The One Group Every Entrepreneur Needs to Join

Accountability groups come in many forms, but the basic premise is the same: a group of small business owners, freelancers and/or entrepreneurs join together and commit to regularly sharing their goals and progress towards them. Many groups are virtual: mine includes women who live in Florida, Texas, New York, and Utah. They often include weekly online check-ins, plus regular calls and maybe occasional in-person meetings. 

I estimate that I spend about one to two hours a week thinking through my weekly plan and engaging with other members — but it’s all time that moves my business forward. There are many ways to approach it: join a paid group like Savor the Success (the one I’m in) or set up your own group (note that you’ll likely have to take on the role of facilitator).

I talked to Jennifer Dawn, President of Savor the Success, about how to find or start the right group and get the most out of your experience. Here is what she recommended.

Getting Started

1.  Pay to Play or DIY? Yes, we all love a bargain and running a business means cash is always short, but accountability groups are a perfect example of “you get what you pay for.” By paying a relatively nominal amount (anywhere from a few hundred to few thousand dollars, depending on the length of the program — some are a year long!) you and your co-members become invested in the experience and are more likely to show up. Think about when you sign up for a 6 am boutique fitness class and then have to drag yourself out of bed so you don’t forfeit $25 — it’s the same strategy. A payment also goes towards a leader who guides the conversation, makes sure everyone participates and can help the group with mastermind sessions. A few virtual options to try: PowerWeek, AccountabilityWorks, and Savor the Success.  Or go to and search for “accountability groups” or "Mastermind groups” in your area. Local business chambers and co-working facilities might also be able to point you towards a group.

Alternatively, there’s the option to create your own. Once you gather a small group (Dawn suggests two to five people for phone and online meetings, four to eight people for in-person meetings), set a defined trial period of a few months, and set times for weekly check-ins, calls and meetings. Set up an easy, mutually accessible way to check in (like a private Google doc or folder) and create a Google group for email messages and reminders. 

Need members? Decide if you prefer local and in person or a group that connects via phone and online to help guide your search. For a local group, try posting on Meetup, Facebook or LinkedIn, or post a notice at a local co-working facility or your chamber of business. Even your accountant or lawyer might have other small business owners they can connect you with. 

For a virtual group, try reaching out to active commenters on business blogs you love: they might be just the type who want to get involved! Or do a LinkedIn search and send messages to the type of people you’d love to have join.

2.  Make sure people “get” you. For example, if you’re the only lawyer in an accountability group of accountants, you might not understand each other’s businesses or struggles. But if you’re all new moms trying to juggle your independent legal or accounting practices, you might. A common bond — whether business or personal — can help you work better together. 

3.  Be at the same stage. For a good fit with an accountability group, it’s important that every member be at approximately the same stage in their company growth trajectory or career. Otherwise the gap between junior and senior members may cause some people to feel like they aren’t getting anything out of the group. Groups like Savor the Success first separate members based on annual revenue, which is a straightforward marker, but you can also look at years in business or other milestones, like raising a seed or A Series investment round. 

Getting the Most Impact

1.  Come in with an open mind. This is Dawn’s number one piece of advice and the surest way to make your time impactful. Other members may offer thoughts or advice, and it’s human nature to dismiss things we’ve already considered. But be open to reconsidering things from new angles. Know that your accountability group can sometimes detect blind spots that are hard to see when you’re in the trenches of your own business.

2.  Be all in. That means prioritizing check-ins, supporting your co-members and showing up 100 percent for group meetings. Dawn even recommends blocking out a few minutes before meetings to get ready and in the right mindset. I’ll be honest: the first few weeks in my accountability group felt a little forced and cheesy, but I committed to participating as prescribed for just one month. I blocked out 30 minutes on Monday and Friday, and made an effort to post meaningful weekly plans and truly read and comment on the posts of my fellow members. By the end of that month I was hooked — and my group felt like close friends.

3.  Drop the BS. In our regular lives, we often have to be a face of optimism, whether it’s to provide a great face for employees or partners, or simply to keep things cheery on social media. But you’ll get more out of an accountability group if you drop the front and be vulnerable. To facilitate this you can even think about asking members to sign an official or de facto confidentiality agreement — just like Vegas, what happens in the group stays in the group. It’s only by being transparent and honest about your day-to-day and big picture business struggles that others can step in and help.

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