HOW TO IMPRESS YOUR BOSS

1. Care about people

I put this one first because it’s the foundation for

everything that comes after. Caring about others is an absolute necessity.
If you don’t care about them, and you’re only in this for yourself, people
will know. They can spot insincerity a mile away. If you’re labeled as
insincere, it won’t matter how much you do for everyone; they’ll always be
assuming you have an ulterior motive, and you’re just trying to work an
angle to come out on top. The only way any of this will work in the long
run is if you are truly interested in seeing other people succeed, and you do
your best to help them along the way.

If this doesn’t sound like your cup of tea, you may as well stop reading this
article right now – it won’t help you. Do us both a favor and go play
some Flash games online (my kids highly recommend Dino Run). But
if you do care about people, or at least want to make an honest effort to do
so, read on.
2. Always be honest

This is the second foundational element. The most

valuable resource you have with others is their trust, and it’s much easier
to lose than it is to gain. This is a lesson we’ve all learned from childhood
on up, yet we continue to tell lies or half-truths to make ourselves look
better in certain situations. Don’t do this. Ever.

If you have a habit of lying about big things, then obviously you have some
work to do, and you should get on it. But what I’m mostly talking about
here are the small things. For instance, if you mess up with someone, and
fail to meet a commitment you promised them, don’t try to make excuses
to cover it up. Apologize and ask what you can do to make it right – you’ll
be respected for it. Doing anything else will show people that you’re willing
to say whatever’s necessary to avoid the consequences of your actions. And
if they see you doing that with small things, it’s a solid bet that they
assume you do it with big things as well.

You can sometimes break the rules, but you can never bend the truth.
Losing trust is the worst thing that can happen, because it makes all the
other things you do nearly worthless in the eyes of others.
3. Speak your mind

If you’re always honest, you shouldn’t have much of a

problem speaking your mind when the situation warrants. This doesn’t
mean you have to talk all the time (I’m one of the quieter guys in most of
my meetings) . . . you have to determine when it’s important to talk, and
when it’s okay to stay quiet. But if you’re always honest, people will know
that when you do speak, you mean what you say.

Here’s an example. The first time I wrote a big email to the CEO of my
large company, it was to criticize him for something he said at an all-
company meeting. Since this was my first major interaction with him, I
was taking a big risk – and I’m not gonna lie, some of the things I’m
talking about doing will sometimes put you at risk. But when you don’t put
yourself out there and take a chance, you don’t get a shot at the big payoff.

Because my CEO is a great guy, he thanked me for my feedback and took it

under consideration. The next time I emailed him, it was in high praise of
something he did at an all-company meeting. What do you think his first
thought was when he saw another email from me with the subject
“Feedback?” Probably nothing good. But when he opened it and saw my
sincere thanks and appreciation for his recent actions, I’ll bet he realized
something: that this guy is not a suckup, and will say what he thinks, no
matter what the situation. And that is a valuable relationship to have with
your leaders. Going forward, as long as you continue to remain honest and
speak your mind, you’ll be building up trust with each interaction.
 One caveat to this point: you must be aware of the situation when speaking
your mind. No one likes to be called out in front of their peers, so if you
have criticism to give, do it in private, and be sensitive to the feelings of
the person you’re talking to, especially if it’s a high-level leader who may
not be used to receiving it.

4. Be respectful – with an edge

You always need to show the proper respect for

anyone, be it your boss, your spouse, your friend, or even a stranger. That’s
a given. But when you start giving your boss too much deference, and turn
him into a demi-god, it doesn’t help anything. He’s just a person who
happens to be in a higher position than you. And if he’s the kind of guy
who enjoys it when people suck up to him, he’s probably not the kind of
guy you need on your side anyway. I’d rather have the rest of the office
backing me up in that situation.

As a boss, I can tell you that I hate it when people suck up to me. It
automatically drops you a few notches on my “trustworthy” list. Why
aren’t you trustworthy? Because I can see that you’re willing to
compromise your true thoughts and feelings to be viewed in a more
positive light. And that tells me that you’re in this for yourself, and I can’t
trust you to be someone who will help me or another team member with
something that’s important to us.
 When you’re dealing with people who are in a higher position than you,
remember that it’s not always what you say, but the intent behind it. I get
away with saying a lot of things to senior leaders that other people can’t
say. This is because I’ve built up a reputation as someone who always
works hard to help others succeed. They know that I’m here to help
support them, and if I have something that I really disagree with them
about, I’ll be sure to let them know, and not go behind their backs. They
trust me, so I can be free to joke around a little more, and have a bit more
of an edge than most people, as long as I stay aware of the current
environment and don’t overstep any bounds of respect.

5. Ask for help

If you don’t know what you’re doing in a certain

situation, don’t pretend like you do. Admit your ignorance and ask for help
from someone who knows what they’re doing. I see two benefits to doing
this. First, it helps you learn something new. Second, and more
importantly, it makes someone else feel important. Their interaction with
you, where they were able to help you out and feel good about their own
knowledge and generosity at the same time, may well be the highlight of
their day. Give them that gift, and pay attention to the friendliness and
respect you’ll get in return. This is especially true if you’re in a leadership
position. Never be too proud to learn from anyone else in the company. In
fact, I’ll go so far as to say that there’s always at least one thing you can
learn from everyone you meet – so don’t take anyone for granted.
6. Plan to wing it

This sounds a bit contradictory, I know. We usually

want to control our circumstances as well as we can to make sure
everything works out in the best possible way for us. But the fact of the
matter is that we’re rarely as in control as we think we are, and
occasionally we’re thrown into complete chaos. In fact, we’re quite often
judged more on how we handle the curveballs thrown at us, so it’s good to
have a plan in place for dealing with them.

I like to prepare for these situations by practicing once in a while. Take a

controlled situation that you’re going into, and resist the urge to plan every
detail. Decide that in this instance, you’re going to wing it, because the
worst that can happen is not that bad. Voluntarily practice thinking on
your feet, so the next time you’re forced to do so, you don’t freak out.
People are always watching you, and if you can handle unexpected and
difficult situations gracefully and effectively, your perceived (and actual)
value will soar.
7. Work hard to help others

Everyone knows that there is incredible value in hard

work. But when you work hard to help other people, that value is
multiplied. If you make it one of your goals to help others achieve their
goals, you’ll go through life being recognized as a great worker, but more
importantly, you’ll also be seen as someone who cares about others. This
will do wonders for your own attitude and personal satisfaction, but in
addition to that, it will cause people to think of you first when they want to
work with someone. And having everyone in the company wanting to work
with you is a great card to have in your deck. [This comes from one of my
favorite posts.]
8. Ask questions and look stuff up

Don’t be that clueless guy in the meeting who just

nods like he knows what’s going on. If I’m talking and I see that going on,
I’m always tempted to directly challenge that person on their knowledge of
the topic. Of course I don’t, because I’m not in the business of making
 people look foolish, but for the love of Pete, if you don’t understand
something, ask a clarifying question.

I do this all the time. Sometimes I’m ignorant and need to be educated,
and sometimes I catch the presenter being unclear or flat-out wrong.
Either way, your boss will respect you for it. If you don’t have the
confidence to ask the question during the meeting, follow up with the
person individually, or look it up on your own. Do not walk away without
understanding the topic or being prepared to learn about it. I was home-
schooled through eighth grade, and I think the line my mom used the most
was “Look it up.” What kind of teacher is that? Well, she’s the kind of
teacher who helped me understand that we have all the knowledge we can
handle readily available to us, and usually the only thing stopping us
from learning is laziness.

One final thought: when you do look stuff up and learn something, share it
with the group. Don’t hoard information. Ever.

9. Do what you’re not supposed to do

You heard me right. Stop following all the rules.

Rules exist mainly so that people don’t have to think about the right thing
to do all the time – they can just follow the rules and pretty much be okay.
And that’s fine for most people, but if you really want to stand out, take the
time to figure out which rules can be bent, and which can be broken. But
don’t just go around breaking rules and expecting good things to happen –
be very deliberate in when, how and why you break a rule, and make sure
it’s something that benefits other people, not yourself.

If you break the rules for yourself, even if it’s for a perfectly legitimate
reason, you’re viewed as a selfish, pompous, I’m-better-than-you-type
person. But if you break the rules to help out other people, even for
something small, you’re viewed as an altruistic, charitable person who
goes to great lengths to help others.

Here’s an example of what I mean: I was at an all-department meeting at

work, and we were served lunch. The buffet line was up near the
presenters, and everyone had had their lunch and dessert already – the
presenters were in full swing. I was at one of the tables in the back. I had a
little bit of a hankering for another brownie, but the rule says that I
shouldn’t go up near where they’re speaking to go grab one – it could be
viewed as rude. So I didn’t go. Now don’t get me wrong, I’ve built enough
of a reputation that if I wanted to go up, people wouldn’t think twice about
it – that’s just me being me – not one to observe proper etiquette all the
time. But in this case I had decided to stay put. A young intern at my table,
however, mentioned that she would love another brownie, but was afraid
to go up and get one. I waited a moment, then walked up there, grabbed a
brownie (with the tongs), and put it on a plate. I walked back to the table,
sat in my place, and wordlessly slid the brownie plate over to her. I used
up a tiny bit of my political capital by walking up near the presenters, but
think about how much of a positive reputation I gained from the seven
other coworkers at my table, along with anyone else who saw what I did.
This is the kind of rule-breaking I’m talking about.

Know what you’re doing and why you’re doing it at all times, even if it
may look strange to people who don’t know the whole story. You gain two
things by approaching life this way. 1) You’re looked at in a positive light
by those whom you help (and those who see you help others). 2) If you
consistently break social norms in small, relatively inconsequential ways,
 people just note that you’re “a little odd”, and ascribe anything off-color
you do to that mental model. If you’re okay with people thinking this way
about you, it frees you up to make a lot of unintentional faux pas in the
future and come away unscathed. It also frees you up to try a variety of
social experiments, but that’s a different article.

10. Give people more than they expect

Seriously, this is way easier than it sounds. I do this

all the time in very small ways, but they eventually add up. For instance, if
someone asks me to provide them with some data, I’ll email it over to
them, but I’ll also throw in a little note with a few related links that may
also help them with their project. I’m pretty good at finding things online,
and it doesn’t take me very long. For my extra two minutes of work, I may
save them 30 minutes of additional searching. And even if it doesn’t help
them this time, they’ll remember that I gave them more than they asked
for, and that I’m a really helpful guy. If you can consistently produce small,
positive interactions with people, pretty soon their image of you will begin
to include all the things you want to be known for. [More on this topic
here.]
11. Get organized

How are you going to do all these great things for

everybody if you’re not organized? There are a thousand different ways to
do it, and I can’t help you choose the right one. I have a habit I picked up
when I used to do some fiction writing – I carry a miniature notepad and
pen around in my pocket at all times. This helps me capture any idea,
question or task that may be important. Once you start doing it, it’s really
cool to know that you’re not missing anything anymore. Of course, you still
need a good system to help you process everything. For that I recommend
David Allen’s “Getting Things Done.” I intentionally didn’t link to the book
on Amazon, because I want to make sure you know that I make no money
by promoting this book. It’s just a method that has worked well for me,
and it may be a good starting point for you. Staying organized makes doing
all this extra work a lot easier.
12. Whatever you do, do it with a touch of “you”

I cannot stress this enough: Know who you are, and

BE THAT PERSON. If you’re funny, don’t try to be too serious. If you’re
 serious, don’t try to be too funny. Look for ways that you can work in the
things you’re good at, and stay under the radar when you’d be forced to
play your weakest hand. Don’t try to fix all your weaknesses – that’s a
losing game. Just mitigate any ill effects from those, and then capitalize on
your strengths. The point is to be genuine and memorable in a positive
way, and you can best accomplish that by doing what you’re good at.

For me, one of the personal touches I put on email correspondence is by

communicating in funny pictures, even to people I don’t know. I have a
huge repository of images saved by the name of the idea they represent,
and it’s become second nature to pop these into emails as I go. This
doesn’t take me any extra time, but it makes my day more fun, and I’ve
gotten numerous responses about how the recipient broke out into
laughter during a meeting, or otherwise appreciated the gesture. Little
things like that are what make you unique . . . don’t be afraid to use them
to become memorable as well.

Warning: Neglecting to impress the boss could be hazardous to your career! The good
news is that most bosses are astute in recognizing "that special something" that makes
employees stand out from the crowd. If you are viewed in this manner, you’ll progress
further--faster. Have you mastered the following "boss impressers?"

Let your word be your bond

It’s common for high achievers to struggle with a tendency to over commit. Their desire to
accomplish great things can cloud their ability to set reasonable limits. Unfortunately, good
intentions can backfire. Many superstars’ reputations have burned out like meteors because
they started dropping important balls.

Employees who consistently deliver on their promises impress bosses. Reminding employees
of unfulfilled commitments causes resentment from bosses--not respect. One manager
described his most impressive employee with the following statement, "When I give her an
assignment, I immediately mark it off on my list as done!" Could your boss make a similar
remark about you?

Protect them from surprises

"Everyone loves surprises"--except bosses! Sometimes employees hesitate to share bad news
with their boss, fearing it will be a poor reflection on them. In reality, if they hear it from
another source, you can pretty much be guaranteed of a bad reaction. If this happens, your
boss will conclude one of two things: 1) you try to hide things--and cannot be trusted, or 2)
you lack the good judgment of knowing what to bring to his or her attention.

Your boss will be impressed if you are honest and upfront with even bad news. Don’t forget
to advise him or her of your plans to rectify the problem also.

Never assume

When given an assignment, don’t make assumptions. For instance, if asked to prepare a
report, "when you get a chance," it would be wise to request a specific target date. If you are
unclear on what your boss expects from you--find out! Knowing the right questions to ask--
and when to ask them--is a sign of a true professional. And it can save you from many
unnecessary communication breakdowns.

Bosses appreciate employees with enough concern (and common sense) to get the facts so
that expectations are met. It shows you have good foresight and planning skills--two
impressive qualities.

Clean up your messes

Excuse makers are a dime a dozen, and they rarely move ahead. Admitting weaknesses takes
courage and self-awareness--two admirable qualities. If you don’t know, say so. If you make
a mistake, admit it. Then, take the important step of cleaning it up! Employees who refuse to
accept accountability are very frustrating to bosses. People generally won’t kick you when
you are down. We all make mistakes, and it’s refreshing to hear someone own up to theirs. If
you stubbornly deny responsibility for your mistakes, however, you can count on a rude
awakening--and a displeased boss.

Look the part

Professional dress is a sensitive topic. Nobody likes to think they dress inappropriately, but in
reality this shortcoming certainly does holds people back.

"Dress like the position you wish to attain" is a good rule of thumb. Sure, it seems superficial.
You may protest that people should not "judge a book by its cover." In principle, you may be
right. But human nature and principal do not always match. If you lack the judgment to dress
professionally, don’t be surprised when people assume you have deficiencies in other areas
also.

To impress the boss, dress like one yourself!

Take a risk!

Those satisfied with the status quo always outnumber bold risk takers. Why? Much of the
difference has to do with motivation. Ask anyone in a responsible position whether their
success was achieved by being cautious and timid. It’s highly unlikely! Chances are they
became visible and respected because they displayed courage and enthusiasm.

Think of it this way . . .bosses are ambitious people who recognize and admire that same
quality in others. Ambition requires ample confidence to stick your neck out occasionally and
take a risk. For example, you can volunteer for a challenging project, or recommend
workflows that are more efficient than the "way we’ve always done it around here."

Bosses cherish talented employees who demonstrate their desire for excellence in a variety of
ways. . .and on a regular basis. Putting these six tactics into practice is certain to leave you
with an impressed--and happy---boss.