In my outpatient psychology practice, I hear so many questions
about being assertive. What is it? How does it work? When is it
needed or effective? Can you use it at work? What about with
intimates? In school? With anyone?
Assertiveness is about sharing some aspect of our experience
with others. My favorite metaphor is playing cards. We lay down
our cards, face up for our opponent to see. We are sharing what is
in our hand. By way of analogy, we communicate what is on our minds,
or express our feelings, presumably using words. Ideally, we do
so in a matter-of-fact manner, without much fanfare or drama.
It is a transaction and we execute it with increasing adroitness,
proportional to our training and practice.
Assertiveness is a skill that should transcend environments and
relationships. If we are truly assertive, it should not matter so
much where we are and with whom we communicate. In theory, it should
work anywhere with anyone.
In actual practice, assertiveness is not quite so clean and easy.
Assertiveness works best with intimates even though there is the most
potential fallout from being honest. In theory, intimate
communication works least well with acquaintances even though there is
less likelihood of a negative response from people we do not know well
or with whom we are involved with less.
This is because in true assertiveness, the effectiveness
(and consequences) increases the more we share our feelings.
This puts us at risk with intimates because now "they know" how we
really feel. But it also puts us at risk with acquaintances because
we might breach a boundary; that is, say too much that is personal to
someone who is not really a friend.
For the acquaintances, assertiveness comes out more cognitively;
that is, intellectually, devoid of too many feelings. In these
types of communications, assertiveness pretty much sticks to the
issues to be discussed, not our visceral reactions. With a boss,
for example, we can ask for a raise or complain about the workload,
but the communication will be transactional; that is, centered on a
narrow task, expectation or work experience. If the boss is our
friend, which can happen, assertiveness is easier from the feelings
point of view, but then becomes more complicated because now this
person in power also is privy to our feelings, not just our work
performance.
The antidote to these dilemmas is to first ask ourselves what
is the level of interpersonal depth of the relationship in question.
In the above example, we might ask, "How close am I to the boss,
really?" If the answer is questionable, assertiveness will tend
to be transactional. Stick to the more intellectual communication.
Stay focused on the situation or event and describe it in literal
terms, leaving feelings to be inferred by the listener.
More personal relationships have less censoring of personal
information and feelings, which can more easily be described using
actual feeling words. Friends also require less "pre-structuring"
(see below) of the communication. We just "go for it" because
with friends we have tacit permission.
However, with friends, many of us worry that because they are
friends, they will now keep this deeper communication longer.
If the communication happens to be less than ideal
(negative thoughts and feelings), it may haunt us in more personal
ways, and maybe for a long time.
A simple way to overcome these worries is to create some
communication before the communication (pre-structuring).
Try simply asking a person if he or she wants the polite or the
honest response to some issue. Or, phrase it another way.
"Do you want the superficial or deep answer?" This nets a
surprisingly good response from a lot of people. It allows the
other person to cue us about the desired depth of communication.
That way, we are less likely to offend someone by being too
personal, nor to insult anyone if we keep things on the surface.

Dr. Griggs