Tag Archives: careers

Taking On Too Much

There is always a time in your career where you’re asked to take on more responsibility. This is normally a good sign! It means your manager or CEO or whoever trusts you and seeks you out when problems arise. If you’re like me when I was earlier in my career, you always said yes. I thought of this as moments to increase responsibility, learn new skills, and have more impact. Now that I’m older, I am no longer so eager to take on more. When these situations arrive in my career now, I take real stock on my capability to handle the increase in responsibility. Today, I’ll walk you through the three most common scenarios you’re likely to find yourself in when this happens, and some recommendations on what to do in each situation.

Option 1: Scale
In the first situation, you have been spending years building up a team and/or some sort of scope you’re comfortable with. It could be an entire function like product, a group within a function like the email marketing team, or, if you’re an IC, an area of the code or a particular skill set the company needs. By all accounts, you’re excelling in this scope. If you’re stuck in this structure for too long, and you’re like me, you tend to get bored and are looking for new challenges anyway. This is a great time to accept the new challenge, and either empower your team with more ownership, or use some of the slack time you’ve built up from automation or process improvement to provide more value. This is usually not a confusing move. I only call attention to it in contrast to the other situations I’ll talk about in the rest of the post.


Sam Porter Bridges carries the weight of the world on his back. Don’t do this.

Option 2: Prioritize
In the second situation, you do not feel as if you’re excelling yet. You might still be building your team if you’re some sort of manager, or still learning the function if you’re an IC. Taking on more responsibility might prevent you from succeeding in your primary job, so it’s a pretty big risk. In situations like this, I generally advise people to do what they do in any sort of situation where they have too many things to do and not enough time to do it: prioritize. The difference in this situation is you have to force the person asking you for the additional scope (if they are more senior) to prioritize for you.

For example, I was working with an analyst, and he got a request from an executive at the company for an analysis he wasn’t planning on. He already had a lot of high priority stuff on his plate, so he was confused as to what to do. I told him to email back the executive, show her everything he was prioritizing and how and where this request should fit in. This forces people to acknowledge the value of the work you are currently doing and the amount of time you realistically have available for work effort. If you’re more senior, you can talk about the scope you currently have and whether it might be appropriate to shed some of that scope or de-prioritize progress to accommodate this new area. That’s a very healthy conversation to have.

Option 3: Stretch
In the third scenario, there is no ability to prioritize or shed scope, and you just have to stretch your ability. It’s important to understand this is not a sustainable state. The only way stretching works is if it is short term until you can figure out how to prioritize. Not doing so will result in failure or burnout.

Triage
There are times in a company’s lifecycle (frequently described as war time) where it feels like you might be in a position for a prolonged stretch. What this really means is you need to switch to a variation of option 2 called triage. Triage actually comes from the medical field, and is a process of extreme prioritization of who to treat when you have a large number of wounded or sick, invented for wars, of course. The process focuses on helping what you have the opportunity to meaningfully help on, ignoring things that will likely get better with you, and accepting that some things will go poorly because you do not have the resources to prioritize everything. This process is mostly associated with bugs as a company always has more bugs than it can possibly fix, but I prefer to reserve its use for periods of war time when some things will fail, and you are acknowledging that beforehand.

A mistake that can be made in triage mode inside an organization is to make a decision on what to prioritize and not re-evaluate over time or check on your assumptions. Prioritization in war time is a best guess on what’s most critical, what can fail, and what might be fine without you. If you make a mistake on the latter, it may become more critical, forcing you to change prioritization. And it can be tough to remember to stop and check up on things you’re not focused on to see how they’re doing, and also to remember to re-evaluate and re-prioritize. But it’s important to do so.


More responsibility can be a great or a troubling thing. You don’t want to fall over because too much is on your shoulders. Being honest about your capabilities at the time and the mode you need to be operating in can help prevent you from failing by being burdened with more responsibility than you can handle. Tomorrow is in your hands.

Currently listening to Run with the Floating, Weightless Slowness to by Kelpe.

How I Grew This Podcast, and How I Unintentionally Started Working on Growth

I caught up recently with Mada Seghete, co-founder of Branch Metrics on her new podcast “How I Grew This”. In the podcast, I talk about my career in growth including some of my early experiments before I even had a real job. You can listen here:

I thought I’d go into a little bit more detail in this post despite how embarrassing it is.

When people ask about how I got into working on growth, I usually respond by talking about my job at Apartments.com, and how I had to measure everything the marketing team was doing to grow the business. It turns out measuring everything and its impact on growth gives you a pretty good understanding of the growth channels. And for me, one of the biggest lessons was that it was none of the things you learned about in marketing classes at school. It was things like SEO, affiliate marketing, paid search, distribution partnerships, et al. As I automated more of the tracking, it gave me more time to actually work on optimizing those channels. This is all true, but it’s not actually the start. So I’m going to talk about the start in hopes it helps other people figure out how to find opportunities to develop skills and learn. This is going to be a somewhat autobiographical post, and it may not be useful, but multiple people have said I should write in more detail about it, so I am.

My High School Passion: User Generated Content
I was pretty early to the user generated content trend. In high school. I spent a lot of time on AskMe.com, which was basically a pre-bubble Quora, answering questions about a range of topics including music, video games, and history. I answered over a couple thousand questions there. I also hung around the IGN message boards, which was the 3rd largest forum on the internet at the time. I became a moderator on IGN eventually for some of the music and video game boards. This is pre-Facebook, pre-reddit, pre-most things you spend time on the internet with. One interesting thing is how all of those multi-billion dollar companies existed in some form back then; they just didn’t become the valuable companies:

  • AIM = WhatsApp
  • IGN = reddit
  • AskMe = Quora

My College Obsession: Tony Hawk’s Pro Skater
In college, I started playing a lot of Tony Hawk’s Pro Skater 3 on the GameCube. I got pretty good at it. When I went online, I eventually found a community of the early online players playing on the Playstation. They were a lot better than me, and posted videos for download of them reaching new high scores. This was pre-Youtube, so they used various archaic methods of recording (I, for example, used a capture card and a VCR to record the play), uploaded them to a server, and you had to download them to play the videos locally on your computer.

I watched all of the new videos. Not only were they entertaining, but they helped me learn how to get better myself. All of the best players used loops of the level to repeatedly hit parts of the level that allowed them to do valuable tricks. Many people started to post tutorials of their loops. You can see one of the loops I used for a good score here (sorry for the quality. All of this was recorded before Youtube existed, and when we finally did upload things to YouTube, they didn’t support high quality yet):

When Tony Hawk’s Pro Skater 4 came out, it became super easy for these players to score billions of points in one combo using these loops, so the quest for higher and higher scores lost its luster. Instead, the best players switched to showcasing themselves doing stylish combos without ever touching the ground. They called these videos “no manuals” or “nm’s” as the manual was a trick introduced in Tony Hawk’s Pro Skater 2 to link combos on the ground. Essentially, these players challenged themselves to play Tony Hawk’s Pro Skater 4 as if it were the first Tony Hawk’s Pro Skater. The entire community shifted from a score based system to a style based system.

When Tony Hawk’s Underground came out, the community didn’t love many of the changes. You could now walk to link combos, which made something that was too easy for the best players even easier, and people stopped posting videos. I was dismayed as well, because the volume of content coming from the community dropped precipitously.

My First Growth Loop: The Get There Challenges
Worried that this community I loved was dying, I tried to think of ways to revive the community. I essentially needed a way to prompt people to post stylish videos. I came up with an idea. I would post a screenshot of a piece of a level in one of the Tony Hawk games to start. I’d post another screenshot of a place you had to get to in the same combo. And you had to do all of this without touching the ground (no manuals, walking, or reverts). The first to complete it got to post the next challenge. I posted two of them to make sure someone would bite, called them the “Get There Challenges”, and a player named Milky posted of a video of himself completing the second. I awarded him the win and challenged him to post the next challenge. He did, and the Get There Challenges were born. Within a day, someone had beaten Milky’s challenge. The loop had officially begun.

By the eighth challenge, the community started adding variations, such as shortest to complete, coolest version to complete, and sub-challenges. Eventually, some even allowed manuals. A website was built (not by me) to host them officially, and a bunch of copycat websites tried to start their own. GT’s (as they had become known) became a pillar of the Tony Hawk’s Pro Skater online community. Over 300 challenges were consecutively posted and completed over the course of the next three years.

Most of these videos are lost to time. Mike, one of the best players in the community, did create a video commemorating 100 challenges, which is probably the best introduction to the concept. Apologies for the video quality, the out of context teenage jokes, and most importantly, the music choices used in the video.

Now, I am probably an idiot for not using this concept to build a billion dollar business ten years before esports and three years before Youtube became a thing. But the framework of the Get There challenges continues to serve me in my career in other ways. I have come to call these loops content loops and not viral loops as what they do is generate content that attracts people instead of invites. I have built a course on them and talked about them. The Get There challenges have a similar dynamic to how Eventbrite (event listings), GrubHub (menus), and Pinterest (boards) have grown. People mistake this as an SEO strategy, but it’s not. As long as you have a place for the content to be discoverable, it can be a loop if enough people interact with it.

There is much more of an opportunity today to leverage your hobbies for learning opportunities than there were when I was a teenager, whether it’s new creation tools available or all of these new online communities. You may be surprised what you learn from them and how they can inform your eventual career.

Bonus content with much better music:


Currently listening to Ritorno by Andrea.

Thinking Outside the Job Title Box: How to Thrive in Undefined Roles

As a leader of a large team, the members of my team tend to have pretty well-defined roles, like designer, or product manager, or researcher. They also tend to interface with other employees of the company with pretty well-defined roles like engineers, analysts, data scientists, etc. Now, most of the time, these well-defined roles operate in cross-functional teams. But, what if you don’t operate within one of those roles, or don’t want to fit the mold of these well-defined roles? How do you work with teams? To answer that, it may first be helpful to understand how these teams form.

“In the beginning, there was an engineer.”

Most startups begin with an engineer building something from scratch. As the company scales, usually a designer is added next. Then, as keeping track of projects between the designer(s) and engineer(s) becomes onerous, a product manager is added. Then, as the team scales and problems become harder, the product manager and engineer(s) don’t have enough time to fulfill the analytical needs of the team, so they hire an analyst. Then, keeping up with users becomes too time consuming for the designer or product manager, so they add a researcher, etc. This is an overly simple example, but all cross-functional teams grow larger as the company scales, with more specialized roles over time. One issue you may have if you don’t fit into this model is that you want to perform a more specialized role than the company has scaled into needing yet.

The opposite can also be true. You may want to do bits and pieces of a well-defined role, but not all of it, or may want to combine some elements of a few different roles into your job. Either of these situations can be totally fine. But each require a more tactical, subtle approach to working with teams than fitting within well-defined roles. When people outside of the cross-functional teams want to work with these cross-functional teams, they frequently perceive friction. They interpret this as political, when in fact, it is structural.

By definition, when you don’t have a clearly defined role to others, they do not know how to work with you. The onus is on you to prove value so that they want to work with you, because they don’t have to. Usually, my advice when people come to me with these problems is to switch to a more defined role. There may be a valid reason to leave your role less defined though, and in this case, I propose a framework for finding a valuable fit within a cross-functional team.

While all cross-functional teams have well-defined roles on paper, in reality, for all the needs of a team, people within the cross-functional team trade off responsibilities based on skill set and interest. You may have a PM who’s better at execution, so the designer takes on strategic duties, for example. What you’re trying to find with a less defined role is a team that has a need for a skill set, and wants someone to fulfill that need.

What happens in each of these boxes? Well, if your role is not needed or wanted, then you don’t get an opportunity to help. If your role is wanted, but not needed, you tend to be superfluous and lowly leveraged. If your role is needed, but not wanted, you experience rejection. If your role is wanted and needed, that’s where the magic happens. You integrate into the cross-functional team well, help them achieve their goals, and likely are happy in what you’re doing.

Two Tips to Make These Roles Work

#1 Get a senior leader to sponsor your effort
It’s almost impossible to make this type of role if your manager and ideally someone very senior in the organization support it. If senior leaders are very strict about team formation, it just might not be the company where you can be successful in a non-uniform role. Also, if your manager doesn’t support the direction you’re targeting, there will be a big mismatch come review time that will stifle your career.

One way to be more successful with managers and senior leaders is to be very clear why you want to work this way and what value it adds to the company. I would not recommend going to managers and senior leaders suggesting you not fit a typical role in the organization, and then ask how you can be effective. You are not giving them two problems: 1) someone who won’t fit into the traditional organizational structure and 2) someone who doesn’t know how to help the company. For many managers, this would trigger them to ask why you’re at the company in the first place if you don’t know how to help.

#2 Approach teams with humility
Your approach to talking to managers and senior leaders about your role should be very different from how you approach teams. While with managers and senior leaders, you want to make a clear case of the value you can add and what you want to do, that can not work so well for approaching teams. A better approach gets across a few key points:

  • You’re interested in the problem they’re working on
  • You think they are doing interesting work
  • You’re just here to help in whatever way you can
  • These are the skill sets you have that may be valuable
  • Finally, the ask: What can I help with?

Whether you have a traditional or non-traditional role in a team, the first step is building trust, and that is usually earned by doing smaller tasks the team is not getting to and would like help on. From there, you earn the right to work on more critical tasks. It may take some time to get to the role you’re most interested in playing on the team, and that is normal.


At Eventbrite, we have multiple people who sit outside the traditional paradigm of well-defined roles who are thriving. They all found a way to add value to a team that was wanted and not competitive, and the team operates better for it. But this all happens on an opt-in basis. The teams chose to accept them. If you want to play outside the lines, you have to understand that other teams playing with you is entirely opt-in on their part. This is the risk of not participating in the structure the company operates in; you may find opportunities to help that the team isn’t welcoming to, and there’s nothing you can do about it.

Create Milestones for Your New Job

People are afraid of taking new jobs. There is a risk of failure of the company you’re joining and potentially of yourself in the role you are accepting. But we all need to accept new jobs at some point. What you should think about is how to cap the downside risk of the two potential situations above. This is indeed possible. I will walk you through my approach.

When you accept a new job, a very healthy practice is to project out the opportunity over a period of time. I like to use increments of six months. What I recommend is you create a document for your job that predicts how the company has evolved, and you yourself have evolved over that time period. This document should ask the following questions:

#1 What should the trajectory of the company be at this time?

This can be represented by numbers, strategic initiatives, funding rounds, whatever makes sense for your mind. Actually, the more the better.

#2 What should my trajectory be at this time?

This can be represented in terms of what you accomplished, what responsibility you accumulated, how much you’re making, what you’ve learned. Again, the more the better.

Okay, so when you join the company, you write this document for let’s say six months, 12 months, and 18 months into the job. When those milestones occur, reflect back on this document and ask the following questions:

#1 Is the company on track?

Predictions are hard, of course, but being on track is great, being ahead of track is awesome, and being off track may be a cause for concern.

#2 Am I on track?

It’s almost as important to ask if your trajectory is on track. Are you learning what you thought you would, accomplishing what you thought you would, making as much as you thought, accumulating the responsibility you hoped for? All of that should be addressed.

If the answer to both of these questions is on track or ahead of track, amazing. You should feel confident continuing to work at the company. If either of these questions is no, however, you need to ask yourself two additional questions.

#1 Can it get back on track?

Let’s say the company is off track. Do you believe in a reasonable plan to get back on track. Was it a one time setback, or are we too far off course to hit the objectives you initially wrote? Similarly for yourself. If only one of the answers above was no, it creates different implications. A fast growing company, but not growing yourself creates a free rider problem for your career. A company where you’re growing yourself, but the company is off target may mean all you’re learning won’t be valued by the market if the company doesn’t end up doing well.

#2 If not, am I comfortable with the new track?

If you’re not on track and don’t feel you can get back on track, you have to ask if you’re comfortable with the new track. This is common. You may have set to high a goal, but things are still objectively going well. That’s fine. You do want to make sure you’re not justifying a mediocre or bad situation because it makes you uncomfortable.

If you follow this process, it should let you know if the opportunity you initially thought was worthwhile isn’t there. The key is when you learn this that you don’t continue to stay. If the company and/or yourself on not on track, you don’t expect to get it on track, and you’re not comfortable with the track, you should find a new job. As long as you change jobs when when you reflect every six months and see this, the risk is mitigated. The real risk is staying with a company a long time that is off track for itself and your career, with no way of getting back on, and it’s sacrificing your potential. Those are the only real career mistakes. So, go ahead and take that new job. But use this framework to be honest with yourself about whether it’s working out or not. And if it’s not, find a new one.

Currently listening to Between Two Selves by Octa Octa.

The Life and Death of Product Marketing

This is part two in likely a three part series on career paths. You can read about the analyst career path here.

As someone who majored in marketing in undergrad and has an MBA with a concentration in marketing, I receive a lot of career advice requests from up and coming marketers. My feedback is usually a wake up call and not very pleasant. Marketing, especially in a technology company, has been suffering a death from a thousand cuts for years now. There are a few reasons for this. As I blogged about before, marketing’s definition grew too broad for one area to be an effective owner. An area I haven’t talked about before is how many roles in marketing are largely a response to engineering constraints. And with computer science grads multiplying like rabbits years after year, those engineering constraints are starting to relax a bit. I’ll analyze some roles in particular who I think are the most affected by this over the next five to ten years. I’ll start with product marketing.

Product marketing has suffered from an identity crisis as long as I have known the term. Product marketing, when done correctly (which rarely happens), is usually in charge of three things:

  • Deciding a soon to be released product’s positioning and messaging
  • Launching the product and making sure users (in B2C) or customers and salespeople (in B2B) understand its value
  • Drive demand and usage of the product

What that means in practice is that with well oiled product marketing teams, they owned the relationship with the consumer or customer and the outlets for how to reach them. This meant they talked to customers one on one and ran surveys. They managed email outreach, press strategy, potentially even an ad budget.

As you look at these responsibilities, it gets easy to see how this definition falls apart in many companies. For one, many companies don’t launch that many new products or features each year. Teams now have copywriters that integrate with product teams to test messaging iteratively.

Launching a feature is about that feature’s journey for feature/product fit, which means it rolls out in small experiments instead of a big press push. A press push would only be justified if the feature is successful in its experiments. A feature launch’s importance is inversely correlated to the number of users it is intended to reach and only weakly correlated to market power, which is why product marketing has always been more effective at B2B companies, and large ones at that.

Product teams now are more likely to be staffed with user researchers who specialize in gleaning insights from users and customers, and may even dedicated quantitative researchers as well for survey design. Pinterest had both, for example. Even if these are not staffed, as product managers have shifted from executional roles to strategic ones over time, they frequently see understanding the user or customer as their responsibility. Designers on product teams frequently feel the same.

Lastly, when thinking about driving demand and usage, that again is something product teams should only care about once they know the feature is driving value. At that point, ever more prevalent growth teams in charge of overall product growth decide how to use growth of that feature as tool to overall product growth. These are cross-functional teams between design, product, analytics, and engineering, and only sometimes include marketers.

The jack of all trades design of the product marketer role is being attacked on all sides as teams determine how to more effectively reach their users or customers and build things they will use. I don’t see these trends as a failure of the product marketing function. In many ways, it’s the opposite. You should always be trying to obsolete your role in a company. All of these responsibilities product marketing owned now being prioritized or specialized in by other functions shows that organizations now understand the marketing of their own products is important and can’t be outsourced at the end of development.

That said, this transition does leave current product marketers in an untenuous position, and many have been asking me what they should do. I see three opportunities that are available for product marketers.

Option 1: Migrate into Product Management
Product marketers build relationships with product teams already. They should start to leverage this for opportunities to work on product management projects, not just to launch them, but to actually work with engineers and designers to build them. These projects are fairly easy to find as product managers are always strapped for time. Once a product marketer does a few projects successfully, I have found their migration to full-time product manager happen pretty seamlessly at multiple companies. Anecdotally, product marketers tend to become very successful product managers because they focus on understanding users and are great at framing the products they build for user value and having users understand that value.

Option 2: Migrate into User Research
Companies are always looking for more user researchers, and they are product managers’ and designers’ best friends. Product marketers already excel at talking to users. The migration here is more about the in between of product marketers focused historically. Instead of soliciting ideas and selling solutions, user researchers receive feedback on potential solutions in process or problems with the current product by watching current product use. There are dedicated programs where you can learn the tools of the trade for user research, and some companies are training people in user research internally because they are so short-staffed. Even if the latter is not available, approaching user research leaders and asking about opportunities to break into their team are usually welcome, and can start, like with product management, on some distinct projects before migrating full time.

Option 3: Move into Dedicated Brand Role
As companies grow larger, they build dedicated brand teams that tackle perception problems, spend ad dollars to use brand marketing to drive long term growth, and adjust company level positioning over time. Product marketers are used to driving positioning of individual features of products, and with that already have a good understanding of overall company positioning. This may or may not be an option depending on the specific needs of the company at the time. Usually, the larger the company, the more likely this opportunity exists.


The future of the product marketing role is fraught with uncertainty. In B2B companies, the role is definitely better established and positioned for success, but I think it’s only a matter of time before those roles face the same challenges consumer product marketers face today around specialization and new team structures that gradually phase this role out. If you are in product marketing, don’t panic. Just think strategically about how to position yourself for one of the three above options to maintain career growth.

The Analyst Career Path

I’ve written before about analytics teams as a crucial function in today’s technology companies. Technology companies are rapidly hiring analyst roles to pair with their product teams. And while my previous post discussed how to hire analysts and structure their teams within organizations, I haven’t written about how analysts should approach their careers.

Many technology roles, at startups in particular, have an issue with career progression. While established industries have defined career ladders, the path of career advancement is much less clear in many technology roles. Engineering, being the largest and oldest function in technology companies, now has a well defined individual contributor and manager career path all the way up to VP Engineering and CTO. Product Managers know they can progress to manager roles at their companies all the way to VP Product, and if they want to remain and individual contributor, they can still grow by working on more and more complex and strategic products over time. As I’ve talked to many analysts and analytics teams, this progression is not as well defined. I will outline how I think about this progression as someone who has been an analyst and managed analysts.

Option 1: Graduate into Data Science

If someone wants to remain an individual contributor and not manage, at some point the only way to become a better analyst is to graduate into a data science role. Now, there is some confusion with where the line is between analyst and data scientist, and many companies just call all of their analysts data science as a form of title inflation. I define the role of an analyst as someone who uses data to help identify and communicate business opportunities, and drive decisions for teams. This includes targeted analysis driven by others as well as free form analysis driven the analyst. From a process perspective, this includes everything from making recommendations, helping with experimentation, and creating dashboards to help others make decisions. From a tooling perspective, this means everything from writing SQL queries, identifying logging opportunities for product engineering and database design opportunities with data engineering, creating new dashboards and visualizations. An analyst retrieves, analyzes, and recommends, and is judged by not only how good those recommendations are, but how often they are followed.

So, how does data science differ? A data scientist writes code beyond SQL to manipulate data for analysis and potentially for product experience. A data scientist can write an algorithm that powers a personalized experience in the product, or just do more complicated analyses requiring more sophisticated querying using Python, R, etc. Data scientists jump in when analyses are too complicated to be handled by analysts, and also frequently partner or embed with product and engineering teams to change the product. This is more than just a higher-power analyst role though. Data scientists have deep expertise in certain areas, like machine learning, statistical inference, and focus on solving specific, hard problems over longer time horizons.

Option 2: Become an Analytics Manager
If you wish to get on a management track, becoming an analytics manager is the natural path. Since analysts are being hired so frequently, they need managers who can mentor and coordinate learnings between teams. While analysts are best embedded, analytics management bears the important responsibility of solving company-wide analytics issues related to tooling, process, etc.

Option 3: Graduate into Product Management
The third path that analysts can choose to grow their career is migrate into product management. Technically, product managers and analysts are peers in cross-functional teams, but product management has better career pathing that doesn’t require as much technical investment as data science, and product managers tend to have a bit more power in organizations today.

The migration of analysts to product manager is increasingly common as more and more product teams rely on data as the foundation for most decision-making. This has certainly been most true on growth teams and teams that utilize personalization, but I believe all future product teams are data savvy. A significant percentage of product managers at Pinterest started as analysts at the company. This same migration is also true for marketing analysts. They tend to become quantitative marketers over time, or switch to product analytics.


Being successful as an analyst is peculiar is that it almost requires a switch in roles over the time in ways that are not true for design, engineering, and many other roles in technology companies. Fortunately, the analyst has a lot of choices on how to progress within an organization. Hopefully, managers of analysts get better at outlining these different opportunities and help analysts position themselves toward the best ones for them over time.

Thanks to George Xing for reading early drafts of this.

Currently listening to Compro by Skee Mask.

Product Visionary vs. Product Leader

Many people want to work in product management. One of the most common questions I receive is how to break into product management. It’s a hard question for me to answer, because 1) there is no default path (the same is true for trying to land a business development role), and 2) most of these people really don’t know what they’re asking for. My most common response is, “Are you sure? Product management can kind of suck.” The reason for the dichotomy of people who haven’t done product management finding it so alluring, and people who have done it cautioning people trying to get in is the difference between what I call a product visionary and the product leader.

Product visionaries are who we all hear about in the press. They are the people who come up with brilliant products that go viral or solve real needs in the market that no one else thought of. They appear to be masters of finding product/market fit. I’ve been lucky enough to work with a few of them in my previous jobs and a few in the portfolio at Greylock. These tend to be founder/CEOs, and they generate brilliant insights that create product opportunities others don’t see. Ev Williams is on his third breakout product in Medium after Blogger and Twitter. Ben Rubin created two products that hit product/market fit in two years with Meerkat and now Houseparty.

Anyone working in technology hears these stories, and they think the shortest path to that sort of glory is becoming a product manager. They are excited to get to a role where they can drive the vision of a product, even if it’s only one part of the company. This excitement is exacerbated by the commonly propagated myth that the product manager is the mini-CEO of their product. The reality is that in 90+% of cases, product management is not about being a visionary. It’s about being a leader.

What does a product leader do at a tech company? It’s actually very little of creating a vision and a strategy from scratch. It’s about helping everyone understand what the vision and strategy is. It’s about communicating to the entire team why the company is doing what it is doing. It’s about building a process that helps a team execute on that vision. It’s about when there are competing visions, aligning and motivating the team to focus on one, and getting people to disagree and commit (including sometimes yourself). It’s about looking at data to measure if product changes are having a positive impact on the customer and the company’s growth. It’s about talking to users to understand why they’re doing what they’re doing, and the problems they still face even though your product exists. It’s about mentoring more junior people on your team, across product as well as engineering, design, and analytics. And they don’t have to listen to you, so you have to use influence rather than authority to be successful.

In the scaling phase of a startup, it’s product leadership that drives performance, not vision. Vision is needed early to find product/market fit and plot a course to scale, and then the less that vision wavers over time the better. This vision is usually done by the founder/CEO. The reason founders hire product managers and VPs of Product is not to set vision, but to help execute the vision. Don’t get me wrong; that will sometimes mean coming up with solutions to problems your customers face. If a company is scaling by having the founders solve all the customers’ problems instead of product teams, it will struggle. But much of the time, it will be wrangling the ideas of the individual engineers, designers, and analysts on your team and matching that to an overall vision set by the founder(s). It’s very rarely your ideas you’re executing on as a product leader, and it shouldn’t be.

I also don’t want to make it sounds like I am devaluing visionaries. They are, of course, critical in finding the initial idea(s) that create a growing company and maintaining a vision for that growing company. Having visionaries also becomes more important as you saturate your core market and need to tackle new value propositions to drive new growth opportunities. That is the ideal time for non-founder visionaries to enter a growing company. These are not going to be typical product managers or VP’s though. They are usually ex-founders. The best outcomes for these people entering an organization that is scaling is giving them a team and space to experiment with ideas until they find their own product/market fit, where a business unit is built out around that vision with product leaders to help them scale.

As you’re thinking about your business, think about whether you need a product visionary or a product leader. Most founder/CEOs are already visionaries, so they need a product leader to help execute. Some businesses minded founders need the opposite to be successful. If you’re thinking about product management, think about whether what you really want to be a is product visionary instead of a product leader. In that case, it might be a better idea to start a company than take a role expecting to execute on your vision and instead managing other people’s visions.

Currently listening to Ambivert Tools Vol. 3 by Lone.

How to Get a Job at a Technology Company After an MBA

Having been working in technology and startups for a decade and completing an MBA in the process, a frequent question I receive is how can an MBA graduate transfer into the technology industry post-graduation, and many times specifically, into a startup. This question has broken my rule of four: once a question has been asked of me four times, I write a blog post answering it for the masses. This post outlines my advice to those people.

Let’s Say the Hard Thing First: Most Startups Don’t Want You
The thing you have to understand about startups is that they are about belief. A (usually first time) founder with (usually) not much of an understanding of an industry decides s/he can take it on and make it better. If someones has that type of belief in him/herself, that person also believes they can learn all of the skills necessary to execute on their vision, but they don’t have any of those skills when they start. If things happen to go well, the founder/s quickly realize they do have some skills they can’t or don’t have the time to learn that are necessary to scale the business. So, what they look for in people they bring onto their teams is someone with a skill set that can fill a weakness of theirs or their teams. This usually means previous experience in startups as the challenges are so unique.

Most MBAs do not have any startup experience, and founders won’t be impressed if you won your business plan competition during school. They probably never wrote one anyway. If you don’t have a skill they need right now, they feel like they are wasting their time talking to you. In fact, the more likely a startup founder is to talk to you, the less likely it is going to be a successful startup.

Most startups also pay below market values, and MBAs tend to have salary requirements to help them pay down their debt. I remember interviewing MBAs for a position that would report to me. Almost all of them asked for more money in salary than I was making. Essentially, what happens is they don’t want your salary, and they don’t yet need your strategic skills. They need executional skills you probably don’t have.

The Baby Step: Start at an Established Tech Company
Most MBA are deep in debt, and they want to go head on in a new direction. Some times, that may work. But my advice for people wanting to get into startups is to take a baby step. Instead of targeting companies with 15-50 people, target established tech companies. The main reason for this is to build up the set of skills startups needs. Where can you learn those skills? From people that previously worked in startups. Many of those people are still working for what was a startup and is now a successful tech company. The bonus of this situation is that since these companies are bigger, they are more likely to value MBA skills and more likely to have training programs to help you learn the skills startups need. So, if you work at a, say, LinkedIn, for two years, you probably learn a thing or two that scales down to a startup. The other great thing about established tech companies is they are likely to offer internships for MBAs, which are critically important during the summer time off.

What to Do at an Established Tech Company
The next question becomes what to work on at an established tech company. This is a trade off between how much of your skills translate to what they need, and what you want to learn. Let’s say you were in finance before your MBA, and you want to get into marketing. Perhaps an FP&A position that focuses on marketing spend would be an ideal option as it gives you exposure into all the marketing data and probably a lot of the marketers you want to learn from. Perhaps there is a marketing position available that they can train you in at the start. That is ideal. If not, you may be able to transfer later as you learn the lingo.

The Bottom Line
Changing industries is a long term play. You can’t expect to just hop into a new industry with no expertise and get your ideal role at your ideal company. If that role is a role at a startup, play the long game by building skills at a larger company first and working with the right people to make sure that can translate a few years down the line.

Skill Optionality for Career Growth

Most firms operate via division of labor and specialization. So, as a budding employee at most companies, the task is to figure out what to specialize in so you have a place in the organization. This task is valuable in that in ensues a role for you in the organization and allows you to become a subject matter expert over time in a specific field. The world needs subject matter experts, so picking the right specialty early on is an important decision.

Specializing Too Early

The problem with that decision is when most employees are forced to make that decision i.e. in one of their first few jobs or during college when picking a major, they really have no idea what a great specialty will be, either from a matching their personality perspective or being needed in the marketplace perspective. Furthermore, universities are literally the least knowledgeable about what specialties will be valuable in the market because they largely exist outside of the labor market. This is why we’re pumping out hundreds of thousands of journalism majors even though there are very few jobs in journalism above the poverty line.

Making the Bet

Andy Johns has a great post on identifying individual strengths and making bets on skills that will become more valuable over time in the labor market. I would encourage anyone thinking about how to position their career to read it. The challenge is in making the right bets, and how bets can scale long-term for a career. For example, let’s say you make a bet to focus on social media marketing. Is that skill likely to be more or less valuable in four years? Now, the answer to this question has two components: 1) how many more firms will want these skills in the future and 2) how many more people will have these skills in the future. If the answer to 1) is a lot more and the answer to 2) is not much more, that’s a gold mine, but if the answer to both is a lot more, it may not be that great of a bet.

Scaling the Bet

The second component is how that bet scales. To answer this question, you need to know far can that skill can scale upward in an organization or in a career with that specialization. Sticking with the social media example, will there be Directors of Social Media Marketing in the future? VP’s? Chief Social Officers? If that seems likely, that’s another reason to focus on that niche. Unfortunately, no matter what specialty someone looks at, the answer is almost always that there is a cap to how far that specialty goes before one needs to acquire more skills to advance further. Sticking with social media, that track may end at Social Media Manager, and then you need to have PR skills to advance to the next phase at most organizations, or more online marketing skills like SEM, SEO, and email marketing. After that, whichever track you choose, you would need to fill in those other skills to become a VP of Marketing or a CMO.

This scenario becomes a problem for many people, as there are no convenient ways to develop new specialties over time. If you are working on social media all day, chances are low that your manager will proactively make sure you develop PR or SEM skills to prepare you to advance. So, people get stuck with the specialties and levels they are at after a while, and if those specialties become less important, they become less important over time. In a field like marketing, the skills needed at companies change very dramatically, as new marketing channels emerge over time, and as marketing channels mature, they tend to be less effective. Going back to school doesn’t help, as they tend to teach less skill-based functions, and certificates are mostly seen as a joke by employers.

Going T-Shaped

Fortunately, there are some ways to dodge these main issues, which are 1) not being able to predict the future on which skills are best to specialize in because the market moves too fast, and 2) not being able to add new skills over time to successfully manage more disciplines over time. Most advocate a position called being t-shaped ( good example here and example for search marketers here). The t-shaped model is great, but it misses some key features for career development I want to highlight.

1) One big bet vs. a few small bets

Becoming a t-shaped employee still requires placing a big bet on one area of depth and an 80/20 approach to close disciplines around that area of depth. There is still a large risk if that area of depth devolves in importance over time. The T-shape implies a static field and demand of skills that does not represent the labor market.

2) Individual contributor vs. manager

Management (and especially upper management) positions are not t-shaped. They are largely about strategy and goals. Having a ton of depth in a field like social media for a VP of Marketing is not especially useful as that person is expected to have someone that reports to him/her that has more depth. A senior manager needs to be able to spot opportunities to meet goals, and manage a diverse group of people to work together to reach those goals. Currently, many managers have a jarring experience where they begin to manage multiple disciplines and people not related to the depth that got them promoted.

3) Different T shapes work better at different companies

Sticking with the marketing examples, going deep in social media might be great for one company, but not very effective for others. Only knowing a little about other areas will likely make you not a great fit if social doesn’t move the needle. Ideally, you want your skills to work on a broad array of companies (though not too broad, like tech and industrial).

Solving the Problem

So how do you de-risk the choosing of a specialty and position yourself for more senior positions over time? That solution is to embrace skill optionality. What is skill optionality? It is maintaining exposure to different (especially emerging) areas of a field, and focusing, when necessary on specific niches, but not being stuck on one skill forever. Think of that t-shaped framework as a moving model where the component that is the stem of the T is gradually moving around as opportunities emerge in different fields and sharing depth with one or more other fields. So, instead of one long stem on SEO as in the Moz example above, it becomes a pi as SEO shares time with social media.

Skill optionality solves many problems for young or even experienced professionals. Young professionals gain exposure to many different fields, and are more likely to find one they excel at to either specialize in for the long-term or use as an initial depth from which to expand. For those with more experience, it breaks through the career ceiling of being just a subject matter expert, and protects one when certain expertises become less valuable. If you become experienced in four or five things, it is unlikely all five will become less important over time. Typically, as one skill becomes less important, another becomes more important. Skill optionality protects you from movements in the market related to skill needs.

I am not describing being a generalist, but just diversifying your portfolio of skills a little bit. I’ve seen a lot of blog posts that say every marketer in the future should know how to code, and use Photoshop, and know how to execute a laundry list of different marketing tactics. Chances are that’s too much for most people. How do you know if you’re going too general? Well, you should feel like the smartest person in the room on multiple subjects. If you’re a manager, it should that you or someone on your team is, and, if the latter, that you’re the next smartest after your team member. If you can’t claim a few broad areas as your domain, you’ve probably gone too far. In marketing, most companies win because they focus on a few channels, and become the best in the world at them. Skill optionality is not about executing in 30 areas, but knowing and adapting to which few maximally benefit your company/career, and being positioned to strategize as well as execute on those.

How to Execute

The next question you should be asking is how to execute this. I would like to make sure people understand that corporate America is not built for skill optionality; it is built for specialization. So, optimizing for this career path is fighting against the corporate ladder in every way early on in a career, but with maximum upside later on in a career. Some good strategies for young professionals is to shoot for positions that provide exposure to different areas in useful ways, like a web analyst who measures online marketing performance and therefore begins to understand different elements of online marketing. If that is not possible, another good strategy is to develop a specialty at a large company, and then move to a much smaller one where that skill is needed, but there is plenty of opportunity to develop new skills as no one else will be doing other things close to that specialty (or other things in the T one wants to develop). Some larger companies have rotational programs, which sound like a great way to get exposure to multiple areas, though, without having experienced these myself, I can’t say for sure.

The bottom line is that it’s important to pay attention to new opportunities to go broader in your skill set, and fight to get exposure to those opportunities. This will de-risk specialties that go out of favor in the market as well as better position you for management in the future. Even if you never want to manage, having multiple skill sets that you can adjust your depth on ensures you are always a viable candidate for many open positions, and will make you suitable for positions some companies desperately need.

Note: My examples are in marketing because that’s where I can get most concrete, but these examples can easily apply to engineers (via languages and elements of the stack), designers (with web, mobile, print, interactive, copy, coding, ui, ux), or just about any other discipline I can think of.