How to Give Authority Without Losing Control

Failing to delegate will kill your startup... and possibly you in the process.

This week, we’re talking:

• How to delegate without losing control 👉🎯

• How to earn authority 💪⚡

• TikTok’s looming US closure on Sunday… and who the early beneficiaries are 📱🪦

• The Loneliness Epidemic caused in no small part by tech 🤝 the tech entrepreneurs trying to solve The Loneliness Epidemic 📱🚶🏻📱

• Justice Alito’s viral question 👀 👀 👀

• Can a convicted terrorist be rehabilitated? Michelle Shepard’s magnum opus tries to answer just that ⛓⛓

• How quickly Big Tech has flocked to Trump 🤖👱‍♂️

My Take:

There’s a school of thought pushed by the world’s richest man that you need to be ‘hardcore,’ sleep at the office, and emulate his family relationships if you want to succeed in business. I couldn’t disagree more.

Let’s lay aside the fact that, like just about everyone, he exaggerates the number of hours he works. There’s no way you become one of the world’s Top 5 Diablo IV players, send 400 tweets/day, and drop into random dinners at Mar A Lago while putting in 90 hours of actual company work per week. The larger issue is that, even if he were working 90 hours per week, it’s not the reason his companies are successful. Demanding 80 hours per week from employees doesn’t result in scalable, sustainable companies (though it can certainly lead to resignations that reduce cost and stave off more expensive layoffs).

Years ago, I ran a company that conducted its Series A in June 1999, at the height of the dot-com bubble. The market crashed, our core vertical imploded, and investors freaked (not all of them, thank God). I found myself at the helm of a company that would proceed to conduct three rounds of layoffs and a major pivot before ultimately achieving a reasonably successful exit. It was a punishing but powerful experience.

I learned a ton about conquering fear and hedgehogging through tough business conditions. Like many first-time entrepreneurs, I threw myself into every detail, every problem, every ditch, every product spec, every customer call. I was drunk with work. The company consumed nearly every gram of my energy, will, and brainpower.

There’s a story my colleagues still tell that makes me cringe. We were about to ship a major software release (yes, back in the days when people actually “shipped” software). During a three-week death march, with our anchor customer waiting to be dazzled on Tuesday, my team left the office at 2:30 a.m. on a Saturday night. Five hours later, at 7:30 a.m. Sunday, I was back in the office, enraged when people didn’t show up by 8. By 8:30, I was on the phone, calling engineers and yelling at them to get their asses to the office. Mihir, one of the gentlest souls in the universe, answered my call and calmly said, “Tom, I’m having breakfast with my wife. I’ll be in the office in 45 minutes.” Click.

I’m not proud of the things my former self did, but the pain and chaos were instructive. I had a lot to learn—most importantly, about managing my own psychology. At 32, I realized I was on the cusp of a heart attack. And if I didn’t die from a coronary event, my team would certainly finish the job with gusto.

I knew I needed to change. For the company to grow and for me to survive, I couldn’t know every detail and solve every problem. I had to let go of the control I was white-knuckling and give my team the authority to get the job done.

The Cost of Over-Control

Over-control almost killed me—literally. My approach to leadership then was to be involved in every detail and every decision, which led to burnout for me and my team. The “death march” story exemplifies the toxic cycle of overwork and micromanagement that stifles creativity, alienates employees, and hinders scalability.

I began to realize that I needed to shift my mindset. If I didn’t trust my team, how could they trust themselves? That shift was the first step toward a new approach—one that saved my health and transformed the way I led.

The Power of Giving Authority

Giving authority is about painting the target, inspiring your team to aim for it, and then stepping back. It requires trust, a willingness to let go, and the ability to ooze conviction so your team believes in themselves.

Pretty amazing things started to happen when I learned to trust my team. People who’d been acting like docile puppies started operating like confident doers. Several employees discovered their inner ninja, assumed greater responsibility, and ultimately crushed it. The company scaled and grew. I didn’t die, I even got to know my kids better, and even enjoyed weekends off now and then. Investors and employees were happy.

This transformation carried over to my next company, where I saw firsthand how empowering others led to exponential growth. But not every delegation story had a happy ending.

The Risks of Giving Too Much Authority

At my second company, a key employee raised his hand and insisted he was ready to operate at the next level. We gave him a significant project and vested him with decision rights. Five months later, we discovered he had utterly failed—but with Bernie Madoff-like mastery, he had kept the magnitude of his failure hidden from view.

The experience was painful for the entire company, but it was also illuminating. Give people authority and they can run with it but giving unchecked authority can pose serious -- even existential -- operational risks. The entire incident left me with a critical question: How do you balance giving too much authority versus too little?

Balancing Autonomy and Oversight

From the Employee’s Perspective
Employees often hunger for more autonomy, but ambition must align with readiness.

• Earn Authority: In the old, command-and-control model that all of us in Silicon Valley generally despise, a Boss needed to establish or follow a Process to allocate work and assign objectives. In the model followed by successful Silicon Valley companies, employees who want to rise up and assume more authority don’t ask for permission. In fact, if you’re asking for permission or agitating for more authority, by definition you’re likely not ready for it. Ambitious doers find ways to exert greater impact by just picking up more of the load without a formal “Process” or request for approval. When you’re ready for the Big Project, it will be obvious to your boss and colleagues.

• Seek Clarity: If you’re pushing for more authority than you’re receiving, your ambition might be outstripping your capability. You still might have to prove your mettle before getting the next promotion or the next big project. It’s time to sit down and have a plain-spoken conversation with your boss where you seek total clarity on what he or she needs to see you do so that you can get to that next valence.

• Manage Up: Take the initiative to update your boss on progress and milestones. Specify next steps and invite critique or ratification to enroll your boss in your success.

From the Boss’s Perspective

• Help Employees Break Imaginary Boundaries: Young employees are often eager to please but hesitant to act without explicit instructions. When they’re stuck, it’s helpful to say, “If I’m doing something that makes you feel you can’t just tackle this issue, let me know—because that’s not who I want to be when I grow up.” This often helps employees realize they’re imagining constraints that don’t actually exist, empowering them to snap out of hesitation and get back to work. A boss’s job is to create the conditions for success—not to control every detail.

• Focus on Social Architecture: Tech founders frequently focus on technical and product architecture to the exclusion of social architecture. Great social architecture encourages employees to rise up and achieve great things without point-to-point direction. Your role as Boss is to empower them to do the right thing and make smart decisions, not to micromanage them or frighten them into paralysis or submission. As a leader, it’s less about giving assignments and more about fostering a shared sense of ownership and agency across the team.

• Ask, Don’t Declare: Instead of dictating, ask your team, “What do you think we should do?” This encourages ownership and builds confidence.

• Articulate Outcomes: Clearly define the date and the outcome without over-specifying the means to achieving it. Avoid vague directives that leave employees guessing.

• Provide Support: Show unwavering belief in your team while staying available for guidance. There will be moments when you need to snake in, verify that everyone is tracking to the date and outcome you’ve established, and occasionally pick up a shovel and do the damn thing yourself. But, as I learned the hard way at my first company, you need to resist the urge to swoop in and put a finger in every pie. Let the team roll.

In my first years as an entrepreneur, feeling the weight of every one of the millions of dollars I’d raised from very important people, I thought that my responsibility was to show up as the smartest guy in the room. What I learned is that my job, in fact, was just to understand who the smartest person in the room was and then to listen to and empower that person.

The art of giving authority lies in finding the Goldilocks zone between too much and too little. It’s about empowering your team to succeed while providing the right level of support.

We live in a culture that likes to glorify founders -- but the greatest companies are not built by one person alone. Company building is a team sport. If you want to win, you need to quit hogging the ball.

Around The Web:

More than half a million ‘TikTok refugees’ flock to China’s RedNote as ban looms via The Guardian 📱🪦

New users have piled in to the Chinese social media app RedNote just days before a proposed US ban on the popular social media app TikTok, as the lesser-known company rushes to capitalize on the sudden influx while walking a delicate line of moderating English-language content… The second-most popular free app on Apple’s App Store list on Tuesday, Lemon8, another social media app owned by ByteDance, experienced a similar surge last month, with downloads jumping by 190% in December to about 3.4m.

How Far Would You Go to Make a Friend? By Allison P. Davis via The Cut 📱🚶🏻📱

People who experience social isolation are 32 percent more likely to die earlier from any cause, a report from the same year found. A recent cover story in The Atlantic painstakingly charted how antisocial we’ve become; Americans of all ages are spending more time alone than ever before. Loneliness has become an epidemic, and we need to find ways to strengthen connections and relationships or we will, well, die. But as it always goes, an old problem creates new opportunities, and in the 20 months since the surgeon general’s report, an influx of founders and entrepreneurs have joined Belong Center in jumping into the growing market for human-to-human connection.

Justice Alito Asks If You Can Read Pornhub for the Articles by Olivia Craighead via NYMag 👀 👀 👀

The law, HB 1181, requires all websites with “over one-third sexual material harmful to minors” to use “reasonable age verification methods” to determine that users are over 18. Texas says the law protects children, while the adult-entertainment industry says that it’s a First Amendment violation. And Justice Samuel Alito? He’s just wondering if you can read a thoughtful essay about the state of American culture on Pornhub. “Is it like the old Playboy magazines?” Alito asked Derek Shaffer, the attorney representing the adult industry. “You have essays there by the modern-day equivalent of Gore Vidal and William F. Buckley Jr.?” Now, there’s an idea!

How a Would-Be Bomber Rebuilt His Life by Michelle Shepard via The Walrus ⛓⛓

The name attached to the November 8, 2023, message—Zakaria Amara—was one I had not thought about in years, but there was a time when I had spent hours studying him from afar. Amara was one of the leaders in the 2006 terrorism case where eighteen Muslim men and youth, four under the age of eighteen, were arrested for plotting to blow up downtown Toronto targets and a military base. Back then, I was the Toronto Star’s national security correspondent, and we covered the story extensively—weeks, months, years of ink… Throughout that first conversation, he seemed contrite, regretful, thoughtful, and pretty funny. But I still had a journalist’s skepticism. He was a convicted terrorist and had been described by police as persuasive and manipulative. I wanted to believe he was a changed man—but was he?