Why Investing in Meaningful Work Relationships Increases Employee Engagement

Critical steps to improve your employee retention & engagement by creating team cohesion and reducing silos in the workplace.


This strategy was used at multiple companies over the last year. Here were the results:

  • Turtle Bay Resort - increase in 5% of employee engagement.

  • Outside - increase in cross-functional connectedness and 10% increase in employee engagement

  • Parents & Children Together (non-profit) - increase in employee engagement by 8%

Now, with that out of the way, let’s talk about you and your current situation.


There are a lot of tools out there that don't properly meet today’s team building/team cohesion needs…

  • Escape rooms

  • Dinners and drinks

  • Long speeches

  • “Fun” team outings not grounded in a purpose other than “having fun together”

You’ll see why the above activities don’t meet today’s team cohesion needs by asking yourself the following questions:

  1. Think about the stuff people go home and complain about to their spouses and friends about their workplace. Do you really think an escape room is going to move the needle on that? What usually plays out is that people go to the activity, have a decent time, and then the activity usually reflects the way we work (ie person X is usually the leader on projects and is the leader at the escape room), but because there is no debrief afterwards understanding this patterning, nothing changes. You get some positive feeling afterwards, but it’s fleeting. Nothing really gets fixed at the above events.

  2. What was the impact of the event? If the answer doesn’t pack a punch and have a high ROI, consider that you might be missing something in the execution. The legacy way of doing team building is missing the boat in my opinion. It’s like being on a cooking show, having access to the same ingredients, and someone makes a bland piece of chicken vs another chef makes one of the best meals ever. Be better than bland. If you want to keep your people and increase their happiness at work, be better than bland.

Who is this strategy for?

This strategy is tailored for teams operating in distributed or fully remote setups, aiming to enhance team cohesion amidst challenges such as decreased engagement metrics, interpersonal conflicts, lack of alignment, and feelings of being unheard or undervalued among team members. It is particularly relevant for environments where individuals resort to team-switching instead of addressing communication hurdles.

These challenges typically arise in the following segments:

  1. Companies with distributed work forces

  2. Design teams & PMs (ie product teams) in technology or software companies

  3. Product teams with cross-functional partners

  4. Siloed organizations

  5. Companies Series B-D with international distributed workforces

  6. Foreign companies building a US team

  7. US team building foreign teams


Here is my thesis for why Executive Offsites even exists…

In order to build a high-performing team, you need to build meaningful work relationships, have people develop self-awareness for group dynamics at play, and build up psychological safety.


A Brief How-To On Creating Meaningful Work Relationships

In order to have better work relationships, you need to have: 

  1. Productive and honest conversations with all pertinent parties about what’s not working so that each person feels heard, valued and understood

  2. A memorable shared experience that furthers the connection, while being enjoyable, expansive, and nurturing to the soul (an experience that naturally produces serotonin and oxytocin; this is what happens for example when a shared awe-inspiring moment or a connected conversation happens)

  3. Co-create aligned deliverables and address initial hurdles as a team. Embrace each stumble as a new learning experience in conflict resolution. This approach not only navigates conflicts, but also ensures that everyone feels valued and heard, fostering a positive and productive atmosphere.

Again, who is this for?

Pay attention if you:

  1. Are trying to plan your team’s annual meeting or offsite Are a CEO or chief of staff responsible for in-person experiences and offsites within your team or organization.

  2. Are looking into etiquette classes for your company with so many not knowing office etiquette, having worked from home for the past few years. (yes, that is a growing field)

Now before we get into the specifics, I want to share with you the core concept of team offsites.  If you can internalize the following sentence, everything will be much easier for you and employee engagement and team cohesion will improve:

The fastest and most predictable way to create team cohesion is with offsites that have teammates humanize one another. 


Who am I, and what makes me qualified to teach you this stuff?


My name is Kendall Wallace. I’m a corporate offsite designer, curator and facilitator.

Not that it really matters, but I have a History & Global Culture & Commerce Degree from The University of Virginia.

I’ve worked for Big Tech, for Meta, and for smaller start-up tech companies who became unicorns (Reef Technology). I’ve worked for in-person teams and distributed workforces. 

Most recently I founded Executive Offsites and through it, I’ve worked with or instructed B2B leaders at companies like Meta, Outside, Turtle Bay Resort, and more. 

I specialize in creating immersive experiences that ignite personal and professional connections, fostering a deeper sense of vitality and harmony with oneself, nature, and others. Recognizing the shortcomings of traditional corporate offsites, I founded Executive Offsites to provide enriching travel experiences that nourish mind, body, and soul, while cultivating workplace safety and honesty.

As a connection expert, I facilitate transformative experiences for teams, emphasizing humanization over turnover. With a proven track record of guiding over 1,000 individuals across 75 groups, I enhance communication, reveal blind spots, and promote work-life balance, resulting in happier, more effective communicators.

My mission is to empower teams to embrace life to the fullest, overcoming barriers to joy and connection in the workplace. Through targeted attention to teamwork and workplace dynamics, I aim to elevate the quality of work life.

In addition to my work, I am an EFT practitioner, leveraging psychological reprogramming to support personal growth. Residing in the North Shore of Oahu, I pursue my passion for surfing while leading monthly dinner clubs and sisterhood circles.


Now, let’s get into the steps on how to create offsites that create meaningful work relationships.


Step 1: Set the intention around your gathering. Focus on the “why” not the “what.” Because “getting the team together” really isn’t good enough as a reason to get together; if it were, there would never be a teambuilding event that falls flat. 

What you actually want is to create a space for your team to move the needle on employee satisfaction/enjoyment of the workplace. If you’re going to spend money, would you rather it have an ROI on employee engagement or not? Increasing employee engagement means decreasing the work-related headaches that send people home complaining to their spouses about their work. The silent killer of teams and what has people switch is when they’re not seen, heard, or valued or when trust is absent. 

But more on creating trust later…

The common mistake most people make is bringing people together “in order to to bring them together”, aka without a clear purpose. And the second most common mistake most people make is bringing people together with the simple objective of having fun.


Many times I see people gathering with the intention:

  • We want to bring people together

  • We want to have our yearly get together for the team

  • We want to have fun together


But none of these are actual objectives. They are the forms of the gathering (a get together), and the reason why the get together is happening is to get together. Do you see the irony of creating an event to bring people together? As Priya Parker states in the Art of Gathering, “plan your next gathering when you have a specific, unique, disputable purpose that helps you make decisions about how the event should unfold.”  When your purpose is a category, “To get out of the office together in a different context,” there is not a purpose. A basic, boring purpose (but at least you’re trying) is something like “To focus on the year ahead” while having a specific, unique, and disputable, its something like “To revisit why we’re doing what we’re doing and reach agreement about it” or “to focus on the fractured relationship between sales and marketing, which is hurting everything else.” Make your objectives pop if you really want a stellar event.

Step 2: Figure out what the team is challenged by, and design the offsite around ameliorating that challenge. 

It helps in making a polarizing purpose to actually address team issues. Would you want to make an investment just for fun or to address team challenges? This also aligns directly with making your events generate a higher ROI.


Step 3: Create the environment for the team to develop self-awareness for group dynamics at play and communicate around it.

Have productive and honest conversations with all pertinent parties about what’s not working so that each person feels heard, valued and understood.

At the end of the day, I’m reminded of Hans Christian Anderson’s story of the Princess and the Pea. The Queen puts a pea under the mattress and then puts 20 mattresses and 20 feather beds on top. Imagine these mattresses are all of the communication challenges and falsities, judgments, or communication misunderstandings we have with one another. The Princess couldn’t sleep a wink, because the pea was still beneath the mattresses. It’s a story that tells us that it’s still going to be there–the challenges are always going to be there, preventing the princess from sleeping or from the team from reaching optimum high performance, until we address them. 

Step 4: Create a shared memorable experience, steeped in having fun together while building meaningful work relationships.

Having a memorable shared experience should be designed to further connection, while being enjoyable, expansive, and nurturing to the soul (an experience that naturally produces serotonin and oxytocin; this is what happens for example when people experience an awe-inspiring moment together or connect in a deeper conversation).

Your goal with these memorable shared experiences is to create neurochemicals in the brain that make people like each other and have positive emotions towards one another.

Step 5: Create the context for you to solve your challenges & build consensus. Once enhanced team trust and psychological safety have been established, the team goes to work on an aligned deliverable.

Co-create an aligned deliverable and navigate the first stumble together in a new (and better) way. Introduce a fresh approach to handling future conflicts, one that is both productive and fosters repair while ensuring everyone feels heard. This method promotes a healthy resolution to conflicts, leaving all involved with a positive experience.

Here’s the breakdown of how you create Meaningful Work Relationships:

Focusing on enhancing these inputs is what gets you the 20% increase in employee engagement & increase in team cohesion. A lot of that rests on the ability to have honest conversations with one another and call each other out. 


A Note on High-performing teams:

High-performing teams share several key characteristics that contribute to their success. Here are the top five characteristics of high-performing teams:

  1. Clear Goals and Objectives: High-performing teams have a shared understanding of their goals, objectives, and priorities. They know what they are working towards and why it matters, which helps them stay focused and aligned in their efforts.

  2. Effective Communication: Open, transparent, and frequent communication is crucial for high-performing teams. Team members communicate clearly, listen actively, share ideas and feedback constructively, and collaborate seamlessly to achieve common goals.

  3. Strong Collaboration: Collaboration is at the core of high-performing teams. They work together synergistically, leveraging each other's strengths, skills, and perspectives to solve problems, make decisions, and achieve superior results.

  4. Accountability and Responsibility: Members of high-performing teams take ownership of their work, responsibilities, and outcomes. They hold themselves and each other accountable for meeting deadlines, delivering quality work, and achieving shared objectives.

  5. Continuous Learning and Improvement: High-performing teams have a growth mindset and a commitment to continuous learning and improvement. They adapt to changes, embrace challenges as opportunities to grow, seek feedback, and proactively identify ways to enhance their performance and results.

By embodying these characteristics, high-performing teams can achieve exceptional results, foster innovation, and maintain a positive and productive work environment.

Important components for offsites or events for high-performing teams to get them to perform even higher.  Focus on:

  1. Trust & transparency 

    1. “I’m giving you these comments because I have high expectations and I’m confident you can reach them,” Adam Grant says is hugely beneficial instead of just giving feedback without the trust that the person can rise to the occaision. 

  2. Connection

    1. Relationships are built on shared experiences, so let’s create more of that. 

  3. A novel experience to shift things

    1. People resist the “same old, same old.”

  4. Opportunities for learning to be self-aware and build self-awareness in order to gut-check the knee jerk reactions.

Meaningful Work Relationship Research also tells us to connect with one another over your individuality, not over your similarities. Rather, get to know and understand and appreciate the dynamic interests that encompass your team.


Acclaimed thought leader on high-performing teams, Patrick Lencioni, identified the 5 dysfunctions of a team. Before an offsite, we use surveys and snowball sampling to identify which of the 5 dysfunctions of a team is most important for your team, and then design exercises around ameliorating these issues. 


Lencioni’s Five Dysfunctions of a Team Are:

  1. Absence of Trust

  2. Fear of Conflict

  3. Lack of Commitment

  4. Avoidance of Accountability

  5. Inattention to Results

Patrick Lenconi’s Five Dysfunctions of a Team

There are a few steps that you need to take to ensure you have a deep sense of trust on your team, which we broke down in a list.

Here are the top five ways to build trust on a team:

  1. Lead by Example: Trust starts at the top. Leaders must demonstrate trustworthiness through their actions, integrity, and consistency. Be transparent, honest, and reliable in your interactions with team members. There are many facilitated activities that can have this occur during the offsite.

  2. Communication and Transparency: Foster open and transparent communication within the team. Share information, updates, and decisions openly, and encourage team members to voice their opinions, concerns, and ideas without fear of judgment. Good facilitators will prompt these and create the container for safety so that people can be honest with one another in an offsite.

  3. Accountability: Hold everyone accountable for their actions, commitments, and responsibilities. When team members follow through on their promises and deliver results, it builds trust among the team. Address any issues or mistakes promptly and constructively. Moments in offsites, one can learn communication tools and then implement them.

  4. Empathy and Respect: Show empathy and respect towards team members' perspectives, feelings, and experiences. Listen actively, be understanding, and avoid making assumptions or judgments. Recognize and appreciate everyone's contributions and strengths.

  5. Consistency and Reliability: Be consistent and reliable in your words and actions. Honor commitments, meet deadlines, and follow through on promises. Consistency builds credibility and reliability, which are essential for earning and maintaining trust.

By focusing on these five strategies, teams can create a culture of trust that fosters collaboration, innovation, and high performance.


Case Studies

Below is a list of various case studies Executive Offsites has facilitated so you can see examples of problems and how they were solved. As you’ll notice, nearly all of these challenges were solved with a similar underlying component of enabling the teams to humanize one another. 

What actually happens during an offsite?

  1. Clean up communication in order to foster team trust

    1. Productive and honest conversations with all pertinent parties about what’s not working so that each person feels heard, valued and understood

    2. The #1 mistake we see clients make is not taking advantage of the in-person time together to clean up communication practices. We spend so much time with those that we work with; it’s important to foster communication where each person feels heard and valued, and that often gets lost in the shuffle without intentional time set aside.

    3. Foster an environment of transparency and integrate that into the culture. You think that you can still have success without effective team communication or trust. But the truth is, you’ll have turnover or dissatisfied people who are not invested in your company.  Better satisfaction with the team comes from team trust.

2. Natural serotonin and oxytocin releases that create intentional fun while deepening human connection

    1. A memorable shared experience that furthers the connection, while being enjoyable, expansive, and nurturing to the soul (an experience that naturally produces seratonin and oxytocin; this is what happens for example when a shared awe-inspiring moment or a connected conversation happens)

    2. Have intentional fun designed to help the team operate more effectively.  Common mistakes we see clients make is trying to just have fun and not ground the fun in any learning for the company or spending too much time on stuff that there is not enough time for the joy.  Connecting outside the ordinary constraints of the workplace creates a different relationship, including a sense of belonging with the team &  a reinvigoration for one’s work.

    3. Current teambuilding efforts are failing to create real, deep human connection. They connect surface level. You may even create offsites with tight agendas with a clear goal where you are productive, but you still lack in the fundamental connection. The problem that teams face is communicating effectively to support growth, trust, being able to hold one another accountable, and team cohesion in decision-making.  We solve for that.

    4. Invest in a genuinely amazing experience & personal growth opportunities. An experience that people look forward to or look back on and feel reinvigorated is an investment in themselves.  Why create something that is “meh” when something that is genuinely fun, feels like a gift or retreat, and is off-the-charts amazing, will do?

      3. Navigating through the first conflict & creating an aligned deliverable

      Co-create aligned deliverable and navigate the first stumble together newly. A new experience in navigating the next conflict. A productive way to move through conflict that repairs and makes everyone feel heard/a healthy way to move through conflict that has everyone feel positive about the experience.

How to structure the day:

You want to vary the activities to keep people engaged and mix it up. Vary the location (we try to keep as many activities outside as possible).  In addition, we alternate between intellectually stimulating and then fun or connected activities. We go back and forth between “fun” and “head-centered” activities in order to keep things interesting and keep people engaged. 

Below you can see some sample itineraries:


Sample Itineraries:

A: Just an afternoon itinerary

Afternoon Itinerary:

  • Welcome

  • Fostering Collaboration

    • Experiential Activity

    • Debrief of Activity: How does this relate to how we work?

  • Connecting beyond the surface:

    • Personal History Exercise

  • Getting to Know Each other:

    • Conversation Circles

  • Building Trust

    • Values and debrief of values. Charting it, and then identifying group values.

    • Asking for help, not offering it: Build trust by asking for help not offering it

B: Multiple Day Itinerary:

Day 1:

10am-6:30pm:

  • Connecting beyond the surface:

    • Storytelling exercise with "Where do we begin?" and/or We Connect

    • Listening exercise: feedback giver, feedback receiver, observer; Practice listening and not being reactionary

    • Coaching training

  • Differentiation of Self vs. Team

    • Understand your own perspective & trust your gut

    • Hunter vs. protector vs. prey exercise

  • Understanding team dynamics:

    • Values exercise to understand your values vs. team values

    • Hub & Spoke: understanding your purpose vs. team purpose

  • End of Day Debrief

6:30pm: Dinner

8pm-9pm: Stargazing

Day 2 & 3: roadmapping with heads of organizations

Day 2 Activities: 3 Hours

Morning: Visioning exercise to aid in preparation for day 

Afternoon: Fun team activity outside 

End of Day Debrief 

8pm-9pm: Team Campfire: what letting go of & what crystalizing?

Day 3 Activities: 3.5 HOURS

Morning: Game (Hot Ones with Leadership) 

Journaling & playbook creation for how to interact going forward 

Coaching session 

Afternoon: End of Day Debrief


A week-long itinerary:

Conclusion:

Our system of work is set up for dehumanization. We have to actively work to humanize one another in order to have more fulfilling experiences at work and more meaningful work relationships. 

How we dehumanize each other in the workplace or turn colleagues into mercenaries:

Here are the top five common ways that dehumanization occurs in corporate America:

  • Treating employees as replaceable commodities.

  • Micromanagement and lack of autonomy.

  • Overemphasis on productivity over employee well-being.

  • Inadequate communication and transparency.

  • Ignoring employee feedback and input

  • Lack of empathy for personal challenges.

Addressing these issues requires promoting autonomy, fostering a healthy work-life balance, improving communication, valuing employee input and well-being, and cultivating empathy within the workplace culture.

What if the point of offsites was literally to invest in humanizing each other and employees? 

Just like IT brought sexy back, we’re bringing humanity back…back to the company. We are humanizing each other. Why is that beneficial?  Cause I’ve seen time and again how much feedback lands when it’s delivered by looking someone in the eye, and how much deeper that lands than sending an anonymous feedback into the either. But my take on 360 degree feedback for another day. 

The point is that given how much companies dehumanize one another and turn employees into replaceable mercenaries, I argue that offsites should be a humanizing experience; they should make every effort to create meaningful work relationships. People don’t leave places that they love and have deep friendships, feel valued and heard….period…end of story.