Asking Acquaintances About Mutual Friends

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.

When Giving Advice to Peers…

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!

A Little-Things Agenda

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.

Situationally Competitive vs. Always Competitive

Line of Business
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.

Blurring the Professional and Personal Lines at Work

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.

Short Term Profit Taking vs. Long Term Value Creation

Reid recently penned a piece about Carl Icahn’s ambitions to split PayPal off from eBay, and the broader difference between the short-termism of Wall Street vs. the long-termism of Silicon Valley. The piece generated a lot of attention and it advances some some important ideas. Give it a read. My favorite line: “Innovation comes from long-term thinking and iterative execution.”

The Power of the Word “Yet”

Suppose your boss pulls you aside and tells you: “You don’t have the right skills for the project.”

Then suppose a different situation, where your boss tells you: “You don’t have the right skills for the project, yet” or “You don’t yet have the connections to make this deal happen.”

The word yet makes all the difference in the world. In the first example, you feel like a dud. In the examples with “yet,” you feel like you may not be ready now, but you could be in the future.

Carol Dweck, the Stanford professor who’s researched the idea of a “growth mindset,”elaborates:

By [using the word “yet”] we give people a time perspective. It creates the idea of learning over time. It puts the other person on that learning curve and says, “Well, maybe you’re not at the finish line but you’re on that learning curve and let’s go further.” It’s such a growth mindset word.

As Chris Yeh points out, when you’re mentoring or helping someone, you want to emphasize the idea of on-going improvement. He offers two more “yet” examples:

“You haven’t been able to find a replicable sales model…yet. But each program your startup tried has taught you something, and you’re refining your approach.”

“You haven’t been able to play that violin piece without mistakes…yet. But every time you practice, you’re getting a little better.”

Bottom Line: Next time you need to criticize or offer feedback to a colleague, add the word “yet” — and you’ll be encouraging a growth mindset.


A single word can carry an entire thought. In a previous LinkedIn post, I noted that basketball coach Gregg Popovich inspired his players to work hard with the phrase “I want some nasty.” The word “nasty” brings the idea to life.

(Originally posted on LinkedIn)

Experts Take Notes.

Recently, Mark Zuckerberg addressed a large auditorium of young entrepreneurs in Silicon Valley. He shared lessons from his journey and his perspective on the state of the internet industry. Every seat was taken, and the 20-somethings who aspired to entrepreneurial greatness were listening with rapt attention.

According to my friend who relayed this story, there were two older folks in the front row who stood out: John Doerr and Ron Conway. They are both legendary investors in Silicon Valley.

They stood out not just because their gray hair shimmered in the sea of youth around them, but because they were the only people in the audience taking notes.

Isn’t it funny, my friend told me, that arguably the two most successful people in the room after Zuckerberg were also the only two people taking notes?

As I wrote in the excerpts from the Five Elements of Effective Thinking, experts understand simple things deeply. They return to the basics, over and over again. eBay CEO John Donahoe is widely regarded as one of the premier execs in the Valley right now and I’m told is an avid note-taker to boot. He recently said on LinkedIn, “Great leaders are never too proud to learn.”

You could argue people have different approaches to capturing nuggets of wisdom and committing those nuggets to memory. Sure. But I’m skeptical of passive learning. If you don’t write down what you’re hearing and learning, what the odds you remember it? I take lots of notes in paper mole skin notebooks; every week or so I go back with a different color pen and circle the key sentences; I then transfer these ideas to Evernote files on my computer; and finally, I blog/tweet/publish/email out the crispest, most important ideas or quotes. And this is nothing compared to Tim Ferriss’s extreme “take notes like an alpha geek” system, which is worth learning about.

You might argue people like John Doerr and Ron Conway are old school. Most young folks today, you’d say, aren’t going to be using pen and paper in the first place. Fine. The actual technology/process is not as important as having a repository, and preferably having a system that reinforces retention.

I thought about this broader idea the other month when I visited the University of Washington business school the other month. I was giving the keynote talk in the afternoon, but I set my alarm clock early to catch the morning keynote from my friend Charlie Songhurst. I know from personal experiences that Charlie is unusually insightful. As he delivered his keynote to the MBAs in the audience I noticed something peculiar: almost no one was taking notes–on paper or on tablet or computer. Well, I was. A few other people were. But most weren’t. There was plenty to write down, to be sure. It was an insightful talk. What gives? My theory: The audience was mostly students. Experts — or those who have deconstructed what experts do — take notes. Novices don’t see the point.


There’s an old rule of thumb that if you have something really important you need done, ask for help from the busiest person you know. Here’s an analogous rule: if you want to identify the most senior, knowledgeable people in an audience, look for the people who are taking notes and asking questions.


While taking notes in a large auditorium in front a keynote speaker is a no brainer, note-taking in a 1:1 meeting is a bit trickier. A few years ago, I wrote about the pros and cons of taking notes in a 1:1 conversation. One risk is it can make the conversation seem more transactional than is ideal. And it can also introduce a power dynamic if only one person (and not the other) is taking notes. Still bias yourself to take notes in a 1:1, but tread a bit more cautiously.

(Photo credit: Geekcalendar)

(This post originally appeared on LinkedIn)

Simple Yet Hard, Public Market Investing Edition

Anyone who touches public market investing sings endless praise for Warren Buffett. But how many public market investors invest like Buffett — that is, actually employ the same strategy to generate superior returns? Remarkably few, it seems.

The Mutual Fund Observer recently profiled the Bretton Fund and interviewed its manager Stephen Dodson:

In imagining that firm and its discipline, [Dodson] was struck by a paradox: almost all investment professionals worshipped Warren Buffett, but almost none attempted to invest like him.  Stephen’s estimate is that there are “a ton” of concentrated long-term value hedge funds, but fewer than 20 mutual funds (most visibly The Cook and Bynum Fund COBYX) that follow Buffett’s discipline: he invests in “a small number of good business he believes that he understands and that are trading at a significant discount to what they believe they’re worth.”    He seemed particularly struck by his interviews of managers who run successful, conventional equity funds: 50-100 stocks and a portfolio sensitive to the sector-weightings in some index.

Stephen says:

I asked each of them, “How would you invest if it was only your money and you never had to report to outside shareholders but you needed to sort of protect and grow this capital at an attractive rate for the rest of your life, how would you invest.  Would you invest in the same approach, 50-100 stocks across all sectors.”  And they said, “absolutely not.  I’d only invest in my 10-20 best ideas.” 

The obvious question is why this is. There are various incentives that distort fund managers’ behavior, certainly. But my guess is that a large number of public market investors think they’re investing like Buffett, but they’re actually not disciplined enough to follow the value strategy all the way. It’s no wonder the average returns from actively managed mutual funds (versus index funds) are so disappointing.


I should note that Steve is one of my closest friends. And not just because he’s made me money from my being an investor in the Bretton Fund.

Learning to Own the Room

I recently attended an Own the Room public speaking and communication course in New York.

I’ve done a lot of public speaking, from enterprise software sales pitches in the early days, to paid keynote speeches more recently. But I’ve never formally trained. I’ve relied on some natural ability, decent content, and feedback from friends/clients along the way.

Over the past year, I felt like I hit a plateau in my verbal communication/presenting skill. I also came to the more general realization — described in my recent blog post on investing in yourself — I should be investing aggressively in my existing strengths. So I flew to New York and participated in the intensive Own the Room bootcamp, which had been referred to me by several people in my network.

It was phenomenal. I learned so much. Here are some reflections.

The native speaker who can’t write or understand grammar. When I took Spanish classes in school in California, there were always a few near-native speakers — immigrants whose parents spoke Spanish at home. Their accent was perfect and conversational pattern fluid, but occasionally they would unknowingly make very basic grammatical errors. They were never taught grammar; they couldn’t spell many words they spoke. Going through this course, I felt like I was that native Spanish speaker: when I speak or verbally communicate, I do a fine job most of the time, but now I know I make some really basic mistakes. Until this course, I wasn’t aware of the mistakes, let alone how to improve them. I’d argue that many business execs with a natural flair for speaking fall into this camp. They’re quite good, but they won’t get to great without stretching themselves beyond their natural ability.

The bootcamp model. I’ve blogged about the bootcamp model of learning. Own the Room definitely fits that mold — a couple super intensive days focused on a single topic. I still seek a framework by which you can evaluate when a format of learning fits the type of learning — i.e., I think a bootcamp model works well for public speaking, but not for language learning, say.

Demand feedback. “What did I do well? What could I do better next time?”After every module exercise, we “demanded feedback” from our partner or small group or coach by asking these two questions. This is a general learning theme, of course, but was emphasized to such a degree in Own the Room that it stuck with me more than anything else. (“What could I do better next time?” is an example of ‘feedforward’ instead of ‘feedback’ as Marshall Goldsmith calls it — constructive feedback focuses on what you can do better next time.)

Presence comes from change. Dynamic leaders have presence. It’s a hard thing to define. When do you feel someone’s “presence” in a room?  You feel presence when they change. Change their physical position. Change the volume of their voice. Change the speed of their voice. Change their point/topic. Change = presence. A huge learning.

Voice modulation and pauses. I discovered in the class two key weaknesses in how I verbally communicate. First, I don’t employ pauses enough. The rightly timed pause can make such a difference in how a point lands in the audience. Second, I don’t modulate my voice. I don’t use the full range of volume. I’m too monotone too often.

“Imagine…” Paint pictures with words. Paint pictures with words. Paint pictures with words.

Here’s a video of highlights from the first day of the course I attended.

And here’s a clip of Bill Hoogterp, owner of Own the Room, teaching voice modulation and body language: