The 45th: Asking: The Art, The Pain, The How

Published: October 25, 2020

The 45th Briefing Notes | MONEY TALK


There is a list of things I wish I learned earlier in life — like say, while I was in grade school or high school.

One of the items on said list is how to get comfortable with asking. For what I want. For what I need.

I don’t remember ever taking a class on this. Or even a sit-down with my guidance counselor about it. I think I was just expected to know how to do it. Life would have gone a lot easier if I had learned this very important task earlier.

Financial Behaviorist (and Briefing Notes reader) Jacquette Timmons had this to say about asking:

Let’s face it: You and I ask for things all day long. But asking for what you really want is hard! Yet, doing so is at the heart of every single negotiation, regardless of what’s being negotiated or with whom.

Timmons points out one reason asking is hard is that it makes us feel vulnerable. So, we avoid having to do it.

And when we HAVE to do it, we don’t go for the direct approach. We hint or drop innuendos. Which — if we look at it from the receiver’s point of view — is so frustrating. I’d much rather hear what it is I’m being asked to do.

In her book The Art of Asking, artist Amanda Palmer wrote:

It isn’t so much the act of asking that paralyzes us. It’s what lies beneath: the fear of being vulnerable, the fear of rejection, the fear of looking needy or weak. The fear of being seen as a burdensome member of the community instead of a productive one. It points, fundamentally, to our separation from one another.

Beyond making us feel vulnerable, asking also demands self-honesty and self-awareness, says Timmons.

For us to be able to make a direct, unambiguous ask, we have to know what it is we really want.  The more specific our ask, the easier it is for the other person to respond either way.

But we can only make specific asks when we’re clear about what it is we’re trying to achieve and how ‘the ask’ will help us get there.

And then too, sometimes, our own backstory gets in the way. What we’ve experienced — either as the person asking or the person being asked — can color our thinking. How we were brought up may also be influencing how we feel about asking.  (My own story on this in the Last Word section.)

“Asking for help with shame says: You have the power over me. Asking with condescension says: I have the power over you. But asking for help with gratitude says: We have the power to help each other. ”
— Amanda Palmer

Okay. For all these reasons, asking is hard. How do we get better at it?

Scroll down to the Interestingly section for suggestions on specific situations. Jacquette Timmons’ post offers a set of guidelines that we can apply to most scenarios. For inspiration (and laughs), I recommend Amanda Palmer’s book.

And — for the love of all things holy — practice. (#notetoself)


If there’s one type of work that REQUIRES a healthy attitude and mindset around asking, it’s sales. Want to brush up on your sales and marketing chops?

Check out these best-selling sales and marketing classes at CreativeLive. I’ve taken the ones taught by Vanessa Van Edwards, Ryan Holiday, Amy Schmittauer. Plus a whole bunch on the list taught by Tara Gentile.

P.S. This is an affiliate link.

  • How to ask for a promotion. This one can be nerve-wracking. “You’re not in control; you’re putting yourself in the hands of your manager to be judged — and you might be judged not worthy.” But we all have to learn how to be an advocate for ourselves. HBR gives pointers on how to make the request.
  • How to ask for referrals. “If I deliver great work for my clients, the referrals will come.” The truth? This approach is passive, especially in these uncertain economic times. Taking charge of our business means actually asking for referrals. FreshBooks shares when to ask and how to ask. They even include email templates.
  • How to request a testimonial from a client. Word-of-mouth recommendations and reviews from customers and clients are often key to winning a sale from someone new. Hubspot details 8 steps on how to ask for the testimonial and how to make it easier for our customers to say yes to our request.
  • How to ask for a recommendation on LinkedIn: We all know the importance of maintaining a robust LinkedIn profile. One element of that great profile is the recommendations from colleagues, clients, previous bosses, etc. The Muse talks about when, how, and from whom we should ask for a LinkedIn recommendation.
  • How to ask for a letter of recommendation. Many employers today favor references over letters of recommendation. However, there are still times when it may be requested. “Letters of recommendation allow employers to hear from others what they valued about working or interacting with you.” Here’s Indeed’s take on when and how to ask for one. Take note of their advice not to ask a friend for recommendation letters, if at all possible.


“There’s really no honor in proving that you can carry the entire load on your own shoulders. And…it’s lonely.”
— Amanda Palmer


The Art of Asking
by Amanda Palmer

Part manifesto, part revelation, this is the story of an artist struggling with the new rules of exchange in the twenty-first century, both on and off the Internet. The Art of Asking will inspire readers to rethink their own ideas about asking, giving, art, and love.

This and other book recommendations here.


Had you been listening to Top 40s back in October 1995, you would have been hearing a lot of Hootie & the Blowfish. Back then, their single “I Only Want To Be With You” was #6 on the charts. [Side Note: #1 on the charts was Mariah Carey’s Fantasy, but I really didn’t want to talk about her.]

Whatever happened to Hootie? Esquire had this to say: “Here’s the thing: We never really stopped liking Hootie & the Blowfish, we just began to concern ourselves with whether our peers did. We thought that our neighbors thought that Hootie was no longer cool and, afraid of appearing uncool ourselves, we threw them overboard. We began constructing and altering our tastes and personalities for public consumption. No wonder reality television and Instagram were right around the corner.”

Enjoy this (YouTube) look back to Hootie and the time pre-American Idol and Simon Cowell.


Waaaayyy back in August 2018, I asked Kristen Runvik about her strategy for finding the roles that make up her portfolio career. You know what she said? She asked around.

“People always ask me how I find these cool jobs. ‘How is this always happening to you?’ It doesn’t happen to me. I’m literally out there asking.

This is my favorite tactic. I make a list of exactly what I want and what I’m good at. Then I send out an email. I don’t blast-email a bunch of people, but I send individual emails to people I know. Some will say they’ll keep me in mind. Others will never respond. And some will just say, ‘Hey, great to hear from you.’

The last time I did this, a friend introduced me to someone he knew and a week later, I was hired. I’ve used this strategy for many different positions in the past.”

You can listen to this pulled-from-the-archive interview here.


Briefing Notes is researched, written, and edited by me alone. Each issue takes hours to produce and requires investments in numerous sources to sustain. I would be so grateful if you’d consider buying me a coffee or two. Your support really matters and it tells me you find value in this newsletter. 🧡

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“Ask” is going to be one of my words for next year. (Yep, my head’s already in 2021. Isn’t yours? 🤣)

So, I’m getting ready. It’s a big challenge for me, TBH. I was brought up in an environment where self-reliance was a prime virtue — which, granted, I took to extremes.

It’s taken All.My.Life to ease up on that and swing the pendulum back a bit. So, “ask” it is for 2021.

Have you started thinking about where you want to focus on 2021 yet? Hit ‘reply’ and let me know what you’re thinking.

Here’s to a productive week, safe, and sane week.

Cool beans,
Lou Blaser


A former management consultant and IT leader, Lou Blaser is the editor of Briefing Notes and the host of the Second Breaks podcast. She is also the author of Break Free: The Courage to Reinvent Yourself and Your career. Lou’s work is focused on helping experienced professionals navigate an evolving work landscape so they can continue their impact and relevance in a changing world.

The world of work is changing.

Stay smart about it.

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