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November 2018
January 2019

2018-12-02 »

Don't delegate the most important thing

A while ago I was discussing hiring plans with a co-founder of a recently-funded startup. Their story was something like this:

"The company is growing very fast and we now have about a dozen people. We have tight deadlines, and none of the founders has much experience in project management or people management. So, we're trying to hire an experienced project manager and an experienced engineering lead / people manager."

This course of action is pretty common. It also always makes me nervous, but I haven't thought much about it until now. This discussion finally forced me to clarify my thoughts on the subject.

First of all, I asked the co-founder what their role is. The answer was a good one, albeit vague, as startup roles always are: "I don't really know. It's frustrating that I never know. But I do know my job is whatever it takes to make the company successful."

Well, what are the most important problems that the other co-founders aren't solving? The answer came quickly: "We don't have a clear idea of our project schedule. And nobody is managing interpersonal, cultural, social issues. There are lots of other problems, but people are handling those." So those were the top two. Nobody was managing those, and it was getting serious.

This reminded me of some advice I must have heard somewhere, but no longer remember where: Don't delegate the most important thing. Or maybe it was a 1980's management book: Don't outsource your core competency.1

This advice is counterintuitive. At first glance it sounds like it should be intuitive, but once you think about it, it's not. The most important thing - whatever it is! - needs to be done well. Shouldn't we hire the best person possible to handle it? And isn't it vanishingly unlikely that the person already works here?

You're right! In an ideal world, you would get the best, most motivated, most passionate project manager in the world to manage your project. And the best, most motivated, most empathetic, most wise people manager to manage your people. But the real world is rarely ideal. You are unlikely to find the best person in the world on short notice. You probably can't afford to pay them what they deserve. In a wide world where they have their choice of exciting projects, they (statistically) probably don't care enough about your project anyway. And because they're so good, they're probably accustomed to leading huge teams with huge problems that need huge solutions.

In short, you aren't likely to hire the ideal person. You can probably hire a pretty good person. Or you might get unlucky and hire a terribly mismatched person.

That variability is a huge problem. Even if the average person you could hire might be better than you, the standard deviation is very high. It's essentially a random chance, a lottery ticket. Do you want to buy a lottery ticket for the (self-selected) most important thing in your entire domain, whatever it is?

The alternative is to find a person with less specific expertise, but who can understand the company vision, connect with everyone on the team personally, be highly invested in the shared outcome (not just personal gain), and be so passionate about the project that they'd be willing to step aside if they can someday find someone who is a better fit. As a bonus, this person already works at your company: it's you.

Relatively speaking, it's actually pretty easy to learn project management and scheduling or people management. It takes time and effort, but not much more, to become passably decent at either one. Whereas you can't buy shared vision, personal knowledge, shared motivation, or humility, for any amount of money.

Once the schedule or the management of small teams is no longer your most critical problem, then delegate those. Better still, by then you will know how to do the jobs, so you will be very good at interviewing your replacement.


1 "Core competencies" is one of those once-useful terms that has been badly diluted through overuse. It mostly just means "things that uniquely make you special compared to your competitors." If you're a software company, that's probably your software.2 So buy some commodity package (or service) to do your accounting, which doesn't differentiate you, and hire people to write your software, which does.

2 Even at a software company, sometimes your software is crappy and your customer service or sales organizations are your real advantage. Confusion about this has led to horrible strategic blunders. IBM's core competency, for example, clearly is not software.

2018-12-08 »

Honourable Governance

From a book I've been reading:

    Power is certainly important, particularly in dictatorships, in places where constitutions, laws, unwritten rules, traditions and understandings don't count. But in a healthy democracy, power is a surprisingly limited element. And the unwritten conventions, understandings, forms of respect for how things are done, for how citizens relate to government and to each other, are surprisingly important. Why? Because if democracy is only power, then what we are left with is a system of deep distrust. Why? Because if only power matters - even if it is the result of an election - then the government feels that it has a mandate to do whatever it wants, that the law is there principally to serve power. If democracy is only about winning power and using it, then it has been deformed into a denial of society and of the idea of responsible citizenship.

    And that is the increasingly common characteristic of government, even in democracies. Only power matters. This is partly the outcome of government being de-intellectualized. Elections are now thought to be unsuitable moments for real debates over ideas. In between these elections the focus is on administrative problems - legalistic, managerial undertakings. In this case, real debates over ideas are unnecessary because the decision about power was taken on election night. There is nothing, therefore, to debate. Worse still, the efficient putting in place of programs to be administered can only be made inefficient by debate.

    And so we are witnessing a growth in the Napoleonic or Mussolinian corporatist idea that when citizens vote in an election, it is actually an all-purpose referendum or plebiscite. It is then the winner's job to get on with running things. First win an election, then administer as you wish. Omnibus bills are one of the ways you can speed things up; they are a great way to convert the deeply inefficient process of democracy, with all its thinking, debating and complex differences of opinion, into a sort of shop-floor system of utilitarian efficiency. Therefore, once elected, a government has broad, unlimited permission.


    In any case, today's plebiscitary approach is both populist and anti-democratic. What it amounts to is this: We won the election. We have power. It is now a matter of administrative efficiency. We can do what we want.

        - John Ralson Saul, The Comeback, 2014

This finally put into words a concept I've been struggling with for a long time: the idea that ethics and responsibility come with (should come with) political power, and how they seem to be on the decline lately.

For example, I recently learned, to my horror, about the concept of a Frankenstein Veto, where in some U.S. states, the governor can just delete words (eg. "not") from a bill passed by the legislature, producing and then approving a bill with a completely different meaning than was intended.

The exact legal machinations of this are beside the point. The point is, politicians increasingly feel that they "first win an election, then administer as you wish." That almost sounds logical, so why does it feel so wrong?

Because it is wrong. The job of an elected official isn't to do whatever they want. It's to figure out what the people want (or need), and to deliver that, in accordance with principles and ethics. This is a surprisingly selfless expectation: sometimes the right thing to do is the opposite of what you want to do. And it can be hard to figure out what's right, which is why we have debates, and why we listen to our opponents in those debates, even when we have a majority and they're "merely" the opposition.

Even direct polling on issues doesn't always work, because sometimes issues are too subtle for the population to simply vote yes or no; that's why we elect representatives who will presumably do their homework, consult the right people, and figure out the right, complex answer. At least one thing is clear: if the legislature vigorously debates an issue and decides one thing, a governor passing a law that does the opposite - or even rejecting the one that was so carefully produced - is just not right.

I've been struck many times by the way the U.S. system of political "checks and balances" treats politicians like children: none of them can be trusted, so we must restrict them at every opportunity. The underlying assumption is that they will all operate without honour. As most of us eventually learn in our human relationships, if you treat people as children - or worse, as actively malicious adults - then they will tend to meet your expectations. The great irony is that in countries with less of a focus on checking "power" (such as Canada), politicians seem to abuse their power less often and less dramatically.

The above quote made me think that maybe the secret recipe is some combination of traditions, conventions, understanding, and respect. Maybe those are more effective balances to power than any system designed to simply neutralize it. And maybe this was obvious to the people who designed it, and we've forgotten, long ago.

November 2018
January 2019

I'm CEO at Tailscale, where we make network problems disappear.

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