One of the most common questions I get from artists and bands I encounter is how to book a show at a good venue. Specifically in Portland, everyone and their dog wants to play a Friday or Saturday night at the Doug Fir Lounge – arguably the best small to medium-sized venue on the west coast. However, it seems prevalent that most bands lack the knowledge or initiative to figure it out.

Fair warning here: I’m not going to candy coat this for you. I’m going to give it to you straight, which few people in this business will honestly do. So please, don’t mind my tone – I’m really a nice guy…but this approach is necessary here, trust me.

Although we may not be talking about rocket science, I will say that there is a bit of an art to booking a show at a killer venue. Not everyone has the personality for it either. As such, here are five steps to booking a show at a killer venue. It might not work for everyone… but it will most definitely work for those with initiative, finesse, honesty and solid communication skills.

1) Make sure you’re qualified to play at the venue.

You and your friends think your band rocks. You look cool…. You’ve got a killer Flash website… You’ve got a slick CD and it’s even available on CD Baby… You have some expensive gear and you feel like you’re ready for the big time.

Check yourself. Look at the venue’s show calendar and see what other bands are playing there on Friday and Saturday nights. Do you draw as well as these bands? Are you as well known as these bands? Have you played similar venues on Friday or Saturday nights? Do you think the booker has heard of you before?

If you can’t confidently answer yes to all of these questions, you’re probably wasting your time. Take a step back and reevaluate your strategy and get a better, more objective understanding of who you are and where you are in the food chain. Try starting at smaller, lower demand venues and do well there first. Play a few dive bars. Try doing well at a top venue on a week night. Build up a reliable draw. The bottom line here is if you can’t regularly draw close to 100 people, you have no business playing a Friday or Saturday night at a top club or venue.

2) Network with other bands that play the venue you’re targeting.

The #1, absolute most important skill in this business, without exception, is the ability to build relationships. This applies to everything a band or aspiring artist does, whether in business dealings, booking shows, hanging out backstage, making records, touring, licensing, radio, etc.

If you want to play a show at the Crystal Ballroom, you’d better have preexisting relationships with other bands that play at the Crystal Ballroom. This is valuable for finding opportunities to open or support other bands and for having a list of bands that you know well, so you can pitch the booker some lineup options. Remember: building relationships requires an investment of time and work. There are no shortcuts.

[Photo: Portland's Doug Fir Lounge]

3) Get to know the booker.

Simply sending an email to a booker, asking to play at a venue, will rarely get you a good response, let alone a show. If you don’t know the booker, consider yourself to be at the end of a very long line with slim odds of seeing the stage. Instead, take some time and get to know them.

Metaphorically speaking, think of the venue as the booker’s home. If you don’t know them, would you invite yourself over for dinner? Would you show up, uninvited and without knowing who they are or what they’re all about? Getting to know them first is crucial.

The first show I ever booked at Portland’s Doug Fir Lounge, I was working on behalf of a non-profit group who wanted to have a benefit show there. I sent an email to the DF’s superstar talent buyer extraordinaire and she responded that she was interested in the idea. I asked if I could meet with her to discuss some options for the show and soon after, I met with her over a beer and learned more from her about booking in one 40-minute meeting than I had known all together at that point in time.

Since then, I’ve worked to build a relationship with the booker, maintaining regular communication, getting to know her better and how she works, and making sure that she keeps me in mind for future opportunities.

And remember: every booker is different. It’s very important to get to know them as well as you can. Work to understand how they communicate, how they work and then ADAPT to meet their needs. For instance, if they communicate with short, two sentence emails, typed in all lower case – then you too should correspond with short, two sentence, all lower case emails. If they only answer the phone on Wednesday afternoons – then remember to call on Wednesday afternoons. Get to know them as much as you can, build a report, and make sure that you’re always on their radar for opportunities.

4) The squeaky wheel gets the oil.

Once you establish a relationship with the booker, effective and frequent follow-up is the key to success. A booker’s calendar is a crazy one to understand. It changes daily, catering first to the needs and changing schedules of national touring acts, then followed by a variety of special events and regional heavy-hitters. A booker will often book up to four three-band bills for one date, assigning each a “hold” priority, making sure they have back-up options for every scenario. As a date gets closer and things more certain, they’ll look to confirm with whoever is in the “first hold” position. If that artist can’t confirm, they’ll ask whoever has the second hold…and so on.

With things changing so frequently and with the booker’s calendar being so dynamic, it’s crucial to be in frequent contact with the booker, staying on their radar for potential opportunities. However, remember there’s a fine line between being persistent and being annoying. If you want to succeed, don’t cross the line. They have email filters for those who do.

[Video: The Dimes performing live at Portland's Holocene]

5) Kick some ass.

If and when you finally get the opportunity to perform at the venue you’re targeting, you’d better knock it out of the park. Anything less than a sellout should be considered a failure.

If you succeed at the first four steps, you’ll likely get an opportunity to play at the venue you’re targeting. However, if you don’t draw well and fail to impress the booker with excellent ticket and bar sales, you may risk the chance to play there again. This is a common mistake made by a lot of bands.

Once you get the opportunity, work hard to make the most of it. Have a strategy. Promote it like crazy. Let the world know you’re playing and make sure EVERYONE you know makes it to the show. Do whatever it takes to sell the place out. Play the best show you can and let everyone know about it. After the show, follow-up with the booker, thank them for the opportunity, and ask if you can get a hold for another show in the future.

Repeat steps 1 through 5 and never stop. Always work to improve what you’re doing, getting better and increasing results every time. If you’re not getting better and improving as you go, you should probably stay in the basement.

Here’s a short list of my favorite venues in Portland, Oregon:

1) Doug Fir
2) Holocene
3) Mississippi Studios
4) Someday Lounge
5) Wonder Ballroom
6) Crystal Ballroom
7) Jimmy Mak’s
8 ) Laurelthirst Pub
9) Mississippi Pizza Pub
10) Alberta Street Pub

[Photo: The Dimes performing live at Mississippi Studios]