The Awkwardness of "Making the Ask"

If I haven’t bombarded you enough with emails, LinkedIn posts, or other social media, you might be the only person in my extended universe who doesn’t know that my second book is coming out in six days.

Previously on Substack I wrote that after writing my first book I vowed that I would never write a second one.

Until I wrote a second one.

As I shared then, my first experience at book writing wasn’t what I thought it would be.

Don’t get me wrong — the book was translated into multiple languages, sales were solid, and it served as a summary of my course, The Industrialist’s Dilemma. The book succinctly captured eight years of work in a single tome. I was proud of the output.

The book also helped make the course’s learnings known to a larger audience, which allowed me to travel globally and work with numerous companies on issues of digitization and transformation.

But the book launch and selling process? When I started, I had no idea what it would be like…

Say What?

In my naive mind, I entered the book writing process thinking that an author writes a book that tells a compelling story or provides insights, and that hopefully the world welcomes it for the content. Word-of-mouth and great reviews could lead to book sales, I thought.

I had first-hand experience that led me to believe this narrative. When I was 27 years old, I did the research for Andy Grove’s best-selling business book, Only the Paranoid Survive. Andy wrote the book, the business community loved it, many copies were purchased, and for several years it was celebrated as a legendary business book.

Simple.

However, even before I started writing my first book, my agent asked if I was going to create a promotional website, hire a digital marketing team, and retain a PR firm. I had no idea what that meant or what was involved. And I was shocked when I was told how much these services would cost and what I was expected to do. I was repeatedly asked by potential publishers about my “platform”— my social media presence, how many followers I had on X and LinkedIn, and if I could get my employer to buy many books and promote the title.

It all seemed so strange — the publishers I spoke with, and the one I ultimately chose, did not really do any marketing or outreach for the book. I was expected to sell the book myself.

At one point I was surprised when several people involved in the launch asked how many copies I intended to buy the first week to get on best seller lists. I was even coached on how to do this in ways that would maximize the chance of success for receiving book accolades.

My reaction at that time was two-fold:

1. I thought I needed to take a shower. It felt like the old payola scandals for getting songs played on the radio.

2. I was amazed that in addition to how much it was going to cost me to hire my marketing team, I was being encouraged to spend tens of thousands of dollars to buy my own books.

I ultimately understood that this is often how it is done today. With so much noise in the business world and with so many “experts” online, many authors — especially first-time writers — are expected to create their own awareness and momentum.

As I launch my second book things are very different. I have a much stronger publisher that has been extremely helpful and more supportive than I experienced during my first endeavor. My whole team has been collaborative and engaged in ways that have made this experience vastly different than my first launch.

Yeah, But…

In the end, however, I’m still expected to sell books. After all, this is in my interest, and books don’t sell themselves.

For The Systems Leader I’m doing everything on the marketing front that I’ve been encouraged to do. I’m not only doing a full-court press for PR and sharing information about the book on social media, but I’m making videos, asking all my friends and contacts to buy books, etc.

And while I understand that this is how it is done, I have to say – it’s kind of awkward.

When I watch other prominent writers promote their books, I don’t think they are doing anything bad. For writers that share original thoughts and ideas that push me to think about difficult issues or that teach me new knowledge, I enjoy getting exposure to what they do.

But I also know we live in a world of influencers, and my LinkedIn feed seems to have a lot of “shallow advice” — people saying and writing pithy things that lack depth.

I guess that’s what LinkedIn’s algorithms want me to see.

And I worry that this is how I will come across — pithy and lacking depth. And I know it will come across that way to some people.

Is my feeling awkward about this due to my personal insecurities? My lack of confidence?

That’s surely part of it.

And let’s be clear: I LOVE talking about the material. I could go on for days about the great leaders I’ve studied, what I’ve learned from each of them, the trends I see around the world, the difficulty in balancing cross-pressures, pointing out unserious behavior in a serious world – all of it.

In front of a classroom or company I have no hesitancy going on and on about systems, free will, purpose, innovation, balancing strength and empathy.

That’s my happy place.

But asking people to buy my books?

I don’t know that I’ll ever get used to it.

---

The Systems Leader: Mastering the Cross-Pressures that Make or Break Today’s Companies, can be bought at your favorite online or physical bookstore. Here are a few places you can find it:

Amazon

Barnes and Noble

Apple