M2YL — Objective, Critical Thinking of People (Pt. 3)

How I started thinking critically of other people in an objective, productive and healthy way

Note: This is part 3 of a series of posts talking about my experiences and learnings the last two years. You can find the rest of the series here.

One of the hardest things I had to overcome was my fear of stepping out of bounds or making someone feel bad. I was raised to respect authority and to always do what you can to help the family. As I grew older in life, “family” included my friends, teams and coworkers. That desire to put the team/company first helped me in my career; I was able to develop meaningful relationships with my coworkers which enabled me to make impact beyond just writing code.

However, this is also a weakness in that I have a hard time having critical thoughts towards other people, even in private settings. Once I transitioned into management, I was put in a lot more situations where problems weren’t binary and technical but they involved other people, whether it’s another engineer, a fellow peer in another department, my direct manager or the CEO. For these kinds of problems, the solution isn’t something that I have full control over but instead requires some kind of behavioral change in others.

As a manager, one of the primary responsibilities is to remove blockers for the team. That meant that I was responsible for identifying the root cause and dealing with organizational problems within my sphere of influence. In most situations, problems occur because there’s a gap in resources. That’s a easy problem to solve because it’s binary: more resources means more bandwidth for productivity and less resources means more unhappy people across the company (especially the engineers who became the whipping boys/girls). However, the other category of organizational problems revolve around gaps within a person or a group of people, whether it’s with technical knowledge, communication or soft skills. In my first year being a manager, the values I was brought up with unconsciously clashed with my responsibility of giving feedback to others — especially to people higher up in the organizational ladder.

One day I was venting to a mentor of mine about a certain problem I was brushing up against at Teespring, and she said that it sounded like there was poor leadership at the top. I was quiet for a moment, and then my first response was to defend my company and dismiss the idea that somehow I was working under poor leadership. She then objectively laid out her case that the conflict I was facing was a result of the leadership team saying one thing but their actions saying something completely different. Once I absorbed what she was said, she then asked me,

“John, do you realize that you had trouble having critical thoughts towards your leadership team?”

That was an eye-opening experience for me. I was unaware I had a hard time having critical thoughts towards others, even in a private conversation with a person I trusted. My desire to defend the leaders of my company blinded me from seeing that they had areas they could improve upon. I realized that as a manager I could play a role in influencing my superiors to do better.

Over time, that same mentor coached me into understanding that there’s a difference between having critical thoughts towards others and being critical to others. Having objective critical thoughts towards people is important in not just for your own emotional well-being, but — when applied appropriately — it will help solve organizational problems in a more effective way. Being critical to others, on the other hand, is something that’s shunned not because we as a society want to avoid sharing feedback but because historically people deliver critical feedback poorly, which makes the other party quietly feel marginalized or humiliated. I think we can all agree that receiving constructive feedback[1] is something we all seek. But even if we all had the ability to deliver that feedback effectively, it wouldn’t matter if we didn’t have any critical thoughts to begin with. Having objective critical thoughts is the foundation for any kind of meaningful change.

So what does it mean to have objective critical thoughts? You can make an argument that no thoughts are truly objective, since thoughts are formed through our own personal lens of prior experiences and upbringing. However, there is a process where we can ground our critical thoughts to facts so that they’re as objective as possible. As with many other things, having good judgement isn’t an inherent ability but a skill that can be developed over time.

As an engineer, I naturally gravitate towards math and science, so the way I see this process of forming objective critical thoughts is very similar to the Scientific Method: we first must observe the situation, create a hypothesis, gather data (i.e. email/Slack, JIRA, interviewing key individuals), analyze the facts and finally decide on next action steps. The most important thing in this process is to hold off casting any judgement until the very end. As humans, we have many kind of cognitive biases where our brain can quickly draw conclusions even though it may not be true. When dealing with other people, drawing a wrong conclusion too early can lead to devastating consequences i.e. ruined working relationships or personal credibility.

Additionally, I’ve found it useful to share my findings with someone I trust (like having scientific research peer reviewed). Even if I did my due diligence in my fact gathering, it’s possible that my analysis was based off of a wrong perspective or I missed some key information. That said, make sure to do your due diligence first and gather all the facts. Everyone will have their own cognitive biases, so it’s important to ground ourselves to the facts.

It’s important to ask yourself throughout this process: could I have done something different to make the situation better? In Jocko Willink’s and Leif Basin’s book Extreme Ownership: How U.S. Navy SEALs Lead and Win, they talked about how that in order to create a culture where people take full ownership of their actions, the leaders must take full ownership of failures, even if it’s directly caused by someone else. When drawing conclusions and thinking of next steps in this process, it’s important to also think of things you could have done. Maybe you could have been clearer with your expectations much earlier, or maybe you can make the work environment less stressful so morale can improve or maybe you can work with the right teams to develop additional tools or training to prevent certain bugs in the code. Reflecting on how you could have done more for the other person will not only be appreciated by the other person, since it shows you’re genuinely interested in improving the situation and not wanting to blame others, but more important it also will help ground you so that during the stressful moments of delivering feedback you’re coming from a place of compassion and not from anger.

There are still times when even after going through this process to develop objective criticism, I would still feel that knot in my stomach knowing that I have to deliver constructive feedback. But every time I notice that I’m hesitating in giving that feedback, regardless of whether it’s to someone on my team or one of my superiors, I try to remind myself of these key principles:

• Constructive feedback will not only help the team/company, but more importantly it will help this individual grow in his/her career for the future.
• If you frame the feedback so that it’s coming from a place of growth and support and less about blaming and attacking one’s character, the person will always be more grateful in the long run than if you had said nothing.
• As leaders, it’s our duty to take ownership and try to improve the situation instead of letting it fester. If you see a bug in the code, you don’t just say “Ah I’ll let our customer report it first before I’ll fix it.” So why would you act differently when you see a “bug” in other people?