Finding a job in unusual times

5 reflections on a months-long journey

Photo by Caleb Jones on Unsplash

I left Grammarly at the end of 2018 and after taking 2019 as a Sabbatical year with a pretty lightweight consulting load, I started my job search in earnest in Feb-March 2020. Consulting was never a thing I aspired to do, but certainly an experience that I was eager to explore. When it was time to ramp up my professional intensity (and income) I chose to focus on another tour-of-duty in an in-house role rather than on building my consulting practice up to a full-time-equivalent volume. 

There was only one wrinkle. COVID-19 hit the US at full speed, and my target sector, private tech companies, was holding its breath: freezing hiring, furloughing staff, and in some cases, conducting painful layoffs in an effort to extend cash runway faced with a future that just gotten way more unpredictable. I could not have picked a worse timing to look for a job. 

In late August, my job search concluded successfully, accepting an offer from a wonderful company for a dream role. This is a great time to reflect on my journey and share some lessons, for my own future reference, and hopefully for the benefit of others as well. 

1. Establish a rhythm

At the beginning of the search, I was following a very loose plan. I’ve been spending a lot of time in the previous year thinking about goals and how to pursue them wisely. Knowing that I’m not fully in control of the outcome, and without an external feedback mechanism: am I doing too much, overestimating my ability to influence the outcome and exhausting myself unnecessarily? or doing too little, resting on my laurels, underestimating my ability to influence the outcome, and unnecessarily prolonging an extremely uncomfortable situation when I could have done more? 

The insight came from looking within, reflecting on past challenges and situations and realizing that in this particular case, I’m likely doing too little than too much. That gave me the conviction I needed to push myself harder and put together a more disciplined plan. I certainly consider myself a creature of habit, so designing and scheduling a recurring set of activities was the best way for me to ensure that my actions reflect my intention. 

My job search rhythm consisted of the following: 

  • Daily — Review LinkedIn jobs emails that were pushed to my inbox based on 3 keywords I set up in advance, and take action on any relevant opportunities. 
  • Weekly — Go through the VentureLoop job board. Given my target sector, this was the job board most likely to yield relevant opportunities. 
  • Weekly —Continue to publish content on OrgHacking. The content I published on OrgHacking over the past 6 years has become a powerful tool to demonstrate what I’m bringing to the table in a way that a resume never could. I created a sample portfolio with some of my best posts and referenced it in my outreach emails. 
  • Bi-weekly — Go through a set of GlassDoor job searches. Lower ROI but still a very popular option with my target sector. 
  • Monthly — Exec search outreach — I built a list of the 15 top exec search partners in my domain and checked in with them on a monthly basis to see whether they’re running any relevant searches. 
  • Monthly — VC talent partner outreach (at a 2-week offset from exec search outreach) — I built a list of the 15 top VC talent partners and checked in with them monthly to see whether they know of any relevant openings in their portfolio companies. 

2. Manage the pipeline

As my rhythm was picking up steam and starting to bear fruit, I needed a system to keep track of the opportunities and ensure that I’m not dropping any balls. 

It was helpful to distinguish between a “lead” — a job opening that I saw/applied to, or a person that I was introduced to. And a “viable opportunity” — a job opening where I had at least one real-time conversation (phone or video) with the hiring manager or recruiter. 

Once a lead graduated to a viable opportunity, I added it to a simple Google Sheets tracker that I updated daily with the following info: 

  • Status: Open, Closed, On-hold
  • Company
  • Role
  • Hiring Manager
  • Hiring Manager role
  • Source
  • Stage: Recruiter screen, HM screen, assignment, on-site, final round
  • Last contact 
  • Notes

3. Introductions, introductions, introductions

In my almost-20-yr career, I have never gotten a job by blindly submitting a job application. And not for lack of trying. With the hyper-competitive market dynamic that COVID-19 created (scarcity of jobs and abundance of candidates), I figured that’s not going to change and focused on finding someone that can introduce me to the hiring manager (preferably) or the recruiter, regardless of how I first learned about the opportunity. 

4. Ask for help

This is a personal growth area for me that I’ve intentionally focused on in this search. My independence has been a deep source of strength in my life, but it’s not without its shadow side. While asking for help showed up in many ways in this journey, these were the key ones: 

  • Leaning on friends, family, and especially my partner, Kimberly, for moral support and sage advice. 
  • Adding the “open to work” frame to my LinkedIn profile. Publicly admitting that I’m looking for work. My inner daemons told me that there’s still a stigma around it and that it can come across as desperate. I decided not to listen to them and do it anyway. 
  • Working with a career coach. A good colleague and strong executive recruiter happened to complete a coaching training and was looking for his first coaching clients. I took him up on his offer and found the added accountability and advice to be extremely helpful. I tend to think of myself mostly as a “think first, talk second” kind of person, but more and more I’m learning that talking about unbaked thoughts out-loud is a powerful way to advance and distill my thinking. 
  • Making semi-open requests to my immediate network. This was the hardest and most valuable for me to overcome. I had no issues asking a specific person for a specific introduction, but felt extremely uncomfortable with a generic network-wide blast of “hey I’m looking for work, send relevant opportunities my way”. Partly because I think it’s ineffective, but partly because of my inner daemons. I landed on a middle-ground solution where I reached out to a dozen people in my network who I trusted the most, asking them to introduce me to three connectors or relevant hiring managers who are hiring or may be hiring in the near future. The combination of a more targeted outreach with a more targeted “ask” got me over the hurdle. The job offer I accepted can be traced back to one of those emails. 

5. The 5 Fs

At the end of my search, I needed to choose between two very compelling but very different opportunities. It was a tormentous decision, but one I was lucky to have to make, and at the end of the day, a clear winner emerged. 

In hindsight, had I used the “The A Method for Hiring” 5Fs framework, making the decision would have been a bit easier: 

  • Fit ties together the company’s vision, needs and culture with the candidate’s goals, strengths and values.
  • Family takes into account the broader implications of the job to the candidate’s family. 
  • Freedom is the autonomy the candidate will have to make his or her own decisions. 
  • Fortune reflects the stability of the company and the overall financial upside.
  • Fun describes the work environment and personal relationships the candidate will make. [personally, I have a more profound definition for fun]

While the differences were far more nuanced than this, one opportunity was stronger on “fit” and “fun” while the other was stronger on “fortune” and “freedom”. “Family” ended up being the area that tipped the scales quite heavily towards the winning opportunity. 

Finding a job in unusual times

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