Checkpoints and Check-ins That Make You a Great Leader

Checkpoints and Check-ins That Make You a Great Leader

Having a Team You Can Trust means leading the team and providing opportunities for their development. There’s no one-size-fits-all solution to putting the support and engagement your team needs in place because everyone connects differently. 

According to Gallup’s latest numbers on employee engagement, ONLY 34% of staff are engaged. Individuals who are engaged are loyal to the company and emotionally committed to getting the job done well.

We’ve worked with hundreds of entrepreneurs and Executive Assistants through Priority VA, and we’ve determined that every dynamic relationship hinges on 4 Key steps every Founder takes responsibility for. Equip Them. Empower Them. Encourage Them. Engage Them.

Establishing Checkpoints and Check-ins with your team is a vital part of being a trusted leader and feeds into each of these key steps.



Checkpoints happen at naturally occurring times during the course of work. For instance, during a special project or launch, you would have checkpoints at the beginning, middle and end, maybe even a post-launch look back after the dust has settled. You’ll want to cover each of the 4 E’s during these Checkpoints. 

Equip: Does your team member or EA have all the equipment they need, software access, passwords, tools to do the job in relation to the project/launch?

Empower: Have you made your expectations clear and delegated (using the 6 levels of delegation) so your team knows which decisions they can make and the boundaries around those decisions?

Encourage: Show up for your team, in person, on camera, for all the calls you say you will. Your time is your most valuable asset, so giving of this time to your team says a lot about the respect you have for them. LISTEN more than you talk, which shows you value their opinions/perspective. In the heavy, heavy part of your launch/special project, send a ‘thank you’ text or instant message.  

“A pat on the back is only a few vertebrae removed from a kick in the pants, but is miles ahead in results.” — Ella Wheeler Wilcox

Engage: While this is a business, and no one is denying that fact, there comes a point when you should engage your EA and team on a deeper level in order to create longevity in the partnership. In order to reap the full benefits of all-in support from your EA, you have to treat them like a partner. This can be as simple as changing the way you speak. A “Boss and Employee” have a very different relationship than a “Leader and a Team Member”. What visuals popped into your head as you read that last sentence? And which one do you want to model in your leadership? 



Check-Ins are not attached to projects or launches, so they must be planned with intention and forethought. You can do quarterly or monthly check-ins, or even twice a year. We do NOT recommend only doing this once a year. If you’re waiting THAT long to check-in with your team, do you really care about them, or just what they can do for you? 

Equip: Has your EAs role changed? Are you asking more of them or asking something different than originally planned? Do they need training to grow into this new role or responsibility?

Empower: Do you find your EA asking your permission on a regular basis? Are these decisions you want them to make without consulting you? If so, you’ve got an empowerment problem. Grab your 6 Levels of Delegation worksheet and discuss the issue, making sure you hand off the decision to your EA with the parameters they need to feel confident filling this role. 

Encourage: Come to this check-in meeting ready to recognize your EA’s contributions in the past quarter. If you are talking about the team’s wins during your weekly meetings, this should be an easy thing to do. When you share these with your EA, as their leader, you are reinforcing what wins made the biggest impact in your business and what you would like to see more of. 

Engage: Start your weekly meetings and check-in meetings by asking about your EA’s weekend. Share yours as well. A relationship isn’t built on a to-do list, so get to know your VA personally. Learn the names of your VA’s family and find out how they like to spend their weekends. Getting to know small details of each other’s lives will develop a kinship that will ultimately reflect in your business. 

Building a team you can trust takes a lot of time, energy, and investment. But the return on that investment will pay dividends for months, quarters, and even years to come. 

“Equipping is raising people to a place they never thought they could get to.” – Andy Kerr

If you’d like to discuss how to Equip, Empower, Encourage, and Engage your team or EA, schedule a free strategy call with a Certified Momentum Method Strategist today.

If you’re interested in learning about what an Executive Assistant can do for your business, schedule a strategy call with us.

Our virtual team experts will help you determine how your business can benefit from our Priority Executive Assistants.

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