If you're too busy to read, this picture sums it up

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.