A lot of great designers think that the only way to move up in their career is to give up their individual contributor status and transition into management. Other designers may make great managers, but are hesitant to make the transition of how they perceive the practice or don’t feel ready yet. The management track is often conveyed as a paved road you must take with no turning back. In reality, it’s an odyssey from designer to leader of people.
Throughout my career, I’ve made the switch from design leader to individual contributor based on the company I was at and the impact I wanted to make. After I left Black Pixel, I joined One Medical as a Product Design lead with no managerial responsibilities. During year two of my tenure at One Medical, there was a management need and I happily took the mantle again.
The goal of this article is to help you decide if design management is the right choice for you, and if it is, to help you start that journey. It will cover:
- The qualities that make a great manager
- The skills you will need to hone to develop those qualities
- Rebuttals to widely-believed myths about the transition from designer to manager
Afterward, I will provide you with key frameworks and reflection questions to help you decide if a design management career is right for you and if so, how to set yourself up for success.
Design manager as strategist, operator, and coach
The first thing to understand is that there’s no one formula for leadership . It’ll vary based on the company you work on, its scale, and situational aspects of what your team needs.
That said, being a designer manager boils down to three core areas:
- Leading design as a strategist
- Ensuring your team runs well and is happy as an operator
- Growing your team members as a coach
As a strategist, your chief concern is whether or not the team is meeting business goals. The main priority should be understanding customer problems end-to-end and researching new opportunities to create an inspiring design vision.
As designers, it is important to connect all of the work we do as a team to key business outcomes. In your role as strategist you will be responsible for developing and tracking Objectives and Key Results (OKRs) for your team. This can get a little tricky due to the nature of design work being dependent on the work OKRs of other teams.
More often than not, design team OKRs will be more lateral than vertical. Design is not only a practice, but a capability that can be a force multiplier for outcomes for the customer and company.
This could show up in many ways. For example, brand design helping marketing increase signups due to awareness campaigns that drive traffic to the site, or product design improving a feature customers have been asking for, keeping them retained as a happy customer.
In your capacity as “operator”, you’re responsible for the team running effectively. This is the most traditional aspect of management, stemming from production line managers overseeing the work. The operator’s role is to implement effective processes to build team culture and engagement, recruit and hire quality designers, and manage team performance.
The operator is responsible for setting the design cadence and the pace and frequency of feedback. One of the most important processes to engineer is the design critique (Noah Levin, Director of Product Design at Figma has a great article about how to run great critiques), and ensuring that it is a good fit for how the team operates.
A happy team is an effective team. As managers, you’re also responsible for the team’s well-being and create the most safe and positive environment possible.
You’re not going to be able to make everyone happy and will need to balance the needs of each individual as the collective team with what needs to get done at the company level. They’ll need to know when to make the call if a team member needs a break due to burnout or when things need to slow down. An offsite that recharges someone could be the reason they decide to stay when facing burnout.
Lastly, as a coach you’re responsible for providing growth and development opportunities to team members. This can be done through providing funding for workshops and classes or through coaching team members yourself.
The 1:1 is a manager’s secret weapon and the most important meeting you’ll have with their team members. It’s a way to build relationships and ensure your team members are happy, check on what barriers you can remove, and discuss career development.
During my first 1:1 with a direct report, I ask them where they want to go professionally, not only in their current role but over the course of their entire career. My belief is you want designers to thrive in their career, beyond their tenure with you and exceeding you in every way. If there is no career ladder, that is something to put in place immediately and continue to refine. From the first 1:1 together to the last, coaching is a daily activity.
Finding the Right Balance
One of the chief challenges of being a design manager is fluidly moving between these three roles. A manager's responsibilities will change based on what the company needs at that moment.
For instance, if a company’s goals are well-defined and growth is one of them then a manager may find themselves in the operator facet more than the other two.Then when company growth stabilizes and it is time to define new goals, the manager will move into the strategist facet.
The trick is to balance these three responsibilities as they fluctuate as the company grows and evolves. For example, in my career I’ve had various design leadership levels based on specific needs:
- As a Design Director at Black Pixel, the majority of our work was client services. I was very involved as a strategist and doing the work while I mentored other designers
- My time at One Medical was growing the Product Design team in its scaling stage. As I led in strategy, I hired more designers and increased more of my time operating the team and being a coach
- At Webflow, I don’t even edit Figma files, and the majority of my time is operating the team and working with the management team
“Management is a point of no return”
(and other myths about becoming a design manager)
A great manager needs to be a strategist, an operator, and a coach, but what does a great manager not need to be?
There are some widespread misconceptions about what it means to be a design manager. I am going to cover the five myths that I believe are the most problematic.
Myth #1: Becoming a design manager is a point of no return
One very common myth is that once you become a manager, you can’t go back to an IC. This is untrue and can be counterproductive.
Management in tech is littered with people in the role who didn’t receive enough training and support or felt forced to step into the role. I have switched between being a manager and IC throughout my career. It might feel like an ego hit at first when you go from a manager to an IC, but it should not.
Myth #2: Design management is only about supporting people.
While the best managers go into management because they care deeply about people, supporting others is just the tip of the iceberg. Design management is also operations, administration, and accountability. Coaching is not the only aspect of the job.
Myth #3: You need to become a design manager to move up in your career
This might be true for some companies — but not all.
In fact, the industry is evolving separate parallel career paths for both managers and individual contributors. Many companies have ways for designers to remain individual contributors as they level up, while also being able to receive compensation and exercise influence on the same level as a senior manager.
For instance, at Webflow, the Principal Designer role is leveled the same as a Senior Manager role and allows for a similar compensation and similar level of influence within the company. Leadership and management, while often tied together, are not mutually exclusive.
So in deciding which path to choose, ask yourself:
- Where would you like to have the most impact?
- Do you want to contribute to specific projects or do you want to have an impact at the company level?
- What gives you the most gratitude?
Myth #4: Design managers are the best designers on their team
Not only is it not true that designer managers must be the best designers on the team — they also shouldn’t be.
While there is a certain level of skill and comprehension that you should have as a design manager to lead your team, the goal is to make every designer on your team their best — not to be better than them at what they do.
Some of the best coaches in NBA history, for example, were not hall-of-fame players; but they were knowledgeable, they knew how to motivate talent, and they had enough experience to lead.
Similarly, while you will need to draw from your core skill set as a designer in order to evaluate and critique your employees’ work, that doesn’t mean you need to be the best designer on the team.
Myth #5: Design managers don't care about design anymore
While it may be true that you are pushing pixels less as a design manager, you are ultimately accountable for everything that your group creates.
Part of the job of being a design manager is coaching employees on their designs and helping them improve as designers. Your framework for approaching and executing designs will serve as a model for your employees.
Here’s what Cara, an Coho Design Fellow, had to say about her career path after having gone through the Coho Design fellowship: “
Skills that carry over from design & new skills to build
Becoming a design manager does not mean starting over from scratch. Even though you will be making fewer individual contributions to design work, the skills you have honed during your time as a designer will serve you as a manager. Examples include:
- Foundational design skills: The foundational skills of research, empathy, experimenting, gathering feedback, and iterating also apply to managing a team
- Empathy and active listening: This skill set becomes particularly important when it comes time to coach your team during 1:1s as a coach, and also in helping you understand customer needs as a strategist
- Iteration and experimentation: These are key to developing a good design workflow. Even the most successful managers will not get everything right on their first try; iteration is essential to incrementally improve your management processes
- Storytelling: Storytelling humanizes the personas we design for, building empathy and perspective in a human-centric way. Powerful stories are essential to keeping your team motivated and inspired.
- System design: Your work with leaders on org design as a manager will be similar to the way you’d work with an engineer on architecting large-scale,complex systems in the past as a designer
But while you can certainly utilize many of the skills that you have developed as a designer, you will also have to build new management skills to succeed as a manager. For example:
- Leadership communication: As a manager, you’re balancing downstream communication with your direct reports, cross-functional communication with other peer managers, and upstream with execs and stakeholders. This requires different modes and strategies of communication that you may not have experienced as an individual contributor
- Coaching and developing people: My belief is you want designers to thrive in their career, beyond their tenure with you and exceeding you in every way. If there is no career ladder, that is something to put in place immediately and continue to refine. From the first 1:1 together to the last, coaching is a daily activity.
- Delegation and expectation setting: As an individual contributor, it’s likely you don’t have much of an option to delegate work to others. As a manager, it’s your primary objective to hand off responsibilities for your team and set clear expectations for them to own.
- Assessing talent and hiring: Though you may have been involved with interviewing as a designer, understanding the scope of being a hiring manager, attracting talent, and striving to build diverse teams is a new endeavor as you step into management
- Autonomy: Taking initiative by managing or creating your own projects that address core needs of your business. Managers need to be able to identify these opportunities based on customer feedback or strategic directions.
Is design management right for you?
The truth is that while design management can be a fulfilling career path, not everybody will be happy in the role.
This is okay. Management should not be the only way to advance in your career, and individual contributors have a path forward as well. Later on I will talk about strategies for advancing your design career in different ways, but in the meantime I invite you to take some time to reflect on whether design management is the right choice for you.
Before you read my take on the following questions, reflect and answer each one for yourself. Jot down your answers or type them into a document and refer to them as you go through the rest of this article.
- What areas of design management do I care about most, and what gives me the most energy?
- What part of my work makes me the happiest? What parts do I care less about?
- Who are my mentors and what can I learn from them?
- How involved do I want to be in the design work? Would I be okay with designing not my primary focus or would I miss it?
Ok, have you thought about and answered these questions for yourself? When you are ready, read on to learn more about which career path, whether in design or design management, is right for you.
- Do you like generating ideas and executing a design for a particular project or do you like to have input across projects to ensure consistent vision and quality? If you are happiest in the weeds plugging away at a particular design project, continuing the IC path might be the most gratifying for you. If you enjoy setting strategic directions, contributing across projects, and supporting others in their work then you may be suited to design management. Play to your strengths. Your role as a design manager is to ensure everything in your scope of responsibility is done well, not that you personally have to be good at things. Playing to your strengths and leveraging the strengths of others will yield the best outcomes.
- Do you have a design manager at your company that you are comfortable talking about career advancement? What can you learn from their career progression to apply to your own? A lack of mentorship does not mean that you are not cut out for design management, but it may mean that it is more difficult to get on the management track..perhaps at your current company. If you do not have a mentor you can draw from and bounce ideas off of, do you have the bandwidth and desire to put in the extra work required to make your case for design manager?
- Do you enjoy sitting with executives all day and debating and arguing about resourcing and never be attuned to what your team is doing? Or, do you want to be closer to the work sitting side-by-side with the people I am managing? Your answer to this question will help you map out and define your design management role (or even signal that you might want to advance as an individual contributor). For instance, if you prefer to be closer to the design work you may want to manage a smaller team whereas if you want to be closer to department-wide operations you may want to be sitting with those executives.
Although this article details what a design manager is and how to become one, as mentioned above in myth # 3, keep in mind that becoming a design manager is not the only way for you to advance your career as a designer.
In the next section I’ll help you develop a game plan for advancing your career, whether as an individual contributor, or in pursuing a design manager role.
Building your career roadmap
This section covers your potential as a manager, the case for management in your current role (or beyond), and how to build your portfolio.
Would I be a good fit for management?
Like many things in life, there is no way to know you’d be a good fit for something until you try it. However, in my experience there are certain attributes and behaviors that demonstrate manager potential:
- Keith Rabois, one of the most renowned operators in tech, talks about looking at who people come to for help in the office as a good heuristic for management material. When people seek you out to help unblock and help them, that’s a great sign as a manager
- The time you spend coaching and training other designers delivers more value than you contributing to the work yourself
- People are vulnerable around you because they know you care and feel safe.
How to make your case for a design management position
The number one mistake people make in their efforts to become design manager is not letting their organization leaders know that they’re interested in the role.
That said, leaders’ abilities to offer you a design manager role will be contingent on if management opportunities are available. For instance, if the team only has three designers there may not be a value add from a design manager for that team.
However, even if something like this is the case, maybe there is a larger team at your organization or a team that is positioned for growth? To make your case for design manager, you will need to identify these opportunities within the company or look for opportunities outside your company if none exist within.
What to consider when talking to organization leadership about your management interest:
- What motivates you as a manager?
- Why would you make a bigger impact as a people manager vs. an individual contributor?
Remember that you’re in the driver seat of your career path. Build your own career development plan in addition (or in absence) of what your manager gives you.
How to create a design management portfolio
One question I often get is, “What does a design manager’s portfolio look like?”
In reality, the answer is “not much different than an IC portfolio”.
- Both provide case studies of the impact you’ve made.
- As a manager, your team and organizational impact are the results you share instead.
- Since you’re not showing pixels you’ve designed, the key is articulating how you understood the problem, company goals, and provide clarity for your team to achieve their goals.
When a hiring manager is reviewing your management portfolio, they should have a sense of how you lead humans, your business acumen, and the systems you put in place to ensure high quality work is done.
How to level up as an individual contributor
Through the earlier reflective exercise, you may have discovered that management is not for you, and that is okay.
Here are some steps that you can take to advance in your career as an individual contributor.
Step 1: Enhance Your Portfolio
Garnering recognition and earning coveted raises is dependent in large part on how you sell yourself. Tuning your portfolio is a great way to set yourself up for a conversation with your supervisor about a potential raise or promotion within your design team.
As you continue to progress in your career as an individual contributor, the focus will be on mastery and impact at the company level. Your portfolio should reflect the depth you have in a particular area and be framed on the impact and influence you have on projects at a higher level.
Step 2: Create Opportunities for Recognition
Perhaps you can do exemplary work, but you may still fly under the radar if you are having trouble getting your work out there and recognized throughout your company. Here are some concrete strategies that you can use to help broaden your reach and communicate your contributions to your team and beyond.
- Set up demos to make your work visible that your team and stakeholders can attend. This can be as simple as recording a Loom of how you’re thinking of work. You’d be surprised how viral these can go to broaden recognition
- Create tools and resources to help your peer designers do better work
- Finally, the best way is being recognized for your impact through peer feedback. When your fellow designers give you praise for your leadership and you have that trust, that’s the best evidence for your candidacy for management
Step 3: Talk to your manager about advancement opportunities
Talking to your manager is an important step in increasing the recognition you receive for your role as well as for getting opportunities to do fun, interesting, and challenging projects.
Through my own experiences I have developed a framework for navigating these conversations by asking myself the following questions in advance:
- What is my superpower should I double down on?
- Are there stretch opportunities for me to grow new skills with close guidance/mentorship? (ex: hiring, etc.)
- Where can I be a fly on the wall and learn through observation of leaders in action?
The management growth track
Design management is galvanizing humans towards a shared mission while developing their professional and personal growth. You will make a great design manager if you enjoy focusing on the progression and growth of other people. I discovered that this is one of the greatest joys that I get from management.
If you find that—like me—you enjoy management, you can look towards career advancement opportunities at senior manager, director, and finally executive level (VP or C-Suite). You might find yourself expanding in other areas of responsibility laterally. As some design leaders grow, they might take lateral responsibilities and lead product as well. Design management can lead to more expansive opportunities.
There is no set single pathway from designer to manager, and that’s exciting. Remember that ultimately you’re in the driver seat of your career journey. What I have outlined here is based on my own experiences with the transition, but it is by no means exhaustive or linear. Talking with your manager or another mentor at your current firm is a great way to understand how you can chart your own path from designer to manager or how you can advance as an individual contributor.
If you’re looking to diver deeper into Design Management, consider applying to the Coho Design fellowship to learn, connect, and level up with the best designers in tech.
“But the eyes are blind. One must look with the heart.”
ANTOINE DE SAINT-EXUPÉRY
Set Your Course Before You Set Off
So just what is the first step in the modern job search?
Well, you could jump into action mode and do what we’ve all been trained to do: Work on your resume. Or you could fiddle around with your LinkedIn profile. Or perhaps the most mindless (and least impactful) activity: taking that stale, multipurpose resume and applying cold to every job you come across. With so many ways to browse and apply—with so many things to do—it’s no wonder that lots of searches never leave the launchpad.
But here’s the truth: All those actions won’t yield results unless they’re focused. While firing off your resume far and wide like a bazooka or clicking every “Easy Apply” button you see on LinkedIn may feel productive, it’s not. It takes a laser-guided missile to hit your target (which might be new connections, emails from a recruiter, interview callbacks, and ultimately job offers). Your first task is to get to know thyself—then find what matches are out there and get discovered for them.
So here’s a simple operating question to cut through all the analysis paralysis: What kind of job would you actually love in the first place?
If you don’t yet know the answer to that question, that’s okay. It takes time for lots of us. But until you start to develop a hypothesis about the kind of work that brings you fulfillment, every other step— building a resume, crafting a LinkedIn profile, even networking— could feel like a step through superglue. Without a clear North Star to guide you, every job search maneuver is just a shot in the dark. That’s where the Exploring step comes in.
This is an absolutely critical, soul-baring, be-truly-real-with- yourself, no-shortcuts-allowed exercise. Because when it comes to your professional brand in the digital world, getting focused— on what you really want to do next, and then on how you position yourself accordingly—is the key.
Said another way: There’s no such thing as a perfect LinkedIn profile. There is only a perfect LinkedIn profile for a specific job. What is that job for you, and for where you are right now in your career? Clarifying this will be your compass.
So to make sure you set off in the proper direction, let’s take the first step together: finding the right path for you by exploring on LinkedIn. Let’s do it in two parts: 1) understanding your options, and 2) testing your options.
Career coach Shelley Piedmont says:
“Take the first step of learning about other career options. That is the hardest one. All steps after that come much easier.”
Part 1: Understand Your Options
To point your compass toward the right career path, you need to get a feel for what’s out there. Once you do, chances are you won’t have to blaze an entirely new trail. The galaxy of possibilities will be made more knowable and more manageable.
Here’s a useful case study. Jeremy used to mentor a high school student in the South Bronx named Ian. Ian had impressive clarity about his future and was dead set on becoming a criminal forensic scientist. There was only one problem: Ian hated science. Kind of a job requirement. Oops.
Upon further investigation, it turned out that Ian didn’t know any practitioners in the field. But he did watch a ton of CSI. Sure enough, he had trained his sights on the one profession that seemed cool—even though it was totally wrong for him!
Ian is no outlier. We have all done this, usually at earlier stages of our professional lives, but it’s liable to happen at other key moments of our careers, like mulling over what comes next after a graduate program, or trying to break into a new industry mid-career. We get tunnel vision on a specific path that we’ve heard about—and then start to ignore all other possibilities. And we do so at our own peril, given that just seeing a role on TV or focusing on what our friends are passionate about may block out the other careers that are indeed a better fit for us.
To avoid this trap, you must get intimately acquainted with the set of real possibilities out there. The single best way to do that is to explore the trails that others have blazed before you. Especially those with whom you already have shared work credentials or a shared affiliation—like an alma mater—who are lower-hanging fruit to connect with.
Explore the trails that others have blazed before you.
When we worked at LinkedIn, our team built a handy product called the Alumni Tool. (Sure, we’re biased, but we think it’s the best-kept secret on LinkedIn.) And even though it’s buried deep within the site, discovering it is like striking career gold: It shows the paths of every alum at virtually every school—colleges, universities, graduate programs, even many high schools—in the world.
So what makes these paths so valuable to you? And why the school-based approach to career exploration? The Alumni Tool gives you a sense of your most realistic, attainable options. After all, these alumni have been in your shoes, studied what you’ve studied, and gone on to land awesome opportunities across a variety of fields, locations, and employers. Not only that: Given your shared affiliation (Go Tigers/Aggies/Banana Slugs/Fill-In-Your-Goofy-Mascot- Here!), these contacts are also low-hanging potential referrals and informational interviewers. Their brains—and networks—are ripe for the picking.
Here’s how to start mining that alma mater career path on LinkedIn:
1. Type in your school in the search box, and choose the “School” page option.
2. Click “Alumni” at the top of the college or university’s page.
3. Welcome to the best-kept secret on LinkedIn! You now have access to all your school’s alumni on the site (i.e., those who’ve listed the school in the Education section of their profiles—all easily filterable by location, company, job, major, and connection proximity):
What to do next with this information depends on where you are in your career (e.g., a new or soon-to-be grad casting a wide net, or twenty years out with more focused requirements) and on what’s most important to your search (e.g., living in a certain geographical area, or working for a dream employer).
Here are just a few examples of the myriad ways you can purposely slice and dice this alumni data to get precisely what—and whom—you need to help you focus your job search.
GEOGRAPHIC FILTERING
Let’s say you’re a current college senior at Texas A&M University who wants to move to Austin after graduation. Select “Austin, Texas Area” from the Where they live column (if it doesn’t appear in the first set of listings, click “Add,” then search for your desired location). You have just cut down your list of 370,000+ alumni to one-tenth of that unruly number—only the 31,000+ in Austin:
And best of all, everything else in the Alumni Tool dynamically updates based on any filters you apply. So in this example, you’ll now see only the companies hiring alums in the Austin area in the Where they work column:
Okay, so what? Well, now you have a list of alumni in your desired city who are available to connect and from whom you can learn. (We’ll get into that reaching out part later in this chapter.) Just as valuable, this is also your postgraduation employer lead list. Both factors can help you get focused. It’s a custom-tailored directory of potential organizations to explore—ones in which your alumni base is already working.
ACADEMIC FILTERING
Maybe you’re a new grad who’s not sure what to do with your psych degree. You’re far from alone—it turns out that, according to LinkedIn, more than a thousand Texas A&M alumni in Austin walked in your shoes and navigated that very situation. Just click the “Next” button to toggle over to the What they studied column and choose your major:
Now look at the Where they work column and behold all the most popular options at your disposal—from technology and business to academia:
OCCUPATIONAL FILTERING
Let’s say you graduated a decade ago and entered the health care sector but now want to switch into an information technology career. Choose your desired field (and perhaps also the function you want to be in) from the What they do column:
Again, notice that the other elements of this tool also update as you click into these filters. So toggle back and check out the various employers where others like you have landed jobs:
OTHER BEST PRACTICES
Here are a few more important notes to get the most value out of the Alumni Tool:
1. Be sure to conduct a similar search for every school you attended, in any capacity (including high schools, graduate programs, professional certificates, and even study abroad). Each new search expands your horizons even further.
2. No matter what kind of program you were in at a school, even if you didn’t complete it—a certificate, an associate’s, bachelor’s, master’s degree, or beyond—remember that the entire institution’s alumni base is also part of your network.
If you got your MBA from Texas A&M, for example, you would of course want to peruse the Alumni Tool for the Mays Business School as well as the overall Texas A&M page. But don’t skip other schools within the larger university, such as the School of Law or the School of Public Health. Whether you were part of the Texas A&M community for a semester or a seven-year PhD program, all these alumni are now at your fingertips.
Why are they so accessible? Because graduates tend to feel an affinity for their larger institutions, not just their specific pro- grams (just look at all the university logos plastered over bumper stickers, thirty years post-graduation). Omar, for example, went to UC-Berkeley’s Haas School of Business but always responds to requests he gets from anyone who’s ever been affiliated with UC-Berkeley. He loves Cal, not just Haas—and definitely not just MBAs.
3. You can custom-search far more than a location (e.g., “Austin, Texas Area” on page 68) with this tool. Don’t see a specific company, skill, or area of study in the default list of the top fifteen results? Click the “Add” button atop any of these dimensions and use the search to find the right, LinkedIn-standardized match to narrow your list:
4. For any additional search criteria that don’t fit within LinkedIn’s standardized options, you can add them using the search box at the top of the Alumni Tool:
For instance, let’s say you only want to see graduates who are in the field of Corporate Social Responsibility. Just do a search for that phrase (in quotes to capture all the words of the phrase together) and hit “Return.” Now you can see all the alumni who have that specific field anywhere on their profiles, plus updated data on where they live, work, and more:
Corporate Social Responsibility is also known as “CSR,” so you can add an “OR” operator to catch more than one phrase and widen your search.
These focused methods of finding alumni are especially help- ful at the outset of your job search. This way, no matter what’s most important to you, you’ll have a tailored list of pathways to explore. Instead of settling for just the jobs you know, you now have visibility into both a larger and more realistic set of potential jobs that you might actually, dare we say, enjoy! Just as important, you’re laying the groundwork for a network of school-affiliated people who can help surface opportunities and eventually get you in the door.
Now let’s get into how to tap the power of these career maps to build real relationships.
Hold Up—What If I Didn’t Go to College?
We’ve focused so far on examples of college and university networks. But what if you didn’t go to a four-year school? After all, two in three Americans haven’t completed a four-year degree.
Good news: The true power of LinkedIn is that it’s not some exclusive old boys’ club. Anyone can tap its data to accelerate their career. Here are two other options, no matter your educational background:
- LinkedIn has the Alumni Tool for almost any school in the world, including vocational programs and high schools—a truly unrivaled data set of career paths to explore. So you can search for and explore any and every school you attended.
- LinkedIn also offers a similarly filterable solution for companies. Say you’re already working somewhere but want to explore the ins and outs of different roles—and the folks who hold them—at your organization. Just search for your company and click the “People” tab.
Bam! You can now explore lots of paths within your current employer (the easiest place to start) but beyond the specific job you’re doing today. Then you can also view the paths and required skills of people at other companies where you might want to work next.
Part 2: Test Your Options
You’ve just taken the critical first step: discovering an entire uni- verse of plausible professional options. This is especially something to celebrate if you’ve been feeling stuck or overwhelmed up to this point.
Now it’s time to test out those options. While it might be tempt- ing to say, “Wow, look at all these philosophy majors working at Nike; that’s the path for me,” it’s an even better idea to talk to those philosophy majors before you take the plunge.
To appreciate why, imagine this scenario: You spend the next few months hustling to land a plum job at Nike. You finally make it in. And then on your first day, your boss says: “Hey, do you mind updating all these spreadsheets by the end of the day?” Which is really too bad, given that spread- sheets are your own personal kryptonite. And the mere sight of all those blank cells makes your eyes start to bleed. And every time someone says, “Pivot Table,” you start to break out in hives. . . .
Okay, you get the picture.
To avoid this fate, you want to really dig into each possible career path and understand exactly what it entails—what would you actually do in this role, is it a good fit for your superpowers, and will it bring you meaning or misery?
The best way to do that is to talk to people who do the job—i.e., the alumni you just uncovered in the last step. After all, if you had the choice between reading about a chocolate cake in a cook- book and tasting the cake right here and now, who wouldn’t go for the real thing? The same concept applies to career exploration; there’s just no substitute for learning from real people with real expertise.
The best way to explore is to talk to the people who actually do the job.
Here’s exactly how to start up those essential conversations:
1. Once you run your initial filter(s) on the Alumni Tool to narrow down the pool of users, scroll down to see the alumni doing the very jobs in the very places you’re excited about:
2. Pick one who is doing something intriguing and click the “Connect” button. Then, be sure to also click “Add a note” (since you want to make it clear why you’re reaching out):
3. Now, here’s the most crucial part. Many people blow it by saying something like, “Hey—can you get me a job?” or “Let me tell you how awesome I am!” While you might want both things, neither is particularly appealing to an alum.
In fact, if you’re an alum yourself, you might have received at least a few messages like this. If so, you know all too well that no one wants to be so plainly sold to or used in such a transactional way.
Worry not, however, because the vast majority of alumni are happy to help out—they just want to feel good about it. They want a chance to tell their own story or steer the next generation clear of the mistakes they made. But here’s what you will almost certainly not hear: “Oh, sure, let me serve you up a job on a silver platter just because you happened to be one of the 300,000 other people who went to my school!”
So here’s an example of a note that gives the alum the spotlight instead of a sales pitch (you can find a template for this kind of outreach at the end of the chapter):
The key elements here are:
- Playing up your shared affiliation from the get-go.
- Flattery (let’s be real, it works).
- Conveying you won’t waste their time.
- Next week is always better than this week!
Once you’ve sent this first request, don’t stop there. You want to reach out to at least five alumni, with a goal of having three real conversations (aka “informational interviews”) per career path. Why? Well, for one thing, you’re unlikely to hear back from every alum. You also want a diverse sample of experiences to help you get focused while making a potentially foundational career decision.
For the alumni who do respond, be sure to keep track of what you learn. Make the most of each conversation by doing the following:
- Ask great questions to accelerate your learning (see Sidebar on the next page).
- Follow up with a great thank-you note. It doesn’t have to be long, but it does need to include some of the things you learned. The alums should know that the time they invested in the call was well worth it—and they’ll be all the more likely to want to help you again in the future.
After each of your three (at a minimum) informational inter- views with alumni who have desirable job titles, work at companies you’re considering, or have taken career steps you want to emulate, it’s helpful to rate your level of fit. Here’s a basic rubric to evaluate what you’re learning:
- 3: Great Fit—I’d love doing this kind of work, it plays to my strengths (but with some healthy “stretch” and learning), and I’d feel good about what I accomplish there.
- 2: Okay Fit—This work feels somewhat interesting, I could definitely get it done, and I’d have a decent sense of accomplishment.
- 1: Bad Fit—This work seems fairly boring, I’d have to work really hard just to be mediocre at it, and/or it would give me very little sense of meaning.
Let’s look at an example: Say you just interviewed a high school math teacher, who’s told you about his days of engaging his students, helping them navigate tough challenges both at school and at home, and ultimately guiding them toward success. If you love to tell stories, have incredible interpersonal skills, and are motivated by making a difference in a young person’s life, you might rate that role a “3.” If your true love, however, is finding patterns hidden in data, your number-crunching skills are off the charts, and you’re most motivated by making sense out of lots of information, this might be a “1” for you.
Either way, your overall list will give you an average rating for each potential pathway. You can then compare the overall ratings across each of the paths to identify the one you should pursue first. Instead of stumbling out of the starting blocks like so many job seekers, you are now armed with a compass pointing you to a clear North Star.
Great Questions = Real Insights
To make sure you get the most out of your connection with fellow alumni, get ready to ask great questions. Again, you’re not pitching yourself or asking for a job—you just need the real, unvarnished truth about what the job is like.
Here’s precisely what to ask them during a phone, video, or coffee chat:
- How did you go from school (or a different type of job/role) to your current role?
- How does your job compare to school and tap into what you studied there?
- What do you do all day?
- What do you love the most about your field?
- What’s most frustrating about your role?
- What has surprised you most?
By asking these questions, you can get a sense of what it’s really like to be in their shoes—what the job feels like, how it compares to your shared experience, and what you might not expect as someone on the outside.
Exploring an Internal Transfer
While many of the methods in this chapter are designed for people entering the workforce or making a significant career change, the same underlying principles apply to current employees consider- ing an internal transfer. Because a great new job—maybe even your dream job—might be just down the hall.
Often, it is.
In fact, roughly half of jobs are filled by internal candidates—it’s a whole job market of its own. So if you’re pondering (or at least open to) an internal transfer within your current workplace, you’re not wasting your time on this chapter. Much of the process is quite sim- ilar, but here are a few nuances for the purely internal job search:
- You will likely find that LinkedIn is more useful than your internal employee database, if one exists. In addition to names and titles, the site gives you a career dossier for everyone in your organization. You can find people with shared interests (e.g., the Director of Sales attended your alma mater, or the Head of Facilities volunteers with the same nonprofit) that can make it easier to strike up a conversation.
- Just like you can play the “I’m a student” card when you’re in or newly out of school, you can also play the “I’m a colleague” card. This is a very strong “in” that should engender a response while networking. But it is not a license to abandon the rules for cold outreach. Don’t get too transactional too quickly; try to convey why they’re the right person; mention shared connections; flatter them; and don’t waste their time.
- Since a potential connection is already in your company, flattery can go even further than normal. They assume, and you can play on, some prior knowledge. Maybe mention something they said in an all-hands meeting, or say that their reputation precedes them.
- Start with a lightweight “would love to get to know you and what your team does” ask. Don’t ask for a referral in the first call or coffee chat unless it lasts more than an hour and you’ve said a lot about yourself, or you know they’re hiring for your dream job. You should instead have lots of nuanced questions and end by asking if they would be willing to be a mentor.
Most companies will have a process for internal transfers. Understand that process. Oftentimes it will include alerting your current manager once you decide to throw in for a new job, which could potentially be a thorny situation. You must weigh the risks and benefits here, but your HR department and/or recruiting team should be a safe place to help you do so. Also, keep in mind that anyone at your company using LinkedIn’s Recruiter can’t see that you are open to new opportunities, so there’s no way to indicate to them that you want to be considered for an internal move. You can of course make this visible to all members (see page 107), but we don’t recommend that unless you’re really willing to throw caution to the wind.
From Passion to Profession
We first met Andrew Kung while we were all working at LinkedIn. He was a talented recent grad who seemed to have it all: a highly selective job at a fancy-shmancy company with enough compensation to put his instant ramen–eating days behind him.
There was only one problem. Andrew felt stuck.
That’s because he was doing a type of job the world expects new grads to do (sales and customer support), not the one that he really craved and excelled at (photography). But unlike many new grads—and frankly, a lot of experienced professionals, too—Andrew wasn’t content to just defer his dreams indefinitely. Instead, he started reaching out to professional photographers through his connections on LinkedIn and realized that his dream was completely attainable.
By learning from these insiders, Andrew started to imagine an alternative future that wasn’t just pure fantasy, but one that was grounded in the reality of others’ experiences. Their stories became the paving stones for a career path that he could start to envision.
Buoyed by his career exploration, Andrew requested a transfer to LinkedIn’s New York City office. And within six months, he had networked his way into enough part-time gigs that he decided to quit the security of a big company job altogether. Pretty soon his LinkedIn Headline reflected not only his passion, but his new profession:
Within a few years, Andrew had done photography work for Beats by Dre, HBO, and Esquire—and had his work featured in the New York Times and Vogue, and on CNN.
Andrew shares this reflection on his experience: “Before LinkedIn, I always just relied on serendipity to open doors. But with LinkedIn, I realized I could engineer my own serendipity—and my own future.”
Sample Connection Message for Alumni:
Hi FIRST NAME,
As a fellow SCHOOL alum who also majored in FIELD, I was so excited to come across your profile. I’d love to know more about how you built your impressive career—any chance you’d have a few minutes to chat next week?
Thanks for considering!
—YOUR FULL NAME
Checklist: Exploring
You did it! Instead of being consigned to wander the earth for all time in search of occupational fulfillment—like some kind of career zombie—you’ve just given yourself the antiserum: understanding what’s out there. And unlike the watered-down stuff that you might find on blogs and social media, you went straight to the source: real people doing the jobs you might really land soon. So give yourself a pat on the back for completing the first major step in the modern job search.
Before we move on, here’s a checklist to help make sure you’ve applied everything we just covered:
❑ Explore the career paths of alumni from your alma mater(s). Try applying the following filters to home in on people whose careers excite you:
- ❑ Location
- ❑ Employer
- ❑ Area of study
- ❑ Skills you possess and can demonstrate (or really want to build)
❑ For every career path that intrigues you, reach out to at least five—yielding at least three conversations with—alumni who are in, or have done, the jobs you’re most interested in. For each informational interview, make sure to:
- ❑ Ask great questions that give you a sense of what it’s like to be in their shoes.
- ❑ Follow up with a thank-you note that lets alumni know their time was worth it.
❑ Use these paths and informational interviews to assess your level of fit and narrow down your preferred next step.
Want Even More Insider LinkedIn Tips?
This chapter is excerpted from our brand-new LinkedIn best-seller, Linked: Conquer LinkedIn. Get Your Dream Job. Own Your Future. (Workman/Hachette, 2022). And grab a free copy of my LinkedIn profile checklist - the only one designed by LinkedIn insiders - here.
Key Takeaways
- Your career North Star is crucial: Define it to stay focused, motivated, and make informed choices aligned with your long-term goals.
- Self-reflection and exploration are vital: Understand your values, strengths, and weaknesses to discover what truly matters to you professionally.
- Be flexible and adaptable: Embrace the fluid nature of career paths, stay open to unexpected opportunities, and learn from setbacks along the way.
- Chief of Staff role can have a significant impact on the success of a startup: The author, who served as the Chief of Staff at Dover, credits her role with helping the company achieve key milestones such as raising funding, expanding the team, and acquiring new customers.
- Adaptability is key in a startup environment: The author emphasizes the need for flexibility and the ability to pivot quickly as a startup grows and evolves. She describes how her responsibilities changed over time as the company scaled, and how she had to learn new skills and take on new challenges.
- Communication and collaboration are critical: The author stresses the importance of clear communication and collaboration within a startup team. She describes how she worked closely with the CEO and other members of the team to develop and execute on key initiatives.
- Startups require a relentless focus on growth: The author highlights the need for startups to prioritize growth above all else, and to constantly look for ways to improve and expand. She describes how Dover focused on building a strong product, acquiring new customers, and expanding into new markets.
- The Chief of Staff role requires a diverse skillset: The author notes that the Chief of Staff role is a multifaceted one that requires a broad range of skills, including project management, strategic thinking, communication, and leadership. She also highlights the need for adaptability and a willingness to learn and take on new challenges.
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