Tokyo Innovation Base: How to Ask for Help Without Feeling Awkward
A lot of founders are not afraid of hard work.
They’re afraid of asking for help.
Not because they are arrogant, but because asking can feel exposed. You worry you’ll sound unprepared, needy, or like you should have figured it out already. In a place like Tokyo, where people are often polite and indirect, it can be even harder to know how to ask in a way that lands.
I see this constantly through my community work at Tokyo Innovation Base. The founders who move fastest are not the ones who never need help. They are the ones who can ask cleanly, without drama, and without collapsing into self-doubt.
Why asking feels so uncomfortable
Asking for help triggers two fears at once. There’s the social fear of being judged, and the strategic fear of “wasting” a moment with someone you respect. That pressure makes people do one of two things. They either overexplain, or they stay vague. Both create the same outcome: the other person doesn’t know how to respond quickly, so they delay.
The reframe I want you to hold is simple. Asking is not a confession. Asking is leadership. It’s how you build relationships based on reality, not performance.
What makes a request “clean”
Most people want to help. What they don’t want is uncertainty.
A request becomes hard when the listener has to do emotional labor to interpret it, or when the “yes” requires a big commitment they can’t assess quickly. A clean ask creates a clear next step. It lowers the cognitive load. It also lowers your own anxiety, because you’re no longer trying to earn approval through effort.
Here’s the structure I use because it works in almost any context:
What I’m working on
What I need
Why I’m asking you
The simplest next step
That’s it. Not a pitch deck. Not a life story. Not an apology.
How this works in a TiB setting
The fastest progress usually comes from focused work, clear collaboration, and a shared rhythm you can repeat week after week.
At TiB, the most effective asks usually come after a real conversation, not as an opening move. If you start by listening, it becomes obvious what a helpful request would even be. You’ll hear where someone has relevant experience, where there’s overlap, or where they’re connected to someone you should meet.
When it’s time to ask, keep it small and specific. Think of it as building trust through one clean exchange. “Could I get your eyes on this one paragraph?” lands better than “Can I pick your brain?” “Is there one person you’d introduce me to?” lands better than “Do you know anyone who can help?”
Small asks build momentum. Big asks too early create distance.
The part nobody says out loud: timing matters
Sometimes the problem isn’t the wording. It’s your nervous system.
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Ask anyway, and make it specific. Most “basic” questions are only embarrassing when they’re vague. Clarity reads as professionalism, even when you’re still learning.
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Name why you’re asking them, keep the time ask small, and give them an easy out. Senior people are usually happy to help when the request is respectful and bounded.
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Start with what you’re trying to decide. You can say, “I’m choosing between two options and I’m unclear on the tradeoff.” That gives someone something real to respond to.
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Follow up once, cleanly, with a short message that references your last note. If there’s no response, assume the timing isn’t right and move on without taking it personally.
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Treat that as information, not a flaw. You may need tighter boundaries, more regulation before you send the message, or coaching on confidence and executive presence so your asks feel safer to make.
If you’re exhausted or spiraling, you’ll ask from urgency. Even if your message is polite, it can feel heavy. If you notice you’re rewriting the same ask repeatedly, it’s a sign you’re trying to manage fear on the page. Pause. Regulate first. Then ask.
A calm request gets faster responses, and it protects your confidence either way.
Work with Heather
If you found me through Tokyo Innovation Base and want support tailored to your goals, I offer coaching and facilitation designed for real schedules and real constraints. If you’re navigating high-pressure seasons, start with articles on Work-Life Balance and High Performance support. If you want to explore working together directly, you can view my services here.
