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I've read in other posts (such as this one) about the right way to teach the Dhamma.

But is there a way to know about the "when", i.e. when to reach out someone else to teach the Dhamma?

In specific, I'd like to know if one should teach only when asked for it, or if one should make assumptions about the other's needs or degree of knowledge when trying to help him/her (regardless if that person asked for that helped or not).

If you could provide information about suttas where this is talked about, I'd really appreaciate it. I'd even be grateful if personal experiences are given.

Thanks for your time and patience!

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When somebody wants to know and is receptive. For the most part if you consider the way the Buddha taught, you notice he’s usually only directly addressing the sangha without being asked. Otherwise people usually come to the Buddha with questions. I don’t recall any texts were the Buddha goes out and engages people who are not part of the sangha without being asked. The only exception I can think of is when he initially taught to the five ascetics at Deer Park. After that everyone comes to him. I’m sure there are exceptions.

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  • Hi! If that person does not ask you directly, how do you knoe if he/she is receptive? Thanks! Kind regards!
    – Brian Díaz Flores
    Commented May 9, 2019 at 0:44
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    @BrianDíazFlores If you know something about there interests, maybe you see them reading certain books, talking about certain topics, or engaging with others in certain ways, and by certain I mean subjects that would fall under wise matters in regards to Buddhist thought (something that may vary from Buddhist to Buddhist). Personally, I first learned about Buddhism in a middle school world history class, what I learned at the time made me receptive to the offering of some Buddhist books latter on in my life.
    – vajra78
    Commented May 9, 2019 at 6:00
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Part Three: The 16 Dealing with Teaching Dhamma
57. I will not teach Dhamma to a person with an umbrella in his hand who is not ill: a training to be observed.

  1. I will not teach Dhamma to a person with a staff in his hand who is not ill: a training to be observed.

  2. I will not teach Dhamma to a person with a knife in his hand who is not ill: a training to be observed.

  3. I will not teach Dhamma to a person with a weapon in his hand who is not ill: a training to be observed.

  4. [62.] I will not teach Dhamma to a person wearing non-leather [leather] footwear who is not ill: a training to be observed.

  5. I will not teach Dhamma to a person in a vehicle who is not ill: a training to be observed.

  6. I will not teach Dhamma to a person lying down who is not ill: a training to be observed.

  7. I will not teach Dhamma to a person who sits clasping his knees and who is not ill: a training to be observed.

  8. I will not teach Dhamma to a person wearing headgear who is not ill: a training to be observed.

  9. I will not teach Dhamma to a person whose head is covered (with a robe or scarf) and who is not ill: a training to be observed.

  10. Sitting on the ground, I will not teach Dhamma to a person sitting on a seat who is not ill: a training to be observed.

  11. Sitting on a low seat, I will not teach Dhamma to a person sitting on a high seat who is not ill: a training to be observed.

  12. Standing, I will not teach Dhamma to a person sitting who is not ill: a training to be observed.

  13. Walking behind, I will not teach Dhamma to a person walking ahead who is not ill: a training to be observed.

  14. Walking beside a path, I will not teach Dhamma to a person walking on the path who is not ill: a training to be observed.

https://www.accesstoinsight.org/tipitaka/vin/sv/bhikkhu-pati.html

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    What is the purpose of these particular conditions?
    – user11699
    Commented May 4, 2019 at 7:43
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    Someone shows that they are fit to receive the teachings by displaying humility (which is through a display of respect for the teacher). This is a common sense condition within all teaching situations, workshops
    – user15039
    Commented May 5, 2019 at 2:17
  • @KilayaCiriello Thanks, that clarifies a lot
    – user11699
    Commented May 6, 2019 at 11:34
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Well then, Lord, does not the Blessed One teach Dhamma in full[1] to some, but not so fully to others?"

"I will reply to this question, headman, with another. Answer as seems proper to you. What do you think? Suppose a peasant farmer has three fields, one excellent, one middling, and one poor, sandy, salty, with bad soil. Tell me: when the farmer wants to sow his seed, which field would he sow first: the excellent one, the middling one or the poor one that is sandy, salty and with bad soil?"

"Lord, the farmer who wanted to sow his seed would sow the excellent field first. Having done that, he would sow the middling field next, and the one that was poor, sandy, salty, with bad soil he might or might not sow. Why? Well it might do for cattle-food."

"Well, headman, that excellent field is like my monks and nuns. To them I teach the Dhamma which is lovely in its beginning, lovely in its middle and lovely in its ending, in spirit and in letter,[2] I display to them the holy life, perfectly fulfilled and purified. Why? Because these people adhere to me as their island, their shelter, their resort, their refuge.

"The middling field is like my male and female lay-followers. To these too I teach the Dhamma which is lovely in its beginning, lovely in its middle and lovely in its ending, in spirit and in letter, I display to them the holy life, perfectly fulfilled and purified. Why? Because these people adhere to me as their island, their shelter, their resort, their refuge.

"The poor field that is sandy, salty and with bad soil is like my wandering recluses and Brahmans of other sects.[3] To them I also teach the Dhamma which is lovely in its beginning, lovely in its middle and lovely in its ending, in spirit and in letter, I display to them the holy life, perfectly fulfilled and purified. Why? Because if they only understand a single phrase, it would long be for their profit."

https://www.accesstoinsight.org/tipitaka/sn/sn42/sn42.007.wlsh.html

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    Hi Sarath! Thanks for your answer. If I'm not misunderstanding this sutta, isn't this referring about 'how' to teach the Dhamma instead of 'when' to teach it? Kind regards!
    – Brian Díaz Flores
    Commented May 4, 2019 at 2:11
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    There are many restrictions in Vinaya when not to teach Dhamma. For instance, you should not teach Dhamma to a person who drives a vehicle.
    – SarathW
    Commented May 4, 2019 at 2:23
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See grave faults in the Bodhisattva-vows, since the questioner has lesser to no respect toward the Buddha-Sasana:

(11) Teaching voidness to those whose minds are untrained

The primary objects of this downfall are persons with the bodhichitta motivation who are not yet ready to understand voidness. Such persons would become confused or frightened by this teaching and consequently abandon the bodhisattva path for the path of personal liberation. This can happen as a result of thinking that if all phenomena are devoid of inherent, findable existence, then no one exists, so why bother working to benefit anyone else? This action also includes teaching voidness to anyone who would misunderstand it and therefore forsake the Dharma completely, for example by thinking that Buddhism teaches that nothing exists and is therefore sheer nonsense. Without extrasensory perception, it is difficult to know whether others' minds are sufficiently trained so that they will not misconstrue the teachings on the voidness of all phenomena. Therefore, it is important to lead others to these teachings through explanations of graduated levels of complexity, and periodically to check their understanding.

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  • If one is not sure that a listener can grasp the idea of "voidness" they can be reminded of the temporary nature of all things and that clinging to unstable things exposes one to suffering.
    – user15039
    Commented May 5, 2019 at 2:20

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