Time to View Failure Differently
As a Second-In-Command, you're probably a high performer who wasn't allowed to make mistakes out loud throughout your career. Maybe you were labeled “gifted” as a kid and have been living up to that ever since. But here's the reframe: mistakes are a tax you pay on your way to growth. Entrepreneurs view failure completely differently than you do because trying and failing teaches what works.
When you make mistakes (and you will), the key is owning them immediately by answering two questions: can I fix this and how, and how did this happen? Not justification, but a practical postmortem leading with humility and vulnerability.
Entrepreneurs are anesthetized to bad news, and when you bring problems forward with ownership, they have the network and resources to help fix issues. The challenge is to be more open with your mistakes and more vulnerable with both your entrepreneur and your team. You'll grow, and it will inspire your team to take ownership without needing constant confirmation.
You'll hear all about:
00:51 – Today's topic: Mistakes as a second-in-command and why they're the fastest path to growth
01:06 – Origin story: Coaching client's manager outsourcing all thinking to ChatGPT and why that prevents promotability
01:43 – Developing strategic thinking comes down to reps, and those reps are really mistakes
02:02 – Mistakes are data, learning, and understanding – AI can't give you that decision tree to reflect on
02:21 – Training insight: How entrepreneurs view failure differently than the rest of us
02:37 – Many entrepreneurs depend on failure – trying and failing teaches what works and what doesn't
02:58 – Your job as second-in-command: Help CEO understand outcomes and consequences to make informed decisions
03:10 – Reality check: You didn't get to this role by failing – you weren't allowed to make mistakes out loud
03:26 – The “gifted kid” curse: Living up to high-performer expectations your whole life
03:34 – Personal story: Changing an A-minus to an A-plus with a pen, then immediately feeling guilty
04:08 – Reframe: Think of mistakes like a tax you pay on your way to growth
04:21 – Important caveat: Brand new to position or company = less margin for error while proving yourself
04:34 – If you're established or promoted from within, you have room to be riskier
04:35 – What Megan learned the hard way: Trying to be a “membrane” to keep bad news from the entrepreneur
04:57 – Cognitive dissonance: Making mistakes while watching others get terminated for theirs
05:04 – The confession: “I made mistakes I may have fired myself for, and I'd seen others fired for less”
05:14 – The key question: Why wasn't I fired? Why wasn't my CEO even really mad?
05:29 – The two critical elements: Learning from mistakes AND owning every mistake
05:40 – The immediate questions to answer when you cause a problem: Can I fix this and how? How did this happen?
06:00 – Not justification, but practical postmortem – leading with humility and vulnerability
06:20 – When you can't answer those questions, you might not have enough experience yet to analyze what happened
06:32 – Entrepreneurs are anesthetized to bad news – there was never a bad reaction directed at her
06:50 – “As an entrepreneur myself, I can tell you we don't know what we're doing either, but we have the network”
07:03 – Real example: Banking issue led to facilitated training with a banker connection
07:18 – When you present as perfect, you're setting the culture for those who report to you
07:42 – Being resistant to your own mistakes sets that expectation for your team and creates bottlenecks
07:54 – If your team is fearful of failure, they bring everything to you for confirmation
08:10 – High-detail personalities naturally do this, but if EVERYONE does it, work slows down
08:26 – The self-fulfilling stress cycle: Extra pressure on you to get everything right
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