I'm always inspired how people are able to get up in front of a crowd (big or small) and deliver a drasha or dvar Torah that is really good. How does one go about preparing a drasha? What's a starting point? Do you pick something from the parsha, something from inyunei d'yoma. How can one make it "geshmack" (tasty) to listen to for other people? Obviously a breadth of knowledge in Chazal, Halacha, Sifrei Drush, chassidus, musar, medreshim, etc will be a tremendous help. However sometimes even with this or the ability to find this information easily it's difficult to put something together that people will enjoy and not be bored from or not interested in. I'm talking about short to medium length drashas, not long ones and not "shiurim" in a certain inyun. Ranging from 5 min to 20-30 min. Where does one begin?!
I'm not a rabbi in any sense of the word, but I have given a few divrei Torah that I was proud of, and that were well-received. Here are some steps/tips I can think of:
This week's Torah reading (or holiday Torah reading or perhaps haftara) is always a good place to start. It's always appropriate, people have it in mind already, and it contains a bunch of different potential topics to work with.
Look through the reading for something that grabs your attention for reasons such as:
It's a topic that interests or moves you.
It's somehow thematically connected to the context of the devar Torah (e.g. if you're speaking on the occasion of some celebration).
Your favorite commentary has a lot to say about it.
Once you pick something (or in the process of picking something), see if either there's an interesting feature of the text that you want to investigate or there's an interesting comment from one of the commentaries. That point will serve as the core of the devar Torah.
Now, start thinking about things you can say about this point:
First of all, what the interesting point is, in your own words
Why it's interesting
Why you care or even are excited about it
How it connects to the context (e.g. the celebration at hand)
Some story, joke, other Torah point, etc. that it relates to
Make a brief list of these points on paper.
Look at the list, and think about what would be good to open with, what would be good to close with, what needs to follow what, and what transitions you can make from one point to another, then tentatively number the points in the order you think you'll hit them.
Using this list as a rough outline write out a fully-written speech, word for word. Whether you end up saying those particular words or not, going through this process will help you come up with good phrases to use and will help you be sure that the devar Torah will really hang together. Some writing tips:
Try to make everything work together using good transitions, referring back to shared themes, and reminding listeners at the end what you started with at the beginning.
Be enthusiastic. Don't be afraid to show your love for Torah and your interest in the topic at hand. Feel free to use the word "I" in relating personally to the material, as in "and then I found this Rashi that just blew me away." If you care, so will your listeners.
Also, feel free to address your listeners directly as in, "Listen to these beautiful words of the Ramban," or "What do you think he meant by that?"
Have a beginning that gets people's attention (e.g. a joke, an anecdote, a headline, or a really intriguing question).
End on a positive, enthusiastic note. "Bimheira viyameinu, amein!" is fine, if it fits, as are "Mazal Tov!", "Lechaim!", or other words of blessing. The main thing is that you don't want to peter out into something lame along the lines of "and that's what I have to say about that."
If you discover that some of your points don't really fit in the written flow, feel free to cut them. If you think of other things to include along the way, feel free to add them.
Read the written speech aloud, and pay attention to things like:
Does it sound good?
Is it easy to read, or are there tongue-twisters?
Are there awkward repetitions of words or phrases?
Does it makes sense?
Will the various people listening understand what you're getting at? Will some need additional context?
Do the transitions make sense, or will you lose your listeners by jumping around?
Make edits as you go, then re-read.
Cut out anything that isn't effective at helping you make your point. Err, at this point, on the side of cutting. If you say something interesting, appropriate, clear, and coherent no one will complain that it's too short, ever. On the other hand, the longer it is, the more chances listeners' minds will have to wander, and the more likely that someone will consider it too long.
If you really want to deliver it well, practice reading it slowly and clearly a bunch of times, until it really sounds good to you. You may find more to edit as you go.
Regarding how you read the devar Torah, there are two choices, each of which can be useful: either read the speech word-for-word or break it down into an outline and work from that. The latter allows for more natural-sounding delivery, if you're confident that you can remember what you want to say and (close enough to) how you want to say it. The former makes it easier to make sure that you hit all the points and phrases that you worked so hard on.
Either way, as (or right before) you're giving the devar Torah, if an interesting or amusing ad-lib occurs to you, go for it! There's no reason to turn off your creativity and engagement with the material just because you're finally delivering it. One good example of this would be if what you're saying relates to another speech at the same event.
Speak slowly, clearly, and loudly enough for everyone to hear. Just as you are very unlikely to speak for too short a period of time, you're also very unlikely to speak either too slowly or too clearly.
Try to make eye contact with as many people in the room as possible.
Use expression in your voice and gestures with your hands to make it clear that you're alive. Another "unlikely": You're unlikely to come off as too enthusiastic.
Take advantage of the ending you wrote to end strong, with enthusiasm. Don't peter out.
To do this really well can take a whole bunch of work, but saying something that people truly find interesting and worthwhile can really make it worth it.
Just as different commentators have different styles and approaches, so to with those giving divrei torah. While no one is locked into one approach, in my experience people tend to have "favorite" approaches. In my minyan, where this duty rotates, I know that Person A is probably going to jump off from some problem in the pshat, Person B is probably going to look at it in terms of historical context, Person C is probably going to draw on midrash, and so on. Any of these people might surprise me in any given week, of course, and if you don't yet know what approach you're most comfortable with, try several and see what works for you.
The following thoughts are drawn from careful observation (particularly of my rabbi, who I think excels in this area) plus some seminars designed for lay leaders.
First, know your "audience". What is their level of learning? What are they used to from other speakers? If it's your community you know this already; if it's not, you'll need to do some investigation. A d'var can be objectively brilliant and still fall flat because the listeners were either lost (insufficient background) or bored (tell me something I don't already know). A d'var is given in a context, not in isolation. (This is less true when you're publishing on the Internet, perhaps, but you asked about speaking.)
Second, choose a manageable amount of material to cover. A d'var torah that tries to cover an entire parsha in five minutes is going to be shallow and cursory; my advice is instead to pick one thing in it as a jumping-off point. Maybe that's a problem in the pshat ("how could he do that?"), maybe it's a "minor" side story like the wood-gatherer in Sh'lach, maybe it's a seeming oddity in the text ("male and female he created them?"). From there, you can draw on commentaries or midrash; your goal shouldn't be "survey what everyone says" but to build toward some point, selecting commentaries etc as appropriate. This next part may not work for everybody, but I, following in the footsteps of my betters, try to make it "relevant" somehow. Studying torah for its own sake is great, of course, but when I give a d'var I want people to come away with some idea that they can apply in their lives. It won't always be a big, grand thing; it may be something small. And sometimes it may not be an action but a new way of looking at something familiar. But in my opinion a good d'var causes the listener to feel some investment in what you said, something he'll do or think about differently now.
I've been talking about the parsha as a starting point, but the calendar can also serve this purpose. Early in Elul you might talk about t'shuva and draw on Psalm 27 or the feelings the daily shofar blast evokes, for example. I once gave a d'var during late December about assimilation. Sometimes something going on in the community, either local or broad, will serve as a starting point.
Now, some thoughts about "nuts and bolts":
What you identified as your starting point may or may not be the first thing you say. I have heard (and I think given) successful divrei torah that start out by telling a personal story/reflection, and then partway through the relevance to the parsha/calendar/community issue/whatever emerges.
A homelitics teacher gave me the following advice: always write out your talk in full beforehand, even if you're planning to speak from notes. I've found that this helps me to get the details of flow, pacing, etc right; if I just practice from notes, I'm more likely to say (during a practice run) "ok, that part's rough; I'll fix that next time" -- and not actually do it because I lose track of it.
As implied by the previous, practice your talk. I am always torn between reading the text I wrote, which will provide higher-quality content, or speaking from notes and thus more-easily making eye contact and otherwise connecting with people. A more-proficient public speaker would be able to speak from a written copy and still look like he's talking to each person in the room; I'm not there yet. So there's a trade-off, and what your community is used to should inform how you handle this. (If you do read, try to find some sections that you know well enough that you can look up!)
If you're going to read, prepare your copy for that. Don't just print out your talk in 12-point text (or whatever) and read that; find a size and line spacing that works for you. I break lines at phrase boundaries (commas or periods) to make delivery more natural. I mark up my typed copy, underlining places to emphasize, marking longer pauses, etc. Make any annotations that will help you give a more dynamic rendition.
Time yourself in practice, and know whether public speaking tends to make you speed up or slow down. Aim for your community's average length.
The best speakers don't waste peoples's time. They know their material [almost] by heart. There's few things more annoying then a speaker stumbling through a Pasuk or commentary, or even spending time finding it. Write it out or underline it in a book and bookmark the page. Then read it until you know it almost be heart.
Respect your audience's intelligence. There's no need to translate, for example, וַיְדַבֵּר ה' אֶל מֹשֶׁה לֵּאמֹר - even, if, for some reason, you deem it necessary to quote that verse.
Know your speech. Say to over to yourself a few times without notes. It's OK to have a few versions of it - and the delivered one may be another version. It needs to flow to be good. Some notes are good; reading it is a recipe for a not well received Drasha.
When speaking to an Israeli - or very learned - crowd: Remember they understand Hebrew, and it's worse than ridiculous to try translate things to them. I see American speakers doing this all the time. If you're not explaining a difficult passage, then assume they understand what you quoted - probably better than you did.
My advice is to keep an eye open for dvar torahs/chidushim you find really interesting.
when this happens, write it down. it will become basis for your next drasha.
when you're excited about something it makes the drasha much more interesting to hear and will make a deeper impression. it will also be more intersting for you, since you can research and develop the idea you found interesting.
The Maharal (in his introduction to Tiferes Yisrael) writes that teaching Torah is hard for two reasons: 1. He has to intend to instruct his student in the truth. 2. The student has to accept what he is saying.
Therefore, the way to be saved from either of these pitfalls is to align his actions with G-d's desire, because G-d is the one who gives a person knowledge, and He can guide a person to the truth.