All business is people business ultimately, and so improving your ability to size someone up should be a relentless priority — it is for me, anyway. By “size a person up” I mean figuring out how much you trust a person, how you can best collaborate with him, whether you’d hire her, whether you should fire him.

One of the simple ways I size a person up is by understanding how they understand and judge other people. In this way, I start to be build a model of the person I’m getting to know. I get to know their likes and dislikes, their biases, their underlying motivations, and of course their meta ability to evaluate people — all by hearing them talk about friends I know well.

Practically speaking, when I meet someone new, I like to ask them about someone we know in common. “So how do you know Jane?” Sure, it’s a trite question. But it can lead to a substantive exchange. It doesn’t have to be gossip. How has this person partnered with Jane? What’s frustrated him about Jane? What have been the delights?

When you ask someone to talk about their relationship with someone else, they often inadvertently reveal a lot about who they are.

At a breakfast meeting, I once asked an acquaintance — who I was also evaluating as a prospective business partner — to describe how he knew a mutual friend. As I probed, I realized this acquaintance spoke in condescending, patriarchal terms about a person who I very much considered his peer. It was revealing. I may not have gotten a glimpse at this element of his oversized ego if we had not gone down this path.

In another case, by talking about mutual friends I realized the person I was speaking to grasped subtleties about a friend’s personality that I had missed, and it made me all the more excited about partnering with him because of his extraordinary ability to make sense of at least one complicated person — and likely many others.

Bottom Line: Get to know someone new by asking him or her about someone you already know well.

It’s hard to give advice to a peer or an especially prideful person of any sort. Advice giving can be interpreted as a power move, and if you don’t deliver the advice in the right way, the other person — a colleague, a partner, someone who’s close to you in terms of professional trajectory — can feel subtle resentment. Even if he asks for your feedback, a part of him is asking himself: “Who are you to be giving me advice?”

I handle this in two ways.

“I’m Trying, Too.”

Make your advice come off as less condescending by acknowledging your own on-going quest to live up to it or your own on-going need to be reminded of it.

In her brilliant book of advice columns, Tiny Beautiful Things, Cheryl Strayed writes to a reader:

You need to stop feeling sorry for yourself. I don’t say this as a condemnation–I need regular reminders to stop feeling sorry for myself too. I’m going to address you bluntly, but it’s a directness that rises from my compassion for you, not my judgement of you. Nobody’s going to do your life for you. You have to do it yourself, whether you’re rich or poor, out of money or raking it in, the beneficiary of ridiculous fortune or terrible injustice. And you have to do it no matter what is true. No matter what is hard. No matter what unjust, sad, sucky things have befallen you. Self-pity is a dead-end road. You make the choice to drive down it. It’s up to you to decide to stay parked there or to turn around and drive out.

She literally says: “I don’t say this as a condemnation — I need regular reminders to stop feeling sorry for myself too.” And that’s what makes it work.

Another example. Recently, a friend on Facebook recently wrote about how she is grappling with critiques of her personality. Another friend — who’s her peer, not an anointed Wise One — commented: “Be yourself, because your self is awesome. Trite to say, a lifetime to try to do. I know because I’m also trying.”

I know because I’m also trying. That’s the sort of advice given by a friend who’s a peer.

From “You should…” to “I would…”

The second approach I take when giving advice to a peer or prideful person is I avoid directly addressing their scenario and instead I make it about myself. When you find yourself saying “You should do X…” you begin to trigger people’s pride instincts. Even if they asked you directly for advice, by directly telling them what to do, you risk unleashing subtle but very real swirls of resentment.

So if you tell me about an employee you’re trying to hire and a dilemma you’re facing in the hiring process, and ask me what you should do about it, I would talk about a similar experience I’ve had and how I handled it, or construct a hypothetical parallel experience and talk through what I would do in that scenario. I’m avoiding the phrase “you should do X, you should think about Y.” I’m instead saying “I would be doing X, I guess I would be thinking about Y, I wonder about Z…” I’m trusting in their ability to connect the dots between my experience or my constructed parallel scenario and their own situation.

Note that for people who are clearly my junior, or where I do not fear at all any status offense, I will sometimes be quite direct in my advice. But relationships with peers at work and the associated status considerations are rarely quite that simple!

Josh Barro’s review of a new book about America’s physical infrastructure (roads, bridges, airports, etc.) touches on the idea that “small thinking can be a virtue, because the history of infrastructure is a series of experimental and incremental improvements.” The book under review “brings an eye for the little things: what kinds of guardrails are best, how roads can be made safer through better signage, which paving materials last longest.”

A little-things agenda is not sexy, as is highlighted in the discussion of one of the most disastrous public works projects in recent history: The Bay Bridge in San Francisco-Oakland:

Petroski devotes one chapter of his book to the new eastern span of the San Francisco-Oakland Bay Bridge, which opened in 2013, nine years late and $5 billion over budget. “With uniqueness also come uncertainties — of complications during design and construction and of cost,” he writes. Replacing an old bridge with seismic problems could have been done fairly easily and cheaply by building a simple viaduct. But politicians wanted a “signature span,” and for a variety of aesthetic reasons they chose to build a single-tower, self-anchored suspension bridge — a relatively rare design. The proposed bridge would be the longest of its kind in the world.

But self-anchored suspension bridges lack the massive anchorages at each end that are typical for suspension bridges. Instead, the cables would be anchored to the deck itself. Because of the desire to add a cantilevered bike lane, the bridge would also have to be wider on one side than the other.

This combination of specifications led to a variety of unforeseen complications. The addition of the asymmetrical bike lane required a counterweight, which would increase the load on the bridge cables, which would pull on the deck, which therefore had to be built stiffer to resist the stronger pull. But the stiffening would make the deck heavier, further increasing the load on the cables, requiring further stiffening, and so forth.

These shifting specifications added greatly to time and cost, obliterating the justification that had led politicians to choose to build a new bridge in the first place: that it would cost about the same amount as retrofitting the old span to be safer in earthquakes. And in the end, the single tower wasn’t built quite upright, and the technique used to straighten it after construction weakened the steel rods inside it, calling into question how seismically sound it was anyway.

Politicians aren’t drawn to megaprojects just because they believe the initial rosy cost projections and therefore underestimate the risk of complications. They also see an opportunity to build their legacy: It’s more fun to say “I built that bridge” than “I retrofitted that bridge.”

In this case, the hubris of politicians and civic leaders got in the way of a less-sexy and less-complicated plan.

There’s a lesson for business leaders in here, too, I think. So many new initiatives at companies are big, bold, sweeping, inspirational. You rarely hear a CEO announce to his or her employees a “yearly theme” or new cultural initiative that focuses on the corporate analogs to “making sure the signage is still up on the roads” or “putting down lane markers that won’t come off when snow plows drive over them.” In other words, initiatives that are small and incremental but perhaps surprisingly impactful — e.g. shaving 15 minutes off every scheduled meeting, or double-checking every email to a customer to make sure the tone is just right.

In Israel last year, our group of 50 — young leaders in tech — gathered on a beach and split into small groups. A few consultants led us on a team building exercise. They instructed us to build rafts using logs of wood and rope they had provided us. Once we constructed the rafts, we raced the other teams into the water, circled a buoy with the raft, and returned to shore as quickly as we could. The first team to return to shore was declared the winner. To the winner went…the pride of winning a team building exercise on the beach.

Some people took the competition very seriously. They strategized; played drill sergeant; pestered the facilitators to get clarification on the scoring methodology; and expressed joy or dismay at the results, depending.

I found myself not caring. At all. I marveled at how competitive others were getting about an exercise that had zero real consequences other than momentary pride. Yet, I think of myself as a generally competitive person. But the experience crystallized the fact that I am not always competitive all the time.

Some people always want to win. It can be in business, a board game, a sports match, or a team building exercise. Michael Jordan’s father famously said, in reference to Michael’s supposed gambling addiction, that Michael didn’t have a gambling problem. Rather, he had a “competition problem.” Put him in any scenario where there’s a clear winner or loser and Michael can’t stop trying to win.

In the group in Israel, there were many classically successful people, alpha males and females, leaders. For some of them, when the competition light goes on, their emotions soar. It’s not an uncommon trait in business leaders. Chris Sacca tells an anecdote of Uber CEO Travis Kalanick attaining the rank of second in the world in the global Wii tennis leaderboard. It’s not enough for Travis to be atop one of the world’s most valuable tech companies. He must win at everything — even video games.

Not me. I am situationally competitive. I’d like to think I get competitive when the stakes are high, my investment real, and the payoff meaningful to me. Although this is not as colorful a personality as someone who’s limitlessly ruthless — a Larry Ellison-esque archetype the business press loves to cover — I know many successful CEOs who cut a different, more restrained mold.

Of course, I don’t mean to come off too saintly (“I preserve my competitive energies for solving world hunger, thank you very much”). My reptilian, status-conscious brain gets triggered plenty. Indeed, I do care lightly about winning an informal game of pickup basketball, for example. It’s an activity as consequence-free as the raft exercise but I express more care perhaps because I am more skilled at it. I am not particularly good at helping build a raft: I can’t tie knots and generally don’t like to do manual labor. So maybe another lesson is I choose not to care about winning when I am not well positioned to win.

In general, though, one of the most important ways I’ve evolved over the past decade — as I wrote in a post seven years ago — is that I have shrunk the “stuff I care about” box. I don’t want to expend energy trying to win an inane argument. I don’t want to expend energy trying to win at some arbitrary competition I don’t care about. I just don’t care.

Except when I do.

I recently had dinner with a CEO of a fast-growing startup. He told me that he wants his employees to have deep, emotional relationships with each other, which often means becoming great friends outside of work. He wants his employees going to each other’s weddings. He wants to blur the lines that normally separate “colleague” and “personal friend.”

This value manifests at his company in at least two ways. The first is simply the language he uses, saying things like, “I want you all to be great friends outside of work!” or “It’s awesome that Joe went to David’s wedding.” The second is by the team activities he schedules. For example, “Let’s grab beers at the bar after work” or “Let’s all do a hike on Sunday.”

I wrote recently about the values that distinctively shape a culture. They aren’t values you see on official company press releases like “integrity” or “excellence.” Rather, they’re ideas that have both pros and cons. For example, transparency up and down the org chart has upside and downside, so as a value and policy it uniquely shapes those companies that embrace it. Consensus-driven decision making is another example of a value that has upside and downside.

This particular example — promoting social activities that blur the lines at work so that there isn’t as as strong a distinction between “friends” and “colleagues” — is another solid example of a cultural value with both pros and cons.

The pros to blurring the social lines among your employees are fairly obvious:

• Stronger trust among the team. When you hang out in non-work settings, you tend to get to know other side of someone and this greater familiarity likely leads to greater trust when back at the office.
• Improved communication. More time together, more time communicating. More communication is always a good thing.
• Better employee engagement and retention if employees feel like some of their best friends are at work. For someone who has great friends at work, it’s more than a job and it’s more than the company mission. It’s about the deep relationships he or she is forming. Presumably, this translates into superior engagement on the job and higher overall happiness.

The cons to blurring the lines are more subtle:

• Sexism and tricky gender dynamics. It’s exceedingly hard for women and men to be close personal friends in general due to sexual tension. This is a fact of life: see this famous clip from When Harry Met Sally. So there’s necessarily awkwardness in a work culture that promotes employees chumming it up in personal settings. Popular after work activities like “let’s all grab beers at a bar” can create awkwardness for female employees if they’re in the distinct minority. Sadly, some male leaders, recognizing potential awkwardness of co-ed out-of-office socializing, make it easy for themselves: they invite only other guys to the bar to watch the game. This greases a two-tier culture: the men are buddy-buddy, hanging out after work and on the weekends, and the women, with no company-organized outings to facilitate off-hours bonding, don’t forge the same tight bonds. By the way, the CEO whose blur the lines philosophy inspired this post has roughly 50 employees, 85% of whom are men.
• Many employees prefer boundaries. Some people don’t want to grab beers with colleagues after work. Some people don’t want to hike with co-workers on the weekend, especially folks with families. Sure, it’s not a big deal for people to decline the weekend hiking invitation, but just receiving those invitations and feeling pressure to go on them can provoke guilt and light weight irritation. A culture where everyone is expected to be friends outside of work might repel prospective high-talent employees who want more work/life separation. Given the kinds of people who work at startups, entrepreneurs tend to promote a line blurring culture in the early days, but this is harder to maintain as a company scales and needs to draw on a more diverse and older portion of the professional population.

Personally, I blur the lines between professional and personal in many of relationships, which is to say some of my best personal friends I met originally in a professional context or are people with whom I still work professionally. But making this instinct a part of a corporate culture raises different considerations.

Bottom Line: Within a company, there are obvious benefits and less-understood risks to suggesting employees become close personal friends outside of work an explicit part of the culture. Male CEOs in male-dominated companies should be especially aware of the downsides, as should startup CEOs who need to attract an increasingly diverse professional population as they grow.