UnplugIT – IT Lessons Learned From The House of Mouse


With over 25 years of experience leading IT for one of the largest organizations in the world, Tim Aberle shares his experiences on what he shares with every IT Pro who comes to him looking to leverage and experience.

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Hey everyone, welcome to another episode of Unplug IT. I’m your host, Stephen Rose. Thanks for joining. A few quick things of business before we jump into today’s episode. Do not forget about our Microsoft Teams Day on November 30th. I’ll be doing a kickoff keynote and I have a great AMA with Anapam Pattnaik, who is the Senior Product Marketing Manager for Teams, and we will answer all of your Teams questions. I also want to give a shout out to our sponsor, PowerApps 911. I want to thank them so much for all of their great support and everything that they’ve done. Quick word from our sponsor, and then we will jump on with today’s guest.

Thanks, Stephen. Just a reminder to all of you, if you have Office 365, you have the Power Platform. Power Platform is a low-code, no-code platform that lets you build your own apps, workflows, reports, all without writing any of that hard code. If you want to learn more about it, you can go over to training.powerapps911.com. We’ve got on-demand training, we’ve got live training, we’ve got private training, we even have a whole immersive university program, or heck, we’ll even do the project for you if you don’t want to get your hands too dirty. All right. Back over to Steven. Great. I was sitting down thinking while I was in Chicago, about all of the amazing people in this industry that I’ve met, and the amount of fantastic knowledge that they have. I was having some beers with a good friend of mine and said, “Hey, if you could talk to your younger self, or someone new coming into the industry, what would you share?” We had a really great conversation and I thought this would make a great show. So without further ado, I would like to introduce my friend, Tim Aberle. Tim, how are you, friend? I’m wonderful, Stephen. How are you today?

I’m doing really well. For the folks who don’t know you, and I’m going to assume that’s many of them. Tell us a little bit about who you are and what you do, and then we’ll jump into some of your experiences and advice.

Absolutely. Today, I am a principal architect for a Fortune 500 entertainment company that is globally present.

Finishing, actually just starting my 24th year here. Been here a while, seen a lot of change, and a lot of things come along. When I started, I was like a lot of people when they started. I arrived, they said, “Here’s a list of machines you’re responsible for. Hope you can find them. Good luck.” I was a PC technician and took care of everything back in the much more distributed days.

Over the years, as we have grown as an organization, we’ve consolidated operations and done things for optimization. I’ve grown through the ranks up until where I sit today within our enterprise technology group.

Our primary focus, if you will, is to be the IT outsourcer of choice internally, believe it or not. We do operate that way. We are not necessarily a mandated, but we are a strongly suggested supplier of pretty much most of the things that we would think of as non-technically differentiating. Collaborative, end-user compute, mobile, whether that’s email, SharePoint, Teams, voice video rooms. Most of that stuff rolls up through our organization and a good chunk of that rolls up through me from an architecture vision, guidance and roadmap perspective.

I think what’s interesting is in the rodent-themed organization company that you work for is you have every type of industry. You have banking. You have hospitality. You have finance. There is not a vertical that you don’t deal with in some way or another. That creates a lot of complexity as you’re doing IT, working with different levels of access, governance, security, and all those sort of things. As you’re working on projects, I love the fact that one of the first things that you said to me is, when I sit down with a project or a team, what are we trying to accomplish? Who did we get that ask from? Why is that important? I agree. What are we trying to accomplish? You should always do it. I always say, what does success look like? But who did we get that ask from? Why is that important?

I think one of the things we experience as we grow is an understanding of someone said, “Go do this.” They appear to be an authoritative source, so I’m going to go do this. A lot of folks do some very good work, only to get to the point of delivering the solution and find out that the folks receiving the solution aren’t as thrilled as we wish they would have been. It turns out that while we built something wonderful, we built it based on what the IT department of a particular functional area told us their users wanted or what they believed they were trying to achieve. And we’ve sort of missed the context of who are we really here to help? So if I were only building IT systems for IT users, well, that would be great and interesting and certainly challenging enough, but realistically, we’re building things to help the various folks who actually do the work within our organizations succeed.

And sometimes- – Yeah, users, right. – We don’t quite always get that information as cleanly as we would like to, or sometimes the feedback of, hey, that really didn’t work. It’s not at all what we were hoping for. And it turns out when we talk to the users, it worked wonderfully and it was exactly what they were hoping for. It just left a little bit of IT out of the loop that used to maybe be a little more hands-on in some of those situations. – So it’s vision versus reality. So how do you, when somebody has a vision, but you know it’s not the reality. This is not what those end users are gonna want because you’ve worked with them, you’ve heard from them. How do you get IT to really sort of see, get away from what they, how they visualize it, to what it’s actually gonna do and how it’s actually gonna help people?

Yeah, I think one of the first things that I learned along the way when I finally had to leave the lab and talk to real people who were using or unfortunately were being inflicted upon according to them, some of the solutions we were coming up with at the time was, don’t assume that because you approach a compute device in a problem in a certain way that that’s how the rest of the world looks to achieve that challenge. – Works, right. – And so, it’s very interesting depending on the size of your organization, the nature of your company and everything, sometimes those are very matrix roles and we have folks embedded in our business that are supposed to be doing business analyst type work. What is the business problem? What is the nature of the need?

Don’t use a technical term, don’t give me a solution. What are the things you need to achieve? And we also have folks that are more of what we would call in the organizations these days, customer success folks. And they kind of blend over the top where a lot of the business analysts are looking at what’s it gonna cost me? What can I save? Where can I leverage this? What about reuse? The customer success folks are definitely more of the, how do I touch it? What color should it be? Is this button big enough? And all of that matters eventually if you want somebody to adopt what you’re doing. And more importantly, if you want to see that adoption as success, did I achieve the thing I was hoping to do, which was yes, do the financial and the fiscal and the responsible, make it bulletproof, make it cheaper, make it easier, but is it also loved in essence?

And that’s a sentiment and those things are tough to quantify. And so for those of us that tend to look at models and wanna quantify things and look at cause and effect, sometimes the fuzzy logic pieces, there’s no, and I will tell myself this now, and I wish I would have told myself this earlier, there is absolutely no substitute some days for just walking amongst the folks and seeing what they’re doing and how they’re doing it. Cause occasionally you will look at something and go in a million years. I would not have approached it like that, but now that I see how you’re approaching it, I absolutely understand why the solution I provided to you isn’t what you were dreaming of at this point in time. And sure.

I love the phrase, and it brought me back to the movie “Jurassic Park,” which is you spent so much time figuring out if you could do it, no one stopped to think, should we do it? You did a version of this is just because we can, should we? What does that mean to you? – Yeah, I think that is something that, it probably took me the first five or 10 years of my career to stop trying to be the trick pony and ask if we needed. A trick pony. And I think that’s where as I get into rooms, I began to try to simplify this initially for myself, but sometimes for the room as a whole if I’m asking myself, do I understand what I’m trying to achieve and what does success look like?

The first thing I should be able to do from an architecture lens, especially is then sort of pivot back to the quiver of arrows I have, so to speak. And what can I choose from here? Do I have the right size, the right number, because even if I agree with the dream, even if it’s the absolute place we want to be, if I can’t do it successfully with what I have today, then that’s a good point of inflection where we stop. We say, we don’t give up and we don’t say no. We ask ourselves, what are we missing? Because until I can do something, whether or not I should do something is a little bit irrelevant.

And I’ve sat on a number of projects earlier in my career where six months, seven months, eight months into a one year project, somebody is finally coming to the realization that we can’t do what we promised someone we could do seven months ago. And there’s not a lot of hope that we’re going to achieve it in the next three months. So I got a little bit smarter about sort of taking the big things and trying to be a little more prescriptive about smaller bites along the way and points of decision along the way that made sense. If I can’t do it today, why not? And what do I need to be able to accomplish it? Do I need more of something that I already have? That’s one problem. Do I need something unique or different that I’ve never had before?

Different problem yet again, or do I need to work with the folks who provide me the solutions I have today and see about enhancing those? Ideally, the way that’s gonna make both of us happy, it’s going to let me adopt the product the way I need to. And hopefully it’s gonna make it a better product so when they wanna sell it to someone else, this is another use case they can check off. And so the can we problem was really where we would start. And then we’d work past that to say, okay, if we can now, should we do this? And that’s really the lens where I have a lot more fun these days because I have a lot of folks who want to do things all day long.

And yes, those are interesting things. And yes, we could do those things, but what do we perceive the outcome of doing that to be these days? And how do we elevate that discussion into terms that business leaders can follow, IT leaders can follow. And so it’s a different dialogue and it’s not quite the same technical terms
that I may be used to use. If I walked into the room and dazzled with all the words that prove I know what I’m doing, most of you have left the conversation virtually or physically long before we get to the important parts. So that’s a skill I’ve had to work on. Just, okay, you know it, everyone knows you know it or you wouldn’t be. – Right.

Stop proving you know it and start getting the right level of tone and tenor in your conversation. – I think you bring up something interesting and that is to walk away from a project. And I think that’s something that people early in their career are afraid to do because it will look like failure. And if I walk away from this, I might get fired. But if you continue with that project and can’t fulfill it, you’re dragging that out and spending a lot of money. I know at Microsoft, Satya would say very often, if you’re gonna fail, fail fast, learn from it and move on. How did you deal, you know, how did you first, one of the first times, you dealt with it, realize that a project, this is not gonna work the way that people want it to.

And I need to stop this now before it becomes a quick stand, both for your future and potentially financially for the company. How do you get that vision? How do you make that fall? – Yeah, that’s a difficult one. And, you know, for all the reasons you mentioned, I think part of that was, again, the sooner that message becomes apparent and the more readily you’re willing to deliver that message, I think the more simple that message becomes. It’s never easy to go in and tell someone, I don’t think we can do something that maybe I thought we could do before. But I think one of the things I’ve learned to do more effectively, it’s not always received as effectively, but you know, you have to keep hammering it home, is let’s assess and assess often and understand the next step, right?

And I remember this years, years and years ago, one of the first larger adoption projects I was involved in here was, you know, the old perennial, every three years we get a new version of office and oh God, what’s that gonna mean? And I sat down as a participating engineer in a project that someone else was leading at the time. And I thought it was interesting because the product hadn’t officially released. I couldn’t even consume the release notes yet to understand what was gonna change. And when I walked in, the first thing on the board was our two year plan for adoption.

And I thought, well, that was very interesting. How did we arrive at the two year plan? Well, it always takes us two years. We have three months for testing. We have three months for, you know, whatever we find in testing. We have early adopters for three months and then we roll for the rest of the period as we can. And I thought, well, that’s a unique way to look at it. But if you start with the answer and then you keep bending the edges to make it fit the box, that’s probably not the way we wanna do this. – Right. – And instead we kind of flipped it a little differently. I said, what if we accelerate the work in the first two months and then we stop and ask, what do we think this tells us about our ability, compatibility fixes, things like that?

Because if 85% of the stuff just works, that’s a good number on aggregate. But if the 15% that doesn’t work are my mission critical enterprise wide applications, then I’m probably not going anywhere very quickly until we address those. And so numbers on aggregate are interesting, but numbers in particular are really where you need to start forming the message, right? And so then you have to kind of soft pedal that back, right? I can certainly go with the timeline you guys have proposed here, but weirdly enough, if we start rolling this in six months and these guys all have fixes due in eight, I think we’re gonna do a lot of work to start and not be able to go very many places. So what if we propose rolling it in eight and if we can accelerate areas that don’t use these for any reason, they can be early adopters and we can still achieve this and get it in in a year instead of two years.

What do you think about that, right? And some people think that’s good, some people still look at the two year plan. So you’re always gonna have something you need to work around, but it’s not right decision makers and then ideally aligning with the decisions they wanna make as well, right? No senior executive wants to look poor in front of their peers either and they’re trusting you whether they’re saying explicitly or not to make sure they don’t. And so I think that was one of the early lessons is I watched someone crash and burn near me and then the whole time it was like, this is not gonna work, we need to tell somebody.

Well, you don’t disappoint them, but your only choice will be to disappoint them because it’s not gonna work. – Well, and that’s gonna happen. That ranks up there with if you’re gonna do a project, it either has a start date or an end date. You can’t have both. If you’re gonna pick a date, it’s due, then you work backwards, do this, this is when we need to start it. Or you say if we’re gonna start this day, I will tell you where it ends, but you can’t pick a start and an end date. That just, that doesn’t work.

I learned that my first week in business school, one of the few things that I remember, but it served me well. I think along that line, and another thing that you mentioned earlier, and I thought this is great, and this has always been a question for me, which is as I look at, I look at two different types of projects. I look at evolutionary, this is good, here’s what we need to do to make it better, get more people to use it, add updates to it, natural progression. And then there is revolution. Things that are going to change the way that we work, that are gonna take a lot more on the front end, that you may go down a path that doesn’t work, but if they do, they can open up new business opportunities. Along that line of pivot and evolve, which is one of the things that you said when we were chatting. So how do you balance revolution and evolution? How do you balance pivot and evolve?

And just that whole, this is totally new ground, how do we look at that? How do you balance those types of projects or asks, or what are some things that you’ve learned when people come to you with evolution or revolution type asks? – Yeah, I think the biggest thing we learned, and we didn’t learn this organically necessarily.

It was more of a, here’s how we’ve always done it, versus well, okay, then I wanna tip the apple cart if that’s how we’ve always done it. And interestingly enough, in there is a balance, right? And so all change is disruptive. Disruption and change are not necessarily bad, but they need to be understood, and they need to absolutely be bought in, not necessarily from the leaders of the folks involved, but by the people involved themselves. And we chose to be thoughtful here about platform moves. And to be fair, I chose sometimes to be thoughtful, even though it was difficult to stand on that rock as others were throwing things at you.

But if I’m going to disrupt somebody this year, and I’m gonna swap out their office platform, and 70% of everything they work with is going to have to be touch tested, evaluated, and in some cases, remediated, and those are not insignificant amounts of time and effort and money in a corporation our size. And the next year comes the operating system.

Well, what if thoughtfully we choose to be ever so slightly behind on our office platform, while we wait for the operating system platform, and we treat that as a true platform uplift. And one of the kind of watershed moments for us, and I knew I was gonna take it on the chin by saying this, but we did it anyway, is in the transition from the Windows XP to Windows 7 days, we said, “How are we going to transition “the operating system platform, “but we’re gonna transition our version of office “at the same time?” And everyone was shocked. “How could you do this?” Well, it gets worse, people. I’m not only gonna do that, but I’m gonna take my 32-bit antiquated operating system platform, and I’m gonna force everybody into 64-bit.

So we are going to break everything on purpose, and then we’re going to fix things in a meaningful way that’s gonna buy us another five or so years to go deal with the outliers and the stragglers. And it absolutely meant making some unpopular decisions. My really old 16-bit apps didn’t have a path forward anymore.

My people were not thrilled. But the alternative was, you can stay where you are, but not for much longer, that’s end of life. And so that became a debate of how much is too much, or how many times do we wanna reassess the same real estate? And in the end, it was a challenge. It was a little painful. We certainly heard our fair share of, but everything’s broken. Yeah, but think of all the fun. We can have a project over one year and fix it all, and be good again for a while. And that was one where it really came down to my belief in something that I was able to prove out as a cost benefit only after going through it, right? And it was a little bit of historical data of what does it generally cost us to go through one of these efforts.

I’m gonna do this once, add maybe three months to it, instead of doing it three times over five years at triple the cost.


It’s interesting, because I know so many companies, because I led our Windows 7 deployment and did that XD to Windows 7 in 30 minutes off a USB stick using USMT and things like that. Thank you Jeremy Chapman again for helping me with all that.

What was interesting was a lot of companies chose to do the OS and the Office 2010 at the same time, saying they already have stuff to learn. We may as well just throw in a little bit more with that. And I will tell you, the companies that did the OS in Office at the same time were actually more successful than the ones that drug it out, because people said, well, I gotta learn this just to get my job done. And everybody was at the same place, rather than have this sort of staggered thing where users somewhere ahead and somewhere behind, and it just created a lot of angst around that level. So as you look back, was that the right decision?

What would you have done differently as you were facing Windows XP end of life, Office end of life, and all that server end of life were also hitting at that time? There were a lot of things that were changed. The cloud was just starting to come in. What is something that you might do differently today? And I’m not saying that you have regret, it’s just again that experience, whether it was a process or the way that you looked at something.

Yeah, I think, like everything, some of the best designs I ever came up with at the moment in time, I thought they were the best designs ever, or some of the most tragic ones I review today, but they were the best things we could do at that moment in time with what we had available. And I think that’s a good one to remember, right? I am as critical of things I did in the past as I’ll probably be of things I’m doing right now in the future, but sometimes you get to a point where you have to say, “Okay, this is the best I could possibly do.” I think in retrospect, the one thing I probably would have done, and this is where I picked up a lot of this, is we were trying to make this an IT, an IT to IT leadership push. And so enterprise IT was driving the change, all of the corporate IT segments were saying, “Oh my God, what is this gonna cost us?” And early on, we didn’t really look for that, I’ll call it that tiebreaker moment.

What was very interesting is at one point, I sat back with one of our project people at the time who said, “Yeah, yeah, yeah, we’ve been through “24 slides here, I don’t care.”

But there are 24 slides, we worked a long time on those, and it’s got a great message about what works and what doesn’t, and what do I get out of this was her exact quote.

Well, what do you mean? Why should you get something out of this? This is just something we have to do. I mean, things are end of life, we can’t keep them forever, we have to move.

But why? Why would I want to move? – Right, what is the benefit that I will personally see, the with them, the what is in it for me? – Exactly, and the sad thing was is we were at a bit of a log jam with a couple of our larger segments on, “Well, you know, we can go to the board “and we can vote on this, and if it’s five to five, “tie wins, we get what we want.” And it’s like, nope, that’s not really one of these moments. So she happened to mention one of the coolest things that she saw five seconds after she saw it was one of the things I thought, well, that’s just silly, snap in Windows 7. – Yeah. – The minute she could just drag two windows and boom, Excel spreadsheets in multiple windows now, the combination of Office and Windows 7 together, she immediately said, “That’s gonna help me get my work done faster. “I want that, who do I talk to?”

Right. – And so we turned around and realized again, the actual group we were solving problems for wasn’t the other IT group after all. It was the folks who were gonna have to consume this change. And I think that helped validate the concept that you were mentioning, which is, do I feed change into this pipe continuously to the point where it’s just never stopping and people get tired? I don’t want the next thing, I like the thing I have. Or do we do it reflectively and thoughtfully in chunks that are consumable, but also have something in it for the end user community directly? It’s like, I want this thing.

Who do I call? Where do I send my leader to ratchet up the pressure on my IT folks? Because if you’re telling me I can’t have this because my apps don’t work and these people aren’t willing to do anything with those apps, I’ll go fight that battle for you. And suddenly I had a lot less battles to fight. I just needed to arm people who were willing to fight the battles with the things they needed to make their business cases. – But then you have the other side of this, which is something, let’s say like co-pilot where companies are like, give me, give me, give me, I gotta have that. I saw this great cartoon, like, you know, all these things that co-pilot, you know, could potentially do or AI can do. And they’re like, so why do we want it? It’s like, I don’t know, but everybody else has it and they wanna have it. It’s gonna be this great game changer, but we can’t prove it.

I had a great chance while I was in Orlando in Chicago to talk to folks are like, yeah, we want co-pilot. I’m like, okay, what are you doing to prep? What research have you done? How have you cleaned your data? How will you train your end users? You have to buy 300 licenses. So you have all of these things that you’re gonna have to do internally to prepare to make that work. We also have, what is it? 70% of employees are now using co-pilot. 40% are putting confidential or not co-pilot, but chat GPT, 40% are putting confidential information in there. So you have that other end of the spectrum where people want it, but they don’t understand what goes into it and why you don’t just wanna jump feet first into some technologies.

You wanna do your due diligence and go through. So how do you separate those moments and how do you convince somebody, I know you want this because they’ve read the hype, but is this really gonna do what as advertised the way that people expect it to? How do you set those expectations for someone or say, you need to take that down enough? That’s the market too. – That’s become the greatest challenge for I think a lot of folks in my position in the last three to five years, as we’ve, in quotes, democratized IT, we haven’t democratized risk and responsibility.

And so for us, it’s kind of, let’s take it away from the, no, you can’t have the candy conversations again and try to get in front of the, what is the potential risk and what is the liability?

Because most of the core of IT today, and especially in my level, is really about measuring risk and liability and compliance, because we don’t operate a lot of the same systems we use to operate, there’s services in a cloud for us. And even if we wanna understand what they’re doing, a lot of times it’s, oh yeah, we have a website, go there, look, we filed a form. And so, I think where we’ve transferred time and energy in, did you set it up right on-prem? Did you configure it right on-prem so that you as the custodian of this environment have successfully indemnified yourself? I mean, we had networks, we had firewalls, we had data centers, we had all these things, and we understood those concepts, right?

Now we’re translating those things into behavioral constructs, which are always a little more interesting. But I think one of the funniest things for me was when Autopilot first launched, well, you have to have Autopilot. If you don’t have Autopilot, you’re not modern. If you’re not modern, you’re gonna die on the vine and you’re not successful.

Okay, does it matter if it works? Well, that’s irrelevant. Every book out here, every CIO weekly, every everything says, this is it. And if you’re not doing it, you’re left behind. And we spend a lot of time- – It’s kind of like metric system, which by the way, all we use it for in the US is soda. But I was terrified that somebody would get hit by a car, need a hectoliter of blood. I wouldn’t know how much that was. And that person would die. This 1977 junior high, and I was terrified that somebody was gonna die because of my ignorance of the metric system. Again, soda. I know one liter’s good, two liters goes flat. That’s it. – Yep.

And that’s kind of it in a nutshell. I mean, part of these are conversations that have become very technical and very complicated. I can’t move a slider in one system and have it just affect one system anymore. And that’s if you even understand what moving a slider means because it’s nice that we have a fuzzy UI that a tech can go and drag some levers back and forth these days, but there’s no measurements in place for a lot of this to actually judge the outcome of what you’ve done. So we’re getting into those moments. And again, I think this is more of that, that revolutionary slash evolutionary and the change friction. Some change friction is noise, right? Somebody says, but I love this browser. I can never browse on anything else without it. If it doesn’t have this letter or that letter in the upper left corner, the internet will stop running tomorrow.

Okay, tech religion, right? There are other things where we can literally say, look, once that happens, it’s the door open, the hen house and the fox. If the fox is in, eventually you might get the fox back out, but the damage that’s done may be unrecoverable at this point. So maybe we should pay a little more attention. Maybe we should learn a little more. And I think you’re always gonna have that. I’m in an industry, as you mentioned earlier, that is so diverse and so unbelievable. We are doing cutting edge patenting on technologies on one side. And I’ve got folks that are still trying to figure out why 8-bit isn’t the answer.

Clear somewhere in the basement somewhere. And so it’s always been that challenge, right? I’ve got to keep those who want to run with scissors corralled enough that if they do fall occasionally, they don’t harm themselves irreparably. And at the same time, we’ve got to circle back and keep pushing the butt end of the elephant and going, you got to move. We’ve stretched the ridge as far as we can. You got to move. And I think it is a little bit of art and science, but I think in the end, it’s communication and understanding. And so my audiences are incredibly varied. Some are very technical, some are very process driven, some are very financially. So part of the secret, I think, and it took me a while to get there, is how do I make this relatable to them?

Which part of the problem statement is their piece of the pie? And then ultimately, if theirs is the fiduciary decision, I can educate, I can arm to a certain extent with, things that might catch you and slow you on the way out, but ultimately, even if I bolt the door and you’re intent on getting out, you’ll crawl up to the next level and find a window and go out or you’ll do something else. So if I’ve educated and I’ve, to the extent that I can protect it, then I indemnify and it’s literally, if you guys are the fiduciary for this, you sign off on it, then I can’t stop you, I can strongly encourage you not to do that.

What will stop you is when something goes wrong and that’ll be terrible because ultimately, I’m both a fiduciary of this company and an owner in this company. And so I am protecting my investment as much as everything else around this company. And that’s how I think we continue to reeducate is we rehome the conversation on, not morbidly what could go wrong, but if this situation arises, what’s our plan to recover?

And that forces folks to start walking through some of that and eventually the light goes on and they go, well, wait a minute, how would we get that back? You know, it’s gone. So, that has become a lot more of my technical job these days in a technical role. It’s more soft in people skills some days and it’s trying to keep up, you know, the amount of change that’s happening at the rate it’s happening and in a manner or method in which, you know, most days I’m happy if I can find out within 24 to 48 hours that something new is loose in the world, you know, we used to have months to prepare. So, it’s a new world.

Something interesting and this is, I guess, probably my final question because we’re starting to run out of time, but I think you and I were at Ignite or Inspire, one of those in Atlanta. You’re having beers and just sitting and chatting and hanging out, it was a nice day. And you said something that really affected and it’s something that I have kept in mind and made part of my talks and that, and that was, we were talking about the role of IT and you said, I think the most, you know, I asked him like, what’s the most important thing as I’m working with IT pros?

I’m working with, you know, heads of IT, et cetera, to think about and you said something that really struck me, which is, it’s really important to understand what happens before and after your experience. And I said, what do you mean by that? We have to know the people who are handing you these projects, what are their expectations, but also the folks on the other end, who are the people that are going to hand this off to you and who do you hand this off to?

And understanding that, not just working in this bubble and building that bridge between them is a critical part to success. And I’ve really taken that and really looked to, if I’m gonna teach you how to use a piece of software, what are the things that happen before it gets to you in your process and what are the things that are gonna happen after the process? And even as training, it’s really important to say, hey, when you hit send on this, this is what’s going to happen. And if you’ve received this, here’s what’s happened up to this point. It not only humanizes the process, but also gets you to better understand cause and effect.

And that has really stuck with me. And I thought kind of as our closing thoughts, if you could comment on that and what brought you to see things that way? How do you look at that before and after your role and help you to better define what success looks like for yourself? – Yeah, I think the first realization I had with that is when the jobs that I was performing as I grew in the company, eventually got to be more than I could do all by myself. And I think that’s a critical learning curve for a lot of folks because for a long time, I was the designer, I was the engineer, I was the tester and to the extent that I could push a button and make it go without anyone else stopping me, I was also the release vehicle.

And I also had instantaneous feedback because they were all my systems. If something went haywire, I was the first to see them and probably the second to get the phone call. So that closed system sort of ability to say, I understand where it came from, how I’m going to consume it, what I need to do to sort of push it out in the world. And most importantly, how to figure out whether or not what I did in the console turned into what I hoped to achieve on the endpoint or the mail system or the, hey, I changed routing rules. No one’s getting mail. Oh, that was a bad idea.

Now right after that, you should have said, why did you change routing rules? And then more importantly, what was it you hoped to achieve by changing the routing rule and sort of walk that, right? And this is something to this day that I still walk into. It’s, I sit in a lot of design review sessions where someone says, here’s what we’re going to do right now.

And we go, great. It’s like a wonderful thing to do right now. What happens in a week when we hire new people, when people leave the company, when we need to transition this configuration, if we need to walk back from this.

I thought it was interesting and I learned this years ago in a prior life in the aviation industry, but we did firefighter certification and it was one of those things that seems like common sense until someone says it out loud. It was never fight a fire going into a room where you don’t know how to get back out.

I know you don’t race in and then look around and go, “Oh God, what would I do?” It’s a meaningful approach with some thought into it. And sometimes it’s a matter of saying, it’s not all ones and zeros, right? Someone has to go request this item. How do they do that?

What would I do if I started this process and I had to go from I’m the requester to I’m the fulfiller, to I’m the technician, to I’m the notifier, to eventually I’m that same requester again and now I’ve been notified and does that make sense to me?

Because not all of that does. How did I know you were done with the job? Well, we sent you an email. You sent me an email. What was I requesting? Well, an email account.

I see.

How would I have received the email? – Receive that, yes. – Or the account. – Yeah, keep working on it. Hit one to continue the back from the DOS days and the early XP days. – Exactly. So I think that’s something. Yeah, that’s something it took me a little bit of time to say because for a lot of us, we’re really busy. We have a lot of stuff thrown at us. It’s always overdoing late when it gets there. You need it by five and it’s 4.48.

So, sometimes it’s tough to have that ability to say, I need some time to just say somewhere in this plan, somewhere in this adoption strategy, there should be a point of reflection where again, we try to measure what did we intend to do and how do we prove that what we’re about to do will achieve that. And some of those are soft things, surveys, whatever. Some of those are very tangible things, but kind of leaving it on this note with someone, I was having a rather spirited conversation where I thought we were getting to the point and we kept going backwards the other day.

How do you know what you did was right? And they kept pulling up the console. They were configuring and showing me the screen. And I said, no, I understand what you’ve set in this screen you’re looking at appears to be what you wanted to achieve, but how do you know it worked?

Well, because, and then they kept falling back to the screen. I said, okay, let me make this easier.

This is going to change a configuration on a Windows endpoint. Yes. And it’s a fairly important one that we make sure happens. Yes.

Do you have a Windows endpoint?


Okay, that’s our first breakdown. Do you know someone that does? And more importantly, after targeting it to this configuration, how can we verify that that actually happened? Is it pull up a screen and the button went away? Is it dig into the registry and private number? Functionally, you’re doing this for a reason. What is that reason?

And how to improve that it worked. And I think that today, because so many people do just a piece of the puzzle anymore and there’s not folks like it was when I started out that were responsible for it, and it’s a cradle to grave.

Their part is push this button, I pushed this button. How do you know you were successful? Here’s a screenshot to prove I pushed this button. Now it proves you did what we asked, it didn’t prove that you were successful.

Absolutely correct. Yeah, it’s like, I went to the store but you didn’t bring home the milk. Yeah, you got to actually follow through. And follow through is key. I think, and again, I think this really hit it on the head for me is what happens for what happens after. How do you show that things work? How are you connecting with your end users and getting feedback? It’s a constant circle. You’re never done. People and people enter that, that cycle at different places and it’s keeping that in mind. This is absolutely true. One final bit of pearl or bit or saying or thing that has helped you throughout the years. And then we will close our conversation out.

Yeah, I think if I would just finish the sort of the three pillar that we’ve alluded to before, I fall back a lot on that. It’s the can we, the should we and then ultimately the will we. And I think the will we can be incredibly discouraging every now and then because the will we do something can be the least meaningful set of attributes that are applied to it. And one of the things I saw a long time ago here is I can do something. I can demonstrate that I can do it. I can even rally all of the data that proves that we should do it. But then ultimately it gets to layers much higher than all of us for the political will, the capital will, the, you know, whatever it is I need to green light this and finally get it done.

Will I do this? Even though I know it’s something I should do, even though it’s something I can do and I’m lobbying for it. I wouldn’t have spent all this time and effort on it if I didn’t think we would do it, but somewhere near the very end of that process, someone pulls the funding or someone says, “Wait, I just realized this could affect me personally. “Now I’m no longer behind it.” And, you know, understanding when you get to that point that if you’ve done everything right, you’ve positioned it right and you’ve done your job, unless you’re the king of the castle, so to speak, sometimes it just doesn’t get done. And, you know, how to internalize that, not as a failure, but as a challenge to figure out how do we do this next time? – Yeah. – You’re the organization.

Yep, the bigger the organization, the bigger the animal you’re trying to tame. And, you know, sometimes the tiger bites back, so.

  • Awesome stuff, I love this. Tim, this was great. Next round is on me. Next time I see you for taking time out of your schedule or several rounds as it usually ends up with you and I, which is always nice.

Where are you off to next? Tim enjoys traveling much the same way that I do. Anywhere interesting you were off to next? – Yeah, we are actually in about a week and a half. We are headed to London for a long weekend to go see a Tottenham game. So I have seen NFL games in that stadium, but I have yet to see a Spurs game in that stadium, which seems kind of backwards, but, you know, the stars will finally align.

I think that will be awesome. I want to take a moment and thank everybody who showed up at my sessions, both at Ejikon in Chicago and showed up in Orlando. So great to see all of you. Met so many of you that told me you’re watching the show, liked the show, loved the show. Thanks again for watching. Thank you again to my guest, Tim Aberle. We will see all of you in the next episode of UnplugIT. And once again, do not forget about our Teams event on the 30th. We look forward to seeing you all there. Thanks again, have a great day, and we’ll see you all soon. Take care.