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Courtesy of The Oracles

It can be difficult to maintain friendships at work when you get promoted — especially if you’re managing your friends. How do you straddle the line between being a good friend and a good boss? We asked these seasoned business leaders and Advisors in The Oracles for their advice.

1. Be honest.

Bethenny Frankel, courtesy of The Oracles

While you can make new friends at work, your best friends are often from childhood. To gain respect as a boss and a friend, be loyal and direct. I have no time for nonsense and I don’t play favorites. I have favorites because they’re the best. Every kid doesn’t deserve a ribbon. That’s not life. Be kind, but it’s not group therapy.

Sometimes you have to give feedback to someone you care about personally. Help them finesse their ideas and give them color. Most ideas aren’t terrible, but many people aren’t able to execute on them. I’m not an expert on all ideas, but I can tell when someone is all talk and no action. At the end of the day, remember it’s called “show business,” not “show friends.” Bethenny Frankel, entrepreneur and philanthropist; founder of the Skinnygirl lifestyle brand and the charity BStrong, New York Times bestselling author, and Shark on “Shark Tank”; follow Bethenny on Twitter and Instagram

2. Don’t let your ego increase with your rank.

Jocko Willink, courtesy of The Oracles

My ego didn’t increase with rank as I got promoted in the SEAL Teams and began managing my friends. I still treated everyone with respect, asked others for their opinions, and didn’t act like I was better than anyone.

Leadership requires a balance between being a boss and a friend. If you’re too close, it’s difficult to have hard conversations. You might avoid giving someone the feedback they need to improve, or not have the awareness to fire someone for the good of the company. But if you’re too detached, you may be too quick to fire people to save a buck or overwork your team, thereby developing a reputation of not caring.

Slowly open the door to friendship and test individuals’ ability to handle the relationship. If they become unprofessional, back off and detach. If you open up too quickly and they can’t handle it, you have to end the friendship, which can damage your professional relationship. Jocko Willink, retired U.S. Navy SEAL officer, No. 1 New York Times bestselling author, co-founder of Echelon Front, partner in Origin USA, and host of the top-rated “Jocko Podcast

3. Empower your team to do their job.

Judd Rosenblatt, courtesy of The Oracles

I struggled with this in my early days as a boss. My default was to give orders, expect results, and lay on the constructive criticism when needed, even though many of my employees were also my friends. Unsurprisingly, this created some tension. I later realized that my employees’ goals were the same as mine and that I should empower them to reach their full potential instead of dictating to them. Most people want to be good at their jobs, and if you’re hiring top talent, they probably know how to do their jobs better than you do.

I believe that being a friend and a boss can be an asset. Every week, I check in with all 25 employees one-on-one to create an open line of communication about their work and anything else in their lives they want to share. By respecting everyone as a person, I can pre-empt problems before they happen, give my team the tools and motivation they need to do well, and even receive a bit of honest criticism myself. —Judd Rosenblatt, founder and CEO of AE Studio, an Agile web development and data science company dedicated to increasing human agency; connect with Judd on LinkedIn

4. Stay detached and professional at work.

Bryce Welker, courtesy of The Oracles

Whether you become friends with your employees or you hire your friends, it’s not easy to be both someone’s friend and their boss. If you can honestly see yourself being great friends with every single person in your company, then by all means go for it. But you’re probably not going to be able to do this with everyone you work with, making it difficult to work alongside those you’re already friends with as well as those you aren’t.

To avoid playing favorites, maintain the same level of detached professionalism with everyone when you’re on the clock. There’s nothing wrong with showing camaraderie outside of work hours by getting together socially in your free time. However, don’t organize these events in association with your work, and don’t treat the people you see after hours like pals at the office. —Bryce Welker, CEO of online education company Crush Empire and founder of Crush The CPA Exam; connect with Bryce on LinkedIn

5. Make all your decisions with integrity.

Peter Hernandez, courtesy of The Oracles

Finding that balance is really difficult, but it’s possible if you make all your decisions ethically and with integrity. Before any conflicts arise, explain to your friend that your job is to do what’s right for the company. For example, if he or she applies for an internal position but there’s a better candidate, choosing your friend is not what’s best for the business. If your judgment is cloudy in the face of a tough decision like that, journal on it, pray about it, or talk it through with someone you trust.

If you’re being a good boss, you’re also being a good friend. For example, if your friend does something that isn’t in the company’s best interest, you aren’t being a friend by condoning it. That gets into the definition of friendship: Are friends here to enable us or help us grow? Peter Hernandez, president of the Western Region at Douglas Elliman; founder and president of Teles Properties

6. Care personally and challenge directly.

Tom Shieh, courtesy of The Oracles

Kim Scott’s book “Radical Candor: How to Get What You Want by Saying What You Mean” talks about caring personally and challenging directly. That’s what it takes to straddle the line between being a boss and maintaining friendships. Speak the truth in love; otherwise you risk being too timid to lead effectively or overly harsh and impersonally critical.

Business isn’t just business; it’s extremely personal. It’s not enough to focus only on someone’s ability to perform. A strong leader develops genuine relationships with their team, cares about them as individuals, and takes time to understand their perspective. They also say what needs to be said. When you’re willing to deliver hard feedback, address the elephant in the room, and make tough calls, you gain the respect of your team. As iron sharpens iron, so one person sharpens another. Tom Shieh, CEO of Crimcheck, advisory board member to Defy Ventures, and advisor to Tiny Devotions; connect with Tom on Facebook

7. Ensure your team’s goals are aligned with your own.

Brandon Dawson, courtesy of The Oracles

If I have to treat you like I’m a “boss,” we aren’t going to find success working together, even if we’re friends. The role of a leader and friend is to positively impact those you’re committed to. People want to work with leaders who are interested in their success. You spend more time with your team than your family, so you want to know they have your back and vice versa.

To be a good boss and friend, ensure your team’s personal, professional, and financial goals are aligned with yours and your business’s. If they know you’re fighting for their goals, they will work hard to make yours a priority. Then if you have to be hard on them, they know it’s because you want them to succeed, so they’re receptive to your feedback. When you work side by side, they will also trust and follow you. Creating confidence this way means that when you’re losing, you fight together, and when you win, you celebrate together. Brandon Dawson, serial entrepreneur and co-founder and CEO of Cardone Ventures; founder and CEO of Audigy; host of “The B Dawson Show” podcast; connect with Brandon on Facebook, Instagram, and LinkedIn

8. Be a leader, not a boss.

Patch Baker, courtesy of The Oracles

My former commander in the Marines, Major General James Mattis, never spoke of his rank. We followed him because he was a leader, not because of the rank on his collar. We believed in the mission and his ability to lead us to complete it.

Stop being a boss and be a leader. Just like the quarterback is not the boss of the linemen or running backs, I’m not the boss of my team. I don’t have employees — I have teammates. You’re working together to get to the same end zone. The second you become a boss is the second you stifle your business growth. Instead, hire the right people and give them the authority, knowledge, and guidelines to be successful on the team. Do that and you’ll be surprised at the initiative they’ll show to grow your business for you. Patch Baker, founder and CEO of Mobius Media Solutions; former U.S. Marine, with a mission to help people leave the military today and not feel abandoned tomorrow


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