How do you know that your digital transformation is going to be successful?

2.9k views2 Upvotes8 Comments

AWS Enterprise Service Manager - Global Accounts in Software, 10,001+ employees
There isn’t really a great metric to say, "Hey, this is really working out or not." There's some things that just don't work out that you've got to pull the plug on. Can I tell you when you know that this is the right time or not? Not really. Each project, each engagement's a little bit different in how you go about doing things, but the worst thing you can do is be paralyzed by indecision. We always try to do things as a two way door. Usually if you embrace it and you get the right team, and you get a few projects under your belt, you know how to operate and you can make sure you have two-way doors. That way you aren't going through a one way door and you can't get back out. Make sure that when you're making decisions and you're moving forward, you can come back out that door to course correct and move quickly forward. I don't know if there is a good way to say, "Hey, are they just going slow and taking advantage of this new freedom and independence to operate independently." That's why you do have some leaders in place. If you can get some people who have done this practice, you can tell pretty quickly what's succeeding and what's not from that standpoint, but it's a delicate balance. You still need to keep an eye on it. What you can't do is paralyze people to not have any action because that's the worst thing. It's not really a science. It's kind of an art.
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VP of Products, 201 - 500 employees

One thing that crystallized that for me was when one of my mentors told me that not making a decision is a decision. It's a decision to do nothing, to leave the status quo as it is. And that really helped me think about the speed at which we make decisions. If we waffle on it, we're deciding not to take a risk or more likely we're deciding not to take smaller risks while we're taking the bigger risk of fading away into irrelevance as we fail to adapt to the changing circumstances around us.

VP of Products, 201 - 500 employees
We've been talking a lot about empowered teams who are free of some of the executive involvement in daily activities and how we balance that as we start holding those teams accountable for their outcomes. OKR's have gotten super popular for this kind of approach. How do you give that team enough freedom to execute as they see fit while still ensuring that they are delivering value? All these teams have been out there doing stuff, but you need to know if it was the right stuff. How do we even know? And the other piece of it, and this is maybe less interesting, but a lot of larger companies have a huge number of handoffs involved to get work from idea to customer. Every time we are able to speed that up by giving people things that a product team can consume and build upon rather than handing off work for the next step, that results in a dramatic improvement in our ability to innovate more quickly. For example, we did this huge Valley stream app. We found out that if you want to get a new application into production there are 72 different steps you have to take, and many of them were invisible. The teams keep requesting more and more things (firewall stuff, opening ports, getting an IP, getting the VM installed on the server, getting the middleware installed on the VM, etc). It stacks up until the point you're a mummy and you're wrapped in bandages and you're trying to move, but you just can't.
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AWS Enterprise Service Manager - Global Accounts in Software, 10,001+ employees

If you really do embrace a new way of doing work and you put in the mechanisms around the weekly sprints and the retrospectives, you're iterating. It is amazing to me, some of the stuff that we'll roll out just to get feedback quickly and iterate. And then a week later we come out and have improved a part of that. That's one way that we really pay attention to measuring things as well. And we always start with the customer. You always have that customer centric view of what you're doing and why you're doing what you're doing. And if you stay with that as the focus, usually you don't go wrong and you get to where you need to be. It is a different mindset in how you go about it. It doesn't have to be perfect starting out, but get it there, get the feedback, iterate on it. And then you get a  real-time measurement of success. If you're just going slow and not getting stuff done, it's immediate and you see it, and you have to step it up. In the old way, we spent 9 months to a year before we got any feedback.

VP of Products, 201 - 500 employees

I totally agree with that. The only person who can tell you whether you built the right thing is the customer who's going to buy it.

AWS Enterprise Service Manager - Global Accounts in Software, 10,001+ employees

That's the beauty of what you've seen in the transformation. I mean, you look at just how we consume apps on our phones. How many stars do we give it? The first thing we do before we download an app, we go read the reviews on it. It's really changed the game. Immediate feedback has really changed how we view success as well. If you're not four or five stars and I see some three or two, I won't even consider it a lot of the time. I'll read a few reviews and then all right, done. Let's find the four or five starred one.

CEO in Services (non-Government), Self-employed
Use a value metric: delivering more value to customers, faster, and at lower cost which measured by either  Time-to-Value (TtV), Time-to-Decision, Conversion, Time Engaged....
Chief Information Officer in Manufacturing, 10,001+ employees
With executive Leadership Buy-in and Mandate our digital transformation will be successful

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