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October 6-8, 2024 • San Diego, CA

How to Build a Culture for Modern Workplaces

Most companies don’t invest in their people.

It’s unsurprising to see these team members be unhappy, underperform, and leave for a better company. 

To get the best out of your people, Shane Metcalf knew he had to radically change the way we work. 

Shane is the former Chief Culture Officer of 15Five. Before starting the company, Shane had invested in extensive personal development training that had changed his life. 

He knew how complex humans could be. Each person has a unique history of wounds, traumas, strengths, dreams, and passions.

Instead of ignoring this history to “get work done faster,” knowing this history can unlock a whole new level of innovation (and happiness). 

Shane calls this approach to work as Dynamic Human Leadership

Over the last 8 years of instilling a culture focused on personal growth, 15Five has grown from 0 to 200+ employees. They’ve won numerous Culture awards that include ranking #3 in Glassdoor’s 2020 Best Places to Work. 

Shane credits a big part of the company’s success to Dynamic Human Leadership. Now he’s here to break down what that looks like in practice. 

Get to know people at uncommon levels

Humans have a core desire to feel seen and understood. When we hear people’s stories and share our own, we build trust amongst the team. 

More trust = more safety = more creative ideas. 

There are two big things that Shane does for every team member when they join the company.

Best-Self Kickoff

They start every new hire with a Best-Self Kickoff

This is a 2-hour meeting between an employee and their manager to get to know each other at an uncommon level

  • What are your career ambitions?
  • What do you hope to get out of their new role?
  • How do you like to receive feedback? 

Questions like these. We don’t want managers to assume their new hire will be like the previous direct report. This conversation is an opportunity for folks in this new relationship to make the implicit, explicit. 

The Best-Self Kickoff builds a strong foundation between the employee and manager, which positively impacts their relationship for the years to come. 

Weekly 1-on-1s beyond work

Like other companies, managers have 1-on-1s with their direct reports to hold them accountable for the things they said they were going to do.

But at 15Five, they also add time for the manager to help with the employee’s personal growth. These are things they want to accomplish in life, beyond their career. 

This intention shows the employee how much the company cares about them as a human, not just as an employee.

Create opportunities for self-revealing and authentic relating

People often wear their “professional masks” when they’re at work and let loose to “be themselves” when it’s the weekend. 

15Five created a culture where people can let their true personality shine at work. To do this, they needed to create safe opportunities for people to take these masks off. 

Activity #1 – Question Friday

Once a month, the team gets on a Zoom call for Question Friday, a simple and powerful practice that connects the team together. 

The “Question Master” for that month chooses a fun question to ask the rest of the company. 

  • How did you spend your money as a teenager? 
  • What’s one of their happiest memories as a child? 
  • What’s the book that shaped your life the most? 
  • What teachers made a really strong impact on you?
  • If you had $20M in the bank, what would you do? 
  • In an alternate reality, what other career are you in right now? 

Then people will go into breakout rooms and share their answers in small groups. It only takes 30 minutes but everyone gets to know each other better in unexpected, delightful, and surprising ways. 

Even after 8 years, Shane still learns new things from his colleagues!

Question Friday gives people a chance to share a unique story that has made them who they are today. We feel more empathy and compassion toward each other when we honor and respect each other’s history. 

Activity #2 – Meeting on Ramps

Meetings at work generally focus on external items.

  • How many tasks were completed
  • How many leads came in that week
  • How much revenue was generated that month

While those things are important, Shane never wants to forget to check in with how each human is doing first. 

Shane calls this practice Meeting on Ramps

He believes our internal state shapes our ability to produce external results. So Meeting on Ramps is an easy way to create a little bit of space to hear how people are really doing. 

  • What’s a one-word emotion to how you feel?
  • What’s your internal weather report right now?
  • What’s your mental and physical energy level on a scale of 1-10? 

By asking these questions, we allow people not to hide how they feel and show that we accept them for how they are. 

You can have a more productive meeting where trust is built and everybody’s voice is heard.

Practice Radical Strengths Alignment

People are happier and perform better when they are utilizing their natural strengths. 

When people use their strengths regularly, they’re 3x more likely to be engaged and 6x more likely to report an excellent quality of life.

But not everyone knows what they are. So 15Five pays for everyone to complete assessments like Strengthsfinder. Then they host a half-day workshop with a facilitator to help people digest their results and integrate them in the workplace. 

This was a huge lightbulb moment for everyone on the team. It felt like an epiphany for many people to see how they could connect their natural strengths to the company. 

Shane shared that the best part was learning what other people’s strengths were. They helped managers better align their direct reports to tasks that were a better fit. 

If you want incredible results from your team, you need to help people unlock their genius and align their work to their natural strengths.

Make personal goal setting and life visioning a part of business as usual

Shane knew that when he felt aligned in his personal life, he went to work with more purpose. Because he better understood how work was closely connected to his personal and life goals. 

So he prioritized his team to take part in two transformational growth activities. 

Painted Picture

Entrepreneur Cameron Herold created a visioning exercise called the Painted Picture. This could be used for both your business and personal life.

The task is to write out the story of where you want to be in 3 years. 

Fill in as much detail of your future self as you can. 

  • Where you’re living
  • Who your friends are 
  • How much money you’re making
  • How your career is going
  • What you’re doing on a day-to-day basis

Write it in the present tense, as if it’s happening in the moment. Then read your Painted Picture every week to recenter you toward your goals.

3 Most Important Questions

Entrepreneur Vishen Lakhani has an exercise called the 3 Most Important Questions

  1. What do you want to experience in life?
  2. What do you want to learn?
  3. What do you want to contribute?

Answer these individually. Then paste your answer into a shared document that anyone at work can read. By sharing your answers, your team can see what you want and help you get there. 

Shane read that one of his team members wanted to drive a racecar. His uncle works for NASCAR and he arranged to have Mitch check out a core life experience. 

The company goes from a transactional relationship to being a vehicle to help people realize their dreams. 

Conclusion

Obviously the business has to win to support these Dynamic Human Leadership initiatives. 

But even in the beginning, Shane wanted to weave these parts in sooner than later so the company builds that strong foundation of trust. 

15Five is a shining example of how good things happen when you deeply invest in your team’s personal well-being. 

Shaping Your Culture: An Interview with Rian Finnegan

We’re thrilled to have Rian Finnegan, a leading Employer Brand Strategist who has significantly influenced major B2C tech companies such as Snap Inc., Peloton, Instacart, as a key speaker at Culture Summit 2024! 

We interviewed Rian to learn more about their Culture journey and why Rian’s session focused on building an employer brand at any stage of a company is unmissable at this year’s event! 


Q: Could you introduce yourself to our audience and provide them with an insight into your work in the Culture Space? 

A: My work has always centered on creating meaningful connections, whether it’s between bands and their fans, candidates and the right opportunities, employees and company missions, companies to causes, or local community members to each other via tasty vegan pastries. 

Over the past decade, I’ve dedicated myself to building and leading employer brand teams at large B2C tech companies (Snap Inc., Peloton, Instacart, Squarespace, Pandora Music), particularly during periods of significant transformation and scaling. 

In 2021, my partner and I embarked on a new adventure, co-founding Little Loaf Bakeshop in the Hudson Valley, New York. We focus on sparking joy through delicious, creative, and high-quality vegan pastries that incorporate as many local ingredients as possible. In our two short years, we have become known as a community-centric business that facilitates connection and provides a warm and welcoming place for all—with a specific lens on the LGBTQ+ community. 

I’m also deeply committed to advocacy and volunteer work. I serve on the executive board of Lesbians Who Tech, an organization that champions LGBTQ+ representation and visibility in the tech industry. Additionally, I volunteer as a marketing lead for Work on Climate, a non-profit dedicated to building the workforce humanity needs to address climate change in an equitable and just manner. 

Q: What initially sparked your passion for the HR/Culture/People domain, and how has it evolved throughout your career? 

A: Earlier in my career, I was an event/concert producer at Pandora Music. My boss at the time transitioned from an external events role to an internal culture role, and given how much I loved working for the company and the relevant skills I had developed in event production and marketing, I pitched her on a job and we worked together to bring me over to her team. The rest is [employer brand] history! 

Q: Can you recount the most valuable piece of work or culture-related advice you’ve received in your journey? 

“When it comes to shaping your culture, involve your employees early and often. They are the ones who truly shape and carry the culture, and taking their input seriously will help them feel recognized for the critical role they play.” – Me (I’m sure others have said something similar). 

“We have two ears and one mouth so that we can listen twice as much as we speak.” – Life advice, quote by Epictetus. 

Q: We would like to delve into the session you’ll be presenting at this year’s Culture Summit. What motivated you to choosing the topic of building an employer brand at any stage of a company? 

A: The world we live in—including the world of work—is evolving faster than we can keep up with. As a result, we are in an incredibly volatile work climate and job security and stability are not guaranteed. I believe this will lead to the continued normalization of professional “gig work,” aka consulting, freelancing, or fractional leadership, as well as the rise of individuals starting their own small companies, or even completely reinventing what they do for a living. 

This shift provides a pause that allows you to think about the kind of business owner or leader that you want to be, the kind of company you want to build, and how you want to show up in the world of work (and beyond). 

For those embarking on a freelance or fractional journey, this is an opportunity to look inward and articulate your values and operating principles, identify what you are uniquely positioned to bring to the table, and take ownership of your career narrative. 

For leaders building a new company, you are called to connect deeply with your team members as you define what kind of business you want to be, how you engage with each other and with customers and clients, and what is most important to look for when you hire. 

For those working full-time within a company, this exercise will help you more clearly understand your values and principles and how they connect with those of the organization, allowing you to be true to yourself and how you lead, drive projects forward, and engage with others. 

I am passionate about this topic, having recently transitioned from leading internal Employer Brand teams to owning a business with employees in a completely different field, in addition to doing professional gig work. There is immense power in these exercises that can help you grow your business, make tough decisions, and ultimately feel proud of the work you are doing—and how you show up when you do it. 

Q: If you had to highlight one compelling reason why attendees shouldn’t miss your session, what would it be? 

A: My session Building an Employer Brand at Any Stage Company, will be designed to get folks thinking about their own purpose, values, and EVP, regardless of whether they are working at a company, starting their own, or consulting. Doing so will help inform the kind of leader they want to be, the kinds of companies they want to work for, the types of clients they agree to work with, and, ultimately, how they move through the world. 

Q: Finally, what aspects of the Culture Summit in San Diego 2024 are you personally looking forward to the most? 

A: Seeing so many friends and meeting so many more! Also, learning about how leaders and teams are navigating this challenging job market and pushing their companies not to forget the human element of their workforce. 


Conclusion 

Rian’s session, “Building an Employer Brand at Any Stage Company,” is an unmissable opportunity for anyone looking to enhance their employer brand and foster a positive company culture. This session will provide invaluable insights and practical exercises to help you define your company’s values, purpose, and culture.  

Don’t miss out on this inspiring session on Monday, October 7, from 2:00pm to 2:45pm PT. Mark your calendars and join us at the Culture Summit 2024! 

Learn more about Rian Finnigan 

Mastering the Art of Constructive Feedback

Giving feedback to our team members can be awkward and uncomfortable.

We’re afraid this feedback will damage our relationship with them. And these feelings are valid–our brains view criticism as a threat to our survival. 

When someone asks to give us feedback, our amygdala fires up and we go into fight or flight mode. Feedback attacks our feelings of stability and comfort. 

But at the same time, we need feedback to grow into our best selves.

Feedback gives people the opportunity to be better team members, partners, and human beings.

When delivered well, feedback can actually strengthen your relationships.

So if we know feedback is tough but essential, how do we give feedback in a healthy way?

Meet Shaun Sperling, a facilitator and coach who helps organizations feel more connected to each other. Shaun sees two big mistakes people make when giving feedback

  1. They don’t prepare what they plan to say and
  2. They blurt out whatever comes up

But when people don’t prepare feedback well, there’s a higher chance that their feedback won’t land well. And this will damage the relationship.

Shaun has a simple yet brilliant framework on how to easily prepare your feedback. Let’s dive into his philosophy around feedback first. Then we’ll share his FAIR framework that will prepare you for your next important conversation.

FAIR Framework

Feedback is not about criticizing. Feedback is about aligning with the other person’s interests.

Before you give feedback, ask yourself:

  • Why are you giving this feedback?
  • What do you care about?
  • What’s in it for them?

Team members want to develop into the best version of themselves. Good managers want to contribute to their team member’s professional goals.

So when a manager gives feedback to their team members, they are helping them grow. And if they grow, their work is better which aligns with the company’s goals.

Everyone wins.

So how do you prepare for conversations like these? The FAIR framework has three parts.

#1 – Facts

Let’s imagine that Manager Sally noticed Employee Tim had sent poorly written emails to important clients X and Y.

These messages had spelling mistakes and an unprofessional tone.

It’s not enough to tell Tim, “Your emails are really bad…”

Which emails?

The ones he sends to the team? The messages that you two exchange together? And how do you define “bad”?

Sally needs to gather all the data that she sees and be crystal clear of what’s wrong. A good way to think of this is, “What can be proven in court?”

Do you have hard evidence that can support your claims?

In this case, Sally can specify that the last 5 emails that Tim has sent to clients X and Y have had Z combined mistakes.

#2 – Impact

Next, Sally needs to ask herself: what’s the impact of the thing she’s giving feedback on?

Potential ways this impacts the company:

  • Clients think that the company’s service/product will also be sloppy and rushed.
  • Clients feel they’re not important enough to be assigned a more senior team member
  • Client doesn’t trust that Tim is the right person for the job and decide not to renew

It could be any number of reasons. Sally must choose a message that’s relevant to her organization.

#3 – Request

Lastly, Sally can brainstorm a couple of options that can help fix this behavior.

Maybe she can proofread their emails to external stakeholders before Tim sends them. Or take some work off of Tim’s plate to give him more time to write these emails. Or enroll them in a grammar class.

She can have these ideas prepared before starting the conversation.

How to Have the Conversation

Now that you’ve prepared for the conversation, there’s a better chance the other person will hear your feedback.

During your next 1:1, open the dialogue to address the issue and get a sense of where the other person is.

Manager Sally: Hey Tim, I want to talk to you about the last three emails you’ve sent to X client. I’ve noticed some grammatical errors, and the emails feel a little messy. Have you noticed that?

Tim might respond that he has noticed this and take full responsibility for these mistakes. Or he might say how he had no idea that was the case.

Either way, start the conversation with a curious question instead of an interrogation. This will make Tim feel less defensive and be more open to engage in dialogue.

Other questions to open the dialogue:

  • “How’s your workload right now?” – This question lets you see if they’re overworked.
  • “How have you been feeling lately?” – This question sees if outside factors may have been affecting their performance recently.
  • “What do you think you’re doing well at your job right now? And where do you think you could use more support?” – This question sees how self-aware they are of strengths and weaknesses. 

Let’s continue the conversation as if Employee Tim was unaware of his behaviors.

Employee Tim: Oh no, I haven’t noticed…

Manager Sally: That’s okay. We’re all moving pretty quickly these days. But I’m curious what are your thoughts on the last couple of emails that you’ve sent to X client?

Employee Tim: I’ve never thought about it, but I guess they kind of look unprofessional…

Manager Sally: I agree. Sending messages like these can come across like we don’t care about the quality of our work. What do you think we can do differently to change this? How can I support you with this?

Tim should understand the impact of this behavior and get on board to fix it. Sally did a great job ending on a supportive note.

We always want to reaffirm your role with the other person. Stress that you are on their team and you want the very best for their success.

Manager Sally: Hey, I know this is a challenging conversation and I just want you to know that I am in your court. So whatever you need from me, I’m here to support you 100%.

To wrap things up

We give feedback to better align ourselves with the other person. It’s about getting closer to the other person, not further from them.

So don’t think about feedback as criticizing their behavior. It’s seeing an opportunity for them to grow into a better version of themselves. And when you have the right intentions, giving feedback can feel like a gift.

Never give feedback without a plan. Use the FAIR framework to prepare. When you have the conversation, open the dialogue with curious questions. This helps you better understand where they’re at before jumping to conclusions.

Bridging the Saying-Doing Gap: Transformative Strategies for Cultural Consistency

In the quest to foster consistently great experiences across the employee lifecycle, Derek Newberry, a luminary in organizational culture and design, is poised to illuminate the path at Culture Summit 2024.

 As the Head of Organization + Culture Design at co:collective, adjunct professor at UPenn, and author of “The Culture Puzzle,” Newberry brings a wealth of knowledge and insight into the dynamics of cultural architecture.

His upcoming fireside chat, “Cultural Architecture: A New Approach for Creating Consistently Great Experiences Across the Employee Lifecycle,” promises to equip attendees with the practical tools needed to bridge the often pervasive “saying-doing” gaps within organizations.

Culture Summit caught up with Derek to learn more about his interest in this area and gain a preview to his upcoming session.


What initially sparked your passion for the HR/Culture/People domain, and how has it evolved?

“My fascination with organizational culture began at UPenn, where I received my PhD in Cultural Anthropology. I’m driven by the power of culture to unite people in overcoming challenges and achieving collective greatness.”

Can you recount the most valuable piece of work or culture-related advice you’ve received?

“The notion that humans are the ‘storytelling animal,’ as stated by historian Yuval Harari, resonates deeply with me. Great storytelling is crucial for leading and transforming organizational cultures.”

What motivated you to choose this particular topic for the Culture Summit?

“The pervasive ‘saying-doing’ gaps in organizations, especially post-pandemic, highlight a disconnect between stated values and actual behaviors. My session addresses this critical issue, offering solutions for realignment.”

If you had to highlight one compelling reason why attendees shouldn’t miss your session, what would it be?

“Attendees will gain actionable tools for aligning organizational behaviors with strategic visions, ready for implementation.”


In Summary

Derek Newberry’s session at Culture Summit 2024 offers an unprecedented opportunity to delve into the mechanics of cultural consistency, ensuring your organization’s values are reflected in every action and decision.

Don’t miss this chance to transform your approach to organizational culture and bridge the gap between aspiration and reality.

 Join Culture Summit 2024 in San Diego on Monday, October 7,and attend , “Cultural Architecture: A New Approach for Creating Consistently Great Experiences Across the Employee Lifecycle,” 11:15 a.m. to 12:00 p.m. PT to learn more!

Human-Centric Design in Hybrid Workspaces: An Interview with GoFundMe’s Giana Rodriguez 

As Culture Summit 2024 approaches, we were thrilled to sit down with Giana Rodriguez, Sr. Manager of Workplace & Employee Experience at GoFundMe. Giana brings deep expertise in creating engaging employee experiences that build vibrant workplace cultures. We caught up with her and delved into her approach to managing employee experience in hybrid environments. 


Q1: Can you share what ignited your passion for HR and how it has evolved? 

“I have always had a passion for employee relationships and people strategy. I began developing people programs early in my career in the education and volunteerism space and have always taken an interest in ensuring strong cultures within the organization.” 

Q2: What’s the best piece of advice you’ve received regarding workplace culture? 

“The work is about empowering others to succeed, which reflects your success. Once I realized that it was ok that my passion didn’t reside in one field, product, or mission, but was about helping the people doing the work, I felt liberated to follow that passion.” 

Q3: What motivated you to focus on ’employee experience design in a hybrid workplace’ for your session at this year’s summit? 

“Working environments look different from company to company and it can be difficult to find the ‘perfect’ Employee Experience happiness solution. My session is about anchoring Employee Experience work in a foundation that allows for flexibility and creativity while still tracking data and providing space for reflection and forward thinking. It challenges the idea that there is a ‘perfect’ solution, but rather a framework that focuses on meeting people where they are at and addressing their humanity first.” 

Q4: Why should attendees not miss your session at Culture Summit? 

The Workplace & Employee Experience model I will be highlighting can be used for any type of company, employee/volunteer demographic, and with any budget. The session is centered around building programs that are human-centered, easy to communicate value to employees and leadership, scalable, and flexible.” 

Q5: What aspects of the upcoming Culture Summit are you most looking forward to? 

“Connecting and chatting with all of the amazing people who are dedicated to such important work. I always learn new things when I meet people doing the same work and feel a part of something greater.” 


Giana Rodriguez’s insights into employee experience design are invaluable for anyone navigating the complexities of hybrid workplaces. Her session at Culture Summit 2024 will equip you with the strategies needed to foster a supportive and adaptive work environment. Learn more about her session ‘A people-first approach to employee experience design in a hybrid workplace.’ 

Remote Revolution: Inside the Trailblazing  ‘Shippo’s Everywhere’ Model

In an era when the workplace concept is being redefined, Teryle Aguilar, SVP of People at Shippo, is leading innovation with Shippo’s remote-first model. With a background that spans DoorDash to NBCUniversal, Aguilar brings a wealth of experience in HR and people team leadership.

Ahead of her session at Culture Summit 2024, we dive into her journey, the evolution of her passion for HR, and the groundbreaking “Shippo’s Everywhere” strategy that is setting new standards for remote work.

What initially sparked your passion for the HR/Culture/People domain?

“My passion was ignited under an inspiring HR leader during a summer job. Although my initial path was in biochemistry, I discovered my true calling in HR, leading to a career dedicated to enhancing workplace cultures across various industries.”

Can you recount the most valuable piece of work or culture-related advice you’ve received?

“One key lesson is that you cannot simply copy and paste cultural practices from one company to another and expect success. It’s crucial to tailor strategies to fit your unique organizational context.”

Delving into the session you’ll present at this year’s Culture Summit can you tell us what motivated you to choose this particular topic?

Remote work remains an unsolved puzzle for many. At Shippo, we’ve experimented extensively with our ‘Shippo’s Everywhere’ model, finding unique ways to engage our team and enhance our culture. This session will share our journey and insights from these experiments.”

If you had to highlight one compelling reason why attendees shouldn’t miss your session, what would it be?

“This session will unveil unique remote work strategies developed at Shippo, addressing leadership challenges and showcasing our innovative programs and data-driven insights for the future of ‘Shippo’s Everywhere.'”

In Summary

Teryle Aguilar’s session, “Shippo’s Everywhere” – Strategies & Insights from Shippo’s Innovative Remote-First Model, at Culture Summit 2024 is a must-attend for those eager to explore the frontiers of remote work and cultural transformation. Join us on Tuesday, October 8, from 10:15 to 11:00 AM in San Diego to learn more!

Empowering Change: Inclusive Benefits in the Face of Rising Anti-LGBTQ+ Legislation

In an era where visibility for LGBTQIA+ individuals is at an all-time high, yet legislative challenges continue to surge, Haley Everheart and Megan James step forward to lead a crucial conversation at the Culture Summit 2024.

As veterans in their respective fields, their upcoming session, “Breaking Barriers: Building Inclusive Benefits in the Wake of Anti-LGBTQ+ Legislation,” promises to be a beacon of insight and empowerment for organizations striving to fully support their LGBTQIA+ employees.

Culture Summit caught up with them both to learn more:

 Could you introduce yourselves and share more about your roles within the Culture space?

Megan: “Specializing in employee benefits for over 15 years, I focus on empathetically supporting employees and strategizing benefits as a crucial part of business culture.”

Haley: “With over 15 years in digital storytelling and community building, I now lead marketing at FOLX Health, enhancing LGBTQIA+ care through diverse audience engagement.”

What initially sparked your passion for the HR/Culture/People domain?

Megan: “Benefits were my entry point, evolving from a ‘warm and fuzzy’ addition to a strategic business component that retains talent by supporting various life phases.”

Haley: “My passion stems from early interests in novels and cultural production, further deepened by my communications and ethnography studies and allyship for marginalized communities.”

Can you recount the most valuable piece of work or culture-related advice you’ve received?

Megan: “Decisions made in the best interest of employees are always the ones you’ll stand by without regret.”

What motivated you to choose this particular topic for the Culture Summit?

Megan: “With over 450 anti-LGBTQ+ bills tracked by the ACLU, there’s a pressing need for action beyond employee resource groups to support employees genuinely.”

Haley: “Facing an unprecedented number of anti-LGBTQ+ bills, it’s crucial to discuss creating inclusive organizations amidst increasing visibility and societal backlash.”

If you had to highlight one compelling reason why attendees shouldn’t miss your session, what would it be?

Megan: “Awareness is the spark that initiates change.”

Haley: “Your LGBTQIA+ employees need you more than you realize.”

Conclusion

Now is the time to gain vital insights for creating a supportive and inclusive environment for all employees.

Don’t miss Megan and Haley’s session “Breaking Barriers: Building Inclusive Benefits in the Wake of Anti-LGBTQ+ Legislation” on Monday, October 7, from 10:15 am to 11:00 am PT at Culture Summit 2024, San Diego!

Leading from the Heart

If people are the most important resources in a company, why aren’t companies prioritizing how they treat their people?

The cultures at traditional workplaces are still rooted in fear–the managers act like hovering dictators and the employees don’t feel safe or motivated to do their best work. 

But that doesn’t make business (or human) sense. If human capital is a company’s greatest asset, shouldn’t we create a culture that helps our people bring their best selves and do their best work?

This is the core idea behind Claude Silver’s philosophy: Heart Centered Leadership. Claude is the first-ever Chief Heart Officer at VaynerMedia where her job is to infuse empathy throughout the whole organization and impact every employee. 

She joined when they had 400 employees and helped them scale their culture to now 2000 people. Heart Centered Leadership is all about bringing heart and humanity into the workplace and creating brave spaces for people to thrive.

Here are three biggest takeaways on how you can bring Heart Centered Leadership into your organizations. 

#1 – Create a Psychologically Safe Space For Feedback

Feedback is a gift. 

When we withhold giving feedback to someone, we hold back the opportunity for them to develop. People need feedback to help them grow. 

To create a strong feedback culture, you need to be able to give it, encourage it, and solicit it. All this can’t be possible unless people feel psychologically safe. 

Claude recommends five rules to make feedback more impactful amongst your team.

  1. Be kind: Everyone makes mistakes. It is what makes us human. When you give feedback, empathize with how the other person might feel and lead the conversation with kindness.
  2. Be clear and specific: Don’t say “Your slide deck was bad.” That person doesn’t know what was wrong with the slide deck. Instead, get ultra-specific about the issue.
  3. Be sincere: You want the other person to feel like you’re on their side and you’re deeply invested in their growth. You want them to feel like you’re riding shotgun in their car on their adventure.
  4. Be current: Give feedback within the day or the week. Don’t save it for three months later or in their annual review. You want to create a frequent feedback loop where it doesn’t even feel like feedback. It’s just another conversation. 
  1. Make it actionable: End with a tactical way to approach the next steps on resolving the issue. 

Here’s an example of putting these rules together. 

​​“Hey Bob, that deck that you just showed all those clients had a lot of spelling mistakes in it. I know mistakes can happen from time to time (I misspell things often too). Let’s sit down and walk through the deck together so I can show you what I see. 

Afterward, we can chat about potential solutions that’ll prevent this for the future. I use a tool called Grammarly that I can share with you. Or we can proofread the next slide deck together before it goes out to a client.”

Bob will be much more receptive to a message like this than if Claude had said, “Your slide deck sucked. Do better next time or else I’ll take you off this assignment.”

#2 – Build Your Emotional Optimism

85% of the thoughts in our head are negative. And these same thoughts come up repeatedly as we go about our days.

  • “I’m not good enough.”
  • “I’m not smart enough.” 
  • “I’m not fit enough.”

When we have these thoughts, we start to look for evidence to confirm that we’re not actually good enough. When we believe your teammates aren’t smart enough to do their work well, we lose trust in them. 

We treat them differently, and they notice. 

But what would life feel like if we had more than 15% of positive thoughts in our heads? How would our team feel if we believed in their potential to do amazing work? The world would be absolutely different. 

Claude prides on having an immense amount of emotional optimism. This is the ability to take obstructive thoughts and reframe them so you can see the silver lining. 

To zoom out from your negative thoughts and see the bigger picture. Then transform those thoughts into a more positive and optimistic view. 

“The way you see people is the way you treat them and the way you treat them is what they become.”

Despite your team’s imperfections, choose to see the unlimited potential in your people. On a more philosophical level, human kindness is always the way. We are wired to belong. We are better when we work together and commit to finding truth together.

When we talk together in new and different ways, we get better results, and everything moves forward. 

Lastly, it’s one thing to just be optimistic. But optimism with action creates results. And all things grow when immersed in love.

#3 – Give Attention and Be Generous

Attention is the purest form of generosity.

Attention unlocks serotonin that gives you this feeling of calm and happiness. It’s an amazing feeling when managers walk through their direct report’s slide deck, give great feedback, and offer ways to help unblock their biggest challenges. 

The direct report feels seen, understood, and recognized for their efforts. They feel like you care. 

Generosity is when you freely give your time, energy, or resources to someone. 

Generosity unlocks oxytocin that promotes feelings of love, bonding, and well-being. It’s called the love hormone or the hugging drug because it’s that powerful. Author Simon Sinek has a great quote, 

“When people are financially invested, they want a return. When people are emotionally invested, they want to contribute.”

When you give someone attention and generosity, they see that you’re emotionally invested in them, and this makes it more likely that they’ll be motivated to be invested in whatever you’re doing. 

To Sum it Up

If people are the most important resources in a company, companies must prioritize treating their employees well. Heart Centered Leadership is an amazing philosophy to accomplish this goal. 

It’s all about leading with the heart. To connect as humans and be incredibly empathetic to the people that we’re serving. Heart Centered Leadership works best when there’s a culture of physiologically safety, emotional optimism, and generosity. 

Innovating Work Cultures: Leslie Laws on Thumbtack’s Virtual-First Transformation

 In today’s dynamic work culture, adaptability and innovation are essential. Leslie Laws, with nearly 15 years in HR and organizational development, leads Thumbtack’s shift to a virtual-first model.  

Ahead of her Culture Summit 2024 session, “Rethinking Work: Thumbtack’s Virtual-First, Not Virtual-Only Transformation, Leslie offers insights on reshaping work environments and the inspiration Thumbtack’s transformation can deliver. 


Could you introduce yourself and tell us about your role within the Culture space? 

“I’m a People leader who has been experimenting in this space within high-growth companies for almost 15 years. I’m now a VP, HR at Thumbtack, leading a team of HRBPs, DEI, and Org Dev leaders accountable for fostering a high-performing, inclusive, and engaged organization.” 

What initially sparked your passion for the HR/Culture/People domain, and how has it evolved throughout your career? 

“My passion was ignited by the significant impact that good people management can have on someone’s work life. Influenced by thought leaders and innovative companies, my belief in the link between engaged employees, innovation, and business success has only grown stronger over the years.” 

Can you recount the most valuable piece of work or culture-related advice you’ve received in your journey? 

“The best advice was to fully consider and understand opposing viewpoints when making decisions. This approach not only enhances decision-making but also enriches our professional journey, especially when shaping company culture.” 

We would like to delve into the session you’ll be presenting at this year’s Culture Summit. What motivated you to choose this particular topic? 

“The unprecedented changes in the work environment over the past few years and the need to adapt and thrive inspired me to choose this topic. It’s crucial to remain agile and open to learning to keep pace with the evolving world.” 

If you had to highlight one compelling reason why attendees shouldn’t miss your session, what would it be? 

“Thumbtack’s transition to a virtual-first organization is a unique journey with valuable lessons for anyone interested in successfully navigating such a shift. Our experiences can help increase the collective odds of success in this new work environment.” 

Finally, what aspects of the Culture Summit in San Diego 2024 are you personally looking forward to the most? 

“I’m eagerly anticipating the opportunity to learn from my peers in the space, which is always an incredibly enriching experience.” 

Don’t miss the opportunity to learn from Leslie’s experiences and Insights! 

Mark your calendar for “Rethinking Work: Thumbtack’s Virtual-First, Not Virtual-Only Transformation” on Monday, October 7th, from 9:15 to 10:00 AM PT at Culture Summit 2024, San Diego!  

7 Ways to Create an Emotionally Fit Culture

We spend an enormous amount of time at work. Like 90,000 hours worth.

If people are going to work this much in their lifetime, it’s natural to be selective in choosing who they work for. This gave companies an idea: what if we offered people more than just a place to work? What if we covered their meals, took care of their dry cleaning, and even washed their cars for them? 

They assumed amazing perks = happy employees = good quality work. 

But is this actually true? Can we just give employees beer on tap and trust that’ll motivate them to do their best work?

But is this actually true? Dr. Emily Anhalt had to find the answer. She’s a clinical psychologist, and co-founder of COA, a startup that provides employee mental health benefit services. 

Dr. Anhalt did a research study on what makes up an emotionally fit culture. Her findings identified seven key traits.

  1. Healthy Leadership
  2. Agency and Trust
  3. Culture of Play
  4. Community and Belonging
  5. Proactive Mindset
  6. Stability and Integrity
  7. Communication and Transparency

We’ll break down what each one means and share tactical advice on how you each trait to create an emotionally fit culture in your workplace.

Trait #1: Healthy Leadership

Leaders need to be emotionally healthy themselves to have the abilities to lead an emotionally fit culture. 

As the leader, you’re building the ethos of the company. Your emotional baggage and past traumas will seep into the relationships with your team and the business decisions you make without you even realizing it. 

Even if you create healthy policies, change won’t happen if the employees don’t see you live out those values. 

How do you build better leadership health?

The best thing you can do is find a great therapist or work with an executive coach. 

As leaders, we often feel like we’re supposed to do everything on our own. But the truth is, everyone needs support. A therapist can help you understand your patterns, emotions, and relationships. A coach can help you think through difficult leadership decisions. 

Dr. Anhalt can’t think of an investment with a higher return than this.


Trait #2: Agency and Trust

Our main job as leaders is to figure out our team needs to do their job well and then set them up for success. 

Because guess what? People have different needs. 

  • Some people need noise and others need time alone. 
  • Some team members thrive in an office and others do their best work at home. 
  • Some employees are really good at sharing ideas on the spot. Others may need time to process their ideas before presenting them. 

Helping your team know these things about themselves, and fostering a culture where they can get their needs met, is how you get people to perform at their best (and also be the happiest). But this requires a space where people are comfortable to be honest and vulnerable. 

How do you build more agency and trust within your team? 

When Dr. Anhalt onboards a new team member, she invites them to complete an emotional fitness survey. This short questionnaire uncovers how each person works best so their managers (and teammates) can best support them. 

Some questions include:

  • Do you like to be praised in public or private?
  • Do you prefer feedback that’s direct and blunt? Or more gentle and kind?
  • How do you like to be cared for or cheered up during a tough time?
  • Do you prefer to be supported closely? Or would you prefer more space and freedom? 
  • What else do you want us to know about you? 

If someone prefers to be supported closely when they work, Dr. Anhalt will match them with a manager who likes to mentor others closely. If someone prefers a little bit of space before checking in during a tough time, Dr. Anhalt would leave them alone for a few days and circle back later with some flowers. 

By knowing how our team members like to be supported, we match their love language, making them feel seen and understood. At Dr. Anhalt’s company Coa, everyone on the team has filled this out, including the founders. Anyone can access anyone’s answers, and they’re editable over time because it’s natural for people’s needs to change (which is a great thing).


Trait #3: Culture of Play

Play is the ability to foster a safe space of connection and creativity. Playing in the workplace is hugely undervalued because play isn’t just about games. Dr. Anhalt likes to think of the improv definition of play, which is that when someone approaches you with an idea, you don’t just say “yes.” You respond with “Yes, and…” following your own ideas. 

Together, the two of you get somewhere that neither of you could have gotten alone. 

But the thing about play is that it can be tough to do. When we play, our guards come down, and that can be scary for people who work really hard to keep their guards up. The good news is that it gets easier over time, especially if leadership shows this is something that’s important in their culture. 

How do you build play?

One simple idea is to start your meetings with a quick icebreaker game. This connects people, gets them on the same level, and prepares your team to work more collaboratively. 

If you’re interested in a list of icebreaker games, email [email protected]. Dr. Anhalt has curated a bunch of games that are easy and fun to play at work. A lot of them can be done remotely too.

Trait #4: Community and Belonging

People will go to extraordinary lengths to protect a community they feel a part of. That’s the feeling you want for your team. 

You want people who feel like they truly belong. A team with high levels of psychological safety has the ideal environment to foster deep and meaningful connections. 

How do we build community and belonging? 

There are many ways to do this like team offsites or just being kind to each other. But Emily believes one of the most important things we can do is make sure that the community feels safe to people who come from many different perspectives. 

This could be through language, making sure your job descriptions aren’t gendered. It could be through imagery, making sure your website represents a diverse group of photos. If you could be through your events, making sure there are vegetarian options at your company outing. 

Doing this on our own is tough because you’ll have plenty of blind spots designing changes from one perspective. It’s important to bring in diverse minds to ensure you hear from different points of view.

Trait #5: Proactive Mindset

Preventing issues is simpler than fixing them. Opting for a healthy lifestyle now, with regular gym sessions and nutritious meals, is wiser than dealing with health problems in your 70s.

Similarly, taking a proactive stance at work to prevent issues is crucial. Instead of waiting for problems to arise and then scrambling to resolve them, it’s better to address potential challenges before they become fires you need to put out. 

What does a proactive mindset look like in practice?

One thing that Dr. Anhalt recommends is to add policies that prevent burnout. Because burning out is something that’s much easier to prevent than it is to fix. 

If you wait until people are already past their limit, it’s too late. They’re exhausted, unable to perform at their best, and might even leave your company in search of an organization that can better support their needs. 

Instead, we want to make sure a person never gets to that place of burnout. Here are some simple ways to do this:

  • Offer a no questions asked mental health day policy
  • Discourage email and Slack on nights and weekends
  • Allow work-from-home days
  • Encourage people to actually take vacation
  • Add “self-care time” into your calendar

Trait #6: Stability and Integrity

When you’re building a company, things are bound to change. The product will change, the team will change, or the entire direction of your startup could change 10 times during your tenure.

That’s expected, but at the same time, stability is important for our mental health. We need consistency in some areas of our life to weather the unexpected storms that are bound to happen. 

For example, having a stable core in your team that people can count on can help you endure  hard times. Or perhaps your product changes direction but your team’s core values don’t change the type of people you’re bringing on. 

How do we create stability in your company?

One powerful way is to create traditions and rituals. Traditions and rituals are actually at the heart of every ongoing culture, and work should be no different. 

They strengthen bonds, create reliability, and increase joy. You don’t have to overthink this one. You can try a bunch of traditions and rituals and just see what sticks. People will lean into the ones that they like and they’ll kind of lean away from the ones that don’t go as well. 

At Coa, they put a “mission” every Monday like “tell us about a time you overcame a tough challenge in your life and what got you through it.” The team posts their answers on Slack throughout the week and on Friday, everyone votes on which answer impacted them the most. 

This practice has helped their team learn so much about each other. Plus this activity lives and breathes their values around transparency and vulnerability. 

Another tradition Emily has seen is called Above and Beyond day. Once a month, someone gives a shout out to a colleague who has been extra kind, set a good example, or accomplished an important milestone. That colleague gets a special prize. Then the person who won gets to shout out the next person for the following month. It’s a way to recognize each other and reward hard work. 

A simple one anyone can do is celebrate anniversary markers. For every year someone has been at the company, they earn some kind of marker to indicate how long you’ve been around. Maybe it’s a patch on your company jacket or a wooden block that you keep on your desks. 

Emily recommends having someone be the “owner” of these rituals to ignite the initial spark and continue the momentum.

Trait #7: Communication and Transparency

Effective communication is everything for team success. Good communication prevents misunderstandings, solves conflict, and ensures we’re all working cohesively toward the same goal. 

A common misconception is that people can’t handle honest and transparent communication. But the reality is, people want the truth, even if it’s tough to hear. 

How do you communicate better in your company?

It’s important to create a structure of ongoing feedback. It’s common for companies to wait until someone does something wrong before giving them feedback. But having a structure for feedback gives people transparency into how they’re doing at all times. 

This could look like a quarterly conversation (recommended) or an annual review (less frequent, but still good). 

Another event that Emily does is Feelings Friday, a space where her team talks about things that have gone really well. Wins, times where they’ve felt supported, and shoutouts for one another. 

It’s also an opportunity to share moments where they felt unsupported and share things that didn’t go well. Or sometimes they share personal news like, “I had a tough week because I’m going through some personal stuff. Sorry if I’ve been a bit distant lately.” 

These meetings are a chance to catch small problems and prevent them from getting bigger. It also serves a way to genuinely hear what’s going on in each other’s lives.

To sum it all up

We invest a significant portion of our lives in the workplace. While enticing perks may contribute to employee happiness, what matters most is fostering a thriving and emotionally fit culture. 

Dr. Anhalt’s research further identifies seven key traits that make up an emotionally fit culture. 

  1. Healthy Leadership
  2. Agency and Trust
  3. Culture of Play
  4. Community and Belonging
  5. Proactive Mindset
  6. Stability and Integrity
  7. Communication and Transparency

By embracing these traits, you can proactively cultivate an environment that radiates psychological safety, which promotes better trust, collaboration, and the well-being of your teams.