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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.

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Love it!

Tied to #2 I like – boom I got it. and then a circle around – that got done & X happened

Tied to #3 I like – I went to this event on X (related to field) and had an idea from Y by meeting Z there

Deb Green

These are great ways to show your boss and your co-workers that you are thinking about the team and making the group really successful. That’s what I intend on doing.

And if you’re a boss, ask your team for feedback too. Don’t just aim question #1 uphill to your boss. Ask your employees and your colleagues too. Do your own 360 degree feedback. WTG Steve! 🙂

Michael Stevens

Great post! One of the best I have seen on GovLoop in regards to easy, common sense things you can do to help your career NOW.

Andrew Krzmarzick

Very nice, my friend. Definitely like #10 – willingness to pitch in and move something forward once you knock out some other tasks.

Muhammad Ali Raza Hanjra

Very concise and clear thoughts on making oneself’s presence felt postively in an organization. Great!

Jayeson Vance

This is superb advice and is also excellent in risk management for safety. Please refer if you like to Operational Leadership courses such as those taught in the National Park Service.

Cat Robinson

Thanks for the insightful post. I start work tomorrow (!) as the Graphic Design Fellow at GovLoop and I know this information will serve me well.

Wayne Melton

Agree it was a well thought out post. I would just add something to the effect that you completed your current tasks and improved on your job assignment. I found the worst thing I hated to hear from my employees was how they would do this a different way or something else better. Sometimes it is just important to do your job right. Get it done and make it know it is done and done well. Your boss will love your for it.

When you think up changes the boss actually has to make a decision he/she did not really want to make. You might be right but there may be other things involved such as policies or other people who make your ideas impossible to implement. I always hated the many “suggestions” on how to change things. Usually I just wanted them done so we could focus the team on the really big issues.

Of course I might be wrong.

Wayne Melton

Steve Radick

@Wayne – I think there’s definitely an element of that too, so long as it’s in balance with the others. I can tell you that in my experience though, I’ve had no problem with finding people whom I can count on to do their job. The rarer thing is finding the people who will do the ten things I’ve outlined above – the critical thinking, the initiative, the going above and beyond – that’s the type of person I want working for me. The danger in focusing too much on pushing people to just get the job done the way I say is that you end up with a team who can’t think on their own and are there just to do what you say.

Chris Knox


This is a great article. As a manager, I see some sound advice for helping to challenge and motivate my team to greater productivity without insulting or demeaning them. I also see it as a great resource for sharing internally with other managers who struggle with communicating higher expectations across an organization that is slow or reluctant to change.


Jeffrey Levy

One of the best posts I’ve ever read about management. That might surprise some, because it’s about managing your boss, not the other way around. Should be required reading in every developmental training.

Dannielle Blumenthal

Generally I think this post is the right intention (as Jeff pointed out, managing up). However – taking the perspective of the boss – I have a somewhat different reaction than most of the commenters. See below.

  1. “How am I doing? How did I do?” Agree
  2. “Don’t worry about it – I got it.” OK, but then actually take care of it
  3. “I just read/watched/heard…and it got me thinking that…” You have already lost my attention as I don’t really care what you are thinking.
  4. “You know how we’ve been doing X? Why do we do it that way?” This sounds obnoxious.
  5. “I don’t think that’s the best way to do that. How about we do it this way instead?” Also sounds obnoxious.
  6. “Here’s what I’d recommend and why.” Agree
  7. “Here’s what I learned and how I’ll do it better next time.” Agree but keep this short, you are not in school anymore
  8. “You gotta see/read/listen to this – I know you’ll love this.” Don’t waste their time, be careful with this
  9. “Do you know who I can talk with to understand this better?” The boss will assume you have done your research first before asking this question and that’s why you need them to clarify
  10. “What can I do to help? Have a suggestion in mind.
Steve Radick

@Danielle – If you’re speaking as a project manager who’s focused on deadlines, project plans, and Gantt charts, I can see how some of these may come across as “obnoxious.” But, if you’re trying to be a leader, not just a manager, I think you want, no, need, people to do all of these things. Otherwise, you end up with a team so focused on accomplishing laundry lists of tasks instead of growing and innovating and taking on more leadership themselves.

Dannielle Blumenthal

Glad for the chance to clarify, since the post was overall useful and in print the feedback I provided read harshly. Sorry about that.

It’s true, leaders should engage and employees take initiative. This is so whether one is managing a project or running an enterprise. (Most projects fail because everyone is too busy to do a reality check.)

My concern is really with the “how.” One has to be careful with the actual words, the context, and the packaging of the idea/input. A colleague once told me this (well it was the same thing my husband has been saying for twenty years, since I tend to overwhelm with questions and ideas, but of course I listened better to her.)

For me it’s not about the “should” but rather about “what works.” I like this quote a lot: “When a person is down in the world, an ounce of help is better than a pound of preaching.” (Edward G. Bulwer-Lytton). Much of the time at work I think people are somewhat clueless about how to help themselves. Posts like yours, in places like GovLoop, make a difference. It’s all good.

Steve Radick

@Danielle – I definitely appreciate your insight, but I think we can agree to disagree here then because I think this advice applies to all employees, especially those at a mid-career level. If you’re looking to move from do-er to leader, if you’re looking to take that next step into management, I think you have to be doing these things with your current boss. I’m a VP and still do these things with my SVP, maybe even more so than when I was a junior employee.

Dannielle Blumenthal

In a creative field you never know where the next good idea will come from, so the business model facilitates the upward flow of ideas. However does that translate to all environments? Probably not. For example you don’t want police officers questioning procedure on the way to respond to a burglary, or surgeons thinking outside the box when they’ve got you on the operating table.

The question here is – to what extent does this advice apply to gov employees? Certainly at the new and/or junior level, yes. Intermediate, yes. We actually need to promote questioning everything, because as we all know the bureaucracy is so entrenched that obviously silly things don’t get changed.

However, to be taken seriously as you go higher you have to get past the “of course” factor. As in “of course this makes no sense.” The point of all the leadership training is to help you appreciate and work with complex situations and stakeholders sensitively. So as you go up the chain you are more and more expected to arrive prepared. Not just with a technical solution You have to know the sensitivities around suggestions before making them. Also you have to know that there is a time and place, and when resources are scarce and work volume is high, that brainstorm might have to wait until a quiet Friday afternoon instead of crazy Monday.

Mostly I speak from experience, not academic study, like anyone, and frankly from making mistakes. One of those has been to offer ideas without a full understanding of the culture/history/politics that led to the seemingly inefficient way of doing things. Another has been that I just didn’t realize how very busy leaders and managers are – dealing with people as well as doing the work. There is no right answer, but it is a very important topic and it’s good to discuss it from diverse points of view.

On the other hand there is no better way to show value than to be engaged in the work and try to help save time and money.

Jana Opperman

I still get email comments for this blog even though it says I am not following this. Can someone please help me get this to stop? When will I learn to not make a comment? there is something wrong in the programming, I have contacted several folks at Govloop with this problem for a few years but I keep thinking it will work this time…All my settings are set to not receive emails except for direct messages to me. I have reset and rebooted and all the practical fixes to no avail.

Steve Radick

@Danielle – I think you make some really excellent points here and think it ultimately boils down to being sensitive to timing and culture. No, you definitely don’t want surgeons questioning years-old practices on the operating table just like you don’t want that analyst questioning your methods the night before a huge deadline. But you also don’t want to create a culture where you’re expected to just say “yes sir” to everything your boss says either. I think most bosses want to have really engaged employees that they have to pull back every once in a while than “yes men” employees who just do everything you ask without question. To your point, every boss, every situation, every organization is different – in some cases, saying these things “regularly” may be every week, but in others, it may be every quarter. Understanding that nuance is key too.

Maggie York

My boss was given my unit to supervise (staff training), but her primary focus is supervising our financial units (A/P, Cashiers, Budget). So several of the above suggestions don’t work.

Any thoughts on what to say to her are greatly appreciated. As it is I’ve tried to educate her on what we do, how we do it, and why.

Steve Radick

@Maggie – it’s obviously tough to be too specific here as every office environment has their unique dynamics, but one approach that I’ve used in situations like this is to turn it around on them. Show them how what your work does impacts her. Show her how the work that your unit does make her job easier. Instead of educating her on what you do, educate her on how you can help make her life easier. I remember in one case I was moved under a new manager who knew nothing about me or what I did and didn’t seem to care…until I started getting some internal notoriety for the work I was doing. Then he seemed much more interested in learning about what I was doing and getting more involved because as one of his direct reports, the work that I was doing was reflecting well on him. From that point on, he was much much more interested!