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Emily Freeman, I want to welcome you to the show. I am excited to have you here.

Thanks for having me.

Tell me a little bit about the work that you do in the world.

I am a developer advocate at Microsoft. Developer advocacy is a broad term that describes a bunch of people with unique skillsets. These are people who typically have an Engineering background. They were slinging code or propping up infrastructure. They discovered or had an interest in speaking, writing tutorials and creating SDK or Starter Developer Kits. They are supporting developers and operations engineers in their communities.

What do you think the biggest challenges are for your team now?

We are in the time of COVID-19. Although, my team is distributed across the world and we’ve worked remotely for years, working under this societal pressure and this strange zeitgeist has us all reeling a bit to be honest. Readjusting not only our work patterns, but also trying to figure out, “What is this new normal?” We don’t know how long it’s going to last. For my team, we speak a lot at a lot of conferences, whereas I can make the argument that developer relations and developer advocacy over-indexed on conferences, speaking and travel. To have it completely ripped away is jarring.

To be honest, as a person, I miss engaging with my community in person and meeting developers where they’re at. Not just from a technical standpoint and a community standpoint, but also a physical standpoint. Being able to get on a plane, interact with them, grab dinner and drink, whatever, it creates a deeper connection that aids in my job and doing my job well. We’re trying to figure out, “How do we still connect with developers and engineers online?” Twitch and streaming has helped with that, but it’s an adjustment.

As a leader, how are you orienting the way that you lead during this time?

I’m trying to strike the balance and I’m sure I’m tearing, slipping on the edge every day, but I’m trying to strike this tension. For some people, work is a distraction and a wonderful area to focus on and block out the varying chaos in their personal lives and their homes. A lot of us are working with kids at home for the first time, which is interesting. Being sensitive and understanding this is hard. People are going to process this differently. Tailoring my leadership and my management style to these individuals and meeting them where they’re at emotionally. That varies day by day.

DevOps is truly centered on rapid iteration. Click To Tweet

What experiments are you doing at this time?

Not related so much to COVID, I started this experiment prior but I realized after attending a management training with Laura Hogan, she had this exercise where you looked at directive leadership versus empowering leadership. If you think of them as a linear scale, where the directive is on one hand and empowerment is on the other, I realized I have a massive bias toward empowerment. I don’t like it when people tell me what to do, I lean heavily on this empowerment side. The best way that I work as an individual contributor I see is that when someone says, “This is your North Star. This is the mountain we’re going to conquer,” and they let me figure out how to do it. That’s when I do my best work, but not everyone’s like that. Some people need and prefer more direction. They want a little bit more of the how, why and what. I’m working on moving my leadership, not toward this empowerment bias, but creating this flexibility and ability for me to provide direction to my employees when they need it. To do it in a way that is clear and concise and communicates what I need to efficiently.

How do you know if it’s working or not? How do you collect data? How do you think about it? If it’s an experiment, how do you evaluate the efficacy of it?

Anytime you’re running an experiment, establishing a baseline is important. I wrote DevOps For Dummies. One of the things I talked about in the book is if you’re starting this DevOps transformation or even implementing iterative processes after, maybe you’ve been “doing the DevOps” for months or years, but not seeing a lot of impact from it. How do you pivot and add things? The thing I say is you have to start collecting data.

A lot of times you don’t know what data is going to be most useful in these situations. I always cast a wide net and look at performance in general. As time goes on, you’re able to refine it, “This was just noise. This is the actual signal. This is what we’re going to track long-term.” I use OKRs. I am establishing those with some flexibility. OKRs should not be this waterfall style decree where, “These are our objectives for the year and we’re never going to touch them again.” I don’t think that works. Humans and tech move quickly. Establishing OKRs and tracking, “This is the performance here. For my team, what kind of content do we need to create? Are we creating it? Are we seeing that impact with engineers? Are they viewing the content, interacting more?” That’s where I’m at. Tracking it and trying to nudge that in the direction I want to go.

What else can we learn from DevOps about experimenting in a time like this?

My favorite thing about DevOps is that it is truly centered on rapid iteration. If you think of the software development lifecycle, that’s everything from the idea on one side to planning, coding, testing, deploying, maintaining and often in the end, to deprecating. If you look at that full linear process and you take both ends of that line and you bend it into a circle, that’s where DevOps gets dynamic and interesting.

You have this wonderful cycle that you can design around your customers. You’re constantly centering your end user. You’re able to iterate quickly. You have an idea for a great feature that you think your customers would love, but you don’t know. You would create an MVP, a Minimal Viable Product. You’re able to release that at a basic level and collect that feedback. You can talk to your customer, “Did this solve your problem? What would you like added? Was it worthless?” If you turn on a feature and zero people sign up for it, or worse you get a bunch of complaints about it, you need to react to that quickly. DevOps enables teams to move faster while still creating reliable software.

If I’m a small business owner out in the world during COVID-19 experimenting, how might I apply that? What do I grab from what you said? How do I make it real for me?
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First, if you are a small business owner going through this, I respect you because this is an incredibly trying time. Trying to do right by your employees and your customers is difficult. From DevOps, they can glean this idea of iterating quickly. With COVID-19, we don’t know how long this is going to last, what’s going to happen. There are a lot of cascading impacts. Not only are we in a health crisis, but we’re in an economic crisis because we can’t interact as a society as we normally have. Being ready to pivot and not getting too engrossed or too emotionally attached to any long-term plan.

For example, I’ve been doing our next fiscal year. I am looking at our plans, budget and what activities we’re doing. I have a lot of contingencies. I may not have it formalized but I have an idea of, “This is what we’re going to do if events come back online.” If they move from online to in-person again, I should say. If you have events come alive again in June versus September, how do we handle the events that we host as a company? Thinking through all the possibilities and having a loose idea of how you would react and pivot your business while also supporting your employees and your customers. You have to center your customers. We have to support each other as colleagues as well.

I have a general question. I hear all the time that people think, “What if people don’t go back to work? What if everybody stays virtual?” You have a company that has Microsoft teams. What do you think about that?

I have mixed feelings about this because, first of all, if I never get to interact with you once again, I’m going to lose it. I do think that this was a way of showing certain businesses that remote was possible. I want to emphasize though that this is not a normal remote situation. If you’re an employer and your employees are working via teams or other coordination software, chat programs, and you’re evaluating their actual productivity in this time and then applying that to remote work, it’s going to be skewed.

I am not as productive as I usually am at this time because, one, I have a child at home. Two, we’re distracted. There’s a lot going on. I want to be hesitant to say, “Please don’t evaluate remote work based on this alone.” I am curious about what companies are going to do after this. Are they going to say, “We’re spending X amount of dollars on office space every month. Maybe we don’t need that at all. Maybe we need it for certain people or we can scale back.”

There are going to be some interesting impacts of this. Some people work better in offices. I want to be careful to respect that working style, but also when you’re joining an industry like junior engineers or people that are brand new to development. Having that in-person connection and being able to tap your colleague on the shoulder and ask him a question in an office, that’s a different level of engagement and connection than you can establish online. This will impact remote work and it will probably increase it, but I don’t think it’s going to be something where we skew offices forever.

I want to ask you, as a leader during hard times, how do you know when you need to and how do you take care of yourself? What do you do for your own self-care?

I’m not nailing this. I don’t know if I need an expert to talk to you about this. I like the phrase “holding it with an open hand.” You can make plans, grip it tight and hold on to it. If you make this loose idea of a plan and you hold it with an open hand, that’s what I’m trying to do. Some days I recognize that I’m not in a healthy headspace. I have people that I rely on, friends, resources and therapists who help center me and allow me to vent and process through things. Sometimes it catches me off guard.

I was fine and then my house got quiet. My daughter went to her dad’s and suddenly, I was confronted with the reality. There were no distractions. It was just, “You are alone and you can’t see your friends. You can’t go anywhere.” I couldn’t even order pizza. It’s a hard situation. Being able to provide grace, not only to other people but to yourself and being understanding of, “I may not be my best self. and that’s okay. I’m going to forgive myself for processing through this.” That’s my attempt. I don’t know about you, Melanie, but this is my first pandemic. I’m figuring it out as we go.

That’s such a good reflection. This is our first pandemic. There are no best practices. We all have to get through it however we can. I have appreciated having you here. Where can people find DevOps For Dummies?

DevOps For Dummies is available on Amazon if you search for it. It’s also on O’Reilly and some other groups. It’s widely available. I would love to hear what you think about it. If you want to reach me, the best way is on Twitter, @EditingEmily. My website is EmilyFreeman.io.

DevOps enables teams to move faster while still creating reliable software. Click To Tweet

I’ve always wanted to ask you this. Why are you @EditingEmily? 

A long time ago in another life, I was an editor and writer. I ghostwrote for Entrepreneur, Forbes and these other outlets. At that time, my business was called Editing Emily. I have a strong affinity for alliteration. It shows up every time I need to brand something. That was my business name and it ended up being my Twitter. @EmilyFreeman is an egg photo who hasn’t logged on to Twitter since 2019. I can’t get it, so here I am, @EditingEmily.

Thank you so much for giving us a minute to hear your thoughts about leadership. I appreciate it.
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Thank you for supporting business owners, entrepreneurs and professionals through this process. This is helpful.

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I got done talking with Emily Freeman. I love how she talks about how DevOps can help inform experimentation. It’s interesting how she talks about how client feedback can help you improve your product. You start with a prototype then you get feedback from your customers before you make big investments to see if the features of any product that you’re developing will be what your customer is looking for. How do you find out quickly what your customers are looking for, that will make you a better experimental leader? I love the idea of looking at feedback loops both with your clients and with your staff to get the most information on the table to help you figure out what you need to develop next. This is Melanie Parish, go experiment.