Scale Your Boss
Your job is to make your boss's job easier — and information is the highest-value thing you can hand them.
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 85%
Asked how anyone could build a relationship with someone as in-demand as Gary Vaynerchuk, Silver's answer is unromantic: her job has always been to make her boss's job easier. She does that by asking, anticipating, doing what she thinks is the right move and accepting the correction — and, most importantly, by giving the senior leader information. Her role, she says, is set up to scale him, because he is the CEO and the COO and everything else, and he cannot be in all those places at once with that magnitude of people. What he needs is to know how the culture is doing, what is going on on the floor, what people are saying. Giving your leader information, plus taking things off their plate, is in her view the best thing you can do.
Origin
Silver met Vaynerchuk in August 2013 while living in London, with instant chemistry — like meeting each other's brother or sister. But she credits the durability of the relationship not to the chemistry but to the value she supplies: as VaynerMedia grew to hundreds and then 800 people, her role became the instrument that let one founder still know his own company.
Core principles
- 01Your role exists to scale the person above you — they cannot be in all places at once.
- 02Information is what a leader is starved of most as headcount grows.
- 03Anticipate and act, then let the correction come — don't wait to be told.
- 04Taking things off their plate is the second-best gift after information.
- 05The relationship thrives on the value you provide, not the chemistry you started with.
How to run it
- 1
Diagnose what your leader cannot see
Map the roles your leader is carrying and where that leaves them blind. Silver's read on Vaynerchuk: he's the CEO, the COO, all of those things, it's his company, and he can't be in all those places at once.
- 2
Make information the deliverable
Bring back the answers to the questions they can't ask at scale: how are we doing, how is this culture doing, what's going on on the floor, what are people saying, are people thriving.
Pro tip Silver's view is that giving your CEO or c-suite information is the single best thing you can do for them.
Watch out Information means ground truth, including the uncomfortable. Filtered good news is worthless as a scaling instrument.
- 3
Anticipate, act, accept the correction
Provide value by asking, anticipating, and doing what you think is the right move — then being told yes that was right, or no don't do that next time. The correction is the calibration loop.
Watch out Waiting for instruction on everything makes you a cost, not a scaler.
- 4
Take things off their plate
Alongside information, remove work. Silver names it as the other half of the equation for what you can do for a leader.
In the wild
Silver frames her Chief Heart Officer role as literally set up to scale Vaynerchuk — he's the CEO, COO and everything else at a company of 800, so she becomes the way he still knows how the culture is doing and what people are saying on the floor.
→ A relationship that continues to thrive because it is built on supplied value, not on competing for a busy founder's attention.
Common mistakes
Optimising for access instead of value
Everybody wants a high-profile leader's attention at all hours. Silver's route in wasn't asking for time — it was supplying what he couldn't get himself.
Attributing the relationship to chemistry
Silver had immediate chemistry with Vaynerchuk from their 2013 meeting, but explicitly redirects the question to the value mechanism. Chemistry opens the door; information keeps it open.
Is it for you?
Best for
Chiefs of staff, deputies and second-in-commands to a founder or CEO who is stretched across too many roles.
Not ideal for
Roles with no line of sight into what the leader can't see, or leaders who don't actually want ground truth.
From the transcript
“my job has always been to make my boss's job easier and how do I do that how do I provide value is either by…”
“my role is set up to scale him period to scale him because he is the CH oh let's be honest he's the CEO he's…”
“he needs information he wants to know how are we doing how is this culture doing what is going on on the floor what are…”
“giving your CEO or your c-suite your leaders information I think this is the best thing you can do aside from taking things off of…”
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