Host Intro (Gene Kim)

Okay, up next is Courtney Kissler, who has been part of the DevOps Enterprise Summit program committee from almost the very beginning. She has been absolutely tireless in her quest to help this community better understand how to successfully bridge the business and technology divide.

She brings to the committee a ton of things, including a relentless focus on that issue, as well as an amazing network that she routinely brings to bear to help this community better get from here to there.

She is currently CTO at Zulily, responsible for all engineering and technical aspects of that organization, as well as product management. She has presented many times at this conference in her previous roles at Nordstrom, Starbucks, and Nike. Earlier this year she presented a lecture on career advice that I thought was so valuable and unique that I thought she needed to share this with a broader audience. So here is Courtney.

Courtney Kissler

Hi, everyone. I just have to say how exciting it is to see everybody in person. I have really, really missed this.

As Gene mentioned, I am going to share just a little bit about my own personal experience with navigating career decisions. It is really my journey around how I think about new roles, whether it is internal movement in an organization I am already a part of or making a decision to go to another organization, and how I have thought through that.

Let me start. Here is what happened to me. I had been in an organization for 14 years, learned a lot, held a lot of really great roles. I started as an engineer and navigated into senior leadership roles. But I made a decision that I was going to make a change, and I was in a bit of a rough spot. I had not updated my resume in 14 years. My LinkedIn was out of date. I had not interviewed in 14 years. It just was not natural for me. I had a really small network, and this whole concept of having a personal board of directors was not anything that I had considered ever in my career.

So here is what I learned. It is important to own your destiny, really be in control of where you are going, and not be scared. I think there is some amount of healthy paranoia and uncomfortable feeling when you are going to make a change, but embrace that versus be afraid of it.

Always keep learning, never stop learning. Also, after the talks today, I think it is important to continue to unlearn, because there are so many things that become part of your toolkit that need to evolve over time depending on how things have changed.

As I said earlier, I did not have a very big network, but I got introduced to this community back in 2013 or 2014. Huge thanks, and I will give future thanks to many of you, because I am a big believer that this is a place where people get connected and create relationships that last a long time.

After I made my move, I put together this criteria, and I use it for every role that I am considering, again if it is internal or external. Number one, and this will not be surprising, but sometimes I have rationalized this and I have regretted it: who I work for. Super important. I value different perspectives, but what I have struggled with in my past is if I ever have a values mismatch. So I am always striving to understand: am I working for a leader where, at least at a minimum, we have the same values? How we go about things can be very different, but I want us to have aligned values, and can I learn from the person?

Who am I surrounded by day to day? Who am I leaning on for success? If I am leading a team, who are my direct reports? And then, what is the state of the team? Am I building a team from scratch? These words are directly out of the First 90 Days framework, so if you are familiar with that, same words: are you sustaining success? Is it an underperforming team that requires a turnaround? Is it high performing?

Am I passionate about the mission of the organization or the subject matter area that I am a part of? Can I get excited about what I am doing every day? And then, is it moving me towards my career goal? I have taken steps sideways, backwards, as long as I am learning something new and I feel like this is an experience that is going to get me ready for the next role.

They are stack ranked in this order of consideration.

Okay, pressure testing. How do you go through this, and how do you know? Hopefully people recognize this reference, and many of you know how much I love karaoke, so: How Will I Know?

Really, what you are doing through this process is you are trying to take the blurry and make it clear to the best of your ability. Do whatever you can to take anything that is unclear and drive that clarity.

I do this through questions. These are some examples of questions that I have asked as I am assessing, and you heard some of this earlier. I believe in generative cultures. I do not believe in blame. When I ask questions about how leaders engage when there is an outage or something goes wrong in an organization, I am looking for words and actions that are not generative. If I hear things like human error, or that we focus on who made the mistake, those are things that I collect as data points.

I also like to understand what the organization is leveraging to learn. If I hear references to basically anything that has been published by IT Revolution, if I hear things like value stream mapping, Wardley mapping, those types of techniques are indicators to me that an organization is really embracing dynamic learning.

Now you get to see my really awesome slide skills: frowny faces and happy faces. I think words matter. Obviously actions matter more than words, but words are an indicator of actions. If I hear things like IT or cost center, those are usually phrases that I again collect. Output over outcomes, you have heard that today as well. Project versus product. I am also a big believer there is not a single root cause; there are contributing factors. We work in complex systems. These are just some of the terms that I am always listening for as I am making my decision regarding a new role.

As many of you know, over the last couple years a lot of people have made career changes. A group of us started to put together a list of questions that we were leveraging throughout our process of assessing new roles. I am only sharing a few, but at the end you will get my Twitter handle, and if you want the entire list just send me a note and I will get it to you.

I love to ask what a typical workday is like. We know we spend a lot of time in meetings, but I like to probe on what types of meetings. I am okay with meetings that are working meetings or they are driving decisions, so I really like to ask that question and understand what a typical workday is.

This is a big one for me: how are you managing talent? What is the process? What is the hiring process? How are promotions considered? Is it when people are ready, or do you have a cadence? Do you do them in big batches? How does the organization think about talent management? Career development, how is performance managed, all of those things, including the structure. Is it a heavy dependency on HR, or as a leader of a function do I make a lot of those decisions? I try to drive that clarity.

Many of you know that I am going to ask this question. I am very passionate, and I have been part of the DevOps Enterprise Forum and publishing some industry papers with a bunch of great folks around how to leverage consultants in a productive way. I love asking this question. I like to know how organizations think about engaging consultants. Do they do it from an outcome-based approach? How do they ensure that there is not a dependency created? How does the organization take ownership and accountability of how consultants are used?

This is a little bit busy, but these are my beliefs. I have collected these over time, and this is what I am testing for. I am always looking for that generative culture, the dynamic learning organization. Some of these will probably feel familiar after the talks that you heard today. Honoring reality: I used to talk about honoring reality. I added surface reality, because I believe if leaders are not creating a psychologically safe environment, no one is going to tell you reality. You have to be in a position to create that trust so that people tell you.

These are the things that I am looking for when I am talking to organizations: how did they think about these concepts? If I say something like I believe in gemba, I think it is important for leaders to understand the work, not micromanage it. I added, you know, gemba means go and see, not go and tell, because you are not going to tell the team what to do. You are going to learn and understand how you might be able to help.

At the end of the day, when it is all said and done, what I have learned is to stay true to the criteria. I have let myself get distracted by shiny objects, or maybe this role would be really interesting because of insert-shiny-object reason. Go back to the criteria. The criteria has never steered me wrong. Even literally doing the numbers, calculate it and look at the score. It is a great indicator of decisioning, and I can say with high confidence that if anybody wants to talk about details, it has not steered me wrong in any decision that I have made so far throughout my career.

In closing, this is how you can get a hold of me if you want more information on those questions, or if you just have a story to share as well or want to connect on any specifics. Ultimately my goal is just to always be learning. That is it. Thank you.