For years, the CEO of Indeed had the worst desk in the whole office. It was by the main entrance in the middle of the floor near some very popular conference rooms. He never explained himself to me, but I inferred it was some combination of humility and wanting to make himself available to people in the company to come talk to him. In all those years, I never once saw anyone walk up to him and start a conversation. Even I only ever did it once, and I’d been at the company for years longer than he had.

This may seem strange. Surely he put himself there so that he could be approached. He removed the physical barrier, but why were people still blocked?

The answer is because the physical barrier wasn’t the only barrier. Consider. You’re an ordinary employee of a multibillion dollar company. The CEO has a lot to think about and do. There’s no way any of your questions or concerns could be more important than what he’s doing right now. Do you want to disturb that? Do you want to risk being the target of his irritation? Even if he’s the most easygoing, good-natured person in the world, he’s still the CEO! Best to leave him alone.

The psychological barrier is nearly impenetrable. There is a significant power dynamic in most American companies between the CEO and most employees. Well-intentioned leaders try to make themselves available. They announce open door policies. What they don’t realize is those aren’t sufficient. They emit a repulsive force, and if they want the average employee to approach, they have to overcome that. They can’t just be available. They have to invite engagement, they have to invite the interruption, they have to invite the conversation. Otherwise it won’t happen.

So why was I the exception? Was I oblivious to the power dynamic? Am I possessed of a steely nerve? Do I have an enormous ego? It’s none of those. That one time I did it, I was anxious and nervous. The only thing that made me do it was the sanctity of my purpose: I was doing it to ask for something for someone else. If it was for myself? I never would have done it.

There are only three things that matter when hiring people, in increasing order of importance:

1. Who they are right now
2. Their durable, persistent traits
3. How well they can adapt

Who they are right now only matters with short time horizons. If you have a job that needs to be done relatively soon, you don’t want to pay a start-up cost. You also don’t care about the person in the long term, because your long term and their long term diverge. The longer you expect to employ them, the less this matters.

When you do have a long term in mind, there are two things that you want to balance. You want to know what their durable, persistent traits are: deep strengths, deep weaknesses, patterns, preferences, and so forth. While everyone has the capacity for change, few of us change completely, and some kinds of changes are much harder than others. You want to identify people whose durable, persistent traits are generally advantageous and operate at a meta-level, for instance work ethic, integrity, curiosity, and intelligence, and you want to maximize these traits.

Finally, and most importantly, you want adaptability. Over a long enough time horizon, adaptability becomes almost the only trait that matters. That’s because over that time, you can expect pretty much every hard skill to become obsolete and the demands for many soft skills to shift and mutate. You want people who are willing and able adapt to all of that change. But you don’t want them to be too adaptable. If the environment evolves to tolerate laziness, dishonesty, or complacency, you do not want them to adapt. You want them to resist the environment changing that way in the first place and fighting to reverse the change if it does happen. Unlike the meta traits describe above, adaptability has a sweet spot. The value of adaptability increases as adaptability increases but only to a point. After that, the value of adaptability diminishes, because it makes it possible to adapt in ways that may be beneficial in the short term but harmful in the long term. That’s why it’s important not just to have durable, persistent traits, but also for them to be the right ones.

Whenever you’re explaining a complex idea to someone, it makes sense to check their understanding. There’s no sense in continuing to explore the idea if the listener is stuck. They’re not going to be able to follow you. However, there are two problems with asking someone if they understand.

The first problem is ego. Everyone wants to learn. Nobody believes they know everything. And yet, in the moment, people often don’t want to admit a lack of understanding. Sometimes they don’t want to admit it to you, but quite often they don’t even want to admit it to themselves. Saying they understand allows them to continue believing the story they want to tell about themselves. That’s a difficult habit to break.

The second problem is confusion. It’s possible to be simultaneously confused about an idea and also be confused about your confusion. In other words, your misunderstanding of the idea is compounded by a lack of awareness that you understand. This is related to the Dunning–Kruger effect. In the words of the great George Bernard Shaw: “The single biggest problem in communication is the illusion that it has taken place.” They think they understand, they tell you they understand, and so you think they understand. You can’t rely on answers. You need a proof.

That means you have to check understanding in different ways, ones that don’t have the same level of ego threat and also don’t rely on the judgment of an unreliable judge. There are at least two ways to do that. One is to ask them to explain the idea back to you in their own words. Assuming they’re not just using a thesaurus to replace your words with theirs, that will get you some of the way there.

Of course, purely abstract understanding, even if sound, does not mean practical understanding. Thus the second test is to have them apply the idea. It could be to a hypothetical situation or a real problem, but have them apply the idea to some specific situation. That will demonstrate the understanding. What’s especially good about this is, if they don’t fully understand the idea, they’ll be more likely to realize it, because they’ll get stuck or come up with a nonsensical result. Better they figure it out themselves than have you tell them.

When someone asks you for help solving a problem, ask them, “what have you tried so far?” People asking for help are going to fall into two rough categories.

In the first category are the ones who came to you for help only after they failed to solve their problem on their own. These people are hard-working and earnest. Often they’re smart and capable. Finding out what they’ve tried so far saves you from wasting your time trying things that won’t work.

Then there’s the second category. Those are the people who haven’t put in the effort. Maybe they’re not hard-working, maybe they’re not capable. Those people should not be coming to you for help, but it’s not nice to say so. But if you ask them what they’ve tried so far, and they say “nothing?” Well. That sets you up to politely refused to invest any more time into their problem than they have. Pretty soon they’ll figure out this is what you’re going to ask. Either they’ll try harder, or they’ll stop coming to you. Either way, you’re better off.

I was talking to someone who worked on Microsoft Word early in his career. He joked that, if there were any irritating bugs in there, it was probably his fault. My instant internal reaction was that it was definitely not. Individuals don’t cause bugs. Systems cause bugs.

When people encounter buggy software, the often complain that the software engineers must be bad. It’s possible that the software engineers were bad. After all, someone had to write the bug in the first place*. That doesn’t mean it had to go to production.

Maybe there was a bad engineering manager at work. They made commitments without consulting the team, signed on to features without scoping them, and thought design was a waste of time. Maybe they drove the team to work twelve hour days for months on end. You take a great software engineer and put them in that situation, and you’re going to get bugs.

There are also other individuals involved. Maybe the designer came up with a bad UI. Maybe the product manager always pushed fixing bugs to the sixth subbasement of the backlog. Maybe the QA team isn’t being thorough enough.

More likely it’s a higher level leadership problem. Maybe there’s an executive sponsor who thinks software engineers and product managers can do the QA in a short-sighted attempt to constrain costs. Maybe they don’t believe in training. Maybe they insist on hiring only lower cost new college graduates rather than experienced engineers. Maybe they create perverse incentives, where teams are rewarded based on hitting dates but not on the quality of what does hit that date.

That’s often where the root of the problem lies. A good leader will certainly push for substantial delivery quickly, but a good leader will also be in touch with reality. They’ll know that people need training to build their skills. They’ll know that the team needs to be able to influence the feature list or the deadline and probably both. They’ll know that non-feature work, like writing unit tests or refactoring messy code, will pay off eventually. They’ll know all these things and they’ll fund them, with money, staff, and time.

When you try to use buggy software, it’s okay to be frustrated. Just recognize that it’s not an individual problem. It wasn’t one person that released that bug. It was a whole team that did it.

* assuming it’s even that kind of bug, with explicitly incorrect behavior, as opposed to something else, like an unexpected consequence, platform limitations, or a missing feature.

There are two questions/frustrations I frequently hear from leaders about the work people are doing in their organizations. One is “why are they doing that [thing that I don’t think is important]?” The other is “why aren’t they doing [that thing I think is important]?”

There’s an easy answer to both: because you didn’t tell them what you thought was important. I’m sure your immediate internal response was, “I can’t tell them everything!” You’re right! You can’t. Realistically, we actually only say maybe 10% of what we mean. We rely on context, precedent, and people’s good judgment to fill in the rest. If they can’t do that, it’s a real problem.

But that’s not the same as expecting them to be able to read your mind. For one thing, you may be saying the wrong 10%. Or you may be saying it wrong. Even if you’re saying it right, you can’t realistically expect people to guess right on the unsaid 90%. This is inescapable trade-off of working with people. They’re going to make different decisions than you. Sometimes they’ll be better ones that you would have made, but even if they’re always worse, you have to accept it. They’re not going to always fill in the blanks the right way. As the leader, this is your problem. Find a way to fix it.

When I first became a manager, three of my direct reports were new college graduates. The start of my professional career had been rocky. I was clueless, and my managers were not very good at coaching. Oh, and then there was the dot-com bust, which derailed me multiple times. I often think about what my career could have been with more support and without the external shocks. I was determined to do better for my new recruits.

What I realized was that my previous managers weren’t invested in me, and they didn’t seem to appreciate what was at stake for me. They chose what projects I worked on, how much I had to work, what I learned, how to help me, how much I got paid, and whether I had a job. That is an immense amount of power, but it was actually even more significant.

When I compared my career to my peers, it became apparent to me how important the first job was. That first job was key to my understanding of what a job was like, what it took to succeed, and what I was capable of. Unfortunately, I didn’t learn any of those things from that first job. Maybe it was mostly my fault, but my managers didn’t seem to try either.

That’s when I realized that being someone’s manager is a sacred trust. As a manager, you have massive control over someone’s present. Even more, when someone has little other professional experience, you have massive influence over their future. What do they learn? What can they demonstrate? What can they brag about? Do they look forward to their career with optimism, as something that can help them fulfill some greater purpose? Or do they see it as a necessary burden to keep from starving?

If you screw up, sure, they can recover. With a lot of luck, I did. But did I recover to where I would have been otherwise? And what if I hadn’t quite been so lucky? If you don’t do well for them, they’re going to be in a hole.
It’s your responsibility to keep them out of that hole and then ahead. That first job affects the slope of their career. One day, they’ll leave you. If you did your job right, it’ll be after a good long time, and they’ll leave on a much steeper trajectory than they came in on. It’s more than just paying money and getting work. You are influencing the shape of their entire life. If you don’t treat that responsibility with reverence, perhaps this is not your calling.

A determined professional will strive to keep learning throughout their career. Sometimes that learning is easier. Sometimes it’s harder.

If you focus on facts, you’ll find learning gets easier. The act of learning makes you a better learner, and you can build on previous knowledge. Learning your fifth programming language standard library is going to be easier than learning your first programming language’s standard library.

Deeper hard skills are sometimes easier and sometimes harder. They can be easier when they’re just reformulations of stuff you already knew. They’re harder when they represent new paradigms unlike anything in your experience and thus contradict the intuition you’ve developed over the years. This can also challenge your ego, making you stay within your comfort zone of expertise so you never feel like a n00b.

What will keep getting harder to learn are the soft skills. One reason for that is that that type of learning often comes from mistakes, and as you become more established and more comfortable, you may make fewer mistakes. It’s easy to see that as a positive development. It mostly is, but if you’re not making mistakes, you’re not challenging yourself, and you won’t be growing.

But I think the biggest challenge is that, inevitably, what’s left for you to learn is what’s hardest for you to learn. Maybe there’s a problem or an ability that’s invisible to you, that you can’t even perceive, like color-blindness. Maybe you can see it, but you don’t understand how it happens. Or, perhaps you can see the problem and understand why it happens, but you struggle to exercise the self-control or skill to deal with it. The problems that you can readily see, understand, and deal with? You took care of those when you were 25, when you were 30. Once you get a decade or two into your career, those low-hanging fruit have been plucked, and all that’s left are the ones that are hard to reach (or in a different tree entirely).

What’s particularly galling is that the things you have to learn are yours to learn. Some things come easily to you and only with difficulty to others, perhaps never. The opposite is true as well. I have no idea what makes some things easy for some people but hard for others, but I do know it can be surprising what people have trouble understanding. I’m sure what I’ve failed to understand has been surprising for others.

I think this is one reason (of many) why many people’s careers stall out at a middle level. The way that you’ve been learning and improving stops working. The problem is nobody tells you it’s stopped working. You just… stopped, and unless you find a new way of identifying your blindspots, understanding what’s in them, and adapting your behavior, you’re going to stay stopped.

Life is disappointment. When you try to do hard things, you’re going to fail a lot. You’re going to get rejected a lot. Hearing “no” sucks. You have to get used to it and learn to deal with it, but it’s always going to be unpleasant.

The thing about hearing no is that it brings closure. Closure brings clarity. If I know one door is closed, I can explore other doors, even windows. If I get that no quickly, I can move on without losing time or emotional investment. Any long term goal I am pursuing will be achievable through multiple strategies. Plan A doesn’t work? Then I’ll go to plan B. Or C. Or D. But I have something to fall back on so I can at least make progress.

Compare that to a slow yes. Until you actually get that answer, a slow yes isn’t a yes, it’s a maybe. A maybe means you’re stuck. You have an unresolved possibility that keeps you from executing plan A but also falling back on plan B. Meanwhile, you’re burning time. You’re investing your emotional energy. And after all that, it could still end up being a no, just a really slow one.

I understand why it happens. You have hope. You don’t want to lose that hope, but you will if you hear that no. The person you’re waiting doesn’t want to disappoint you. They don’t mean to string you along, but they’re doing it. They think they’ll be hurting you by saying “no. Sure, it’s a disappointment, but it liberates you as well. You can put that maybe out of your mind and focus on the next step. You need momentum, and losing that momentum to a slow yes is going to hurt you a lot more than a fast no.

I’m not good at persuasion. I often get pushback and disagreement with the ideas I advocate. But, while I’m not good, I’m less bad than I used to be. I’ve learned a few things in that time.

Years ago I had a 1:1 with my then-boss. I had been mulling over an idea for weeks, and I was finally ready to talk about it. I pitched it to him. He had some questions, and we talked it through. And then… he wasn’t convinced. It’s not that he thought it was a bad idea. He just wasn’t ready to say it was a good enough idea that I should go and do. I was frustrated. How did he not see what a good idea it was. Then I had an epiphany. It took me six weeks to come to a conclusion, and I was expecting him to make that same journey in twenty minutes? The lesson I took away was that it takes time for people to get comfortable with an idea. You can’t rush them through the process.

Another lesson I’ve learned is that people need to hear an idea multiple times. As much as we might like to believe that facts only need to be stated once, it’s just not true. Repetition matters. Repeating an idea increases familiarity. When people hear an idea more times, they’re more comfortable with it, and they’re more able to conceive of it becoming a reality. This one is difficult for me, because I’m often worried about pushing too hard and coming on too strong, but I might be overcompensating. The important thing here is spacing it out. Take a break between repetitions. Days, weeks, sometimes months. And talk about other things; don’t just be about one thing.

Another tactic I’ve learned is ineffective is dropping the bomb. I blame television and movies, where in some dramatic scene our hero shocks and awes the audience and converts them to a hitherto unthinkable point of view. That’s not drama, that’s fantasy. You don’t want to introduce a new idea to decision-makers in a group setting. Group dynamics favor conservatism. Group discussions can easily get lost in the weeds. Discussions in general often lose a sense of proportion, but it’s harder to regain control in a group than one on one. Before the group discussion, talk to the stakeholders one at a time. Understand what they care about, what they need. Outline your idea. Get their feedback. Understand their concerns and disagreements and try to adapt. If it works, then you can go into the meeting with everything lined up. If it doesn’t, it’ll be frustrating, but it won’t be nearly as frustrating as swinging and missing in front of a dozen people.

It’s frustrating to have to do all this “extra” work. Why can’t they just get it? I don’t know, but I have a clue based on how easily I am persuaded of things, which is to say, not very easily. It’s just hard. People take time to adjust to new ideas (see above), they need to become familiar with them them, and they’re conservative, social animals who behave differently in groups than they do on their own. You can’t change any of that. But you can change whether you’re going to attempt the easy route of ineffective tactics, or whether you’ll grind out the extra effort needed to actually have a chance at succeeding.