Via Lenny’s Podcast

“I’ve seen leaders at every phase, from frontline managers to running an 8,000 person company, struggle with “When do I have to have the answer?” and “When I don’t have the answer, what options do I have?“

Great leaders know that when you try to advise and have the answer all the time, you’re not actually equipping your team to go solve the hard problems. You’re training your team to come to you with all of the hard problems. And coaching is a different way. It’s an alternative path that unlocks brilliance in your team and is way more motivating for the people around you. So coaching is actually a learnable skill.”

— A guide to difficult conversations, building high-trust teams, and designing a life you love, at 9:56

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1. Great Leaders coach more and advise less.

Many leaders, especially technical ones, climb the ladder by being the smartest person in the room and having all the answers. However, this approach doesn’t scale.

As a leader, your job is to empower your team, not create a dependency where they bring every problem to you. Rachel Lockett (executive coach and former HR leader at Stripe and Pinterest) emphasizes that coaching is the alternative path. As she puts it, “Great leaders know that when you try to advise and have the answer all the time, you’re not actually equipping your team to go solve the hard problems. You’re training your team to come to you with all of the hard problems.”

Coaching involves shifting your energy from solving to curiosity. It means helping your reports solve their own problems by asking powerful questions and creating space for them to think. This doesn’t mean you never advise. Advising is appropriate when an issue is urgent or the person genuinely lacks the necessary skills. The key is to avoid over-rotating on advising and instead use coaching to unlock the brilliance within your team, which is ultimately far more motivating and effective.

2. The GROW model at 18:39

Coaching doesn’t have to be complicated. Rachel introduces the GROW model as a simple yet powerful framework for guiding someone to their own solution. It’s a set of four question categories that help structure a productive coaching conversation.

• G – Goal: Start by defining the desired outcome. Ask questions like, “What does success look like?” or “What’s the best-case scenario here?”
• R – Reality: Explore the current situation. Ask, “Where are you stuck?” “What are your current challenges?” or “What have you tried so far?”
• O – Options: Brainstorm potential paths forward. Ask, “What are the various paths you could take?” or “What other opportunities could you explore?”
• W – Way Forward: Commit to a specific next step. Ask, “What are you going to do next?”

This model helps the individual articulate their own challenge, explore possibilities, and take ownership of the solution. As demonstrated in the live coaching session with host Lenny Rachitsky, walking through these steps helps uncover the root issue and identify a concrete, self-generated action plan, which creates far more buy-in than simply being told what to do.