Welcome to episode 191 of the Nerd Journey Podcast [@NerdJourney]! We’re John White (@vJourneyman) and Nick Korte (@NetworkNerd_), two Pre-Sales Technical Engineers who are hoping to bring you the IT career advice that we wish we’d been given earlier in our careers. In today’s episode we share part 1 of an interview with Brett Hill, detailing his entry point into the tech industry as a trainer, becoming an expert in a specific technology, tips for presenters, and growth through technology changes.

Original Recording Date: 09-06-2022

Topics – Meet Brett Hill, The Wave Rider and Early Tinker, Becoming an Expert, Evangelist and Course Builder, Scaling up at Microsoft, Presentation Tips, Growth of Self and Shifts in Technology, Microsoft to Riverbed

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3:34 – Meet Brett Hill

• Brett Hill is currently a coach’s coach, teaching coaches how to better serve their clients – stressing topics such as being mindful and present, good communication, and specific somatic techniques for personal improvement.
• Brett’s career began in the tech industry, and he got started doing technical training in the Microsoft stack.
  • Brett had reached a decision point between Microsoft and Linux technologies in the days when Microsoft was fairly large but not nearly as large as they are now. At this time enterprise technology did not exist as it does today but rather was being created.
  • A friend of Brett’s gave him a disk with Windows Server on it, but at the time he didn’t know what a server was.
  • Brett was decent at computers from working on them for a retail store chain. This was before IBM personal computers (PCs).
  • Once PCs really caught on, he was one of the few who knew the technology well from working on them before they became a thing.
  • Brett got out of the record business and went to work for a computer store that sent him to an Apple II training to learn how to repair these type of machines. He later became a manager of some computer stores in the service technology / computer repair space.
    • This led to working on IBM computers.
    • Brett was eventually hired by Compaq (which was acquired by HPE later) and served as the national technical support manager for a division that was ahead of its time and didn’t really take off.
  • It became clear that PCs were going to be a thing for businesses and that Microsoft was going to be a big player.
    • Brett decided to focus his studies on Microsoft.
  • At this time the internet was not quite what it is today and still emerging technology. Brett was looking at what was going on with server technology, and no one seemed to be focusing on web server technology.
    • Brett shares the story of Microsoft developing WINS (Windows Internet Name Service), how Microsoft was thinking about the early days of the internet, and needing to focus on these kinds of topics in order to go deeper on web server technology and develop Microsoft expertise.

7:49 – The Wave Rider and Early Tinker

• As an aside to the above story, at one point through a series of strange events, Brett ended up owning 5 different used record stores during his mid 20s.
  • Brett remembers this time as a lot of fun. But he also remembers seeing computers pop up during this time.
• After wondering if the computers could be programmed, he wrote a point of sale system for the record stores to use to organize records, track inventory, etc.
• Nick makes the comment that Brett had business ownership experience, experience with inventory management, sales experience, and he was also riding a technology wave of personal computers (a pattern we are seeing with other guests).
• Brett considers himself a little bit of a futurist, looking across the industry at what he believes will be big.
  • Brett is at an age now where he can’t really get on the horse and ride it for 10-15 years but can point out the race that will be interesting.
  • Brett tells us that he has done a lot of very interesting things in technology.
• When he was younger, Brett was always interested in how things worked.
  • He shares the story of rewiring the lights in the living room at age 10 to turn on / off based on a toy tank coming into contact with aluminum foil.
  • This was almost a form of architecture. Brett would take a room and figure out how to integrate it with his stuff.

11:27 – Becoming an Expert

• When looking to develop expertise / be known as an expert in something, Brett would analyze the broad technical landscape and look at who the key players were.
  • This approach can be generalized for anyone listening who might want to become an expert in a specific field (robotics, artificial intelligence, virtual reality, etc.).
  • At the time Brett was initially developing his Microsoft expertise, there were already voices popping up around Microsoft Exchange Server and Windows clients, for example.
  • Brett was a Microsoft Certified Trainer and was teaching on Internet Information Services. But the curriculum was awful.
  • Brett has a degree in interpersonal communication with a certificate in secondary education. He had been an actor, musician, and a public speaker in high school and college.
  • Brett was well suited to take the course that was not so great and make it interesting to students.
    • "That’s what a good teacher does. You take the subject and you make it alive for people." – Brett Hill
  • People responded well to the change in course format /content. At this point Brett began to make a name for himself for being able to teach this specific class on Internet Information Services (IIS).
  • When he looked around, Brett didn’t feel like anyone was the voice of the technology he taught / a voice of the specific expertise. He decided right then to own it.
    • First, Brett decided to find every piece of information possible about the product (IIS).
    • Brett had no practical experience with the product in terms of making it work for a company, but he spent a lot of time figuring out how the product worked, tinkering with it, and determining if it did what all the documentation said it did.
    • Brett decided to hang his hat on "I won’t tell you it is so unless I’ve tried it." He would steer his students clear of product screens and areas that he knew did not work and would back it up with proof.
  • As a result of the work vetting the product, Brett decided to write his own course and was hired by a number of companies across the country to teach IT engineers and administrators at these companies how IIS worked.
    • These companies (including some of the top insurance companies in the world) as a result of Brett’s position as instructor would share their architecture, plans for implementation, and how they operated the technology.
    • Brett was able to synthesize the way these companies were using the technology and things that worked / did not work into a set of best practices that went back into his training.
• Nick cites teaching as a way to show expertise on a topic.
• The opportunity to be a trainer came about because Brett was publishing content.
  • He had a website called IIS Answers. Because no one was publishing similar content it was very easy to find.
  • Brett would publish FAQs (frequently asked questions) on his website which became popular search results.
  • For those who want to develop expertise, find the FAQs and write articles on them. Put them on a website that is backed by information you know is right (backed by testing), and make it easily digestible so that when someone searches for the information there is a good chance they are directed to your site.
    • You want people to read your site and know you know what you’re talking about.
    • The field was not as crowded as it is today, and there were lots of places to hang your hat.
• Brett would later pivot to Office 365 as a focus using the same formula (details to come later).
• What about people who don’t feel they have expertise in one area? How can they decide what to specialize in?
  • Start with what you like and what you know.
  • Think about what you’re good at doing. Brett liked things apart and liked to tinker and test in a lab.
  • "It’s not just about knowing the technology. You have to make it relatable." – Brett Hill
  • Making things relatable is not a skill set that everyone has. If you don’t have this skill set, you may not be well suited for a public facing role like what Brett was doing as an instructor.
  • Perhaps you’re well suited to do troubleshooting for a company like Rackspace with a large number of servers (and needs people who can work on these servers – deploying them and figuring out what is working / not working).
  • When you own a niche you can really demonstrate competence there that has value.
  • But you have to decide what you like doing / what you could see yourself doing.
    • Do you like wiring things together or taking them apart?
    • Do you like architecture pieces of getting services to communicate or writing the bits that connect them?
    • Maybe you’re interested in authentication or maybe you like Wireshark and going deep into networking protocols. Network troubleshooting is a very valuable skill.

19:59 – Evangelist and Course Builder

• All of Brett’s IIS content got Microsoft’s attention at some point.
• Brett was also invited to speak at conferences as a result of his expertise. This allowed him to meet a number of people like Mark Russinovich, Don Jones, and several others who were speaking at these same events.
• Brett was traveling a great deal, doing presentations, and writing quite a bit. As a result, Brett was awarded the Microsoft MVP Award several different times for his work on IIS.
• One day Brett received a call from Bill Staples (current CEO of New Relic who was then program manager for IIS). Bill asked Brett if he wanted to come work for Microsoft as the technical evangelist for IIS (no interview, just straight up asked).
  • Brett thought for a second and decided to take the job, giving up his training business and moving to Redmond to work for Microsoft.
  • Brett was then doing Microsoft’s IIS training and personally wrote the next version of it, which won awards and was extremely well received.
• Nick says most people most likely do not understand the level of effort that goes into preparing a course to teach.
  • Brett says building a course takes a lot of work, and one of the keys is the labs.
    "Talking gives people ideas, but they have to do it to make it real." – Brett Hill
  • The labs are what take all the prep work. It’s easier today because of virtualization technologies (on-demand labs that get destroyed when someone is finished working on them).
  • It takes a lot of work to make sure everything functions correctly every time. Having 20 people in a room means there will be 20 different ways people will try to do something (with each learning differently).
  • You have to be precise in your language and very patient with people since they learn differently.
  • There is a teaching element here too. You have to be able to help people learn in ways you don’t.
    • Nick calls this meeting the learner where they are.
    • One example Brett gives is using language like "enter your computer name where your computer name is the name of your computer." Otherwise people would type in "your computer name." These kinds of things needed to be spelled out every time in every lab because you are probably dealing with some who will take you literally / have little to no knowledge of the subject coming into the class.

24:52 – Scaling up at Microsoft

• It’s hard to paint a clear picture of what having a job in a huge company like Microsoft was like.
  • It’s hard to comprehend the scale of things if you have never worked at a company like this.
  • To give an example, Brett was asked to create a course that could be used to train web hosting companies on IIS (big consumers of web servers) since Microsoft has a vested interest in those companies knowing what the latest technology is.
  • Brett started to work on the course, but other people were working on the logistics of scheduling and delivering the course.
  • Microsoft wanted to host this training in 24 cities around the world and train around 2000 people.
  • Brett was used to teaching 20 people in a room and found himself on a multi-million dollar project. It was tough to get his head around the size and scale of this.
  • It’s hard to think big enough in these situations. Large companies like Microsoft relish people who can think big and take risks.
• During all this, Brett never found himself stricken with impostor syndrome. He feels like maybe he should have but always felt up to the task at hand.
• Brett merely needed to adjust his mindset for the task at hand, whatever it was.
• Speaking engagements outside of delivering the training were not specifically required, but it was a natural extension of Brett’s role. He was invited to speak at a number of events because of the expertise he had.
  • In conference talks he would speak to what was coming and why it mattered, and he would rely on his technical chops from doing the training to show off a demo of how something worked.
  • Brett built a reputation of developing presentations that contained a number of live components.
  • It was important, risky, and hard all at the same time.
  • Brett would often have a video backup ready to go just in case the demo he wanted to show did not work live. There are so many things that could potentially go wrong when doing a live demo, and we need to be prepared.

28:55 – Presentation Tips

• The recording of this episode took place shortly after VMware Explore US 2022. What tips does Brett have for someone going back to presenting at conferences (or those who are doing it for the first time)?
  • When presenting you need to pay close attention to the audience while you are talking. This means making eye contact and speaking to them as if they were sitting at a table with them.
  • Make it conversational and personal. Help your audience understand why what you have to say matters to them.
  • "This widget is going to help you in your job. And here’s how I know that. Let me show you." – Brett Hill
  • As long as you can deliver, the audience will like your presentation.
  • You have to be confident, and you have to know what you’re talking about.
  • Brett sees many good presenters who don’t take questions well. Audiences can often time be confrontational and take you down paths you did not expect. You need practice dealing with unexpected scenarios.
  • This is where mindfulness can be very helpful for presenters.
  • Be aware how much the answers to questions matter to the audience, but don’t allow it to sidetrack your message or throw you off your game completely.
    • It’s ok if you address the question by suggesting there isn’t enough time to answer it and that a deeper 1-1 conversation is merited after the presentation is over. Use phrases like "I’d love to talk to you about that after this is over."
    • Connect with and make the person your ally if you can, and then move on. People will hog the spotlight if they can.
    • If someone is hogging the microphone at question time, you have to take it from them…gracefully or possibly ungracefully.
    • As a presenter…"You’re in charge. You’re the boss. Own it." – Brett Hill
    • It’s a little bit harder to own it when doing a remote presentation because you do not have the authority of the physical stage.
      • If you’re on stage, everyone is looking at you from where they sit. In a remote presentation, your video is often the same size as everyone else’s. It’s a different sort of mojo.
• Practice until you feel really comfortable with the presentation. Practice to the point of confidence you can handle it when nerves arise.
  • Brett did his IIS training 100 – 200 times. Not until he had done it about 20 times did he understand a specific rate and rhythm really worked well. For example, he might know that a concept really sets in well on day 2 as opposed to day 1 because other concepts covered later help with that understanding.
  • When doing a presentation, you can stage this kind of thing (i.e. refer to something you spoke about before really becoming amplified at a specific point). Audiences appreciate this, and it makes them feel like you’re taking them on a journey.
  • Practicing your presentation in the room where you will give it can help you remember it better. Even smells can help you remember things.
  • Also, make sure you know if you will be able to access your notes during a presentation. Brett prefers to carry a backup with him.
  • Brett reached a point in his career where he did not need notes. He used the PowerPoint as his notes with bulleted items serving only as a reminder of what he needed to talk about at a specific time (i.e. bullets served as triggers).
    • If he lost track of where he was during presentation flow, the information on the PowerPoint slides would help him course correct.
    • As long as you can see the slides you can stay on point.

35:12 – Growth of Self and Shifts in Technology

• Brett says he was well prepared for doing presentations due to his background, but he learned a great deal too. At some point his desire to understand how things work turned inward and onto topics like how the operating system of Brett Hill works. Brett wanted to know…
  • How his brain worked
  • What his emotions were about
  • What was really happening when he gets upset (i.e. what was really going on at a deeper level)
  • The architecture of his inner topology and how things were wired up to work together
• The inquiry within began in parallel with his technical career. He began to study meditation, somatic psychotherapy, mindfulness, and a number of other things that informed his capacity to be present with people in a way that would not otherwise be possible in personal and technical conversations.
• At Microsoft, Brett made a move from technical evangelist to partner technical readiness manager for what became Office 365, which is now Microsoft 365.
  • Brett highlights the transition from installing software from a CD that you bought to paying a monthly subscription fee for software as well as the birth of services that live only in the cloud.
  • There’s also the transition from distributing software using disk media to distributing it via download.
  • Microsoft partners were responsible for selling Microsoft product offerings (i.e. licenses) to businesses, which could be software that is installed on a server belonging to the business or hosted elsewhere (could be Windows Server, Exchange Server, or other).
  • Microsoft made a big change to focus on software as a service (SaaS) and began to transition products in that direction starting with mature products like Exchange Server (their e-mail server offering).
  • Brett’s job as technical readiness manager for these services coming out was to produce content that told the world how these things worked – what the products looked like, how to use and configure them, and overall what they did from a technical perspective.
    • Things like how to migrate an e-mail box to the cloud would fall into this category.
  • All of the partners were used to selling on-premises software and servers and had to transition to selling much cheaper components (i.e. mailboxes). The partners were not happy.
  • Brett remembers being at a user group in the Seattle area and being surrounded by a bunch of Microsoft partner representatives and being peppered with questions. These people wanted to know why Microsoft was forcing them into a services model, and they were afraid they would make less money as a result.
  • At the time the industry was changing and shifting toward software services. If these companies did not make the shift then, their competitors would beat them to it.
    • "You’re either going to do it with Microsoft, or Google is going to take them from you." – Brett Hill speaking to partners about this industry shift
    • Brett’s job was to show partners how they could make the technical transition from on-premises systems and services to cloud based systems and services.
  • Partners finally came around to understanding what the future was going to be and realizing the need to adapt.
• This was a challenge for Brett personally to shift his focus from IIS and a server service (i.e. install / setup a server on your own premises to run IIS), and now he was talking about services in the cloud hosted by Microsoft. It’s a mind shift change.
  • People don’t always want to give up the control. Brett wonders now why people would ever want the control in the first place.
  • Would you rather have a copy of your mailbox on-premises on a server that the janitor could potentially knock over and damage or in a Microsoft datacenter with multiple live copies and geographically dispersed facilities for extremely high availability and failover?
  • If you are a technologist who can help do a migration to a service like Microsoft 365 (or some other cloud service), it’s a career accelerator.
  • Brett says we’re almost at the end of the adoption curve for this specific type of migration. During his time in the partner technical readiness manager role, he was working with early adopters.
  • You need some large enterprises to sign up to be early adopters because they see value in the future. Early adopters help mature the services. There is a price to pay for being an early adopter because the technology may not have been exposed to that type of scale.
  • It’s one thing to take an application and have 20 people to see how it behaves, but how do you know how it will behave if you put 2 million people on it?
  • Brett mentioned a form of beta testing Microsoft used to test things at scale (i.e. deploy to 2 million randomly selected users in a specific area to see what happens) before rolling out to all users in stages.
    • These were the beginnings of controlled deployments for large scale services (i.e. cannot roll new changes out to every service user but must do contained test at scale to prove functionality). These later became rings of deployment that end users of Microsoft 365 could leverage to roll out changes to their enterprise.
    • Now companies can control the changes pushed to their enterprise from a Microsoft 365 standpoint (moreso than was granted in the early days when Microsoft decided it for you).
    • If Brett were planning to hang his hat on something these days, he might look into this area due to the broad scalability.
• The scaling of the technology isn’t so different from Brett needing to scale his classes for 20 people to a series of classes across the globe.
• This conversation started when we began discussing wrapping your head around the scale of things.
  • Nick references people who have moved to larger organizations and their needing to understand how technologies work at a large scale. Brett reiterates the challenges of wrapping your head around the scale of what Microsoft is doing.
  • It’s something you have to learn how to do (understand and think at scale), and problems at scale are a different type of problem. For example, a problem at scale that looks like a network failure may be an authentication failure (or some process that took too long with API calls in the dependency chain). Diagnosing these types of problems at large scale is very difficult.

47:29 – Microsoft to Riverbed

• Brett left Microsoft and worked for Riverbed in technical marketing for about 5 years. He was a principal technical marketing engineer. Riverbed got their start in bandwidth optimization.

  • In a way he was a network optimization specialist and also an evangelist for optimization services related to Office 365.
  • Brett had his own dedicated private demo environment / test lab, which he loved. It made him feel like the next iteration of the kid who rewired the living room lights so many years before.

• How technical does not someone need to be to go into tech marketing?

  • Brett believes in levels of competence.
  • Brett became a principal technical marketing engineer likely because of his background with the Microsoft technologies. Others on the team were younger, were just getting started, and did not have that kind of range (or depth).
  • Everyone on the team had technical chops in some dimension. If you are going to be in technical marketing, your job is to make the technical content relevant with the audience. The human to technology value has to resonate.
  • "It’s not about the features. It’s about the impact. And if you can do that, you are going to be successful." – Brett Hill
  • It’s a matter of how deep you go. The more competent you are technically, the more useful you are in a lot of different scenarios.
  • Brett became helpful not only to customers but also to engineering, providing feedback and ideas for how to improve the products and services.
  • Marketing, customers, and engineering are kind of the big 3 you have to deal with in technical marketing. You’re an engineer and dealing with the pre-delivery software usually.
  • Brett setup demo labs for anyone in the company to leverage for Office 365 acceleration (which drew on his lab / demo experience from previous roles). They didn’t have to call him to do a demo and could do it on their own if they wanted. It was creating demos at scale.
  • Presentations were also a large part of the role.
  • This goes back to proof of work. If you’re building a lab environment, it is not just the building. You have to write the manual for others to use (in this case a manual for salespeople to use).
    • Brett suggests taking screenshots of what you want people to do so it’s easier to understand. People understand things better when you show them. The downside is you have to update it as software changes come.
    • Training that is only text is efficient but is not Brett’s style.

• From the outro…

  • If you were someone whose business was impacted by the move of Exchange Server to Microsoft 365 hosted e-mail (and more), we would love to talk to you about that disruption and how your business had to change.

Contact us if you need help on the journey.