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Dr. Tommy Weir of enaible: “

Managers need to be more deliberate in checking-in with their employees on top of checking-up on active deliverables — just as you would, or should, in an office environment. Ask each team member how they’re doing, feeling, and if they need any help. Do it in the same way as if you’d bump into them grabbing a […]

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Managers need to be more deliberate in checking-in with their employees on top of checking-up on active deliverables — just as you would, or should, in an office environment. Ask each team member how they’re doing, feeling, and if they need any help. Do it in the same way as if you’d bump into them grabbing a coffee or in the bullpen. Make it natural rather than schedule a daily check in, but do it daily. Not only will this help in maintaining a positive corporate culture, but it will also shed light on where your employees are struggling and where you need to step in to help.

Employees should also be encouraged to talk to one another. The void that’s being felt right now is the absence of the informal communication. As much as we don’t want to admit it, work is social. Employees build relationships; they share what’s going on in their lives. Just using formal communication channels sucks this right out of the system. Companies that succeed in building a great employee experience at this time will be the heroes in the recovery, which could last up to six quarters (if history proves true).


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Dr. Tommy Weir, a speaker, writer, and entrepreneur dedicated to helping enterprises achieve market-defying results through advanced leadership science.

Combining his 20 years’ experience in CEO coaching and cutting-edge leadership research with data science methodologies, Dr. Tommy Weir now focuses on applying AI to leadership as CEO and co-founder of enaible Inc., which brings AI-powered productivity to companies who are searching for a better way to make the invisible, visible and the hours worked, productive. Through enaible, Dr. Weir has built the world’s first Leadership AI Lab.

In addition to his work at enaible, Dr. Weir is a visiting scientist at MIT and prolific author. His books on leadership have earned numerous accolades, including #1 best-seller status on Amazon, First Finalist in the International Book Awards, and the #2 book in the Wall Street Journal’s Readers Poll.


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”?

My name is Dr. Tommy Weir and I’m the founder and CEO of enaible, a company that offers an artificial intelligence (AI) platform to help business leaders improve the productivity of their workforce.

I’m passionate about helping leaders become the best they can be and firmly believe that every employee deserves to be led by a great leader.

For the past two decades, I’ve worked closely with CEOs — coaching them and sharing perspectives on what makes great leaders — and discovering the power and role of data science in leadership. From these experiences, I’ve authored a handful of books which have earned numerous accolades, including #1 best-seller status on Amazon, and regularly present at industry and global events.

In October 2016, I travelled to Tokyo to learn more about applied AI and how companies like Media Lab, Sony Labs, and Google are doing innovative and progressive things with AI. This is when I had my “aha moment,” and led me to discover the relationship between AI and leadership. Deeply curious about this, I learned the basics of coding for machine learning to better understand how AI can significantly impact and enhance leadership…and I was hooked.

Two years later, in 2018, I hired a rock-star team of data scientists and opened the world’s first Leadership AI Lab. Combining 20 years’ experience in leadership research and coaching CEOs with AI, we set out solve the productivity paradox and created enaible: AI-powered leadership.

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

The inspiration behind founding enaible is one of my favorite stories. I spent the bulk of my career as a leadership coach to top executives. The biggest pain point for a former client was employee productivity. During one of our sessions, he simply asked what he could do to effectively drive efficiency across his organization and for his employees. Half-jokingly, I suggested he build a productivity engine, and incorporate AI to help automate data while he’s at it.

“I like it, you do it,” he said. Puzzled, I looked back at him with a blank, confused stare. He continued, “You’ll figure it out.”

From there, I rolled up my sleeves, hired a rock-star data science team and built what became enaible. While it originally intended to be a one-time project, seeing the marriage of data science and leadership science, I realized, this isn’t a project, it’s the future of leadership.

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?

In my very early years, I was working at Ralph Lauren in Palm Beach. The store manager challenged employees at the store to sell rare pieces of antique jewelry that had recently arrived as part of an art deco collection. Just before the store was about to open, I jumped on the phone and started to call Mr. Cohen. My coworkers asked, “What are you doing?” I said I’m going to sell it. They laughed in disbelief. They watched as I told Mr. Cohen that “we have the perfect gift for your wife for Christmas.”

Simultaneously, they gasped and laughed, thinking this was a long shot. Turns out timing was on my side, as Mr. Cohen responded, “today’ is my wife’s birthday and I still need to get her a gift, I’ll see you in an hour.” I sold him the necklace and made the single biggest sale in store history.

I learned my first, most important lesson of my young career: have courage, be bold and try to do something big. If you don’t try, you can’t achieve. Don’t let others lack of belief in themselves (or in you) hold you back. And laugh at yourself and recover fast when you say the wrong thing.

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

Executives, firstly, need to identify the causes of distress and possible avenues to burnout. According to a recent Harvard and NYU study, employees are working an average of 48 minutes longer each workday and attending 13% more meetings since transitioning to remote work. However, there is no data indicating these longer hours or meetings are actually productive. In a recent survey conducted by enaible, 76% of executives are concerned about having a false read on their employees productivity. When you see your employees working longer hours without noticing a positive change in quality or productivity, it’s a sure sign of burnout.

CEOs can help their employees avoid burnout by identifying areas where they can improve productivity and giving them the resources, tools, and encouragement they need to do so. If you can help be more productive during the time they are working, and as a result reduce the number of hours they work, everyone wins and burnout is much less of a problem. However, employers cannot help their workers if they do not have a clear insight into where they are struggling. Being able to identify specific pain points can give leaders the advantage of independently coaching each employee — and the business — to success.

Ultimately, it’s up to employees to energize themselves and drive their own engagement and motivation, but managers play an important role by putting them in the best position to succeed.

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’m 100% for people working anywhere at any time, actually everywhere, all the time. But personally, I much prefer face-to-face leading. The creative combustion, keeping the pace, speed, and getting to know each other so you can motivate all need depth of interaction. And that happens best face-to-face.

When it comes to the remote side, the key is not letting the environment dictate how you lead. Instead give the leadership that is needed no matter what the environment.

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. Maintaining employee engagement/morale: Engaging employees is hard enough in the office, but managers need to put in the effort when trying to keep a culture of collaboration and support virtually. Without company lunches, water-cooler talk, seasonal parties, even short office drop-ins, managers aren’t influenced to connect with their teams casually. Additionally, employees are struggling without the peer-to-peer interactions that such events allow.
  2. False reads on employee productivity: There has been an influx of recent studies evaluating how employee productivity has shifted since moving to a remote set-up. However, the majority of the data is based off the individual employee’s perception of their own change in efficiency. If employers do not have a system in place to accurately measure productivity, they are blind to any of the peaks or valleys in productivity.
  3. Out of sight, out of mind mentalities: We’re not passing each other in the hallway or lunchroom anymore. When you are not physically in front of someone, they tend not to cross your mind.
  4. Lack of interpersonal communication methods — from leaders to employees and from employee to employee: Zoom fatigue is very real right now. In the office, employees are able to exchange ideas and work gets done on the way in or out of a meeting, or passing someone in the hallway. You cannot do that with a Zoom call. Combine that missing link with the lack of true social connection a video call brings, and it hinders the pace employees can operate.
  5. Flexibility needs to sustain work-life balances from home: It’s not a 9–5 world anymore. Employees are dealing with a lot of demands during the day while at home and managers need to anticipate their teams to be filling in their hours in the early mornings or late evenings.

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

Managers need to be more deliberate in checking-in with their employees on top of checking-up on active deliverables — just as you would, or should, in an office environment. Ask each team member how they’re doing, feeling, and if they need any help. Do it in the same way as if you’d bump into them grabbing a coffee or in the bullpen. Make it natural rather than schedule a daily check in, but do it daily. Not only will this help in maintaining a positive corporate culture, but it will also shed light on where your employees are struggling and where you need to step in to help.

Employees should also be encouraged to talk to one another. The void that’s being felt right now is the absence of the informal communication. As much as we don’t want to admit it, work is social. Employees build relationships; they share what’s going on in their lives. Just using formal communication channels sucks this right out of the system. Companies that succeed in building a great employee experience at this time will be the heroes in the recovery, which could last up to six quarters (if history proves true).

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?

Firstly, make it as personal as it can be. This is where video calls are work in your favor. While you should be scheduling one-on-one calls with each employee already, use this opportunity to do so. If you are checking-in on a regular basis, nothing should come as a surprise to the employee. Secondly, think like a coach. The ultimate goal of a sports coach is to have each player work together and succeed. When you take the approach of guiding a team versus managing an employee, the conversation goes from what they are doing wrong to what they can do to improve their skill set. By operating hard discussions in this fashion, the conversation is a lot more constructive and a lot less critical.

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

Executives should avoid giving constructive feedback via email. When it can’t be avoided, using specific examples on what needs to be improved and examples of best practices to compare is helpful. Use friendly, casual language where appropriate and don’t leave anything up to false interpretations. Lastly, leave it open for them to ask any questions after-the-fact.

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?

Create space for water-cooler conversations — many of the best ideas and thoughts are generated spontaneously. They may happen over a quick coffee or when a random idea pops up between two people and they pull in a few others — then an epiphany adds millions to the top line.

For those in the tech world, Slack works super well for this. But not everyone else has been living in Slack. Pushing people into a new tool doesn’t feel natural. Try to recreate natural interaction space.

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?

As a leader, it’s vital that you make expectations clear and communicate them openly. Don’t assume people know what to do or how to do it. Guide them to the right path, or else risk your people diverging off course. Where you look, they will go, and right now, your team needs your direction more than ever. Be thoughtful when communicating. Approach every conversation with a strategic plan and balance of to-dos and how are yous.

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. 🙂

This may be too cliché: Machines learning, humans leading.

I’m obsessed with the idea that everyone deserves to be led by a great leader. But sadly, reality says it’s not happening. I’m convinced that humans and AI are better together. AI-empowered human leaders can help us prosper and make each of our futures better.

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

You Can if You Think You Can. In the 4th grade, my dad put a poster with this quote on my bedroom wall. A few decades later that exact poster (framed now) hangs on the wall in my study. I’m told that I lacked confidence at the time and my dad was trying to help boost mine. In turn, he shaped the way I think and live.

Thank you for these great insights!

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