When engaging with leads through direct response marketing (email, chat, mail, anything that allows two-way engagement), you need to remember that your ldeas are being bombarded and harassed by marketers who don't understand goodwill at all.
Every time someone opens your message, they are paying you with attention and benefit of the doubt. You must reward that as much as possible, and as often as possible, by giving them value. What value? Draw a Venn Diagram of what you know and what you believe your audience to want to know, and send them stuff in the overlap.
Every time you reward them, you are depositing good will in their bank, which makes them more and more likely to open your notes (and accept more goodwill from you).
When you make a sales pitch, even if they say yes or still like you after, you have withdrawn good will from their bank. If you overdraw and go into red numbers, that's when they stop listening/reading, and unsubscribe.
Alex Becker, current owner of Hyros (used by everyone who's anyone for metrics), created a platform in 2018 for email marketing called Market Hero. While shut down now, it gave him crazy data from his own email marketing campaigns as well as all the stuff from user use.
He recommended you send 4-6 value emails for every ask email (where you pitch) as a way of ensuring a fair exchange of goodwill. Hormozi mentioned on his podcast that he believes in a 7/8 goodwill 1/8 ask ratio, so if he ran a 60 minute podcast, he would be super careful to keep his CTA pitch to under 7 minutes, and only at the end.
The cool thing about this 7:1 ratio is that, like the Perfect Webinar, it can be transposed onto all mediums. Emails? 7 value bombs and one ask (even if its 4 emails total). Video? well, you get the idea.
In chatbots, I found a wonderful exception to this. When you build a chatbot, it's a collection of modules (or parts) that are made up of 2-15 flows (topics with a start and a finish). You can create your promo sequences/modules in the chatbot, and surround it with any amount of non-promotional modules with no risk of overdoing the withdrawals.
Why? Because the lead, the bank, can treat the chatbot as a self-serve buffet of goodwill. It's a blank cheque, and it works because the non-promo flows will all, at some point, encourage/suggest/persuade that the lead take a look at the promo stuff, but does not force it (unless you're Grant Cardone in 2019 and your team gets abusive with sequences).
The lead can choose to take ALL the value the chatbot offers and never click on the promo buttons, or can grab the first freebie and think "ok cool, what's this CTA about?" and choose to allow the chatbot to proceed. The tradeoff to such a self-serve ecosystem is that it allows the user to advance at his/hers own pace, which often results in the 7:1 ration happen within a single afternoon at no extra work to you and without annoying the lead.
Which is best? All of them, because they do different things and serve different people. Some people hated my chatbot but opened every email I ever sent them, whereas others loved the chatbot and exhausted every conversation before taking action. MOST people however, used the chatbot to move quickly when something engaged their curiosity, and leaned on my emails for occasional updates.