The document outlines strategies for managing various types of difficult bosses, including those who do not listen, communicate poorly, or display unprofessional behavior. It provides specific techniques for addressing each boss type, such as asking open-ended questions, documenting communications, and anticipating needs. The overall goal is to help employees navigate challenging workplace dynamics to maintain productivity and career growth.

1. Prepared by : Wong Yew Yip
20 Types of Tricky Bosses
Source : How to manage your boss - Ros Jay

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 Ask to repeat back what you’ve just
said, with tact
 Ask open questions (no yes or no
answer) so he/she can’t simply
mumble ‘Mmm’ at you absently
 Get to the point quickly, briefly and
succinctly
 Get your comments, briefings or
requests in writing or email
The Boss who never listens
You know your Boss is not listening to you, but you can’t start
screaming, ‘Listen to me, dammit!’ without jeopardizing your position
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What can you do?

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 Often, all you need to do is ask -
“Can you tell me what it’s for, and
when it’s needed by?”
 Make a point of asking open rather
than closed questions
 Ask question and then shut up until
he/she answers - eventually the
silence will become so
uncomfortable you will get a reply
The Boss who never communicates
Without the necessary information you can’t do your job properly
and the results can be devastating and demoralising
2
What can you do?

4. 4
 Do it for yourself - you have to do
your boss’s job in order to be able
to do your own
 Anticipate the problem and do what
needs doing in plenty of time
 When it comes to decisions or
resources, write a brief report or
proposal for your boss
The Boss who never does anything
You’ll never turn this boss into a powerhouse of frantic activity or
decide anything, so there’s no point wasting your efforts trying to
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What can you do?

5. What can you do?
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 Don’t get involved in an
argument with your boss about
his/her prejudice
 Be armed with examples that
contradict your boss’s prejudice -
show by your example
 Don’t inadvertently reinforce
your boss’s prejudiced views
The Boss who is prejudiced
When your Boss judges you wrongly for something you have no
control over, it is extremely frustrating and can damage your career
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6. 6
 Point out to your boss when the
task is impossible and find a
workable solution
 This type of boss expects you
never to make mistakes, so explain
that you feel under undue pressure
to be superhuman, and you need
to be allowed to learn from your
mistakes sometimes
The Boss who is a perfectionist
Boss wants not only perfection, but also in an unreasonable length
of time, or at an unreasonable cost, forgetting vital factors
5
What can you do?

7. 7
 You’re going to have to do some of
the work yourself
 Remind your boss in advance
about meetings and appointments
 Chase up for information/report the
boss promised before deadline
 Make your boss be aware of the
potentially damaging
consequences of his/her
disorganization
The Boss who is unorganized
Boss won’t be able to find information you need, forget to turn up at
meetings, promise something and then disappears
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What can you do?

8. 8
 Get as much of your own
contribution to the organization
down in writing as you can
 Take ideas to the boss as
proposals instead of verbally
 Email/send memo to boss outlining
concerns and recommendations for
remedying problems
 Get your achievements down in
black and white
The Boss who is no good at the job
Boss incompetency adversely affect department performance and
you can be viewed as incompetent as well
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What can you do?

9. 9
 Get achievements down in writing
for when you need them -
appraisals, promotion interviews
 Encourage your boss to put
instructions to you in writing, or
email to your boss for confirmation
 If your boss blames you for
mistakes in public, don’t try to pass
the blame back - accept the blame
using “we” a lot instead of “I”
The Boss who passes the buck (on to you)
Boss blames others for own mistakes, in private and public. It is
particularly annoying and can damage your career.
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What can you do?

10. 10
 Ask for more frequent performance
reviews and feedback sessions
after you complete projects well
 Ask for rewards or recognition in
advance
 Find ways to motivate yourself
 Work towards targets of your own
or promise yourself a reward for
certain achievements
The Boss who is a poor motivator
Boss shows little or no interest in your work whatever you do, or
wields plenty of sticks but no carrots, recognition or rewards
9
What can you do?

11. 11
 Don’t respond to a tantrum with
emotion - remain cool and rational,
and stick to facts
 Don’t give in to your boss when
he/she is having a tantrum
 Any time you decide you’ve had
enough, you’re entitled to leave,
find an excuse
 If you can, enlist the support of
your colleagues
The Boss who throws tantrums
This kind of behavior is abusive, and there’s no reason why you
have to stand for it
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What can you do?

12. 12
 Spell out for this boss exactly what
you need from him/her to do the
job and explain why
 Put this list of requirements down
in writing so the boss cannot claim
ignorance
 If things still wrong and your boss
attempts to let you take the blame,
you’re in a position to demonstrate
that it wasn’t your fault
The Boss who won’t back you up
Gives you little or no support, and then steps back when things go
wrong, leaving the full spotlight to fall on you
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What can you do?

13. 13
 Volunteer for extra responsibilities
as often as you can
 Ask for training and new
responsibilities
 Point out to your boss the
advantages, for example, covering
for other staff
The Boss who won’t let you develop
You want new challenges/fresh responsibilities. But your boss is
happy for you to stay as you are, doing a good job.
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What can you do?

14. 14
 Get your boss to be specific, ask
which aspects of the project won’t
work, and why
 Play on your boss’s fear of failure,
point out why rejecting your idea
would be riskier than accepting it
 In moderation, negative comments
are helpful - don’t dismiss all
negativity out of hand
The Boss who is negative
Always looks on pessimistic side of things, tells you your ideas won’t
work and outlook is always bleak - it’s demoralizing & demotivating
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What can you do?

15. 15
 Almost every control freak has one
or two chosen people who he/she
can trust - you just have to become
one of the trusted few
 Give a progress report even before
the boss asks for it
 Perform tasks exactly as the boss
stipulates
 Copy your boss’s style
The Boss who is a control freak
Checks up on you constantly, tells you exactly how to do each task,
delegates little or nothing. You feel stifled and unable to develop.
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What can you do?

16. What can you do?
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 Never tell the boss he/she is wrong
- the best way to get them to see it
is by asking innocent questions:
“Can you explain . . .”
 This type of boss is actually wrong
quite often - when this happens,
resist temptation to say, ‘I told you
so’, and instead help your boss to
save face
 Make sure you get things right as
often as is humanly possible
The Boss who is always right
Boss won’t listen to anyone else’s point of view, thinks he/she is
always right. Once the mind is made, the subject is closed. Period.
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17. 17
 If your boss is stalling, there is
some kind of conflict - ask what it is
 If your boss is simply indecisive
and puts off making decisions, try
acting as an unofficial adviser and
help to make the decision
 Don’t pressure this kind of boss too
hard - he/she may do anything just
to get you off his/her back
The Boss who stalls
When you need a decision or to put your case to senior
management, boss somehow wriggles, stalls, or just plain disappear
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What can you do?

18. 18
 Keep records of your ideas and
suggestions and notes of relevant
meetings with your boss
 Get your ideas down as a formal
proposal, with your name on the
cover page, and the date
 Let other people know about your
ideas, either verbally or by copying
to them anything you can justify,
including your proposal
The Boss who takes credit for your ideas
This is infuriating and damaging to your career. If your good ideas
aren’t recognised as your own, how can you be rewarded for them?
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What can you do?

19. 19
 Tell your boss you are not
comfortable with the situation and
something has to be done about it
 If your boss refuses to stop and
you decide to take action, make
sure you can prove your
allegations of dishonesty
 Should your boss try to involve you
in the dishonesty, refuse without
moralising
The Boss who is dishonest
Telling lies to get out of trouble, or falsifying reports to make the
figures or performances look better
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What can you do?

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 If it’s not too late already, don’t start
working long hours. It’s a lot easier
to say no in the first place
 Don’t allow your boss to intimidate
you into working unreasonably long
hours - you have the right to refuse
 Coming up with a reason for cutting
down your hours, will be a big help
 Prove that your performance is still
good despite cutting down hours
The Boss who believes in workaholism
If your boss wants to work 18 hours a day, it’s really not your
problem. But if you’re expected to join in, it can be a big problem.
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What can you do?

21. 21
 Try feedback with your boss who
may be unaware of the problems
he/she is causing
 Anticipate what you’re likely to
need so that when he/she is
around, you can sort out all the
things you’re going to need
 Put all your requests as briefly as
you can, so as not to waste what
precious time you have with boss
The Boss who is simply never there
The boss is needed to make decisions, authorises things and solve
issues - hard to achieve when your boss is never around
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What can you do?

22. Thank You
yewyip@gmail.com