Failing Fast Is Not Just For Startups – It’s For Relationships Too

As loathe as I am to admit it, your hero (in the event you are joining us here for the first time, that would be yours truly) makes the occasional mistake.  Right now you are thinking my first mistake is that I wrote this just after Halloween and not on April Fools Day.  However, I can assure you that despite a reputation in my field for both relative infallibility and rampaging masculinity, only the latter is truly a constant.   

Before I get to my point here, let’s have a heart to heart in the way that only two loose associates on the internet can have with each other.

  1. Have you ever dated someone who was clearly toxic to you but that you stayed with for some reason, hoping things would get better even when your friends and family warned you that perhaps nearly getting into a fistfight with a patron at a coffee shop over who was dating you and throwing a dictionary at your head over a balcony was not a good sign of your relationship prospects?  I mean, just as an example.  That could be anybody.
  2. Have you ever avoided having a difficult conversation with a higher-up because you were worried about what the impact of that conversation would be?
  3. You have a handsome and rugged leader who is 230 lbs of ripped muscle – we’ll call him, um, Justus – and don’t want to make waves at work, but you know that you will need to talk to him about wearing his sexy muscle T-shirts into the office because while it’s excellent for team morale it’s a disaster for your marriage.
  4. For those of you who are leaders – have you ever put off having a difficult conversation about someone’s lackluster performance because “I want to give them a bit of grace, this can happen to anyone” or “I just want to hit this release and *then* we can talk about it” or any other number of excuses?  And they are excuses.  Let’s get real.


Me neither.  But for those of you that might have done this once or twice (looks back and forth shiftily), I wanted to talk a little bit about Lean principles can save you a lot of time and headache.  To be fair, I’m not really the guy to be talking about this – or maybe I am (DUN DUN DUNNNNNN!) because for a guy that is all about Lean, failing fast, Building, Measuring, and Learning, I’m embarrassed to admit that I’ve realized I have done a poor job of Learning when it comes to the above.  It’s actually my worst quality.  Now fortunately I’ve got a zillllllion great qualities to make up for this, my humility being the foremost, but this article isn’t about how awesome I am, but how *awesome* you will be for implementing the advice I am failing to implement myself.  Trust me!

One of the central tenets of Lean is the elimination of waste.  So for all of you proponents of Lean Startup, Lean Management, and Lean Muscle like yours truly…when you put off that critical and difficult discussion with a fellow manager who isn’t doing their job properly, with the employee who has been dogging it enough to affect the remainder of their team – you aren’t being Lean.

This sort of thing is terrible, wasteful and it’s all for the same reasons that some startups linger without being released (without ever being released!!) for years (for years!!!) – it’s fear.  Fear that something adverse will happen, fear of destroying a relationship, fear of change, fear of whatever.  Your fear is bull.  You need to kill it.  Or at least you need to work past it.    Your fear is costing your company money.  One day it might even cost you the company itself.

This is where failing fast comes in.  In Startup terms, this means you run an experiment quickly to determine whether the direction you’re taking is worthwhile and you avoid wasting your valuable money and time.  In working with people, it means that it is critical that you fail fast with people so you can succeed with the *right* people as quickly as possible.  Otherwise – again – you’re wasting your valuable money and time.  

To give you an example from my enterprise days, interviews used to happen with an in-person that involved three high-level people including myself.  This was a 90 minute interview that cost roughly $500-$600 per interview depending on the blended rate.  In the interest of fairness all questions needed to be asked even if it was clear after the first 3 minutes that the candidate was not a fit.  After a couple of these failures there was also some pressure to hire because there was a realistic staffing need.  As I didn’t want to hire substandard people for a critical project,  I instituted a simple technical phone screen of 8 fairly basic questions that could be run through in about 5 minutes of time by 1-2 people.  If you passed that interview, you made it onto the next one.  Now, a failed interview didn’t cost $600 to run, it cost $5-10.  That is a savings of more than 98% per interview.  Now multiply it by the 55 interviews we ran to find the 3 candidates we needed and the cost difference here would have been:

$600*55 = $33,000

$10*55 + $600*10 (the number of people that passed the screen) = $550 + $6000 = $6550.

That’s right, just instituting a phone screen for government RFPs saved the government roughly twenty-five thousand dollars on one set of interviews.  Wow, that reads pretty bad-ass now, if I’m perfectly honest.   Might be throwing that one in my profile.

This also goes for poor performers in your organization, or poor management you see in your organization.  When it’s not working, you need to either pivot or throw it away and that unfortunately goes for the people you lead as well.  I have watched poor leaders end up destroying a team because of their fear of confrontation, just as I’ve watched non-productive or even caustic employees slowly kill an energetic and disciplined team when no one acted to stop them.

Unfortunately when it comes to this, the personal side of Lean – I am awwwwwful at it. I’m not going to spin this as some garbage like, “Oh, I’m just too nice.  I want to extend grace”, or something else.  I mean, I’ve got a cold reptilian heart that despises other human beings!!  Why else would I be in the technology field?  

Artist's rendition of the author's right ventricle
Artist’s rendition of the author’s right ventricle

No, this is simply because as much as I will eventually go through confrontation if I have to, I hate it.   But in that avoidance I know that I – and others like me – in the interest of giving people opportunities that they shouldn’t have had, have cost organizations money and more importantly have cost other people time.   I’ve always eventually come around.  But I am open to saying to a wider audience that perhaps I’ve previously come around too late.


I’m well aware that there’s a grand dichotomy between a guy who is all about wanting to move fast and eliminate waste with a hardened and sharp-edged uncaring mind, and yet dragging on or delaying difficult conversations to the end of the next millennium.  But that’s the beauty (to bring it annoyingly back to this topic) of Lean – there’s never an end to the Learning, or the Building, or the Measuring.  And now that I’ve Learnt, it’s time to Build and Measure once again!!  Hopefully the benefit of my taking so long to finally Learn is that you, dear reader, can skip that step and go right to the Building and Measuring part yourself.  

Next time: I might reveal a secret about myself that almost no one reading this knows. No, not the gigantic Transformers collection.  The other one!  

Advice From A Great Man To The Occasionally Insecure

As much as I wanted to bring you the exciting conclusion to our saga on feedback today, sometimes my philanthropy gets in the way.

A friend of mine on Facebook (who I’ll leave anonymous) wrote:

What strategies do you use for learning about your craft from people who are better at it than you… without getting depressed about how much better at it they are than you?”

Now, as a reader of this blog you are obviously at the top of your chosen field, so your first reply to this person would be “You’re friends with Justice Gray on Facebook!?!?  Can you introduce me?”   First of all, don’t get that excited – being my Facebook friend is basically like reading these entries, only with several more photos of rare Transformers and discussions of limited edition breakfast cereal.  Second, this isn’t all about you!  Someone is hurting here, remember?

Getting back to Anonymous Warrior’s statement here, let’s split this into two parts:

  1. “What strategies do you use for learning about your craft from people who are better at it than you”
  2. “…without getting depressed about how much better at it they are than you?”

Here’s my first and most important piece of advice: the former is a great question, and the latter is a *terrible* one.  Most of you can stop reading here.  Feel free to contact me for my life coaching rates.

Next piece of advice: learning from other people is awesome.  Learning should be inspiring, engaging, and moving. If you are sitting in a bathtub eating a mixture of cookie batter and your tears after learning from someone, I am very confident that you are doing the learning thing wrong.

He looks happy, but he's dead inside.  Trust me.
He looks happy, but he’s dead inside. Trust me.

Here’s a question: when you get depressed about how much better someone is at something than you are…who does it help?  It doesn’t help you get better at *anything* (except maybe weeping quietly).  It doesn’t help the person who is better at that something.

And if that person is actually taking their valuable time to teach you, I might even argue that it’s a disservice to that person and the time they have spent.  You’re rewarding their efforts with what…angst?!  Reward them by showing up, by being grateful, and – while I don’t want to sound too Vancouver pet psychic here – by enjoying the journey.

I don’t want to give you the whole “blah blah just be yourself” trust exercise BS you’ll see when people want to encourage the mediocre.  Maybe who you are *is* terrible!  Maybe you’re a walking failure!  Maybe you shouldn’t be happy with who you are!  I doubt it.  For one thing, you’re reading this article, which is already the hallmark of successful people!

But if you are unhappy with who you are, be unhappy because you know you can do better than who you are right now, not because you want to be like someone else.  Don’t make your goal to be the next Steve Jobs/Dwayne Johnson/Justice Gray.  Keep a poster of them under your bed to keep you feeling safe and loved at night, sure.  But make your goals bigger than trying to be like someone else.  That’s the problem with this question – it still makes your end goal being like someone else.

Be a better you instead.  It’s a greater goal.

(Unless you could be me.  But you can’t.  So being you is still pretty good.)