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If Your Digital Strategy Isn't Lived Every Day, It's Just Wallpaper

If your digital strategy lives in a PowerPoint deck and not in the day to day, it's not a strategy, it's wallpaper. Too blunt? Maybe. True? Absolutely.

I've watched boardrooms in Sydney and Melbourne commission glossy digital strategies that ended up gathering dust faster than an underused meeting room. The trick, the real work, is cultural. Technology is the muscle, but culture is the skeleton that gives it form. Without a deliberate culture shift, even the best tech becomes a cost centre, not a growth engine.

This isn't a sermon about silver bullets. It's a practical argument, from someone who has spent a long time training, advising and sometimes politely arguing with executives about what "digital first" actually means in practice. Yes, leaders must lead. Yes, systems matter. But if you are serious about digital first, you must reorganise where decisions are made, who's trusted with data, and how learning happens, daily, not quarterly.

Why "digital first" isn't just about tech

Let's get this straight: digital first isn't a shopping list for your IT department. It's a mindset. Tools change, CRM one year, AI tools the next, but a digital first Organisation thinks differently about customers, data, risk and learning.

Three quick, mildly controversial takes:

Remote work isn't a fad; properly supported, it improves output. Many managers don't want to hear that, but it's true. Productivity and engagement can improve when you focus on outcomes, not facetime.
Large incumbents do a lot of the boring stuff brilliantly. Don't throw the baby out with the bathwater, learn from the processes that work in big banks and telcos.
"Fail fast" as corporate signage? Overrated. Fail thoughtfully and learn deliberately. There's a difference.

These positions will annoy some people. That's fine. A digital first culture should be comfortable with tension. If your strategy seeks universal approval, it's probably weak.

The hard truth leaders need to accept

Leaders must stop treating digital as a project and start treating it as an operating model. This means:

Decisions supported by live data, not opinions or gut instinct alone.
Flattening some decision rights to enable faster testing and iteration.
Investing in continuous capability building, not a one off training day.

The World Economic Forum has put a number on the scale of change: by 2025, roughly half of all employees will need reskilling. That is not a gentle nudge. It's an industrial scale shift. If you're not planning to re skill, you're outsourcing your future.

Core values that actually matter

If you want people to make digital choices instinctively, embed these values into daily rituals:

Agility: small cross functional teams make small bets often. Not endless committees.
Transparency: data and decisions visible, not hoarded in silos.
Customer obsession: decisions start with customer outcomes, not internal convenience.
Psychological safety: people must speak up when workflows fail, without fear.
Continuous learning: micro learning, regular practice sessions, and on the floor coaching.

Organisations that truly succeed are unapologetic about placing these values into performance reviews, recruitment criteria and leadership KPIs. If it's not measured, it'll be lip service.

People, not tech: the pivot that matters

A lot of leaders buy the latest platform and expect culture to shift overnight. Spoiler: it won't. The pivot that matters is human. Put three things in place:

Intentional learning pathways. Replace compulsory one day training with a sequence of short, applied learning moments, simulations, shadowing, coaching and live problem solving.
Role redesign for digital fluency. Rework job descriptions. If a role touches customers or operations, it should include digital skills as a core competency.
Career pathways that reward digital behaviours. Promotions should recognise collaboration across digital channels, data literacy and iterative delivery.

Training without application is theatre. The ROI comes when people apply new skills in real work, with real feedback loops.

Practical pillars for a digital first culture

There are practical building blocks that help move theory into practice:

Data literacy for all: Basic analytics shouldn't be elite. Teach staff to read dashboards and act from insights.
Cloud first infrastructure: Yes, cloud saves you time. But more importantly, it enables agility and experimentation.
Automation of repetitive tasks: Free up human energy for judgment intensive work.
Collaborative platforms: Unified channels for communication and document sharing (the exact tool matters less than the behaviours you bake into using it).
Governance and security: make these enablers, not hurdles. Clear guardrails actually speed things up.

People often confuse tooling with transformation. Tools help, but only with the right governance, training and user centred design.

Dealing with resistance, it's human, and that's okay

Resistance is part of the journey. People fear the unknown. They fear loss of status or redundancy. Leadership that wants to speed up transformation but skips the empathy will fail.

Some tactics that work:

Engage early and often: involve teams before decisions are final.
Create visible quick wins: demonstrate benefits in a few weeks, not months.
Offer safety nets: show how roles can evolve; provide retraining pathways.
Leaders must be visible learners: public learning signals (leaders attending workshops, using platforms) matter.

Cultural inertia isn't solved by mandates. It's solved by creating repeatable experiences that shift daily habits.

Skills gap: do not outsource your capability building

There's a persistent myth that digital skills can be hired in. You can hire some capabilities, but large scale change requires growing your own talent. Two lessons from the field:

Blend hiring with internal apprenticeship programs. Pair experienced hires with internal talent to circulate tacit knowledge.
Tactical micro credentialing works. Short, practical modules aligned to daily tasks beat long university diplomas when time matters.

We run cohort based programs where employees complete a short project during the course. That's where learning sticks: when it's applied.

Security and privacy: the foundation, not the afterthought

Security isn't a roadblock. It's a Business enabler. Customers and regulators expect controls. The best approach balances access and protection, a zero sum mindset wins no one's trust.

Practical steps:

Embed security training into role based learning.
Automate controls where possible, policy as code.
Communicate transparently when incidents happen. Quiet cover ups destroy trust faster than the breach itself.

Companies that marry user experience with good security practices earn trust. That's competitive advantage.

Tools that actually change behaviour

Here's where pragmatism helps. You don't need every shiny product. You need tools that change behaviour.

Collaboration platforms: chosen for how teams will use them, not for feature lists.
Analytics & BI: start with a small set of metrics that matter to customers and teams.
Automation & RPA: pick repeatable, high volume tasks and free people for judgement work.
AI assisted assistance: use responsibly, treat it as augmentation, not replacement.

One pet peeve: organisations buying expensive AI platforms and then not investing in people to use them. It's the human interface that creates value.

Cloud as strategic muscle

Cloud is more than cost optimisation. It's the muscle for speed. If you want rapid experimentation, you need environments that can be provisioned and decommissioned in hours, not weeks. Cloud native patterns also help with observability and continuous delivery.

But it isn't automatic. You still need governance, cost management, and platform teams that enable the front line. Treat cloud as a product your developers consume, not a capex project to be finished.

Collaboration and comms, the simple stuff that often fails

I'm blunt: organisations that don't sort basic meeting hygiene and document versioning create friction that tech cannot overcome. Clear norms about where conversations happen, how decisions are recorded, and who owns outcomes, these simple things compound.

Empower teams with playbooks: how to run sprint reviews, when to escalate, how to use shared channels. Over time, these rituals become the engine of digital first behaviour.

Analytics and decision making: stop debating, start testing

Data is messy, but the right approach is to use it to reduce the scale of debate. Small experiments, clear success metrics and short feedback cycles beat long winded debates about perfect strategy.

A practical cadence:

Monthly experiments with clear hypotheses.
Shared dashboards with outcomes and learnings.
Quarterly retrospectives to institutionalise what worked.

Leaders must be willing to act on what the data shows, even when it contradicts the plan. That's the test of a data driven culture.

The customer must stay central

If your digital workstreams are internal exercises, you've missed the point. Digital first means making decisions that tangibly improve user outcomes. Customer journeys mapped to outcomes compel different choices than departmental optimisation.

Customer centred organisations do two things well:

They bring the voice of the customer into the design process, early and often.
They measure the impact of changes on actual customer behaviour, not vanity metrics.

If you can't point to a handful of customer improvements driven by digital change, you've probably been doing "activity" not "impact."

Measuring progress, forget vanity, focus on capability

Stop measuring digital adoption by licences issued. Measure by:

Time to impact for new features.
Percentage of roles with basic data literacy.
Employee confidence in using digital tools (surveyed quarterly).
Customer outcomes tied to digital initiatives.

These measures are harder to game. They force leaders to invest where it counts.

Scaling what works, replicate, then customise

Too many organisations insist on bespoke solutions for every business unit. Replicate the core first: templates, playbooks, reusable components. Then customise where it's necessary.

Design systems, modular cloud patterns, and shared analytics taxonomies, these accelerate scaling. Centralised enablement teams should act like an internal consultancy: rapid support, not gatekeepers.

The role of internal marketing

Don't underestimate this. Transformation needs internal marketing that tells stories, celebrates wins and normalises new behaviours. This isn't spin; it's necessary visibility.

Two examples that work:

Short case study videos of teams using new tools to deliver results.
"What went wrong" sessions where teams share mistakes and learnings publicly.

Normalising mundane success is how you shift culture.

A few tactical missteps to avoid

Don't over centralise decision making in a central "transformation" office. It becomes a bottleneck.
Don't under invest in change management. The technology may be straightforward; changing behaviour is not.
Don't assume one size training works. Different audiences need different experiences.

A final, slightly contentious thought: don't fetishise disruption. Australia needs organisations that can execute reliably and innovate safely. Both matter.

Where this gets real

We run programs where participants build a digital pilot during the training. They come with a problem, a Customer pain point, a workflow waste. The learning isn't complete until that pilot shows measurable impact. This is the difference between talk and transformation.

If you want a short checklist to kickstart real change:

Executive alignment: clear, visible leadership commitment.
Living roadmap: measurable, customer focused outcomes.
Capability pathways: micro learning, role redesign, apprenticeships.
Platform decisions: cloud first, modular, governed.
Measurement model: outcome based metrics, not licences or vanity stats.
Internal enablement: a productised support team, plus internal marketing.

Change isn't neat. It's iterative, noisy, and sometimes messy. But that's the point. Digital first organisations survive and thrive because they embrace a bit of messy.

A closing note, blunt and human

Digital first is not a destination. It's a daily practice. If your leadership treats it as a project with an end date, you'll be rebooting in five years when the next wave arrives. If instead you build learning into the rhythm of work, decentralise decision making, and keep customers at the centre, you'll have a fighting chance.

We help teams with the human side of this, the coaching, the practical learning, the playbooks. That's where the money is made: small changes that compound into real advantage.

And one last thing. If your strategy document hasn't changed in six months, put it in the bin and start again. Better: start with a pilot, measure, learn, repeat.

Sources & Notes

World Economic Forum, Future of Jobs Report 2020, estimate that by 2025, around 50% of employees will require reskilling due to technological change.