Name: Gary O’Neall

Gary O’Neall started out as a software developer at Hewlett Packard, working his way into management. He then moved from large companies to smaller startups where he took on increasing responsibilities while continuing to stay close to the technology.

Throughout much of Gary’s career, he has participated in the open source community, technical due diligence, software, and internet security.

Roughly ten years ago Gary developed the software and founded a source audit company, where he helps companies to understand their use of third-party libraries and open-source software. Gary made this choice in order to find work-life balance.


Before jumping into the interview, just a bit of how this interview went.

This is now my second interview. The first was with Greg Siu. I tried to do better this time in a couple of ways. I asked the questions (last time Greg had the questions and read them. I also worked to keep the responses tighter. And I split the interview into two parts. The first part covered the standard set of questions that I intend on asking during each interview. The second was a summary of the career path or journey that Gary took.

I added the second part based on requests that I have received from a couple of millennials. They are very interested in the career paths that successful managers and leaders have taken.

I have not decided how to best share this career path interview with you. I am considering adding a podcast section to the site. Let me know what you think!

Now on to the interview with Gary!

What tools and tricks do you use to find work-life balance?

Gary is in an interesting position today – he runs his own company. The way he has structured his work is by the project. When he works, he works really hard. He then takes time off before the next project – giving himself a great work-life balance.

This is not how he started nor what he has done for most of his career. He has worked in big and small companies where he has worked long hours and taken regular vacations.

As a result, his answer to the above question varies based on whether he is talking about his current position or his previous jobs.

“I make sure I absolutely have time for exercise because that helps me be more productive at work.”

In Gary’s current job.

“I’d work, work my butt off for two weekswhere I might be working 70 hours a week…”

“Then I take two weeks off and I’m able to make enough money, you know, to be able to sustain that lifestyle. So that works out great for me because, in that two weeks that I have off, I can travel, I can focus on things, I can do projects, you know…”

Looking back at his previous jobs, including startups.

“If I go back to the days when I was, you know, working the 60, 70 hours a week, especially working at the startups, it’s always really hard because they’re kind of all-consuming.  It’s actually a lot of fun for me too, so it’s easy to kind of lose track of your personal life.”

One thing that he mentioned that I thought was worth capturing.

“I actually had a boss once that supported a life balance that worked out really well for me. Worked out well for him I think just for everybody…”

“We had a policy – when you take a vacation, you really do take a vacation and man, that just cleanses the soul, you know, you come out refreshed, you’re more productive when you’re back. I think that’s just a great policy to have.”

How do you prioritize your work?

Gary had some amazing and fairly aggressive approaches to how he prioritizes work!

“I do follow the Stephen Covey rule, you know, which is the urgent versus the important, you know, so don’t get distracted by things that are urgent that really aren’t that important.”

“One of the questions I always ask myself, and I heard this from somebody else, so I can’t remember who to give credit for it, but if you go out three years or five years and you look back, would that make any difference at all?  And if it doesn’t make any difference, maybe it really isn’t important, you know.  It might be urgent, but it’s not important.”

“Most of the time I just don’t do the urgent. For a lot of these after a day or two, it doesn’t matter. It just blows over… It’s like, oh, I didn’t get it done, you know, and turns out it didn’t really matter.”

Tell me about an example where you had to let someone go for underperforming.

I don’t have much to add to what Gary says below other than to say – sometimes when you let someone go, it actually works out for everyone…

“I’ve been in situations, especially when you’re in a startup, you end up having to let people go for economic reasons, as well as performance reasons. One thing I’ll just mention isthatthere a big difference between big companies and small companies. You do have a lot more luxury of time in a big company. You can’t take a lot of time to get people to improve performance in startup companies.”

“One of the interesting things I learned is from the small company experience is moving more quickly.  This actually tends to be more advantageous to the person that you’re taking action on.”

“I’ll tell you one story. This was somebody I let go. This is one of the first experience I had where I had to like let somebody go because of economic conditions. So this is a person that was doing a decent job. I really wanted to keep this person on the team, but we had to let somebody go and we went through a process of assessing, you know, based on seniority and all these other very measurable criteria. And of course, we’ve got to make sure it stands up to the legaltests.”

“This stressed me so much because it’s like – this person’s going to be out of a job. I’m ruining this person’s life. It was a lot of angst for me. I went through the whole process and I actually ran into that same person. I was walking through the streets in Taiwan and in the capital, Taipei. I ran into this person that I had let go. She came up and gave me a big hug and said that was the best thing that ever happened to me. Because after I let her go, she was able to reconnect with my family and actually found a job where we could move back to Taiwan.”

If you had to give advice to someone setting up a team in another country, what would it be?

As a bit of background on this one. Gary has set up multiple teams in other countries. He continues today to work with an engineering team in India. He could write a book on the topic. One key learning for me is his description of how to build trust.

“This is something I’ve done a lot. It actually depends on what level of management you are at.  If you have senior enough managers and they are really good enough to set it up…”

“One of the key things is to be on-site, especially for the leadership team…  establish the rapport because that’ll go a long way to maintaining the communication and a level of trust.”

“There are learned techniques for when you sit down with somebody – how to establish an emotional connection. I’ll just give you one example. There’s something called pacing. Everybody operates on different clock cycles. Some people are really fast. So they talk quickly and they bounce around a lot, they move their hands a lot. Other people may be slow, and methodological. One way to establish rapport is you see what clock they’re running at and you synchronize with it.”

What was the most difficult transition that you made in your career?

I love this. Many of my friends started out as developers and moved into management. Nearly all of them would say the same thing that Gary said below. But they all made it through, learned a lot along the way, and are now great managers and leaders.

“Oh, clearly going from being an engineer to a manager.”

You have to get used to not seeing the results of your action immediately and not knowing whether your decisions are correct, it might be a year before you know whether that hire was the right hire. That promotion was the one.”

“The promotion was in the same group. And, quite honestly, being a manager of managers, I try not to do that because it’s actually hard, really hard. It’s really hard because you have your peers that you’re suddenly managing it and reestablishing that relationship.”

Do you have any book recommendations that you would like to share?

“I read a lot of Harvard business reviews and it’s kind of like the reader’s digest of the big books. I liked it because I’d get little articles. It appealed to me because it’s very scientific. A lot of it is research-based. There’s data behind it. I understood that a lot of it was psychological-based management styles.”

What is the one or two things that you want to tell me that I didn’t ask?

Both Gary and Greg (my previous interviewee) have worked in big and small companies. I think at some point I will write a post about the similarities and differences – based on what I learn from the interviews.

“I learned a lot going from a large company to a startup. I spent probably 12 years, I think I was 12 or 15 years at Hewlett Packard, a big company.”

“I loved that company. They trained me well, they invested in me, and it was a wonderful experience. And then I went to a startup,  and all of a sudden you’re going to go play in a different environment, a different world. There were some bad habits I learned from the big company that I had to unlearn.  One of them is being quick about your management decisions, not taking time, if you know what’s right, make those moves quickly.”