Working With Difficult People: 5 Types & Strategies
1. Working With &
Leading Difficult People
Chaz Arnett
Juvenile Defender
Baltimore Juvenile Justice Center
Email: chaz.arnett@gmail.com
2. Why Is This Important?
• Difficult person may be your boss
• Need to develop a skill or learn a
technique that the difficult person has
mastered
• Being evaluated for team work done
with difficult person
• Can not avoid difficult person
• Needing to increase productivity of a
difficult employee you manage/
supervise
• Difficult person has access to networks
you need to tap into
• Untapped potential in difficult person
that could be useful
• Maintaining a low stress work
environment
3. Five Types Of Difficult People
• Ben The Bully
• Negative Natalie
• Lazy Larry
• Udonis the Underminer / Brutus The Backstabber
• Micromanaging Michelle
5. Bully Characteristics
• Prevents others from speaking at
meetings or events
• Publicly criticizes coworkers/team
members in demeaning and rude
ways
• Uses intimidation to either coerce
into or block others from work and
projects
• Extreme arrogance masking
insecurities (Know-it-alls)
• Hyper-competitive behaviors
• Feeds off of being in the control of
others
6. Dealing With Bullies?
• Bullies MUST be confronted in
constructive ways
• For challenging public attacks, use humor
to poke fun at the bully and cast their
mean spirited attempts as silly
• Address the bully privately to express your
concerns and fend off any signs of
weakness
• Never forfeit control by losing your
composure
• Lean on friends and church leaders for
advice on how to navigate
• In severe incidents raise issue with
management/administration (careful not
to be perceived as weak or a whiner)
• In less severe scenarios, or where the bully
is your subordinate, seek in-roads with
bully by learning more about him/her and
what drives them
8. Characteristics of Negative Natalie?
• Pessimistic about work projects and
their value
• Unhappy about current status/position
at work and in personal life
• Shoots down others’ hopefulness and
creativity, and saps other people’s
energy
• Self-defeatist nature leads to intended
and unintended assaults on leadership/
work progress and productivity
• Believes something fundamental, has
not been given or has been taken from
him/her at work
• Attempts to form disgruntled groups/
cliques
9. Neutralizing Negativity?
• Avoidance only works to a minimal,
and silence is acquiescence. To lead,
grow, addressing the “Debbie
Downer” may be necessary.
• Stepping back and not taking things
personally (separate the person from
the issue)
• Leverage direction and flow of
communications/conversations
• Shift from being reactive to the
negative person to being proactive
• Pick your battles wisely and save
energy
• Listen. Hear the negative person out,
but continually force them to reflect
on concrete solutions, instead of
simply venting.
11. Characteristics of Lazy Larry
• Avoids tough projects and heavy
work assignments
• Does not follow through on
scheduled assignments and
deadlines
• Never volunteers or assists other
coworkers or team members
• May be wrestling with a lack of
confidence in being able to take on
several tasks
• Does not care about the quality of
their work
• Deny ever making commitments
that they do not uphold
12. Motivating Lazy Larry?
• Provide unexpected “shout outs” to
the individual for the work they do
(affirmation)
• Focus on what assets are available to
the person and what can be done,
versus focus on what has not been
done
• Be more strategic assigning projects,
setting deadlines, and providing
feedback
• Refuse to be an enabler. Doing extra
work to cover for lazy coworker or
team member can quickly lead to
burnout
• Focus on your own work product and
be more aggressive in making sure
your boss/supervisor is aware of all
the work you are specifically doing if
on a team project
14. Characteristics of the Underminer
• Revels in office or workplace gossip
and/or drama, because any and all
information is seen as useful ammo
• Self-centered; will always look out
for themselves first over the team
• Will never assume accountability
for failures/inactions that make you
or the team look bad
• Will unabashedly assume credit for
other people’s ideas and work
• Refuses to assist others unless it is
perceived to benefit the underminer
• Exposes your missteps (or actions
characterized as missteps) to
management in attempts to make
themselves look better
15. Blocking the Backstabber
• Always cover your tracks and
protect yourself from sabotage
• Stay above the fray on office gossip
and drama, and never give too
much information for others to use
• Ensure that your office “confidant”
is truly reliable; or if you can/
should even have one
• The backstabber is never openly
undermining you. Be sure to
identify who may be working
against you to be better able to
neutralize that person
• Remove the Shield: seeking advice
and input from potential
underminers even when you do not
need it
17. Characteristics of the Micromanager
• Lacks confidence in team and
others
• Needs work done in ONE way and
ONE way only: THEIR way
• Incessant inspections on work
progress
• Re-write/re-do reports and projects
to their own specifications
• Stifles creativity and individuality
• Fails to get the most out of her
employees by preventing
development and growth
18. Managing Micromanagement
• Be more strategic in getting tasks,
assignments, and projects documented
in writing, with detail
• Seek out other avenues for additional
work from another manager or
supervisor
• Be proactive and develop professional
growth map/calendar to discuss with
manager
• Meeting manager in nonthreatening
(less intense environment); after work
events; see each other in a different
light
• Reflect and evaluate the worth/benefit
of experience versus the work
environment
