Why Your Best Managers Are the Ones Who Stop Giving Answers

Cameron Adams -- co-founder and CPO of Canva, a company generating $2.3 billion in ARR, profitable, growing 60% year over year with 4,000+ employees -- took coaching to its structural extreme. Canva does not have traditional managers. Everyone has a coach.

"We don't really have managers, but everyone at Canva has a coach. They're constantly working with you to look at your skills, but also when it might be time to move on to the next level."

Cameron Adams

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This is not a startup experiment with flat hierarchy. Canva is one of the most financially successful private tech companies in the world. Their model works because it reframes the leader-report relationship: the coach's job is your growth, and performance conversations happen in the context of development, not judgment.

Adams pairs coaching with a cultural foundation he calls "giving away your Legos" -- as the company scales, you pass on your responsibilities and find joy in building teams rather than hoarding control. He personally runs every new hire through Canva's cultural onboarding, setting the coaching expectation from day one.

The strongest argument for Canva's model is the motivation it creates. When your relationship with your leader is fundamentally about your development, you are more likely to take risks, admit mistakes, and ask for help. Coaching and accountability are not mutually exclusive -- the coach is still responsible for helping you succeed, which sometimes means difficult conversations. The difference is that those conversations happen in a growth context rather than a judgment context.

Ken Norton -- who spent 14 years at Google leading product teams that built Google Docs, Google Calendar, and Google Maps (products now used by over three billion people) before becoming a full-time executive coach -- draws the sharpest philosophical line between coaching, mentoring, and managing.

"I see executive coaching as a partnership or creative partnership. It's all about helping my client reach their goals, their potential, whatever that means to them. So an important thing about coaching is the definition of success does belong to the client. I don't have an agenda. I don't have a set of things I'm trying to share, teach, learn."

Ken Norton

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Most people who call themselves coaches are actually mentoring -- giving advice based on their own experience. Norton's distinction is the philosophical backbone of the entire debate: real coaching's core tools are listening, curiosity, and open-mindedness -- not expertise transfer. He extends this to a career-stage framework:

"It's a question of how much are you looking for someone to tell you the right way versus how much do you believe that there even is no right way? It's ultimately going to have to be your way."

Ken Norton

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Earlier in your career, you need someone to tell you the right way -- that is mentoring. Later, when you have internalized frameworks and optimized them, the emergence required to reach the next level comes from inside you. That is when coaching works. Coaching a junior engineer who lacks domain knowledge will not unlock hidden inner wisdom. But coaching a senior product leader struggling with a strategic decision is entirely different -- they have the context, they just need help thinking clearly. The sequence matters: teach, then mentor, then coach.

Marty Cagan -- founder of Silicon Valley Product Group, author of Inspired and Empowered, and a former VP of Product at Netscape and SVP at eBay -- elevates the conversation from individual leadership style to organizational capability.

"Executives at Microsoft, Google, Netflix, Apple, they've all been bragging about how much they care about coaching. Literally Sundar at Google has been saying that the number one thing they look for in their leaders is a good coach. The number two thing is that they're not a micromanager and they know how to empower their teams. But at Microsoft, they have three principles for their leaders, they're managers that they've been advertising. Number one, coaching. Number two, caring. And then at Apple, they have four big responsibilities for their leaders. Coaching is one of them. They've all been more vocal about this."

Marty Cagan

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This matters because it changes coaching from an individual skill to an organizational norm. Cagan traces the lineage back to Bill Campbell, whose coaching influence spanned Apple, Google, and other Silicon Valley companies. But the new development is that these companies are now publicly advertising their commitment to coaching -- essentially saying, "Come work here. We care about developing you in your career."

The organizational framing solves a problem that individual coaching advice cannot. When one manager coaches but the rest of the company directs, the coaching manager looks slow. When the entire company establishes coaching as a leadership principle -- as Microsoft did under Satya Nadella -- the directing manager is the one who is behind.

Lenny's Newsletter reinforces this dimension. The GAIN framework for feedback, developed by Jack Cohen through 11 years of coaching hundreds of founders and executives, operationalizes coaching by reorienting feedback from what people did wrong toward what they stand to gain (Goal, Actions, Impacts, Next actions). As one startup veteran described it: "After I gave feedback in this new way and saw people actually listen and change, I was like, 'This is great. I can do this.' It created a positive feedback loop."

The newsletter also explores how coaching cascades through management layers. In "Five principles for successfully managing managers," Saumil Mehta (who led 800+ people and 100+ managers at Square) argues that all manager challenges are either directly or indirectly about the skip lead. A skip lead who directs their managers trains those managers to direct their reports. A skip lead who coaches creates a cascade of coaching throughout the organization.