What do you do if your boss needs more support and guidance?

Assessing needs is the starting point. I have a lot of experience in this process as a treasury systems selection consultant. Assessing needs begins with documentation of the "as is" environment" and then the proposed "to be" environment, with a strategy and migration plan for how to get there. I like to take very detailed notes in meetings, of what my boss and his/her peers have to say. And then I like to keep those notes as a permanent record. They become the platform for a future success story.

Usually, managers are relatively sensitive to admitting that they need support from their subordinates. In these cases, you should identify the problem your manager is facing. Don't tell them that you realize they are having difficulty, just tell them that you have a new idea and don't know if it is feasible, ask them for their opinion. From there you can help them indirectly.

I enjoy solving challenges. Generally speaking, I'm brought in as a consultant. I make my work available to others, including my copious notes from meetings. Everyone can then use those resources. I enjoy teamwork including opportunities to help my colleagues solve their challenges. I believe that enjoying the experience of being able to help others is a key ingredient to successful teamwork. I tend to not sit on fences (ala humpty dumpty).

I recently established a relationship with a local police officer over a breakdown in the relationship between two other members of the community where I currently live. It involved one guy offering to repair multiple vehicles belonging to another guy, and then not getting the work done. Both of these two men have various mental disabilities and mental health challenges. They were unable to communicate. At one stage, one of them could have gone to prison (he has young children). I met both these men through a mutual friend. I am very systematic. I documented the disagreement. Then broke the issues down into a series of mini projects. And then one-by-one worked through the issues. I only involved the police officer if things got stuck.

It took me a while to realize that approach to your boss should not be that different from approaching any other high impact stakeholder. Once you overcome this hurdle, your life will become perhaps easier. Like with an external or internal client, you need to become a problem solver, an ally. You cannot rely on your ideas being the best by default and instantly being recognized as such. You need to spend time and effort to prove they are going to help. You need to 'sell' them. Part of the process is the trust gained through track record you have in the relationship.