Be a More Connected Leader with One-on-one Employee Check-ins

 

Here’s the thing about leadership: In order to be good leaders, we have to be connected with our teams.

You need to understand what your employees enjoy about work, what they don’t, and what motivates them.

You need to be able to help them identify anything that’s holding them back and remove those barriers.

The problem is it’s easy to get swept up in daily routines and never set aside the time to intentionally connect with your employees and talk about the bigger picture.

I’ve started doing one-on-one quarterly check-in meetings with each of my team members. It’s been a great way to stay connected and identify any improvements that my employees can make or that I can make as a leader.

 
 

Example questions

  • How are you feeling about the work you’re currently doing?

  • What do you enjoy most?

  • What part of your work drains you?

  • What new skills would you like to learn?

  • Are there any tools that would help you in your job?

  • Are there any conferences you’d like to attend?

  • Is there anything I can do to help you improve?

  • What do I do that makes your job more difficult?

  • What can I do to be a better leader?

Additional conversations

  • Raises (annual basis)

  • Shifts in responsibilities

  • Their career plans

  • Knapsack’s future plans

As you have these conversations, make sure that your employees know that you genuinely care about how they’re doing and that you’re open to constructive criticism yourself.

When you start having one-on-one check-ins with your employees every quarter, I believe you’ll create a healthier work environment, improve your leadership skills, and be more connected with your team.

 
Knapsack

Knapsack Creative is an award-winning Squarespace design and SEO agency helping small businesses turn their websites into growth engines. We specialize in building sleek, high-converting Squarespace sites powered by the StoryBrand framework; so your message is clear, your brand stands out, and your site actually generates leads.

From consultants and creatives to financial professionals and service-based businesses, we design with strategy at the core: blending modern design, SEO optimization, and conversion-focused storytelling. Our team has launched hundreds of Squarespace websites that don’t just look beautiful, they win trust and deliver results.

Whether you need a one-day website build, a full redesign, or an SEO strategy to rank in local search, Knapsack Creative makes it simple, fast, and effective to get online and grow.

👉 Trusted by 1,000+ businesses nationwide. Featured Squarespace Experts.

https://www.knapsackcreative.com
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