Head of People

Strategy is better than conflict.

An employee goes to their boss and complains that they need a raise, don’t get to do the projects they want, and doesn’t feel in general like they have the resources they need to succeed. The employee is a great asset to the team, and overall likes their workplace, but these things are becoming a problem for them. They don’t want to quit, and the boss doesn’t want to lose them.

But it’s already a conflict! These things need to be resolved, and there’s a great relationship under them – but they’re cause for alarm. Yet this is a bad way to address them. It’s already adversarial.

Now, imagine a different scenario:

The CEO sits down with their Head of People for their weekly digest. The Head of People shares some statistics: 45% of employees have made inquiries about different projects than the ones they’re being assigned, indicating a misalignment of workforce priorities. In addition, an unbiased comprehensive salary report indicates that the company is trending behind the market average, which might cause higher turnover in the near future. Because this is strategy-driven, non-adversarial, and unrelated to any specific employee, it allows the CEO to strategize solutions and actually implement them.

The difference is a system that allows the initial “conflict points” to be distilled into actionable strategy. The Head of People (or Chief Culture Officer, or CHRO, or whatever title they have) is an essential part of this system. Their existence alone encourages the team to voice their concerns, and their role is to consolidate those concerns into something actionable.

Everyone gets heard, efficiency is maintained, and a mutually beneficial relationship is enhanced. Win/wins all around as employee engagement and retention skyrockets and the true power of your organization is unleashed.

If you’re not doing something like this in your organization – why not?

Curve Ball

When you find yourself ahead of the curve on something, you can end up doubting the very thing you’re ahead of the curve on.

You look around you and you see no one adopting the new methodology or technique. You see a useful tool laying around unused. And you think: maybe you’re wrong. Maybe you shouldn’t be trying so hard to make this work, maybe it’s not a good idea after all.

Give it a little time. Your early successes will be part of what inspires others. Someone has to be an early adopter, after all. There’s more risk there, certainly. But also greater reward.

What Say You?

Don’t take “verbal shortcuts.” That’s when you want to be thought of a certain way, so you say it instead of being that way until other people say it.

For example: if you want to be thought of as generous, then give. Give until people say you’re generous. But don’t just call yourself generous.

The verbal shortcut is a bad path. It makes people think things about you, all right. But not the things you’re aiming for.

Here’s a good general rule: don’t describe yourself, except to yourself. Talk to the person in the mirror about what you want to be, and be it. Other people will see it and say it – or they won’t. But you’ll sleep a just sleep, and that’s enough.

Head Shot

If you wake up in the morning with a pounding headache, it’s possible that you spent a long night drinking heavily, banging your head to loud music, and crushing beer cans against your skull. Another possibility is that you were minding your own business and an unprovoked lunatic assaulted you with a blunt object.

The thing is, you probably know which one it was. If you wake up with that pounding headache, you probably don’t confuse one cause for the other. You either wake up mad at your past self for a bunch of bad choices, or you recognize that it wasn’t your fault.

That’s for physical pain. We’re really, really bad at that for mental or emotional pain.

Some things are your fault. Some things aren’t. We make mistakes in both directions. We blame ourselves and internalize fault for things that had nothing to do with us. And we blame others (or “the universe“) for stuff that we absolutely engineered for ourselves.

So how do we avoid these mistakes? The very first step is to accept that neither one is automatically true. My observation has been that individuals tend to skew one way or the other. Either everything is their fault, or nothing is. By first accepting the paradigm that individual challenges need to be evaluated individually, you can begin to look for ways to look at your pain in a fair way.


Once upon a time, sawdust was seen as a waste product. An unfortunate externality of the lumber milling process, sawdust had to be discarded in vast quantities. It was burned, buried, or even dumped into rivers.

Eventually, people figured out that sawdust was a valuable product in its own right. It had myriad uses and could be bundled up and sold. Instead of paying to get rid of it, people would pay to take it! The best part: this was pure profit. The sawdust was already being created, and the cost of disposing of it was already baked into the operating cost of a lumber mill. This didn’t just reduce waste. It completely inverted a negative into a positive.

You produce sawdust all the time, and you throw it away.

When you do something for work, that’s the lumber going through the mill. Your boss needs you to write a report for the shareholders this week. That’s lumber. The sawdust is the connection this makes between you personally and those same shareholders, as well as members of other teams within your company that don’t usually hear from you. Instead of doing nothing with that connection, instead of throwing away that sawdust, use it! Send a follow-up email afterward asking for feedback and a coffee chat.

Everything you do produces side effects that you could harvest, but don’t. Tasks you complete can become articles on the associated skills. Projects you finish can become rapport-builders because you complimented your teammates on social media. The beautiful lawn that you landscape diligently can become an equally-beautiful picture to put on a postcard to send to your family.

The point is simply this: don’t waste the side effects. Bundle them up and make them valuable to you, because you’re already making them anyway.

If It Bit Them

It is vital that you think about what you want in a neutral time and space. Before you even have options, you should focus on your desires as an inner conversation.


Because the stuff you don’t want constantly launches itself at you and tries to convince you that you do, while the stuff you do want sneaks up on you and you won’t even notice unless you knew to look.

Think about the old adage, “don’t grocery shop hungry.” If you do, you end up buying nothing but overpriced, flashy junk on the eye-level shelves with colorful packaging. If you’d made a list, on your own, of what you wanted to cook for the week while you were still home, you’d have gone in and found those things, even if they were tucked away.

This is true about everything. People take horrible jobs because they come with a fancy logo on them. They date terrible people who ‘clean up nice.’ They buy impractical, costly cars because of a good sales pitch. All these things happen because you decided to get before you decided what you wanted.

Most people wouldn’t know what they truly wanted if it bit them, so take the time to think about it in advance.

Signing On

People don’t sign things enough. I mean, in general – an artistic flourish, a maker’s mark, a signet stamp, something. But you should be marking the things you’ve done!

There’s a reason artists sign their work. It’s not just for ownership – the artist will sign a painting even when they’re painting it for other people. It’s because your work is a reflection of who you are as a professional, and the more work you create, the stronger of a reputation you can build.

If people know it was you, that is.

But okay, there’s a world of difference between Picasso signing a masterpiece and you signing a slide deck, right? Heck no. They’re both professional creations that you worked hard on, and you want to reap the benefits.

Think of it like this: if Picasso sells a painting for $10,000, he’s getting more than ten thousand dollars. He’s also getting an increased reputation – one that allows him to charge even more for his next painting. He gets more opportunities to communicate with the artistic community.

But if you get paid to make an earnings report and by the time it reaches senior leadership it’s basically anonymous, you’ve missed that opportunity.

Remember what I said about “maker’s marks?” Your signature doesn’t have to be a literal one. It can be anything that marks it as yours. A specific style can become known as yours. A gimmick like a particular animal as a brand. It can even just be helpfully putting your email address in the footer of each page in case anyone has questions.

But make them yours. You work too hard to do otherwise.

One Times A Hundred

A man walked down the street and saw a crumpled-up piece of green paper. Excited at the prospect of finding a $100 bill, he eagerly picked it up and smoothed it out. Alas, it was but a humble $1 bill, so he crumpled it back up and threw it on the ground. He wanted a hundred dollars, not one!

He kept walking and soon found another crumpled bill, but again it turned out to be only a $1 bill so again he discarded it. The route he walked was littered with bills (maybe an armored car had overturned nearby or something?), but they were all ones, so they all got discarded.

This happened three or four hundred times before the man finally threw up his hands and declared “There are no hundred-dollar bills out here! Guess I’m just destined to be poor forever!”

This happens more often than you think. The small opportunities and wins you discard while you’re searching for the perfect solution can add up to what you want. Don’t discard a positive just because it’s smaller than what you want if it’s bigger than what you have.


Jokes can be an incredibly dense information-transfer mechanic. They’re wonderful as a tool to learn a whole lot about a new domain.

Around 15 years ago, I was working in an environment that had, for whatever reason, a lot of hockey fans. I wasn’t particularly interested and definitely didn’t have time to dedicate to learning, but I wanted to know “enough to be dangerous” – in other words, enough to chat with my coworkers. I struck gold one day when I overheard a joke:

“Do you know how to make an Ovechkin? It’s a white Russian but with no cup.” [Cue sound of laughter.]

Now, I said I don’t know anything about hockey, but I know a good joke when I hear one, especially by the reactions. Without having to know anything else, there were many facts I suddenly knew:

  1. Ovechkin is a hockey player, and he’s obviously Russian in origin.
  2. He hasn’t won a Stanley Cup. (I actually knew what that was!)
  3. The fact that he hasn’t won a cup is somehow weird – or else there wouldn’t be a joke worth telling.
  4. The fact that people get the joke means that Ovechkin is probably an above-average player both in terms of ability and in terms of how well-known he is.
  5. Therefore, he probably deserves a Stanley Cup, but has been held back for some other reason.

Those all turned out to be true – and that’s a LOT of information to transmit to someone with very little foundational knowledge via a single line!

(Incidentally, in 2018 the Washington Capitals did win the Stanley Cup, so finally that joke no longer works – go Ovechkin!)

The jokes of a culture carry a lot of information. Another example: when I was visiting Italy, I was given a tour of an absolutely beautiful scenic town by a wonderfully friendly local. As we took in a particularly lovely view from an overlook, he apologizes for the single factory that could be seen – in his mind, it marred the view somewhat. As someone who grew up around dozens of factories, it didn’t phase me in the slightest, but I was curious and asked what was made there. He said “concrete.”

Did you just laugh? If you did, I can tell you your national origin. If you’re wondering why on Earth anyone would have laughed just then, I can tell you that you’re certainly not Italian-American and from the Northeast.

It’s a deep stereotype both about and among Italian-Americans that they’re all stonemasons and work with concrete. Every Italian in New Jersey, New York, etc. has some uncle that made concrete steps or something like that. So my fellow Italian-Americans thought the story of me finding the one factory in rural Italy and it being one that made concrete was hilarious.

But if you didn’t know that, you could guess. If you heard me and all my cousins laugh at that story, you could gather it up.

And the thing is, every culture has these. Not just ethnic and regional cultures, but workplace cultures, industries, fandoms, etc. They all have their “in-jokes.” Jokes require a lot of shared information to be funny, so if you don’t think a joke is funny, chances are good that you don’t have the shared foundational knowledge. But if you’re trying to get it, jokes are a heck of a way to pick up clues.


Today I’m thinking about a strange pattern of human behavior that I’ve been able to witness on occasion. It’s far from universal, and most people probably won’t ever see it. Still, it’s been on my mind and I’d like to explore it a little.

I know a handful of people who, specifically in the time that I’ve known them, have gone from being private individuals to being public figures in some way. I’m not talking getting elected President or becoming Taylor Swift-level famous, but definitely people that have entered the spotlight.

Importantly, this transition also came with some amount (in some cases all) of their income or status (or both) coming from that. So people whose blog or YouTube channel or whatever “took off” and now that’s what they do.

This puts me in this interesting position where I know these people, privately and personally, but I also know their public persona. And how they differ.

Now, a quick aside – everyone is different in different situations, and that’s fine to a degree. I act differently in a professional context than I do with my friends or relatives. I don’t act radically different, but I do show different sides or emphasize different things, and that’s fine. So in the sense that someone’s public persona is their professional context, it’s fine that it doesn’t map perfectly onto their private life.

But sometimes the gaps are pretty huge.

A few things I note: one, the more time you spend in the public eye, the more you’re dragged towards the extremes of whatever you do or say or represent. You pretty much have to in order to keep adding fuel to that fire, but that’s a dangerous road.

Two, that particular direction – more and more extreme versions of yourself – starts to become the only way you can grow. Deviations are punished. Learning, changing your mind, evolving – punished. Even starting over fresh is hard, because your old reputation follows.

So, you either get repetitive or you keep pushing further and further out, which in turn isolates you further and further. Your own Overton window moves with you; the further out you push, the further behind you leave the majority of reasonable voices until you start to believe that the rest of the world really is within 20% of your viewpoint, even though by now you’ve gone really, really far afield.

I think this is maybe a macro version of a micro concept I think (and talk) about a lot – not investing your own agency into other people. I talk about it a lot in one-on-one or small group settings; how to retain your independence, how to not let other people take power away from you, etc. But if you become a “personality” with ten thousand followers, that’s ten thousand people who you’ve given control of your life to.

We think of these big public figures as manipulating their public, but it’s the other way around. They push you. The only thing you can extract back is resources, but not opinions. A massive online pundit can get his followers to give him money, but he couldn’t make them change their political views.

That’s why the only people who can survive under those conditions for very long are the people who only care about the money/wealth/personal power, instead of actually caring about an agenda. Who cares if you can’t evolve if you never cared about your topic in the first place – if it was just a vehicle to extract power?

Be careful out there. The best bubbles are small ones.