New Executive, Entrenched #2

 Hello - I'm working with a situation that's perplexed me some and I could use some advice.

I'm a new executive to a relatively young not-for-profit with a small five person staff. the organization was founded in 2010, and the first executive (my predecessor) was largely a fundraising person. My predecessor didn't really provide any sort of strategic vision or guidance to the organization - I like to say the organization just sort of burned fast and hot under that leadership, and all of the focus was put on what was immediately in front at any given time. 

So it should come as no surprise that the organization made little progress under that leadership - lots of opportunities were left on the table which is huge and awesome for me as a new leader.

The organization's #2 person had to become very autonomous. They worked with essentially no management oversight whatsoever, and basically just did what they thought was right at every juncture. The good news is that they're absolutely fantastic at what they do and everyone in the organization loves them - partly because they all know how inept the person above them used to be.

So, a few struggles:

1. I'm struggling somewhat to manage this person who "holds the keys" to a degree for me still. I keep a list of questions to ask them regularly, because they're the most readily available resource for learning about the organization both on a high level strategically and historically but also on things like where we keep the copy paper.

2. This person has gone without a manager almost her entire career here, and isn't used to oversight, which has been very challenging for me. Throughout my career I've dealt with people who "teach" you not to manage them - interpersonal backlash is the reward for oversight. This seems to be the biggest challenge along those lines I've faced. Their responses to my efforts at oversight have been subtle, but generally unappreciative. 

I've tried to focus on the fact that they are fantastic at their job, to over-the-top feedback them on all of the positive comments I've gotten on them, and also to just appreciate the fact that the department (operations) is something I don't really have to focus on. I also recognize that this is likely weird for them as well, and I want to be sensitive to that. I'm also down with the trinity and planning to implement as I can - I don't want to overwhelm with new/different.

I guess I'm looking for any advice from those who may have found themselves in this situation before. Appreciate it!