Dear Liz,

I recently started working with a new supervisor, and she’s hard to read. When I send her drafts of my writing projects (I work in online curriculum development), she returns them to me with lots of edits. I don’t mind the edits, but she hasn’t given me any qualitative feedback like “good job,” or “this should have been better.”

I’m working as hard as I can, but I’m constantly wondering whether I’m exceeding expectations, or if I’m at risk of being fired.

Should I just assume I’m doing well (and do my best to set aside my pangs of fear that I’m not) and hope for a positive 6-month review? Or what’s your advice?




Dear Reading-Between-The-Lines,

This is an important question and I’m so glad you wrote for advice (instead of suffering in silence until that 6-month review)!

You deserve to hear this first: it’s clear to me that you’re working hard to produce good work. And it is tough to walk into work every day not knowing where you stand with your manager.

That said, you are wasting your energy trying to read between the lines of the behavior of someone you barely know. (Even for someone you do know well, it’s still a waste of energy -- thanks to my husband for constantly reminding me of this).

The best way to figure out what someone is thinking is to ask.

So my friend, it's time for you to ask!

Before I show you how, I should also mention that this isn't an issue for you alone. I encourage all of my clients to have a “Kick Off Conversation” with any new manager.

Because you need clarity of your manager’s expectations to succeed in your role. And in just one 20-minute conversation you can get it.

What does a “Kick Off Conversation” look like?

Schedule a 20-minute meeting within the first month of working with any new boss (preferably in person, but an over-the-phone meeting works too).

If your manager asks about the purpose of the meeting, you can tell her “I’d like to ask you a few questions to make sure I’m doing everything I can to best support you in my role.” 

Then, choose a subset of the following questions based upon what you want you to learn:

  • “What would a successful first 6 months in my role look like? Are there any specific metrics or milestones I should be shooting to achieve?”

  • “What are your communication preferences? Do you prefer phone, email or in person? Do you have any preferences for how or when my work is submitted to you?”

  • “How often do you want status updates from me? Do you have any preference on how much detail you want in those updates or how they’re formatted?”

  • “How do you want me to respond if I’m ever feeling stuck? Should I reach out for your input proactively, or put together a draft for your review?”

  • “How often should we meet to check in on my performance? What do you prefer these meetings look like?”

  • “Who's the best employee you've ever had and what were their qualities that you most appreciated?”

  • “Do you have any initial feedback for me based upon our work together thus far? What should I know about your general preferences regarding giving or receiving feedback?”

Last, be ready for some of these questions to come back to you. You’ll want to be sure to ask for what you need to thrive in return.

Asking can feel scary.

Many of my clients resist scheduling these conversations, with objections like, “But she’s so busy... What if I look stupid, or she thinks I’m some millennial hungry for constant feedback? If she wanted to have the conversation, she would have initiated it!”

If this sounds like you, keep in mind you’re going to:

  1. Ask once for 20 minutes of your manager’s time;

  2. Demonstrate your professionalism and value by asking specific, simple questions about how you can make her life easier; and

  3. Learn exactly what she expects of you, setting yourself up to deliver what she wants, when and how she wants it (and saving you both hours of time in the process).

If you’re still not convinced, that’s okay. It’s normal to search for reasons not to have this conversation (and of course you’d prefer that your manager initiates it).

At the core of our resistance lies what we’re really afraid of: fear of confrontation, and ultimately fear of rejection.

And when you’re staring down these fears, it’s almost easier to choose suffering in silence for 6 months! Why should you be the one to take the risk?

Because it’s a risk worth taking.

Only with open communication can we learn who the people in our lives are, what makes them tick, and what they want and need from us.

Only with open communication can they learn the same about us, and partner with us in creating mutually beneficial and meaningful relationships.

It’s possible your boss doesn’t want to have this conversation. But more likely, she was simply too busy to think of it. Or perhaps she thinks you’re doing a great job and doesn’t realize you’re interested in coaching. Or perhaps she’s never had this conversation modeled for her, even though it would benefit her greatly. 

No matter what her reason is, don’t let that stop you from getting the answers you need to thrive in your job, and from building a relationship with your boss that will help you both be stronger, more connected, and more successful together

I’d love to hear your thoughts - do you think Kick Off Conversations are worth having? Or what strategies have you used to learn what your manager wants?