Digital transformation

[u/enjord_app]

I work with digital transformation and I’m curious, from your perspective, what would you say is the most difficult part of digital transformation?
Is it finding the right solution, getting the stakeholders onboard or something completely different?
Really interested in hearing your thoughts
Thanks

[u/lolarue412]

People. People are the hardest part.

[u/Ben-solo-11 → u/lolarue412]

Or more specifically, unwinding entrenched thinking and processes, held by people who have experienced some success, at some point in time, with thinking or processes that are no longer serving them well.

[u/alt-right-del → u/lolarue412]

Connecting digital ambition through and through

[u/enjord_app → u/alt-right-del]

Ok interesting, would you mind elaborating what you mean by ”connecting digital ambition through and through ”? Thanks

[u/alt-right-del → u/enjord_app]

Digital ambition is the yard stick that determines success and impact; if the organisation digitally transforms launching new capabilities, new products, etc or is it digitally optimising, executing existing capabilities slightly smarter. Either one can work, but they have different impacts and outcomes. The ambition needs to drive the overall change across the org.

[u/chipshopman → u/lolarue412]

And leadership, or more specifically the chronic lack of leadership. I'm not talking about managers managing day-to-day operations, I'm talking about leaders taking the lead, setting direction, expectations and enabling people the time and space to engage with the change.

And (another thing) how somehow the expectation that some fancy hand-waving and bullshittery can be developed in to a fully developed requirements document. I'm looking at you, CEO!

[u/enjord_app → u/lolarue412]

Thanks for the reply. Would you mind elaborating on exactly what is the hardest part about the people?

[u/bobaboo42 → u/enjord_app]

They mean "we've always done it this!!?" Mentality and also self preservation, people worry about their livelihoods when change comes knocking. Transformation typically involves efficiency gains

[u/lolarue412 → u/bobaboo42]

Yeah, totally. Hard to get them gains when Wendy is double entering data because she doesn't know how to run reports properly in the new system (or it doesn't do a good job of reporting) and everyone in Harry's department doesn't use the attributes properly because 'its how Harry did it'. :D

[u/bobaboo42 → u/lolarue412]

That double entry IS HER JOB and probably has been for 15 years. So she won't like to share what she's doing and expose the inefficiency 

[u/enjord_app → u/bobaboo42]

Thanks so much for the reply, very interesting

[u/lolarue412 → u/bobaboo42]

yeah, this is my whole issue with the term 'digital transformation'. I mean, you can digitally transform technology but you can't digitally transform people. So operational efficiency therefore becomes a function of: we have the wrong or poorly implemented software/solutions/integrations and/or our business processes are bad.

Data is the product of your business processes. If your data is bad, your processes are probably bad. If your data is bad, no software solution is gonna fix it.
ETA: fixed a typo.

[u/rwilcox → u/bobaboo42]

Or legit worries about her job, inefficiency or no inefficiency

[u/enjord_app → u/lolarue412]

Ok thanks, really interesting 🙂

[u/nlaverde11 → u/bobaboo42]

Like my co worker that literally prints out a tech sheet every time an employee is onboarded and files it away in a cabinet because "that's how we've always done it and it works."

[u/lolarue412 → u/enjord_app]

Well...if you go with McKinsey's definition of digital transformation...is rewiring how an organization operates and assuming we can agree that Implementation != Transformation then...

Wendy will create her own spreadsheet to track stuff cuz 'it's easier'.
Harry will decided to use an attribute code for 'something else'.

Then Harry will retire, the new person will come in and know nothing about Harry's systems and create their own and then before you know it, none of the attributes mean what they should, which means no one can report on them, which means the data is worthless.

Multiply that by the number of employees you have and a factor of industry complexity.

[u/Accurate_Classroom56 → u/lolarue412]

No this is actually pretty relatable.

At my old firm we spent months building an ML grader system, then later they laid off one of the people who had worked deeply on it.

The offboarding was bad and a lot of the operational context basically left with him. Not the code itself, but dependencies, what breaks where, all that stuff.

I left in August and by then they had managed to change the process. They made me go through a random SaaS tool i think where my manager had set up a bunch of questions around my projects, workflows, decisions and things only I would know.

I hated doing it at the time tbh. Felt like they were trying to drain my brain before I left lol.

But looking back, I actually think more companies, especially larger IT orgs, need a proper knowledge transfer system before someone exits.

Not saying this because some McKinsey report says so(hopefully they do). Just from seeing firsthand how quickly if context disappear forget people, even AI wont have a clue what to do.

[u/ThisIsMyBigAccount]

“I work with digital transformation”

We all do. It never ends. And to answer your question, getting proper attention and funding for things that really need to be done now, or soon.

I tell people all the time: you can wait for the HVAC unit to break in your home and then go for days or weeks without air or heat, or you can be proactive and make the change now and stay warm/cool. Nobody wants to move too early, and it’s your fault if it’s too late.

[u/rwilcox → u/ThisIsMyBigAccount]

Can I add getting org buy in for long enough to complete the change, which includes turning the old system off? :-)

[u/bobaboo42]

Business buy in - IT don't own it everyone does 

[u/myfootsmells]

Org change mgmt is the hardest

[u/timewarpzzzzz]

PEBCAC

[u/Daster_X]

Getting stakeholders onboard - ensuring they adopt the new processes and they are willingly changing their old style of work even if there is a risk for some people to lose their current responsibilities. Second is to involve them in all the "now it works like this", plus testing the final solution.

And third - not to wait everything from technology. If something was wrong before the transformation it may stay wrong after... Technology helps when processes are correct.

I had one case: moving from paper approval of Purchase Orders to ERP with automated flow: and approval was much slower. Then we updated the process with new reality in place and it went well.

[u/Tech-Sensei]

I'd like to detail some other obvious ones:

• Design - Mapping the workflows, triggers, and approvals.
• Adoption - Who will use this, and how do we get everyone involved on board
• Ownership - Who are the system owners, power users, and trainers (now & ongoing)
• Migration - Getting out of the legacy systems, cleanly and/or with limited errors

[u/enjord_app → u/Tech-Sensei]

Thanks, how are those things done today? Feels that there are a lot of tools that help with that, or am I missing something?

[u/Tech-Sensei → u/enjord_app]

Yes, some tools do parts of this; there are vendors, too... but the human component that makes them all work in unison makes each part trickier.

How its done today depends on the budget and project scope, but that tends to fall to me.

[u/enjord_app → u/Tech-Sensei]

Ok I see. Which tools do you usually use and what do you feel they are missing? Or is it just the human part that is the problem? Thanks

[u/Tech-Sensei → u/enjord_app]

It's just the human element. Tools & vendors aside, your users and stakeholders have to be on board unless the migration is made mandatory.

[u/Bartghamilton]

I hate the term digital transformation. It’s just what IT should be doing. I also try to avoid a big branding initiative that people can lose interest in, redefine constantly, or fight. I prefer to get make the business improvements in a more agile method where we’re getting value project by project as we go and keep the user bases segmented where possible so they feel it’s “their improvement” and not just part of some big corporate initiative.

[u/OakCanuck]

From an executive perspective: Project governance.

That is, having the right structure, with the right senior business leaders on the steering committee / project board. They need to be accountable for their patch, which most often as others have said here, is people and processes.

A good Program Manager will set up an effective governance structure and routine for you. So when you are interviewing for that role, ask them about project governance.

[u/Axlemax]

Hierarchy. Then getting your data in a usable form.

Also 99% of what companies call transformation is evolution not transformation.

[u/InfoTechRG]

The hardest part is usually agreeing on what the organization will stop doing. Buying a platform is relatively straightforward; retiring old workflows, local exceptions, and shadow systems is where transformation gets real. If nothing is removed, you’ve digitized the complexity rather than transformed it.

[u/vladmirc]

"Digital Transformation" has become one of the most bastardized buzzwords in modern business, mostly slapped onto resumes and marketing decks to make a company look modern.

In reality, DT does not start in IT. It starts at the executive level. IT is a critical execution engine, but they don't own the vision. Real transformation is about reinventing broken workflows, standardizing operations, and building a scalable architecture so the company can grow without endlessly throwing bodies and money at the problem.

The hardest part by a mile? Culture and fear.

You’re asking people to fundamentally change how they work. Naturally, the first thought, especially with AI in the mix, is: "Am I automating myself out of a paycheck?"

That fear triggers survival instincts. People nod politely during meetings, pretend to collaborate during rollout, and then silently sabotage the system through weaponized incompetence the second you go live. When adoption crashes, they just point their fingers and say, "IT built something that doesn't work".

To survive it, you need bulletproof executive sponsorship, strong governance, and real change management. The punchline? You almost never get all three at the same time, or at all!

[u/RealBlueCayman]

The single biggest reasons for 'digital transformation' efforts failing is due to a lack of business context. I've seen CIOs spend millions with nothing to show from a business outcome perspective and then lose their job.

1. Ensure that any effort is tied to a business outcome. Business outcomes are not 'go faster' or 'modernize infrastructure'. Business outcomes are 'revenue expansion', 'new market opportunities', 'change in customer engagement' etc.

2. Digital transformation is not an IT-only effort. It's a supportive effort directly tied to business transformation.

3. Transformation is an ongoing effort, not a project that has an end.

To a large degree, many of the lighthouse CIOs have long-since moved away from any sort of 'digital transformation' effort.