Intro

Rob: Let's get started. Could you introduce yourself and give a brief overview of your work experience?

Mat: Sure, I'm Mathew Caldwell. I've been in the HR and talent space since '97. I started my first company that year. It was an exciting time, especially during the .com era. I experienced both failures and successes. After that, I led a few small consulting companies before taking an in-house role at an early unicorn startup. I was responsible for HR there, in one of the first billion-dollar valued startups. Then I moved to Mozilla as a global leader, helping with strategy and opening operations worldwide. This included a focus on talent strategy, including navigating a  significant shift from what they historically focused on to an entirely new mission and talent profile. After Mozilla, I joined Instacart as their first head of people. I was Employee 51 and helped lay the foundation for their recruitment and hiring strategies, covering both “knowledge workers” and those delivering groceries. Following Instacart, I founded Rocket Power about seven years ago. It was a culmination of all my experiences, a recruiting consulting company offering more than just recruitment. We also provided engineers internationally for companies on an outsourced basis, focusing on building teams globally. RocketPower was my most successful venture, growing to 400 employees worldwide. Despite the challenges and learning experiences, it was incredibly rewarding. Currently, I'm enjoying life after selling the company, doing some volunteer work, and exploring what’s next.

Building Teams

Rob: Thanks for sharing, Mat. Given your extensive experience in job placement and team building, what do you think is crucial when searching for people that fit a specific culture? It's not just about credentials, but also about values, sociability, and how they work with others. How do you evaluate these aspects to find the right fit?

Mat: Absolutely, it starts with understanding your own culture. Successful companies usually have a well-defined culture. Culture is organic, like planting a cherry seed; you know you'll get a cherry tree. It's shaped by the people you bring in early, but you can also nurture and strengthen it. Recognizing your culture and having clear values helps in identifying people who can fit and function within those principles. Knowing your team's strengths and weaknesses is vital to hire people who complement and enhance your culture.

Steve Jobs once said he preferred having a few 'A players' over a hundred 'B players'. It's about surrounding yourself with people you respect, can learn from, and who bring diverse perspectives. A team of people who are not only smart but also humble and open to learning is incredibly powerful. That’s the key to building a successful team and company.

Rob: You've obviously had significant experience in building large teams at Rocket Power, reaching up to 400 people across various cultures and boundaries. That's quite an achievement. When it comes to team building, what would you say is the most important cultural principle you tried to instill in your workforce there?

Mat: Building a strong team culture is a complex task. I think one key aspect is humility, but it's often misunderstood. Humility doesn't mean being meek or easily pushed around. It's about being humble yet driven and hungry for success. If you're not humble, you risk being uncooperative and inflexible, which can be detrimental to a team's success. Humble team members are open to learning, adapting, and placing the team's or client's needs above their own need to be right.

Humility

Rob: So, it's about fostering a culture of humility coupled with drive and competitive spirit.

Mat: Precisely. It's creating an environment where people are comfortable being wrong, learning from it, and working collaboratively towards common goals.

Rob: So, saying humility is important is one thing, but how do you actually instill that in people?

Mat: Instilling humility is challenging. It's something you need to look for during the interview process. It's hard to teach; it's not like teaching intellectual skills or systems. Employees generally need to come with a sense of humility, though they can improve on it. Encouraging humility involves demonstrating it yourself as a leader. In my role at Rocket Power, I often had to listen more than speak, even when I was the expert in the room. By doing that, by giving others the space to challenge and correct me, I encouraged a culture where people felt comfortable showing their humility.

Within our leadership team, we had heated discussions, functioning more like brothers than colleagues. Sometimes, I had to stop talking and let others speak, which allowed them to express themselves freely. At quarterly meetings, we openly talked about our failures and mistakes, treating everyone as equals, not just as employees. This approach fostered an environment where people at all levels felt comfortable being themselves and showing humility.

However, it's not just about modeling humility. Sometimes, you have to be direct with people who lack humility, especially when they're being inappropriate or disrespectful. It's important to call out these behaviors and remind people that it's okay to be wrong. You can't just model humility; you also have to actively manage and encourage it within your organization.

Rob: It seems that the closeness of your personal relationships with team members influences the intensity of your interactions. Like with your executive team, you’re friends outside of work, which allows for more intense discussions. Would you say that the closeness of the relationship dictates the level of communication intensity?

Mat: Yes, that's often the case. It's not necessarily right or wrong; it's just what happens. I'm usually the one who gets most heated in discussions, especially with one team member who often challenges me. My natural intensity sometimes comes across in these debates. I've had to apologize on multiple occasions and take people aside to resolve things. For instance, during one heated discussion, a colleague pointed out I was acting paternalistic. It reminded me of how my dad and I used to debate. Respectful debate is essential, but it’s different when it's just about challenging without a solid point.

My dad once used an analogy about relationships being like gears in a clock. Some relationships are like casual greetings where major life events don’t affect the interaction much. Then there are relationships akin to a fine Swiss watch, where even the smallest issue can cause significant disruption. Close relationships can be heated over minor things, but they also allow for more forgiveness and vulnerability. This is because, with closer relationships, we are more willing to share and be open, even when we feel insecure. Sometimes, especially when you're not sure of the environment or the people around, you might hesitate to share something, worrying that it might come across as dumb. It's a different dynamic when you're in a close relationship where you feel more comfortable being open and vulnerable.

Rob: That reluctance to share, it's really about pride, isn't it? A lack of humility.

Mat: Yeah, it is. We all experience it in different situations. Just yesterday, I was discussing something and hesitated to ask questions because I didn't want to reveal my lack of knowledge about the situation. That's a form of pride. But when you're close to someone, you don't have that problem. You feel comfortable saying, 'Wait, I don't understand, tell me more.' Close relationships foster creativity and the ability to approach problems from various perspectives. They allow you to overcome things without being held back by insecurities. If everyone's too afraid to speak their mind, how can you solve a problem effectively? The best solutions often lie hidden beneath those insecurities.

Rob: Sometimes I catch myself experiencing what I call 'man pride,' where pride starts influencing my decisions. I've trained myself to recognize this as a warning sign to avoid making decisions based on pride. Instead, I consciously step back from decision-making in those moments to avoid feeding into that mentality. Do you relate to that?

Mat: I understand exactly what you mean. In meetings, I often speak first, even if it means being wrong. When I realize I don't know something or someone points out an error, I'm quick to acknowledge it and apologize. It's about placing yourself in a position to be corrected, having the courage to admit you don't have all the information but still willing to move forward with a decision.

Rob: Right, it's about humility in accepting that you might be wrong.

Mat: Exactly. There are times I choose to remain silent, even if I'm knowledgeable on the subject, to give room for others to speak and learn. It's important in a group setting to create space for different voices. Sometimes, you need to be the one to break the ice, even if it means your idea might not be the best one. This approach helps get the discussion flowing and opens up the floor for more informed contributions. It's about getting past the fear of being wrong and fostering an environment where everyone feels comfortable contributing, even if it means being corrected.

Rob: That makes a lot of sense. Encouraging open communication and admitting when we're wrong can really drive progress in a team.

Family Influence

Rob: Let's take a step back in time. Your appreciation of humility – what has influenced that in your earlier life?

Mat: There are a couple of influences. Both of my parents, actually. My dad especially had a significant impact.

Rob: I'd imagine he's a humble man.

Mat: He is, and so is my mom; she might actually be the smarter of the two. But they're both incredibly intelligent people. My dad was studying to be a doctor at Berkeley when he decided to change his path. He started a janitorial business instead. I remember shadowing him as a child, seeing how he interacted with people at the offices his company cleaned. Even though he was often looked down upon for being a janitor, he always responded with humility. It was an eye-opening experience for me, seeing the difference in how he was treated versus the success and respect he actually deserved.

Another thing I learned from him was the importance of apologizing. We're quite similar, so we'd get into arguments, but he would always apologize sincerely when he was wrong. That taught me a lot about being a man – the ability to admit mistakes and apologize, even to someone less experienced or younger, like a son. He also demonstrated contentment, choosing not to expand his business further to maintain a balance with family life. He made sure to prioritize what truly mattered, setting a great example for me.

My dad's approach to his business was closely tied to his humility. He had several opportunities to significantly expand his business. One notable chance was to take over all facility operations for Safeway, spanning from Colorado to Hawaii. It would have been a huge expansion. He seriously considered it, but ultimately, he decided against it. His reasoning was straightforward yet profound: yes, we would have made much more money, but it would have cost him time with his family. He chose to be present, to be involved in our lives. That decision, to me, epitomized true humility. He prioritized us over the potential for greater wealth, something not many would do.

Rob: That's a remarkable choice.

Mat: It really was. Three things stand out to me about my dad. First, his willingness to be in a position where people often talked down to him, despite being intellectually superior. He never retaliated in kind. Second, he was always ready to apologize when wrong, which taught me a lot about humility and respect. And finally, he deliberately built his business to a size that allowed him to support our family comfortably but without compromising on what he valued the most – spending time with us, his family. That balance he struck between work and family life, that's something that deeply influenced my views on what's truly important.

My mom was a housewife and didn't work outside, but she's a very intelligent person. She always showed immense respect to my dad. There were times when she probably processed things quicker than him, yet she chose to support his decisions. This family dynamic taught me a lot about respect and humility—being respectful to someone regardless of their intellectual level.

They had disagreements, like any couple, but they rarely fought in front of us. Watching their dynamic, where intelligence wasn't used as a tool for one-upmanship, was enlightening. My mom was also incredibly giving and helpful. She was always the one making food for someone sick, going grocery shopping for those in need, or helping others in the community. I remember accompanying her to help an elderly lady regularly, bringing groceries and helping around her house. These acts of kindness weren't just duties to her; they were genuine gestures of helping those in need. Seeing my mom's humility and her willingness to help others without expecting anything in return was a powerful lesson for me.

Rob: It seems like both your parents were great examples of humility in action.

Mat: Absolutely. Their examples, in different ways, really shaped my understanding of humility and respect.

Effective Company Structure

Rob: I've been thinking about how in the startup world, micromanagement is virtually impossible due to the workload and the small size of teams. It forces an environment of trust, even if there's initial doubt. As companies grow, however, there's a shift towards more structured management that can slow things down. I wonder if a more familial, patriarchal approach, where smaller units work closely like family, might be more effective. What's your take on this?

Mat: You're right about the transition from startups to larger companies. In startups, it's all about trust and autonomy because you just can't micromanage. When companies grow, they often become overly structured. Too many layers of management can stifle the original dynamic. As for your point about a patriarchal system, it's interesting. While 'patriarchal' might not be the right term due to its connotations, the concept of smaller, cohesive units or teams within a larger organization does hold value.

In the software engineering world, for instance, they have 'pizza teams'—small, agile groups capable of functioning independently while still aligning with the company's broader goals. These teams are more like pods within the organization, each with a specific focus, whether it's on a particular app feature or a product aspect. Everyone has a clear role, but there's a collective responsibility for delivery. This setup maintains the agility and trust of a startup environment within a larger organizational structure.

Rob: So, it's about maintaining that startup-like agility and autonomy even as the company grows.

Mat: Exactly. It's about finding the right balance between autonomy and structure, ensuring that teams have the freedom to work effectively without unnecessary oversight.

You're making me think about how this idea could be applied in a large company.

Rob: But it seems challenging to get traditional corporate companies to adopt such a model, doesn't it?

Mat: It is challenging because changing an established system is hard. It's threatening to some employees, especially if their roles don't add much value. When you start restructuring to focus on value-adding roles, people get anxious.

Rob: I've noticed that jobs focused on assessing value often don't add much value themselves. Roles designed to ensure a department's efficiency might and often actually contribute to inefficiency.

Mat: Exactly. Often, the inefficiency lies in having too many people monitoring rather than doing. What's needed is better training for department leaders or hiring more effective leaders.

Rob: Right, so it's about empowering leaders within their own teams.

Mat: Absolutely. Rapid growth can make it difficult to have the right leaders in place. Every team, or 'pod,' needs a leader, someone like a scrum master to keep things on track.

Rob: That makes sense.

Mat: Implementing this from the early stages is key, as Apple has demonstrated. Trying to introduce such a model in a company like HP, which is already set in its ways, would be much harder.

Rob: So, adapting this model in an established corporate environment poses significant challenges.

Mat: Yes, it's a complex task requiring thoughtful implementation.

Rob: That approach reminds me of what Steve Jobs did when he returned to Apple. But it required an enigmatic leader and a company on the brink of bankruptcy to really make it work.

Mat: Yes, Jobs managed to do that, but it was very much about who he was as a leader and the specific circumstances Apple was in at the time.

Rob: Right, it seems like implementing such changes in a company that's currently successful and stable might not be as feasible.

Mat: Exactly. When a company is just cruising along, making steady returns on investment and satisfying shareholders, it's hard to motivate them to undertake major changes. They're comfortable with the status quo, and there's little incentive to disrupt that, especially for the sake of a management model that requires a significant shift in corporate culture and structure.

Rob: Yeah, that's a real challenge.

Mat: It's about weighing the risks and rewards. Radical changes like these are often easier to implement in times of crisis or major transition, not when a company is performing adequately by conventional standards.

Last Words

Rob: Awesome. Ok for my final question, what advice would you give to an aspiring product owner, product manager, or team manager? Something you wish you had known when you started.

Mat: Looking back, I wish I had a clearer understanding of my strengths and weaknesses. It's crucial to be honest with yourself about what you're really good at and where you fall short. Sometimes, we think we're strong in areas where we're not, and that can be risky. It's helpful to seek feedback from trusted individuals who can give you an honest assessment of your strengths and weaknesses.

Another thing I struggled with early on was letting go of control, especially as a founder. You want to oversee everything, but that can hinder your team's success. Knowing when to delegate and trust your team is essential. It frees you up to focus on what leaders should be doing: being creative, shaping culture, and being a visionary.

Also, be willing to make tough decisions about your team. As a people person, I sometimes held onto employees because I believed in their potential. However, in a startup, you need people who can perform immediately. Holding on to underperforming staff can send the wrong message and drag the team down. Learning when to let people go is as important as knowing when to bring them on board.

Rob: Always a pleasure, Mat. Thanks for your time.

Takeaways 

In closing, Mathew Caldwell's extensive experience in HR and talent management offers invaluable lessons:

1. The Power of Humility in Team Dynamics: Caldwell emphasizes the critical role of humility in building successful teams. It's not about being meek but about being open to learning, adapting, and prioritizing collective goals over personal ego. This approach fosters a collaborative environment where diverse and driven individuals contribute effectively.

2. Balancing Control with Trust in Leadership: For leaders, especially founders, Caldwell highlights the importance of balancing control with trust. Letting go and trusting your team can be challenging but is essential for fostering creativity, innovation, and efficiency. Leaders should focus on their strengths and delegate appropriately to empower their teams.

3. Understanding and Leveraging Personal Strengths and Weaknesses: Recognizing and being honest about one's strengths and weaknesses is crucial for personal growth and effective team building. Leaders should seek feedback and be willing to complement their weaknesses by surrounding themselves with diverse and skilled team members. This approach leads to well-rounded and resilient teams capable of facing various challenges.

More from Mathew Caldwell

• Mathew Caldwell on LinkedIn