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The unending cycles of cultural transformation
Software companies are by and large an organizational wreck. They are all their own types of wrecks but for anyone who’s moved around in the industry you quickly begin to see the shared pathology. The dysfunction is I think mostly a symptom of demand. The demand on technology and pace of innovation puts companies and their leaders on a speed train to a level of aspiration, responsibility and accountability that often is far beyond their experience and expertise.
When the systemic problems spring up it’s often easier for people to just find a new job rather than do the hard transformative work inside a complex ecosystem. But I’m writing for those of you who stay, who are inspired(or incentivized enough) to, as Jason Warner puts it, “change the slope” of your organization.
For reasons that I’m not entirely sure, I’ve made a career out of this, or maybe more accurately, transformation ended up making my career. It can be both deeply frustrating but also an incredibly rewarding journey when you pour years of effort out to see a group of people reach a level they never thought possible. Each journey is its own steeplechase complete with diverse sets of obstacles that teach you new ways to motivate, reward, inspire and perhaps most importantly persevere. While there is no formula to apply, there are patterns I’ve discovered that I believe are helpful as a guiding light as you navigate the intricacies of your context.
1. Stop doing deathly dumb things
Before you start pouring yourself into investment strategies, training opportunities and re-org plans, or even before you refresh pitch decks with today’s
hawt hot memes that will dazzle the forever near retirement exec who’s stifling all change, you have to deal with what’s killing the team today. It’s the oddly elusive but certainly deadly cultural instincts that the organization is addicted to, that to any outsider reeks of death, but to most of the proverbial frogs in the pot, it’s just another day and the water is imperceptibly warmer than yesterday.
There’s almost certainly good reasons for how the team arrived where they are, why the deadly behavior is now the instinct, and while that may have bearing on how you communicate a necessary change, it can’t prevent you from doing what’s right no matter how much inertia exists.
Be curious and follow the smells.
Be observant and follow the pain.
Be decisive and follow through.
You have to have the guts to be wrong. When you come into an org and wonder how the heck they arrived there, when you see what in any healthy environment would be considered insane yet has somehow become a cultural norm, often times the answer lies right here. It’s far easier to observe than to object, to coddle rather than change.
Examples: “pathological” org structures, hero making, “single throat to choke”, pushing pain downstream, misdirection, change approval boards, poisonous cultural elements(the 10x a$$hole) & transformational detractors
2. Make the right thing the easy thing
At this point you’ve stopped the bleeding from mortal self inflicted wounds, you’ve raised awareness through vision decks and which may have even been positively received but positive momentum is still a far way off. In order to get lift you must find a way to create a foothold by demystifying the brave, but alien new world you’ve been describing as the promised land. There’s no one right way to choose where to start but there are a collection of factors you should consider:
Where is the greatest felt pain in the org and how does that map to business impact?
Where does that pain intersect with relatively few dependencies either organizationally or technically?
Is there a new project where you want to start on a new paradigm and create a “lighthouse model”?
Where do you have change agents and where are the detractors?
As you weigh those factors you want to plot a course for early wins that create a foothold you can leverage for more change in order to develop momentum.
I strongly caution against storming the castle to slay the dragon with your first draw of the sword, there is a trail of failure awaiting you on that path. Instead, focus on building cultural momentum that stays aligned completely to the vision, inclusive of dragon slaying, while piling up small, meaningful win after win.
That gives the team confidence, their own learnings, ownership of the journey and solution and creates the benevolent organizational beast that can take on that dragon through positive inertia.
Examples: CI/CD paths all the way to prod, increased empowerment in teams, better tooling and observability, more direct communication/escalation paths, paved paths
3. Make the easy thing the habitual thing
One of the definitions of culture I find most helpful in this context is the subconscious reflexes of an organization. It’s what people and teams do instinctively. When an org has bad or unhealthy instincts it’s easy to become impatient and unreasonably direct with the correction.
It’s important to remember that cultural turnarounds are not simply a matter of philosophical principle alignment, rather they are the result of thousands of corrections to those principles executed consistently over years all the while effectively enabling the teams(see point #2) so these corrections are actionable.
It takes that type of consistency before you start seeing the instincts change and the cultural current shift directions. I can’t stress this enough, adjust your measurement window to years not months.
The more you can leverage platform patterns and paved paths in your enablement the more positive behaviors your teams consume without democratizing every micro-pattern under the sun. When teams are feasting on a steady diet of “right” and “easy” things, changes to appetites, behavior and instincts will follow.
For corrections that require more challenging or staged adoption, I coach teams in what I call the inchworm adoption pattern upon which I’ll expand in a separate article.
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