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Karen Condor of Expert Insurance Reviews: 5 Things You Need To Know To Successfully Manage a Team

Maintain good self-care. As they say for caregivers, if you don’t take care of yourself, you can’t take care of others. The same holds true for managers. If you’re taxed mentally or physically, you can’t manage your team well due to the multiple forms in which stress can manifest, from irritability to work absences.

As a part of our series about the five things you need to successfully manage a large team, I had the pleasure of interviewing Karen Condor.

Karen Condor is an HR expert and team lead who currently works for the insurance comparison site, She manages over a dozen writers as part of an all-remote team with a 10-plus year track record of high performance in the competitive online insurance lead generation market.

Thank you so much for doing this with us! What is your “backstory”?

I grew up in a small town in northcentral Pennsylvania as the oldest of three siblings, where you could say I actually learned how to manage a team in pre-adolescence when my parents divorced and I supported my mother, who had to start working full-time, by taking care of my siblings as well as balancing her checkbook!

While I initially had career aspirations as a commercial artist, I found writing easier and more fulfilling, in part because it led to my high school and college newspaper advisors dubbing me a “natural leader” and promoting me to editor-in-chief positions.

And although I didn’t strive to be a leader, my hard work, curiosity, and problem-solving skills kept leading to management positions while working as a writer in the magazine, newsletter, technology, and even banking industries. I will also always be grateful that these management opportunities led to leaving Pennsylvania and experiencing life in California, then Massachusetts, and now South Carolina.

Can you share the most interesting story that happened to you since you started your career?

While I am more of a behind-the-scenes person — which is why I pursued print journalism instead of broadcast journalism in college — I must admit it was a treat to have my name in lights once!

It was on the marquee of Harpo Studios in Chicago in 1990, the day I met Oprah Winfrey and saw her spectacular white and gold office. At the time I was a TV critic for a magazine based in Pennsylvania and was part of a select group of critics invited to fly into Chicago for the day, tour the studios, chat with her on the set of The Oprah Winfrey Show, and meet and interview the cast of Brewster Place. It was a long, whirlwind day, but it was very exciting!

Since Oprah has become one of the most successful women in the U.S. — not to mention one of the richest — to this day I love to see the reaction people have when I tell them my Oprah story!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One of the mistakes I made when I was first starting, which wasn’t funny to me at the time but was very funny to my previous manager, was learning the lesson of never boasting you could do your boss’ job better.

When I was second-in-command at a weekly magazine on the East Coast, I consistently did an inordinate amount of work while my boss took advantage of his close relationship with top management and flaunted his ability to be lackadaisical. Many team members felt I should have his role and I agreed, especially since it included coordinating with our West Coast counterparts, in which I had a great relationship with a talented and prolific writer that my boss had difficulty working with.

Then the top management on the West Coast transferred to the East Coast and reorganized. They put me in the top spot. And they demoted my boss to another department, thinking he would resign, but he didn’t. He ended up sitting directly across from me in our “cubicle farm.” He heard every call I had with that talented West Coast writer, who suddenly became difficult with me when my dynamic with him changed from peer to boss. Every time I ended a call and sighed in frustration, my former boss would chuckle and tease, “So, it’s not as easy as you thought it would be, is it?”

Ok, let’s jump to the core of our interview. Most times when people quit their jobs they actually “quit their managers”. What are your thoughts on the best way to retain great talent today?

The top elements I have found that retain great talent, outside of competitive compensation, are leading by example and proving to employees that you respect them by showing interest in them, encouraging and listening to their feedback, acknowledging their accomplishments, and not micromanaging them.

How do you synchronize large teams to effectively work together?

Be organized, clear, and concise. This means finding an appropriate and user-friendly communication platform and not over-communicating. This also means having the resources your team members need be easily accessible to them.

At our all-remote company of 125-plus team members from around the globe, we have found that Slack is a very effective communication tool. Our top management has also provided a large number of guides and videos that team members can access at any time to help answer questions or clarify tasks, reducing the incidence of having to pause work while awaiting a reply from a manager.

Here is the main question of our discussion. Based on your personal experience, what are the “5 Things You Need To Know To Successfully Manage a Team”. (Please share a story or example for each, Ideally an example from your experience)

#1 Get thorough direction from above. Find out expectations from your own manager regarding tasks and timelines in order to know what your team needs to accomplish so you can formulate an effective action plan.

#2 Maintain good self-care. As they say for caregivers, if you don’t take care of yourself, you can’t take care of others. The same holds true for managers. If you’re taxed mentally or physically, you can’t manage your team well due to the multiple forms in which stress can manifest, from irritability to work absences.

#3 — Know your team. Determine each team member’s strengths and weaknesses to pair them with tasks they will take care of most effectively. It’s also helpful to know what learning style works best for each team member so you can communicate with them effectively.

#4 Embrace delegation. Provide team members with the information, tools, and resources they need to complete their tasks, then trust them to do their work. Instead of micromanaging, communicate you’re available for clarifications, problems, and feedback.

#5 Stay professional. Do not play favorites with your team members and do not befriend them. You are their manager, not their pal. This will help you be fair and firm.

What advice would you give to other CEOs or founders to help their employees to thrive?

Encouraging two-way communication and following through on it is essential for helping employees to thrive. If you don’t actively listen to your team, you won’t foster motivation, dedication, or loyalty, and you’ll negatively impact innovation, creativity, and productivity.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

The golden rule of doing to others as you would have them to do you is certainly not new and certainly not unknown, but more and more it seems to be something that is not done. And that’s now hard for me to understand, as throughout my life I have found that indeed what goes around comes around.

Early in life and into my mid-30s, I had a decidedly negative and sarcastic point of view, and I couldn’t figure out why negative things kept happening to me and I felt like I couldn’t catch a break. Then I moved cross-country and luckily was surrounded by people who had a positive view of life. I adopted their point of view and found my karma changed for the better.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I love this quote from James Thurber: “It is better to know some of the questions than all of the answers.” It’s a great reminder to keep an open mind because you can always benefit from collaborating with others — especially when you think you have all the answers. Being a control freak actually stymies your growth and development, and it could have the same effect on your product and business.

I wish I had this quote my senior year in college when I virtually single-handedly took on the self-created task of producing the college’s first literary publication. While the bulk of the poetry and short-story submissions were provided by a number of students, my overinflated sense of ownership and ability translated to doing the magazine’s paste-up and design by myself in addition to some of the writing.

But when the magazine came out, the head of the graphic design department, directly next door to the student newspaper office, barreled into our office, magazine in hand, and ripped the design to shreds, shouting, “Why didn’t you ask us to collaborate with you? You could have definitely used the talents of my students!” I didn’t even think of doing that, since I assumed I had all the answers. And instead of being embarrassed, I could have showcased the talent of the graphic arts students and produced a much more appealing publication.

Thank you for these great insights!



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