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How to Choose a Great Team—and be a Great Leader

“No man is an island.”

“There’s no ‘I’ in Team.”

“Teamwork makes the dream work.”

 We’ve all heard these motivational quotes time and time again. As cliché as they sound, they’re so true—especially for creative entrepreneurs. Why? Because if you want to achieve Oprah-sized dreams with your business, growing and scaling is essential. So how do you grow? How do you scale? And most importantly, how do you inspire a team to be onboard with that vision? (Notice I said inspire instead of lead—we’ll get to that.) Let’s break it down.


What positions do I need to fill?

First, you know you’re ready to hire when you can no longer keep all the plates spinning in the air. Letting details fall through the cracks is scary and can be detrimental, but the good news is that it’s preventable. You’ll want to make a list of #allthethings that you’re responsible for in your business, everything from accounting to blogging. Then, categorize them by the tasks that you love most—you know, the ones that make your heart pitter-patter. Make another category for the tasks that you’d rather walk on Legos than do. (For me, that’s bookkeeping.)

From there, you’ll start seeing trends. Maybe you hate reconciling your accounts at the end of every month, but you’re a rockstar at blogging. If so, you should probably hire a bookkeeper. Or maybe you hate getting stuck in email, but you love connecting with clients in person. That means you might need a virtual assistant. The goal is to bring on ideal team members to take some weight off your shoulders in order to give you the freedom to do more of the higher-level tasks.


How do I choose the right people?

Now that you have your list of tasks to hand off and you know the type of person you’re looking for, it’s time to develop an interviewing system. When working with my wedding venue clients, I instruct them to make an online questionnaire, whether they’re looking for someone to be on site or a virtual team member. There are several platforms to choose from such as Survey Monkey or Typeform.

You’ll want to keep the questionnaire short and sweet for two reasons: 1) candidates don’t want to fill out a lengthy form, and 2) you don’t want to read through lengthy answers. I suggest having 3-5 questions, with the last question being something totally irrelevant to the job that speaks to their personality and gives you a hint about whether or not you would get along with the candidate. For me, Sundays are sacred and I never work on Sundays, so my last question is asking them to describe their perfect Sunday. This one answer typically tells me more about them than the previous questions that actually pertain to the job itself.

Set a deadline and post the search in Facebook groups, online forums, and even spread the word in your local community. Once the deadline has passed and you’ve read through all of the forms, select 5-8 people to have phone interviews with. Your top three phone calls can move on to in-person interviews. If you have a tie between two from the in-person interviews, then I’d suggest having both of those candidates meet the rest of your team. Or, if this is your first time hiring, have both of them do a working interview to see if they can handle the tasks at hand. Give them a test project and let them know that they will get paid for their effort. You’re judging the quality of their work, but also how efficient they are at completing it.

I do want to note that at some point in the process, it’s a good idea to have the potential employees get to know the existing members of your team (if you have any). Cultivating comraderie is so important and it’s something we’re about to talk more about.

OK, so you have your dream team. Now what do you do with it? Clearly, you’ve rocked onboarding, they’ve slayed their training, and you’re all living in entrepreneur heaven—but what’s next? How do you keep great coworkers happy so that they not only stay with you, but they thrive with you?



Here are 7 ways to be a great leader:

1. Be compassionate.

I’ve never liked the word “boss”. Aside from using it in fun memes or as a loving term toward a friend, it feels icky to me. When I hear it, I think of the cold corporate world I once lived in and the “boss” I had to report to every day. Bosses strike fear in order to get results, whereas leaders inspire and encourage. Their coworkers know they truly care about their well-being. So get to know your people personally. Hang out outside of work. Ask about their family or how they’re doing. People who feel appreciated will always do more than what is asked of them.


2. Eat last.

One of my all-time favorite books is Leaders Eat Last by Simon Sinek. If you’re a business owner looking to grow your team, I highly suggest you read it and take to heart every word Sinek writes. What he reveals in his research is how the best leaders foster trust and cooperation with their team by being self-sacrificing. By learning how to create and implement a safe space for your team, you’re giving them security within the walls of your organization—which gives them a sense of protection from outside challenges.


3. Invest in people.

With my planning company, I make sure that my team knows that I’m invested in their interests and want to support them. One of our planners enjoys calligraphy, so I surprised her with an online calligraphy class. Another planner is inspired by out-of-the-box design ideas, so I’ve taught her how to do editorials and let her know that I trust her to take that area of the business over. Your budget doesn’t have to take a big hit to invest in their interest, but simply showing that you’re interested in the things they’re passionate about and supporting them however you can is important and makes your team feel valued.


4. Earn respect.

Gaining and keeping someone’s respect is a privilege and something that must constantly be pursued. To earn a teammate’s respect, you must be decisive and self-confident. If you aren’t confident in your choices or the direction you’re headed, why should anyone else have confidence in you and the path you’re leading everyone down?

You also have to lead by example. There will be times that you ask your team to do hard things. You need to be right beside them doing those hard things with them. Athletes have more respect for the coach that runs that 5 a.m. mile with them than the coach that sits in the bleachers and watches them gasp for air.

Finally, stand tall and take the hit. You and your co-workers are going to make mistakes. When the mistakes are yours, own up to them and apologize. And when your co-workers make a mistake, show empathy, and support them by turning it into a positive learning experience.


5. Compliment in public, criticize in private.

When my husband and I were going through our pre-marital counseling, our pastor told us to “compliment in public, criticize in private”, and it has been one of the main pillars that the foundation of all of my relationships are built on. Correcting someone in public will immediately put them on the defensive and they won’t hear the lesson. Inversely, public praise elevates their sense of accomplishment. Always, always give credit to your teammates when they’ve made an achievement, big or small. Even if you were the one who accomplished a goal, gracefully accept praise while giving credit to your team, because without their help or support, hitting that goal would have taken a lot longer.


6. Don’t dictate; delegate.

No one likes a helicopter boss hovering and micromanaging. You hired each person because they possess a skill that you need. You need to trust them to do the job at hand. I know releasing control is scary, but start with small steps, by delegating mini projects that lead to bigger ones.


7. Lead with gratitude.

As the business owner, you have to remember that you’re a supportive role model. Your coworkers are the heroes. So say thank you. Give credit. Acknowledge the awesome work they’ve done. Remember, people who feel appreciated will always do more than what is asked of them.


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