The Privilege of Directness: Why Bold Moves Beat Polite Hesitation

There's a particular kind of paralysis that afflicts smart people in business, this learned hesitation that masquerades as professionalism but is really just fear dressed up in business casual. You have a question about a company's financials, so you spend three hours researching online, parsing through outdated investor decks and analyst reports, trying to reverse-engineer information that someone could just tell you in five minutes. You're concerned about a startup you've invested in, so you wait for the quarterly update email instead of just showing up at their office to see what's actually happening. You notice a strategic direction that seems misguided, so you draft a carefully worded email that takes forty-five minutes to compose and says nothing of substance because you're terrified of seeming presumptuous or overstepping boundaries that don't actually exist. And meanwhile, opportunities evaporate, problems compound, and everyone involved wastes time dancing around conversations that should have happened weeks ago.

The alternative approach is simpler and more uncomfortable: just do the thing. Call the CFO. Not through seven layers of assistants and scheduling software, but directly—find the number, make the call, explain what you need. Show up at the startup's office unannounced. Not in an aggressive or entitled way, but with the straightforward assumption that if you have a vested interest in their success, your presence and input might actually be valuable rather than intrusive. Cut the project that's clearly going nowhere. Not after six more months of "let's give it one more quarter" or "we've already invested so much," but now, today, as soon as it's obvious that the math doesn't work and never will. The pattern isn't about being aggressive or demanding or disrespectful of other people's time and autonomy. It's about recognizing that directness, when executed with basic human decency, is almost always more respectful than the elaborate theater of professional courtesy that wastes everyone's time while accomplishing nothing.

I learned this somewhat accidentally, through a combination of necessity and watching how much time other people waste on process. Early in my career with the cryptocurrency fund, I needed to understand how a particular exchange was handling custodial arrangements because the technical documentation was either incomplete or deliberately vague. The conventional approach would have been to submit a support ticket, wait three days for a canned response, submit a follow-up clarifying the question, wait another three days, maybe eventually get escalated to someone technical, and possibly get an answer in two weeks if I was lucky. Instead, I found the CTO's LinkedIn, sent a direct message explaining exactly what I needed to know and why it mattered, and had a thirty-minute call scheduled within six hours. The information I got in that conversation would have taken months to piece together otherwise, and it directly informed a decision about whether to move forward with a significant position. The CTO didn't seem offended or bothered by the direct approach—if anything, he seemed relieved to talk to someone who had specific technical questions rather than the usual surface-level inquiries he fielded through official channels.

What surprised me wasn't that it worked, but how rare this approach apparently is. The CTO mentioned that in three years of running technical operations for a major exchange, he'd received maybe a dozen direct outreach attempts from investors or traders trying to understand the actual infrastructure rather than just the marketing materials. Everyone else apparently preferred to make decisions based on incomplete information rather than risk the minor social discomfort of reaching out directly to someone they didn't know. And this pattern repeats across every industry and every level of business—people would rather guess, speculate, waste time, or make uninformed decisions than simply ask the person who knows the answer. Not because asking is actually difficult or inappropriate, but because we've constructed elaborate social narratives about proper channels and professional protocols that mostly serve to protect people from having to engage directly with reality.

The office visits follow similar logic. When you've invested in a startup, you have access to whatever information they choose to share in updates and board meetings. But the real signal isn't in the carefully curated slide decks or the metrics that have been massaged to show favorable trends. It's in the energy of the office, the quality of the conversations happening at desks, whether the founders look energized or exhausted, how quickly people move, what's on the whiteboards, who's actually there and who's suspiciously absent. You can't get that from a Zoom call or a monthly email. You have to show up, unannounced enough that people don't have time to stage-manage the environment, and just observe what's actually happening. And again, this isn't about being intrusive or micromanaging—it's about gathering the information you need to be useful. If the vibe is off, if something feels wrong, you can offer help or ask hard questions or make different decisions about future funding. If everything's humming, you can get out of the way and let them work. But you can't do either if you're relying solely on information that's been filtered through presentation templates and professional update protocols.

The key to making this work without being an asshole is surprisingly simple: be genuinely useful, not performatively important. When you call the CFO, have specific questions that demonstrate you've done basic homework and respect their time. When you show up at the startup, bring something valuable—an introduction, a perspective, a solution to a problem they mentioned last time, or at minimum genuine interest in what they're building rather than just monitoring your investment. When you cut a failing project, do it clearly and directly but without unnecessary cruelty or blame—the goal is to stop wasting resources, not to make people feel bad about having tried something that didn't work. The directness isn't about asserting dominance or demonstrating that you can do whatever you want because of your position. It's about operating at the actual speed of business rather than the theatrical speed of business process, and doing so in a way that treats everyone involved as adults who can handle straightforward communication.

There's also a critical distinction between being bold and being reckless, between directness and thoughtlessness. Calling the CFO works because you've identified a specific information need that they're uniquely positioned to address and that matters for a real decision you're making. It wouldn't work—and would rightfully be seen as obnoxious—if you were just calling to chat or to demonstrate that you have access or to ask questions you could easily answer yourself through minimal research. Showing up at the startup unannounced works because you have a legitimate interest in their success and can provide value beyond just writing checks. It would be intrusive and counterproductive if you were just checking up on them because you don't trust them or want to assert control. Cutting failing projects quickly works because you've actually analyzed the situation and concluded the fundamentals don't support continuation. It would be destructive if you were just impatient or unwilling to work through normal challenges that every project faces. The boldness has to be in service of something real—better information, faster correction of problems, more efficient allocation of resources—not just in service of your ego or your desire to feel important.

What makes this approach particularly effective is how it compounds over time. When you develop a reputation for directness executed well—asking good questions, providing useful input, making decisions quickly based on actual information—people start being more direct with you in return. The CFO you called six months ago now calls you when they're thinking through a complex situation because they know you'll give them a straight answer rather than a politically safe non-answer. The startup founders you've visited actually tell you when things are going poorly because they trust you to be helpful rather than just critical. Your team stops bringing you marginal ideas because they know you'll kill them immediately, which means they spend their time developing stronger concepts instead. The whole system becomes more efficient, more honest, more focused on substance rather than performance. And this isn't about being intimidating or creating fear—it's about building relationships based on actual communication rather than the elaborate pretense that characterizes most professional interactions.

The "not spending time on pointless ideas" aspect deserves particular attention because this is where most organizations hemorrhage resources while pretending to be thoughtful or inclusive. Someone proposes a new initiative that sounds interesting in the abstract but that five minutes of serious analysis reveals won't work because the unit economics are broken or the market doesn't exist or the execution requirements exceed available capability. The conventional response is to have a series of meetings, maybe commission some research, possibly run a small pilot, definitely spend several months of multiple people's time before eventually arriving at the conclusion that was obvious from day one. The bold response is to kill it immediately, not rudely or dismissively, but with clear explanation of why the fundamentals don't work and what would need to change for the idea to become viable. This saves enormous amounts of time and emotional energy for everyone involved, and it creates space to actually explore ideas that might work rather than slowly suffocating good initiatives under the weight of bad ones that won't die.

The hardest part of this approach for most people isn't the directness itself—it's overcoming the internalized narratives about what's appropriate or professional or respectful. We've been trained to believe that going through proper channels is courteous, that waiting for information to be formally shared is respectful, that being direct is somehow aggressive or presumptuous. But these beliefs mostly serve to protect comfortable mediocrity and waste everyone's time. The CFO doesn't actually care about proper channels—they care about whether you have a legitimate question and whether answering it is a good use of their time. The startup founders don't need you to wait for scheduled updates—they need you to be engaged enough to actually help when problems arise. Your team doesn't want you to pretend bad ideas might work out—they want clear direction so they can focus their efforts on things that actually matter. The directness, executed with basic consideration and genuine intent to be useful, is almost always more respectful than the elaborate performance of professional courtesy.

There's also something liberating about operating this way, about cutting through the noise and just dealing with reality directly. You stop wasting emotional energy on whether it's appropriate to make the call or send the message or show up at the office. You stop second-guessing decisions that are obviously correct but that feel uncomfortable because they're direct. You stop participating in the collective fiction that formal processes and proper channels are serving anyone's interests when they're mostly just creating friction and delay. This doesn't mean you become inconsiderate or stop thinking about how your actions affect others. It means you start evaluating those effects based on actual impact rather than theoretical propriety—is this action helpful or harmful? Does it create value or just demonstrate power? Is it solving a real problem or satisfying my need to feel important? When the answers to those questions are right, the boldness becomes not just acceptable but necessary.

The resistance to this approach usually comes in two forms, both of them revealing. First, there are the people who are genuinely concerned about social dynamics and relationships, who worry that directness will damage connections or create conflict or make them seem aggressive. This is a reasonable concern that deserves consideration, but it's almost always overstated. Most people actually appreciate directness when it's combined with basic respect and genuine competence. They don't want you to waste their time with elaborate preambles and careful positioning. They want you to get to the point, explain what you need, and let them decide how to respond. The key is calibration—you have to actually be competent and actually be offering value, not just demanding attention because you think you're important. But when those conditions are met, directness strengthens relationships rather than damaging them because it's based on honesty and mutual respect rather than the performance of deference.

The second form of resistance is more interesting because it's more self-serving. These are the people who benefit from the current system of processes and channels and formal communications, either because it gives them gatekeeping power or because it protects them from having to actually perform at a high level. They'll invoke professionalism and respect and proper procedure, but what they really mean is "don't circumvent the systems that give me influence" or "don't expose the fact that I'm not actually adding value." These people will never be convinced by arguments about efficiency or effectiveness because the inefficiency is the point—it's what creates their role and justifies their position. The only effective response is to just bypass them, not in a hostile or confrontational way, but simply by operating at a different level and demonstrating through results that the direct approach works better. Eventually, organizations either adapt to reward directness and effectiveness, or they ossify under the weight of their own processes and get disrupted by competitors who move faster because they spend less time on theater.

What's particularly valuable about internalizing this approach early in your career is how it shapes the opportunities that become available to you. When you're the person who can get clear answers quickly by just asking the right people directly, you become someone others turn to when they need information. When you're willing to show up and engage directly with situations rather than managing them from a distance, you develop much deeper understanding of how businesses actually work rather than how they're supposed to work according to org charts and process documents. When you can kill bad ideas quickly without creating drama or damaging relationships, you become someone who can be trusted with resources because you won't waste them on obviously unworkable plans. These capabilities compound over time, creating a career trajectory that's fundamentally different from the one available to people who spend their time navigating processes and managing optics rather than just doing the work.

The "doing it nicely" part isn't some separate skill you layer on top of directness—it's integral to why the approach works. You can be direct without being an asshole by genuinely respecting the people you're interacting with, by being competent enough that your directness is actually helpful rather than just disruptive, and by caring about outcomes rather than just demonstrating your ability to do whatever you want. When you call the CFO, you're respectful of their time by having specific questions rather than vague inquiries. When you show up at the startup, you're respectful of their autonomy by offering help rather than just surveillance. When you cut a failing project, you're respectful of the people who worked on it by being clear about why it's ending rather than letting it die slowly. The niceness isn't about softening the directness or making it more palatable—it's about ensuring that the directness is actually in service of something useful rather than just your ego or your desire to feel powerful.

There's also a speed component to this that matters more than people realize. Markets move, situations evolve, opportunities close. The three weeks you spend trying to get information through proper channels is three weeks when conditions might change, when competitors might move, when the window for effective action might close. The six months you spend slowly killing a project that should have died immediately is six months of talent and capital that could have been deployed on something viable. The quarterly update cycle you rely on for information about your investments is too slow to catch problems when they're still fixable rather than catastrophic. Bold doesn't just mean willing to take action—it means willing to take action at the actual speed that reality demands rather than the comfortable speed that processes allow. And this speed differential compounds dramatically over time, creating outcomes that look like luck or exceptional insight but that are really just the result of operating in real-time rather than in process-time.

The thing that eventually becomes clear, if you stick with this approach long enough, is that most of the resistance to directness isn't actually about the directness itself. It's about the accountability that directness creates. When you call the CFO directly and get a clear answer, you can't later claim you didn't have access to information. When you show up at the startup and see what's actually happening, you can't pretend problems weren't visible. When you kill a bad project immediately, you can't spread responsibility for the decision across months of meetings and multiple stakeholders. Direct action creates clear responsibility, which makes some people uncomfortable because it removes the protective ambiguity that allows everyone to claim credit for success while avoiding blame for failure. But that clarity is exactly what makes organizations effective. Someone actually decides. Someone actually acts. Someone takes responsibility for outcomes rather than just managing the process that leads to outcomes. And while that's uncomfortable for people who've built careers on navigating ambiguity, it's essential for anyone who actually wants to build something or solve problems or create value rather than just occupy space in an org chart.

So the pattern isn't complicated, even if executing it consistently requires some courage and a certain comfort with occasional social awkwardness. When you need information, go directly to the source rather than inferring from indirect signals. When you need to understand a situation, show up and observe rather than relying on curated reports. When something isn't working, kill it quickly rather than letting it consume resources while everyone pretends it might still succeed. Do all of this with basic human decency and genuine respect for the people involved, but don't confuse respect with the elaborate performance of deference that mostly just wastes time. Be useful, be competent, be direct. The people worth working with will appreciate it because it makes everyone more effective. The people who resist it are usually either protecting their position or uncomfortable with the accountability that comes from operating in reality rather than in process. And the outcomes—better information, faster course correction, more efficient resource allocation, stronger relationships based on actual communication rather than professional theater—will compound over time into a career and a set of capabilities that look almost magical but that are really just the result of consistently choosing directness over comfort, action over process, and reality over the elaborate fictions we construct to avoid dealing with it.