THAT STARTUP LIFE: PART III – CHOOSING RIGHT OVER RIGHT NOW

Good day good readers! It’s been a minute since I promised another post. Life gets in the way sometimes, but here we are, ready to close the loop and disembark from the job search and make landfall in San Francisco. Join me for the ins and outs of job searching below and thank you once again for helping me get here in the first place.

I covered the reasons I decided to leave my former employer in THAT STARTUP LIFE: PART I – NEW HORIZONS and how I approached my search in THAT STARTUP LIFE: PART II – PACKAGING UP THE GOODS, but let’s get to the good stuff, what happened during the search and how did I choose Practice Fusion (and why did they choose me.)

It occurs to me that the way I choose to segment the parts of my search says as much about me as it does about the outcomes, so I want to be thoughtful about that as I write this piece. Therefore, I am choosing to segment it in a couple of different ways. First, I think there are meaningful differences in the size/stage of the companies at which I interviewed. Second, there was a differentiation in the approach the company took to filling the role. Third, finally, and perhaps most interesting, I found there to be distinguishing characteristics in the interview process itself. I will try and represent each segment with anecdotal examples and some context. The names of these companies are omitted, not to protect them, but this isn’t meant to be a hit job, just an adventure.

Too big to fail? The bigger the company, in general, the more shenanigans. While their efficiency and speed at getting you into the interview pipeline was far better than other companies, a couple of big companies I interviewed with had some real quirks that were, frankly, off-putting.

• Megalomania: I had one interview at one of the major players in the global tech scene, a brass ring on your resume type place, that went sideways fast. I am a pretty confident person, and I think I look pretty good on paper, but I revel in the opportunity to get in front of people. I think I am even better when I can connect, react, be personable, adjust to their style(s), etc. I could just be delusional, but it’ll be hard to convince me otherwise. My first session at this place was with my potential boss. I immediately understood that he was very disinterested in interviewing me. He showed up late, made no attempt to engage me as a person, rapid-fired a dozen questions, with zero follow up, got up and left. Zoom! Well, that escalated quickly. I then spoke with the person I would be replacing, and her counterpart who I would work closely with, in separate sessions. Both were very nice, and had a reasonable interview style. It went pretty well I think. Towards the end of the interview, they asked me the standard "do you have any questions for me?" Most people I interview ask something like “what is a typical day like?” or “what are the keys to success in this role?”, but I often ask, “what is the one thing you don’t like about working here?” I am more interested in how they handle the question than the answer (pro tip, this is a common approach, how, not necessarily what.) Well, they both flinched, hard, like I had murdered their puppy. Their reaction made me feel like I was absurd to think everything wasn’t perfect there, like they were being recorded and I had now put them in a terrible position. Something was very, very wrong. Their answers were exactly opposite of each other (things move too slow and things move too fast). I got out of there and never looked back. They showed no interest in me, and I was afraid of their cult. Swing and a miss.

sidebar: I’ve interviewed at least one hundred candidates for various positions in my career, probably closer to two hundred, and I have some opinions on interviews that you can read about here Hire Education Part I & Hire Education Part II.

• The Psycho: I interviewed at another big tech player, purveyors of several SaaS products, that many of you are using currently. A recruiter called me in, had a phone screen with my potential future boss, and was flown in to meet with the VP of the department. Things looked promising. I had a concierge on site, a person who would be my colleague in the department, who shuttled me around from room to room, and was very pleasant. First up, the VP. This VP came in like a hurricane, asked me to give the 5-minute elevator pitch right away, then drilled questions, cut me off many times within seconds and criticized my answers the whole way through. It was a bit abusive, and I’m no fragile flower. I honestly assumed some kind of stimulant other than coffee was in play. I then had lunch with some other potential colleagues, interviewed with three of them, all of which went fine. The position had been open for months, and when the recruiter called to tell me I wasn’t moving forward, I wasn’t surprised. Icing on the cake, the reason they offered was absurd. I played it professional with the recruiter, but she kept digging as to what happened, I finally came out with it, that person in charge, was the barrier to their success. I’m not sure they knew what they were looking for, or if anyone could survive the psycho VP. Dodged a bullet there, good luck to all of you working for this nut job.

Why are we even hiring? I ran into this scenario a half dozen times, and I’ll use a couple of examples to illustrate the worst-case scenarios, but it seemed like the most common outcome. Companies who have decided to hire for a role, but aren’t clear about what they want, when they want it, or how to get it.

• Sputtering: I interviewed at a tech company that sold hardware (and supported the software and integration of that hardware) in the energy utilities field. They were expanding into various markets and needed to build their customer facing teams at scale. Alright, I’ll bite. Several exchanges with their HR, and rescheduling, four rounds later (yes, people still do this stupid thing), I got an offer that barely met my current compensation with a less stable future. Whomp whomp. Seriously though, when four rounds of interviews, and 12 people (in a 40-person company) are required to make a decision on hiring someone, you’re doing it wrong. Period. They didn’t know what they wanted, they had no sense of urgency or timeline to get it done, and they couldn’t get the fish (that’s me) in the boat. This was the moment I decided I wasn’t going to leverage my current company. I could have used this offer to do just that, but then I’d have to take the offer if my current company didn’t step up to the plate. I didn’t want to do that, and I realized that if the job was good enough for me to take in a failed leverage attempt, it should be good enough to take on its merits. I was going to leave, I just needed the right fit, not the right now fit.
• Square Pegs: No, not the 80’s TV show starring Sarah Jessica Parker (that’s a Gen X joke, no need to look it up), the square peg/round hole reference. I interviewed with one SaaS company that worked in supply chain. They had one of those reasonably modern infrastructure/ancient interface products. I spent most of the interview with the staff who would be reporting to me, and they made it clear they felt understaffed. They wanted to be sure I would DO the work they were doing too, as an individual contributor. Listen, I am more than willing to climb into the trenches and understand the work, throw large amounts of my effort at emergencies and deadlines, but this was a Director role, and they were looking for a team lead? The boss wasn’t really sure what he wanted for this role either. It was all a just a slow walk through thick weeds, not that interesting and kind of annoying. I think they ended up going with an internal candidate? Whatever it was, they posted a job description that didn’t match what they were looking for, they didn’t have any sense of direction, and they failed to pique my interest even once.

The Winner! The company that ended up being a great fit wasn’t perfect. They had some real issues, widely available publicly before the first call with them. One of their co-founders left in 2015, in 2016 they laid off 25% of their staff, they were entering their 10th year as a startup (that’s a little long in the tooth by startup standards), and they had an ad-based revenue model (read, free to customers), which left people wondering how they were staying competitive. So, when their HR recruiter reached out to me, and I took a look, it gave me pause. That said, I set up a phone call with them, as was my standard (listen to anyone, follow up for good fits), and the journey began.

• HR: I don’t think Brittany Miller will mind me mentioning her name here, because, well, she is awesome. So awesome, in fact, SpaceX recruited her away from Practice Fusion several months after I started. Zero surprise. She was thorough, timely, always followed through, set reasonable expectations, and was transparent. If you are lucky enough to get a call from her, take it, you are in good hands. Great start, next.
• Video Interview: My new boss set up a video interview, and it went pretty well. Note to everyone, video interviews are always difficult. If you look at the camera to convey being engaged, you can’t read the other person’s reaction, and if you look at the other person, you look like you are not engaged. Then, god bless technology, but the minor delays in voice throughput almost always leave awkward starting and stopping points, talking over each other, confusing apologies and “no, go ahead” stuff. Still, the biggest problem we had was figuring out who would take a breath long enough to allow the other person to respond. She talked fast, and I found the right moments to jump and hold the conversation. Solid 2nd phase, next.
• Founder: This is where it gets interesting. One of the founders video interviewed me next. When he came on screen he had a purple mohawk, a tie dye t-shirt, and was sitting on a bean bag. UH OH! He explained that this was the once-monthly “phenomenal Friday”, a Practice Fusion tradition that blends company update, charity and education initiatives, and happy hour. That day’s theme was celebrating the anniversary of the Summer of Love. He was engaged, spoke my language, and understood what building a customer-centric organization was and why it is so important. I gave as good as I got and found out later that he was in my corner from that call forward. Rounding 3rd, headed for home, next.
• On-Site: I lived five hours away, by plane, from their office, so there was some challenging coordination, but they bought my flight, put me up in a hotel, and scheduled an all-day marathon interview. Normally, that would be irritating, all day marathons are hard, but I had one shot with everyone, and would be taking over 35 staff, so it was understandable given the circumstance. Let the grilling begin. I spoke to directors and VPs across the organization, and with the three managers that would be reporting to me. We took a brief break for lunch, and then I presented on a couple of use cases for about 10 people that they had given me in advance. They poked and prodded, challenged my reasoning, asked pointed questions, and I’ll be honest, it was the best interview I had given to date. It was also the best interview I had received! I wanted this job, I loved the culture and the product, I was excited, and I got a solid read on the players in the room and their motivations. I nailed it and they did too.

The rest, as they say, is history. I sent follow up emails from the airport that night to each and every person I met with, tailoring them to our conversation and expressing my excitement. I spent a significant amount of time composing the message to my three direct reports, the managers, leveling with them and acknowledging the awkwardness of interviewing your potential boss, and what I would do to contribute to their success. I got a call the next day, and an offer the next week, accepted the role and made my way to California to start my new job. And then, all hell broke loose…

Patience, good readers. That was a lot to sift through for you and for me. I legitimately got excited just now talking about the cycle that got me from seeker to finder. So much more to come!

Next time, the leaving and the arriving. I’ll cover the end of an era and the beginning of the roller coaster ride I am on now in the next installment of THAT STARTUP LIFE.