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  • Writer's pictureAmory Borromeo

Career Advice Questions from You...

Updated: Aug 26, 2020

You all know how much I appreciate conversing with you and I'm always so grateful when people reach out after an event. I love all of the thoughtful questions you send me and I try my best to respond to each of you when you reach out.


Since it takes a lot of courage to ask the question in the first place, I suspect there are folks out there who would like to hear the answers to these same questions. I thought it might be helpful for me to share some common questions and answers with all of you.


Most of these questions popped up after my Developing a Career Roadmap presentation. You can view the recording here or check out the deck here.




When you made your career jump that you considered as a “step back,” how long did it take for you to get to the place you are today? 

I have made this jump more than once. In some cases, I'm able to quickly make moves, but sometimes the company isn't structured to support that. You can usually tell within 6-12 months if your trajectory is aligned with the vision and direction of the company.


In my current role, I took on more and more responsibilities and within 6 months I was running a larger group with direct reports.  It took a little over a year for me to develop the Technology Operations role that I have today.  


Do you have any advice on how to find a company that fits your career vision? 

I wish there was an easy way, but it really takes research and reaching out to your network.  What companies are people talking about with values that resonate with you?  If you want a high growth company, connect with your local economic councils, look for meetups hosted at particular companies you're interested in,


I'd say go to networking events as well but all of that kind of stuff is a bit strange in light of Covid.  I did really strange google searches and borderline creepy LinkedIn reviews to try to understand the types of leaders at a company before I applied.  While I strongly encourage having a prioritized list of what matters to you in your next company or culture, know what you have to have vs what you could live without.  As in most things in my life, I like to leverage matrixes for this type of thing.


When you were transitioning your career, what ultimately made you decide on accepting an offer with Carvana?


What a fun question.  So, the people and the office, on top of all the research I did leading up to the interview process were definitely deciding factors. The truth is that it was actually the last interview that I had, with my now boss, Dan Gill, Carvana's Chief Product Officer, that sold me.  His laid back demeanor coupled with his approach to the interview process made me comfortable right away. But it was one specific question he asked that left me wanting the job more than I did when I walked into the building.  He asked me who I needed to surround myself with in order to become the best version of myself.  It was such a great insight into the culture of Carvana and how they find a way to balance pushing us to whole new levels of excellence, in addition to caring for each and every person, on an individual level. Fortunately for me, Carvana delivered everything I could have asked for and more.  They have found a way to create a collaborative and yet competitive environment, where we all strive to push each other but also do better than we ever thought possible for the sake of our customers.  


What are the beginning steps to creating a ‘career vision,’ especially if you don’t have one? 

I love this question.  If you're new to the workforce, think of the types of activities you did in school or in other hobbies and which of those things you enjoyed the most.  Maybe you led a team, maybe you were student council, maybe you were part of a club or helped organize some kind of event.  If you have professional experience, do the same with the work you've done. 


I'd highly recommend a full brain dump here.  Write everything that comes to mind and then review what you wrote and start organizing it into trends or skills.  Group things together until you can make some sense of what you really like to do.  Once you have themes, start to work out why you like each of those things.  What about that drives you?  Is it the recognition, the impact, the task itself?  Then move into the where and who to understand what kind of environment you need to be in to really feel fulfilled and driven to being the best version of yourself.  


How did you originally create your reporting method? Was it something passed down to you or something you’ve created as a leader?

I had the amazing experience of working for a former Captain in the US Air Force early in my career who prompted me to create a WAR (Weekly Activity Report) to stay in sync with him.  It has changed a lot over time and expanded and shrunk, based on the complexity of my role and the relationship I had with my manager. 


At one point, I treated it more like a weekly stand up that listed what I did, what I'm doing and any blockers.  The point is that this is a tool to align with you manager and will change according to how you best work together.  Someone asked me via LinkedIn about format or tools for this and I let her know it has also changed over the years.  Right now I use gMail templates because my boss and I work well on email.  In the past I've used gDocs or Excel sheets.  Do what works best for you and your direct supervisor.  If you don't know, have the conversation to discover the best solution together.  


Have you felt ‘career crisis’ before? Where you have multiple projects due and very little time. How do you stay organized with everything due? 

I feel like this all of the time!   I love having too much work to do, but it can create a constant pressure.  This is where organization and alignment come into play.  I use my weekly activity reports (WAR) to align on what I need to focus on for the week and that is the only thing that goes on my task list for the week. 


I have a bullet journal system that works for me, where I have a running monthly list of tasks and projects.  If something comes up during the week, it goes on that list, and not on my weekly task list.  (Unless it is truly urgent) Then each week, I look through that list as I create my WAR for the week ahead.  When I have to transfer things to a new month (almost always) I try to move it over in a prioritized order or highlight the items I know I have to get to that month.  A more recent trick is being critical about the items I'm moving over to ensure that only items that truly belong on my list stay on my list. If it doesn't need to be done or doesn't need to be done by me, I work to get it off my list.


What feeds your energy? 

My family and my colleagues.  I constantly strive to be the best version of myself to inspire others.  I look at everything as an opportunity to grow and fuel myself by learning from my mistakes.  And they happen a lot!! It is a hard choice to choose to work while raising a family and I need to feel accomplished in order to not get lost in the inevitable mom guilt.  Life balance is not a real thing. We are all always making sacrifices and trade offs based on what is most important at any given time. Also, I am hyper competitive and love proving people wrong!  Telling me I can't do something is a sure fire way to see it get done.  


How do you know you’re the right person for the job you envision and how do you convince others?

Wow, what a tough question. I actually think the answer is that I do and I don't.  I assume that there is someone better qualified for the job, which is what drives me to fight harder for the chance and then work harder to earn the right to the role. But one thing I know without a doubt is that I can do anything I set my mind on.  I weigh the effort and make the tradeoffs on what kind of sacrifices I'll have to make in order to perform. Once I make the decision to go for it, I go all in. 


Now, I should say, I have been turned down multiple times.  I was told I couldn't have a Business Analyst title (while I was doing the job) because it was a "technical title." So I got a job offer for that title somewhere else.  I was told it would take years for me to advance to director level, so I left and moved through the ranks of another company more quickly.  The takeaway here is that we can't be afraid to try because someone could be better than us or because someone, somewhere wouldn't give us the chance.  We should know for a fact that someone is always better than us and use that to propel us forward to be the best version of ourselves. 


Did it feel strange starting WAR with your manager?

Absolutely! Especially when I was the one initiating it.  I've had other experiences where there was already some kind of reporting or process, where I could just tweak it, which was helpful.  In instances where I start it fresh, I typically simply say I want an "Accountability Partner" and a way to better manage expectations.  Most managers won't mind receiving them and I've never had someone tell me no.  Definitely have the discussion and explain your reasoning.  Remember to share your "Why"  - why is this important?  Why will this benefit the relationship? Why will this help you grow? Why is this worth your time to write and their time to read? If there isn't an obvious business value, how will this help you grow and achieve your goals?  Every supervisor should at least support that. 


How important is title in your career? Should we fight for the title?

I'm the wrong person to ask.  I think it matters differently depending on who you are, what you value, and the weight of titles within your organization.  If it matters to you and it impacts your ability to be effective in what you're trying to accomplish, then go for it.  For me, I've had to influence without authority most of my career, so it matters a lot less to me than most. The only time it has really gotten to me is when I was doing the same job as a male peer and he had the title and I did not.  I'm all about equality so that hit a different nerve.   It seems like more and more often, in younger companies, titles don't really matter. If you're someplace where they do, act like you already have the title and that confidence/assertion can do amazing things.


How can you overcome a stigma that was created based on a male’s negative interaction with you in the workplace? Specifically someone I work with lost his cool in a meeting and disguised it as ‘passion.’ This encounter has reflected more on me than it has on him. Thoughts?

This is a tough question. It is definitely unfair that this happens and honestly, it happens a lot.  It's a shame to hear and I'm sorry you have to experience that.  I wish I had a magic answer. Actually, I wish I didn't have to answer this at all!  We have made a ton of improvements since Women's Suffrage and Equal Pay Acts, but we still have a long way to go. 


The only approach I can think of is to develop a network of advocates to help change the perception.  Find ways to interact in meetings that show you for who you really are and not whatever perception resulted from that incident. Get others to help combat commentary around that perception by standing up for you when they hear it and you should feel comfortable doing the same.  We have to do a better job looking out for each other to fight these kinds of irrational perceptions in the workplace. I speak to a bit of these kinds of behavioral norms in the last WIT presentation I did.  You can see the deck and my narrative in the notes here:  http://bit.ly/CulturalExcellence Maybe there are some readers who can share their thoughts as I'm confident a number of us have dealt with similar situations.



Check out my full presentation on Designing your Career Map for more details.



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