More Questions Than Answers — The Boss Who Taught Me Everything He Knew

More questions than answers is a mindset I carry that I attribute to my first boss, Gary Tighe. Some people thought Gary was an asshole because of his inability to tolerate what he considered to be stupidity, and the crude way he responded to peoples questions or work. His lack of empathy led to a lot of watery eyes from the men and women that worked for him over the years. But despite that, Gary really was a good guy.

Fresh out of college I started working for Gary and he reluctantly took me under his wing. The prior summer my brother had worked for him for a few weeks before bailing on the job without notice. One day he decided he didn’t want to work there anymore, and he just stopped showing up, which prompted a phone call home from the admin office to see where he was. So when I started working for Gary I was unknowingly operating from a deficit. I think he was quoted as saying “great, another Alvarez.” (I only learned years later that he said that)

On many occasions in those first few months and years of working for Gary I was on the receiving end of his explicit and vulgar responses, in which I was told to leave his office after he explained all the ways the analysis he asked for was moronic. But being an empath, I knew he didn’t mean anything personal by it, and that was just how he communicated. His choice of words reflected his inability to comprehend the work of someone lacking his level of intelligence. I think he was often genuinely confused as to how he could ask for one thing and I could produce another. I was also thick skinned, and confident in my ability to figure shit out, so I just brushed it off again and again, and went to my cubicle to make the changes. But even if he wasn’t always happy with my performance, Gary was good to me, and took care of me, the same way he did all of his employees.

Because despite his reputation for being short and crass with his employees, he also made it clear that he supported them and had their back. He never tried to screw anyone out of their raise, and often advocated for bigger increases for his employees. He never denied anyone a promotion who was deserving of it. He never told anyone they couldn’t take time off, and he actually encouraged his employees to do so (even though he rarely did). He never tried to take anything from anybody, and, to me, that’s the true measure of a good person. Which is what Gary was.

The reality is I also recognized early on how smart and knowledgeable he was when it came to business, finance, and life more generally, and I saw it as such a gift to be able to learn from him. I would always say work was like a paid education. Because straight out of college I didn’t know shit. It seemed like nothing I had learned in those four years applied to the work I was doing. And he taught me everything he knew in those five or so years we worked together. He also, unknowingly, helped coach me through some tough choices in my early 20s.

Of all the things I learned and observed from Gary, there are two distinct things that I remember him saying that have stuck with me ever since, and to which I repeat to this day. 

In 2014 or so I decided to move out of my mother’s apartment where I had been living since graduating college in 2009, and buy my own place a few blocks away. I was trying to figure out how much to offer on the one bedroom apartment I was interested in. It was this really great first floor, corner apartment, with multiple windows in every room that brought in great light throughout the day, in an old brick building close to my family and to work, and I didn’t want to lose it. 

They were asking I think $150,000 - $160,000 (somewhere in that range). At the time I had just enough money for a down payment, at 20%, and the closing costs, so I was trying to be really strategic about what I offered and ultimately agreed to, so I could have some money left over for some upgrades and renovations that the apartment sorely needed. But I also didn’t want to embarrass myself with a lowball offer, and make it appear as though I wasn’t serious.

I had asked my grandfather, a WWII veteran and depression era baby, how much to offer and he said something like $80,000. I knew his cut the price in half tactic had worked many times for him throughout his life, but it was a different time from when he was wheeling and dealing real estate, and I didn’t think it would fly in my situation. I was confident that an offer that low would air me out to dry, and cause me to lose the apartment. I told Gary about it one day, and asked for his advise. I said I was afraid an offer that low would offend the seller. 

Gary leaned back in his leather desk chair, folded his arms over his belly, and stared straight through me. After a long pause he said, “They’re not your friends. If they accept your offer you’re going to shit your parents and wish you went lower.”

I think I offered $100,000, and landed on $120,000. I think I got a good deal (I sold the apartment a few years later for almost double the price) and I didn’t shit my pants.

One of the projects I was assigned early on was to reconcile our companies billing and payments for certain high ticket procedures. In healthcare whenever a procedure or service is performed there is a corresponding CPT (Current Procedural Terminology) code that needs to get billed to the insurer so they know what to pay. How you bill that code determines how you get paid. Units, charge amount, and modifiers (which provide further information about the service) must all be correct to receive the right amount. Reconciling payments is a tedious job, and as the young entry level analyst this task was assigned to me.

But running reports and analyzing billing was the easy part. As a 22 year old new graduate the hard part was taken the analysis and questioning the people responsible for the errors and inconsistencies I found, which often resulted in a substantial amount of underpayments from the insurers. When I told Gary about the nerves I was feeling about asking colleagues who were 10 - 30 years my senior about their work, he replied calmly and said, “Just ask them about their job. People love to tell you about what they do.” He went on, “Ask them questions about the reports. Don’t assume you know the answers. I don’t know all the answers, but I know what questions to ask, and that’s more important anyway.”

It was kind of a monumental moment in our relationship. Here was this successful and highly intelligent man admitting that he didn’t know everything, and in fact, in a way, he was proud of it. Because he knew that as long as he knew what to ask, he figure it out eventually.

I remember the first time I ever noticed Gary put this on. We were in a meeting with two guys who were lifelong friends of our CEO, being pitched an opportunity to invest in their healthcare adjacent startup. Given the relationships, this meeting was meant more as a formality than an actual pitch. We were going to do the deal regardless of the plan, and Gary knew this. But that didn’t stop him from peppering them nonstop with questions, and relentlessly punching holes in their business plan where most people would have just nodded and said ok. And this went on for over 2 hours. As a young kid watching these two grown men squirm and stammer as they struggled to respond made me so uncomfortable, and at the time I honestly couldn’t wait for the meeting to end. 

But as uncomfortable as I was I was also amazed at Gary’s ability to pelt them with question after question, and his willingness to sit quiet as his questions hung in the air awaiting an answer. After that meeting I began to notice it more and more and realized what an important skill it was to have. It’s a skill I’ve been trying to hone ever since. The mindset of more questions than answers grew out “I don’t know all the answers. But I know what questions to ask.”

I owe a lot to Gary. Despite being “another Alvarez,” he gave me a fair chance and was happy to teach me everything he knew, recommend me for raises and promotions, and transfer his knowledge to me (which is not always an easy thing for people to do, but is another sure sign of a good guy). And to this day I use so many of the lessons and perspectives he taught me.

Gary left the company a few years before I did, and died a few years after that. I never got to thank him for everything he taught me and did for me, and it still makes me sad to this day. My hope is that this post helps bridge the sadness I feel about never getting to tell him. Rest in peace Gary.