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While I do find the back and forth of finding a date to meet one of the most mind numbing tasks one can do, I think the author here is placing way too much importance on this CEO’s actions. Would he still write the same if the ceo used a bot to perfectly impersonate the ceo?
I agree with the author's point here. I've long considered it a red flag if I've been contacted by someone to do something for them, but then get pawned off on someone else to work out the details.

That tells me either that the person who contacted me is just being used for their name -- in which case I'm being manipulated -- or that the organization is so large and bureaucratic that I'm going to have further complications dealing with them.

> Would he still write the same if the ceo used a bot to perfectly impersonate the ceo?

I don't know about the author, but I would consider this to be even worse.

What about people like me who literally just don’t know our own calendar? I mean I know that it’s near full and I know there are still open slots, but it’s just too inefficient to start trying to plan a date with someone else when I don’t know either of the two calendars I’m trying to find a common hole in. Why not just pass that off to the person who actually knows my calendar?
That falls under the "too bureaucratic" item I listed. I'm not saying that your practice is wrong and shouldn't be used, I'm saying that it is a sign that I'm more likely to have further difficulties with your company and makes it less likely that I'll take part.

EDIT: There is a way to accomplish the same end result without triggering my spidey-sense, though... it's for the too-busy executive (such as yourself) to not be the one to contact me. Have a more-available subordinate be my primary contact from the get-go. They can then arrange a meeting with the executive as a sort of side benefit. That way, the person that I have the relationship with is the one who has time for that interaction, and I won't be getting "pawned off".

Efficiency and human relationships don't necessarily go together. I agree with the author that delegating the contact for a meeting where you are asking for help comes off like you're not invested. It's just a perception; it might not reflect the reality of the situation. But that's how it strikes me.

I'd argue that you could probably just look up your calendar in whatever system your assistant uses.

Or just not get po’d by it.
I know some people have busy lives and back-to-back meetings. I'm not one of them. I'm having trouble understanding why they need someone to do their scheduling for them.

Shared electronic calendar software has been around for a while now, and there's only so many hours in the day...

What am I missing that means you can't personally schedule your own time with a customer or supplier ?

Isn't it just a case of opening your calendar app and finding a mutually agreeable half hour in there somewhere ?

If you don't know your own calendar, then I do not want to talk to you.

I would rather talk to the person who knows and controls your calendar. They are the true source of power and they are the one who can actually get things accomplished.

I will agree with you 1000% that I really hate getting pawned off. But I don’t think you can draw a particular conclusion from it. A lot of times ceos just want their team to get their arms around things quickly. There’s no reason you can’t Come back to the ceo and maintain a direct line of contact. I find that often if there’s a particular process for accessing the ceo, it’s much better to learn it and leverage it. I just don’t think there’s much to be gained by getting offended by how someone chooses to organize themselves. Better that than the person who over commits and flakes half the time.
While the general advice feels sound, the point of doing small talk as part of the scheduling was not explained clearly enough for me.

It's not going to convince anyone to do things for the other person. It doesn't send the message that the meeting is urgent or important, and nothing about it will help getting both parties closer to the objective. It sounds like it would be better replaced by pleasantries that are actually related to the meeting, like the choice of food, possibility of a follow-up meeting, etc.

From the article:

I always managed to interject a casual set of questions when I was setting up a meeting. “What type of food do you like? Do you have a favorite restaurant/location?”

What are people's thoughts on using Calendly and the like? I'm asking people for meetings a lot lately, and usually after they agree I send them a link and ask them to "find whatever time works best for you."

Practically, this seems like the nicest thing to do. They get to pick a time in my very open schedule and there's no back and forth. But emotionally, it feels like I'm giving a task to someone who just accepted to help me.

These are all 20 minute video calls, by the way.

I came here after reading the article to ask the same question as I do worry about it feeling weird.

The middle ground I've settled on is to say something like: "I'd love to meet, either give me some times that work for you can pick a time from my Calendly [link]" and then most people go for the Calendly link.

Thanks. I think I'll combine our strategies. After they've already agreed to meet, I'll ask if they want to send over times and I'll give them my link.
I am not too happy with the phrasing "Outside of a company there are two types of meetings; 1) When you want something from someone, 2) When they need something from you."

I like to think about my meetings as "1)Am I building a relationship? or 2) Is this a transaction?" If it is 1, then I would invest more of my time into this. I do not want to spend a lot of time in building a relationship with my plumber, even though I do want something from them.

I believe the author was thinking the meeting as a relationship building while the founder was treating as a transaction and hence the disconnect.

There are people tho who want to form new relationships, they start out by doing some favour to you then they expect that you reciprocate it when it doesn't go the way they want it to go, they become your enemy resorting to threat or retaliation

Transactional relationships which don't carry over to future are much better. Only thing that should carry over is "trust" not favours.

This is commonly known as "nice guy" in popular culture these days.

“We’d love to partner with Steve on getting his frameworks and templates from his books – The Four Steps and The Startup Owner’s Manual – onto our product. Can you connect us to him?”

That sounds to me like the start of some sort of relationship. If the guy just wanted info from the book, then why not just read the book?

I guess I am used to seeing a different kind of startup. The kind where the founder having an 'administrator' sounds like a bizzaro weird prioritisation of early hires.
Ok, I live in the midwest and run a startup. How do I get an audience with Steve Blank? Believe me, I know I'm not important to anyone in Silicon Valley (welcome to flyover country!)
You email him.

... but wait - why exactly do you want to contact Steve Blank?

What does he, specifically bring to the table that Elon Musk does not?

What does he, specifically bring to the table that Javier Dauser does not?

I can tell you from experience that every successful businessman reads their own emails. Every single one. They only respond to those that make sense to them though, not every single one that they read.