My Life as a CTO - Trust Leadership

A leader is best when people barely know she exists, when her work is done, her aim fulfilled, they will say: we did it ourselves.

Every manager has a different leadership style. During my time at Facebook, I had at least five different managers, each with their unique way of leading. In a startup environment, where there isn't a uniform set of guidelines, a leader's style is even more dependent on their personal approach. After some reflection, I decided to name my own style 'Trust Leadership.' As the name implies, my leadership largely builds on the foundation of trust. For me, this is not only the most comfortable but also the most effective way to manage.

Before explaining what Trust Leadership is, although it's a bit embarrassing, I'd like to quote some feedback from team members as a reflection on my personal leadership style:

"Thank you for considering each team member's needs even amidst the pressures and demands of our work. I feel fortunate to be a part of your team."

"I am grateful to have you as my supervisor. You foster growth with trust as a basis, lead by example, and help remove obstacles for the team, all of which have been greatly beneficial to me!"

"Thank you for always being patient with me. Even when I make mistakes, you tirelessly communicate with me to identify the root of the problem and provide constructive advice, allowing me to genuinely solve issues and grow."

"I appreciate having a manager like you at this stage in my life. You've created a secure working environment and demonstrated how to lead a team and influence others. This has not only elevated my perspective but also given me the courage to make new attempts and the right choices."

"You are not only a leader who provides direction and shares with the team but also one who truly considers others' perspectives. I've always believed that a person's kindness and selfless contributions ripple outward, expanding ever wider."

"From losing confidence to regaining the courage to continue challenging life, it has all been because of your encouragement and support. You always give me excellent feedback during our 1:1s, teaching me the right ways and attitudes to face issues."

"I'm grateful that you were my manager. You will always be a role model for me."

Okay, enough of the goosebump-inducing moments. Let's talk about what Trust Leadership is.

What is Trust Leadership?

Trust Leadership is a leadership style that is fundamentally based on trust. Simply put, it means making all decisions, big or small, between managers and team members starting from a place of trust. The default choice is to trust.

Benefits of Trust Leadership

From my past experiences, Trust Leadership can bring significant benefits both practically and emotionally.

  • Practical Benefits

    Trust can greatly increase work efficiency. For example, when two strangers engage in a transaction, the lack of trust necessitates extensive preparations such as drafting contracts, specifying penalties for breach of contract, and setting definitive payment timelines. However, transactions between friends might only require a verbal promise, saving much hassle while achieving the same results. In the workplace, if a manager assigns a task to a team member without trust, many checkpoints might be set, meetings to confirm progress may be required, and progress reports might be demanded, consuming much time without necessarily improving outcomes. Trust serves as a tool that ensures commitments are met from verbal agreement to final result. Without using trust, various progress checks and additional processes are needed to double-check everything, which not only reduces efficiency but also demands a lot of extra effort.

  • Emotional Benefits

    Trust is a major motivator. When people feel trusted, they also feel the accompanying responsibility and the desire not to betray that trust. Trust and ownership often go hand in hand; for capable individuals, substantial ownership is one of their biggest motivators. Having their own space to grow and make an impact, which stems from trust, is crucial. If a manager verbally offers ownership but micromanages in practice, it can cause team members to feel deprived of their autonomous space, reverting them to merely following orders. Furthermore, trust can strengthen interpersonal relationships within a team. In a team where everyone operates strictly professionally, tasks may be handled correctly, but with low team cohesion, it's easy for responsibilities to be shirked or for individuals to only look after their interests. In contrast, in a trusting and close-knit team, small acts of mutual assistance are more readily accepted.

The Secret of Trust

Trust is essentially a form of currency and a very precious resource. When used properly, trust can enhance efficiency and foster closer relationships. However, the greatest downside of trust is that it is irreversible; once broken, it is nearly impossible to return to the original state of 100% trust. Therefore, both parties must understand that breaking trust is not an option from the beginning. Any actions that breach trust, whether through unkept promises, glossing over issues, or outright deception, can render trust irreparably damaged, often leading to separation. Accidental breaches of trust are also difficult to mend, so it is crucial to handle trust with utmost care and always make decisions that do not harm trust. However, the good news is that trust builds over time. As commitments are met repeatedly and trust is consistently respected, it strengthens, encouraging both parties to trust each other on increasingly significant matters, creating a positive cycle.

A Personal Example

When I was in the United States, I enjoyed rock climbing, which includes bouldering and lead climbing. Lead climbing often reaches great heights and involves longer routes. During a lead climb, you need a partner to belay you, essentially holding your life in their hands. If you fall, your partner is the only one who can stop you from falling further. At that moment, your partner and their rope are your entire world, and all you can do is trust them. If your partner isn't fully attentive and lets you fall a distance before catching you, that trust is severely damaged, making every step you take on the rock more cautious. You won’t feel confident to give your all or attempt more challenging routes for fear of falling again. Conversely, if your partner consistently manages to stop your falls quickly, your trust in them will strengthen, allowing you to relax and perform better on challenging maneuvers.

Trust isn't binary; it thrives when both parties are committed to nurturing this delicate bond, allowing trust to be fully realized and effectively utilized.

How Can Managers Achieve Trust Leadership?

Trust leadership cannot be just a slogan; it requires concrete actions in everyday life. For managers to implement trust leadership effectively, I believe there are three key components: Transparency, Assuming Good Intentions, and Delegation.

🔑 Key 1: Transparency

The first step in fostering trust is ensuring transparency in all possible areas, except for matters involving salaries, personal evaluations, or internal company secrets. The more transparent everything is, the easier it is to build trust. It’s like working in a well-lit room where everything is visible and there’s no fear of the unknown. Conversely, working in a pitch-black room, even if everything is harmless, can make you feel cautious and anxious, unnecessarily consuming a lot of energy.

When I was at Facebook, Mark Zuckerberg worked in a completely transparent office, which he even called the "Fish Bowl," as it allowed everyone to see what he was doing. He aimed to establish a culture of openness, where employees could see what meetings were happening and that there was nothing hidden from them. Another aspect of Facebook’s culture that I loved was the weekly Mark Q&A, where any employee could ask Mark anything, and he would do his best to answer within the limits of what he could disclose. The only condition was that employees had to keep the information confidential. Anyone found leaking information would be immediately terminated, and some people were indeed fired for this.

At Cooby, we uphold a similar principle. Employees can know everything about the company, including funding status, runway, burn rate, and other relatively confidential data. No one wants to work in the dark, and even if the light reveals a messy room, it’s better than a sugar-coated truth. Similarly, we require employees to maintain 100% confidentiality. Trust is mutual, and if one side breaks it, the balance cannot be maintained.

Specifically, leaders need to be transparent about:

  1. Who You Are

    The first and most crucial information that leaders need to be transparent about is who they are. This goes beyond your background or experience, which can be found on LinkedIn. It includes your values, what you care about, your strengths and weaknesses, and how to work with you. In short, it’s a user manual about you. If possible, include even your MBTI and zodiac sign to clearly tell your team how to interact with you. The most important part of this manual is your bottom line. Many people think it’s impolite to tell others their boundaries, as if they are making demands or are afraid to express their needs. However, your boundaries are your boundaries, and they will explode if crossed, even if you don’t write them down. It’s better to clearly state them upfront to avoid unnecessary conflicts.

    For example, my biggest bottom line is not delivering what you’ve promised. I hold myself to this standard, and everyone who works with me knows this. They understand the importance of delivering promises, and if something unexpected happens, they inform me early. This might not be a bottom line for everyone, but stating it clearly can reduce many unnecessary conflicts.

  2. Expectation Alignment

    There will always be expectations between a manager and their team members. Managers control employees’ retention and salary conditions, so it’s natural to have certain demands and expectations. Rather than leaving team members guessing, it’s better to be upfront and write these expectations down. Misunderstandings and disputes often arise from differing interpretations. Even the same text can be understood differently by different people. It’s not uncommon to discover after a performance review that the expectations were never aligned, which is a waste of time for both parties. I made this mistake often when I first became a manager. Now, I believe it’s crucial to write down expectations and discuss them to ensure mutual understanding. The benefit of this effort is that during performance reviews, the manager can use the pre-established criteria to score, avoiding subjective evaluations that can lead to dissatisfaction.

  3. Feedback

    At Facebook, there’s a culture I deeply appreciate: “Feedback is a gift.” Any feedback, whether positive or negative, is a gift because people cannot see themselves or understand the impact of their actions. The closest simulation to reality is the feedback from others. Positive feedback encourages continued good behavior, but constructive feedback, which is more important, is also the hardest to give. It can feel accusatory or make someone feel inadequate, especially in Eastern cultures where bad news is often withheld.

🌟 Bonus: How to Give Feedback?

Giving effective feedback is an art, requiring attention to several key points to achieve the best results. Here are five critical aspects:

  1. Praise in Public, Criticize in Private

    Positive feedback should be given publicly to boost morale and provide a sense of pride, especially when coworkers who rarely interact with the person also see it. This can improve the individual’s reputation and future cooperation. Constructive feedback, on the other hand, should be given privately to avoid issues of face and self-esteem. The best time is usually during a one-on-one meeting, providing a safe space for honest dialogue. If the person disagrees with your feedback, they can voice it without feeling embarrassed in front of others.

  2. Focus on the Behavior, Not the Person

    When giving constructive feedback, always target the behavior, not the person, and provide specific examples. For instance, say, “I think your comment in the meeting was inappropriate because you concluded before hearing the full explanation,” instead of, “I think you are reckless.” The former provides specific instances and reasons, while the latter labels the person and undermines trust, making it hard for anyone to accept the feedback. Effective communication of constructive feedback requires practice and varies from person to person. For those naturally defensive, I use the sandwich method—praise, criticism, then praise again. This lowers defenses and makes the critique more palatable, though it can sometimes dilute the message.

  3. List Action Items

    The goal of constructive feedback is to change behavior, so outlining actionable steps is essential. If possible, include this goal in regular reviews as an item to track and discuss progress.

  4. Reduce Defensiveness

    If you notice the person becoming defensive during feedback, find ways to lower their guard. Use examples from your past experiences to show empathy or explain that your intention is aligned with theirs because their success benefits everyone. If these methods don’t work, suggest postponing the conversation.

  5. Communicate That Trust Is Irreversible

    Trust is precious and irreversible, so it must be communicated clearly from the start. Explain that you trust them 100% and outline what actions would break this trust, such as not fulfilling promises or attempting to cover up issues. Also, state the consequences of breaking trust, such as being removed from a project or the company. Clear communication upfront sets the stage for maintaining trust.

    One of the clearest documents defining trust in my life is Stanford’s Honor Code. Stanford has a unique culture of 100% trusting students and requiring them to follow the Honor Code, with severe penalties for violations. For example, during exams, professors and TAs are banned from proctoring. Once the exams are distributed and instructions are given, they leave the room, trusting students to adhere to the Honor Code. This was shocking to me initially, given the strict proctoring in Taiwan, but it’s effective in fostering a sense of responsibility and integrity among students.

🔑 Key 2: Assume Good Intentions

Another crucial element in nurturing trust is to always default to believing that others have good intentions, reducing the possibility of misunderstandings. For example (purely fictional), if a colleague, A, missed an important setting while working on a feature, causing the feature to fail its launch, and their supervisor immediately assumed that A was careless, this would lead to a problematic dynamic. The supervisor might pull A into a one-on-one meeting to explain in detail how to avoid such carelessness in the future. However, colleague A is typically very meticulous in 99% of their work. This missed setting was purely an accident, and A had already apologized and corrected the mistake promptly, even suggesting a few ways to prevent such issues in the future. Despite this, the supervisor felt the need for the one-on-one, making A feel hurt and untrusted.

Had the supervisor assumed good intentions and believed that the mistake was an honest error, recognizing that A had already taken steps to prevent future issues, a simple expression of support and a reminder to avoid such mistakes next time would have sufficed, strengthening their relationship.

To effectively assume good intentions, a critical technique is to always start with questions and not make assumptions. The questions should be open-ended and not leading. For example, instead of asking, "Were you careless and forgot to double-check?" or "You must not have checked, right?" a better approach is to ask, "What do you think caused this mistake?" or "Did you encounter any difficulties while working on this project?" or "Is there anything happening in your personal life affecting your work?" Open-ended questions allow the other person to explain their situation, leading to a more productive discussion and helping to uncover the real issues that need addressing.

If you start with assumptions, the conversation may become ineffective as the other person spends time defending themselves or, if they don't, they might passively accept the blame without addressing the actual cause. Assuming good intentions generally leads to better communication unless, after thorough investigation, it becomes clear that the person's intentions were indeed not good. In such cases, it may be necessary to reconsider their place in the team.

The debate between the inherent goodness or badness of human nature is age-old, with no definitive answer. However, in the context of trust leadership, I prefer to believe in the inherent goodness of people. Recently, I've been reading about psychology and found the views of Carl Rogers and the subsequent positive psychology movement very compelling, providing a theoretical basis for believing in the goodness of human nature.

🌟 Bonus: Establishing Psychological Safety — Handling Mistakes

Trust and psychological safety are complementary elements; the more psychological safety there is, the easier it is to build trust, and vice versa. Establishing principles and transparency helps build psychological safety, but the most significant threat to it is how mistakes are handled. If our default is to assume good intentions, then mistakes are seen as unintentional. What matters most is how we prevent them from recurring.

People will inevitably make mistakes, but if the team expects that mistakes will be met with understanding and constructive feedback, it reduces the fear associated with making mistakes and encourages boldness and innovation. I handle mistakes and crises with a three-step approach:

  1. No Blame, Focus on Resolving the Issue (Present)

    When a problem occurs, blaming others doesn't help. Questions like "Why didn't you double-check?" or "I told you not to do it this way" are useless and should be avoided. The priority is to resolve the issue. Everyone should come together to tackle the problem, as the team is in the same boat. If the team members are responsible, the person who caused the issue is likely the most eager to fix it, so adding pressure won't help.

  2. Investigate the Root Cause (Past)

    Once the problem is resolved, it's crucial to investigate the root cause. The person most involved should become the Point of Contact (POC) and thoroughly document the incident. This documentation should include:

    • Timeline: Detailed timestamps of who did what and when, how the issue was discovered, and the resolution steps.

    • Detection Method: How the issue was identified (user feedback, monitoring system, internal report, etc.).

    • Impact: The extent of the impact, duration, and any revenue loss.

    • Root Cause: Detailed explanation of the cause, including relevant links.

    • Resolution: How the issue was resolved and what methods were tried.

  3. Propose Solutions and Implement Preventive Measures (Future)

    This is the most crucial part of crisis management—preventing future occurrences. The detailed root cause analysis provides insights into improving processes and preventing recurrence. The proposed solutions should be actionable, and each action item should be reviewed periodically to ensure implementation.

Crises often lead to significant improvements. For example, Cooby established an on-call system following a crisis. Similarly, many security measures at Facebook were implemented after crises. The goal is not to fear mistakes but to handle them constructively, ensuring the company can innovate boldly without breaking trust.

Although the above description focuses on handling software system issues, this template can apply to behavioral issues. For instance, if a team member's lack of motivation delays a product release, you can follow these steps:

  1. Avoid blaming and involve available team members to address the immediate release issue.

  2. Conduct a one-on-one meeting with the member to understand the lack of motivation, assuming good intentions, and clearly communicate that such behavior is unacceptable.

  3. List specific action items for improvement, include items the manager can help with, set commitments from both sides, and agree on a review date to ensure progress.

Knowing how mistakes are handled and seeing this process in action can significantly enhance psychological safety, fostering a culture of trust and fearlessness in the team. A management principle I admire is that "quality is essentially the standard deviation." High quality means low standard deviation, indicating a consistent output. This concept applies to managers—a good manager is highly predictable. Conversely, an unpredictable manager discourages innovation, leading to a lack of creative space and a dominant managerial voice.

🔑 Key 3: Delegation

The purpose of having a team is that one person cannot do everything alone. An individual can go fast, but a team can go far. A crucial responsibility of team members is to share the leader's tasks, and this sense of ownership becomes a significant source of motivation. If you've hired top talent, they will surely want their own space to excel, gain a sense of accomplishment, and receive recognition. Delegation based on trust is essential. Because of trust, leaders can fully let go, giving team members the space to perform, take end-to-end responsibility, and feel their growth.

One of my favorite managers at Facebook excelled in delegation. During a one-on-one meeting, he clearly told me, "Jocelin, you are now the lead for the XXX project. I want you to take full responsibility for this project, including all communications with other teams. If you encounter any doubts, come to me immediately, and I will clarify that you are the decision-maker." Hearing this ignited a sense of strong responsibility and a determination not to betray his trust, motivating me to work twice as hard to complete the project. He clearly defined my responsibilities and assured me of his support, allowing me to focus on the task without worries. He truly walked the talk, refraining from interfering with any decisions and letting me collaborate with PMs, designers, and other engineers. He only checked in during our one-on-ones to see if I needed any help. When the project was successfully completed, he gave me full credit, which boosted my sense of accomplishment and pride, making me more eager to tackle the next project.

Delegating effectively is not easy, but once mastered, leaders will find that their work efficiency grows exponentially. They will have fewer tasks to monitor and can spend more time on higher-level thinking, relying on their trustworthy team members. This positive cycle not only significantly improves practical efficiency but also brings mutual psychological benefits, fostering a sense of achievement and willingness to take on more responsibility among team members.

Is Trust Leadership Suitable for Everyone?

After discussing what trust leadership is and how to implement it, we must consider whether this style suits everyone. This question can be approached from two perspectives: the leader and the team members. Let's start with the team members:

Team Members

I believe most people can be managed using trust leadership, but several prerequisites must be met:

  1. Willingness to Accept and Give Feedback

    Feedback is essential to establishing a transparent and trusting environment. This includes not only the feedback given by leaders to team members but also the feedback that team members provide to their leaders. Transparency must be mutual; a one-sided transparent relationship is still opaque. The worst scenario is when team members harbor grievances but do not voice them directly to the leader, instead gossiping with others. This behavior undermines transparency and can erode trust.

    In Eastern cultures, directly giving feedback to superiors is not always a natural option. Therefore, in addition to leaders creating a psychologically safe environment, it is crucial to ensure during interviews that candidates have the characteristics necessary to engage in open feedback based on their past experiences.

    Additionally, it is vital that team members can accept feedback about their work and not take it personally. If a leader provides specific feedback about an issue, but the team member perceives it as a personal attack, trust leadership will not be effective and could even worsen the relationship.

  2. Ability to Be Honest and Open

    Not everyone is comfortable with or willing to be completely open and honest about their feelings. Sometimes it is due to a lack of expression skills, and sometimes it is a reluctance to share. When there are barriers or hidden issues, trust leadership becomes challenging. Even if the concealed matters are not malicious or unrelated to the task at hand, having an opaque area within a generally transparent environment hinders full visibility. Trust leadership requires mutual transparency; thus, team members are encouraged to share openly with their leaders to achieve optimal honesty.

    However, there is a hard line: honesty. Any dishonesty should be immediately addressed with consequences. Dishonesty destroys trust irreparably, and this must be clearly communicated from the start.

  3. Preferably Believe in the Goodness of Human Nature

    It is easier to align with team members who share my belief in the goodness of human nature. When values and perspectives align, mutual understanding of motives and problem-solving methods is more straightforward, fostering optimism about future improvements. For those with a more cynical view of human nature, it takes more time to explain my motivations and understand their perspective. While I have had success with such team members, it requires more mutual understanding and is not a strict requirement.

What If It's Not Suitable?

If you determine that a team member is not suited to this leadership style, they will likely resign independently due to the mismatch. After all, "People quit their bosses, not jobs." If the team member does not leave for other reasons, the leader must consider whether to let them go. If a few team members cannot adapt to this culture and disrupt the team's cohesion and morale, it becomes a significant issue. Allowing them to stay means the leader will spend more time managing these individuals, detracting from time spent with high-performing members, which is counterproductive. High-performing members need attention to thrive and stay with the team. Early, amicable separation may be the best solution for both parties if cultural fit is a significant issue.

Leaders

Determining if a leader is suitable for trust leadership depends on their comfort level with trusting others. This trust must be genuine and not just lip service; leaders must sincerely let go and not interfere with team members' decisions within the agreed scope. Any interference or reversal of delegated decisions undermines trust leadership and creates insecurity among team members. Letting go does not mean the leader avoids responsibility; they must still be accountable for team members' decisions and mistakes, which is challenging. Leaders must assess whether team members can handle the decision-making responsibility and, once assessed, trust them fully, accepting the risk.

Moreover, listening and empathizing are critical qualities for a leader. Effective listening allows for empathy, and empathy shows genuine understanding and concern, which is felt by the team members. This genuine care solidifies trust and reinforces the motivation to assume good intentions, fostering a positive and trusting relationship.

Conclusion

This is my definition and understanding of trust leadership, shaped by my personality, values, and experiences at Facebook, along with insights from influential books, which I list below for reference:

  • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity (This book aligns closely with my gentle yet firm style.)

  • The Making of a Manager: What to Do When Everyone Looks to You (Written by a former manager from a neighboring team at Facebook, highly respected.)

  • The 7 Habits of Highly Effective People (A classic that needs no introduction.)

  • On Becoming a Person: A Therapist's View of Psychotherapy (Although not directly related to leadership, I love Carl Rogers' principles.)

  • Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century (Written by Twilio's developer-turned-CEO, discussing leadership from an engineering perspective.)

I welcome discussions and exchanges on this leadership style and am eager to learn how it works in other companies!

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My Life as a CTO - Technology (Daily Work)