This is my second episode experimenting with live coaching sessions. The format is my attempt to scale insights on common queries and themes I’m often asked about by listeners.

This caller was looking for guidance after finding that a role they joined 4 months ago was not what they expected. Their situation exemplifies the kind of hard problems that leaders have to solve, and we speak about the traits and strategies required to approach these problems wisely.

Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.

In today's episode, we discuss:

Why the caller’s difficult scenario could be their greatest opportunity
How to think about a current role in the context of future goals
The nature of tough leadership problems
The value of patience and long tenures
How to align on performance and timeframe expectations with higher-ups
Advice for solving contentious problems with multiple stakeholders

Timestamps
[00:00:00] Introduction and context on caller
[00:02:43] Caller’s question
[00:06:35] Nikhyl’s initial reaction
[00:09:11] Could she solve this problem if she wanted to?
[00:10:48] The relevance of patience/impatience
[00:12:40] The relationship between tenure and solving hard problems
[00:15:20] Earning trust as a leader
[00:16:30] Understanding the company’s expectations and timelines
[00:18:05] The advice discussed so far
[00:22:54] Why this matters for future opportunities at startups
[00:27:10] Advice for approaching this challenging leadership scenario
[00:31:08] Nikhyl's closing reflections
[00:33:45] Key links for this podcast

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Coaching grit, patience & tenure

The Skip Podcast