Asking for help is hard

Asking for help is hard

“Can you come down?”

It was a text I didn’t expect to send but found myself hitting send anyway.

My son had had three seizures in a 24-hour period and we’d been to two different hospitals in the same amount of time.

It took convincing from my sister, but I asked my mom to divert her business trip to Boston to be with us in LA. I then hit send on the text above to ask my sister to come down, too.

The truth is: rarely do I find myself in a situation where I’m asking someone for help, even with my family.

???Reader: this is a red flag.

Asking for help or knowing how to identify when you need it is a key strength of some of the best leaders.

It shows vulnerability, trust, and gives others the opportunity to step up.

Here’s a quick audit every people leader should be doing:

  • Do I ask for help before I’m overwhelmed?
  • Do I accurately scope out work?
  • Do I say yes to too many things and slip on deadlines because of it?
  • Do I know how to delegate?

Asking for help is hard. Even when you really need it.

Why is it so hard to ask for help? There is a science to this.

Human beings are deeply social. We’re wired to connect with each other. But we have something that stands in the way: the stories we tell ourselves.

Here are the top three barriers:

?? People underestimate others’ willingness to help

?? People underestimate how good it makes someone feel to be asked for help

?? People overestimate how inconvenienced someone will feel to be asked


A leader who doesn’t ask for help may look like this:

?? A perfectionist who knows how to do the work, but not how to delegate the work

?? A people-pleaser who says yes to every task that comes across their desk

?? An achiever who wants the big projects (and the recognition that comes with them), even if they happen all at once

?? A striver who is either unaware or unable to identify their own abilities/limits

All are dangerous. All lead to high levels of burnout – for the individual and the team.

Here are two ways this shows up in me:

  1. Saying I can help with a task to show up as a team player and then not being able to get to it because it was never realistically in scope for my week
  2. Saying yes to projects and then getting derailed by higher priorities (and never circling back)

The biggest barrier to asking for help in each scenario has to do with underestimating others’ abilities: will they want to do the work/figure out how to do the work themselves?

??? Hot take: When we refuse to ask for help, we’re robbing someone else of their potential.

When asking for help goes wrong

I feel the need to include a disclaimer. I am not advocating for unabashed help-taking. We all know someone who constantly asks for help and never acknowledges the effort. Or a boss who is so good at delegating you find yourself asking, “Am I doing their job?”

This post is not about those people!

This is about people who struggle to ask for help and want to change that (?? me). For themselves and for their teams.

My TLDR advice:

Don’t wait for the big moments.

Building a foundation of trust

So how did I find myself asking for help last weekend?

I really, really needed it.

???Reader: you should never let yourself get to this point before asking for help.


Another ingredient: I have a solid foundation of trust with the people I was asking.

Trust is “choosing to risk making something you value vulnerable to another person’s actions.” - Charles Feltman

This could be as simple as your success (something you value that has tangible outcomes, ie, a bonus), which as a leader is predicated on your ability to lead people to achieve certain results.

Or as complex as your mental health.

According to Feltman, there are four variables that impact trustworthiness:

  1. Sincerity - do I mean what I say
  2. Reliability - do I do what I say I’m going to do
  3. Competence - am I aware of the abilities I do or do not have
  4. Care - do I have other people’s interests in mind

Here’s a screenshot of the definitions for good measure:


In order to build trust, you need to actively work on these four pillars. I hate to report there are no shortcuts here. Just doing the work to get the outcome you want!

?? Be sincere. Am I intentional with my words and actions? Do I clearly communicate priorities and check in regularly when they change? Do I acknowledge when I make mistakes or miss a commitment? Do I apologize?

?? Explain and invite input. Did I do my due diligence in creating my goals? Am I well-researched and credible vs. working off a gut instinct? Can I communicate my perspective and sources clearly? Do I invite team perspectives when making decisions?

?? Practice care. Am I fully present in conversations and interactions with others instead of multi-tasking? Do I ask my team about their needs and lives? Am I thoughtful in how I express myself or react? Have I established ground rules for how to show care and respect as a collective?


Note: Jay is okay! I won’t get into his diagnosis because it’s his life and he doesn’t need it on the internet.

Second note: Moms are less okay! We feel better that we have more information, but I wouldn’t call myself relaxed or at ease. The worry never really leaves.

Colton Sakamoto

Operator | Co-Founded Inflection Points (Thiel, XYZ) | Writing at joinofficeparty.com

1 年

Lots of people WANT to help too! Hard to find those people if you don’t ask

Eduardo Nu?ez

Fractional CMO, Startup Advisor, and Entrepreneur

1 年

Knowing when to ask for help is IQ. Actually asking for help takes EQ, it requires courage.

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