What Leaders and Managers Can Learn from Mastering the VC Game
Dana needed budget for a new hire and walked into quarterly planning with a polished deck, pitching the finance committee cold. They asked questions she hadn't anticipated and tabled the decision. Her peer Sam wanted headcount too, but had spent the prior quarter looping the CFO into informal talks about his team's bottleneck, sharing early data before any formal ask existed. When Sam's request came up, it felt like a formality, because the relationship had already done the persuading. Dana got her hire eventually, but she noticed the difference: one of them had built trust before asking, and one had tried to build it in the room, under a deadline, with a slide deck standing in for a relationship that didn't exist yet.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Building sponsors before you need one
The leaders who get resourced quickly are rarely the ones with the best slide deck in the room; they are the ones whose stakeholders already understood the problem before the meeting started. That means bringing your boss, your peers, and your finance partners into your thinking early and often, not saving the whole story for a single formal ask when you need something from them.
Leaders who only surface a problem when they need approval to fix it come across as reactive, and stakeholders respond to that surprise with skepticism rather than support.
Identify one decision you will need approval for in the next quarter and start a running, informal thread about it with the key stakeholder this week.
Choosing the right ally, not just the most powerful one
When you need a sponsor, the most senior person in the room is not automatically the right one; the right sponsor understands your function, has bandwidth to engage, and will still be around when the initiative hits its inevitable rough patch. Chasing prestige over fit leaves you with a sponsor who shows up for the launch and disappears when trouble starts.
Leaders court the most visible executive rather than the one who will actually stay engaged, and discover the gap only when they need real support and get a form response.
Before naming a sponsor for your next initiative, ask yourself who has actually shown up for a peer's project when it struggled, not just when it succeeded.
Running the ask like a real process
A resourcing request deserves the same discipline as a formal pitch: a clear narrative, the right sequence of conversations, and a defined decision point, not an improvised appeal dropped into a crowded agenda. Leaders who treat internal asks casually get casual, delayed answers.
Managers raise a request once, get a vague non-answer, and let it drift for months instead of following a deliberate sequence toward a decision.
Map out who needs to say yes to your next request, in what order, and schedule each conversation before the formal meeting where you'll ask.
The partnership continues after the yes
Getting the headcount or the sponsorship is not the end of the relationship, it is the start of an ongoing one you will need again. How you report progress, flag risk early, and keep your sponsors informed after the decision determines whether the next ask is easy or starts from zero.
Sometimes the fastest path to a yes is pitching the most senior person available, even when they are not the best long-term ally for the work, and a leader under deadline pressure will feel that pull strongly. Resist it by asking whether this person will still be useful to you three asks from now, not just this one.
Name one thing, honestly
Which upcoming request are you planning to make cold that would land better if you started the conversation today instead?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Map out who needs to say yes to your next request, in what order, and schedule each conversation before the formal meeting where you'll ask.