How do we determine if a manager is the right fit based on our personality, values, and the way our brain works? Kellyn Gorman diligently investigates a potential manager before taking a job. As someone with autism and ADHD, having a supportive boss is critical to her success.

This week in episode 321 we’ll explore how Kellyn got into both the Oracle and Microsoft communities and the reasons she is adamant about developing public proof of work (like blogs and public-facing presentations) that showcases mistakes on the path to learning.

Listen closely to follow Kellyn’s transition from Oracle community group participant to leader, from public speaking novice to keynote presenter, and the differences she observed when participating in the Microsoft community.

Original Recording Date: 02-21-2025

Kellyn Gorman is a database professional who has worked in the technology space for 25 years better known as DBAKevlar. If you missed part 1 of our discussion with Kellyn, check out Episode 320.

Topics – Interviewing and Qualifying Managers, The Importance of Proof of Work, A Tale of Two Technical Communities

3:00 – Interviewing and Qualifying Managers

• Kellyn had mentioned not wanting to spend time on things which are not valuable, but she has developed a way to determine if sources of information are valuable over the course of her experience. In some cases, she is creating valuable resources that do not yet exist for the benefit of others. Kellyn has also learned how to determine if a manager will be valuable to her and fit in with the way she likes to work. How can listeners ask the right questions to determine if a manager is the right fit for the way they like to work?
  • Kellyn says often times when we interview, getting the job is the main focus, which is understandable. If it is not the right job, it can put you in a very bad situation.
  • With Kellyn being AuDHD, having a good boss is essential for her to be successful.
  • Many times, when Kellyn is being interviewed, the people who are interviewing her have read her blogs, the books she has written, or have seen her speak.
    • “They know me. It’s very normal for them to go, ‘I don’t have to give you a technical interview. I already know what you know.’ Ok, well then I get to ask questions.” – Kellyn Gorman
  • In a job interview situation, Kellyn likes to ask questions about how a manager assigns work and the regularity of updates they need (i.e. regular check-ins vs. clear communication of the deadline and nothing more). She does not work well with micromanagers and needs autonomy and trust from her manager.
    • “Go ahead and run the race. I don’t need to know how. That’s important to me. I am a professional. I am going to do the best job and really take care of that company and be extremely loyal. I need them to trust me to do that.” – Kellyn Gorman
  • When Kellyn worked for Microsoft, a mentor encouraged her to take the Clifton Assessment, and it has been extremely valuable.
    • Kellyn says one’s assessment can change over time and will re-take it now and then. The assessment tells someone what you will be like as an employee (skillset, potential, weaknesses).
    • Kellyn likes to give the assessment results to her boss as “an employee manual.” Not all of them, however, take the time to read it.
    • “The ones that read through that…I know I’ve got a good chance of having a good boss. If they just throw it aside…they don’t even take the time to read it…may have problems. They’re not even curious enough about me to read that assessment. And it’s not a long one. The top-level assessment is like 5 pages.” – Kellyn Gorman
    • Kellyn’s Clifton Assessment says she is a strategic thinker, a go getter, and that she does not need a lot of management. People can tell her what they need, and she can figure it out from there.
    • Kellyn is looking for a manager who is flexible and trusts her to go and do her job. They need to understand the deep expertise she brings to the table (Oracle expertise, for example). Kellyn wants to make sure a manager understands the challenges of being in an older technology space but operating across a broad set of communities.
    • “I have what’s called…a Lego brain. If you want to know how your technology fits into every other technology, I can tell you. You want to build out a solution and market it to any different provider no matter if it’s Google or Microsoft? I can architect it for you…. That’s all I do for one company right now. I build them solutions. I architect them, and they take them and market them. And it’s awesome, but I needed a boss that understood that…. I need Kellyn’s Lego brain for this.” – Kellyn Gorman
    • A good manager for Kellyn won’t try to control or stifle her talents but will enable her to leverage them to build the solutions she delivers to the company.
• How does Kellyn prioritize what to address about the way she likes to work during the interview process and what is ok to save for after she gets hired?
  • Kellyn addresses a lot during the interview process, and she interviews for long periods of time.
  • Kellyn spoke to her current manager for a period of 4 months before she was hired. It was a similar time period when she went to work for both Microsoft and Silk.
  • Speaking with other individuals inside a company who can answer specific questions is very important to Kellyn as part of the overall process of seeking a new job. Our contacts are extremely important.
    • Kellyn tells the story of taking a role at Oracle and making good decisions with the help received from Mary Melgaard in navigating the job offer process.
    • When Kellyn went to Microsoft, she contacted Bruno Borges for help.
    • When seeking a job with Silk, it was Tom O’Neal and Chris Buckle who helped Kellyn navigate the process.
    • Upon coming to Redgate, Kellyn had help from Louise Domeisen.
  • “I want to feel secure. I need that secure feeling that I’m making strong choices and understanding.” – Kellyn Gorman
  • Kellyn has also negotiated other opportunities outside her job responsibilities with potential managers. That negotiation process / those types of conversations can give you insight into what someone will be like as a manager.

11:18 – The Importance of Proof of Work

• John highlights Kellyn’s emphasis on having proof of work that people can learn from and even discover her by as well as a strong professional network.
  • Kellyn advises every mentee she has to blog and do public speaking.
  • “I am out there. People already know what I know, and it’s a way for people to comprehend and to get a jump in. I have not had to go look for a job in over a decade. We’re talking a good 15 years. People have come to find me and said, ‘we want you….’ It’s really important to be out there. Be present. Just be the best that you can be and show what you can do…. People will come find you, and they will offer you jobs.” – Kellyn Gorman
    • Kellyn’s job at Redgate as an Oracle Advocate began with an ask that she work for them as an engineer 10 hours per week. The Redgate advocacy team would later decide they wanted Kellyn to join them but initially did not realize she was already working for Redgate part time. They offered her the Oracle Advocate role without needing to interview for it.
    • When Kellyn went to join Silk, she had reached out to Silk and 2 other companies stating her readiness to leave Microsoft and requested they create a role for her. Silk provided exactly what she asked for (a role that would put her skills to work).
    • Kellyn also tells the story of someone asking her to take their role at Delphix.
• John references themes of learning in public and documenting your thought process (as a beginner or otherwise). We have discussed these with previous guests, aligning with advice from the book Show Your Work by Austin Kleon.
  • Documenting our successes and failures makes our writing more approachable to those who are beginners or less knowledgeable in an area.
  • John asks Kellyn to contrast how this strategy can help those who are entry level or early career in a specific area compared to those who may be more experienced or subject matter experts.
    • Kellyn has been blogging on DBAKevlar since 2008 and regularly models documenting her mistakes for people to see. Kellyn calls out one mistake she documented related to an Oracle upgrade.
    • Publishing our mistakes showcases our humanity to others. We make mistakes just like everyone one else. Kellyn uses the example of her son thinking she was perfect and helping him understand she makes plenty of mistakes.
    • Kellyn used to see posts from people in the industry detailing the incredible things they were doing. As a result, she thought those people never made mistakes. Kellyn stresses the importance of showing when we mess up and how we cover from it.
    • Kellyn’s husband was her first mentor and worked with her when she was a junior DBA (database administrator). Kellyn’s husband shared a story with her about a mistake he made related to removing a large database index. Her husband’s boss didn’t get upset but rather was focused on moving forward after the mistake.
    • “And that was it…. It happened. Let’s take care of it. And when you hear that from somebody as prolific as my husband was in my view at that time, you start to understand it’s important to share those mistakes. It’s important to talk about your journey.” – Kellyn Gorman
    • If you read Kellyn’s blog, she started off as a DBA learning things the hard way. While Kellyn was documenting things for herself, she also thought others might find her writings interesting if they were published in a blog. From there, Kellyn continued to grow and do more.
    • “This is my path in tech. This is what I’m doing. If you find it interesting, go ahead and read it. If you don’t, I’m alright with that too. It’s alright. I may need this next week when I forget what I did in 10g, so we’re good.” – Kellyn Gorman, on blogging
  • John says Kellyn is demonstrating that she does good work while documenting the outcome as well as the process. Part of Kellyn’s personality is a desire to make others better and to help the community.
    • Kellyn says this is part of the reason she adores the Microsoft community.
    • “I ended up blogging a lot more on the tech community for Microsoft than I did on DBA Kevlar for…recent years.” – Kellyn Gorman, on how her blogging changed after she went to Microsoft
    • Kellyn had been blogging weekly on her own site for years but wasn’t able to keep up the same pace after joining Microsoft. After Kellyn left Microsoft, she added the content to DBA Kevlar so it would be retained.
    • Kellyn emphasizes the importance of keeping track of the public-facing content we’ve created over time so people know it exists.
• In mentoring conversations with others about blogging or speaking, what does Kellyn think is the biggest hurdle people have to overcome to actually start?
  • “They think they don’t have anything important to say, and I will remind them that some of my most popular blogs are things that I thought was stupid. Nobody’s going to read this. Nobody’s going to think it’s good. And those are the most popular blogs. I…documented using a Windows Oracle Enterprise Manager and monitoring HP UX targets. I thought, ‘nobody is going to read this. This is only there for me because I’m going to have to support this customer long term….’ That thing gets hit constantly, every single day…. It’s not the things you think will be popular. It’s not the things that everybody else is doing. It’s the stuff that nobody else knows. So just start writing and see what happens. Don’t overthink it.” – Kellyn Gorman, on blogging
  • Kellyn documented building a VM image of a Raspberry Pi to use for STEM classes. People loved it and were downloading it for STEM education.
  • John says we don’t know the purpose for which others will use our problem solving. If we document something for public consumption, people will use it in ways we just can’t know.
  • Kellyn says as people in your community retire, they may take down their blogs. It’s a consideration point.
    • She has some of the only deep command line interface content for Oracle Enterprise Manager, for example, and is committed to preserving it for others.
    • “I can’t ever take that down because if I do, it’s gone. It’s gone forever.” – Kellyn Gorman, on technical knowledge that can be lost when subject matter experts / community contributors

21:11 – A Tale of Two Technical Communities

• Kellyn does public speaking, has written blogs and books, and has been part of technical communities. What was the order in which Kellyn started doing these things? What came first?
  • Kellyn had attended RMOUG (Rocky Mountain Oracle Users Group). It was the largest regional user group in the country and was closed to where Kellyn lived.
  • “I wanted to start speaking, and the reason that I wanted to start public speaking was I found that my ADHD made it very difficult for me when I was in a public space. People would ask me questions, and I absolutely had the answers. But I would lose access to my brain, and I wouldn’t be able to come up with it at that moment…. Even if I knew the information, it wasn’t accessible for me…. I remember my first talk when I went to RMOUG. I went and did the talk, and I was going to do it on temporary table spaces with parallel processing…. The door closed, and my talk went out the door with it…just was gone…. It was horrible. It was the worst talk ever, but it got better. Again…didn’t give up…be persistent…continue to talk. And now I can talk on anything. I’ve got it down.” – Kellyn Gorman
    • Kellyn would encourage people with questions to talk to her 1-1 at a later time to hide the fact that it was very difficult to come up with answers in the moment.
    • In that first presentation for RMOUG, Kellyn spoke for about 35 minutes trying to go through her slides, but it was a struggle.
  • Kellyn is doing a number of keynote presentations as the Oracle Analytics and Data Summit 2025, Kscope, Scenic City Summit, and SQL Saturday Oregon.
    • Kellyn loves doing keynote presentations on topics that interest her, but it took her beginning the public speaking journey in 2011 to get where she is now in 2025 (14 years).
  • Kellyn went from attending the Rocky Mountain Oracle User Group (RMOUG) to speaking at events. At one point she approached the board members of RMOUG and expressed her interest in volunteering to give back to the community.
    • Other board members of RMOUG immediately suggested Kellyn run for a term as board member, and she did.
  • Once Kellyn was a member of the RMOUG board, she started running the RMOUG Training Days conference. At the time, there were around 1000 attendees.
    • Kellyn recently attended RMOUG Training Days and reports there were only 80 attendees.
    • “It’s heartbreaking to see where the Oracle community is now. Because of so much content that is out there, it’s hard to get people to go in person to events like this. There’s cloud events. There’s everything. It’s very challenging.” – Kellyn Gorman
  • In 2011 Kellyn was made an Oracle ACE. This is a community recognized award. One year later, Kellyn was named an Oracle ACE Director (the highest award from Oracle).
  • In 2014 Kellyn won Women of Tech of the Year for the state of Colorado.
  • Also in 2014, Kellyn and her future husband Tim Gorman were doing keynotes across the world. Being a part of the same community ended up eventually bringing the two of them together.
  • Kellyn stayed in the Oracle community through 2018 / 2019.
  • In 2012, Kellyn attended her first SQL Saturday, which is focused on Microsoft technologies.
    • Kellyn immediately wanted to know how this community was able to get so many women attendees (40% were women at SQL Saturday compared to 7% at Oracle community events).
    • A couple of the speakers at the SQL Saturday event explained the DEI (Diversity, Equity, and Inclusion) and Women in Tech initiatives that Microsoft had.
    • “It made total sense to me. It was what I was trying to bring over to the Oracle side. They just weren’t ready. They just weren’t ready on the Oracle side. And I was just utterly amazed. So, I started going to SQL Saturdays.” – Kellyn Gorman, on discovering the Microsoft community
    • Kellyn worked with SQL Server technologies and had built some expertise in that area.
  • In 2016, Kellyn attended her first PASS Data Community Summit.
    • “I just loved the energy. I loved the inclusivity…everything that they were doing. I just was so impressed…. This is the way user communities are supposed to be. It’s all about you do you and I’m alright with what you do. It was just incredible. That was pretty much my love affair starting with the Microsoft community….” – Kellyn Gorman, on her love for the Microsoft community

Mentioned in the Outro

• Special thanks to former guest David Klee for recommending we have Kellyn on the show!
• Nick had not heard of the Clifton Assessment before speaking to Kellyn. It’s a great idea to do something like this to help identify strengths that perhaps others do not point out to you. Knowing our strengths can be leveraged when we interview for jobs (part of the career narrative we need to tell in interviews).
• Kellyn asked people inside the companies she was targeting for her next role for help during the job seeking and interview process. She found a harbor pilot just like we discussed in Episode 317 – Own Your Job Search: Be the Captain, Find a Harbor Pilot.
• Kellyn’s attitude toward blogging is much like that of Duncan Epping as discussed in Episode 304 – Next Level: Shifting Specialties and Broadening Your Outcome Goal with Duncan Epping (2/2). The purpose is documenting a learning journey that showcases mistakes.
• It’s ok to be part of multiple technical communities. It doesn’t have to be just one! Kellyn has been part of the Oracle and the Microsoft communities.

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