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Talking Myself Out of a Job

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Posted: April 2, 2021 | | Categories: Miscellaneous

As I mentioned in yesterday’s post, I have another hiring story to tell, and here it is. The way I portrayed it in yesterday’s post and in the article title above you may think this is a sad story, that I did something horrible that cost me a job opportunity. That’s not the case; what happened was I very honestly answered a question during an interview and that, well, killed the job opportunity for me, but not in a bad way. Let me explain...

The Setup

I applied online for a Principal Program Manager role for a large software company; they have a public service that millions of people use, and they were looking for a PM to shepherd some technical, and likely customer impactful, infrastructure changes they planned for the service. There wouldn’t be a lot of feature development work in this position for a year or more, but the problems we encountered during that first period would be thorny, and for that reason I was very interested in the position.

This is the same position I wrote about where I received an email from the Recruiter letting me know he was interested in looking at me for the position, but all of my response emails went into his spam folder. Once I got past all the spam folder issues with the recruiter, I heard back that the hiring manager wanted to talk with me.

I had the initial conversation with the hiring manager and I left feeling that it would be a great job to have and looked forward to the next step in the process. The hiring manager expected to select a few candidates to put through the next step in the process and I believed I’d be one of them.

A few weeks later, they scheduled my ‘Day Of Interviews’ (ominous music plays) interviews.

The Initial Interviews

The Day Of Interviews started with a follow-up call with the hiring manager. We talked more about the position, and I got a good feel for the team and what the day to day would look like. Still interested in the job.

The next two interviews were with existing PMs putting me through the PM wringer. One was a PM manager on a partner team, and the other was with a Senior PM on the team I’d join if I earned the position. Both interviewers asked me scenario-based questions around PM topics and I think I did pretty well in the conversation mostly because I’ve been around for a while, had several PM positions in the past, and think I know what I’m doing. I do, really.

The Flashback

I have to be very careful at this point because the part of the story I’m about to tell will make you think that I don’t want another PM position. That’s not true. I start a new Principal Product Manager position on Monday and I’m very excited about it.

Before I lost my job at GitHub, I spent a lot of time thinking about the types of jobs I’d be interested in if, you know, I lost my job at GitHub. Yes, I did know I would lose my job at GitHub; GitHub and I were… incompatible. Well, that’s not entirely true, GitHub should have been an excellent opportunity for me, but it just didn’t work out that way. That’s all I’m gonna say about it.

I dug out a pad of paper and pencil, sat in my favorite office chair, and spent an hour or so brainstorming with myself (can you brainstorm with yourself?) about which types of jobs I should pursue.

At the top of the list was PM positions. My last few jobs (I’ve had a lot of them) were PM positions and I’m very comfortable and happy being a PM. PMs help bring products and product features to market and I like doing that.

Bringing in a close second was Evangelist positions. I’m probably happiest in evangelism roles since it keeps me close to developers and lets me write code, white papers, and technical articles plus present technical topics at conferences and customer meetings. All of those things make me very happy. PMs get to write and present, but don’t do so much code writing (and Engineers typically scoff at PM-generated code).

I applied recently for a few evangelism jobs and never got anywhere with them. Honestly, I don’t think I’m cool enough anymore to be an evangelist. When I was younger, I had a goatee (still do but it's VERY grey) and that made me cool enough to be a product evangelist. A Goatee or pony tail were the keys way back when to successful product evangelism roles. Nowadays I’m an old, bald, grey-haired guy, which isn’t ‘evangelism cool’. I recently started wearing hats more frequently, mostly because I’m bald, so perhaps if I got a really cool hat and started wearing that all the time I’d be cool enough again to be an evangelist. Who knows?

Next came Software Engineer. Yes, of course, software engineering roles are really, really cool. Lots of hard work. Building cool stuff. People using your stuff. Focused work. But, even though I identify as a software developer and play one on television, it’s been a really long time since my job was writing code. I know a lot of development languages, a lot of server and cloud technologies, and I know how to make award-winning commercial products that work. Hold this thought, I’ll get back to this topic later.

Final option? CTO, of course. I built and ran a successful commercial software business that created several award-winning products. IBM even sold one of my products worldwide (you’ve heard of them, right?). I earned a position at Forrester Research as a Principal Analyst where customers paid a lot of money to pick my brain about software development topics. I know the market, I know the technologies, I have the experience. But is anyone going to hire me as a CTO coming directly from a series of PM roles? Probably not. Sigh.

A lot of important items appeared on that page; things like: ownership/control over my destiny, huge salary, stock awards, great benefits, etc.

Critical conditions for any role? Must be interesting. Must be intellectually challenging. Must be fun!

Many years ago I built and ran several technical teams. When I left the enterprise consulting world and moved to mobile, I left management roles for Individual Contributor (IC) roles. After almost 16 years of this, it's time for me to start moving back into management roles. So, for this job search, I promised myself I’d let every hiring manager know I wanted to be in a position where I could grow into management and/or mentoring positions again. Not a requirement, only that it be a potential option for any role I seek.

Fast-forward a Few Months to Another Flashback

Alright, so after several months in search of a job with no offers, I was despondent. I uncovered a lot of opportunities (more than I expected), worked really hard to earn the position during the interview series, made it through the Day Of Interviews, only to lose the job with limited or no feedback weeks later. Frustrating.

Honestly, I think ageism played a role - that and I didn’t wear any cool hats during interviews, but perhaps that’s a story for another time.

It was time for some honest soul searching. One Friday night, over an excellent bottle of wine and charcuterie in our kitchen, I had a really honest conversation with my wife. My wife is amazing; she’s been an amazing partner for more than 20 years and we talk about EVERYTHING. She understands technology and used to work at IBM and other technology companies. I knew I could bare my soul on this topic and together we’d figure out what to do next.

So, lots of opportunities, lots of interviews. No jobs. Was it me? Yes, it very well could be, and likely was - no reason to have blinders on. What to do about it though? Was it the missing cool hats? Possibly, but probably not. Did ageism play a role? Who knows? Was I looking for the wrong role? Possibly.

Would I rather be an Engineer, yes, absolutely. However, I don’t think anyone’s willing to pay me to be an Engineer right now, or at least not pay me as much as I’m used to earning. I know a lot (an awful lot) about software development and Engineering, but it hasn’t been my ‘job’ for a really long time. I clearly have some insecurities about this and I should get over them.

We talked for a long time, and may have opened another bottle of wine; the details at this point are fuzzy. I ultimately decided that I would continue to look for PM roles (I finally got one, woohoo!). I would stop looking for evangelism roles - I’m just not cool enough anymore. I would start looking for Engineering roles or Engineering Manager roles (with reasonable expectations, of course).

With my path firmly reset, a few days later was my Day Of Interviews...

The Final Interview

OK, so it's time for my final interview for this job. I was pretty exhausted from the previous interview because the interviewer had a formal, structured series of questions that he expected me to answer and I didn’t feel that it let the real me shine through. He drove me to answer specific scenario questions and really didn’t let me tell stories about my career and past experience like I like to do in an interview.

The final interview was with the VP of Product for the group, someone with 50 people or so (PMs and PM Managers) working for him. I really wasn’t sure what to expect from him and I had no way of knowing how much he’d know about me at interview time. Boy was I surprised.

We started with some excellent pleasantries, he was very easy to talk to. Next, he mentioned that he reviewed my resume, my blog and my public GitHub account (public repositories) in preparation for this interview.


You mean to tell me that this Product VP spent the time to really, really get to know me before our interview? Holy Crikey - he actually got past my resume and tried to get to know the real me.

Through 6 months of interviews, very few people looked at anything except my resume, and perhaps my LinkedIn profile, to learn about me. In several interviews, the interviewer looked at my resume for the first time while I sat there waiting at the beginning of the interview. Remember, in my previous post I mentioned that several companies asked me to do coding exercises as part of the interview process while completely ignoring my 7 books on software development topics, multiple technical magazine articles, and my 60-some public repositories on GitHub as examples of my coding skills.

This guy actually studied my code before interviewing me. He mentioned during the interview that he had some software development topics on his list of interview questions, but dropped them after reviewing my GitHub repos. I think, perhaps, I blushed at this point. I know I had goosebumps.

Anyway, on to the main purpose for this article (finally, I know). Here we go...

His first interview question was essentially “Having looked at your blog and your public GitHub account, I have to ask you: Why do you even want this job? Wouldn’t you rather have an Engineering position?”

Having just spent hours drinking wine and talking with my wife about my job search, I had the answer queued up. I told him that I was an Engineer at heart but my most recent experience was with PM roles and that’s where I felt most comfortable. I mentioned that I usually describe myself during interviews as a software developer with more than 30 years of experience; doing this to highlight to interviewers that I’m a PM candidate with strong technical chops. Yes, of course I’d rather be an Engineer but I just didn’t think I had enough recent experience to justify earning the position.

That was the exact moment when I talked myself out of the job.

I told him that my insecurities kept me from seeking an Engineering job and he agreed (which was excellent, honest feedback from an interviewer). He said it was time for me to update my resume and that he’d pass my current resume and some feedback on to some Engineering VPs within the company to see what opportunities he could find.

A week or so later I got an email from the recruiter letting me know I didn’t get the job, but I already knew that 15 minutes into the last interview, and I’m OK.

Did I update my resume with an Engineering slant and start looking for Engineering positions? No, I didn’t. A short while after that interview I earned the PM position that I begin on Monday and I’m very excited for it. Did I ever hear back from the VP? No, I didn’t - although I pinged the recruiter several times on the topic.

When you learn what I’m doing in this new job, you’ll understand why this new position is so exciting for me. It leverages my experience and skills in a specific mobile development area and puts me in a company that produces a leading product in a product category I studied and worked in for something like 10 of the last 16 years.

Will I ever go looking for an Engineering position? Who knows. I have a few years of work to do before I can relax financially. I’ll keep my Engineering skills current (I always do) and perhaps when I can retire, but before I do, I’ll look for an Engineering position to keep me busy until I actually retire.

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