Ideas

Dismissively Stubborn

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The only type of colleague I refuse to have is a dismissively stubborn colleague.

Dismissive stubbornness is the kind of stubbornness where someone does not engage with your argument. They ignore it completely, as if it wasn't even articulated; you can sometimes see it when it appears that they've not listened to you, or when they parrot the same arguments repeatedly, resort to ad hominem attacks, or — if they possess good social skills — when they misdirect the discussion using humour.

Here's an example. Consider the argument: “Don’t put that bucket of water on that ledge by the servers, someone might knock it down as they pass by.”

Dismissive stubbornness shows itself in how people respond to arguments. In this example, a response that isn't dismissively stubborn would be “it’s only going to be here for 5 minutes”, or “the odds of someone knocking it down is low since nobody comes here anyway”. Notice that there’s an implicit acceptance that spilling water on servers are bad.

A dismissively stubborn person’s response, on the other hand, would be to ignore the argument and its implicit assertions entirely: “I want to put it here because it’s closer to the flowers right outside the server rack.”

This is the root of some extremely unproductive, frustrating arguments.

You: “But if the water falls, we’d lose $20k worth of servers and potentially a week of downtime!”

Them: “I want to put the bucket here because I’m tired of always carrying the bucket of water up from the toilets.”

You: “It’s too dangerous to put it there, why not put it downstairs, near the stairs instead?”

Them: “That’s still too far. I’m sick of carrying the bucket that far.” And on it goes, in circles.

You might think that this is a ridiculous example, but this illustration contains all the elements of a dismissively stubborn person. The argument circles unproductively. Both parties talk past each other, due to one party's persistent refusal to engage with the content of a particularly strong argument.

Here's another example. Designer Dave is working with Dismissively Stubborn Stuart, who's the software engineer for an internal website redesign.

Dave: “We did the user test. Ten people were confused when presented with design A, but none were confused when presented with design B. Therefore we should adopt design B.”

Stuart: “That's interesting, but I think design A is more consistent with the look of the company.”

Dave: “But our user tests show that it's not usable!”

Stuart: “Well, I showed it to Bob. He thought that design A looked better.” (Bob is their manager, one level above in the company).

Dave: “I'm sure Bob would prefer it if we built something usable. We can bring it to him if you like. But this doesn't detract from the fact that I don't think it's a good idea to choose design A — people get confused when so many buttons are displayed on one screen!”

Stuart: “I think Bob would disagree with you. Besides, design A is easier to implement, and will take less time.”

Dave (frustrated): “I'm not sure you understand. Design A. Is. Not Usable.”

Stuart: “Why are you shouting? Can't we just have a reasonable discussion, like adults?”

Notice how Stuart raises valid but incidental arguments, none of which engage directly with Dave's core point. Dave quickly gets frustrated because he's talking past Stuart. This is no different from the earlier example with the bucket of water. The only difference between the two examples is that in the former, the argument contains no data. In the latter, the argument is significantly stronger due to the results from a user test. But even in the presence of data, a dismissively stubborn person is able to persist.

*

I cannot work with dismissively stubborn people. This is not a new realisation; it’s an old one, but I've only recently distilled the problem down to this specific type of stubbornness. My approach has historically been to kick such people out of my organisation if possible, or to minimise the damage they can do if I couldn't. At my last company, I spent a period of six months iterating on our hiring process, in an attempt to catch this sort of stubbornness early. It wasn't good enough. Three people got through; I fired one subordinate on probation and the other two quit within two to four months, to everyone's relief.

This is a pretty charged paragraph, so I want to colour it in. Provide nuance.

One of the most important qualities I look for in a colleague or subordinate is whatever property it is that’s the opposite of dismissive stubbornness. Call it 'flexibility of thought’, if you will. What I mean by this is the behaviour where you adopt my position whenever it is clear my argument is the better one. In return, I promise to hold myself to the same standard: if you present an argument that is clearly superior to mine, I will adopt your position as quickly as possible. Or to put this concisely: we are interested in ‘getting things right’, not ‘being right’.

This is especially important if you are in a startup, where there are limited seats on a team.

Dismissively stubborn people are the worst possible way to fill seats on your team. You can't reason with dismissively stubborn folk, because they have no desire to face the reality implied by your argument. You spend large amounts of time arguing with them, going in circles to get them to see your point of view. Very often they would resort to political means to win — I've known one to say “why do we always have to do things your way?”, and another to say “why can't you trust my expertise?” ... as if these objections addressed whatever argument was presented to them.

I am not the only person to have noticed this property. Paul Graham writes, in A Word to the Resourceful:

A year ago I noticed a pattern in the least successful startups we'd funded: they all seemed hard to talk to. It felt as if there was some kind of wall between us. I could never quite tell if they understood what I was saying.

I'd wager that this property that Graham notices is exactly the same one I'm calling dismissively stubborn.

*

The Oxford English dictionary defines stubborn as “having or showing dogged determination not to change one’s attitude or position on something, especially in spite of good arguments or reasons to do so.”

This seems like a reasonable description of ‘dismissively stubborn’. So why is it necessary to invent a new term? Why not just say ‘stubborn’?

The reason is that some forms of stubbornness are acceptable.

Say for instance that you engage with the objections of another party instead of dismissing them, but remain unmoved in your overall position. By the Oxford dictionary’s definition, you may rightly be called stubborn. After all, arguments that appear compelling to the other party have not moved you. But perhaps their arguments are not compelling to you because you start from different assumptions. You are not dismissively stubborn, as you have taken the time to engage and understand your counter-party’s arguments. But you remain justifiably stubborn ... from their perspective.

A concrete example suffices. Earlier this year, I was part of a startup incubator program in Singapore, where one of the conditions for getting funded was that I formed a team with another member of the cohort. I formed a team with a fellow member, and took a stab at a passion project I had in university. When my team was broken up, I declined to form another team from within the cohort.

I was told — indirectly — that I was being stubborn; that forming a team would result in a non-zero probability of success, whereas not forming a team would result in my failing out of the program. From the perspective of the investment team, I was being stubborn — and justifiably so! Their arguments made perfect, rational sense.

But I was starting from a different set of axioms. I wanted to cap my downside before doing a go-big-or-go-home startup. So it didn't make sense for me to form a team at this stage.

If you think about startups deeply enough, one of the non-obvious things you realise is that the best route to success is to take repeated stabs at doing a startup. This results from an expected value calculation: the odds of success for a startup are low. Most companies fail. But one success is enough to wipe out your losses.

This means that the optimal approach is to do a combination of three things: to increase the number of bets you make over the course of your life, to increase the odds of success per bet, and to reduce the costs of taking these repeated bets.

Before the incubator program, my strategy was to extend my runway by starting a small SaaS company, one that would generate revenue independently of my efforts. This would extend the number of bets I can make over the course of my life considerably.

I had two years of runway saved up in the bank. With this money, I could take the time to do what is called a ‘MicroISV’. The odds for success are better. When your goal is revenue, you have more options available to you to make that happen. When you have to make a 10x return on investment in a venture-funded company, your set of moves shrink considerably. I saw this first-hand: once as an intern at Viki, pre-acquisition, and then as an engineering lead in a small, non-funded Singaporean tech company. The latter made it to 4.5 million in annual revenue before I left.

The incubator program wanted me to form a team because it could make a bet on my effort. But it didn't make sense given my life goals. If I were going to take a stab at the go-big-or-go-home startup, I would feel a lot better having my downside capped before I started.

I was stubborn, but I wasn't dismissively stubborn. And I think that's ok.

*

I've attempted to describe this property of stubbornness to a bunch of my friends over the years, and I've heard an equally diverse number of plausible causes. One friend has argued that a person becomes dismissively stubborn when they feel insecure. A few others subscribe to the more popular theory that it's ego that causes this behaviour.

I'm not so sure either cause is accurate. Not all the dismissively stubborn people I've dealt with have displayed fragile egos. In fact, the strongest anecdata I have against this is that I actually tried to filter for ego and insecurity in my previous company's hiring processes: I mandated that all interviews include a component where an interviewer would gently probe a mistake that the candidate has made. Any aggressively defensive candidate would get an instant ‘no-hire’ decision.

It didn't work: while it caught a couple of candidates, a dismissively stubborn engineer still made it through our process half a year later.

I should note that dismissively stubborn people aren't stupid, by any means — one of the most dismissively stubborn people I've met was amongst the top of his university cohort. Graham's essay has something similar to say about smarts:

Chasing down all the implications of what's said to you can sometimes lead to uncomfortable conclusions. The best word to describe the failure to do so is probably "denial," though that seems a bit too narrow. A better way to describe the situation would be to say that the unsuccessful founders had the sort of conservatism that comes from weakness. They traversed idea space as gingerly as a very old person traverses the physical world.

The unsuccessful founders weren't stupid. Intellectually they were as capable as the successful founders of following all the implications of what one said to them. They just weren't eager to.

Graham attributes his difficulty in talking to bad founders to a lack of ‘conversational resourcefulness’. He argues that bad founders weren't resourceful in chasing down all the implications of advice the same way they weren't resourceful in chasing down funding, and users, and sources of new ideas.

But I don't think that's accurate. I think this behaviour could be better explained by a strong desire to hold on to a preconceived notion of the world. Successful people update their models of the world when they encounter failure or pain, or strong counter arguments. Unsuccessful people refuse to engage in anything that diverges from their model of reality.

If true, it implies that there are more powerful reasons to avoid working with dismissively stubborn people than everything I've mentioned thus far. Holding too tightly to a calcified model of the world means that dismissively stubborn people will plateau beyond a certain level. Their personal evolution has stopped. Their skills can only get them so far.

Your best bet for early detection is — like Graham — polite debate. When you find yourself talking past someone in a friendly discussion, you should begin to wonder if you're dealing with someone who's dismissively stubborn.

I have to admit: my bias is that I genuinely believe dismissively stubborn folk are incompetent. I think that their inability to adapt to the realities of the world results in suboptimal decision-making. I know they're a pain to work with. But regardless of whether it’s caused by insecurity or ego or mental models, I find it too difficult to help them improve — or at least too difficult in a professional context. My inability to deal with them is a weakness, perhaps. Whichever it is, one thing is clear: I avoid them like the plague.