2. (Credit: Wired magazine. )
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
3. 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
4. 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
5. 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?
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.
6. 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
7. 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.)
People are complicated and flawed. Root for their
better angels.
1.
The best way to get a busy person’s attention: Help
them.
2.
Keep it simple and move fast when conceiving
strategies and making decisions.
3.
Every weakness has a corresponding strength.4.
The values that actually shape a culture have both
upside and downside.
5.
Understand someone’s “alpha” tendencies and how6.
8. that drives them.
Self-deception watch: even those who say they don’t
need or want flattery, sometimes still need it.
7.
Be clear on your specific level of engagement on a
project.
8.
Sketch three possible outcomes for a project: the likely
upside, likely ‘regular’, and likely downside scenarios.
9.
A key to making good partnerships great: Identify and
emphasize any misaligned incentives.
10.
Reason is the steering wheel. Emotion is the gas pedal.11.
Trade up on trust even if it means you trade down on
competency.
12.
Tell the truth. Don’t reflexively kiss ass to powerful
people.
13.
Respect the shadow power.14.
Make people genuine partners and they’ll work harder.15.
Final: The people around you change you in myriad
unconscious ways
16.
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
9. 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
10. 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.
11. 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.
12. 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.
13. 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
14. 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
15. 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.
Reid and Mark Zuckerberg spent a lot of time in 2013/2014
focused on immigration reform. There were ups and downs and
the fight for real reform continues, but a highlight was Linkedin
hosting a hackathon for “DREAMer” immigrants. They were
16. inspiring.
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
17. 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
18. 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
19. 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
20. 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.
1.
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.
2.
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.
3.
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.
4.
Of course, the lowest level of engagement on a project is
no engagement.
21. 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)?
22. When you align around three simple scenarios, as a team,
you can calibrate your expectations and investment thesis
accordingly.
A group shot with my colleagues who worked for Reid. I have no
idea what I’m doing with my fingers.
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
23. 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
24. 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
25. 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
26. 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
27. 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
28. 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
29. 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
ben@casnocha.com. I always love to hear from interesting
people working on interesting things.)
