3. How likely is it that the insights from this list of speakers and the agenda for this conference will help me achieve my goals?
Lots of conferences and workshops have great speakers. That does not mean a particular lineup is going to be valuable to you.
It's important to remember the adage, "What got you here won't get you there." Just like a child has different needs as it grows from baby to kindergartner to tween to college student, your business has different needs as it grows.
It is okay if you have grown out of what a particular speaker or conference has to offer, even if you found them incredibly valuable at earlier points in your career.
Take the goals you wrote down above and weigh them against what the conference you're considering is offering.
Do the speakers a conference is bringing in tend to prepare in advance or do they cram their slides together the night before? Are they known to always click through slideshows of their own work instead of presenting useful info?
Also, if a speaker said yes to speaking for free, they still need to treat the presentation as though they were getting paid and respect the investment the attendees made to be there by not phoning it in.
Anyone who does public speaking has given a presentation or two where they were "off", but if you are spending hundreds or thousands of dollars on a conference, you have every right to expect the conference producers to hold their speakers to a professional standard.
Have the speakers replicated their success?
To paraphrase an old saying – once is luck, three is a pattern. For example, if someone is speaking on pricing, have they successfully landed clients using that model at least three times? If the speaker is a business consultant, have they helped a minimum of three other companies successfully do what they are telling you to do?
Do the speakers have experience not only where you've been, but where you're hoping to go?
Do the speakers tend to be generous with the information they share or do they hold back out of fear you'll one day compete with them or to get you to hire them as a coach or consultant?
Are the topics being covered relevant to what you are hoping to accomplish? Do the speakers tend to offer the hottest advice from 2011 (or worse, 2001) but nothing connected to current market realities? Do they share examples from companies like yours overcoming a particular set of challenges or do they only share examples from Starbucks and Apple? (Yeah, yeah, we get it, the world's first trillion dollar company is doing a few things right.)
In my opinion, it is okay if not every session at a conference is a meat-and-potatoes session. A significant factor in business success comes from mindset shift: thinking bigger, thinking more strategically, discarding old fears and perceived limitations, or approaching issues from a different angle. These are things that aren't solved with a tidy formula and that you aren’t necessarily going to learn in a how-to session. Plus, if you're demotivated or in a rut, sometimes you need a "your dreams are possible" inspirational talk to get back to the best creative version of yourself.
Having how-to sessions on marketing, finance, and skill-set improvement are important, but they're not exactly super beneficial if you're in a place where you dread going to work in the mornings. Getting fired up again can be worth spending money on and sometimes you'll want a conference with an agenda that fuels you and your business both practically and emotionally.
4. Are the speakers and attendees people I want to network with and spend time around?
I believe that every person we meet is someone we can learn from. That does not mean I want to spend several thousand dollars and several days away from my family to be around just anyone. We all have limited time and resources and I want to be intentional about who I am actively listening to and surrounding myself with.
I also believe that the value of a conference is just as much about the attendees in the room as it is the people on the stage. While you may learn a lot and hit your educational goals from the conference sessions, you will learn so much more in the conversations you have with other attendees while sitting by the pool or hanging out after dinner in the lobby bar.
If you want to consistently earn six-figures in your business, one way to get there faster is to network with people who know how to consistently get to 7-figures (or 8). It requires a different mindset and you will learn a ton just from chatting during breaks or downtime. While there is absolutely nothing wrong with being in the beginning stages of business, attending a conference where you are much further ahead of the rest of the attendees may not be the best use of your time.
Sometimes I hear, "Why would I pay to make new industry friends?" The answer is simple: sometimes it's what you need. I have a friend who attended a conference specifically because she wanted to get to know a planner she had long admired for her ability to balance motherhood and running a successful business. As a mom with young kids of her own, she didn't care if this planner ever ended up referring her a wedding or not, she just wanted to buy her a glass of wine and hear about how she made everything work. While she could have just called her, it would have been unlikely she would have gotten a time slot on the planner's busy calendar. The conference was a place that afforded them both the time and opportunity to network, and there was value to both of them in paying to be in the same room.