Time to read: 50 minutes

We touched down in Las Vegas only three hours before, but we were already back in the plane and flying home to San Jose on a brisk winter day in December, 2012. Not having to go through security at an airport saves a lot of time.

Other than the two pilots in the front, Reid and I were alone, debriefing what worked and what didn’t at the tech event where he had just spoken. I gave some quick feedback on the answer he offered to a question about LinkedIn’s vision. He re-played his answer on how Greylock differed from other venture capital firms. I took notes.

The conversation then shifted, as it increasingly did those days, to a different line of inquiry: Did this trip to Vegas advance an important professional project? Did he have fun? Or both?

Every decision has tradeoffs: when you choose to do one thing it means you choose not do some other thing. When you choose to optimize a choice on one factor, it means necessarily suboptimizing on another factors. Reid faced tradeoffs in his life that were heavier than the ones you or I face. Imagine you could meet anyone, from the President of the United States on down. Do almost anything you can think of – from saving the local opera company from bankruptcy to traveling to the farthest outposts on earth in total luxury. A small number of humans have virtually no constraints on their decision-making, and Reid is one of them. When Reid chose to fly to Las Vegas and speak at this event, the list of things he chose not to do with that time was very, very long.

Often, Reid wrestled with these tradeoffs. Author E.B. White once captured the essence of why. “I wake up in the morning unsure of whether I want to savor the world or save the world,” White said, “This makes it hard to plan the day.”

For some, savor is the easy answer to the task of planning a life. For those with no constraints, the plan is often straightforward: they put their name on a few buildings of their alma matter, buy a pro sports franchise, and call it a day. For the 99% of people with resource constraints, they might bag a 9-5 job, accumulate vacation days as diligently as possible, retire early, and maybe donate to their friend’s Walk Against Cancer. Reid likes to savor, albeit not hedonistically. Savor for him means arriving at intellectual epiphanies; it means spending time with friends.

But what he really wants to do is save. He wants to use his talent and network and money to change the world for the better and solve some of humanity’s biggest problems. He is among the most selfless and externally-generous people I’ve met in my life.

Decision making becomes hard when you want to do both. Which is it today: saving or savoring? Usually you do have to choose. It’s the very rare project that involves close friends and ongoing intellectual stimulation, and change-the-world impact.

That evening, as I sat across from him on the plane, he looked exhausted. The speaking event he had just done was in the “save” or “change the world” category—it would hopefully inspire other entrepreneurs, extend the Greylock brand, and help build a couple relationships with folks in the industry. It wasn’t especially fun or stimulating and didn’t involve close friends. At that moment, I felt like he should be doing more stuff just for him. He’s worked so hard to achieve his success, why not kick back a little and play Settlers of Catan while drinking fine whisky in the south of France? Yet at other moments, after he meets with a dynamite non-profit that’s saving the lives of millions, I understand why he commits to helping, even if it leaves him drained by the end of the weekend’s marathon meetings.

The save/savor dilemma is one he’s still figuring out and probably always will be.

He’s not alone, of course. All of us who enjoy privilege in the world struggle with the dilemma on different scales. Myself, I wonder about how much energy I should expend on the billion people in the world who live on a dollar a day or less versus tending to and enjoying my own little inconsequential life. How much should I volunteer and donate to charity? What does it mean to lead a life of purpose larger than self, and is that something I even need to concern myself with? Should I feel guilty if I blow money at a resort in Thailand when people just hours away are starving?

Reid likes to point out false choices. For example, some ask if entrepreneurs should set plans or just be ready to adapt. False choice, Reid says: they need to do both. Should you have a small number of intimate friends or a large number of looser ties? Both. Indeed, one of Reid’s favorite quotes is from the great Jewish sage Hillel: “If I am not for myself, who is? And when I am for myself, what am I? And if not now, when?” One interpretation of the quote is that you must love yourself and yet you ought not to live just for your benefit. You should help others, too. Reject choosing between self-love and love of others: do both.

So I’d agree that the macro correct answer to the save/savor dilemma is: both. But in practice, at the micro level of an individual decision, we tend to have to pick one or the other. I believe tradeoffs loom larger than false choices.

This is one theme I thought a lot about while working with Reid over the past four years. In the pages ahead, I will elaborate on many other lessons I learned from him. But I suppose I should explain first: Why the heck was I on that plane back from Las Vegas in the first place?

The 40% Question

In her 2011 profile of Reid Hoffman, Evelyn Rusli of the New York Times ended with a direct quote from Reid: “I’m functioning at 60% effectiveness,” he said. It was a startling final acknowledgement because the article chronicled the lengthy list of activities and accomplishments that made Reid the “King of Tech.” Given how successful he’d been over the past decade, you’d think he was operating at 150% effectiveness.

But I knew Reid wasn’t being facetious. I had just spent two years full time partnering with him on our first book The Start-up of You, which gave me a view into his life. In addition to his duties as LinkedIn’s executive chairman, Reid worked as a venture capitalist at Greylock, served on several private and public company boards, supported a range of philanthropic initiatives, and produced various intellectual artifacts, such as our book. And let’s just say that his flow of ambition and ideas was not exactly slowing down.

It’s a lot for anyone to keep track of. On top of all that, thanks to LinkedIn’s IPO, he was now a fixture on the Forbes’ rich list. Billionaire status introduces all sorts of social complications in your life, especially for a guy who wasn’t expecting it. Reid played Dungeons & Dragons as a kid, drove oxen in high school, and came out of college with the intent of studying philosophy as a professional academic. It would be strange if there were not some “scaling” issues on the way to moguldom.

The 40% question. That’s what I titled a presentation I delivered at Reid’s house in July, 2012. The thought experiment was simple: What would it take to bridge the final self-identified 40% of his capacity so that 100% of his cylinders were firing? How would the world be different and how would his life be different as a result?

With the Start-up of You done and published, I had some free time, and so we conceived a tour of duty for me to help wrestle with this question full time. It was initially set as an interim 6 month gig since neither of us knew exactly what I would be doing. It turned into two years. We picked “Chief of Staff” as the job title, even though there was no staff to be chief of yet and even though it’s a title that means different things in different contexts.

Here’s how I now list the position on my LinkedIn profile:

I helped conceive, build up, and then run a new organization to amplify and extend Reid Hoffman’s strategic priorities.

Working out of the LinkedIn and Greylock offices for almost two years, as Chief of Staff I was involved in many of the decisions Reid made across the different areas of his work: LinkedIn (where he’s co-founder/executive chairman), Greylock (the venture capital firm where he’s a partner), his philanthropic work, assorted public intellectual projects, and political/civic initiatives.

I also strategized and executed new, proactive initiatives to increase Reid’s impact in Silicon Valley, Washington D.C., and beyond.

I hired and managed a team of employees who staffed all of the above efforts.

I loved working with colleagues at LinkedIn and Greylock and with Reid’s broad network of portfolio companies and organizations (for-profit, non-profit, and political). But my favorite part of the job was the late night 1:1 conversations with Reid like the one on the plane from Vegas, where I offered my best candid advice on whatever was on his mind and where I did my best impression of a consigliore-cum-interlocutor as he ruminated on the small and big questions animating his life.

A handful of months have passed since transitioning out of the chief of staff gig along with the publication of our second book together (The Alliance). So it seemed an apt time to summarize several important lessons I learned about life and business from Reid over three tours of duty: co-authoring Start-up of You, doing the chief of staff gig, and co-authoring The Alliance.

Note that I’m not going to get into the details of the work with Reid at Linkedin and Greylock and his philanthropy and so on, in part due to privacy and confidentiality considerations. Instead, I’m going to focus on some of the generalizable take-aways. I picked 16; there are dozens more, of course! (Also, If you’re interested in more specifics on the process of conceiving, writing, editing, publishing, and then marketing a business book, here are my detailed lessons and insights from the Start-up of You process.)

16 Lessons Learned (Among Many!)

1. People are complicated and flawed. Root for their better angels.

Too often, people classify someone’s competence or character in black and white terms. He’s brilliant or he’s an idiot. She’s got a heart of gold or she’s an asshole. He’s an ethical prince or a conniving win-at-all-costs hustler. It’s an unfortunate tendency. Expertise is always relative. Every saint has a past and every sinner has a future, as Oscar Wilde said. People are complicated.

Reid is widely known as the ultimate connector. One of Reid’s underrated gifts in this regard is that he maintains very complicated portraits of the people he knows. He appreciates the full spectrum of strengths and weaknesses of a particular person. He’ll comment on a friend’s character flaw—say, self-centeredness—but in the next breath note one of their unique strengths. Flaws that cause others to completely disengage are, for Reid, “navigable” (to use a Reid-ism) en route to their better side.

Along these lines, Reid forgives mistakes in his friends. If you make a mistake (or three) or if a weakness of yours gets exposed–you’re not dead to him. It’s just another data point in a rich tapestry in a long-term relationship. A good friend of his once convinced him to make a special trip to New York to participate in an event. Later, I asked him how it went. “It was a foolish waste of time,” he replied. And yet, the very next week, he was on the phone with the friend and plotting future moves. He’ll rarely let a single failure or shortcoming overshadow your successes or noble aspirations. And he’ll always root for your better angels to prevail. It’s no wonder his friends are so loyal to him.

It’s a philosophy that reminds me of my late friend Seth Roberts, who promoted an “appreciative” approach to life. When evaluating someone, instead of starting with their weaknesses, first ask what’s uniquely excellent about them. When evaluating a study, first ask what we can learn from it, instead of jumping to a critique of the study’s flaws. Let an appreciative point of view imbue everything you do.

2. The best way to get a powerful person’s attention: offer to help them.

As chief of staff, I reviewed thousands of requests for Reid’s time/attention/money. It was stunning how few requesters actually offered to help him on something. Amusingly, many requests were framed as if the asking party were doing Reid a favor by giving him the opportunity to help them: “It’d be fun to get your feedback on something I’m working on.” Reid’s so generous and so curious that sometimes it is fun for him to simply help you. But why not figure out what he’s working on and send an article of relevance? Or offer to share a perspective that could be useful?

Most people think there’s no way to help someone as famous and wealthy as Reid or Bill Gates. Let’s run the thought experiment. How could you help Bill Gates? Donating to his favorite charity won’t help. There’s no one you could introduce him to who he can’t already meet. Buying a Microsoft product won’t make a difference in the grand scheme. But the truth is, what Gates craves, and what you might have, is information. A unique perspective. An insight on something that’s happening in your corner of the universe. He can’t buy that off a shelf. If you can connect information you know to something Gates needs—suppose your 10 year-old cousin is obsessed with a new app that may reveal a new trend in computing—he’ll find it valuable, and you’re more likely to be able to build a relationship with him. At the least, it’s a powerful first gesture that’s the opposite of “gimme.”

Help first. Help first. Help first. It’s key to building relationships – even with the ultra successful.

3. Keep it simple and move fast when conceiving strategies and making decisions

Reid is a strategist. But he’s not someone who can recite Clay Christensen or Michael Porter verbatim. In fact, Reid has never formally studied strategy and he rarely references the famous gurus. Instead, his views on strategy are hard-won through experience, and specific to entrepreneurial contexts: situations where the overall battlefield is foggy, the ground underneath you is shifting, and death is assured if your next step is not the right one. Of course, in the “age of the unthinkable” (the title of one of his favorite books), this increasingly describes the battlefield all organizations are fighting in, not just startups.

Speed

His first principle is speed. His most tweeted quote ever is, “If you aren’t embarrassed by the first version of your product, you shipped too late.” His second most tweeted quote ever is, “In founding a startup, you throw yourself off a cliff and build an airplane on the way down.”

Practically, he employs several decision making hacks to prioritize speed as a factor for which option is best—and to speed up the process of making the decision itself. When faced with a set of options, he frequently will make a provisional decision instinctually based on the current information. Then he will note what additional information he would need to disprove his provisional decision and go get that. What many do instead – at their own peril – is encounter a situation in which they have limited information, punt on the decision until they gather more information, and endure an information-gathering process that takes longer than expected. Meanwhile, the world changes.

If you move quickly, there’ll be mistakes borne of haste. If you’re a manager and care seriously about speed, you’ll need to tell your people you’re wiling to accept the tradeoffs. Reid did this with me. We agreed I was going to make judgment calls on a range of issues on his behalf without checking with him. He told me, “In order to move fast, I expect you’ll make some foot faults. I’m okay with an error rate of 10-20% — times when I would have made a different decision in a given situation – if it means you can move fast.” I felt empowered to make decisions with this ratio in mind—and it was incredibly liberating.

Speed certainly matters to an extreme degree in a startup context. Big companies are different. Reid once reflected to me that the key for big companies like LinkedIn is not to pursue strategies where being fastest is critical—big companies that adopt strategies that depend on pure speed battles will always lose. Instead, they need to devise strategies where their slowness can become a strength.

Simplicity

His second principle is simplicity—simplicity enables speed. In situations where there are many paths, he frequently groups the possible options into “light, medium, heavy” or “easy, medium, hard.” For example, we were debating different ways to publish and promote the LinkedIn Series B pitch deck we created. We could simply click publish, share it on LinkedIn and Twitter, and see how it spreads. We could reach out to journalists in advance and give someone an exclusive, early look. We could write a series of supplementary essays that appear simultaneous with the deck. We could audio record his oral commentary on each slide. Reid bucketed the options into three categories: basic, intermediate, and advanced. “How intensively do we want to go after this?” We decided on a level of intensity and executed on the relevant set of actions.

When there’s a complex list of pros and cons driving a potentially expensive action, Reid seeks a single decisive reason to go for it—not a blended reason. For example, we were once discussing whether it’d make sense for him to travel to China. There was the LinkedIn expansion activity in China; some fun intellectual events happening; the launch of The Start-Up of You in Chinese. A variety of possible good reasons to go, but none justified a trip in and of itself. He said, “There needs to be one decisive reason. And then the worthiness of the trip needs to be measured against that one reason. If I go, then we can backfill into the schedule all the other secondary activities. But if I go for a blended reason, I’ll almost surely come back and feel like it was a waste a time.” He did not go on the trip. If you come up with a list of many reasons to do something, Nassim Taleb once wrote, you are trying to convince yourself—if there isn’t one clear reason, don’t do it. (An analogous belief Reid has about consumer internet business models: there’s generally one main business model. Listing a blend of possible revenue streams makes investors nervous. LinkedIn is the exception that proves this rule!)

Making the complex simple does not mean ignoring the complexity. Reid is a nuanced thinker who does not shy away from detail, second order effects, exception cases, and so on. But especially in a group decision making process where there’s various points of views, it’s important for the leader to distill and frame the option set with simplicity. Wrestle with complexity, yes, but frame and commit to a decision that’s simple enough for everyone to understand and act on.

Simplicity also can translate into focus. He once told me about a frustrating conversation he had with someone at a startup who mapped a multi-phase vision for a project that stretched out a couple years. “He didn’t get it,” Reid told me, “If you don’t get Phase 1 right, you’re dead. Nothing else matters. Nothing else matters. He should be completely focused on nailing Phase 1.” There are going to be fires all over the place. Keep it simple: just focus on the one, most important fire.

Empowerment: Have Those Close to the Ground Modify the Strategy

A lot of strategists (and CEOs) think that their job is to conceive a strategy and then hand it off to the underlings to execute. They might concede that delegation matters, but usually as a matter of execution more than strategy.

Reid disagrees. He once told me, “Whoever is actually immersed in the actual execution of a strategy should always think of ways to tweak the strategy for the better.” It’s a litmus test for talent: How do you know if you have A-players on your project team? You know it if they don’t just accept the strategy you hand them. They should suggest modifications to the plan based on their closeness to the details. And as they execute, they should continue to tweak the strategy, and you (the owner) should not feel a need to micromanage or second guess—if you do, you’ve got the wrong person.

4. Every weakness has a corresponding strength

I sat down with Reid one day and shared a self-evaluation of my work, my goals, and my strengths and weaknesses. When I discussed how to compensate for certain weaknesses, he told me, “Most strengths have corresponding weaknesses. If you try to manage or mitigate a given weakness, you might also eliminate the corresponding strength.”

He shared a personal example about himself. He is not particularly well organized. But perhaps his day-to-day chaos partially enables his creativity. Creativity involves connecting disparate ideas. The man is a non-stop generator of ideas — perhaps the unstructured tempo of his life is a positive enabling force. How intensely organized you are and how creative you are may be two opposite sides of the same coin.

Another example: his loyalty and generosity with friends is a strength. Friends are so important to him, and he to his friends, and the stellar results of his collaborations with friends are for all to see. But sometimes he gives too much and sometimes his friends take too much and it pulls him away from taking care of himself.

This two sided coin idea informs one of Reid’s classic strategy jujitsu moves: turn your weakness into a strength. For example, if you’re a startup and worry your lack of a track record is a liability, instead of wishing it away, figure out how to turn your newness into a strength when marketing to customers.

On an individual level: Not a good writer? Be great on camera and with video. You aren’t a fast thinker? Be known as deliberate, careful, detail-oriented. And so on. Here’s a good post on how to re-frame other limitations as strengths.

5. The values that actually shape a culture have both upside and downside

A lot of companies maintain a list of values that are all sweetness and light: integrity, excellence, hard work, and so on. Those are fine values to put on posters and hang in the corporate cafeteria, but they aren’t what really define a culture, says Reid. The values that matter offer clear pros and cons, clear upside and downside. Just as there’s no great opportunity without risk, there’s no decisive culture-shaping value that also doesn’t have drawbacks.

In the early days of LinkedIn, for example, there was no kool-aid drinking. The internal narrative was not rah-rah-rah we’re-destined-for-greatness. When things weren’t going well, Reid and the execs and employees talked about it. The upside to this honesty-first approach was that it led to useful introspection. The entire company could collectively problem solve around the key challenges. The downside to this approach had to do with morale. Indeed, some very talented people sold their stock early and left the company because they didn’t think the business had a future. A decisive cultural trait: full transparency with the entire company about both the good and bad.

At PayPal, one cultural trait was: “Let the best idea win.” No answer or idea at PayPal would be taken at face value. Instead, the idea’s proprietor had to argue vigorously and withstand critiques from colleagues. The upside: analytical rigor tends to produce better ideas than “this is the way it’s always been done” or “the CEO said so.” The downside: a confrontational interpersonal culture can stress relationships at work and undermine possible collaboration. Moreover, this cultural undercurrent was effectively “anti-experience”: it was a harder place for experienced people to operate because they had to re-prove themselves.

A more general case of the PayPal example is the extent to which a company is autocratic versus democratic in its decision making. This tends to be a defining cultural trait even though you’ll never see it noted on a company’s “About Us” web page.

I don’t believe there are “good” corporate values or “bad” corporate values–beyond the obvious. Many different types of cultures have produced successful companies. What’s important is to understand the values at work that actually shape your company’s behavior and to understand the tradeoffs involved. And if you’re applying for a job at someone else’s company, be sure you understand the true culture that you’d be working in.

6. Understand someone’s “alpha” tendencies and how that drives them

Reid sometimes parses people by how “alpha” they are—in other words, their level of focus on, and the pleasure they take from, traditional markers of status / power. Are they totally alpha? Do they have alpha streaks? Are they a repressed alpha? I’ve heard Reid put men and women in each of these three buckets. If you want to effectively partner with someone in business, it’s useful to understand where on this spectrum they fall.

A “total alpha” is someone who needs to be the top dog and exhibits all the stereotypical alpha male/alpha female behavior. Classically, total alphas need to be CEO or the highest possible job title, even if those positions aren’t the best fit for them. When selling someone in this camp on an opportunity, emphasize their power role. Keep in mind that sometimes their raw hunger for status will overpower their thinking and they’ll neglect paths that would better serve their long term self-interest.

Someone with “alpha streaks” has alpha tendencies but can manage them. He put me in this camp and I think he’d put himself here, too. His ability to manage his alpha streaks partly explains why his partnership with Jeff Weiner at LinkedIn has worked well. Reid was able to acknowledge he needed to hire a CEO to replace himself, which is not a realization every founder can come to terms with. Jeff was comfortable having a smart, influential founder still active at the company as executive chairman, which is not a dynamic every CEO can stomach. Both are supremely talented; both have managed their alpha tendencies in such a way that enable their epic partnership to flourish.

A “repressed alpha” is someone who craves status but thinks he doesn’t. Classic do-gooders sometimes fall into this category. For folks of this disposition, remember to accommodate their unconscious alpha instincts. And expect them to sometimes engage in reactionary behavior if they don’t feel like they’re getting the respect they deserve. They may bluntly and surprisingly try to assert power or status apropos of nothing in particular—it takes people by surprise, but it’s the momentary, messy manifestation of repressed alpha tendencies.

7. Self-deception watch: Even people who say they don’t want or need flattery sometimes still need flattery.

I’ve written elsewhere about why to be wary of relying on someone’s own description of their motivations and abilities. That’s because self-deception is part of human nature. We cast ourselves as heroes in our own life stories. We wrap self-serving narratives around the things that happen to us. We overstate our strengths.

Reid is a student of self-deception behavior and builds mental models for specific people and the areas where there tends to be a gap between their self-perception and reality. One common case of this has to do with flattery.

Reid once told me a story about someone we’ll call Robert. Robert was struggling to build a relationship with someone we’ll call Powerful Paul — both friends of Reid. Powerful Paul is indeed a very powerful person in the software industry today. Robert and Paul were working on a project, but they were butting heads. They weren’t getting along. Robert didn’t understand why.

Many of the super successful class think they are “over it” in terms of receiving praise and awards. Reid explained that Paul, now a legend in the industry, has this self-conception. Compliments do nothing for him anymore, Paul says; he’s heard enough nice things in his life about his intelligence. Begin to flatter him and he’ll say, “Oh stop, you don’t need to say those nice things about me. Come on–we’re peers!” Actually, Paul is deceiving himself. Paul expects people to kiss his ring. Paul expects some amount of deference or due recognition of his superior status before he’s ready to partner with a lower status professional.

Robert wasn’t kissing the ring, Reid told me. Robert accepted Paul’s assertion of humility at face value. A lot of alpha males say they don’t need the flattery or deference when in fact they do.

(Now, I should note, a lot of people think flattery is inherently manipulative. But it doesn’t have to be. As David Foster Wallace once put it, “There is such a thing as raw, unalloyed, agenda-less kindness.” Reid, for one, can practice such acts of kindness, which sometimes include extending praise without expecting anything in return. Flattery is sometimes a tool you must employ to get something done; other times it’s an agenda-less act that flows from pure kindness.)

8. Be clear on your specific level of engagement on a project

Here’s a handy way to categorize different types of engagement on a given project. Reid uses this shorthand.

Principal – You’re driving the process. You’re the person making things happen. You have ball control. Board Member – You’re probably an investor. You’re regularly meeting with the principal. You’re thinking about the project even when you’re not formally scheduled to be doing so. You’re continually up to speed on the latest and greatest. Investor – You’re a supporter (financially or with periodic bursts of time), but you’re not actively involved in the project. You’ll meet with the principal occasionally. If you’re called to do something, you have enough context such that you can be helpful on a reactive basis, but you won’t have up to date knowledge. Friend . You enjoy talking to the principal. But the moment you walk away from the breakfast or lunch – that’s it. You’re not thinking about it anymore.

Of course, the lowest level of engagement on a project is no engagement.

Next time you decide to get involved with an idea, which tier of engagement will you commit to? Clarifying this for yourself and for the other party involved can be super helpful.

9. Sketch three possible outcomes for a project: the likely upside, likely ‘regular’, and likely downside scenarios.

If everything clicks and you even get a bit lucky, what’s the likely outcome of your project? World domination? A successful product launch? A bestselling book? If this “upside” case isn’t very compelling, you might not want to embark on the project in the first place—or at least you might calibrate the level of investment. The upside case for what you’re working on needs to be exciting.

If things go fine but not great, what’s the ‘regular’ scenario look like? To use a golf metaphor, if you hit the fairway – not the green, not the rough, just the fairway – with your effort, what happens?

If your project stalls or goes sideways, what’s the downside case look like? Is it mortal – i.e., are you dead (reputationally, financially, etc.) Or is the downside quite survivable?

When Reid, Chris and I brainstormed The Alliance book project, we talked through these scenarios. The book was going to take substantial investment. What would the upside case look like (broad impact with real companies adopting the management framework) and how would we feel about that? What would the fairway scenario look like (a flash-in-the-pan impact with no real implementation) and how we would feel about that? What would the downside look like (negative reviews, reputational damage)?

When you align around three simple scenarios, as a team, you can calibrate your expectations and investment thesis accordingly.

10. A key to making good partnerships great: Identify and emphasize any misaligned incentives

The first negotiation Reid and I led together was with our publisher for The Start-Up of You. Reid reminded me to think about where our incentives were aligned with the counterparty and where they were misaligned. Even in a broadly mutually beneficial deal, there will usually be particular points of misalignment. For example, in our Random House contract, their incentive was to sell books, whereas our interest was broader: spread an idea into the world, in any format possible, at more or less any price. Accordingly, we were more interested than they were in giving away of e-books for free. This misalignment didn’t torpedo the deal. But being aware of it helped us better navigate the ongoing relationship.

Make misalignments explicit with yourself and the other party so that if and when they rear their head, neither side is surprised.

11. Reason is the steering wheel. Emotion is the gas pedal.

I was once at a dinner with Reid in rural Utah, prior to formally working with him. It was an intellectual retreat, and the two of us happened to be seated at the same table together. We went around the table and each of us shared a contrarian opinion about the world—as per the instructions for the dinner. (Peter Thiel was co-hosting it.) After Reid said his bit, another person at the table – a high profile executive in the advertising world – turned to Reid. “That’s not a bold view at all,” he sneered. “What an incredibly boring prediction.” He then turned his body away from the table and typed out a few emails on his BlackBerry. People were sadly unsurprised at his rudeness—this guy had been acting like a jackass all night. Reid calmly replied, “I’m perfectly willing to accept that.” And we all moved on. Not everyone can remain composed when an insult is hurled at one’s face.

Of course, the test usually isn’t how you respond to being insulted to your face since that’s rare in polite business. Usually, emotionally enraging situations creep up incrementally over a series of annoying emails or brain-dead meetings. One day, the proverbial straw breaks the camel’s back, and you shoot off that ill-advised email or bark a sarcastic comment on a group conference call that makes the line go quiet.

Reid has a gift of being the opposite of impulsive. Call it being deliberate. Or thoughtful. Or restrained in the face of volatility. So many people let these emotions infiltrate their reasoning process. Reid integrates his emotional reaction into the reasoning process. His passions are a slave to reason, as much as it can be for a person. (It’s worth noting that this disposition is the opposite of Steve Jobs—which shows how many different models of success there are.)

I like to say that when making decisions, think of reason as the steering wheel and emotions as the gas pedal. You need emotions in order to be decisive in making a great decision, as various research has shown, but you also need to direct that emotional decisiveness in the right way. Reid is as good as anyone at steering the driver’s wheel in the right direction, and then deploying the right amount of emotional energy in that conscious direction.

I’m not sure if learning how to steer and press the gas pedal is a skill that can be learned or a temperament that can be cultivated. Or if it’s something more innate.

12. Trade up on trust even if it means you trade down on competency.

Should you start a company with friends? All things being equal, Reid says yes, because you can move more quickly with trusted friends because you already understand how each other thinks and talks. And moving quickly? That’s critical in the early days of a startup.

But what if all things aren’t equal? If you’re choosing between working with someone who’s a trusted friend and a 7 out of 10 on competence, versus a stranger who’s a 9 out of 10 on competence, who should you pick? Answer: if the trusted friend is a fast learner, pick the trusted friend.

Trade up on trust, even if it means you have to trade down on competency a bit. In other words, choose to work with someone you know who’s a fast learner over someone who’s a bit more qualified who you do not know. Assuming the person you know and trust is in Permanent Beta, he or she can round out their gaps in skills or experience in short order.

I benefitted from Reid’s philosophy on this personally. For some assignments, I was not the most qualified person in the world, or even the most qualified within his own network. But given that we a) completely trust each other, b) I have a good sense of his priorities and values and preferences and he has a good sense of my own priorities and values and preferences, and c) I’m a quick learner, we could move at lightning speed together on projects.

As with so many lessons, I have to continue to re-learn this one. The first time I learned this lesson the hard way at one of my early companies, when we hired someone who looked great on paper in terms of industry accomplishments but who none of us really knew or trusted. The moment we encountered a couple landmines, the lack of trust ruined any hopes at productive group problem solving. The second time I learned this the hard way was at a different company I co-founded, where I traded down on competency too much when bringing on one team member. The trust was all there, and the guy was a fast learner, but the tradeoff down in necessary expertise wasn’t worth it, and the project floundered.

13. Tell the truth. Don’t reflexively kiss ass to powerful people.

Shortly after I began the Chief of Staff job, Reid and I hosted a dinner in Palo Alto for some friends. I drove one of the guests, Charlie Songhurst, back to his hotel afterwards. I’ve known and respected Charlie for years. At the time, he was wrapping up a tour of duty as a head of corporate strategy at Microsoft and advisor to Steve Ballmer. As I told Charlie about how I was trying to help Reid, he told me something I didn’t forget: “My job is basically to tell the truth to Steve. You need to do the same for Reid.” I took that to heart. And Reid said he appreciated that.

It’s no surprise that there’s a direct correlation between how much power you have and how much people kiss your ass. Public intellectuals like Reid, who are on a hunt for truth and wisdom, are driven crazy by the nonstop ass kissing. Professionals in permanent beta—those who seek constant professional and personal growth—also know that they only improve when they get constructive feedback. Yet most people offer mindless praise (“You were amazing!”). Slavish yes-men are not useful.

So people like Reid end up relying on friends and colleagues who feel secure enough in their relationship that they’ll say what they actually think. If you have the courage to deliver honest feedback to a powerful person, you can earn respect and attention. One time, a consultant emailed Reid and one of his Greylock partners and told them that he thought their joint performance at a conference was a C in quality. It got their attention—they hadn’t received a C grade in a long time! And I think they respected him more for it.

Now, as per an earlier point, everyone enjoys being flattered, and indeed many successful executives still yearn to be liked. You need to deliver feedback constructively and not assume that someone powerful lacks basic feelings.

14. Respect the shadow power

Reid and Steve Ballmer, then CEO of Microsoft, were set to speak on stage together at a fireside chat hosted by the Churchill Club. Backstage beforehand, we were reviewing the flow and talking points for the evening. When I entered the room for the pre-event huddle, Steve got up and extended his hand, “Ben, Steve Ballmer. Nice to meet you.” He was completely present. I was quite taken with how nicely he treated me.

Later in the year, Reid hosted a prominent Silicon Valley figure for a similar fireside chat. The man was accompanied by a press flak. The man himself said hello to me and chatted me up as friendly as ever. His flak did not acknowledge me—she pretended like I did not exist. And after the event, she said goodbye to Reid and then promptly exited the building with her boss. I found it telling that the main guy perceived me more respectfully than his flak.

This is not about me—I wasn’t kept up at night because some PR person didn’t acknowledge me. The point to those seeking to do business with poo bahs is to not underestimate the influence of shadow power—advisors, assistants, consultants, and most especially spouses. To be rude to them is to doom your chances at making progress with the man or woman at the center of the circle. The more powerful the person, the broader the circle, and the more the shadows loom.

15. Make people genuine partners and they’ll work harder

In the Start-up of You, we write about how life is a team sport and that anything great in your life will only happen with and through other people. Reid is a master at bringing people together to work on shared projects. And even though he often plays a uniquely pivotal role, whether as key convener or funder or original visionary or even shouldering some of the execution work, he shares credit generously.

This doesn’t mean he issues obligatory thank-yous at the end of a project; it means he makes his partners fully credited co-pilots. When people take note of times he does this, they call him generous, which he is. Or they call him ethical, because he makes sure people who do hard work get credited for it. Also true.

But what he really is is smart. He’s inclusive because he knows when people are personally invested in the public success of a project, they’ll work harder, they’ll care more, and the final product will likely benefit (which also benefits his reputation). I’ve seen Reid do this with partners at Greylock, executives at LinkedIn, and with me in the two books we co-authored. As a co-author instead of a ghostwriter I felt far more committed to the project than I would have otherwise and the quality improved accordingly.

Along these lines, I’m often surprised when founders of companies shy away from offering the co-founder title to early founding team members. Their egos get them wrapped up in what it really means to be a “founder” and they forget that so long as it’s directionally true, you gain a ton in the way of motivation and commitment from those who receive the title. Share credit. Make people genuine partners. You’ll go farther faster.

16. Final lesson and reflection: The people around you change you in myriad unconscious ways

The lessons I’ve described above are all good and instructive, but they are discrete and easily describe-able. They are finite.

Yet, when I take stock of the past four and a half years, what I’ve learned from Reid feels more all encompassing than a tidy set of specific lessons. The learning feels more infinite. When you are fully enmeshed in another person’s life, when your job at one point is to look at the world from his perspective every single day—that person’s impact on you becomes so foundational that it’s hard to disentangle where his influence starts and stops.

I’m reminded of interviews with professional athletes, who, when reflecting on their most important coaches, say that more than learning how to hit or pitch or catch, they learned how to play the game right.

And so, there’s one more final lesson learned: the people you spend the most time with will change you in ways you cannot anticipate or ever fully understand after the fact. The most important choice of all is who you choose to surround yourself with.

I feel incredibly lucky to have learned so much from such a special man. May we all have the opportunity to partner with and learn from the special people in our lives. May we all take the time to savor this amazing world. And may we all have the wisdom to try to save it a little, too.

(Thanks to Greg Beato, Shannon Stubo, John Lilly, Ray Batra, Jessie Young, Brett Bolkowy, Stephen Dodson, and David Sanford for their feedback on this essay. You can email me any feedback, questions, or requests at [email protected] I always love to hear from interesting people working on interesting things.)