Leading Like a Type Two: How Unreasonable Hospitality Creates Connected Teams

Most workplaces talk about culture, leadership, and team dynamics—but what if the key to building a thriving team wasn’t just about strategy and efficiency, but about hospitality?

That’s the gist of Unreasonable Hospitality by Will Guidara, a book that goes beyond just the restaurant industry. Guidara shares how small, thoughtful gestures can transform relationships, deepen trust, and create an environment where people feel valued and connected. And if that’s not a lesson straight from the Enneagram, I don’t know what is.

At Enneagram MBA, we work with teams and leaders to build more self-aware, emotionally intelligent workplaces—ones where people don’t just work together but thrive together. 

What Is Unreasonable Hospitality?

Unreasonable hospitality isn’t just about being nice—it’s about going beyond what’s expected to make people feel seen, supported, and appreciated. It’s about creating a culture where generosity and thoughtfulness aren’t just perks but part of how you do business.

Some leaders naturally lean into hospitality (hello, Type 2s, 9s, and even 7s), while others may need to be more intentional about it (looking at you, Type 5s and 8s). But the truth is, hospitality isn’t a personality trait—it’s a leadership skill.

Here’s how you can start using it in your leadership and team culture:

Anticipate Needs Before They’re Expressed (Like a Thoughtful Type 2)

One of the core themes in Unreasonable Hospitality is the idea of anticipation—not just responding to requests, but recognizing needs before they even come up. Type Twos are masters at truly seeing others and knowing how to connect with them.

In a workplace setting, this might look like:

• Checking in with a teammate before they hit burnout.
• Offering support before someone has to ask.
• Noticing when someone is overwhelmed and stepping in to help.
• Keeping track of teammates’ work anniversaries, birthdays, or even “firsts” (first client win, first month on the team, etc.) and celebrating them without being reminded.

Putting into Practice:
For the next week, challenge yourself to anticipate one unspoken need on your team each day. It could be as simple as bringing in their favorite coffee on the day of a big meeting or stressful week. 

Create “Surprise & Delight” Moments (Like a Fun-Loving Type 7)

We all love a good surprise (I hear even our Type 6s enjoy them every once in awhile :) ). But in leadership, the best surprises aren’t grand gestures—they’re thoughtful moments that make people feel valued.

At Eleven Madison Park, Guidara’s team once overheard a group of guests who had just returned from a food tour of New York—but had missed out on eating a classic NYC hot dog. By the time dessert arrived, they had arranged for a street vendor hot dog to be delivered, plated, and served at the table.

Now, obviously, we’re not running Michelin-starred restaurants. But the same principle applies to leadership: small, unexpected moments of thoughtfulness build trust and connection.

In a team setting, this could be:

• Sending a quick Slack message recognizing someone’s hard work.
• Bringing in someone's favorite snack or coffee (or sending a virtual gift card).
• Sending a personal thank-you note via snail mail. 
• Remembering their favorite TV show or movie and sending a funny meme in the group chat

Putting into Practice:
Think of one way you could surprise and delight one teammate this week. It doesn’t have to be big—just meaningful.

Make Hospitality a Habit (Like a Routine-Loving Type 1)

The best cultures don’t just leave hospitality up to chance—they bake it into their leadership and team processes.

How do you make generosity, appreciation, and connection part of how your team operates?

• Enneagram Check-Ins: Start meetings by asking how each Enneagram type prefers to be recognized or supported.
• Small Wins Fridays: End the week by sharing something positive about a coworker.
• Welcome Rituals: Make onboarding new employees more personal (handwritten note, team lunch, fun icebreaker)

Putting into Practice:
Look at your team’s daily or weekly routines. Where could you embed hospitality into your regular processes?

Bringing It All Together: A More Thoughtful Way to Lead

The best leaders aren’t just productive—they’re intentional about connecting with the people they lead.  And whether you’re a big-picture visionary (Type 8), a deep thinker (Type 5), or a networker (Type 3), you can use hospitality as a leadership tool to create collaborative teams and more engaged workplaces.

Your Mission (Should You Wish to Accept It...)

 This week, try one small act of unreasonable hospitality in your workplace. Anticipate a need. Surprise a teammate. Embed generosity into your leadership.

Because the best teams? They’re not just productive—they’re human, connected, and maybe even a little fun.

For more:

Want to create a workplace where this kind of culture isn’t just an idea, but a reality?

That’s exactly what we help teams do inside the Dream Team Certified Workplace™ program.

• Through custom workshops, team strategy sessions, and real-world application, we guide teams to:
• Understand their team dynamics & communication styles through the Enneagram.
• Build trust and collaboration by anticipating needs and reducing friction.Develop leaders who connect, motivate, and inspire their teams.
• Create an intentional culture where people thrive—not just work together.

Ready to shape a workplace culture that people actually want to be part of? Let’s start the conversation. Book a Team Strategy Call here.