After 12+ years of building companies, raising over $25 million, and experiencing both big wins and tough failures, Tyler Maloney is no stranger to the importance of humility in leadership.
Tyler Maloney, founder and CEO of TeachMe.To – a fast-growing platform connecting students with skilled private coaches to master new skills in sports, music, and the arts – like many ambitious entrepreneurs, has experienced many hard-won lessons of humility in leadership.
In this episode, Senior Executive Coach Connor Drake is joined by Tyler, to discuss the importance of embracing humility in leadership, company culture, and pragmatic strategies to motivate a high-performing team of A+ players.
If you’re a leader struggling with self-doubt and delegation while managing a growing team, this article will help you lead with confidence – without feeling like you need to have all the answers.
How To Be a Human-First Leader
Connor: What does it mean to you to be a Human First Leader in today’s world?
Tyler: I think the phrase can mean so many different things. I think to me the starting point has to be coming from a position of humility.
You have to start with the belief that teams are much greater than the sum of the individual parts. Which I think for entrepreneurs sometimes can be a difficult place to start.
You come in and part of why you jump into this is because you’re a little crazy and confident that you can go build the next big thing. You learn very quickly that you have strengths, you have weaknesses.
When you can assemble a team of really talented people that complement each other, you can do great things together. But that requires being humble about your own weaknesses and aware of them.
How Important is Humility in Leadership?
Connor: You shared a little anecdote about a team member who you realized was better at something than you and that being difficult to come to terms with sometimes.
What do you do personally when you feel those emotions bubbling up?
Tyler: Yeah, I think anybody that’s built a team gets to that point. The initial monkey brain reaction is insecurity.
You’re like, “Man, I hired this person, they’re saying we should do thing A. I’m thinking thing B. They explained it. They’re right. I’m wrong. And that keeps happening.”
“Oh, shoot. Like this guy or this woman knows how to do this thing better than I do.”
I have an advisor, Graham Weaver, who I talked to about this at some point. He’s like, “That’s the point. You’re not hiring well if you’re the best at everything.”
“You need to hire people who are better than you at the thing you hire them to do. That’s why you hired them.”
The Importance of a Cultural Fit When Hiring
Connor: It seems like you naturally gravitate toward that human-first “build a team and empower them” mindset.
As you build that team and you get disparate people with different skills and backgrounds all coming together, how do you get them to work together toward a common goal?
Tyler: I think part of it’s about hiring – it’s about bringing the right people together. Part of it is about motivating. Part of it’s about vision and having clarity about where you’re going.
From a hiring perspective, we look for two things:
- I look for energy makers, not energy takers, and
- I look for people that are, we-ambitious, not me-ambitious
I think that’s the qualities that it takes to get the right people in the room.
Then you have to figure out how to motivate … get the absolute best out of those people. Which generally is a combination of “Care Personally, Challenge Directly” is one of my favorite sayings.
It’s not coddling. It’s really pushing people and saying, “Hey, I think you can do better.”
It’s constantly taking people and challenging them to bring out their best.
How to Motivate a Team: The “Care Personally, Challenge Directly” Approach
Connor: How do you build that kind of culture in an organization? What are some of the steps that you do on a very practical day-to-day level?
Tyler: This is a framework that I’m absolutely borrowing. It’s from a book called Radical Candor. It’s a phenomenal book on leadership and managing people.
I think if you think about that quadrant – she goes through “Care Personally,” “Don’t Care Personally,” “Challenge Directly,” “Don’t Challenge People.”
What does it say if you’re in each of those buckets?
If you don’t care and you don’t challenge your checked out, right? You don’t really care about the success of the organization. You’re apathetic.
If you don’t care personally and you challenge a ton, you’re kind of a jerk.
If you don’t care about the individual, you’re a jerk. No one wants to work for a jerk.
If you care personally, but you don’t challenge directly, you’re actually demonstrating to the person you don’t trust them.
When I care personally and I challenge directly, we have enough of a relationship and trust that I can say, “Hey Connor, I think last week you didn’t give us your best, and I love you and I think you’re capable of a ton of things. So I’m going to hold you to giving us your best every single week.”
That’s really where the best work occurs. That’s where the best relationships occur. And that only works if there is trust and there’s courage and bravery on both sides of that relationship.
How To Build Trust Within a Team
Connor: Do you tend to jump straight into that from day one? Or do you have kind of a slow build-up process when someone is new to the organization and that trust isn’t built and proven yet? Are there any steps you take to build it up?
Tyler: I want them to understand what we’re about before they decide if they want to join or not.
I will go through and take 30 minutes and go step by step and say, these are what they are. This is how we live them out. This is why they are the way they are, and they’re not like rainbows and sunshine.
These are the core beliefs we have in the way that we operate and build a business – and you’re going to either be attracted to them or repelled by them.
If you’re repelled by them, great. We just saved you and me a bunch of pain and time.
What it does is it makes onboarding much faster.
People typically enter slowly and they observe, and that is an impediment to progress in a startup.
You can’t have your new hires come in and take six months to try to slowly understand what’s rewarded and not and then start making an impact on month seven.
They got to make an impact on day one.
I can say to new employees as they come in, “This is what’s rewarded. I don’t know what your last organization was like. Toe stepping here is rewarded. We want you to step on people’s toes.”
So like in week one, when you do the review, you’d be like, “Hey, you stuck your neck out … and I actually really liked that. Thank you for doing that.”
It’s communicating upfront what the expectations for the culture and the organization are.
That’s how you get someone to enter into the group and be effective in two weeks rather than in six months.
How to Create Transparency in the Workplace Through Honest Feedback
Connor: Let’s talk a little bit about transparency. A lot of people talk about being transparent as an organization, but what does that actually mean for you?
Tyler: I think we operate at the 95th percentile of transparency. We share every single Friday, we have a retro.
We go through: What’s the bank balance, what’s the runway that we have, what are the KPIs, how are we doing against those KPIs? Each department, what they are: green, yellow, red. Are we hitting those?
And then every month we give a scorecard publicly to the entire company. Here’s marketing on a scale of one to 10. Here’s how they did this this month. Here’s product on a scale of one to 10.
Sometimes it’s a nine and we’re celebrating them, and sometimes it’s a four or six.
People understand when they’re performing well and when they’re not, they know where they stand. That’s a really important thing.
We are very open with transparency around company and team performance. I think that creates an environment of trust.
We give a lot of feedback. I’m giving you critical feedback because I want the best out of you.
In a culture where feedback is a gift, it works really well with people that can receive that feedback.
In a culture of people who are defensive or insecure, it doesn’t work super well. So we try to select the right people that match with that culture.
Humility in Leadership: How Do Leaders Learn From Their Mistakes?
Connor: Are these lessons you’ve learned along the way, or is this who you’ve always naturally been?
Tyler: No, totally learned them and mostly through trial and error.
I started my first company when I was 22. It failed after raising 12 million in a very exciting journey with big ups and big downs.
The world has a way of teaching you lessons.
When you approach building a company with a belief – that is a wrong belief – that belief will get beat out of you one way or another.
If you approach building a company thinking culture doesn’t matter, I promise you in five years, you will know that culture matters.
It’s through a lot of trial and error. Over time I’ve evolved my philosophy.
I’m sure in 10 years, I’ll look back at this conversation and say, “Oh, I really like 70% of what I said, but 30% like, man, I’ve learned that doesn’t work or it doesn’t work in this scenario.”
These things you develop over time through experiences, through learning.
I’m now 12 years into building companies. I’d like to think I’ve gotten somewhat better at them over that time. It’s definitely not something that’s innate, but you do have to be open to learning.
Sometimes you got to cut bait and be like, “Wow, my approach is totally wrong. I need to let go of this belief. It’s not serving me anymore.” And then adopt a new belief.
Those are the difficult judgments that you have to make every single day building a company.
Tyler Maloney’s Advice for His Younger Self
Connor: You’ve shared so much over the course of this conversation. If you could give your say 21 – 22-year-old self just starting their first company, one piece of advice. Does anything come to mind?
Tyler: The first words that immediately pop in mind are just keep going.
First company was my everything. It was my entire personality. Made lots of mistakes, ego got really big, I thought I was the greatest thing since sliced bread.
And then when that doesn’t work out, it’s incredibly deflating. And you want to quit and you never want to do it again.
For first-time entrepreneurs, the failure rate is incredibly high, like 90 plus, it depends on what you count as starting a company, but either 90 plus percent or 99 plus percent.
So if you play it as a one-off and you think it’s a get-rich-quick thing, you’re going to be disappointed.
But if you play it like an iterative game that requires a lot of personal growth, and you stick with it through the ups and the downs I think most people end up being really glad that they took that route.
I certainly am at this point in time.
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