Ups and Downs of a Job Search — Part II

Before we get into this, I am not going to name names here. Interviewers, recruiters, and hiring managers are doing their best. Naming people and companies is unfair, as everyone is genuinely trying to find the best match. It is the system that is in a broken state, individuals on both sides of the table are doing their best.

The Interviews

Getting the interview is a great feeling. You are finally able to put yourself forward and engage in a conversation. Because of this, you are also able to observe the absurdity of the process firsthand. Let us take them in order of how far I got in the conversation.

Photo by Christina @ wocintechchat.com on Unsplash

Recruiter Screens —

I had at least three of these that did not go past the recruiter calls. Here is how they ended.

1. A position that was a carbon copy of an engineering leadership position I had held in the past, the recruiter conversation went great. I had done the exact things that they were looking for with a similar-sized team. The only slight issue could be that I was at the higher end of the pay band, but still within the band. I got a ‘we are not moving forward’ email, which was a bit of a surprise.
2. This was for a VP-level position in Technical Program Management within an industry where I have extensive experience. I also got some excellent references. In fact, I had initially applied for a Senior Director position and was redirected to the VP position. Great conversation with the recruiter. We saw a perfect fit. I got the feedback that the hiring manager was moving on, as I did not have enough “scaling experience”. I don’t think I did myself any favors by responding to the email with a link to my book on scaling.
3. A Director of Architecture position that would have really helped me flex my engineering chops. A highly respected ex-colleague referred me in for this position. Once again, a great and positive conversation. My salary requirements exceeded the stated budget for the position, but I was willing to accept a lower salary in order to work with someone I truly enjoyed. The recruiter told me they would have me talk to someone on the hiring team, but about a week later, I received a rejection email.
4. A director-level engineering execution role at one of the most famous fast-food companies in the world. Spoke with the recruiter whom I had known before. Great conversation again. The hiring manager seemed to like my profile, but was looking for someone with more consumer-tech experience. Completely fair and understandable.

The above hopefully demonstrates that even getting a foot in and doing well in the recruiter screen is not a guarantee for moving forward in the process. The recruiters are always happy to talk to qualified candidates and want to help them get in, but they are working within systemic constraints of the organization.

Hiring Manager Conversations —

A couple of references led to direct meetings with hiring managers. These were very interesting as they provided great insights into the expectations and demands of the positions.

1. A VP of Software Engineering position at a small-ish firm. The conversation was with the CEO. It went well, not necessarily spectacular, but well. I looked back at it and recounted a couple of missteps I made. Never heard back about the position.
2. An undefined role in the “Office of the CEO” organization at one of the largest electric power producers in America. Something that sat between strategy, product, and execution. The role wasn’t well-defined, and the organization was still in the process of taking shape. Did not hear back on this one either.
3. Director-level role at a large consulting company. I was referred in by an ex-colleague and a good friend who has been doing great at this company. The conversation started a bit rocky, but took a great positive turn midway. Unfortunately, within a few days of the conversation, I received a great offer and had to walk away from pursuing this role further. The role sounded exciting, but the stars did not align.

Full Rounds —

There were two companies where, after the recruiter screen, I was able to move to the screening interviews. In both these cases, I was asked to return for the full round of interviews. Instead of organizing them by position or company, I will approach them by type. The types of these interviews have a greater impact on the candidate's psyche than the organization being interviewed for.

1. Project Retrospective — This interview is about a project that you led or were a part of in the past. Ideally, select a project with ups and downs. I talked about two different projects in two different interviews. Preparing for this one gave me an appreciation for the work I had done in the past.
2. Behavioural — A demonstration of soft skills via stories. I had a little bit of heartache with this because many of what would be considered ‘stories’ were just natural day-to-day work for me. I had to spend time reviewing timelines and the order of events to ensure I had them correct before presenting them in an interview.
3. Management Attributes — Diving into your philosophies as a leader. How have you overcome conflict, obstacles, communication issues, etc? Similar to behavioural, I had to spend a bit of time, making sure I had my stories straight.
4. System Design — I had three of these. The prep for these was a bit intense. I had not drawn a system diagram since 2021, and that too was on a whiteboard. Watched lots of YouTube videos. Had some sleepless nights preparing. Spent some time doing mock interviews with my wife over coffee. This definitely contributed to some sleepless nights. Turns out, I had gone a bit overboard with the prep, but it's better to be overprepared. This was also a great exercise in getting back to formally talking about important development concepts. It helped a lot with the mindset of interviewing. ProTip- Do system design for past systems you worked on and think through what decisions you made and which ones you should have made instead.
5. Coding Interview — I had only one of these, and this gave me sleepless nights and frustrating days. This one deserves a section on its own…

Coding Interview

Solve two medium-difficulty problems in 40 minutes—medium as defined by Leetcode. Oh, you will get familiar with Leetcode. It will be challenging, frustrating, at times rewarding, but for the most part terrifying. It will pummel you into submission.

Leetcode is a website that has a collection of coding problems. These are initially very unintutive, at least they were for me. Over time, you start seeing patterns in how to solve these problems. There are 4–5 patterns that repeat. All this, though, you discover by spending hours and hours on YouTube, doing research on how to solve these hard questions. You give up multiple times and then go… well, maybe a couple more problems. I got to the point that I was looking at solutions first and then trying to replicate them. It honestly worked better than trying to solve these coding puzzles directly.

The solutions are not of the greatest difficulty, they are challenging, but doable. What is challenging is coming up with a solution within the allotted time while meeting the time and cyclomatic complexity requirements. That is what starts to take a psychological toll. You have almost never done this before in real life. You most likely have taken your time, weighed options, and made measured decisions. Doing all that in 20 minutes, while talking through your solution with an interviewer…there likely isn't much in your past experience to prepare you for that.

Everything, Everywhere, All At Once

I had twelve of these interviews over the course of eight days. This was while doing my regular consulting and training work. The weeks leading up to these interviews were preparation time. In all, there were at least three weeks of either sleepless or tired to the bone, cannot keep my eyes open nights.

Getting to the full rounds is great because you are truly able to show your skills. The flip side is that there is naturally a lot of pressure. You have made it to the last stages and do not want ot mess this up. People spend 3–6 months on Leetcode. There is an entire industry dedicated to helping people excel in these interviews. The pressure can be overwhelming. The process can be tiring, and being rejected after all that is devastating.

My advice is — Spread the prep out. Keep notes of things you do at work. When you work on something major, sketch it out. Randomly solve coding problems even if you have a job. Collect stories as you go so that you do not have to piece them together later. Do a favour to your future self and always be prepared to interview for a job.

A note on the recruiters — I met some excellent recruiters through this search. They were courteous, helpful, and very accommodating. Hats off to these folks taking care of all aspects of the interview process for the applicants and interviewers.