— With Jay Kelley
I had the pleasure of interviewing Jay Kelley. Jay is a repeat entrepreneur who plays at the intersection of technology, media and wellbeing, and is currently CEO of Peak. Peak is a goal-based savings app that integrates elements of mindfulness, so that managing money can be less stressful, more intentional and a lot more fun.
Thank you so much for doing this with us! What is your “backstory”?
I have a non-linear career trajectory and bounced between a few different industries, but the common denominator has been my desire to help people thrive. After school, I spent some time teaching abroad, worked in the ad agency world, and then helped to get the Documentary Channel up and running. We had an incredible journey, and ended up selling to Participant Media. Shortly thereafter, the opportunity emerged to join and eventually lead a young technology company. That company, Spire Labs, has built a number of wellness-focused platforms, which has given me some amazing opportunities to see what motivates people, and what they need to live well.
Our most recent product, Peak, which has been spun out as a separate company, is an opportunity to bring our team’s insights from the world of wellness into a new field: personal financial management. We’re specifically focused on pairing money management with mindfulness, which has also had a big impact on my personal life.
What is the top challenge when managing global teams in different geographical locations? Can you give an example or story?
Traditionally, the most common answer to this question would be “communication.” And that is still probably true, but in a different way: With modern communications tech, it’s easy for team members to stay in touch with each other, from anywhere. We use Slack to stay in constant communication and various video-conferencing software to maintain face-to-face contact. However, although this allows for seamless cooperation on projects and tasks, the remaining obstacle is maintaining the team culture and morale, when people don’t directly interface with each other.
This is actually one of the major problems we’ve been seeking to solve, with a platform we have called Spire. With Spire, we offer a dedicated social network for people to connect with and encourage their coworkers, by sharing (and rewarding) personal accomplishments. If your company isn’t using Spire, you can still use the same principles: Find ways to help employees connect with each other on a personal level. When people feel invested in the lives of their coworkers, they tend to feel more connected to the organization, as a whole.
What advice would you give to other CEOs or founders to help their employees to thrive?
Look beyond work performance. Seek ways to empower people on a personal level. This is not only a way to improve our society and the lives of our teammates… but study after study have shown that happier, healthier people also tend to perform better. Investing more deeply in our employees lives is a way to both do well and do good.
Most times when people quit their jobs they actually “quit their managers.” What are your thoughts on retaining talent today?
This is a major challenge for most companies, and something many of our Spire clients ask about. Not to sound like a broken record… but it comes back to relationships in the workplace. In traditional, hierarchy-based work environments, the employee’s relationship with their manager has an outsized impact on their perception of the organization. The more you can help your team build healthy relationships among themselves, the more resilient they will be, against any single strained relationship.
That said, there’s also a lot you can do to train your managers. Consider ways to strengthen their abilities, not only in terms of expertise or even traditional leadership skills, but also in areas like emotional intelligence, which will help them to motivate and sustain their teams, even during difficult periods.
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)
These lessons stem directly from our company’s core values. I’ve spent a lot of time thinking about them, and come back to them regularly, as I make decisions and guide others on my team to operate without needing my direct supervision. Here is how I would apply them to management:
Find your passion because passion, coupled with skill, is a jet pack
People naturally follow others who are passionate. Leadership can be exhausting, and if you’re not pursuing something you’re naturally, authentically passionate about, you’ll be forced to manufacture motivation. Whether this is passion about your business or product, or even just an element of your work, identify something that truly excites you and use that to elevate others.
As I already mentioned, I discovered mindfulness practice several years ago through one of our partnerships with another wellness company. I’d been familiar with the ideas behind mindfulness for a long time, but I believe it was Chade Meng-Tan’s book Search Inside Yourself (which explains his experience with bringing mindfulness to Google) that exposed me to the scientifically-proven impact of these practices. From there, I jumped into a deeper exploration and began my own regular practice. This had a dramatic impact on my work and personal life, and naturally I encouraged my team to check it out. At the time, this didn’t have a direct bearing on our product or work, but it was a connection point several of us shared. This common ground helped us build stronger relationships and a shared vision which, in turn, helped lead us to our latest product!
Practice compassion every day with your customers and teammates
As a leader, there are so many different things you must be doing and thinking about at the same time that staying in tune with the perspectives or emotions of your team members can be the last thing on your mind. But as humans, we all need to know that our experience is being considered. That old saying, “People don’t care how much you know, until they know how much you care,” is especially true for leaders.
To force myself to do this, I’ve actually started scheduling regular 1:1s with as many people as possible throughout the company. I call these “Joe with Jay” (coffee is not always involved, but that’s the idea), and it’s amazing how much I’ve learned from these conversations. It’s a never-ending process, to constantly learn more about where people are coming from.
Beyond your own team, staying in touch with your customers will help you to stay grounded. You’ll be able to guide your team more effectively, when you better understand the needs you are serving. Interacting with customers on a regular basis will prevent you from getting too caught up in your own perspective.
Improvise collaboratively like a jazz band
In a growth-stage company, it can be a particular challenge to find the appropriate level of communication and coordination because your needs are changing so fast. But companies of all stages face this challenge to some degree: Do we take a lot of time to get everyone strategically coordinated, but slow things down in the process? Or do we speed everything up but risk people running off in different directions? This challenge also presents itself in the possible tradeoff between speed to market and quality of product.
As a way to manage this challenge, I look to jazz: Everyone needs to learn the standards, so that there is a common reference point. But from there, the team realizes that there will be a lot of improvisation as we go along. As a manager, this shifts your focus and responsibility from overseeing every single element to providing the foundational training, to make sure everyone is equipped to play together and knows and agrees on the basic parameters.
Simplify the complex because simplicity is a form of magic
This particularly relates to communication. You have to always remember that there will be things lost in translation… even if everyone is speaking the same language. You have an idea, and you put that into words. And then your team either reads or listens to those words. By the time your ideas have gone through all of those filters, a lot will be lost. So, try to keep things simple. If you can reduce things down to the core elements, and convey them as succinctly as possible, you reduce the likelihood of miscommunication. You can also reiterate these ideas, without people feeling overwhelmed.
Take care of yourself mentally, emotionally and physically, so you can take care of others
This may feel like an outlier, in a list of management tips, but it is impossible to be an effective leader and care for others, if you are not caring for yourself. This is harder than it sounds. Like a lot of people in leadership positions, I hold myself to a very high standard, and try to lead by example. I expect a lot from everyone who works for me, so it’s important that they know that I’m putting in the work, myself. But if this gets to the point where my workload jeopardizes my health (physical, relational, mental), then everyone suffers. I can’t operate at my peak performance, if I’m sick or malnourished or chronically sleep-deprived. I can’t weather the storms of my professional life, if my personal life is under too much strain.
This is true for everyone, but is particularly important for managers because, in addition to considering your own performance, you have to consider the example that you set for others. If you refuse to take the requisite time to stay healthy, your employees will be inclined to follow your example.
To tackle this challenge this, I’ve tried to turn my high-performance mentality toward my own health: I’ve had to become relentless in maintaining healthy routines. For me, that looks like getting up early to do breathing exercises, spending weekends running trails, and aggressively “biohacking” my diet, to improve my overall energy level. That’s what has worked for me… but I would encourage anyone reading this, to start back with #1: Leverage your passions to motivate you to stay healthy, even when work gets crazy.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Someone recently shared the following quote from the stoic philosopher, Epictetus, which really resonated with me:
“The chief task in life is simply this: to identify and separate matters so that I can say clearly to myself which are externals not under my control, and which have to do with the choices I actually control. Where then do I look for good and evil? Not to uncontrollable externals, but within myself to the choices that are my own . . .”
This is a liberating perspective. Coupled with mindfulness, it allows you to focus your thoughts and energies on what really matters. I lead a growth-stage technology company. I’m married and have two boys. Every day brings a ton of change — both good and bad — sometimes in the extremes. So cultivating this kind of perspective on life is essential for me… and could probably benefit just about anyone.
Originally published at medium.com