Delegating in a Fast-Paced Work Environment

Built 3 companies to $200M. Here's what I learned about delegation: Most CEOs think they're bad at delegating. The real problem? They're delegating wrong. The hard truth: You're not protecting your team by doing everything.     You're: Burning yourself out Bottlenecking growth Breaking trust     Your team needs to feel valued, not protected. Here's my proven system:     1. The Mindset Shift I used to think:  "No one can do this as well as me." Reality check:  When I got a concussion and couldn't work, my team excelled.     They just needed space to step up.     2. The Success Formula Before delegating any task, define: • What does success look like? • What's the deadline? • What resources are needed? • How will we measure results?     Clarity creates confidence.     3. The Communication Machine Create clear channels: • Slack = company chatter • Notion = project discussions • Email = external only • Weekly memos = alignment     No one-off conversations about projects. No decisions in DMs.     4. The Trust Test Ask yourself: "Would I pay someone $1M/year to do what I'm doing right now?" If not, why are YOU doing it? Your job is to: • Set vision • Build systems • Lead strategy • Make key decisions Delegate everything else.     5. The Weekly Ritual Every Friday, ask: • What did I do this week that someone else could do? • What meetings could I skip? • Where am I the bottleneck? • What systems need building?     Then take action.     6. The Team Power-Up Your team needs to know: • Where we're going • Why it matters • How they contribute • What success looks like     Give them this clarity, and they'll surprise you. The Final Truth: A CEO doing $10/hour tasks is a $10/hour CEO. Your company needs you operating at your highest level. Delegation isn't about doing less. It's about focusing on what matters most.   ♻️ Repost to help a leader in your network  🔔 Follow Christine Carrillo for more

“I know I need to delegate more, but some things are too complex to hand off.” Sound familiar? This mindset keeps many founders stuck in the weeds instead of leading strategically. Let me share a practical framework I use with clients: The Delegation Staircase. It transforms overwhelming handoffs into manageable steps: Step 1: Let them shadow you • You do the task while they observe • Debrief afterward to share your thinking process • Build understanding through observation Step 2: They observe and explain • They watch you again • This time, they explain your rationale • They articulate why you made specific decisions, and you provide feedback Step 3: They do, you debrief • They perform the task • You review together • You provide feedback on what you might have done differently Step 4: They take ownership • They handle the task independently • Optional: You give final approval before delivery • Gradually remove the approval step based on competence The key? You don't have to jump straight to full delegation. Each step builds confidence - both yours and theirs. This approach has helped dozens of founders successfully delegate complex tasks, from board presentations to client strategies. What else has helped you delegate complex tasks? Or what other delegation challenges do you have? #StartupLeadership #Delegation #LeadershipDevelopment #ExecutiveCoaching

"I'll delegate when I find good people." Translation: "I'll trust them after they prove themselves." Plot twist: They can't prove themselves until you trust them. Break the loop. Delegate to develop. Here's how: 1️⃣ What should you delegate? Everything. Not a joke. You need to design yourself completely out of your old job. Set your sights lower and you'll delegate WAY less than you should. But don't freak out: Responsibly delegating this way will take months. 2️⃣ Set Expectations w/ Your Boss The biggest wild card when delegating: Your boss.  Perfection isn't the target. Command is.  - Must-dos: handled  - Who you're stretching   - Mistakes you anticipate   - How you'll address Remember: You're actually managing your boss. 3️⃣ Set Expectations w/ Yourself  Your team will not do it your way.  So you have a choice: - Waste a ton of time trying to make them you?   - Empower them to creatively do it better?  Remember: 5 people at 80% = 400%. 4️⃣ Triage Your Reality - If you have to hang onto something -> do it.  - If you feel guilty delegating a miserable task -> delete it.  - If you can't delegate them anything -> you have a bigger problem. 5️⃣ Delegate for Your Development  You must create space to grow. Start here:   1) Anything partially delegated -> Completion achieves clarity.  2) Where you add the least value -> Your grind is their growth.  3) The routine -> Ripe for a runbook or automation. 6️⃣ Delegate for Their Development Start with the stretch each employee needs to excel. Easiest place to start: ask them how they want to grow. People usually know. And they'll feel agency over their own mastery. Bonus: Challenge them to find & take that work. Virtuous cycle. 7️⃣ Set Expectations w/ Your Team  Good delegation is more than assigning tasks:  - It's goal-oriented  - It's written down  - It's intentional When you assign "Whys" instead of "Whats", You get Results instead of "Buts". 8️⃣ Climb The Ladder Aim for the step that makes you uncomfortable:     - Steps over Tasks  - Processes over Steps  - Responsibilities over Processes  - Goals over Responsibilities   - Jobs over Goals  Each rung is higher leverage. 9️⃣ Don't Undo Good Work Delegating & walking away - You need to trust. But you also need to verify. - Metrics & surveys are a good starting point. Micromanaging - That's your insecurity, not their effort. - Your new job is to enable, motivate & assess, not step in. ✅ Remember: You're not just delegating tasks. - You're delegating goals. - You're delegating growth. - You're delegating greatness. The best time to start was months ago.  The next best time is today. 🔔 Follow Dave Kline for more posts like this. ♻️ And repost to help those leaders who need to delegate more.

Your calendar isn’t the problem. You are. Years ago, over dinner with Ben Chestnut, co-founder and former CEO of Intuit Mailchimp, I asked: "I feel like I could be doing more. How do you manage your time and stay so productive?" I expected a magic hack. A silver bullet. Instead, he said: "You don’t have a productivity problem. You have a people problem. Are you delegating? Do you have the right people to delegate to?" Boom. Game over. My entire view of leadership shifted in that moment. Until then, I thought my job at Wistia was to do more: keep my inbox at zero, squeeze every minute, put out every fire myself. But Ben was right. My problem wasn’t time. It was that I wasn’t giving enough ownership away. So I started fully delegating to my senior team. Here’s what happened: → Some thrived and scaled faster than I imagined. → Others struggled and failed quickly. → I learned more about my team in months than I had in years. I had more energy for the things only I could do to move the business forward. Others grew faster, took on more, and their expertise began to shape the company in ways I couldn’t have alone. That’s when it hit me: delegation isn’t just a way to keep your head above water. It’s the difference between running a business and scaling one. After more than a decade of practicing it, here’s how I think about delegation today: 1. The 80% Rule: If someone can do it 80% as well as you, delegate it. 2. Hold Strategy Close: Set clear goals so everyone’s aligned, then give them ownership: highly aligned, loosely coupled. 3. Expect Failures: Some projects and people will fail. Keep failures small, make them lessons, and weigh effort, risk, and learning before stepping in. 4. Feedback is Fuel: Delegation without feedback is bad. Give plenty, especially early. 5. Over-Communicate: As your business grows, repeat the strategy, values, and mission. Keep the big things steady, let the small things evolve. Thank you, Ben, for sparking the insight that changed how I lead. Give the right people absolute ownership and they won’t just free up your time. They’ll take your business where you could never go alone. Where are you holding on too tight, and what might happen if you let go?