tools can't distinguish between a junior account manager wanting a "quick sync" and your biggest client's CEO requesting an emergency call.

It seems like a lot about our schedule is quite private, and for someone else to be able to manage it for us – they have to know us really well.

The Gold Standard: Executive Assistants

This is exactly what executive assistants do!

The first thing I did when we decided to work on our scheduling solution, was to buy a bunch of Amazon gift cards and start reaching out to professional executive assistants. After speaking to several dozen of them – all exceptionally friendly and pleasant people, despite their obviously busy schedules, and even busier schedules they manage for others – I learned things I had no idea about.

I learned that most EAs work not for a single senior executive, but are rather "shared" by several people in the company, who are competing for their – EAs' – time. I learned that a good EA would, for example, remember to keep the day after a busy conference clear – to give the boss the chance to recover and reflect.

But most importantly, I learned that after an EA has scheduled a meeting, it almost never gets rescheduled. The occasions when the person comes back and says "actually, I realized that time doesn't work for me" are fewer than 1%. In other words, scheduling is one of the activities we are happy to delegate completely – provided there is someone we trust to manage our day for us.

I also learned EAs prefer Target gift cards to Amazon.

Here's what makes EAs so effective: they understand context. They know that their executive hates back-to-back meetings, needs 15 minutes before important calls to review notes, and should never be scheduled for anything substantial on Friday afternoons. They know which clients take priority, which meetings tend to run long, and when to build in buffer time for travel or mental transitions.

A skilled EA looks at a request for a Monday lunch meeting and thinks: "The boss has three back-to-back calls that morning already, there's a board meeting at 2 PM that they will need to prepare for, and this person tends to run over. I'll suggest 10 AM Tuesday instead, with a 15-minute buffer before their next commitment."

Exactly the kind of nuanced, context-aware scheduling that current tools completely miss!

The only problem is EAs are expensive. I learned that in major cities, a high-level executive assistant salary can be upwards of $100,000 or more, with an experienced, US-based executive assistant's salary averaging $35–60 per hour. The Wall Street Journal even profiled an executive assistant earning a jaw-dropping $400,000/yr. Even if you have the money – good luck finding one. As a result, about half of the time of, say, a junior associate in an investment firm or a project manager in a software company is spent scheduling and re-scheduling meetings for the more senior colleagues.

The AI Breakthrough: Personal-Level Automation

This is where the arrival of the latest-generation AI makes all the difference. AI presents the last frontier of automation – the personal level. When AI agents come to replace SaaS, a tool becomes an assistant. Instead of empowering us to make things happen faster, we now expect the things to be done FOR us entirely.

Modern AI can:

• Learn your patterns: Unlike static calendar rules, AI can observe and adapt to your actual behavior. It notices that you're more productive in Tuesday morning meetings, that you need recovery time after difficult conversations, and that you always want Thursday afternoons free for strategic thinking.
• Understand context: AI can read between the lines of meeting requests. A "quick 15-minute sync" from someone who historically runs over gets automatically scheduled with buffers. A request from your biggest client gets prioritized over routine internal meetings.
• Handle complexity: Instead of simple "available/unavailable" slots, AI can manage multiple calendars, competing priorities, travel schedules, and personal preferences simultaneously.
• Communicate naturally: Rather than forcing people to navigate booking pages, AI agents can handle the back-and-forth of scheduling via email, Slack, or even phone calls.

According to Calendly, automated scheduling is one of the top two AI capabilities workers are most excited about (49%).

The Scheduling Matrix

Let's get a bit under the hood.

Scheduling is a relatively standardizable activity: you can map pretty much every scheduling situation down to a 5x5 matrix:

What's Next: From Calendar Apps to Calendar Agents

The first generation of scheduling tools (Outlook, Google Calendar) required manual coordination. The second generation (Calendly, Cal.com) eliminated some back-and-forth but remained rigid and impersonal. The third generation will provide EA-level sophistication at software-level costs.

The question isn't whether this will happen – it's how quickly we can get there. The technology exists, the economic incentive is enormous, and the pain point affects literally everyone who works in a knowledge economy.

The future of scheduling is about intelligent agents that understand you well enough to make scheduling decisions on your behalf. And unlike the $400,000 EA, this agent will be available to everyone.