I found this interesting and decided to overthink it.

Before proceeding, pause to think about whether this seems right to you and why.

The thesis here is something like:

There is a right amount of confident to be.
Encouragement proportionally raises confidence.
(Implicit) Encouragement does not do other important things.
→People often need encouragement.
People tend to be less confident than they seem.
Your estimate of their confidence will be based on how confident they seem.
→You will tend to overestimate their confidence level.
→You will tend to underestimate how much they need their confidence raised.
Your estimate of how much encouragement raises confidence is unbiased.
→You should give people more confidence than you expect them to need.

Also implicit is that ‘more’ is about the right level of adjustment here.

Once again: Does this seem right? Which steps seem right to you?

1: There is a right amount of confident to be → Mostly True.

Confidence is strange. It is often a partially-self-fulfilling prophecy. It has various different effects. When founding a startup it can only be accurate at 0% but you will be better off with it higher, when looking to date similar dynamics often apply. Still, we can have one-dimensional ethics, and declare that of all the options there is almost always a best one. And under uncertainty, there is almost always a best one to push someone else towards.

2: Encouragement proportionally raises confidence → True in expectation.

In general, encouraging someone will tend to raise their confidence. Some methods of encouragement do this more than others. Saying ‘that will work for sure’ will tend to focus its effects more on increasing confidence and in turn making action and hopefully success more likely. Saying ‘it’s good to attempt hard things, I’ll be proud of you for trying, good luck’ or ‘you will almost certainly fail or get turned down but the odds are so good you need to do it anyway’ might have different effects.

3: (Implicit) Encouragement does not do other important things → False

Encouragement provides information, changes probability of various actions, changes social context and who can get or expect credit and blame from who, will effect credibility and so on. Encouragement is in part a claim that has a truth value, sharing knowledge and your guess on their chances of success and the wisdom and expected value of their actions. Often encouragement is not about confidence.

4: →People often need encouragement → Mostly True.

This does seem true, but I often note that ‘need is a strong word.’ People often would benefit from encouragement. Often this is because they would benefit from more confidence, sometimes it is for other reasons. To say they ‘need’ encouragement is language I prefer not to use, but I mostly agree with the jist.

5: People tend to be less confident than they seem → True by default.

A lot of naïve estimators are biased. This is one of those examples, mostly because a lot of people are continuously and intentionally faking confidence. There are exceptions and I know many of them, but mostly yes if you take someone’s confidence level ‘at face value’ you will guess too high. But guess what? If your estimates are known to be biased you should be adjusting them. It would shock me if Paul Graham hasn’t been making this adjustment automatically for a long time. He outright tells people, as advice, to present to people like him as having lots of confidence. I don’t make as large an adjustment because I interact with different people in different ways, but in many contexts I of course believe that how confident people present themselves and say they are are blatant lies. They, in turn, know everybody knows this, and this only increases their need to bluster to cancel out my downward adjustments.

6: Your estimate of their confidence will be based on how confident they seem → True but incomplete.

I mean, yes, obviously, but it will also be based on how confident they could reasonably be in the situation, and how much incentive they have to present as overconfident or how much their circumstances would have trained them to be overconfident in this kind of situation and your guess on their view on distorting your perceptions of their confidence levels and so on. It all counts.

7: →You will tend to underestimate their confidence level → Mu. That depends.

Again the obvious thing to do if this is true is adjust your estimate, rather than adjust what you do elsewhere to compensate. Doesn’t seem that hard. It’s not an especially difficult adjustment.

8: →You will tend to overestimate how much they need their confidence raised → Mu because it depends on #7, also other factors.

If your estimates of confidence levels become unbiased the problem would go away, so this centrally depends on whether you have fixed that. If you haven’t, there is still the question of whether issues of confidence levels dominate. If your estimate of other impacts is unbiased and mostly continuous, it should be fine.

9: Your estimate of how much encouragement raises confidence is unbiased. → Could go either way but my guess is more often false

My hunch is that most people underestimate the impact of their words of encouragement on confidence in many situations. Hearing such things often has a large impact, especially from someone you respect in the contextually important ways. It’s highly plausible this cancels out the original effect. In other situations, the lack of confidence runs deep, and the opposite effect can easily occur – ‘why aren’t you suddenly confident asking people out after I encouraged you?’ – but it does seem like we have a good sense that moving those dials is difficult.

10: →You should give people more confidence than you expect them to need. → More often true and good advice than false and bad advice, but varies.

If nothing else this needs an ‘otherwise’ since it is an adjustment of a potentially biased estimate to remove the bias. Properly implementing it should also change your expectations and all that. In practice, doing more encouragement on the margin seems to be good on most margins where you would indeed prefer the thing you are encouraging. My guess to the primary mechanism there is more like ‘it would be mildly socially awkward and require doing/saying something/more rather than nothing/less which no one likes to do, so people do it less than they should.’ The ‘people are not as confident as they seem’ thing seems secondary to me, and if that was the only consideration I’d consider this mostly false. I also aim to focus more on the truth value of encouragement than the confidence effect, for both some good reasons and some personal preference reasons.

Recently I did offer people encouragement, in particular to apply for SFF funding. How much of this was because I was estimating that (1) charities lacked confidence in their chances of success and (2) they lacked confidence in their ability to ‘do it right’ as opposed to having a lack of the required knowledge? Somewhat, but also because my gut told me they were also (3) unaware of the opportunity, (4) lacked the required knowledge which I attempted to provide, and (5) treated the cost of applying as higher than it is and treated failure as far more painful than it would be. When such folks ask me more questions directly, as several have, I am careful only to offer careful and directed encouragement where it makes sense.

My overall guess is that there is too much and overly intense encouragement that is not genuine, as in not done because one feels the actions in question would be worthwhile. There is too little and insufficiently intense encouragement that is genuine, with the need to further raise confidence levels a substantial portion of that but not dominating other reasons especially trivial inconvenience, lack of motivation and mild social awkwardness.