The Leadership Lesson I Never Expected… 

I never thought one of my most leadership lessons would come from one simple question: “Do you need help?” I remember sitting in silence when my manager asked me that. I didn’t know how to answer. Asking for help had never crossed my mind. 

I just started working at a new company. I was leading a massive project with an aggressive audit deadline. I was building a program from scratch, executing it, and wrapping it up perfectly for compliance. But as the weeks went by, pieces started falling apart. Stakeholders wanted answers I didn’t have. My inbox was overflowing, complaints were piling up, and I was working around the clock just to keep things afloat. Deep down, I thought, I cannot fail at something this big and of this importance… 

The Rescue 

You would think when my manager asked if I needed help, I would feel joy, happiness, and relief. However, the feelings I had were very different. Low confidence kicked in, rooted in the younger version of me. I thought asking for help meant lack of competence. I immediately felt ashamed, inadequate, and embarrassed. I kept thinking; I should know how to handle this on my own. Regardless of my thoughts and ego, I replied with “Yes.” I knew I was in over my head and accepting help was the only way forward.  

Within a day, my manager helped me build a framework, hire short-term support, and rally a team. Instructions went up on the whiteboard, names were assigned, and deadlines were set. The plan was clear, energy was high, then she left. It was on me to lead the rest. 

Questions flew at me from every direction. Some I could answer, and others I could not. That first night I ordered pizza. The team stayed as long as they could, leaving little by little until the room was quiet at 7pm. That’s when my solo work began. I followed up on everything from that day. I answered emails, drafted communications for thousands of employees, and checked off tasks one by one. I worked until midnight.  

The next day brought new challenges. Some team members didn’t show up and I had to hire more help. A few weren’t performing and had to be replaced with people who had the right skillset. Every person mattered. One team member had just had a baby. She pumped every few hours, laptop in hand, still contributing. I’ll never forget how much I appreciated her dedication. I needed every ounce of help. On the other hand, not everyone shared that level of commitment. Another team member looked at me and said, “You will never be able to do this. You are going to fail.” That comment had me questioning my ability. After sharing this with my manager, she informed me I was sucking up the negative energy of those around me and that team member was not right for the position. 

 Weeks blurred together. I worked late every night, living off cold pizza. I laughed, I cried, and I wondered if it would ever end. I even canceled my birthday vacation. When the deadline finally came, we delivered. However, the cost and the lesson stayed with me. 

My Leadership Lesson 

Although this story ended successfully, the road to get there was anything but easy. My lack of planning and hesitation to ask for help early on left me overwhelmed and behind, draining both me and my team. Pride kept me from admitting I was in over my head. I often wonder where we would have ended up if my manager hadn’t asked that simple question: “Do you need help?” That moment saved the project. It also taught me one of the most important leadership lessons of all: asking for help is not a weakness, it’s a strength.  

Success isn’t about doing everything alone; it’s about leaning on the strengths of the team around you. In a work setting, that team exists for a reason, to combine ideas, expertise, and support to create the best possible product or service. When we learn from and collaborate with those around us, we grow and often achieve outcomes far better than we could on our own! 

Call to Action 

Here are 3 steps to help you ask for help before it’s too late: 

• Pause and assess: Are you overwhelmed or behind? Write down what’s slipping.
• Identify your support network: Who can help you move forward? Make a list. 
• Ask early: Don’t wait until you’re drowning, reach out today. 

When we learn and accept help from others, that makes us courageous. Leaders are courageous. Have the courage to ask for help. 

With love, leadership, and belief in yourself. You got this! 

💖 Jessica