Ten Things You Should Be Saying to Your Boss

One of the questions that my team members and potential employees have asked me a lot over the last few years is "what are you looking for in an ideal employee?" We just finished a performance review cycle here where I worked with a few members of my team on their development plans for the next year. I've also been spending some time identifying and interviewing potential new team members and holding regular mentoring meetings with the members of my team. This is all on top of leading the annual performance review process for more than 600 people while I was still with Booz Allen. Over the course of all those interviews and development discussions, I found that I've repeated a lot of things.

Here are ten of those things that I've said repeatedly over the last few years that I think any employee should be regularly saying to their boss. 

1. "How am I doing? How did I do?" Ask for feedback early and often. It shows that you want to improve and that you want to know how to do things better. After every presentation you give, report you complete, article you write, etc. make sure you ask your manager if he/she has any feedback for you. And don't let them get away with just telling you that "you did a good job." Ask them specifically what you could have done better. Seek the negative AND the positive feedback.
2. "Don't worry about it – I got it." One of the things that all managers love is to be able to cross something completely off of their to-do list because they know that someone they trust is taking care of everything – from beginning to end. From doing the actual work to keeping the right people informed, the ability to take something entirely off your manager's plate and do it well is something that will be much appreciated. It will also give you some great experience in showing him/her that you've got what it takes to move up to the next level as well. 
3. "I just read/watched/heard…and it got me thinking that…" Learn how to look at everything you read/watch/listen to from a work/client perspective. I want people who are constantly on the lookout for newer, better, more efficient ways to do things and who can apply them to their current work. You should be bringing new ideas to your boss at least as often as he/she is bringing them to you.
4. "You know how we've been doing X? Why do we do it that way?" Question the status quo. Don't just accept things because "that's the way they are." If you're curious about some process or rule or regulation, ask for the background on it. You'll be surprised to discover how many things we do for no other reason than that's the way it's always been done and no one ever bothered to ask.
5. "I don't think that's the best way to do that. How about we do it this way instead?" Please, don't be a yes-man/woman. Disagree with me. Don't just assume that what I say goes. Sometimes, I have no idea and am just throwing ideas out there and want some honest feedback on them. When I was first given a team, the first person I approached was a good friend of mine whom I knew would be candid with me and tell me when I was wrong. I knew that she'd tell me about an awful idea long before it made its way to the client.
6. "Here's what I'd recommend and why." If I've asked you to work on something, don't just send me your research. I want to know your thoughts on it too. You're the one closest to the research. Give me your recommendation and your rationale for it. It shows me that you can think critically and that you can back up your assertions.
7. "Here's what I learned and how I'll do it better next time." Learn how to be your own worst critic. One of the best things you can do is become self-aware. Know where you're strong, know where you're weak, and know where you can improve.
8. "You gotta see/read/listen to this – I know you'll love this." It doesn't always have to be about work. Don't be afraid to send your boss the latest meme if you think he/she will enjoy it. I like to know my team's interests outside of work, and I want them to want to get to know mine as well.
9. "Do you know who I can talk with to understand this better?" If you're struggling with something, I will NOT think of less of you if you ask how you can get smarter on the topic. I'll be impressed that you were self-aware enough to know what you don't know and confident enough to ask about it. I may not know the answer either, but I'll be sure to help put you in touch with someone who will.
10. "What can I do to help? Be proactive. Don't wait for other people to task you with something. Ask if you can help with something. Or better yet, refer to numbers 3 and 4 above.  

Now don't get the wrong idea here – while you may have thought this post was targeted toward more junior employees, these are all things that I try to regularly talk with my boss about as well. These aren't just for entry level or mid-level employees – at no point should you feel that you're too old or too high on the org chart to ask for feedback or to challenge the status quo. If you're a manager now, start asking your employees to think about these things. Likewise, look internally and ask yourself if you've been been doing the same with your boss.