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The Vulnerability Paradox: How To Use Failure As Your Path To Success

Plus the 10 question test to determine when failure is likely so you can take practical measures to avoid it. 

What not to do as a parent.

Read Time: 4 minutes.

It's funny. The conversations I've been having at home with our teens are eerily similar to conversations with my coaching clients. 

At the heart of those conversations is the topic of failure. And more acutely, is there a difference between failing well and failing poorly?

Based on my experience, there's not a modest difference.

It's more like a chasm. 

At home, the subject is soccer. We're well past even playing time, and everyone gets a trophy. 

Instead, we see the naturally talented but less driven kids and the less talented hard workers overtaken by those with both talent and drive.

Effort is no longer a differentiator; it's a given. Outcomes matter now. 

But what do young athletes do when they only control their effort and not the outcomes? Does it matter if you play well, but your team still loses?

Let's pivot over to one of my coaching clients. 

"The road to hell is paved with good intentions."

"I'm drowning. I have one too many big projects to handle and can't devote enough time to hiring. Without more help, I just fall further behind. I'm losing credibility with the other leaders because I'm not keeping my commitments. It's killing my motivation and making me even less effective. It's a vicious cycle." 

His situation is all too familiar. The effort does not yield the result. 

And he'd be the first to admit he's failing. 

But is he failing well? 

Last Call For February’s MGMT Accelerator

Next Tuesday, we kick off our 9th open enrollment MGMT Accelerator. We have 5 seats remaining and won’t run the program again until May.

Here’s what leaders from our previous cohort said:

“Cannot recommend this course enough. Simple yet effective with actionable steps to take to unlock your biggest management challenges. Asks the hard questions that get to the source. I wish I would have taken this sooner.” - Justin (Manager @ Boeing)

“The best course I’ve taken on leadership and managerial excellence. My only regret is not having taken this sooner in my managerial track. Dave and Marsden are the absolute best teachers. The breakouts and workshop sheets ensure you are leaving with actionable steps to continue to apply what you learn.” - Jesse (Engineering Manager @ Travelers)

“This course challenged what I thought were the core management norms. It offered tangible solutions and created a safe space to explore some uncomfortable truths and provided support to address them.” - Laura (COO @ Belle Haven Investments)

“Wholeheartedly recommend this insightful, thought provoking and superbly delivered course. Be prepared to cover a huge amount of ground, in a short space of time. Over the weeks I have already started acting on some of the learnings and am now armed with a ton of strategies to take forwards in my current role and throughout my career.” - Alexei (Head of Technology @ TUI )

“Thoughtful, thought-provoking, and practical course designed to first help you understand yourself more thoroughly with the end of becoming a better leader.” - Carsten (CEO @ Martin Bionics)

“Incredibly helpful through developing frameworks and systems for new managers, reinforcing good habits for experienced managers, and provoking healthy reflection for all levels. Dave and Mar are great coaches and guides throughout!” Evan (Partner @ The Keystone Group)

The Characteristics of Good Failure

We don't set out to fail. But we can't run from it either. 

So, ensuring we operate the right way sets us up to minimize the impact and maximize the benefit. 

Plenty Loud

The worst way to fail is silently. And yet, for much of our lives, asking for help is a measure of last resort. 

But if we're going to do big, audacious things that haven't been done before, the chances we can go it alone are zero. Not low. Zero.

I expect my teams to get help as soon as they realize they're out of their depth, which might be from Day 1.

Good failure is always loud and never lonely. 

Plenty Fast

A close cousin to volume is speed. 

Usually, this failure comes from encountering something hard and putting off dealing with it. It's one thing to intentionally defer because you believe more time or data will unlock the problem. 

It's another to hit a sticking point and turn your attention elsewhere. Rarely will it go away, and now you're compounding the issue.

Figure out the pivot point and race there as fast as possible.  

Plenty Safe

You can't win a game you're no longer in. 

So, failing well is at the efficient frontier of enough risk to matter but not so much risk that you can't survive a fall. 

But how do we find that Goldilocks zone? 

If you think you're being too conservative and letting fear steer you away from all risk, consider the prompts in Tim Ferris's practice of fear-setting

If a reward looks too good to be true, chances are you are overlooking a considerable risk. Double-check your work with someone who is well-informed but thinks much differently. 

Plenty Learned

There's a phrase I don't love, "You're either winning or your learning." 

I don't love it because the highest-signal learning should come from winning, not losing. Repeating what works is a pretty smart bet. 

But when you come up short, you darn well better learn. The key is to distill the proper lesson. 

Sometimes, you make all the right moves and lose. This is called bad luck. You don't want to abandon a winning strategy because of a bad beat. 

The two most effective tactics I know:

  1. Diagnose the issue to the root cause.

  2. Debrief the failure with an expert.

10 Questions to Understand If You're Setup to Fail

Chances of Failure:

  • Has our company done this before?

  • Have I done this before?

  • Can we run a test?

  • Is this a priority?

Levers to Avoid Failure: 

  • Can the timeline move? 

  • Can the budget change? 

  • Can the complexity be less?

  • Can better resources be lined up?

Consequences of Failure:

  • Do we survive if we come up short?

  • Do I have the personal capital to fail? 

Just answer each one Yes/No. 

The more you answer No, the higher the probability you're on the road to ruin.

Travel safely, friends. 

And as always, thank you for reading.

Appreciate you!


Ways To Work With Us

MGMT Accelerator - Our flagship leadership development program is taught live over 8 sessions. 50 leaders from companies around the world build out their foundational management systems together. Perfect for leaders with 3-10 years experience. Our next cohort starts February 6th.

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