Here are some of the most useful simple methods I’ve adopted for improving my connection with others (though I still have room for improvement):

1) When you like someone, greet them warmly, demonstrating with your face and body language that you like them.

2) Try your best to channel “interested attention” in conversations – where you give the other person your total focus while paying very close attention to what they are saying (and how they are saying it) and starting with the premise that they are saying something worth listening to.

3) When you disagree with a friend about something important, ask open-ended questions until you deeply understand their perspective, and if you still disagree, express that disagreement gently and respectfully while pointing out the parts you agree about before exploring what you disagree about.

4) If a close friend does something that bothers you one time and it is out of character for them, just let it go. If that friend has a pattern of behaviors that bothers you, wait until you are not actively feeling bothered, and then tell them how it makes you feel when they do that behavior (describing the behavior in objective, fact-based rather than subjective terms) and request that they try to avoid it going forward (in order to help strengthen your relationship).

5) Try to balance the amount of time you spend speaking vs. the amount of time the other person spends speaking so that it doesn’t go outside of the 40%-60% range. Note that this is an average across conversations, there are specific situations where it makes sense to do more or less of the talking (e.g., if one of you has a big story to tell).

6) When you think a nice thought about someone (and you don’t have any reason to think they wouldn’t want to hear it), tell them the nice thought. For instance, if you admire them in some way, or if they did something you really appreciate, or if you’re really looking forward to seeing them, let them know! As the saying goes, thinking something nice about someone and not telling them is like wrapping a nice present but then never giving it.

7) Don’t complain about how old you are unless you’re sure you’re the oldest person in earshot by a significant margin.

This piece was first written on March 15, 2024, and first appeared on my website on March 27, 2024.

Lately, I’ve been trying to accept a bit more awkwardness (rather than reflexively avoiding it) in cases where I think doing so can produce value.

Here are four areas where I’m leaning more into awkwardness:

1. When asked for feedback on a project (and I think it will fail), I’m usually tempted to focus on what I like about it. 

I’ve now become more likely to explain what challenges I expect it to face (while suggesting routes to improvement).

I think that, usually, more value is produced by trying to help them succeed at their goals than by trying to help them feel good about their current plans. Ideally, though, this feedback is given in a way that is encouraging and not demoralizing.

2. When someone annoys or frustrates me (e.g., makes a request in a manner that bothers me), the easy thing is to ignore it. 

I’ve become more likely to gently tell the person that it bothered me and explain why – while trying to avoid making them feel attacked.

This gives others the opportunity to learn and improve, and also, I think, tends to strengthen your best relationships (by making them more open and honest, and by preventing you from feeling worse about your friends due to behaviors they were doing that they didn’t even realize were bothering you)

3. When I think someone is making a false claim, it reduces tension by just letting it go. 

Instead of letting it go, I’ve become more likely to tell them that I don’t agree with their point and explain why.

This gives us the best chance of arriving at more accurate beliefs together.

4. When there is something that I value, but it requires making a somewhat awkward request, the path of least resistance is to give up on it. 

I’ve become more likely to make the request while doing what I can to make it very easy and non-awkward for the other person to decline.

Often we can set up a situation so as to at least minimize the awkwardness for the other person (e.g., by giving them a simple way out of the request and making it clear you won’t be offended if they decline). By not making such requests at all, we end up missing out on opportunities that others would, in fact, be happy to provide for us.

I’m certainly not perfect at this. I still avoid awkwardness at times when more value is produced by pushing through it. But I’m getting better.

While awkwardness is certainly not a good thing, if you are too motivated to avoid it, then – much like with other forms of anxiety – you and others may miss out on a lot of value.

Of course, some people need the opposite advice – they put others into awkward situations too often or lack awareness of the awkwardness they create. And I think you should try to reduce awkwardness whenever there is not a good reason for it.

But if you (like me) tend to avoid awkwardness, it may be better to strategically lean into awkwardness in cases where more value is lost by avoiding it.

This piece was first written on September 25, 2022, and first appeared on this site on September 30, 2022.