Building Healthy Teams - Elevate Summit, Denver

In preparation for speaking at Elevate Summit in Denver, I prepared this script for my talk. I wasn’t able to memorize it fully, so wanted to share it in text since there were a few key points that may be easier to digest in this format. The video of the talk is embedded at the end. 👍


After working in corporate-land right out of college, an opportunity came up to join a hot new startup in San Francisco. I just bought an outrageously overpriced first home (thanks housing bubble) and was very excited for my massive startup payday. So we packed up the moving truck and headed to the Bay.

The first few months were very exciting. Our small team was a powerhouse and we were getting tons of interest and new customers. Fast forward a year and things … were different. We had raised a few rounds of capital and we had grown to fill our needs. But our team was no longer … a team.

Here’s an example of what I mean:

Our CEO had demanded a 9am start time from everyone, so each of us filed in on time. Those that were late made sure to stop by the CEO’s office (near the front door) to give him our excuse for our tardiness that day. We mumbled our “hello”’s to each other at the coffee pot. The person who arrived the latest that day could usually be found grumbling at the lack of coffee when they arrived.

We all worked in relative silence in our open office. Then – around 11:45am – came the day’s moment of truth. Your stomach would start to grumble, announcing that it was time to make a decision: do I really want to eat lunch with anyone in here? The answer, of course, was “no”. But you couldn’t just throw your coat on and head to the elevators. Someone would know what’s up. And the only thing worse than a group lunch was a one-on-one lunch with someone you didn’t like.

So, the trick was to not take your coat. Stand up. Stretch. Maybe add in a yawn. Then slowly walk towards the front of the office. If anyone stopped to ask you if you were headed to lunch, you quickly respond: “Me? No. Just headed to the bathroom.” If caught in this lie, make sure to hang a left towards the bathroom. Maybe stand in there for a minute to really sell it. Stare at yourself in the mirror and wonder how the hell you ended up working somewhere like this. Then slowly re-open the door and sneak down the hallway to the elevator. Head to some place along Market St where you know no one else will eat. Finish your lunch, then stare at your watch and watch the minutes tick by until it was time to return to your desk.

This was my life in San Francisco. It’s no wonder I left after only a year. But sadly, this is what happens when teams are not cultivated: when growth consumes the culture of a team and focus is not given to a team’s health. And sadly, this is an all too common experience.

According to a 2015 Gallup survey, only 32% of people say they are “engaged” at work. Aside from these toxic work environments being a drain on the individual, they have serious business impacts as well. Disengaged individuals tend to do the bare minimum at work. Low morale breeds low morale and it spreads across entire organizations. It costs the U.S. an estimated $450 billion to $550 billion per year of lost productivity, stolen goods, and missed days of work.

So if working somewhere like this sucks so bad, why aren’t we doing more? Why aren’t we actively engaged in building healthy teams instead?

Frankly, nobody taught us how.

Now, there are a litany of managerial and leadership books you can pick up. Each has their own unique perspective on this topic. Each one may help a different team in a different stage in its growth. But for the teams I’ve had the pleasure of leading, I’ve found 3 strategies most effective.

Clarify the Why

First, we’re going to clarify the “why.” Pat McMillan said: “A clear common compelling task that is important to the individual team members is the single biggest factor in team success.”

If you’ve ever worked on a crappy team, odds are that there was no “clear, common, or compelling task”. Was it “make a bunch of money”? Sell the most ads? For lots of people, business metrics are hard to get excited about. So what’s the goal here? What is your team doing that’s exciting or compelling?

But before you call for a team offsite to layout your corporate mission statement, your best bet is to start with some introspection. Find a quiet space and begin to really think through some questions. What drew you to this company? Why are you working there? What makes you get up each morning and go to work? What’s the problem your team is solving, or the opportunity it has before it?

As a manager on the Heroku Support team, I love helping people. Heroku is a platform that runs over 6 millions apps, receiving over 13 Billion requests per day. Our customers are unique in that most are programmers. I’ve been programming for almost 20 years and so I feel a unique connection to our customers. Sure, we get the usual “how do I reset my password?” tickets, but most of the time we’re there to help fellow programmers solve a difficult problem and get on with their day. This is incredibly rewarding for me and everyone on my team (who are also programmers).

So for me, I tell my team that I love helping fellow programmers get un-stuck. Programming is hard and I want every customer that opens a ticket to be amazed at how great our team is in answering even the toughest of questions. And as a manager, this is an easy idea to rally my team behind. It elevates the cause of our team and gives us a clear goal. In addition, when we have a clear goal ahead of us, it often helps solve many other problems the team faces. “Should we invest more time in better documentation?” Well, does it help our fellow programmers get un-stuck? Yes. Then do it. “We’ve seen a lot of tickets about this new feature.” It looks like we’re causing unnecessary issues for our fellow programmers. Fix the damn bug.

So find the common goal for your team. Don’t start with “what” your team does – it’s important, sure. But instead, start with “why”. Why are we all here? And once you have that, tell your team. Then repeat it. And repeat it again. Focus has a tendency to drift, but if you continually remind each other about your “why”, you have a better chance at building a healthy team.

Find and Develop Individual Strengths

Have you ever heard of Rudy? If you’re too young to remember, the movie “Rudy” was about a kid who grew up near Notre Dame. All his childhood he dreamed of playing football. When we grew up, he was accepted to Notre Dame, but not on the football team. But he worked hard, practiced, and helped out on the team. And one day … at the final game of his senior year, the crowd begins to chant: “RU-DEE! RU-DEE!” Finally, the coach turns to him in the final few minutes of the game and sends him out on the field. He makes a few plays and when the game was over, his teammates carried him out of the stadium on their shoulders.


But here’s the thing. Rudy sucked at football. But we love the underdog. It’s a great story to watch, but at some point you have to wonder: what was Rudy really good at? How would his younger years have looked different if someone told him the truth and helped him discover his natural talents.

On my teams, we work to find and develop strengths. We don’t ignore weaknesses, but we certainly don’t dwell on them for too long. Instead, we work together to find the things that come naturally to you and focus on developing those.

During one-on-one’s, I’m constantly looking for a glimmer in someone’s eye – that look of excitement when they’ve finished a certain ticket or task. The look or tone of voice that tells me that this thing is something they loved doing. Or I look for times when a task is done in half the time as expected. “Was this hard for you?” Nope, it came easy.

Bingo. Now we have a conversation starter. Why was it exciting to do that type of ticket? What about that task was easy for you? If it makes sense, we now have a path towards growth. Over and over on our teams at Heroku, we’ve grown people out of the Support team. Retention is not a metric for me. I am actively working with my team to grow them. “What?! What if you lose them?” I’m ok with that. I’d rather grow them and lose them, then force them into stagnation and keep them around.

Chances are, you have some incredibly bright and talented people on your team, but no one has told them not to play football. Sit with them, invest in them, and see what incredible things they’re capable of.

Create a High-Feedback Culture

Finally, we get to talk about one of the hardest things about leading a team: feedback.

There are many long and leather-bound books about this topic, so I don’t want to stay here too long. But I think there’s an unhealthy focus on this topic around critical feedback. Don’t get me wrong – providing critical or negative feedback is absolutely necessary and it’s something that’s a learned skill.

But we far too often ignore the fact that feedback must come from all directions. A healthy team not only extends feedback up and down the org chart, but members accept feedback. No, they crave it.

Two jobs ago, the CEO of our company popped his head into my team’s office. He scanned the room, and called out to me: “Can I borrow you for 30 minutes?” Oh crap. I headed to his office, where he had assembled people from all over the company.

“I’m giving this presentation next week and want your honest feedback. Don’t sugar-coat it. Tell me what I’m missing or what things I need to take out.”

It was terrifying to tell your CEO what was wrong with his presentation. But it was incredible. Not only did this guy preach “high feedback”, but he lived it, too!

And when your team isn’t worried about how you’ll take it, you’ll be amazed at how helpful that feedback can be. Ask for it! Don’t shy away. And learn to take it well – even the crappy ideas. Thank them, digest the feedback, then pick out anything you want to keep. But in doing so, you’re creating a valuable level of trust amongst your team.

Let’s talk about positive feedback. It’s the easiest type of feedback to give, but we rarely do it. Why is that? Why is it so hard for us to acknowledge someone for doing a good job?

According to a American Psychological Association survey, 93% of employees who reported feeling valued, said that they are motivated do their best work. And yet, we seem to only dole out praise when people leave the company.

Let’s start using the Homeland Security procedure: “see something, say something.” If you see something good on your team, just say it! Call it out! Some people don’t like public praise – that’s fine. But encourage people when they’re doing the right thing.

And when we do express praise, we tend to only focus on the work – not the person. We need to move from individual accomplishments to wholistic praise and gratitude. We need to move from “Nice work on that ticket” to “I’m grateful for you and your work on this team.” Do you hear the difference?

We don’t have workers on our team – we have people.


Dr. Henry Cloud said: “As a leader, you are always going to get a combination of two things: What you create and What you allow.”

Building a healthy team is an act of intentionality. You cannot turn it on and let it run by itself with no guidance, and expect a positive result.

And we all have an obligation to create positive, healthy work environments. This isn’t just a management thing. Think about the work you’re doing. If we’re honest, a lot of the work we’re doing won’t be around in 15 or 20 years. But the relationships, the friendships, the people’s lives on your team who you choose to pour into … those will last.

If you’re a manager, you’ve been entrusted with a few short years of someone’s life. It may one day end up as a bullet note on a resume. Or it could be one of the happiest and life-giving moments they’ll ever have. Choose to invest in the people around you.

Hi there, I'm Jon.

Writer. Musician. Adventurer. Nerd.

Purveyor of GIFs and dad jokes.