Not in Your Head

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Most of the world builds their cars using metric measurements, with meters and kilograms. Until recently, American cars were built in inches and pounds. Nowadays, American cars are an amalgam of components from around the world, and as such are a hodge-podge of both systems. To work on these cars, you need two sets of tools, standard and metric. No repair shop would be caught with just one, and no tool company builds just one either.

The same is true in the computer world. The brains that run personal computers come in a lot of flavors. Intel forged the way with the x86 chips. These tiny masterpieces were the core of the IBM PC and all the myriad compatible machines from Dell, HP, and so on. But the 1990s, the start of the PC era, were a fluid time for hardware. Digital Equipment had their Alpha chips and Silicon Graphics machines used their MIPS chip. Apple was the most fickle of all, building their MacIntosh first with Motorola’s 68000 series chips, then going through a wrenching conversion to Intel chips for a decade or so, and just this year has decided to convert to their own chips.

Like with cars, software developers need tools, custom to each platform. Microsoft has known that owning the tools is a great way to win mind share and lure developers into their world. When I was there, we fought a pitched battle to win the market for Intel tools against really smart rivals. I was tasked with leveraging that win to all the other chips, by building tools for the array of alternatives.

The complexity of this problem haunted me. There were at least four different variants with more on the list, and each would need a complete set of tools. Tools that would build software for each chip, and even across from one platform to another. Tools built using tools we hadn’t built yet. It was a chicken and egg problem of the first order.

The scale of this problem kept me awake at night. During the day, I paced in my office wrestling with all the pieces. I would wonder aloud to my ever-patient admin, Jill, about the details and rant about how we’d never get it done.

The first few meetings with my team on this project were hard. We had been building a Mac toolset for a while, but it was rough and the way we built it wasn’t reproducible. The idea that we could replicate that multiple times over was simply a fantasy. I remember flailing at my team in one meeting yelling “you just don’t get it”. I was defeated as I walked back to my office, certain that we were headed for failure.

That’s when Jill quietly turned to me and said: “they’re not inside your head”. And that’s what this is all about.


This is Leading Smart, the show about Managing in the Brainpower Age. It’s a field guide to the joys and challenges of leading and working in the modern workplace. I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.

This episode begins a series on communication as a leader. This time we’ll explore the inside of a leader’s mind. This is Episode 218 — Not in Your Head.


One of the coldest realities you learn as an adult is that you can’t really know what’s in someone else’s head. Anyone who’s been in a personal relationship has found themselves wondering, “what are they thinking?” Who among us hasn’t been left vacant by “what do you mean, what’s wrong? I’m fine.” And every parent of an infant or owner of a pet has pleaded to know what’s really bothering them.

The same is true in the workplace. Every leader at some point has wondered if the team is really with them. Do they believe in the vision? Do they share my passion for the project? Are buying what they are being sold? If only you could get in their head.

It’s worse on the downside. Leaders see things that just don’t feel right. Numbers that are foreboding, messages that seem off, team interactions that seem broken. They wonder if they’re making something from nothing. If it’s all in their own head.

In a future episode in this series, we’ll look at how to resolve these questions, or at least start to. To get some idea of what’s in your team’s head. And how to know if the things rattling around in your head are worthy of those sleepless nights. We’ll look into getting great feedback and understanding where things truly stand.

In this episode, however, I want to look from the other side. From the team’s perspective. To see how badly they want in your head, but frustratingly can’t get there.


I like to challenge leaders to swap roles, to change perspective. To imagine what working in their organization is like. To peer up to themselves as a leader. What do they see? What’s the culture? How does it feel?

This is a difficult exercise for most. We’re so caught in our own world, things are happening so fast. And many leaders are such driven personalities that this kind of reflection is hard.

Yet there are many ways to gain this perspective. Perhaps they can think back to when they weren’t in charge. When they too were looking up to a leader. Or perhaps even today, as they look up. What do they feel peering up at their boss, and beyond to senior management?

This is most difficult for CEOs or business leaders who have no one above them. Their view is solely out and down. And it’s doubly difficult for people who’ve never worked for anyone else.

Nonetheless, it’s an exercise worth doing. So let’s spend just a few minutes inside your organization looking up.


Whether you’re a newbie or an old hand, the view upwards in an organization doesn’t change much. But the perspective can.

Looking up, you see that your boss has the power. They set the agenda. They make the tough decisions. They manage the budget, give out the promotions, hire and fire. Sure, “everyone is a leader” they say. You can put in your two cents, make your case. But ultimately, the boss decides who really gets heard.

In many ways it’s not that different than a personal relationship. You wonder what they’re thinking. You ponder what’s really bothering them. Why did your boss blow up in that meeting? What did I say? Do they hate me now? Should I be looking for another job?

In the absence of a real narrative, stories are crafted. The lunch table is abuzz with theories. Notes are compared, tea leaves are examined. Speculation is the norm.

In this vacuum, every little clue is taken as gospel. When the boss makes a simple comment in passing, “maybe we should do less of that”, it blows up. Soon the entire team is warning each other “whatever you do, don’t do that, the boss hates that”.

And when the boss comes in with the latest crisis on their mind, the whole team valiantly rises to meet it. So desperate to be in good graces, everyone juggles priorities to address the newest need.

People try to help each other, “why are you doing that, didn’t you hear the boss, we need to be doing more of this”. Or worse, try to sabotage their peers, sending them off on a wild goose chase. Without confirmation, who’s to know?

Again, the boss arrives with the latest crisis, the latest mandate from above. Whipsawn, the team zigs with every zag. Thrashing this way and that. Until of course they shut down. No longer sure what’s real, what’s a crisis, what really needs to get done.

The boss, frustrated with the lack of real progress, gets more animated. More upset, more aggressive. They lash out at the nearest unlucky soul. Witnesses soon recount this as evidence, that yes, the boss really does hate some people.

The team shuts down even further. They haven’t the slightest idea what the boss really wants. What the priorities are. What is real, and what is fiction.

And why? Because the boss keeps it all bottled up. Until it overflows. Maybe they’re overwhelmed. Maybe it’s bravado. “I can handle this. No need for them to be distracted by all this noise.” Maybe they’re just selfish. But whatever the reason, the team is in chaos. Because no one knows what’s in the boss’s head.


As a leader, you have a unique perspective. You see more of the whole picture. You have input and ideas and data they don’t have. You see opportunity they can’t.

On the flip side, they’re not wrestling with the same problems you are. You have responsibilities they don’t. You have pressures they will never see and might not even understand if they did.

So what to do? You let them in. At least in some way. You get open and honest, and even a bit vulnerable with them.

I advised a leader to do this once and got a horrified look in return. “Egad,” they said, “it’s a rat’s nest of complexity in there, they’ll never understand. They don’t really want to be in there.” “But yes,” I counseled, “they really do. They want —­ and need — to understand what you’re thinking.”

Again, just as in personal relationships, teams are rarely made worse with open, honest communication. Be candid, share your passion, and your concerns. Let them see what drives you, what makes your job fun, what makes it a challenge. Share your hopes and dreams for the team, the project, the organization. And, yes, you need to share what scares you. The nature, if not the details, of what keeps you awake at night. This all humanizes you, and also helps them appreciate your role.

But there are some caveats. The goal is to paint a larger picture, to help them understand. Offering a glimpse of your world with an example or two is sufficient. Too much detail, too many naked truths, will only up anxiety. Without context, the team indeed won’t understand, they won’t be able to help, and they’ll likely be frustrated.

Make your sharing lean toward the upbeat. No, not a view through rose colored glasses. Glossing over or blatantly ignoring the challenges will expose you as a fraud. But help them see why you’re excited, the opportunities you see, the path you envision to success. Leave everyone with something to do, a task at hand, a way to participate. And always try to end on an upbeat note.

This is where a vision comes in. Season one of this podcast has a whole series on setting and communicating a vision. It’s worth a listen. A good vision can be the framework that allows you to have real meaningful discussions without sending everyone off on the latest crisis. A great message, delivered often, has a marvelous insulating and calming effect.

As you share, remember it’s a two-way street. Empathy and understanding are essential. Swapping perspectives is good, but genuine, earnest listening is best. Work to understand your team: their motives and fears, their challenges and frustrations, their infighting and culture. Great communication is essential to great teams and is the focus of the next several episodes.

In the end, Jill was indeed right. As she often was. Letting the team into my head, though terrifying, was and remains, a great idea.


Leading Smart is from me, Chris Williams. You can find out more about the show and discover other resources for leaders at my web site CLWill.com.

If you like the show, please share it with your friends especially on social media. Referrals are the greatest source of new listeners. I’d also love your feedback. I’m “theCLWill” on Twitter, LinkedIn, and Facebook, or send email to pod@clwill.com.

That’s it for this episode. The next episode is another of my conversations with leaders. We’ll talk with Tod Nielsen, the CEO of FinancialForce. I hope you’ll listen. Until then, please remember that each of the several dozen decisions you make today are part of Leading Smart.