Start 2019 Off Right With a Career Check-in

In my previous life, I was a management consultant. As a consultant, my job was to provide knowledge and expertise to clients on how to solve a problem or challenge and usually involved giving them a set of recommendations on how to proceed. In my experience, even when we were really familiar with the client or problem, the recommendation on what to do did not magically drop into our brains one day in a flash of insight.

Instead, it’s something we would discover, through a rapid but thoughtful process of gathering insight, testing, getting feedback, and then coming up with a recommendation on how to best proceed.


This notion is similar when it comes to making career decisions. As a Career Coach, a common question I get when working with my clients on building their careers is “How do you balance doing your everyday work with thinking about the next career move, or, how do you know when to look (or not look) for a new job?”

These are important and thoughtful concerns — we are not certainly defined by our jobs but they make up a significant portion of how we spend our time each week. And like anything important, putting in time to think and reflect before making a decision is a good thing to do. Over the years, to help me answer these questions I’ve built a series of questions to help me answer some of these questions and figure out how I am feeling about work, which helps inform if I need to make changes.

With that, I like to think of my career as 2-year sprints. During that sprint, I do a major check-in once every six months.  Given that it’s still early in 2019, now is a great time to reflect on where you’ve been, and to start thinking of where you want to go, which is a great time to conduct a quick check-in.  I ask myself the following questions:

  • Am I learning everyday? — I am at my best when I’m most engaged/immersed in my work, and that happens when I’m challenged or when I have to learn something in order to do my job. It’s important for me to make sure that I’m still learning and being challenge.
  • Do I like and respect the people that I am working for and with? — I get my energy by working on high-performing teams, and I do my best work in a supportive and collaborative environment. Furthermore, I value and respect people who treat others with respect. This environment ensures I can do my best work. For this question, it’s about making sure I still enjoy and like working with the people I am working with.


  • Am I committed 100% to doing my best work? — I do my best work and exceed my expectations when I’m fully committed to what I’m doing. I don’t meet my expectations when I’m sort of committed or ambivalent. For this question, it’s about making sure that I’m fully vested into what I’m doing.


  • What have I improved, or strengthened since my last check-in? — As someone who believes in the growth mindset, I believe it’s important to continue growing both strengths and weaknesses. If I can accurately pinpoint skills I’ve developed or development areas that I’ve improved since my last check in, I know that I’m probably happy where I am.


  • Is there something else that’s taking a significant portion of my mindshare or attention? — I think about the things that are on my mind, and pay attention to my thoughts. Can I identify a specific problem, challenge, or topic that I’m constantly thinking about? If my time is spend on what is currently in front of me, I know I’m probably progressing down the right path. But if it’s on something else, I’ll need to revisit what that is, and understand why I’m focusing on it so much.

For me, it’s about doing a check-in every once in awhile to take stock of what I am doing, how I am doing, and to get a sense of if I need to make changes. Changes can mean anything from adding additional things in my personal life to help with my well-being, to reaching out to mentors for advice, picking up a side project, or in some cases,  starting the process of finding a new job. The focus for me is getting clarity on what’s currently going on, and figuring out the best way to keep going. In some cases, nothing needs to be done, but in others, changes are needed.

As I’ve conducted these check-ins numerous times over my career, I’ve learned a few things along the way:

There are always ups and downs — That’s okay, and it’s part of life and your career. Work is just that — Work! Which mens, there are ups and downs and stressful weeks. This happens and is part of life

You need to give it time — In my experience both as a professional and career coach, I’ve come to believe you need at least 6–8 months to get a first set of hypotheses/feedback on a job. If you stay for anything less, you might not get the full cycle (save for a few exceptions)

Considering The Future is a good thing — It can be easy to put your blinders on and execute on the tasks in front of you, so thinking about what’s next is a good thing to do. However, it’s important to stay focused on the task at hand. Try to time box your future planning, or, save it for times when you have more energy/time to devote to other things

If I can answer yes with supporting evidence for all those questions, that’s usually a green light to keep going. If there is a no, or a lack of supporting evidence to any of those questions it means I need to do some additional probing to understand the root cause.

In some cases, there are factors that cause me to answer no that I recognize and appreciate but am OK with moving forward on. In other cases, I need to either A) dig further, B) create an action plan for how I am going to work through it or C) it’s time for me to put the wheels in motion for moving on to my next opportunity

It’s not a binary decision of Yes/No, but it’s a simple framework for how I like to evaluate my job in the arc of my career. The main takeaway here is not the questions or the check-ins but the ability to dig deeper into understanding what’s causing my feelings and to do something about it, whether that means keeping up the great work or starting to search for something new.

I encourage everyone to come up with their own framework and series of questions that they can reflect on every few months. I think you’ll find it will help you figure out what’s going on, what the root of it is, and what actions you can take to make the right next move.


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3 Must-Have Skills for becoming a Great Product Marketer

Over the past five years, Product Marketing has become an increasingly popular role at tech companies ranging from emerging startups to established tech titans. But the role and responsibilities of a Product Marketer varies company to company. Shyna Zhang knows this well, having launched products and led Product Marketing teams at fast growing startups (Marketo) and large tech titans (Microsoft)

Recently, Shyna left to start a new venture, and we got the chance to talk to her about what she is working on as The Founder of Rigging Academy. During our conversation, Shyna shared her journey to becoming a Product Marketer, what a good product marketer looks like, and her advice for those interested in transitioning into or building a career as a Product Marketer.

CareerSchooled: Over your career, you’ve made your mark doing product marketing for a number of multinational organizations and tech startups. But thinking back to your childhood for a second, what did you think you were going to be when you were growing up?

As with most of America, I was glued to the television watching Michelle Kwan try to bring home the gold medal in the Salt Lake City Olympics after getting ‘robbed’ in Nagano. Growing up in Louisiana, there were few Asian role models around me, let alone female, let alone in mainstream media. I was convinced that despite living in a place that averaged temperatures of 100 degrees with 90% humidity for the better half of the year, my future was in figure skating. As you can imagine for obvious reasons, that quickly didn’t work out.

When declaring a major for college, I realized that I was really interested in people – understanding what makes them tick, what motivates them, and how they work well (or not so well) together. I floated the idea of being a Sociologist or Journalist with my tiger mom, who quickly dismissed that idea and a more practical Business Finance degree was decided upon :). 

Although in hindsight, it wasn’t a good choice or fit for a number of reasons. One of the main ones being that I’m probably one of the only Asians in history that scored better on her SAT Verbal than the math portion.

CareerSchooled: How did you get your career started in Product Marketing?

Getting into marketing was a combination of luck, curiosity and hard work. During my junior year of college at the University of Texas, I realized that I wasn’t good at finance – the degree I was studying – and that the bachelor’s degree in finance that I was going to end up with would be useless for me. I was fortunate to get internships at Accenture and Microsoft in their marketing teams, through alumni of the University of Texas who were willing to take a chance on me. The experiences I gained during those internships helped me to realize that a career in marketing offered me the opportunity to be creative, plus I could define and own what success looks like.


My early marketing roles, like my internships, were in broad marketing roles that provided clear visibility into how an entire business operates and makes money. At Microsoft, I learned about general management – that is, how to run a business across marketing, sales, customer readiness, partner services and more. The job also gave me the opportunity to live in Singapore working in a regional role with responsibility across Southeast Asia, Australia and Korea. Joining Marketo taught me the importance of the story-telling aspects of marketing and how important it is to create messaging that’s repeatable, concise and memorable.


CareerSchooled: What are some of the challenges that Product Marketers face in their day to day jobs?

Measurement is a huge challenge that some of the most talented PMMs struggle with. Sales has a clear quota that they need to hit, while Product teams may have clear adoption or MAU goals. Product Marketing often owns messaging, positioning, storytelling – functions that can seem nebulous when it comes to defining a hard value to the organization. I’ve found that aligning with revenue metrics is always a good place to be for PMM (ie. revenue, share, time to chose, win rate, etc..) as well as developing good partnerships throughout the organization.

Impact and influence is also something that’s hard to achieve within the organization, but critical to the success of PMM. Often PMM doesn’t have direct ownership via reporting structure of Sales, Demand Generation, Customer Success etc.., yet are held to business outcomes such as pipeline, revenue, time to close, win rate, renewal rate, etc… It’s important to be able to make your case, build the relationships, and lay the foundation to be able to drive change throughout an organization.  

CareerSchooled: Throughout your career as a Product Marketer, what’s a project, deliverable, or experience that you are especially proud of?

I left a pretty cushy life in Seattle at the age of 24 to move to Singapore to run a $500M P&L for Microsoft across Asia Pacific and launch a product in less than 3 months. Don’t feel sorry for me, but it was probably the most challenging professionally and personally for me. Leaving my support network and everything that I knew behind and jumping into a stressful work environment (in addition to figuring out my personal life) covering 9 countries led me to lose a patch of hair about the size of a half dollar from the side of my head. Yes, I had a bald spot at the age of 25 :).

As the saying goes, ‘what doesn’t kill me, makes me stronger.’ I learned a lot about resilience, grit, determination and my pain tolerance from that experience. I ended up getting promoted at the end of that year, but more importantly, I learned a lot about myself and what I’m capable of.

CareerSchooled: Like any job, there are numerous skills needed to be a great product marketer. What are 2-3 skills that you believe are critical to being a Product Marketer?

Communication through impact and influence across the organization (storytelling).

PMM doesn’t own sales, demand generation, customer success, etc.. however, we need their partnership to hit our goals and provide us feedback. Building these relationships and being able to share ideas/proposals across the organization in a way that clearly demonstrates the value to them is important to make impact.

Deep buyer (and stakeholder) empathy.

Any marketer worth their salt can talk about their own solution/product. The trick is to figure out how to speak to the value/benefits of your solution in your user’s language. You’re selling to Oil and Gas Executives? How does your solution benefit upstream vs downstream initiatives? To effectively talk about the benefits of your solution, you have to develop deep empathy for your buyer. Starts with speaking with them and getting into their shoes. What are their dreams? What are their aspirations? What are their painpoints? What are their fears?

Ruthless prioritize to get shit done.

You’ll never have enough time and resources to get all of the things that the organization is requesting complete. You’ll have to work with your stakeholders to ruthlessly prioritize, otherwise, you’ll never get anything done or burnout. Figure out what’s urgent vs important and where your points of leverage (scale) are. If you create this collateral, are there additional use cases for it or is it just a one off to close a deal or a one specific campaign?


Careerschooled: What advice do you have for someone who doesn’t work in Product Marketing, but wants to make the transition into Product Marketing?

1.Build your PMM portfolio

Similar to an artist who may have a portfolio of their best work that they are proud to display, I always ask to see a PMM (or a potential PMM’s) portfolio of work. It could be a compilation of blogs, ebooks, content, decks, etc.. that they have created for personal value or for previous roles. I want to see that you’re a talented storytelling, that you understand how to get across a message in a compelling way, and that you are able to succinctly explain something that may be complicated.

2. Build your Network

I find that the term ‘networking’ can be really awkward and painful and have found myself eating chocolates on the couch instead of going to an industry event to shake random people’s hands while awkwardly juggling a drink in the other hand. However, I’ve found that often going in with the mindset of learning something new through interesting people helps. Instead of

3. Be curious. That can help you to hustle to get as many informal, social interviews as possible.

It can be easy to be tunnel visioned when looking for job or career transition. People will be much more open and willing to help if you invest in building a relationship first. That requires being genuinely interested in their journey, their learnings, and seeking their guidance. People want to help, however, when the ask comes off as purely transactional, it can not feel as fulfilling. Once you learn about other people’s interests and initiatives, brainstorm how you could be of value and help. Beautiful things happen when we are willing to bring our cumulative gifts to the table. 🙂

CareerSchooled: While you’re a seasoned Product Marketer for many notable tech startups, you recently transitioned into the role of a Founder. What are you up too now and what are you working on?

Specifically for product marketing, I help run a community called Product Marketing Masters. We’re on a mission to educate the next wave of product marketers with real world examples and practical guidance. We hold monthly events and workshops on topics like Messaging & Positioning, Go To Market Strategy, Pricing and Packaging, etc.. in the Bay Area.. I frequently have people reach out to me for career advice or information about product marketing. Without a single source of information to point people towards, I wanted to bring practical guidance to help create the next generation of product marketers.  I was lucky enough to find a tribe of other women who felt the same way – we now work together as the Product Marketing Masters. I’d encourage anyone interested in product marketing to join our Product Marketing Masters Facebook group, Meetup, and

I’m also passionate about developing talent, especially those earlier in their careers. I run a minority talent incubator called Rigging Academy. Minorities tend to self-select out of opportunities consciously or unconsciously due to lack of confidence or not knowing the rules of how Corporate America operates. I’m focusing on helping people develop the soft skills they need to succeed in a professional environment (ie. negotiating salary, marketing yourself, etc.). I’m building an online community consisting a virtual classroom, group work, and 1-on-1 coaching. Sound interesting? Sign up for the Spring 2019 waitlist!

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How to Succeed In a New Job

Getting a job is just the beginning

Successfully navigating an interview process to get a job is a challenging and arduous process, so it only makes sense to celebrate and breathe a sigh of relief once you land an offer. However, the real challenge begins when you show up on the first day and you are expected to start delivering results. Afterall, we’re not rewarded for getting the job, but for what we do in the job.

A few months ago, I started a new job, and since it was the first time in a few years that I’ve actually started a new job I wanted to take a thoughtful and strategic approach. In a recent survey, 75% of hiring managers said they made a bad hire, and I was determined to not fall victim to that statistic.


Furthermore, as someone with goals and aspirations, I really was excited about succeeding and taking on a ton of responsibility for my new exciting job. But I recognized there’s a learning curve, and that Rome certainly wasn’t built in a day, so I created a plan to do my best to decrease the learning curve and accelerate my “time to market” in my ability to deliver results. I believe have been instrumental in helping me get up to speed, contribute quickly, and build credibility and my reputation within my team.


Go on a listening tour

As Alexander Hamilton said, “Talk less, smile more.” Politicians use listening tours as a means to shake hands and kiss babies, but in the context of a new job they are a great tool for meeting people and learning the ins and outs of the culture of your new organization.


Listening to others to learn about their job, department and place in the organization helps you understand the organizational structure, builds your reputation, and gives you information on how things get done at your new company. Furthermore, in the event that the person you talk to is someone you have to work with, it helps build a relationship.


During my first week, I asked my team to help me to put together a list of people that I should reach out to and talk to. I asked for people that were either A) people I would be working with or B) people who had a good reputation within the company and had be a veteran of the company.


From there, I went and made the effort to reach out and speak to these people, to learn about their role in the organization, best practices, and if necessary, how we might work together. This was a valuable opportunity for me to learn but also to start building relationships, which was critical for me as I work in a very large company.

Learn and Set Expectations

Understanding what’s expected of you is critical to success. Learning what the expectations are helps you prioritize your work, and helps you understand the quality and effort you need to exhibit in order to be a top performer. The earlier you do this, the better off you’ll be in ensuring you are meeting and exceeding expectations.


To do this, set aside time with your manager to ask about what the expectations are, and clearly articulate them to make sure you both are on the same page. In addition to explicitly asking about your roles, responsibilities and general expectations, consider asking questions like:

  • Who’s an example of a top performer and what does she do that stands out?
  • What are some best practices around working and collaborating with others?
  • Is it better for me to schedule a regular check in, or are you more comfortable coming on an as needed basis?


While it’s important to learn the expectations of someone in your role, it’s also important to acknowledge that you have a role in setting those expectations as well, so don’t be afraid to use your judgment in shaping those expectations based off of your own opinion and perspective.

During my first week, I made sure to talk to my manager and my team to get a better sense of what my role was going to be. I asked questions around what projects I should be working on, how to prioritize my time, and the best ways to ask for feedback.


Create Your Information Diet

As a regular consumer of content, I rely on digital and social channels for relevant information and to help with informal learning and “getting smart” on topics in a quick manner. Since I was starting a new job, I had to make sure my content sources were up to date.  I went and updated my content and information intake diet to reflect the sources of information and topics that I wanted to get smart on for my new role.

That meant finding new sources and websites to read for industry information, finding new sources industry experts to follow on Twitter, and updating the terms I get reminders on via Google News. From there, I made sure to check these sources daily, and tried to read during the evenings and weekends to make sure I was informed. If you aren’t doing this, consider signing up for a Twitter account, downloading a content reader like Pocket, or setting Google alerts to key topics that are relevant to your job. If you want to go a step further, ask your colleagues what they are reading. I think you’ll be surprised at how much you can learn.


Take on what you can take on

Research suggest it takes about 8 months to be fully productive in a new role.  While you do have time to learn, a great way to get started is to start raising your hand for anything that you feel you can take on or contribute to.


For example, if your team needs someone to do a research report and that’s something you’re comfortable with, raise your hand to work on it. If you are a little uncertain, offer at least to be a reviewer, or to tag team it with someone else. Taking the initiative will allow you to contribute, get you more familiar with your job, and also win some brownie points with your co-workers and manager.


During my second week, I was in a meeting where we began talking about a project that needed some support, and it was on something that i had done in my previous job. While it wasn’t in my direct job description, I volunteered for it anyway, and made an impact right away on the project because of my previous experience. The project lead was very grateful for my support, and it also gave me confidence in my abilities to contribute.


Leverage your strengths (and weaknesses) to your advantage

Everyone has a set of strengths and weaknesses, and since you got a new job, clearly your new employer is betting on you using your strengths to make contributions. Take the time to articulate out your strengths, and to share them with your manager or your teammates, so you both can begin thinking on how you might contribute to projects or deliverables. And while everyone has strengths, all of us have weaknesses. Use this as a chance to identify training or learning opportunities, and to build up some competency in areas where you can improve upon.


Create a User Manual

Last year, I stumbled across Abby Falik’s user manual that she created for her direct reports. The purpose of it was to explain her values, preferences, quirks, and overall leadership style to others in a transparent way, so others could understand her better and ultimately work with her more effectively.


Since it can take time to adjust to a new environment and build relationships with colleagues, I decided to write my own user manual. While I’m not a CEO of an organization, since I was new, I thought it would be helpful for my teammates to know me in a more transparent way, and to start our relationship off as best as I could. In it, I shared my values, preferences, workstyles, and offered tips on how to work with me.  


Additionally, I offered to help other write their own user manuals. My team embraced the idea, and while it’s early, we seem to be working together well. Additionally, they shared it broadly with the rest of the organization, and now user manuals are sprouting up on a number of different teams.


Build a question log

There is so much to learn when you start a new job that at times, everything can seem overwhelming. To combat the information overload, I created a document on my computer called a question log.


On the first day, I started a question log, and everytime I had a question that I didn’t know the answer to, I would write it down. Each week, I would meet with someone on my team, and for 10-15 minutes we would go over the questions that were in my question look. Not only was this helpful to me, as I got the answers to my questions, but on a few occasions the question helped identify an issue or an opportunity and it got raised to the broader team. Being new is tough because there’s so much you don’t know, but it’s also a great opportunity to question the status quo to uncover opportunities that others who have been there might have overlooked.


First impressions mean a lot, which is why it’s really important to start off a new job in a positive manner. While it’s unreasonable to expect to knock it out of the park right away, investing the time and being proactive about beginning your job will set yourself up for longer term success.