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Dre Baldwin of Work: “Business Transparency”

Business Transparency. Make sure your team knows what is going on with your business, the aims of your business, and the purpose behind your actions. The better they understand what you are doing and why you are doing it, the better they will be able to use their own brains and intuit what needs to […]

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Business Transparency. Make sure your team knows what is going on with your business, the aims of your business, and the purpose behind your actions. The better they understand what you are doing and why you are doing it, the better they will be able to use their own brains and intuit what needs to be done, instead of always coming to you every time there is a challenge, need, or question. Empower your team.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Dre Baldwin.

In just 5 years, Dre Baldwin went from his high school team’s bench to a 9-year professional basketball career. At the same time, Dre built a content publishing empire.

Blogging since 2005 and publishing videos to YouTube starting in 2006, Dre has published over 7,000 videos with his content being viewed over 73 million times. Dre’s daily Work On Your Game Podcast has over 3 million listeners.

Dre has given 4 TED Talks and authored 27 books.

Free Book (just cover shipping): http://MirrorOfMotivation.com


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I really appreciate you having me here!

My background is as a professional athlete; I played professional basketball overseas for 9 years while traveling through 8 countries. I started publishing content to the internet back in 2005, long before it was cool. When the opportunity presented itself for creators to make money from their content, which was around 2008–2010, I already had an established brand name and an audience. I wrote my first book in 2010, and became a full-time CEO in 2015, when I stopped playing professional basketball.

Today, as head of Work On Your Game Incorporated, I teach how the mental tools required to reach the top 1% of sports translate to business and to everyday life.

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

The most interesting thing that happened was when I appeared on someone’s podcast and their assistant — a remote worker — handled most of the communication between me and the show’s host.

The assistant mentioned that he was a remote worker, and I started asking questions. I was intrigued because this remote assistant was fluent in English, had great conversational skills through email, and was really on-point as far as doing the work. He told me how he had been working for the show’s host for several years and had gotten really good at the job because of the time investment the host had made in him.

This sold me on the idea that I, too, could hire remote workers and have a very strong team while doing so.

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?

I don’t know if I would call it funny, but the worst mistake I made was hiring workers on the cheap because I was more concerned with saving money than I was with hiring the best people and getting the job done efficiently!

What I’ve learned over time is that better workers usually command a higher salary or rate for a job. This does not necessarily mean that the highest price person is the best, but it does mean that, as an employer, I should be willing to invest in the production and results that I’m expecting.

What advice would you give to other business leaders to help their employees to thrive and avoid burnout?

Stay in your zone of genius, and do the things that you’re best at.

If you find yourself handling jobs that just aren’t for you, have the confidence to speak up and find ways to get that job off of your hands.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

I’ve been hiring remotely since 2015.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

  1. Consistency of communication. For many of us, it’s out of sight, out of mind. When we don’t see a person in front of us, we often do not think consciously about communicating with them, nor do we make sure that they are doing the job that we want them to do. The biggest problem with this is that our remote workers do not clearly understand what is expected of them, nor do they have an open door through which to communicate their challenges, questions, or needs. This hurts everyone on the team. I have made the mistake of not communicating clearly or consistently enough with remote workers, thus us losing each other’s trust, and the work not being done properly.
  2. Understanding cultural differences. It’s important when hiring remote workers to understand the customs and cultural norms of the place they are from; not everyone is like you. Certain cultures are used to certain styles of communication, and ways of being given feedback. Certain people are better suited for certain jobs, based on their background and cultural upbringing. It is our job as employers to understand this aspect. Fortunately for me, I got smarter and started to read up on certain cultures when I was considering hiring people from that culture, so I knew what to expect ahead of time.
  3. Clarity of communication. This one is much more on the employer than it is the remote workers; many employers simply suck at communicating! They are not good at making clear exactly what they want, nor are they good at articulating when things are not being done the way that they want them to be done. I find that many employers unconsciously omit details that would really help clarify jobs for their staff.
  4. Setting expectations. In hiring remote workers, I am always asked — if I haven’t said so first — what my expectations are for my remote workers. They want to know exactly what is expected of them, and how their work and productivity will be measured. Therefore, as an employer, it is our job to make sure we articulate that clearly from the beginning, and we maintain accountability for these expectations.
  5. Keeping the energy up. It is much harder to communicate energy with someone who is remote — even through a video conference — than it is in person. We all know that the majority of communication is not verbal. When we are dealing with someone virtually, we lose most of that nonverbal communication. So, it is our job to supply that additional energy through our remote communication.

Based on your experience, what can one do to address or redress each of those challenges?

  1. Consistently communicate with your staff. Have a schedule, and stick to it. Your remote workers should know exactly when they will hear from you, and what to expect from you.
  2. Do research on the area from which you will be hiring people, and understand how they are used to communicating, working, and being given feedback. This is your job to do upfront.
  3. Sharpen your communication skills. The more clearly you can articulate and explain what you want, the more easily your remote workers will be able to do what you ask of them. If they are failing at the job, assuming that you did a good job of hiring, it is probably because your communication is not clear.
  4. Be clear and unambiguous about what you expect from your staff. This will help you and help your workers at the same time because everyone will be on the same page.
  5. As the leader, it is your job to supply the energy for everyone else on the team. The team will be following your lead; if your energy is down, their energy will be down as well. Remember that you are the tone-setter in the group.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

  1. Get on a video call. In-person and face-to-face would be best, assuming that that is not available, the next best thing is to get on a video call so you can at least see each other and communicate through your Expressions, tone, and body language on the call.
  2. If it’s a technical/tangible topic, make a screen recording. For any technical/online tasks, I always do a screen recording where I can not only show what I want to be done but also explain it at the same time.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

  1. Write your emails the same way that you would speak to that person! This goes back to the communication skills that I mentioned earlier, that many employers latch. When I write my emails, I write them the same way that I would speak, but many people do not have the skill. That does not mean they cannot acquire it soon because it would just take a little bit of time, and conscious effort.
  2. Use emojis. I was not always a fan of using emoji, but I learned that emoji can inject emotion into text that otherwise would get lost in translation. So, when you are making a joke, the Emoji can help communicate what text by itself would not get across to your reader.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

The biggest challenge is losing contact. The great thing about the world we live in today, however, is that we have the internet, computers, smartphones, and the ability to connect virtually from anywhere. And, since it can all be done from “home,” we can connect with each other minus the friction of gathering in person.

Another obstacle is anyone who’s not so comfortable or skilled at video conferencing, but I think we have all gotten our “10,000 Hours” at this over the last year or so (or are close to it).

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

  1. Constant contact! Schedule for when you connect and communicate with each other, and stick to it — the same way you would if you were all working in the same office.
  2. Business Transparency. Make sure your team knows what is going on with your business, the aims of your business, and the purpose behind your actions. The better they understand what you are doing and why you are doing it, the better they will be able to use their own brains and intuit what needs to be done, instead of always coming to you every time there is a challenge, need, or question. Empower your team.

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. 🙂

To get more people interested and involved in personal development.

I define personal development as any material, experience, or person that helps a person grow and advance. As humans, after we get through puberty, all growth must be intentional and on-purpose!

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

“Work On Your Game!!” — Dre Baldwin

It’s relevant because it not only encompasses my entire journey in both sports and business — but also because this phrase has allowed me to connect with millions of people all around the world, from young to old, sports to business.

Thank you for these great insights!

Thank you for having me!! I appreciate the opportunity.

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