Ask Anna – How do I manage up to a boss who won’t give guidance?

Dear Anna,

How do I manage up to a boss who won’t give guidance and wants me to figure everything out on my own?

PQ

Dear PQ,

First of all, I want to tell you that I have been in this exact position and it is HARD. When I started out in professional services, the culture I worked in was very “entrepreneurial” and had all the benefits and challenges of an entrepreneurial culture. What I mean is that there was a lot of leeway, not a lot of guidance, a lot of praise for doing something right, and a lot of flack for doing something wrong. It’s a lot of pressure.

Figuring out how to manage up to your boss, in a way that works for her, will help alleviate some of this pressure. To figure out how to best manage up to your boss, ask yourself the following questions:

How does she best receive information?

Email, text, pass by in the hallway, phone/Zoom convo, scheduled meeting or drop by “unexpectedly.”

What time of the day is she usually at her best?

Does she have a lot of energy at the beginning of the day but feel overwhelmed by the end OR is she ready to turn her attention to the team at the end of the day but not at the beginning?

What’s most important to her? What are her big goals for herself, this project, etc.?

Is her next goal to get promoted? How does the project you are working with her on support that? Is having time with her family after work most important to her? How can you support that?

If she’s not going to give you guidance in the way you might like, what is the next best option?

For example, if you’d like for her to give you step by step instructions or tell you where to start and she doesn’t seem to be doing that, what’s your next best option? Maybe it’s asking if you can connect with someone else who really knows how she likes things done. Maybe it’s asking for an example of the deliverable she is asking you to create.

If you put yourself in her shoes, how might she be perceiving your interactions to date?

Remember that she is coming to each conversation and interaction with you from a different perspective. What story might she be telling about your interactions? Is that the way you want her to be perceiving the interactions? If not, how can you change your approach?

With the answers you have developed to those questions, how might you change your approach? Some options to consider are:

Get guidance based on observing her interactions with others. Does she seem to care a lot about details? Does she get excited when people are creative? Observation can provide a lot of guidance without ever having to ask her for it.

Create your idea of guidance and validate it with her or someone else. Can you make an educated guess at the guidance and put it in front of her to validate?

Consider whether it would be more helpful for you as a professional to figure it out on your own without her guidance. Like I mentioned for my case, this is the hardest option but it also grows you as a professional. If your expectation was that she would never provide guidance, what would you do differently? How would you figure it out on your own if you weren’t waiting for her?