Jay Chia, cofounder of Eventual, joins the show to unpack what real empowerment looks like inside a fast growing startup. Most people confuse empowerment with initiative, but Jay explains how trust, vulnerability, and accountability work together to turn good teams into self directed ones. If you are scaling a startup or leading a growing engineering team, this conversation explores the human side of leadership, when to let go, when to step in, and how to help your team grow without losing alignment.

What You’ll Learn

• Why initiative and empowerment are different and how that distinction shapes your company culture

• How to build trust so early employees can take ownership without constant oversight

• Why vulnerability is the key to honest feedback and deeper one on ones

• How to build a culture of experimentation that rewards progress, not perfection

• When to intervene as a leader versus when to let your team learn through mistakes

Timestamped Highlights

03:20 The difference between taking initiative and true empowerment, and why fixing bugs is not ownership

08:39 Using vulnerability to turn one on ones into real conversations

12:20 Building an experimentation culture inspired by research driven teams

17:53 How much room to give before stepping in, balancing trust, skill, and risk

21:41 Why letting new managers bring their own cultural imprint can strengthen your company

A Line That Sticks

“Empowerment is handing off the monkey. It is not just fixing the problem, it is owning the plan, asking for resources, and having the mandate to execute.”

Practical Advice for Leaders

• Start one on ones by being open first so your team feels safe to share what is really happening

• Lower the barrier to experimentation and let people test ideas early. Progress beats polish

• Build rituals, not just processes. Repetition creates trust and space for feedback

• Encourage a mindset of asking for forgiveness, not permission. Autonomy grows from trust

Keep the Conversation Going

If this episode made you rethink how you empower your team, share it with another founder or manager who is building through similar challenges. Follow The Tech Trek for more conversations at the intersection of people, impact, and technology.