Design Thinking for Navigating the Job Market

Like most millennials, a year into my first job, I began exploring other career opportunities. Based on Stanford d.school’s design thinking method, I took a modified design thinking-esque approach to navigating the job market with the following steps:

1. EMPATHIZE
2. DEFINE
3. RESEARCH
4. PREP
5. NETWORK/INTERVIEW

❤️ EMPATHIZE

Like the traditional design thinking method, the first step is to understand the user (yourself) and the problem. Create a persona of yourself, evaluating your skillsets, wants, needs, likes, and dislikes, etc. This might be something you already have defined, but personally, I found myself constantly going back to this step and iterating on it.

What skills do I have and what positions could I even be considered for? Do I want more work/life balance so I can prioritize personal interests and hobbies? How much does location matter — would I mind staying in Chicago for another year or should I only be looking at opportunities in NY to be closer to friends/family or maybe I could move to the West Coast because if I don’t do it now, I may never get the chance?

A couple things to consider (but not limited to):

• Location
• Compensation
• Career progression
• Work / life balance
• Industry / subject matter
• Size of the company

A little background, I had been working as a Digital Strategy Consultant, with a background in Business Administration and Decision Science and was considering a variety of options: strategy consulting, innovation consulting, product design/management, data analytics, etc…

I started off by evaluating what I didn’t want. Initially, I was tempted by the idea of working for some cool, trendy startup with beer kegs and personal chefs, but decided that I wasn’t ready to give up working on a variety of projects and across industries. Then, I considered more data-driven roles, but concluded that I wasn’t necessarily looking for positions with “data” in the title and wanted to focus on developing more soft skills as well. I’d spent the last year advising companies on designing and developing internal systems, which aligned well with product and innovation roles, but what was the point in leaving just to do the same thing?

Basically, that landed me back back at square one: consulting. I wasn’t particularly keen on the idea of case prepping again and started asking myself:

Am I just leaving just to leave? What if the next place isn’t as good and I’m just wasting my time while I could be focused on developing myself here? Am I just getting distracted by all my peers who ramble about their job hunts? Should I be listening more to the risk-adverse advice of my parents and stay put?

I loved the company I worked for, had great work/life balance, was involved in several internal initiatives, and already had a network of friends and mentors. This made me ultimately dig deeper and understand what I lacked in my current role that I was seeking in future job opportunities, which came down to size of the company, project work, location, and work/life balance. The firm I was at grew nearly 50% since I interned there and there were constantly new faces that I didn’t know. I felt myself being drained from all the small talk and not even noticing that I’d gone months without seeing some of my friends. I’d been on several interesting projects throughout the year that pushed me to work in industries that I had little familiarity (or interest) in. And although I’m grateful for those experiences, I wanted to be somewhere where I could do more data-driven and strategic projects in the retail/consumer goods industry. Also, for personal reasons, I was constantly traveling back home and everyone would ask me “do you even live in Chicago?” Financially and time-wise, it made sense to move closer to home. And you know how I mentioned the work/life balance? It was kinda too good. I know people say they “thrive in high-pressure environments,” but I realized I needed some sort of pressure and structure in my life because without it, I couldn’t truly value all the time I had and found myself wasting it binge-watching shows on Netflix. Someone once said to me that “the work we’re doing isn’t life or death” and it’s more important to have time for yourself outside of work, but hearing that made me realize that I wanted my work to be “life or death” or at least something worth spending 8+ hours a day doing. Truth be told, I’m 23, unmarried, no kids yet, and no real responsibilities and want to be developing myself so I can make a greater impact on society.

Wow that went off on a tangent…

TL;DR moral of the story: figure out what you want

📌 DEFINE

Once you have an idea of what you want and are looking for, it’s time to start asking the more nuanced questions and start planning. This involved A LOT of LinkedIn job searches, Googling “[X company] careers,” and indecisively saving links for 90% of the positions I came across.

Spreadsheets and Kanban boards will be your best friends here. Personally, I managed my Recruiting process using notion.so (a free project management tool that basically combines Google drive, Asana, Trello, OneNote, and more).

(Shameless plug, create an account using this link for one month of unlimited data storage: https://www.notion.so/?r=116b28cef0044fccaad8e38c670bf4f3)

Start compiling a list of positions and companies that you’re interested in and their deadlines. I used a table / Kanban to track my application progress for each company and a separate table / calendar for some over-arching to do’s like:

• Update resume
• Create cover letter template
• Draft cold email template
• Interview prep

This timeline may change depending on your availability and initial uncertainties of how long each task will take, but take a stab at defining potential tasks and estimate timeframes for each. Revisit this throughout your process to make sure you’re completing everything you set out to do.

Keep in mind, some companies have a longer turnaround depending on their hiring cycles and the size of the company. For larger firms, it was often a more complicated process to get referred and schedule interviews and I ultimately didn’t pursue those interviews because the timing didn’t align with when I had to accept my offer. If you’re set on pursuing opportunities at some of these places, I would recommend staggering your efforts to start with those companies and allow for more time to get interviews and offers. Furthermore, entry-level positions may be typically filled by undergrad or grad school recruits so try to schedule your timeline around those months if possible. I started having initial calls with firms in March and interviewed and landed offers in June to maximize the amount of unfilled positions.

Notion also has a Recruiting template, which is similar to the Kansan I used (example below) to track what stage you’re at in the recruiting process with each company. It can start to get jumbled when you’re trying to remember who you need to follow up with and who you’ve already contacted so I tracked each company as either networking, referred, applied, interviewing, received offer, or rejected.

📚 RESEARCH

I’ve found that people are actually really willing to help you if you just reach out. I began by compiling a spreadsheet of LinkedIn searches, noting down the company, position, and any other relevant information of people I was interested in connecting with. Then I cold-emailed batches of people asking if they’d be available for a quick call, which I received ~20% response rate to. Couple tips and things to keep in mind:

• Spend time perfecting your resume and potentially create multiple versions to improve your response rate.
• It’s usually pretty easy to do a Google search for a company’s email format. Also, if you have access to CareerShift (check with your university), you can also find contact information for a lot of employees.
• Look for people who may have something in common with you (i.e worked at the same company or went to the same school).
• Start by reaching out to a handful of people at a time so you can make sure that you are available to schedule time to talk to everyone who responds in a timely manner.
• Reach out to analysts/associates (~1–3 years into the job) during this stage so you can get to learn more about the company and ask any “dumb” questions. Use this time to learn about the company and role and save networking with more experienced employees (managers and up) for when you’re ready to be referred and start interviewing.

Below is an example of the email template that I used when reaching out to people:

Hi [insert name],

My name is Sophia and I am currently a [insert job title]. I graduated from [insert school] with a degree in [insert degree]. Provided on this email is a copy of my resume for reference.

I came across your LinkedIn profile and am interested in the work you are doing at [insert firm]. I was wondering if you’d be available for a quick phone call to learn about your role and experiences. My schedule is flexible over the next two weeks and I am happy to work around your schedule.

Let me know if you are available to chat. I look forward to hearing back from you.

Best,

Sophia

Once you start getting responses and scheduling calls, prepare a list of questions to ask and make sure to take notes so you have them for reference when you’re prepping for interviews. A couple questions I asked includes:

• What is your background and role at the company?
• Why did you choose X company?
• Can you provide some examples of past projects you’ve worked on?
• What does the day to day look like?
• What does the company look for in an analyst?
• What is the typical career progression model?
• What is the application and interview process like?

Make sure to follow up with thank you emails and connecting on LinkedIn. It’s always helpful to build lasting relationships in case you end up interviewing or even working there!

✏️ PREP

Depending on what you’re looking to pivot to, this step may look different for you. You’re also probably wondering, what am I even prepping for? I don’t even have an interview… True, however, once you land an interview, you may have less than a week before the company will want to schedule it and prepping early will help you know how much time you’ll need and maximize the number of offers you’ll have to choose between.

If you’re going down the consulting route, this will probably entail fit/behavioral and case interviews.

For fit/behavioral interviews, prepare:

• Your “pitch”
• Why consulting?
• Why X firm?
• Stories about past project experiences that speak to your leadership, analytical, or team building skills
• I’d recommend having a mental bank of ~5 stories available that you can pull from for whatever questions you may receive

📚For case interviews, some resources include:

Case interview prep books

• Case Interview Secrets by Victor Cheng
• Case in Point by Marc Cosentino

MBA casebooks

Case prep coaching/peer prep sites

• https://www.caseinterview.com
• https://www.preplounge.com/en/

I’d recommend doing ~30 live cases before you start interviewing to get comfortable with the structure and formality.

📚For other industries, you can likely expect some sort of fit/behavioral interview as well as a technical interview. Most industries have books with examples interview prep and online coaching or peer prep resources that I’d recommend looking into as well. Obviously, I’m not as aware of prep materials for other industries, but a couple to get you started include:

Investment Banking:

• The 400 Investment Banking Interview Questions & Answers You Need to Know

Product Design/Management:

• Cracking the PM Interview: How to Land a Product Manager Job in Technology by Gayle Laakmann McDowell
• Solving Product Design Exercises: Questions & Answers by Artiom Dashinsky
• The Product Manager Interview: 164 Actual Questions and Answers by Lewis Lin

Software Engineer:

• Cracking the Coding Interview by Gayle Laakmann McDowell

💼 NETWORK/INTERVIEW

Finally, now it’s time to start making things happen! Pull up your list of contacts and start reaching out to managers and up. Don’t get discouraged if response rates are lower. Most of these individuals don’t have much time on their plates, but the more people you reach out to, the better your chances are. Once you start scheduling calls, use this opportunity to sell yourself and lead by explaining why you’re interested in the firm and how your background aligns. Make sure to ask them questions as well — people love talking about themselves! Then, make sure to conclude the call by inquiring about any openings at the firm, next steps, or if they could direct you to someone in HR/recruiting that could assist you. If things go well, this can lead to referrals and interviews.

I know you’re probably still skeptical, but through these steps, I was able to receive referrals for 7 out of 7 firms that I reached out to, interviewed with 3 firms, and received offers from 2 firms before I decided to accept an offer and decline future interviews and applications.

The recruiting process can definitely be daunting and laborious and I was filled with my fair share of rejections in the past, but I’ve found that tracking your tasks and progress through an iterative and agile method can ensure that your end product aligns with whatever vision you have in mind.

Hope these tips help and best of luck recruiting!