Sometimes, it’s the smallest things that make the biggest impact. 

It’s hard to remember what happened at the start of the pandemic in 2020, but I can tell you one thing: we were all stressed out. It was an absolute mess, and no one knew how to navigate it. 

I’m lucky to have a strong community of friends and family to help me cope with the mental load of my first pandemic. One moment that stood out to me was when my friend, former boss, and colleague Daniel Incandela reached out. It wasn’t unusual to hear from him, but our communication was usually text (with a few emojis sprinkled). 

He was simply checking in to see how I was doing. The call lasted no more than five minutes, but the impact was long-lasting. It was just a moment of human connection when I needed it the most. 

As we finish our Thanksgiving weekend (here in the States), it’s a good reminder that sometimes, it’s not the big acts but the quick, thoughtful check-ins that have the biggest impact. Before you read the rest of this email, take a moment to reach out to show you care and finish the weekend off right. 

And remember one of my favorite Kurt Vonnegut quotes: When things are going sweetly and peacefully, please pause a moment, and then say out loud: "If this isn't nice, what is?"

❤️ kyle

On Crafting Cool Direct Mail

This past Monday marked one of my favorite days of the quarter: Swag Drop Day.

If you know me, you know I’m a huge fan of creative direct mail and encouraging teams to embrace a bit of illogical thinking. Remember last week’s newsletter quote from Rory Sutherland?

With that in mind, we challenged the team to think outside the box. I made it a point to say no t-shirts and no typical end-of-year gifts. Instead, we asked: What if we designed and produced a game?

There were just a few guidelines:

• Create something that ties back to what we do at Jellyfish (directionally) 

• Surprise and delight our prospects, customers, and internal team.

• Make it reusable beyond the holiday season.

Needless to say, the team absolutely crushed it.

So, how did we do it?

1. Bring in diverse perspectives: We held a brainstorm session during an onsite planning meeting and invited not just the marketing team, but anyone across the company interested in game design. We blocked out two hours, sent out a Slack invite, and got to work. No rules just creative output.

2. Test and refine: The team generated four game ideas during the brainstorm. We voted on the top two, built MVP versions, and tested them internally to see what resonated most.

3. Design and produce: This step is no small feat. Finding the right vendor (we recommend ScreenBroidery) and having a strong creative team is crucial. We’re fortunate to have amazing in-house talent at Jellyfish, but if you’re looking for external support, I highly recommend d.

And that’s how a little creativity turned into something truly unique (if not adapted from Cards Against Humanity). Swag Drop Day isn’t just about giveaways; it’s about pushing boundaries and creating memorable experiences.

On Asking the Right Questions in an Interview 

Are you currently interviewing? Searching for your next role? 

It’s highly likely you might be focusing on the wrong thing. Interviews aren’t just about preparing to answer questions—you also need to bring thoughtful, strategic questions to ask your interviewer.

To be completely honest,  I like to kick off interviews by asking candidates if they have any questions for me. Why? It’s a quick way to gauge whether they’ve done their homework on the role and company, and it offers insight into their strategic thinking.

Okay, let’s be helpful. I’ve outlined six must-ask questions that  into emotional intelligence, growth mindset, and professional development. Plus, I’ve included what to look for: 🟥 to watch out for and 🟩 to celebrate because… yay!

Emotional Intelligence

Emotional intelligence is key to understanding a company’s culture and determining how you (potentially) fit. It's also the foundation for building a positive relationship with your manager and team. The right questions can help you gauge how the company approaches communication, conflict resolution, and feedback, offering a clear sense of working there.

Here are a couple of examples 

How do you handle conflict or disagreement?

🟥 They downplay the importance of conflict or insist it rarely happens without providing a clear example. This is an excellent example of avoidance and not constructive to your career (trust me). 

🟩 They give a concrete example of addressing conflict and encouraging open communication. This will give you insight into how disagreements are managed within the company and if the environment supports respectful dialogue.

Tell me about when you (or the leadership team) had to navigate difficult decisions.

🟥 They provide vague answers or blame someone else, suggesting a lack of transparency or lack of desire to confront challenges directly. No way. 

🟩 They share a specific example where the decision-making process involved clear communication, stakeholder input, and a thoughtful evaluation of options, highlighting their leadership under pressure.

Growth Acumen

We move fast in software, and a company’s ability to scale effectively can make or break its success. Understanding the leadership team’s experience with and approach to scaling is critical. Their insights into growth strategy and decision-making processes will give you a good idea of whether they can grow. 

Can you provide an example of key metrics the company tracks and how they influence your decisions?

😡 They either fail to mention metrics or refer to vanity metrics (social media likes) without linking them to meaningful business goals. This usually means they have a lack of focus on data-driven decision-making.

💚 They share actionable metrics, such as customer acquisition cost (CAC), churn rate, or net promoter score (NPS), and explain how these drive strategic decisions, signaling strong alignment with business goals.

How do you balance short-term performance with long-term goals?

😡 They emphasize one at the expense of the other, such as focusing solely on hitting immediate targets without considering long-term planning at the cost of short-term wins.

💚 They describe a balanced approach, such as prioritizing quick wins that align with longer-term goals, while maintaining a clear vision for long-term scalability.

Community Development & Professional Development

The last thing you want to do at your new job is just focus on your work and ignore building relationships and making new connections. Good leaders know it’s important to be involved with the outside world and help their team build a strong network for the future.

A great leadership team doesn’t just care about the company—they also work with others outside the company and help their team make important connections. Understanding how they do this can show you how much they care about helping you grow and succeed.

How do you stay connected with the broader industry?

🥵 They might give a vague answer, like saying they're too busy to be involved in the industry. This could mean they aren't really staying up-to-date or showing leadership in their field.

🍏 They talk about joining industry events, speaking at conferences, or being active in professional groups, showing they care about staying informed and making a difference in their field.

Can you share examples of how you have introduced team members to your network? How did you help them develop their own professional network?

🟥 They avoid answering the question or say they don’t think networking is important for the team. This might mean they don’t offer much help or guidance to help people grow in their careers.

🟩 They give clear examples, like introducing team members to important people in the industry, encouraging everyone to go to conferences, or helping employees learn how to build their own networks. This shows they really care about helping their team grow and succeed.

Asking the right questions isn’t just about getting the job; it’s about finding a career that matches what’s important to you and your goals. When you ask about things like how the company handles teamwork, how they help people grow, and how they plan for the future, it shows you’re thinking ahead. It also helps make sure your next job helps you get better at what you do, so you’re not just relying on your resume.

On a Six-Year-Old, Chess, and a Lesson in Excellence

One of the more important lessons I’ve learned when striving for excellence as an individual, a father, and a leader is that we all approach the path to excellence differently. I learned that lesson from my then-six-year-old, Caden. 

My son, Caden, is fascinated with chess. He loves the strategy behind the game, but his love for chess was a hard-fought battle. We’ve played every week for the past couple of months. And I’m lucky enough to say he taught me the importance of striving for excellence through chess.

Before we get into the details, you must understand that Caden is a serious kid. He’s exceptionally competitive but easily gives up when something is hard. It sounds like every six-year-old out there, right? It’s an interesting dynamic to experience as a parent. Mostly because I don’t want him to give up too quickly. I want him to have fun, but I also want to build resilience. I want to push him hard, but not too hard.

I’ve read too many stories of highly successful people who had difficult childhoods. How do I instill the complex work values of Rockefeller without the unhappiness? How do I teach him to become a chess master without the headaches? It’s an age-old parental conundrum. How hard do you push your child?

OK, back to Caden’s Gambit.

Sometimes, Caden decides to stop playing, runs away pouting, or knocks over pieces because I’m winning or coming for his queen. Again, a completely normal six-year-old reaction.

I first scolded him, “Caden, it’s just a game. You need to be a good sport. You’ll only get better if you continue to play.” The scolding rarely works. He refuses to play, and we both leave frustrated because he’s six, and I’m a child in a man’s body.

This “storming” kept happening week after week—until I decided to switch up tactics. This is mainly due to my reading of Ryan Holiday’s Daily Stoic, in which he quotes Marcus Aurelius:

I needed to calm my mind to help Caden relax. It’s natural to become angry or scold; it’s human nature. It might make me feel better, but does it solve the problem? It wasn’t my son’s fault. He wants to learn how to play and win while doing it. I can’t fault him for having the competitive Lacy gene.

So, I switched it up. “I understand you’re upset. Let’s start over. Do you want to start from the beginning, and I can explain the moves?” He reacts differently now. He doesn’t storm off. He agrees and finishes full games as I coach him through different moves. He just wanted a second chance.

Caden demonstrated two very different reactions, both from a place of striving for excellence. He wanted to win. He wanted to learn. He tried to succeed. But I had to learn how to push and encourage him helpfully and without being reactionary.

Now he’s excited to play and gets better every time we sit at the board.

All that to say, this same concept applies to our work. We must strive for excellence as individuals and as a team by recognizing that we all approach the path to excellence differently. But how do we fully understand each path?

1. Use a guide to understand the way we work and live. Use a personality profile like DiSC or CliftonStrengths to give you a common language your teams can use to understand better themselves and those they interact with. Most personality tests have a guide, but you can also hire a consultant to guide you through the process.

2. Read The Five Dysfunctions of a Team (again). There is no better book to learn how to build trust and efficiency within a team than Lencioni’s masterpiece. Read the book as a team and discuss the five steps to building trust, vulnerability, and teamwork.

3. Host a life story meeting. This is one of my favorite tactics for building trust within a team. Ask each of your direct reports to make a life story slide detailing their personal and professional triumphs and challenges. Give each teammate 15 minutes to talk through their slides. Encourage the team to be vulnerable, which will ultimately build trust.

4. Personalize the path. Everyone approaches work and their path to excellence differently and sets goals accordingly. For example, individuals with a high D (DiSC) will care more about bottom-line results than a high I who may favor relationship building.

Ultimately, it is about building trust. Trust is foundational to a team that holds each other accountable in their pursuit of excellence. Personal goals matter, but what’s far more critical is how we strive for excellence and support those around us in their pursuit of excellence.

So, the next time you are close to anger or frustration with a co-worker, calm your mind before you respond.

This excerpt was originally published on Fast Company in 2022.