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Five Thriving Leadership Lessons

As Thrive Global’s COO and CFO, I have some advice about how to create a compassionately direct workplace and a culture where employees can thrive.


By Brent Chudoba, COO & CFO @ Thrive Global
Standing out from the crowd concept with arrows on blackboard

Standing out from the crowd concept with arrows on blackboard
The Entry Interview and Compassionate Directness

When Thrive Global launched in 2016, one of the first features the company embraced was called the Entry Interview. It’s simple: We ask everyone what is important to them in their lives, both at work and outside of work. For parents it might be taking their child to school or daycare in the morning. For others, it might be leaving early on Tuesdays for a violin class. We know clear communication and clear expectations from both sides from Day One are directly connected to our ability to set priorities and perform at our best. And we use regular check-ins to keep this conversation going as our needs evolve over time. As leaders, we have a responsibility to create a culture where our employees feel comfortable escalating problems that may be buried, and then teach people how to elevate those issues.

Not long after I started at Thrive Global, an executive assistant joined our team, supporting me primarily, but also several other company leaders. When I sat down with her to do a 30-day check in, we had a great conversation, but I learned that since joining our organization she had rarely been able to do something that was very important to her, and which hadn’t come up in her Entry Interview, which was running and exercising.

Even though this wasn’t at all technically related to her work at Thrive, it really struck me as an important learning on two fronts, which were actually directly connected to her experience with the company and her ability to both be fulfilled and perform at her best.

1) For a company whose mission is to combat the stress and burnout epidemic and take a whole human approach, it was critical for us to start with ourselves, making sure everyone at Thrive had every opportunity to take care of their physical, mental, emotional, and spiritual well-being.

2) This was the perfect illustration of one of our cultural values, Compassionate Directness. At Thrive, it’s paramount that we are empowered to speak up, give feedback, disagree, and surface problems and constructive criticism immediately. When we share feedback and new ideas, as well as tension points, with compassion, empathy, and understanding, the whole company benefits. That’s how we course-correct and grow as individuals, and that’s also how many of our best ideas come to light.

So, Compassionate Directness has lots of applications — from raising mission-critical red flags, to speaking up when you’re feeling burned out and overwhelmed — and in this case, my executive assistant found a way to speak up and let me know that she wasn’t getting something in her life that she needed. There’s no way I would have known otherwise. So we caught it early, and agreed there were really easy ways to figure out a way for her to handle all her responsibilities and still make time to run and exercise.

We dug deeper and found that since she was supporting several executives, she felt it was important for her to be in the office until each one of them left for the day, every day. And we have varying schedules: One might leave at 5, another at 6, another at 7, whatever the case may be day to day. But no matter what, she was the lowest common denominator, and this meant that she ended up sacrificing something that really meant a lot to her and helped her thrive. When I shared this with the other executives, it opened up the lines of communication, and we worked out a way that worked for everyone. We asked her to create a Slack channel including all the key folks she supported – and in the morning she’d let the group know when she planned to leave each day so everyone could adjust accordingly, and as long as everyone was aware, no problem.

Secure Your Own Mask First

Work, family, travel, personal interests, being always connected to our devices — this can easily lead to high stress and the feeling of being always on and running around, falling behind, and living in a world of constant catch-up.

We’ve all felt this pressure. And I can say, with a job where I travel weekly and have two little ones at home, it’s not easy at all. And a lot of us fall into the trap of putting ourselves at the bottom of our own to-do list. We know we should be eating well, getting enough sleep, taking time to do the things that matter most to us — but instead we do the opposite. We rationalize, saying “I’m too busy and important” (or whatever it may be), so it’s fine that I’m eating garbage, skimping on sleep, and never taking a moment for myself. But this is exactly the delusion that Thrive is fighting: the delusion that we must burn out in order to succeed.

But how can your team and your family and anyone else who is depending on you feel safe if you are living like this? If you’re running out of oxygen?

When you’re on an airplane you’re told to “secure your own mask first before helping others,” even your own child. After all, it’s not easy to help somebody else breathe easier if you’re fighting for air yourself.

That means getting enough sleep and exercise, eating well, and making time to connect with yourself and your own values and passions. I’ve learned that when you do, you’ll be much more present and much, much better able to give the best of yourself to others – whether your children, your employees, your friends – than if you’re burned out, sleep deprived, and depleted.

Once you realize this problem, you can find a solution that fits your life. When I can rise early and create that pocket of time where I can get centered, whether that is through a workout or meditation or just planning out my day and having a block of time to plan how I want to attack the day, it helps me stay on offense vs. waking up and playing defense and letting my inbox (and everyone else) dictate my agenda.

Hire Slow

Hiring someone, particularly for a leadership or management role, is one of the most important decisions you will make. And while you can face tremendous pressure from various directions – teams that feel overworked, and just the natural desire to be productive and pull the trigger — it’s crucial to take your time. This helps you minimize the risk of unknowns.

Remember, as much as you’re feeling the need for that perfect person to join your team asap, and as hard as it can be to wait — it’s nothing compared to the damage you can do by letting that urgency overwhelm your better judgment. Rushing into a hire can be one of the biggest setbacks for a company, taking a toll on productivity, morale, and even every aspect of the business. And it’s all the more painful because it’s self-inflicted. I’ve seen it happen; we’ve all seen it happen.

At Thrive, we’ve mapped out a hiring policy that makes sure every candidate meets key stakeholders. And one of our interviewing principles is to look for every reason to disqualify. We’re on the lookout for red flags, we check every reference. This can lead to a longer process, but it’s worth it every single time we as a team reach a consensus on the candidate we want and need.

Rule of Threes

Experienced leaders and leadership teams know the value of internal communication within a company, but sometimes this can be overlooked. My version of the Rule of Threes has, you guessed it: three core principles.

1) Three times: Anything you want to stick, you need to repeat at least three times.

Whether you are rolling out a new healthcare plan or launching a new marketing message, you need to repeat the messaging a lot for it to stick. Remember that with vacations, sick days and travel, there are 10-20% of people not in the office every day. So repeating messaging is critical. And in growth environments, new people are joining frequently and missing out on key messages.

2) Three channels: Ever get a text message from your significant other during a company all-hands and miss an update? Think of all the distractions that could cause someone to not have a message stick. Use three channels, Email, Slack, in-person or whatever tools your organization uses to meet people in different places to deliver any message that is important for your org to retain.

3) Keep it to three key messages. Whether it’s your PR pitch, your core value prop, orienting around a simple, crisp number of messages is always helpful – to remember and to deliver. Don’t be too rigid around it, but find frameworks that help you scale. The rule of threes has always helped me. (And yes, sorry, I realize I’ve broken my own rule by sharing five principles with you in this post.)

Learn from your mistakes. But even better, learn from other people’s mistakes.

Many of my best principles come from lessons learned from others. There’s a wealth of advice and wisdom out there, probably more than ever before in history. Podcasts, TED talks, books like Plan B by Sheryl Sandberg and Adam Grant. Thought leaders like Tim Ferriss who have built great followings because they extract lessons from top performers. Learn from their hard-won experience, steal their secrets. That’s what they’re there for. As Arianna Huffington says frequently, she learned the hard way about the importance of prioritizing herself when she collapsed from exhaustion and sleep

deprivation. She’s spoken about it, written about it, and built Thrive Global around it, so that others don’t have to learn the same lesson the hard way. So whether it’s spending time with a mentor in person or spending time with the work of those you admire, be sure to go after their lessons so you can benefit from their experience and avoid making the same mistakes they made.

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(Thrive Global)

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