DiscoverScreaming in the CloudThe Complex World of Microsoft Licensing with Wes Miller
The Complex World of Microsoft Licensing with Wes Miller

The Complex World of Microsoft Licensing with Wes Miller

Update: 2023-09-19


Wes Miller, Research VP at Directions on Microsoft, joins Corey on Screaming in the Cloud to discuss the various intricacies and pitfalls of Microsoft licensing. Wes and Corey discuss what it’s like to work closely with a company like Microsoft in your day-to-day career, while also looking out for the best interest of your mutual customers. Wes explains his history of working both at and with Microsoft, and the changes he’s seen to their business models and the impact that has on their customers.

About Wes

Wes Miller analyzes and writes about Microsoft security, identity, and systems management technologies, as well as Microsoft product licensing.

Before joining Directions on Microsoft in 2010, Wes was a product manager and development manager for several Austin, TX, start-ups, including Winternals Software, acquired by Microsoft in 2006. Prior to that, Wes spent seven years at Microsoft working as a program manager in the Windows Core Operating System and MSN divisions.

Wes received a B.A. in psychology from the University of Alaska Fairbanks.

Links Referenced:


Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

Corey: Welcome to Screaming in the Cloud, I’m Corey Quinn. So, I write a newsletter called Last Week in AWS, which has always felt like it’s flying a little bit too close to the sun just because having AWSes name in the title of what I do feels like it’s playing with copyright fire. It’s nice periodically to talk to someone—again—who is in a similar boat. Wes Miller is a Research VP at Directions on Microsoft. To be clear, Directions on Microsoft is an analyst firm that talks primarily about Microsoft licensing and is not, in fact, part of Microsoft itself. Have I disclaimed that appropriately, Wes?

Wes: You have. You have. And in fact, the company, when it was first born, was actually called Microsoft Directions. And they had a reasonably good relationship with Microsoft at the time and Microsoft cordially asked them, “Hey, could you at least reverse that so it corrects it in terms of trademark.” So yes, we’re blessed in that regard. Something you probably would never get away with now, but that was 30 years ago.

Corey: [laugh]. And now it sounds like it might as well be a product. So, I have to ask, just because the way I think of you is, you are the folks to talk to, full stop, when you have a question about anything that touches on Microsoft licensing. Is that an accurate depiction of what it is you folks do or is that just my particular corner of the world and strange equivalence that gets me there?

Wes: That is our parts of the Venn diagram intersecting because that’s what I spend a lot of time talking about and thinking about because I teach that with our company founder, Rob Horwitz. But we also spend an inordinate amount of time taking what Microsoft is talking about shipping, maybe servicing, and help customers understand really, as we say, the ‘So, what?’ What does this mean to me as a customer? Should I be using this? Should I be waiting? Should I upgrade? Should I stay? Those sorts of things.

So, there’s a whole roadmapping side. And then we have a [laugh]—because licensing doesn’t end with a license, we have a whole side of negotiation that we spend a lot of time, we have a dedicated team that focuses on helping enterprise agreement customers get the most successful deal for their organization, basically, every three years.

Corey: We do exactly that with AWS ourselves. I have to ask before we dive into this. In the early days, I felt like I had a much better relationship with Microsoft. Scott Guthrie, the head of Azure, was on this show. A number of very highly placed Microsoft folks were here. And over the years, they more or less have stopped talking to me.

And that leaves me in a position where all I can see is their actions and their broad public statements without getting any nuance or context around any of it. And I don’t know if this is just a commentary on human nature or me in particular, but I tend to always assume the worst when things like that happen. So, my approach to Microsoft has grown increasingly cynical over the years as a result. That said, I don’t actually have an axe to grind with them from any other perspective than as a customer, and occasionally that feels like ‘victim’ for a variety of different things. What’s your take on Microsoft as far as, I guess, your feelings toward the company?

Wes: So, a lot of people—in fact, it used to be more so, but not as much anymore, people would assume I hate Microsoft or I want to demonize Microsoft. But the irony actually is, you know, I want people to remember I worked there for seven-and-a-half years, I shipped—I was on the team that shipped Windows XP, Server 2003, and a bunch of other products that people don’t remember. And I still care about the company, but the company and I are obviously in different trajectories now. And also, my company’s customers today are also Microsoft’s customers today, and we actually have—our customers—our mutual customers—best interest in mind with basically everything we do. Are we helping them be informed? Are we helping them color within the financial lines?

And sometimes, we may say things that help a customer that aren’t helping the bottom line or helping a marketing direction and I don’t think that resonates well within Microsoft. So sure, sometimes we even hear from them, “Hey, it’d be great if you guys might want to, you know, say something nice once in a while.” But it’s not necessarily our job to say nice things. I do it once in a while. I want to note that I said something nice about AAD last week, but the reality is that we are there to help our mutual customers.

And what I found is, I have found the same thing to be true that you’re finding true that, unfortunately, outbound communications from them, in particular from the whole company, have slowed. I think everybody’s busier, they’ve got a very specific set of directions they’re going on things, and as a result, we hear very little. And even getting, trying to get clarification on things sometimes, “Did we read that right?” It takes a while, and it has to go through several different rungs of people to get the answer.

Corey: I have somewhat similar relationships over the years with AWS, where they—in many cases, a lot of their executives prefer not to talk to me at all. Which again, is fair. I’m not—I don’t require any of them to do it. But there’s something in the Amazonian ethos that requires them to talk to customers, especially when customers are having a rough time. And I’m, for better or worse, the voice of the customer.

I am usually not the dumbest person in the universe when it comes to trying to understand a service or make it do something that, to me, it seems that it should be able to do. And when I actually start having in-depth conversations, people are surprised. “Wow, you were super pleasant and fun to work with. We thought you were just going to be a jerk.” It’s, yeah, it turns out I don’t go through every meeting like it’s Twitter. What a concept.

Wes: Yeah, a lot of people, I’ve had this happen for myself when you meet people in person, when they meet your Twitter persona, especially for someone who I think you and I both come across as rather boisterous, gregarious, and sometimes people take that as our personas. And I remember meeting a friend in the UK for the first time years ago, he’s like, “You’re very different in person.” I’m like, “I know. I know.”

Corey: I usually get the, “You’re just like Twitter.” In many respects, I am. Because people don’t always see what I’m putting down. I make it a point to be humorous and I have a quick quip for a lot of things, but it’s never trying to make the person I’m engaging with feel worse for it. And that’s how I work.

People are somewhat surprised when I’m working in client meetings that I’m fun and I have a similar sense of humor and personality, as you would see on Twitter. Believe it or not, I haven’t spent all this time just doing a bit. But they’re also surprised that it tends to drive toward an actual business discussion.

Wes: Sure.

Corey: Everything fun is contextual.

Wes: Absolutely. That’s the same sort of thing we get on our side when we talk to customers. I think I’ve learned so much from talking with them that sometimes I do get to share those things with Microsoft when they’re willing to listen.

Corey: So, what I’m curious about in the context of Microsoft licensing is something that, once again, it has intruded upon my notice lately with a bunch of security disclosures in which Microsoft has said remarkably littl

In Channel
Download from Google Play
Download from App Store








Sleep Timer


End of Episode

5 Minutes

10 Minutes

15 Minutes

30 Minutes

45 Minutes

60 Minutes

120 Minutes

The Complex World of Microsoft Licensing with Wes Miller

The Complex World of Microsoft Licensing with Wes Miller

Corey Quinn