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!  

Feedback Like A Startup – Part 2 of a Series Within A Series

When we last left our series we had talked about:

  • seeking feedback often so that you could both improve your organization *and* annoyingly co-opt Japanese phrases into your everyday vernacular
  • celebrating people who give you the courage and commitment to give you that feedback


Today, as promised, we’re going to talk about emotionally preparing yourself for feedback by breaking the news to you swiftly.

1) What you want to hear and what you need to hear are often two different things.

It’s nice to pretend that everyone you ask for feedback is simply going to say, “My, Justice, you look strapping and handsome today, but you do every day A HA HA HA HA would you like to join me for a spot of tea?” but the reality is that many times feedback will make you cringe.  When pre-public release feedback on a particular section of inContract’s “For Consultants” section indicated one of the pages was confusing and needed a radical overhaul, there was a part of us that honestly winced at having to rework it.  However, without that feedback we would have launched something that didn’t have as pleasing a user experience.  If the feedback is true and actionable, then it’s less painful to hear it and take action on it than it is to never know it’s a problem.

Likewise, for your organization if someone provides you with feedback that something could be operating better (or even worse, is broken) it’s not going to feel awesome.  If you’re an old hand to successful leadership I’m not telling you anything you don’t already know.  If you’re new to the leadership thing, I’m warning you about this in advance because I have met an alarming number of “leaders” in enterprise who, once receiving feedback, have no idea how to emotionally deal with feedback in a proper way and sometimes lash out at the people giving feedback.  (this isn’t even with me being the one offering it, as obviously I’m smooth like a predatory bird when it comes to delivering tactful feedback).  You want to avoid this at all costs.

Artist's interpretation of yours truly
Artist’s interpretation of yours truly


Now, if someone *is* giving you feedback that’s personal, that’s different.  Let’s say for example that someone comes to their anonymous leader in private and says, “Justice, your rippling muscles are a distraction to all of the staff here, not to mention a threat to the sanctity of their marriages”.  Now, said leaders reactions can range from:

  • This feedback is ridiculous, and so are you – YOU’RRRRRRRE FIRRRRRRED!!” as I…ahem, the supervisor flexes their massive pipes at them on their way out the door.  This is a bit too aggressive.  Sexy, to be sure, but too aggressive.
  • Leader asks what they feel they could do to improve the situation, perhaps offering to stop wearing the jean jacket with the cut-off sleeves to meetings as a first step.  A good intermediate.
  • Leader asks to table the conversation so he/she can appropriately think about next steps.  See the next point below for how long you should give.

Be prepared to act swiftly and personally on feedback.

Once feedback has been given to you, my rule of thumb is:

  • feedback should be acknowledged (and restated back to the deliverer) by the end of the conversation immediately if it has been delivered personally (face to face, voice to voice)
  • no less than 24 business hours to acknowledge it if it was received through an impersonal medium like E-mail, text, or strippogram
  • no less than 48 business hours to communicate some initial actions on it (even if that action is “no action”…see below)
  • always record your understanding in writing and make sure the other party agrees that you understand them appropriately.  You don’t know how many times I’ve had to resolve a dispute between two parties where it was clear that either the two parties had completely misunderstood each other or one party was pretending to give feedback that they never actually had given (“Hi, Justice, how was your day, that cut-off jean jacket is looking impressive, please don’t hurt me” is not “I already warned Justice that his steroid abuse is out of control ”).  The important thing here is simply that both of you clearly understand each other.

Remember, It’s often hard for people to offer feedback in the first place, and they are spending their valuable time and energy to give you that feedback.  Respect that time and energy by promptly letting them know you’ve heard them and they will give you a lot of respect in return. Trust a guy who has gotten a *lot* of feedback from the teams and organizations he has led: I didn’t come up with these rules arbitrarily, I endured a lot of pain to figure them out.

If you get feedback that is actionable, you need to take action.  This sounds obvious, right?  Sure, but if you are part of a large organization it is easy for the feedback to be offered and then lost to some “political process”.  Even if you have to take small steps in the immediate while your larger steps have to take place later, it’s critical that the people who gave you that feedback can see that you are taking that feedback and actually doing something about it.

What happens if the feedback is for several levels above yours?  I have bad and controversial news for you: if you are in a leadership position and your team gives you feedback, you have a responsibility to take the feedback you are given and become its champion.  Really?  *Really*.  We’ll be discussing how to do this as effectively as everyone’s favorite bastion of integrity, courage, and humility another time, but I want to plant that seed of brilliance before we get to that.

Next time: nothing to do with that.  Instead – remember “when not to take action”?  I’ll tell you all about it.  Get the fire-retardant gear ready!

Welcome To The Future, Part One Of An Infinite Series: Introducing inContract

Show of hands – who would like to make $300/hr doing executive consulting in Boston?

Perhaps that’s too far east and you’d be content with completely reinventing health care in Honolulu, Hawaii?

Or – you’ve got a role that needs a top-level management consultant like the ones above, and you are ready to enter a world where you can find someone of this level without having to screen, pre-screen, and *re*-screen applicants.  And without paying an agency.  And for free.  (For free?)  And possibly find an applicant who uses better grammar than *this* paragraph!

These are just ridiculous fantasies, right?

Good news: today those ridiculous fantasies can become your reality, because inContract is now live.

If you’re a talented freelance management consultant or a company that has been in need of one, you’ve felt the pain, and you’ve felt the difficulty of matching truly talented people to truly deserving roles.  So did we.  In particular, so did our CEO Kurt Wilkinson.   If you’ve seen his inContract profile, you can probably understand why so many companies have looked to him to help point them to qualified people.  Kurt had been almost buried alive by requests for referrals of fellow management consultants from the companies that desperately needed them, or even other freelancers that were looking for people to help them out on a project!

inContract is our solution to this problem – a professional network for pre-screened freelance management consultants and the companies interested in hiring them.

From our handsome “About Us” page:

“this is where we see the biggest gap in the freelance market. We are not the creators of the talent marketplace concept, but the large freelance markets that exist today are saturated with technical talent of varying quality, not pre-vetted management consulting talent. Our focus for inContract is quality over quantity, focused specifically on management consulting.”

I know, I know – you didn’t come here to read regurgitated yet excellent and well-crafted website copy that you can read anytime; you’re here for the insider perspective from one of inContract’s founders!  All right then, leave this between you and I: inContract is where the world-changers meet the world-changing.

Companies tell us that hiring good people is hard.  We agree.  We want to make it easier, and we want you to find great people.   Unbelievable, unforgettable people.

Consultants tell us that they want to spend more time actually doing the things they do best, without having to sift through 100+ “management consulting” results of which only one or two are even *relevant* to the talents they have.  We agree.  You’re very good at making companies more effective and efficient – why shouldn’t finding your next role be just as swift and productive as you are?

“This sounds amazing, and it’s free?  What’s the catch?  There has to be one, right?”  Well, the bad news (if you can call it that) is that inContract is focused exclusively on the management consulting industry *and* we pre-screen to ensure the quality of the marketplace, so it’s obviously not for everyone.  On the other hand, the fantastic news is that if you are a consultant or company that is part of that industry, then we are definitely for you, as you can say goodbye to having to sit down for several hours going through either unqualified applicants or irrelevant roles.   If we weren’t very confident of that, we wouldn’t have bothered building it for you.   And now it’s yours!

“Wait, you said part 1…what’s part 2?”

*laughs* Oh…if only I could *tell* you that without giving it away…trust me.  Have I steered you wrong thus far?

How to Get Your Enterprise Running Like A Startup, Even If It Isn’t: An Exciting Prelude

If you have ever sat at your desk in your office or cubicle and thought any of the following thoughts:

“I wish our operation could be better, but we’re just too big”

“I wish our operation could be faster, but we’re just too big”

“I wish I could be an exotic dancer, but I’m just too big”

Well then congratulations, because this weekly series of posts is for you!  Yes, even the third one.   By the end of this series we’ll have talked about that too.  Really?  Really.  Would a guy you’ve probably just met on the Internet lie to you?  Never.

There are a lot of you out there reading this who work for a monolithic enterprise where release dates of products, systems, and functionality are actually measured in years rather than months or weeks, the earliest your next significant piece of work will see the light of day is 2016(!!) and you now figure your doctor will be delivering your grandchild prior to your company next delivering a successful release.   If reading this hits a painful nerve I want to give you some assurance:

  • it isn’t hopeless
  • your hero has been there.
  • I might know how to make it better.

That’s a bold claim, but tell me if this career journey doesn’t scream “credibility”:

  • start your career at a startup doing “development”, some marketing diagrams, some fetching of coffee, some washing of cars and occasionally coding
  • move over to the enterprise noting what worked well at your previous organizations, implement those changes, work your way up to masterminding the construction, release, and team leadership of multi-million dollar projects
  • leave those behind and join a startup again, doing some marketing diagrams, fetch your own coffee, wash your own car, occasionally code.  This time, however, call yourself a Chief Technical Officer.

I want to spare you that journey and give you everything that has made me successful at the organizations I’ve been and avoid the pitfalls that I’ve encountered or the mistakes that I’ve…*ahem* the lessons I’ve learned that obviously had *nothing* to do with me or my decisions whatsoever. This is my article, I can say what I like!!

Now, this preamble to a prelude out of the way, we should get some stuff out of the way first that *might* blow your mind:

1) Not every startup is an oasis of productivity.

While not listed on my LinkedIn profile (because these clients would obviously prefer to remain confidential), I have consulted for startups who are still struggling to get a release out the door even after months or even years of development.  I actually had a discussion with one notable Vancouver startup that will remain anonymous – we’ll get into them later in this series – that was still nowhere near a stable release despite running with a large team (I consider “large” to be anything beyond 5 people) for nearly half a year.  Unless you are building a functional space shuttle made entirely of chocolate and gold, 6 months is forever if you are dealing with a large team.

Obviously seven years well spent
Obviously seven years well spent

I find that people in enterprise often misconstrue “startup” to be at default some magical place where everything is fast-paced, highly productive, we all wear leather jackets with the words “Black Ops” emblazoned on the back and the day after a product is discussed, a fully featured application is out the door.  Not quite.  Don’t worry though – if you are the kind of person who thought this or assumes that “Agile” means “Let’s all hold each other while we burn our documentation and just…talk about stuff”

  1. I’m not going to hold it against you
  2. You sound like the kind of hippie that I’d love to consult for, please give me a shout so we can discuss rates

The reality, however, is that most of you have all seen what an *efficient* startup runs like, because at the time of this writing the preview for “Fast and the Furious 7” has aired and I want to assure you that minus the cars flying through skyscraper windows, this is pretty much how pineappl operates *every day*, give or take a broken window or two.

More importantly for you startup boys out there who are reading this and thinking “Hurr Hurr Hurr, I’m so glad I don’t slave for the *man* in the <air quotes>government</air quotes>”,

2) Not every enterprise is some lumbering beast that never gets anything done

Having had the experience of being *very* involved in the running of show at one of my more notable clients for several years, there were definitely significant periods where we not only significantly outperformed every other department with a fraction of the people in a fraction of the time, we had people from startups themselves who were amazed at “how fast you guys are…easily ten times as fast as we were at [X]”  You would be shocked sometimes at how fast an enterprise can actually be and over the course of this series I’m going to share with you the things that made my teams sleek like panthers – most of the time.  (Except at pineappl, where we are of course perpetually jungle cats, but enough about the hottest group of C-level officers in the world today, there will be time to discuss that later).

Artist's representation of the pineappl founding team, yours truly furthest on the left
Artist’s representation of the pineappl founding team, yours truly second to the left


3) Productivity is productivity and many things that are ideal situations in a startup can be replicated anywhere, regardless of the size of the enterprise or even the *type* of the enterprise.


BOO YAH.  This is what we want to be talking about in this series.

While I’d *love* to tell you that everything I have touched turned to productivity gold, the truth is that every organization I’ve been part of (save *possibly* pineappl, but I’m a realist and am certain we’ll hit that), whether startup or $20M enterprise project, has had times of ferocious productivity and also times where we ran much slower than we needed to, either because we made a choice that wasn’t great or we drifted too far away from the ideals that made us fast and lean in the first place.


You will not and cannot do this alone unless your “organization” is a team of one.

But, I will show you how to make sure you’re not.

“But Justice, I’m just a developer/admin assistant/car washer/exotic dancer, I can’t make those changes”

Good news, buckaroo.  I started there too.  And in the case of large enterprise, let’s not pretend that *anyone* ever gets a magic autonomy wand, starts waving it, and changes happen.  Every major decision I ever made in a large enterprise had to still go through an approval chain of C-level responsibilities, but trust a guy who has been there, the more credibility you build up, the more relative autonomy you get.  And the more you’re able to introduce what I’m sharing with you here, the more credibility you’ll have.  For example, just telling your co-workers and superiors that “I read an article by Justice Gray today” is a great way to start.  Trust an expert.

Some things you can look forward to in the coming weeks unless I decide to take a page out of the enterprise playbook and stretch this series out over the next decade:

  • How to Hire Like A Startup
  • How to Structure Teams
  • How to Meet Like A Startup
  • How to Work Like You’re At A Startup
  • Leading Like A Startup
  • Whatever Else I Feel Like About Being At A Startup, Baby

Next time: absolutely nothing to do with this series at all.  Well, unless you count a book that will most assuredly change your life and make you the baddest man/woman/force of nature/all of the above on the entire planet after reading it.  It might help.