Getting started with your accountability structure:
Choosing an accountability partner:
You're going to have to share everything with this person. All the good. All the bad. Mistakes you've made. Successes you have. There are going to be very hard conversations when someone is slipping. Can you be strict with them?
You don't interview this person, it just kind of has to naturally happen, but asking formally to enter into this is a must. Being in the same boat usually helps. One person isn't better or worse than the other, they simply have different strengths and weaknesses that can be learned from.
Set up a schedule:
Pick what works for you. In the beginning we chose to meet weekly. We would meet for one hour, giving 30 minutes to each of us. We even had a corresponding Google spreadsheet with our projects and their timelines.
After 6-8 months or so, it wasn't really working for us. We decided to go every other week, and forego the Google spreadsheet. That took some of the pressure off, and make it so we had more headspace to achieve what we were trying to achieve with a bit more time.
Create Motivators / Punishments
This seems counterproductive, but it's actually a good motivator. It could be anything that would keep both of you in this. When you set up a schedule, don't back out on that person last minute. They're making it a priority so you should too.
For example, our punishments were monetary ($5 via Venmo to the other person you skipped out on), as well as social ridicule. We could tweet, post, blog, etc. about how much of a jackass the other person was for bailing, if we see fit.
Give Each Other Challenges
Once you've gotten into the rhythm of accountability (possibly a few months), see if you can issue a 30 day challenge to someone based on what you've been hearing them say they want/need.
For example, I had challenged my partner to focus. He was constantly in love with the new shiny idea of the week, and would cast idea previous ideas/projects easily. Part of this included saying no when possible, but another part of it was focusing his time better. The challenge was to manage time better to support the initiatives important to him, and that meant not watching TV until after it was dark out, giving him a few extra hours each day to do something productive.
My challenge from him was that I was struggling to be healthier. An "easy" thing to do was to cut out soda (which I had roughly 1 per day) for 30 days.
The results were that I cut out soda, as well as coffee (with sugar & milk) every morning and never went back to it. He also stuck to his end of the deal as well and spent more time reading, golfing, or at work.
Have Check Points
In our weekly sessions we discussion what happened that week in the areas of Life, Work, and Health. And at the end of our time we clearly outline what our next steps are for the next two weeks and what we'd hope to achieve.
In December we held our first year end session. We went to dinner for two hours and came with pre-written lists of everything that went well, didn't go well, and what our 2015 goals were for Life, Work, and Health. In the end we felt we had a fairly clear roadmap for the upcoming year, and had done a lot of great groundwork in the previous year.
Like with any good project, you just need a plan and an outline. With our structure we're able to keep things fluid and well, accountable. When you start, you'll do what works best for you!