The Engaging DM

A guide for Dungeon Master’s on how to

create a more engaging environment for their
players.

by Jason Kramer

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Preface
No Dungeon Master wants to spend a great deal of
”You are not entering this world in the usual time preparing an epic adventure and have it fail.
manner, for you are setting forth to be a Dun- So how does a Dungeon Master succeed at this
geon Master. Certainly there are stout fighters, task? The answer is in getting the players engaged
mighty magic-users, wily thieves, and coura- in the adventure, campaign or world setting you
geous clerics who will make their mark in the have created or are running.
magical lands of D&D adventure. You however,
are above even the greatest of these, for as DM
you are to become the Shaper of the Cosmos. It A newer Dungeon Master may ask “How do I do
is you who will give form and content to the all this?” whereas a veteran Dungeon Master will ask
the universe. You will breathe life into the still- “What’s the best way to do this?”. The purpose of
ness, giving meaning and purpose to all the ac- this document is to answer both of those questions.
tions which are to follow.”
—Gary Gygax.

Above is a wonderful quote from Gary Gygax who is

one of the co-creators of Dungeons & Dragons. If
imagination were likened to an instrument then one
line in particular from the above quote should strike
every note and every chord that instrument: “ You
however, are above even the greatest of these,
for as DM you are to become the Shaper of the
Cosmos”.

As “Shaper of the Cosmos” a Dungeon Master may

create a masterpiece of adventures, campaigns
and worlds. And yet while having the greatest of
ideas if the Dungeon Master is unable to get the
players at the table immersed in that world then
they have effectively failed as a Dungeon Master.

A good portion of this document will be on asking

questions. That is to say - how to ask the right
questions! The right questions will “force” a player
to engage in the game. There is a difference be-
tween asking a player “Did you open the door?”
and “How are you opening the door?”.

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Questions, Questions. Dude?!
An engaging question begins with an engaging
Questions are one way to get players at your table story or background that leads up to it. A great tool
engaged in your game. So let us examine questions for Dungeon Master’s to use to get players en-
and questioning! gaged in location descriptions of adventure areas
are references that the players can relate to - like
Many questions start off with the predictable five movies!
“W’s”: Who, What, When, Where and Why. These
are common words that precede a question or help An example for a Dungeon Master using this tool in
in forming a question but they are by no means the their game is a situation where a player or Non
only way to ask a question. Do you know what I Playing Character (NPC) has disappeared around
mean? the corner of dungeon just ahead of the players.

Take several minutes to think about your recent To illustrate and set up an engaging illustration the
games and write down on paper what questions Dungeon Master could ask the players “Did anyone
you asked the players, the players asked you and here see the movie Fast Times from Ridgemont
what the players were asking each other. High?” “Remember Sean Penn who played the
character Spicoli? OK. So the NPC goes around the
Look at the questions you wrote down. How many corner of the darkened dungeon ahead of you and
of them were there? Do the questions interest you disappears around a corner …..and your character
or create any interest in you? Why not? Are you is like “Duuuuude???”
asking other people questions that bore you or in-
spire you?! For anyone who has seen the movie right now their
imagination is filled with a blonde haired character
Practically any word can be used to start a ques- going “Duuuude???” This is a much more engaging
tion. In fact in some cases it’s all about intonation way to describe the scene to the players as now
of the voice. To demonstrate: Say the word “Dude” something that they are familiar with is occupying
out loud. Now say the “Dude” out loud but in an an- their imagination.
gry way like your partner accidentally jammed you
in the ribs trying to get your attention. Notice the Now that the scene is set up it must be followed by
difference in your voice? a question that further engages the players. There
are two types of questions: Open ended and
Now imagine a surfer dude in a horror movie where Closed. They are so named in the way the question
their surf bro has disappeared around dark corner is answered. A closed question is answered with a
of a creepy house they are in. Imagine the surfer yes or no and an open ended question is answered
dude asking where his surfer bro is using only the by an explanation of some kind (Basically an an-
word “Dude”. Try saying the word “Dude” like it’s a swer that is more than a simple yes or no one word
question. Did you notice how the sound of your explanation).
voice went up towards the end of the word “Dude”?
Did it take you longer to say the word “Dude” as a At this point the Dungeon Master has the players
question than it did when you said it earlier force- attention and the question they ask once they have
fully? the players attention is crucial. To keep the players
engaged after a great opening description the Dun-
This surfer anecdote is a great example of many geon Master needs to follow it with an open ended
different ideas a Dungeon Master can use to get question.
people engaged in their game.
Perhaps the most used open ended question in
Dungeons and Dragons by Dungeon Master’s is
“What do you do now” or “What would you like to
do”. As these questions require more than a “yes”
or “no” to answer them they are great open ended
questions to ask.

If the Dungeon Master opens with a great reference

that describes the scene or situation for the charac-
ters and then proceeds to ask a closed ended ques-
tion they have just killed all the momentum they
started in getting the players engaged and will
have to start all over again.

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Take a moment to write down some popular one- Why are they better? Because the question allowed
liners from movies that your group would be able to the player to give a response that is more emo-
relate to. Then find a way when your planning out tional in nature. If the player is having emotions
your adventures to put them into a scenario or situ- about what is happening in the game then they
ation as a way help illustrate it. are engaged and this is what every Dungeon Mas-
ter is looking to have happen in their games!

Emotions are one way of telling a player is en-

gaged. There are some other tell tale signs that
players are engaged in your game. Players leaning
in towards the table is often a nonverbal sign. Play-
ers beginning to smile is another nonverbal cue.
When players begin to talk to each other and begin
to ask the Dungeon Master questions are tell tale
signs they are engaged in the game.

Don’t take people not appearing engaged as a bad

sign as sometimes people might be engaged and
don’t show it. Or other times people might be dis-
tracted or having other issues. Don’t take these
things personal as they have nothing to do with
you and everything to do with that person.

A good practice for Dungeon Master’s that have

distracted people at the table is to give them some
time and see if that resolves the issue or state to
everyone “Lets take a break for 10 minutes so ev-
eryone can go to the bathroom, stretch their legs
or take care of whatever”. During the break the
Dungeon Master should ask the distracted player if
everything is ok or can they care of texting on their
phone etc… as it is distracting other players.

What did you roll?

Take a moment as Dungeon Master and think of the
games of you have run. In those games what ques-
tion(s) do you ask your players most? Are you even
asking questions or are you giving command ques-
tions like “What did you role?”

What did you role? This a closed question in that it

is answered with a simple one word responses like
“Crit” “Fail” “18” “Dirty 20” etc… A Dungeon Mas-
ter that watches the players roll, makes eye con-
tact with them and says “How did you do?” will
have a much different response from players. In-
stead of giving a simple one word response now
the players are going to begin to elaborate on their
answers a little bit more. Even if there is answer is
only a few words “Not good” or “O yeah I’m killin’
it!”. These responses are far better than “12” “7”
“18”.

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What would you like to do?
“What would you like to do now ?” is a great open “Did you like College” is very different from “What
ended question. Dungeons and Dragons at its core was College like for you?”. The first question is a
is a verbal based communication game therefore closed question and the second question is an open
the key to getting players engaged in the game will ended question. Do you see the difference in re-
be in the quality of verbal communication between sponses each one gives? Again this is a closed
the Dungeon Master and the players. question and is very different from “Could you ex-
plain the differences between the two questions
Understanding how to ask open ended questions is above?” which is open ended.
an essential tool for the Dungeon Master. Open
ended questions require more than one word to an- Understanding how to create open ended questions
swer. The more words a player begins to use to an- is an important skill for a Dungeon Master. In some
swer your questions the better. situations creating an open ended question is as
simple as tacking on “And why?” at the end of
There are exceptions when players are to vocal and question that would otherwise be a closed ques-
the usual cause of this is the desire for attention. tion. “Your character shut the door?….Why?” Now
Pay attention for these types of players. Handle the player is engaged with having to explain their
them in a polite manner without cutting them off. actions (Which takes more than one word).
One way to let them know they are prattling on to
much is to make a joke about “to much backstory” The best practice for learning how to create and
or that the NPC isn’t writing a book or that the vil- ask open ended questions is to write a question on
lage scribe or historian went home for the evening. paper and practice reforming ways of asking the
question to make the question both an open ended
Back to open ended questions and how to ask and closed question.
them. This task may appear easy but it can be very
difficult for some people who are in the habit of Let’s give this a try shall we? It starts with a simple
constantly asking closed ended questions. One way question…..any question. Did you watch TV today?
to find out if you are this type of person is to take First we look at the question and answer it. Yes.
out a piece of paper and write questions that you Now we identify it as open or closed: closed.
would ask a person if you went out on a date with
them. After your done writing a few questions look Now how do we make it an open ended question?
at the sheet and ask yourself if the majority of the One way is to simply add a second question “Why”
questions can be answered with yes or no or do to the end of the first question. This gets boring
they require a longer answer. fast and starts to remind people of an inquisitive
and increasingly annoying four year old.

So what is another way to figure out how to create

an open ended question for a closed question?
More often than not by identifying the object of the
question and then asking a question based on this
object will lead us to an open ended question.

Yeah, turns out paying attention in English class in

school might have been a good idea. For those who
have forgotten the parts of speech a simple way to
remember it is to imagine a stage. The actor on the
stage (which is doing the action) is the Subject of
the sentence. The Action the Actor is doing is the
Verb and that which is being acted upon or receiv-
ing the action is the Object. “Did you(Subject) watch
(Verb) TV (Object) today?” The object is TV.

By questioning the Object we are on the path to

finding the way to turn a closed question into an
open one. Try asking questions about the TV until
we find a question that can’t be answered with just
a one word answer. What kind of TV is it? Was it an
HDTV? What show was on? Do you follow any
shows? What channels interest you?

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You should get the idea. By forming questions we How are you approaching the monster?
can turn a boring non-engaging closed ended ques-
tion “Did you watch TV today?” into an engaging
open ended question “What channels interest you So we have looked at how to set the scene to ask-
the most on TV ?”. ing questions more engaging by using popular
movie and pop culture references. We have looked
It will take some practice on paper but eventually the difference between open ended and closed
you will get the hang of it. Just identify the object of questions and how to change one type of question
the sentence and ask questions about the object. into another. Now let’s look at specific questions for
Answering those questions will lead the way to cre- Dungeon Master’s to start using in their games to
ating an open ended and much more engaging create a more engaging player experience.
question.

Mastering be able to ask open questions will not How did you do (Character Name)?
only improve the game experience for your players
it will improve many different areas of your life.
Why? The ability to ask interesting and engaging
questions makes you as a person more interest-
ing and engaging! What do you usually do?

How did that dice roll work out for you?

How are you approaching the monster?

What are you planning on doing?

How are going to get there?

How did you want to do that (action)?

What are you thinking about doing?

How are you thinking of doing that?

How have you used that in past adventures?

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When did you do that? Any last words?

Yes, actually I have a few! I hope everyone finds at

least one useful tip or tool that they can use to en-
When do you want to do that? rich their gaming experience whether they are a
Dungeon Master or a player.

Almost everything I put out at the DM’s Guild is

Where is this taking place? “pay what you want”. I have gone through through
some tough times and wished I could still have ac-
cess to things even though I didn’t have money for
them. So if your hurting don’t sweat it. If your doing
well and can spare a dollar it would be greatly ap-
Describe to me - How would you like to do that? preciated!

If you found value in this you may also appreciate

my “Secret Tactics for DM’s” guide.
Explain to me - Why are doing that? https://www.dmsguild.com/product/272252/Secret-
Tactics-for-Dungeon-Masters

What is going on now?

Resources
Downloadable content:
Tell more about yourself?
https://www.dmsguild.com/

What other actions did you want to do?

https://www.dndbeyond.com/

Online reference:
How did you arrive at that ?
https://www.dandwiki.com/wiki/

https://roll20.net/compendium/dnd5e/BookIndex
What’s your strategy going into this?

What will you do now?

What are you going to spend all that gold on?

What makes your player unique?

Why would your character do that?

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