24 Other Ways to Ask "How Can I Help?" (and Actually Get a Helpful Answer)

The surprising reason this one question backfires, and what to ask instead

Jul 02, 2025

👋 Howdy! Claire here, Founder & CEO of Canopy. It’s been an active few weeks with 1:1 executive coaching clients and running trainings on “Coaching Through 1:1s” and “Creating Stability in a Team” — from it all, I wanted to write something on a question I often hear leaders ask with less-than-satisfying results 😅

If you find my writing helpful, please consider sharing with a friend or colleague who you think might enjoy as well (and so also subscribe yourself, if you haven’t already!)…

When you ask the question, “How can I help?” to your team, what’s the most common response you hear back?

Usually, it’s some variation of:

“I'm good.”

“Can’t think of anything.”

“Nothing, really.”

Perhaps there really is nothing that we as a leader can do to help.

But even if that were the case, you’ve likely felt the same frustration I have: You’re reaching out your hand to help someone out, but all your hand is grasping is air. You want to help as a leader but aren’t exactly sure how — even when you ask the question directly to your team.

Here’s the irony: The very question, “How can I help?” often doesn’t help much at all.

When we ask it, we unintentionally create more work for the other person. All of a sudden, they need to scan their to-do list, imagine your availability and context, then figure out what's appropriate to suggest. Many feel awkward about directing tasks to their manager or simply don't know what to ask for.

So, what to ask if we do want to be helpful? Instead of creating unintended mental load, we can proactively anticipate their needs by asking targeted questions.

Here are 24 other questions you can start with and ask instead:

Vision + Priorities

Am I giving you enough information to do your job well?
Would you like more or less direction from me right now?
Do you feel clear on where we're headed and why?
Are there any priorities I can clarify for you?

Work Style

What part of my communication style makes your job harder than it should?
Is there a decision I've made recently that you disagreed with—or didn't understand?
What's something I could stop doing that would make things easier for you?

Support + Load-Balancing

Do you feel like you're spread too thin right now?
Is there anything I could take off your plate this week?
Have I been mindful enough of timelines and bandwidth?
Would it help to reprioritize anything?

Coaching + Development

What aspect of your role would you like more coaching on?
Are there any skills you've been wanting to build but haven't had time?
Is there a challenge you're facing that we could unpack together?
What's a decision you're stuck on that we could talk through?

Work Conditions

Am I interrupting you too often with meetings or requests?
Do you feel like you have enough focus time to get real work done?
Is there any tool, resource, or system that's making your job harder than it needs to be?

Team + Dynamics

Are there any relationships or team dynamics that have felt tricky lately?
Is there a conversation we haven't had yet that we probably should?
What's something you wish people talked about more openly on the team?

Efficiency + Frustrations

What's one thing that's been frustrating you the past few weeks?
What are your biggest time-wasters right now?
What's something you wish we did more efficiently as a team?

The next time you feel the urge to ask, “How can I help?” pause and pick one of these questions instead. You may find the answers more helpful, more actionable, than you previously imagined.

-Claire

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🧭 Explore 1:1 executive coaching with me personally, as you navigate a new leadership role or new organizational dynamics. (I’ve had the privilege of coaching leaders at Apple, Uber, and fast-moving organizations, and have helped over 50,000 managers grow through Canopy’s trainings.)
📣 Invite me to deliver team keynotes and workshops, remotely or in person on this very topic of coaching + developing your team.
🚂 Partner with me to roll-out a leadership training program for your managers.
🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚