I have had lots of problems when making decisions and deciding the work that I should be delegating. Summarising the techniques that can help me get better at these.
Decision generally has few alternatives & choosing between these alternatives are done using listing down pros and cons. Limitation of the pros and cons list is that we are merely transcribing our existing understanding of the decision at hand and not seeing it with fresh eyes.
Generate a lot of other options for any course of action being considered. Think of all the alternatives(even the ones that seem bad choices) and list them down. Then think of three different futures for each option: One story talks about where things get better from the decisions, on that makes matters worse and one that makes things weird.
Do a premortem. Tell yourself a decision that you took, and that decision caused a disaster, now forcing myself to think about the decision that turned out to be disastrous helps me look at the blind spots and the false sense of confidence.
It is not easy to think of a lot of alternatives, But it can be increased by consulting or talking with diverse groups of people, get a different perspective from many angles.
In general, it is tough to decide what work needs to be delegated. Farnam Street had a great article on that. The author separated the type of decisions into four possibilities:
The Decision matrix
Delegate both types of inconsequential decisions as they are perfect training ground to develop judgment.
Spend most of your time on important and irreversible decisions.
Reversible and consequential decisions: This can be delegated as well, people can run experiments, and the results of these experiments can be used as an indication if we are going on the right path.