Productivity Coach’s Corner: Ask Early. Ask Often.

What caregiving teaches about leadership and time.

I have spent my career helping leaders think more clearly, work more intentionally, and use their time well. Five months into my mom’s stroke recovery, I find myself practicing a leadership lesson I have taught for years but never expected to confront personally.

What I did not anticipate was how closely the work of caregiving would mirror the work of leadership. Both require attention, humility, and the ability to ask for help long before the moment becomes overwhelming.

Over these months, I have learned something simple but difficult: People cannot help you until they know what you need.

And you cannot tell them what you need until you’ve clarified it for yourself.

Every day brings a new challenge. Medical terminology that feels like a coded language. Communication gaps that require creativity and patience. Nights when I stay with my mom… so my sister can sleep at a friend’s house and get a complete night of rest.

Moments when I want to be strong for everyone yet realize that real strength comes from being honest about what I cannot carry alone.

What surprised me most was how consistently people step in when I articulate a short-term or mid-term objective. When someone asks, “How can I help?” and I’m prepared with a clear answer, support becomes actionable. When I’m vague, their intention remains warm, but nothing moves.

Clarity Becomes the Catalyst

Leaders often underestimate this. In organizational life, we tend to equate competence with independence. But research on psychological safety, including the work of Amy Edmondson, shows that teams perform better when leaders model curiosity and vulnerability.

When a leader raises their hand early—whether to ask a question or request assistance—they send a message: Clarity matters more than appearances. Progress matters more than pride.

A workplace example illustrates this well. A new hire joins a team, ready to contribute, but soon hits a common barrier: acronyms and shorthand. Every organization has its own internal vocabulary, and newcomers rarely have access to it. The mature leader is the one who raises their hand in a room full of senior colleagues and says, “I don’t know what that means.”

That moment breaks the spell. It normalizes transparency. And it raises the standard for the entire culture.

In caregiving, the same dynamic appears. Doctors and therapists speak quickly, assuming mutual understanding. Each time I pause to say, “Can you explain that another way?” the quality of our decisions improves. Asking early prevents costly mistakes later, just as it does in any workplace setting.

Time Management Becomes an Operating System

But asking for help only works if you have a structure to hold it.

This is where time management becomes more than a set of tips—it becomes an operating system. Throughout my career, I’ve used a range of organizational methods. The specific system matters less than the reliability of using one. Leaders with a trusted place to capture commitments, questions, and offers of support are positioned to use their time with far more precision.

Caregiving has forced me to rely on my systems more rigorously than ever. I track what we need this week, what we may need next month, what each specialist recommends, and who has offered help.

Without this structure, support would drift away. With it, people feel engaged and able to contribute meaningfully.

This is where productivity and leadership meet: Asking for help is not a sign of weakness. It is a strategic behavior. It reduces rework, eliminates ambiguity, and shortens time to clarity. Leaders who ask early save hours—sometimes days—of misalignment and second-guessing.

So here is my invitation to you:

In the next week, identify one concrete, immediate, and easy to articulate short-term goal. Share it with someone you trust. When they ask, “How can I help?” give them a clear, specific answer.

Then choose a mid-term goal for the next few weeks.

Share that, too. And when someone offers help, accept it.

This is more than trying to “manage time.” This is a practice; a way of strengthening connections and cultivating readiness. If my mom’s recovery has taught me anything, it is this: We move further, faster, and with more steadiness when we raise our hands early, when we stay connected, and when we allow others to meet us where we are.

As leaders and as humans, that is where real productivity begins.

Dr. Jason Womack
Dr. Jason W. Womack (www.WomackCompany.com) is an author, TEDx speaker, and leadership coach working with organizations as they re-imagine not just how people work together, but the way colleagues both take care of AND challenge each other. His programs help people stress less, focus more, and achieve greater levels of success…as defined by each individual who contributes to the organizational mission. His books can be found at Amazon: https://www.amazon.com/Jason-W.-Womack/e/B005N3257A