For a long time I've known that I have something of a knack for seeing other people's points of view. I've occasionally been accused of being a good teacher, or good at explaining things; every so often I manage to explain to two people how they're at cross purposes when neither of them have been able to work it out; I'm frequently unwilling to condemn people for doing apparently bad things because I can see why it seemed reasonable to them (though this isn't universal!). I wouldn't call myself world-class at it by any means – I certainly have my share of failures; but I think it would be fair to say I'm better than average at intuitively understanding (some) other people's viewpoints.

I've recently noticed that this can actually cause problems in communication. The thing that caused me to notice this was someone mailing the PuTTY team the other day, asking if we'd be willing to cover our web pages in links to his site in return for quite a lot of money. Now I was fairly sure that I was extremely unwilling to do this; but every time I tried to compose a reply to him, I found it was very difficult to say no to him. The more I tried to write a response, the more my words came out as if he was making a very reasonable offer which I was turning down out of perversity. Yet this is by no means how I actually feel.

It's taken me a few days to pin down just why I was having trouble with this fairly simple piece of communication, and I think the answer is this: when I start writing a message to a particular person, I automatically begin to shift part of my brain towards that person's viewpoint, or at least what I guess their viewpoint to be.

I think this is precisely the habit which makes me (sometimes) good at explaining and teaching: if I correctly guess my audience's state of mind, I can explain things in a way they can immediately grasp and understand, rather than them having to somehow reach towards my state of mind before they can understand my explanation. Of course sometimes I guess wrong, and it doesn't work; but I think I get a lot of mileage from the fact that it's an absolutely unthinking and automatic reflex for me to at least try.

Yet this same habit, I think, was precisely what was causing me trouble saying no to my prospective advertiser. As I tried to write a response to him, my mind shifted towards the viewpoint of someone who doesn't see anything inherently irritating in adverts on web pages, and who has no concept of whether someone deserves a high Google ranking or not, but who sees the proposition solely as something which would benefit both me and him. And the more I shifted towards this mindset for ease of communication, the more I found it harder and harder to articulate my essential objections to his proposition without coming across as simply perverse.

After a while I decided it was worthless arguing with him anyway, because in my experience if you reply personally to people like that they tend to see it as an invitation to try harder to persuade you, which (given my above difficulties) wasn't somewhere I wanted to be even if I thought I wasn't in danger of actually succumbing. So I stopped trying to frame a reply to him, and instead started to write a FAQ entry for the benefit of any future people with similar ideas, and then I suddenly found it very easy to say what I felt.

It's interesting that something I do precisely to make my communication effective can sometimes work precisely against effective communication. I suppose I'd better watch out for that in future.