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Writer's pictureCraig Whitton

Sunday Story: Black and White Thinking and how to Criticize Kindly

This Sunday Story is inspired by one of my most treasured friends - what started out as a pairing via my former employer’s mentorship program has blossomed into a relationship that I count as one of my most valued. Long after the end of that mentorship program, we’ve continued our regular chats through the highs and lows of life for years now. Our conversations have covered a lot of ground over this time, and I could write an entire blog series just on the things they have taught me through our conversations - no doubt I’ll be crediting a lot of future Sunday stories to their inspiration also, but this one is from our most recent chat on Friday.





What do you think about when you consider black and white thinking? I’m going to bet that it draws conclusions of folks with unchanging beliefs; they support their candidate as a god-fearing Christian even if all evidence is to the contrary, or they believe their candidate is a bastion of social progress even if they’ve got a track record of lining the pockets of corporate buddies at the expense of everyday working people. Or maybe it’s religion, or attitudes towards sex and sexuality, or any number of other issues - the concept of “Black and White Thinking” tends to conjure up people with unchanging and uninformed opinions on things, usually along the lines of “I’m correct, and since you disagree you are wrong”. We see this division play out in real time on social media (which is mostly fake outrage these days) where despite humans having so much in common, our media tends to encourage us to focus on that which divides us instead of unites us.


I am a black and white thinker, and so is my friend - but it’s not in the way you may have envisioned things as described above. There’s another type of black and white thinking, one that is core to values-based leadership, which as I’ve written before is essential to being able to lead during disruptive times and make them transformative instead.


This black and white thinking is hyper-analytical. It’s about absorbing as much information as possible, reading, watching, and understanding. It’s about using empathy to understand “Why does this person think the way they think?” - even if they are in a position that is polar opposite to mine, one I might find distasteful or even horribly wrong, it’s not about dismissing those perspectives - it’s about deeply understanding them, understanding how the person arrived at that conclusion (if that’s possible), and the end result is being better informed about the issue at hand. This is the analytical approach I’ve applied to our “Briefing Notes for Average People” that I’ve published to help you wrap your head around some of the most significant disruptions our society faces today, from the housing crisis to UAPs.


Generally, the result of this hyper fixation on information allows me to reach conclusions, and those conclusions are where I’m a black and white thinker. The evaluation of data and information results in what I feel is the most obvious conclusion, and that conclusion is as stark as “black and white” - critically though, the key thing here is that when presented with new or different information, both my friend and I are willing to change our minds. For me, that is a lesson I learned from a Student Affairs leader named Pam Schreiber, an incredibly accomplished human who probably doesn’t even remember dropping this pearl of wisdom, but I remember it like it was yesterday. It was at NWACUHO - the Northwest Association of College and University Housing Officers - annual conference during a small breakout session where a half dozen new professionals like me could ask questions of a senior housing leader. Pam said “Never forget that it’s always OK to say ‘My thinking has evolved on that’”. It resonated deeply with me - when we know better, we can do better, but that only works when we are willing to adopt and adapt to new information as it comes to light.


So, my thinking is black and white, but only after an exhaustive review of the information; I try to assign a degree of confidence to my opinions based on that review. If I’m only familiar in passing with something, I’ll say so. If I’ve done a deep-dive into something, then I’ll confidently state what I think. And if new information comes to light - as it always does with the continual march of human progress - I’ll say “My thinking has evolved on that” and adapt accordingly.


The black-and-white thinking comes in when I consolidate the evidence and data with my values. After a fulsome review, it’s often pretty clear on what the right or correct thing is from my perspective, but that’s a key component here too - it’s about _my perspective_. And that is fundamentally shaped by my values, as it is with all leaders. A leader who values profit for shareholders above all else will have a very different approach to the exact same data and information. That’s OK of course - that diversity of thought and perspective contributes greatly to that same march of human progress I mentioned earlier - but a leader who isn’t clear on their values may find themselves engaging in black and white thinking that’s inconsistent; they review the information and data today and reach one conclusion, and then in a substantively similar situation with similar information and data they may reach another conclusion. That creates disruption for the people they lead, because they cannot predict what their leader is going to do next and that unpredictability leads them to trying to guess - often incorrectly - what comes next. However, a leader who is able to assess information, and articulate clearly what the right or correct thing is, in the context of consistent values, will find that those they lead are able to guess what they are going to say. That builds trust, safety, and helps avoid disruption (or make it transformative instead).


A key tool in my approach to my black and white thinking is actually the work of one of the greatest modern philosophers who just recently passed away in April of 2024: Daniel Dennett. Mr. Dennett articulated a technique on how to criticize kindly, and I think it’s a lesson we can all learn from in our modern world full of disagreement. He summed it up as being about four steps:


1) You should attempt to re-express the opinion of those you disagree with in such a clear and articulate way that they say “Gee, thanks - I wish I thought of saying it that way”.


2) You should identify any points where you agree with them - even in the most polar opposite of viewpoints, there are elements of agreement that one can find.


3) You should mention anything that you’ve learned from them; I call this being “Source agnostic”. Even if you fully disagree with a person’s position, they can probably teach you a thing or two about how they got there, or that you did not know before.


4) Only then do you rebut or critique their position. I put a twist on Daniel’s approach by saying - do this with questions. If you tell people what you think, they are going to tune out and someone that could be an intellectual ally can instead see themselves as an opponent. But if you ask them questions about their position as a form of questioning critique - also known as seeking first to understand - you engage their brain in the process of figuring things out. From there, they will either explain things in such a way that answers your question and helps your thinking evolve, or they’ll be forced to think themselves into new conclusions that helps their thinking evolve. That’s a win either way.


Because remember, it’s always OK to say that your thinking has evolved on that.


I’m incredibly lucky to be able to engage in black and white thinking with my friend; we ask each other questions, we challenge each others’ positions and beliefs; we digest scores of information and share books, documentaries, articles, and other resources to expand our knowledge, and we reach conclusions that align with the values we hold as the people and leaders they are. One final thing for this Sunday story - I’m going to ask you to do something, which I have never done before: If you are so lucky to have a friend like mine, someone who makes you a better person just by being in your life, grab your phone (or open up your messaging app when you’re done this paragraph) and send them a text. Tell them the impact they have on you, and how grateful you are for it. I know my friend will be reading this, and it’s my way of doing it - and we don’t say it enough, but friends like this are a rare and wonderful thing that should be treasured. I’m eternally grateful for my friend, and I know you all have a friend like that too - so tell them.


That’s it for this week - we’ll see you next Sunday.

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