Best books for new, first-time managers

I recently asked on Twitter: “what book would you recommend most for new, first-time managers?” It’s been a while since I’ve been a first-time manager or managed first-time managers directly, so I was curious. Below is the list of what folks recommended. The categories were added by me after realizing an unstructured list of 35+ books would be too overwhelming. I certainly haven’t read all of these books but put some notes in the list next to books I have read and a few notes next to ones I haven’t read but know something about. If you have a book you think should be here and isn’t, email me ( I’ll also include this in the newsletter I’m launching (more info here).

General management & leadership

Tech management and leadership

Note: having been a CTO and CEO, I recommend reading these books alongside the more general management books. An engineering leader with strong general management chops and business skills is a rare and valuable breed. 



 Prioritization and results

Psychology and how people think

Other (literature, non-fiction with important themes)

Michael Dearing suggested taking his very well-regarded general management course, so I mention that here. Even if you can’t take the course, check out page two of the syllabus for some great readings. Thanks, Michael!

Again, if you have a book you think should be here and isn’t, email me!( I’ll try to keep it updated.

Why I’m launching a newsletter

I announced on Twitter that I’m launching a newsletter. It’s called Chad Dickerson’s Fieldnotes (more about the inspiration for the name). I expect it to be roughly monthly starting later this month. Subscribe here. Some people have asked me why so I thought I’d explain.

In general, I plan to be writing a lot more and the newsletter is part of it. My vision for my newsletter is a focal point for all of my writing (on this blog and elsewhere) while aggregating and commenting on some of the interesting things I find along the way. Topics will include business, music, books, culture, what I’m up to, and what I learned as a CEO and CTO. I have a lot to say and I’m excited to be able to say it as a free agent with a high degree of editorial independence.

My time at Etsy was also very profound and there are lots of insights from that experience that I haven’t had a chance to lay out yet. Writing is a great way to process and refine one’s thinking. Very few people have the chance to take on two major executive roles (CTO and CEO) in a company like Etsy from building a team and rebuilding a platform as a startup CTO (the proverbial changing of the jet engine while in flight) to leading a high-profile public company as CEO and Chair of the board. I did that and I’m confident that I took that path in a way that was true to my self and to a set of larger principles. I know other people are trying to do the same thing and I hope some of my writing will give them insight and strength.

Many people reach out to me and want to talk about Etsy as a socially responsible company. I will certainly write about that, probably a lot and in a very pragmatic way. Socially responsible business remains a passion of mine. That business orientation was super important to me in my time at Etsy but I also think the focus on that aspect of Etsy can obscure the sheer improbability of *any* venture-backed company making it through all the stages we made it through at Etsy. In my time there, Etsy wasn’t just special in a cultural sense, it was very special in a pure business sense. If you look at this CB Insights analysis of the cohort of companies who raised seed rounds in 2008-10, only 5 out of 1098 had a $1B+ exit. 3 of those went public and 2 were acquired. These kinds of odds are astounding for any company, much less a spirited and unconventional company like Etsy. We were doing a lot of things that simply hadn’t been done before or even attempted. (Oh, and we also faced down Amazon in the process. No big deal. When the New Yorker visited one day, the headline of their story was “Visiting Etsy, Amazon’s Next Prey” and SNL Weekend Update had a great bit on the competition around the same time — see 2:45 mark in this video)

I wrote a lot while at Etsy and always always loved doing it. A few still take me back to the moment I wrote them as if it was yesterday. Only two weeks into my arrival, I wrote about the massive challenges I immediately encountered as CTO in September 2008. I wrote the first post and the About page on the Etsy engineering blog, Code as Craft. I wrote about my long-term vision for Etsy in May 2012 as CEO when we became a B Corp, dropping a reference to fellow Brooklynite and (I think) Etsy kindred spirit Walt Whitman. When we went public, I wrote a post referencing James Joyce and quoted Ovid. I was never doing this to be a pretentious show-off. My view of the world is just very integrated. Liberal arts, tech, art, business, technology, literature, music — they are all connected and the more we make connections across all of those disciplines, the better we will be for it (side note: who among us isn’t wishing that tech leaders didn’t have a stronger handle on ethics, gender issues, history, and politics?) Expect that to come through in my newsletter and this blog.

So, if you’re looking for business advice neatly prepared into one-size-fits-all hermetically-sealed listicles, prepare to be gravely disappointed. If you want pragmatic insight into business from someone who experienced a lot and you also appreciate the occasional link to a video of the very last Sex Pistols show at Winterland in SF in 1978 or Orson Welles interviewing Andy Kaufman or an illustrated guide to Guy Debord’s “The Society of the Spectacle,” I’m your guy.  (Subscribe here.)

Remembering Evelyn McNeill

In the “old days” of the web, occasionally you would come across a subject that hadn’t been covered before and if you wrote about it, you could quickly become authoritative on the subject. There was an altruism to the whole endeavor as sometimes you were surfacing history that was not broadly known. See this old Metafilter post from 2005 about the ruins of the Belgum Sanitarium in the Berkeley hills, for which I briefly became an “authority” for doing nothing but taking photos and writing about it. It’s with a similar spirit that I want to do my part in recording for posterity the life of Evelyn McNeill, who I was thinking about today. Evelyn’s legacy is meaningful to me and many others.

Evelyn McNeill was a friend of mine who passed away at age 86 on July 20, 2016. Just before her death, she wrote a book about her incredible life: Zero to Eighty Over Unpaved Roads: A Memoir. I was honored that she asked me to write the foreword (pasted below this post) in August 2013.

Evelyn was a neighbor who was a customer of my and my brother’s lawn-mowing business when we were kids (in the Acknowledgements of her book, she wrote: “I am proud to see how far he has gone since the years he mowed my lawn!”) She was the first female faculty member at the East Carolina University School of Medicine (where she taught Neuroanatomy) and in the late 1970s filed a complaint against the school with the Equal Employment Opportunity Commission when she found that she was being paid less than men with equal responsibilities. She won that case in a time when such cases were nearly unheard of (this episode and all of its complexity is covered over 10 full pages in her book). Evelyn was a patriotic feminist who served in the Army and later in the Army Reserves over the course of 36 years. When she retired in 1989 as a colonel, she was awarded the Legion of Merit, an award commissioned by the President and given for “exceptionally meritorious conduct in the performance of outstanding services and achievements.” Evelyn lived a life of service, always loving and dutiful in the way she conducted herself but never afraid to be tough and speak up for herself.evelyn and me

When I sent her the draft of my foreword, she told me that what I wrote was “overly generous.” It really wasn’t if you knew her. I was fortunate to reconnect with her in the years before she passed. I came to my hometown of Greenville, NC in 2014 to speak to her Rotary Club (that’s me posing with her as she holds a copy of her book). When I was asked to speak at the Duke Fuqua Distinguished Speaker Series in March 2013 (YouTube), she was in the audience (she had gotten her Masters at Duke) and we had dinner afterwards.

Evelyn McNeill was a remarkable woman. I’ve never met anyone quite like her. I’m posting this in hopes that the fullness of Evelyn’s life and impact lives on the web for a very long time. I’ve pasted the foreword I wrote for her book below along with some links. I’ll close with the words that close the Introduction to her book:

. . . that journey has carried me where I never thought I could go. I have peered into places of hurt, sadness, and even bitterness that arose along the way. But this exercise in looking back has allowed those few inevitable elements to fall away and lifted me closer than ever to that concept of Christ-like love that surpasses all understanding.

So in these pages, my nieces will indeed find an aunt who lost love, but found it again and again; and one who felt the void of not having children of her own, but never grieved over it. In the happy faces of my siblings’ children and grandchildren, after all, I can see my mother and father and the legacy of love they left behind.

If there’s a common theme that can be attached to the pages of this book, let it be found in two words so often attached to the bumpers of cars driven by Christians these days:



Foreword from Evelyn’s book, Zero to Eighty Over Unpaved Roads: A Memoir

When I was a young boy in the early to mid-1980s, I lived in Greenville, N.C. My brother and I had a relative lawn-mowing empire for two boys: about twenty-five lawns in total.  One of our most loyal customers was Evelyn McNeill, whose home was just two doors down from our own. Of all the people we served, I enjoyed working at Evelyn’s house the most. While many of our customers strived to keep their lawns simply neat during the warm months, what I could only call a landscape around her property transcended the very idea of a “lawn” in its beauty, aesthetic taste, and attention to detail. As a young boy curious about the world, I marveled at her vast array of carefully labeled plants along the well-tended paths in her wooded garden. The woods now contain a custom-built tree house, a playful touch that a boy like me could really appreciate. An adult with a tree house! It illustrated the exquisite taste, care, and joie de vivre that Evelyn demonstrated to me in everything she did, from her research to her gardening to caring for her dear mother.

Evelyn was the first Ph.D. I ever met in my life. In fact, until I went off to college, when I heard someone say “Ph.D.,” my mental image was of Evelyn. Her beautiful study with all the signs of rigorous intellectual thought inspired me as a young boy to always be engaged in the world of ideas and the joys of living a life of the mind. Her unbridled curiosity about everything from architecture to horticulture to medicine to art inspired me to be a well-rounded person and a citizen of the larger world.

I will always recall with fondness Evelyn’s gift to me for high school graduation: a set of luggage. Although at that point I had never even flown on a plane, I understood the gift as a subtle suggestion to go see the world, learn new things, and meet new people. Since then, I’ve developed a love for travel and learning about new cultures around the world, and it started with that generous and inspired gift.

Evelyn is a remarkable and dare I say iconoclastic woman. I spent ten years in Berkeley, California, where iconoclasts are a dime a dozen. I learned there that the true iconoclasts among us are the ones who quietly challenge convention in ways that don’t attract newspaper headlines, as Evelyn has done in her life and work. Evelyn is a humble iconoclast, a woman who pursued a career without family or children of her own, but always showed the love of a mother toward the children of her extended family and kids like me, who she inspired with her sharp mind and boundless generosity.

This is the story of her life and the people she has touched and shaped along the way. I am incredibly lucky to count myself among them.

Chad Dickerson

August 2013 / Brooklyn, NY

Serving as a Cornell Tech Fellow

I recently accepted a role as a Cornell Tech Fellow at the new campus on Roosevelt Island, which officially opened last week. I’m working under the direction of Dan Huttenlocher, the dean and leader of Cornell Tech. I have a desk there and be on campus a day or so a week helping Dan with a variety of initiatives as he builds and scales this important new institution (which is very much a entrepreneurial startup).

Cornell Tech is the outcome of the kind of public/private partnerships with world-changing ambition that reflect the civic character of New York City so well. I’ve always been fascinated with how things work and I’m excited to see a new world class campus develop up close from day one. The launch of the campus is a huge moment for New York City and something that will impact generations.

I first met Dan in 2011 when we gave Cornell space to do an alumni event at Etsy. At that time, there was a competition amongst top universities around the world to occupy a new tech campus on Roosevelt Island. Stanford, MIT, Carnegie Mellon, and Cornell were among the 18 contenders. Cornell won the bid with Dan as the leader and six years later (after a few years in Google-provided quarters in Chelsea), the campus is fully operational. I’ve been involved in various ways with Cornell Tech for a few years now, giving a welcome talk to the incoming classes the past two years and as a guest in the Conversations in the Studio series. Every time I have talked with students there, I feel more optimistic about the future of the world. The future is in good hands at Cornell Tech.

I’m excited to be a small part of it. Congratulations to everyone who had a role in launching the new campus, particularly Dan!

Select media coverage

Becoming an advisor to Bandcamp

Just a few weeks ago, I wrote that I wasn’t making any significant commitments until the end of 2017, including advisory roles. Well, I should have put an asterisk on that. Earlier this week, I signed up as an advisor to Bandcamp and I couldn’t be more excited about it. 

This formal advisory role happened really organically. I’ve been talking with the Bandcamp team informally for years and have always loved what they are doing and how they are doing it. Way back in the summer of 2010, I had lunch with Ethan Diamond and Shawn Grunberger, the co-founders of Bandcamp, and we compared notes on a lot of topics (I was CTO at Etsy then). Over the years, we’ve kept in touch. I just happened to have a lunch set up with Ethan and Josh Kim (Bandcamp COO) the week of the Etsy announcement and it was really fun. They asked me to be an advisor and I couldn’t resist getting involved. (Note: this doesn’t mean I’m looking more generally for other opportunities. Bandcamp and their focus on music just uniquely fits into how I want to be spending my time.)

Here are just a few of the things I love about Bandcamp:

1. The music

I love music and particularly love the independent music ecosystem and its constituent parts: the bands, the labels, the venues, college radio, music writers, and platforms like Bandcamp. Way back in the day, I ran the Duke Coffeehouse (more of that story here) and briefly had a show on WXDU. I have spent a lot of time in my life nerding out with friends on the aesthetics and taste of various indie labels and consuming vast quantities of music writing. I’ve long had a habit of throwing a handful of 33 ⅓ books into my carry on bag (the best book series of all time and the perfect form factor for travel — be sure to check out if you love music).

Back to the music: today I’m very much enjoying Agent blå’s self-titled record, which is the Bandcamp Daily “album of the day.” (more on Bandcamp’s awesome editorial below). This is great writing: “Skörvald, Gustavsson, and Alatalo used to play Joy Division covers together at local open mics, and Agent blå manages to capture all of that group’s darkness with none of the nihilism.” For people who’ve been looking for Joy Division without the nihilism or just about any other bands that operate outside of the Music Industry Industrial Complex, Bandcamp delivers.

2. The vision

It’s not just the music, it’s the vision and philosophy behind the company. From their about page: “Bandcamp makes it easy for fans to directly connect with and support the artists they love. We treat music as art, not content, and we tie the success of our business to the success of the artists who we serve.” Yes!

3. Artist-friendly model

The ethos is expressed in Bandcamp’s Fair Trade Music Policy: “Bandcamp believes that music is an indispensable part of culture, and for that culture to thrive, artists must be compensated fairly and transparently for their work.” But it’s not just an aspiration. The economics are also completely transparent and artist-friendly. Bandcamp’s share is 15% on digital items, and 10% on physical goods plus payment processing fees. Everything else goes to the the artist, usually 80-85%, and they pay out daily. This is how you build a “fair, sustainable music economy” (as the policy states). That’s awesome and no one else is doing it like Bandcamp.

4. Sustainable long-term operating model coupled with founder control

Bandcamp was founded in 2008 and has been profitable since 2012. They haven’t taken much outside money and maintain full control of the company.**

5. Excellent editorial.

I love great music writing and the team at Bandcamp clearly does, too. They hired a top-notch editorial staff and launched Bandcamp Daily about a year ago (see launch post for more on the vision). My favorite feature right now is “Better Know a College Radio Station.” Reading Bandcamp Daily feels like hanging out in a good neighborhood record store or having a conversation with a friend who’s hanging out with you at 2am at the college radio station helping you pick the next track you’re going to play.

I’m looking forward to helping the Bandcamp team out in any way they find my help useful — should be very fun!

** (elaborating on point #4 above) I’ll probably write more about this at some point, but I learned a lot about financing, ownership structure, and control over my tenure at Etsy. When I joined Etsy as CTO way back in 2008, the intention to be a public company had been stated months earlier (“Our goal is for Etsy to be an independent, publicly traded company.”) We didn’t go public until 2015, but five rounds of venture financing even before I stepped up to CEO in 2011 were very clear steps along that path. Nothing wrong with that — it’s the way things work when you take venture money, unless you want to sell the company — but that’s a particular path and Bandcamp has set itself up to go down a different road and that’s really interesting.

What’s next?

Update 9/21/2017 (original post from 05/15/2017 below): Since I posted this originally about four months ago, a lot has happened. Almost no one who was in my position as a CEO ever writes openly about life after a big, difficult change. From the very beginning, such changes are typically slathered in the conventional PR sheen of “spending more time with my family” and “seeking new opportunities.” I’ve always hated that, which is why when I left Etsy, I personally insisted on the release saying what happened. As they say, “it is what it is” and I had a great run over close to a decade. I mention how I handled my departure here months later because looking back that was an important first step in doing my best to live the rest of my life with no bullshit and no illusions. Life is really too short to live that way.

Being very public about my intentions back in May gave me the space to proactively fine-tune how I want to spend my time instead of immediately filling my days with random meetings. It forced me to sit and think about what I wanted to be rather than filling my life with activity and falling prey to others’ expectations of what I should be. Since then, I’ve had a great summer spending undistracted time with my family and friends. I’ve gotten to know my six year old son in a very deep way and there’s no better gift in life than that. I’ve spent a lot of time writing, reflecting on successes and mistakes, advising/coaching a handful of people (going deep in an unhurried way, not just “let’s have coffee on X topic”), and generally just being a friend to people I care about (including myself).

I’ve been working harder than ever, but on things that matter a lot to me that may not matter that much (if any) to other people. I’ve said “no” to just about everything that people have sent my way (which turns out to be something that Warren Buffett recommends). My time away so far has been brief by comparison, but this Rolling Stone interview with Patti Smith after sixteen years out of the public eye really resonates with me:

Q: As far as your fans and the music business were concerned, you literally disappeared during the 1980s. How did you and Fred [her husband] spend those missing years?

A: That was a great period for me. Until Jackson had to go to school, Fred and I spent a lot of time traveling through America, living in cheap motels by the sea. We’d get a little motel with a kitchenette, get a monthly rate. Fred would find a little airport and get pilot lessons. He studied aviation; I’d write and take care of Jackson. I had a typewriter and a couple of books. It was a simple, nomadic, sparse life.

Q: Was there a period of adjustment for you, going from rock & roll stardom to almost complete anonymity?

A: Only in terms of missing the camaraderie of my band [I certainly identify with this. -CD]. And I certainly missed New York City. I missed the bookstores; I missed the warmth of the city. I’ve always found New York City extremely warm and loving.

But I was actually living a beautiful life. I often spent my days with my notebooks, watching Jackson gather shells or make a sand castle. Then we’d come back to the motel. Jackson would be asleep, and Fred and I would talk about how things went with his piloting and what I was working on.

Because people don’t see you or see what you’re doing doesn’t mean you don’t exist. When Robert [Mapplethorpe] and I spent the end of the ’60s in Brooklyn working on our art and poetry, no one knew who we were. Nobody knew our names. But we worked like demons. And no one really cared about Fred and I during the ’80s. But our self-concept had to come from the work we were doing, from our communication, not from outside sources.

That’s the spirit of how I’ve been living. I’m doing what truly excites me (see my post about Bandcamp and my post about Cornell Tech) and with very few exceptions keeping my calendar free and clear. I’m keeping that as a permanent practice. Now that I’ve got a basic life rhythm worked out, I’m glad to entertain opportunities that are really special and deliver a clearly positive societal impact.  This would include boards (non-profit, for-profit, NGO), advisory roles, and investment opportunities with clear positive social impact. I’m not interested in “all in” full-time roles right now. Once I’m in something, I give it everything and more. “All in” has always meant 150% commitment and I’m not interested in that kind of life right now.

More generally, I’m troubled about what is happening in our country and world today and want to spend my energies on things that help put us all on a better track. I’m doing some things quietly but am always open to new ideas and approaches. If there’s something you’re working on in that spirit and you think I could be helpful, email me at hello at I’m continuing to keep my bar for engagement very high, so send as much detail up front about what you’re working on and how you think I might be helpful. There are lots of challenges in the world today, but I’m hopeful and optimistic that we can address them.

Original post 05/15/2017: Since the announcement on May 2 that I was stepping down as CEO of Etsy (official release), I’ve gotten so many kind notes and emails over the past couple of weeks from all the amazing people I’ve had the honor to work with over the course of my time at Etsy and well before that. I’ve been responding to all of those and enjoying it immensely. Anyone who is wondering how to get in touch with me, you can email me at

People keep asking me, “what’s next?” My only two commitments are that:

  1. I’m staying in NYC, Brooklyn specifically. I love it here. It’s the greatest city in the world!
  2. I’m not making commitments of any kind through the end of 2017. That includes:
  • Job opportunities
  • Board seats
  • Advisory roles
  • Speaking gigs
  • Coffees / lunches / dinners far in advance. I’m *really* serious about not jamming up my calendar with future engagements. Feel free to call/text/email a couple of days before or the day of.

Being the CEO of Etsy for nearly six years and CTO for three years before that during a period of massive growth was completely all-consuming and a 24/7/365 job. I loved it but look forward to days that are open to spontaneity — ones that aren’t scheduled to the brim from morning until night.

I plan to be very busy, though. Aside from some travel and time with family, I’m going full maker’s schedule and plan to focus my energies on a couple of creative pursuits: writing and music. I loved serving creative people in my job at Etsy and am grateful to all sellers around the world for giving me that opportunity. Now I look forward to being on the creative side myself. I have some exciting ideas and it will be fun to see where they lead.

Stay tuned.

Chad guitar 2013

Words of advice to inside sales people prospecting busy CEOs

If you’re an executive at a company and are in any way accessible, you’re on the receiving end of dozens of email pitches for products and services every week. Most of these come from what are known as “inside sales” people, i.e. sales people who start at the top of the funnel to find qualified leads for the company. They tend to cast their nets really wide and send lots of emails and make lots of phone calls.

Here’s one pitch I got recently:

Hi Chad,

I’ve reached out several times to discuss your [type of software service] initiatives for 2013.

If you have just been busy, and this is something you would like to pursue, I am happy to set some time up based on your availability.
Otherwise I will reach out again in a few months.

Let me know

This particular inside sales person was unusually persistent (this had to be the 5th or 6th email with no new information, just asking for time), and he showed many of the same ineffective patterns that I’ve seen for years. I decided to write him back with some advice. I’m publishing my response on the hope that it will help salespeople produce better pitches (which will thereby reduce the number since they will have to be more thoughtful), and saving that, maybe my post will provide some cathartic commiseration to all of the other people who I know face a similar barrage of unqualified pitches every day (and I won’t even get into the cold phone calls). The subject line of his last email was “Just busy?”

 Hi [name redacted], 

I know you’re just doing your job, but I wanted to give you some feedback as a busy CEO you are prospecting. Please take the below in that spirit — I’m just trying to be helpful. It looks like [your company] has an excellent management team, and I’m sure the team is doing really interesting work. 

A few key points: 

1. Your level of persistence is verging on annoying. I admire persistence, but the tone of your emails suggests that you are more focused on solving your problem (finding leads for your product) than mine. There is nothing in your emails that suggest you have done any homework on Etsy’s business and what we might need. I’ve written a lot about what Etsy is doing and I’m surprised that sales people like you don’t at least try to pull some of the content for the pitch ( I feel like I’m on a long list of people you are cold-calling, you’re just looking for a “hit,” and I’m just a reminder in your database.

2. If you look at my background, my background is heavy on technology and my path to CEO included being CTO of multiple companies. Your emails are very superficial given that I know this space pretty well. I’ve received hundreds of pitches over the years, and the ones that stand out are the ones that speak to the real needs of people doing the work of running large-scale Internet companies. Your pitch doesn’t reflect any knowledge about me personally and what I might already know from past experience.

3. As a CEO of a growing company, I generally have no availability. Nothing in your emails has made me feel like I need to carve out time from my schedule to meet with you. Simple repetition is not a strategy.

4. I had to look at your web site to see that the management team did some category-defining work with [well-known company in this person’s space]. You should sell that more. Don’t make your prospects do all the work of figuring out why they should answer your emails.

All that said, we’re not interested at this time, so you don’t need to email me again. Best of luck with your prospecting.