Level up your support career

Level up your support career: Create an accountability group with your peers

This article is based on my talk at SDX 2017. 

I want to start with a question, a question that brought you here today: what do you want out of your career?

Do you know how to get there?

Do you have anyone that will hold you accountable?

I serve entrepreneurs. ConvertKit is an email marketing platform for professional bloggers. These are business owners, who will do whatever it takes to succeed. One of their most popular tools for success—a mastermind.

Some of the most successful bloggers, making six figures a month, credit masterminds as being key to their success.

What I want to do take this concept and show you how it can help you grow your support career, just as entrepreneurs are using it to grow their business.

What is a mastermind?

A mastermind is a peer group, supporting each other toward similar goals.

In our context, a mastermind would be a group of support professionals, like me, like you, and getting together on a regular basis to help each other achieve our career goals. We would hold each other accountable, track progress on specific goals, workshop problems from scaling support to dealing with your boss to developing necessary skills. 

A mastermind is not mentorship.

The true power of masterminds is that everyone in the group is starting from a similar level, working towards a similar goal. Mentors are great, but they are one piece of career development. A mastermind group is another.  This is because a mastermind is reciprocal: you give what you’re good at and you learn what you aren’t.

A mastermind helps you answer hard questions.

In support, we’re faced with hard questions, from solving challenging customer problems, to building a customer philosophy, to scaling our teams. Your mastermind will be full of other people that are solving these hard questions too, and you can learn from their solutions.

A mastermind holds you accountable. 

A mastermind helps make sure you do what you say you’re going to do. You can set milestones for your career and have a group of people help ensure you reach them. 

The elements of a successful mastermind

Common Goal

It starts with my original question: What do you want out of your career? This question should be the driving force behind your mastermind, because your ideal career path should be similar to that of your mastermind group members. 

For me, I’m interested in leadership. I want to be a better leader, grow my team and the responsibility that I have.

When I’m looking for my support career mastermind, I want to find other people with a similar ideal path. We should all be working towards closely aligned goals. 

I know many support pros find out how to grow your career without moving into leadership. Masterminds are a perfect application to this kind of goal as well! A mastermind can be a group of support pros learning to code and supporting each other though the process, for example. 

Common Ground

A mastermind should truly be a group of your peers. That means your mastermind group should be other support professionals that are approaching your common goal with a similar timeline or shared experience with you.

My goal to grow into leadership, specifically at the director level. This is as high as it gets in my company. Other important considerations are that I work remotely, I work at a SaaS, we are a startup, and I've been with my company for almost two years.

When I’m forming my mastermind, I need to find people not just with similar goals, but with a common ground. I could look for people who have been with their company for almost two years, I could look for other support professionals at a startup, other people that work remotely. I want to look for a group that wants to achieve a similar goal to me, while facing a few similar challenges. I do want to be careful not to find people too similar to myself--otherwise I won't learn anything new! 

For our group that is learning to code together, each member should have a similar skill level—you should all be beginners, or all be comfortable, but want to get better. 


How big should a mastermind be? 

I believe the perfect size of a mastermind doesn’t exist. A mastermind can be two people, 5 people, 8 people. If you’re creating your own mastermind—which I hope you all go out and do after this talk—you have to think about where you thrive. Is it in a partnership? Is it a small group? Is it larger? Once you know, find others who feel the same way.

Meeting Structure

So what does a mastermind meeting actually look like? 

Some important considerations:

  • Are you meeting virtually or in person? 
  • Are you meeting weekly, monthly, quarterly? 
  • How long is your meeting?

Once you know this, you can figure out your structure. There are two main structures: 

  • each meeting focuses on one group member, in what’s called the hotseat. 
  • each meeting focuses on a few or all group members. 

When thinking about your structure, it's also important to return to your goal. The type of goal you have will influence the structure you should use. 

Our group that is learning to code together would do well with each meeting allows everyone the spotlight, even just for a few minutes. This allows everybody to check in on the status and be able to take immediate action after the meeting. This group has an obvious path to success— there are concrete steps everyone can take to achieve the goal.

Returning to our leadership goal example, I would recommend this group focus on one group member per meeting. This allows a deep dive into specific problems, relationships, etc. The reason is because the goal of leadership is what I would consider nebulous--there is no obvious path or exact steps to take to achieve this goal, it will be different for everyone. 


I mentioned the hotseat—and this is one of my favorite aspects of a mastermind. 

When you do one hotseat a meeting, if you’re meeting for an hour, 45 minutes should be focused on your hotseat. This is the time to workshop your biggest struggle, or opportunity in your career right now.

When you do a couple hotseats a meeting, each member should get 10-15 minutes for their hotseat. There isn't necessarily time to dive deep, but there is enough time to talk through a current problem. 

What happens in the hotseat? I'll give you an example from entrepreneurs, the hotseat OGs. An entrepreneur might use their hotseat as time to plan out a launch for an upcoming product. They can talk through the marketing plan, strategies for ads or direct outreach, some lessons from their last product launch. 

For our leadership mastermind, a support pro could use the time to talk about their latest performance review, or feedback they got from their boss. What they can do to act on it, and how they can make sure to have better results during their next review. 


Preparing for your hotseat is crucial. It means that you won’t waste your hotseat trying to figure out what you need help with. You’ll get to spend your forty short minutes focused and effectively. Maybe you’ve done the hotseat before, or maybe it’s your first time. Either way, the best way to shake the nerves is to get prepared. Spend some time a couple of days before your hotseat gathering your thoughts. How do you want this hotseat to go? What are you excited to share with your group, and what are you struggling with?

But don't stop at your own--prepare for other people’s hotseats too. Taking a few minutes before each hotseat to research your group member's company, industry, review notes from the last few meetings, can make a huge difference in the quality of feedback you can give, and your group member's trust in you. 


Commitment to your mastermind is important, and it’s ok to require it from your mastermind members. You should take your mastermind as seriously as you take your career, and that means showing up. 

I generally recommend agreeing to a timeline beforehand—if you’re meeting weekly, agree to six weeks. At the end of six weeks, reevaluate if the mastermind is working for you—an easy out. 


It is important to be open and honest with your group members. 

Being open and honest with your mastermind group is one of the most important things you can do, and often the most overlooked. 

You never know what other group members are experts at, until you share. Maybe a group member is an expert on a topic, like traffic building, or has a particular skill or love of numbers and analytics. They can help you dig into not just the what, but the why. 

If there’s anything I’ve learned about any sort of business, it’s that there’s no such thing as separation between business and personal. That can include a day job, or no job, your relationships, your family. Your mastermind group doesn’t need to become therapy, to come air all your problems, but there are times when your relationships or your other work can impact you and your business, and you need to be up front about that. 

Don't get defensive

When you're defensive, you’re putting a wall up, you’re pushing your group away. When you do that, how can they help you? 

The easiest way to overcome defensiveness is to shut up. If your immediate reaction when you hear feedback to explain why you made that choice, to quickly say something, anything that proves you’re not an idiot, don’t say anything at all. Just listen. You have to bite your tongue. Let them finish their thought. Then wait. 

Hear an outside perspective and how someone else is perceiving you. That’s the most important thing you can do. I’m not telling you you’re going to find enlightenment and be relaxed about everything, but you’re going to get advice. You can take it or leave it, but at least you've heard it. 

Where to start?

Ok. You get why you should start a mastermind and the things that make a mastermind great—so where do you start?

Other people are a pretty important to your mastermind!

When you’re looking for your people, my suggestion would be: don’t group up with any co-workers, as much as you trust them. One important aspect of mastermind is diversity. Diversity in experience, industry, company type. As different as your group members can be from you, the better—considering you should have common goals and common ground.

Where do you find other support professionals? 

The Support Driven Community is a great place to start--and if you're already a member, then you're in luck! I'll be hosting a round of Support Pro Masterminds within Support Driven. You can sign up here to be notified as soon as it's ready: 



So we’ll return to my initial question: what do you want out of your career? You can find other people who want the same, and you can all get there together.