Have you ever hesitated to hand off an important responsibility because you weren’t entirely sure it would get done right?
Many leaders struggle with delegation — not because they don’t understand its importance, but because letting go can feel risky. Your reputation, results, and team performance are on the line, so it’s natural to want to keep a tight grip.
The problem is, holding on too tightly slows down team growth, bottlenecks progress, and keeps you overworked. True leadership requires building the capacity of others — and that means developing trust and confidence in their ability to deliver.
Here’s a three-step process to help you delegate with less fear and more success.
Step 1: Create a Development Plan Before You Delegate
Delegation works best when your team members are equipped for success. Before handing over a responsibility, set aside dedicated time to meet with the employee (or employees) and identify areas where they may have knowledge or skill gaps.
Once those gaps are clear, work together to create an action plan for addressing them. For example: if someone needs to produce a department P&L report but struggles with financial literacy, they could schedule time with the CFO to walk through reporting processes and key P&L components. By investing in their skills up front, you’ll feel more confident in their ability to handle what you’re handing over.
Step 2: Build Trust Through Consistent Check-Ins
Delegation is not “set it and forget it.” It’s “trust and verify.” Maintain regular one-on-one meetings so you can track progress, catch issues early, and provide support where they’re stuck.
These meetings aren’t about micromanaging — they’re about creating a rhythm of communication that keeps both of you confident the work is moving forward. Over time, these check-ins will also strengthen your working relationship and make delegation feel less like a leap of faith.
Step 3: Shift Your Approach Over Time
When training someone on a new function, it’s appropriate — and often necessary — to be more instructive and directive in the early stages. For the first 60 days, give clear instructions, set expectations, and model the process.
After that initial period, shift into a more collaborative, coaching-oriented style. Instead of providing answers right away, ask questions that help your team member think critically, explore solutions, and problem-solve on their own. This gradual shift not only builds their confidence and independence, but also frees you to focus on higher-level priorities.
Mini FAQ: Delegation Without the Fear
Q: How can I delegate important tasks without feeling like I’m risking everything?
Preparation and communication are key. Equip your employee with the skills they need, maintain regular check-ins, and gradually give them more autonomy over time.
Q: What if my employee isn’t ready for the responsibility I need to delegate?
Identify their gaps early and create a development plan to address them. For example, pair them with a mentor, schedule targeted training, or provide resources that build their competence before the handoff.
Q: How do I make sure delegation doesn’t turn into micromanagement?
Set a cadence of one-on-one meetings for progress updates and problem-solving. The goal is to support and verify, not control every detail.
Q: When should I stop giving step-by-step instructions?
After the first 60 days of learning a new function, start shifting toward a coaching approach. Ask open-ended questions that prompt critical thinking before offering your perspective.
Q: Why is delegation so hard for leaders?
Often, it’s tied to fear — fear of mistakes, missed deadlines, or disappointing results. Overcoming that fear requires building trust through skill development, consistent communication, and a gradual handoff of responsibility.
“Delegation isn’t a sign you’re losing control—it’s a sign you’re leading at your highest level. Let’s talk about how you can make it feel less risky and more rewarding.” – Angela Sasseville
Schedule your 20-minute complimentary conversation with Angela to explore how leadership coaching can help you delegate with confidence and grow your team’s capacity.