🔎
May 13 2021

Startup CXO: the Sequel to Startup CEO

As I finished up my work on the Second Edition of Startup CEO:  A Field Guide to Scaling Up Your Business and started working on a new startup, my colleagues and I started envisioning a new book as a sequel or companion to Startup CEO that is going to be published on June 9 with our same publisher, Wiley & Sons.  The book is called Startup CXO:  A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Simply put, the first book left me with the nagging feeling that it wasn’t enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to grow a company?  If you’re leading HR, or Finance, or Marketing, or any key function inside a startup, what resources are available to you? What should you be thinking about?  What does ‘great’ look like?  What challenges lurk around the corner as you scale your function that you might not be focused on today?  If you’re a CEO who has never managed all these functions before, what should you be looking for when you hire and manage all these people?  If you’re an aspiring executive, from entry-level to manager to director, what do you need to think about as you grow your career and develop your skills?

Startup CXO is a “book of books,” with one section for each major function inside a company.  Each section is be composed of 15-20 discrete short chapters outlining the key “playbooks” for each functional role in the company – Chief People Officer, Chief Financial Officer, Chief Marketing Officer, Chief Revenue Officer, etc., hence the title Startup CXO – which is a generally accepted label in the startup ecosystem for “Chief ____ Officer.”

Here are the front and back covers of the book, with some great endorsements we’re so proud of on the back.

This is an important topic to write about at this particular time because America’s “startup revolution” continues to gather steam.  There are only increasing numbers of venture capital investors, seed funds, and accelerators supporting increasing numbers of entrepreneurial ventures.  While there are a number of books in the marketplace about CEOs and leadership, and some about individual functional disciplines (lots of books about the topic of Sales, the topic of Product Development), there are very few books that are practical how-to guides for any individual function, and NONE that wrap all these functions into a compendium that can be used by a whole startup executive team.  Very simply, each section of this book serves as a how-to guide for a given executive, and taken together, the book will be a good how-to guide for startup executive teams in general.

Startup CXO has my name on it as principal author, and I’m writing parts of it, but I can’t even pretend to write it on my own, so the book has a large number of contributors who have the experience, credibility, and expertise to share something of value with others in their specific functional disciplines — most of my Bolster co-founders are writing sections, and the others are being written by former Return Path executive colleagues — Jack Sinclair, Cathy Hawley, Ken Takahashi, Anita Absey, George Bilbrey, Dennis Dayman, Nick Badgett, Shawn Nussbaum, and Holly Enneking.

Startup CXO is also pretty closely related to Bolster’s business, since we are in the business of helping assess and place on-demand CXO talent, and as such, the final section of the book has a series of chapters written by Bolster members who are career Fractional Executives about their experience as a Fractional CXO.

The book is available for pre-order now at Amazon and Barnes & Noble.

Oh, and stay tuned for a third book in the series (kind of) due out late this year. More on that over the summer as the project takes shape!

Feb 21 2007

Book Short: Next, Write a Sequel

Book Short:  Next, Write a Sequel

Written by Rodd Wagner and James K. Harter and billed as “the long awaited sequel to First, Break All the Rules” (one of the best management books I’ve ever read), I thought 12: The Elements of Great Managing, was good, but not great.  12…, along with the original book First… and Now, Discover Your Strengths, the latter two both by Marcus Buckingham, are all based on an extensive database of research done on corporate America by the Gallup organization over many years.  All three are valuable reads in one way or another, although I found this to be the weakest of the three.  (Note that Now… is different from the other two in that it’s not about management, it’s about self-management — very different, though based on the same research.)

Anyway, the elements of great managing, so say the authors, is all about creating employee engagement.  I totally buy into that.  And since no book short on 12… would be complete if it didn’t list out the 12…

1. Do I know what is expected of me at work?
2. Do I have the materials and equipment I need to do my work right?
3. At work, do I have the opportunity to do what I do best every day?
4. In the last seven days, have I received recognition or praise for doing good work?
5. Does my supervisor, or someone at work, seem to care about me as a person?
6. Is there someone at work who encourages my development?
7. At work, do my opinions seem to count?
8. Does the mission/purpose of my company make me feel my job is important?
9. Are my co-workers committed to doing quality work?
10. Do I have a best friend at work?
11. In the last six months, has someone at work talked to me about my progress?
12. This last year, have I had the opportunities at work to learn and grow?

The book fleshes out each of the 12, gives examples (some of which are better/clearer than others), and then addresses compensation in a very interesting chapter at the end.  Key takeaways on comp:

– Higher pay doesn’t guarantee greater engagement
– Good and bad employees are equally likely to think they deserve a raise
– Money without meaning isn’t enough
– Most employees, most of the time, feel undercompensated
– Individual pay can/should be private, but comp criteria should be very public
– People who feel well-compensated generally work harder

The book also cites a very provocative article suggesting that organizations would handle comp better if they made everyone’s comp public (in contrast to the final bullet above, yes).  I’m going to write more about compensation in future postings, so I’ll leave this section on those notes.

Finally, the book’s two closing thoughts are perhaps its most prescient:  one critical element of BEING a great manager is HAVING a great manager; and the managers who put the most into their people, get the most out of their people.

Jan 10 2013

Book Short: Entrepreneurial Lessons

Book Short:  Entrepreneurial Lessons

The Startup Playbook: Secrets of the Fastest-Growing Startups from 42 Founders, by David Kidder, is the ultimate coffee table book for entrepreneurs and people who are interested in how they think about running their businesses.

David is the author of the Intellectual Devotional series (here’s a link to one of the five or six books in the series), he’s a good friend of mine and a member of a CEO Forum that I’m in, and my major disclosure about this blog post is that I’m one of the 42 entrepreneurs David interviewed for and profiles in the book.

The Startup Playbook is very different from my own book (in progress) on being a Startup CEO.  Where my book is going to go deep on different topics – think of it as a bit of a field guide – David’s book is extremely broad in its coverage of different entrepreneurs and their stories.  Taken together, the book paints a great picture of how CEOs think about the most important parts of the job.  It’s also a nice change of pace (for me, anyway) that David profiles some entrepreneurs who aren’t in the Internet/tech space.

It was an honor to be included in The Startup Playbook next to entrepreneurs like Reid Hoffman and Elon Musk.

Oct 27 2022

Book Short: New Advice from an Old Friend

In 2005, I wrote a post called Unfolding the Map in which I looked at these two seemingly opposing philosophies from successful entrepreneurs:

  • If you don’t have a map, you can’t get lost
  • If you don’t have a map, you can’t get where you’re going

and tried to combine them when thinking about product roadmapping. The same contradiction and combination could be applied to anything, including coaching and development.

That’s why I was excited to read my friend Matt Spielman’s new book, Inflection Points: How to Work and Live with Purpose. Matt worked at Return Path twice over the years — first as employee #3 (more on that in a minute) and then over a decade later as CMO. We live near each other and know each other’s families. I’ve been lucky enough to see his career unfold and develop into what it is today, a flourishing coaching business called Inflection Point Partners that helps clients tremendously…and that also feeds Matt’s soul.

When I first met Matt and he joined me and Jack to launch Return Path in 1999, he was fresh out of business school and focused on sales and marketing from his prior career in investment banking. Our idea was that he would do the same for us as we got our product in market. But as I started focusing more on what kind of company we wanted to build and how to get there, Matt became my leading thought partner on those topics. When we got to about 25 people, he and I created a new role for him — head of Human Capital and Organization Development. While a bit clunky, that title meant that Matt was the principal person helping me create at small scale what we later branded our People First philosophy. That philosophy and the practices we developed out of it led to 20 years of a strong track record of investing in people and helping over 1,300 colleagues grow their careers by being simple, actionable, and broad-based in the way we handled feedback and development planning. This started back in 2000.

Matt’s book puts the ethos that I saw percolating over 20 years ago into a tight framework around his coaching methodology of the GPS (Game Plan System). The book is short and sweet and walks through both the philosophy and the framework in accessible terms. And while it’s true that you have to be open to new ideas, open to serendipity, and go with flow sometimes…it’s also true that if you have specific goals in mind, you are unlikely to achieve them without a focused effort.

I’ve written a lot about coaching lately between The Impact of a Good Coach and another recent post about a strong coaching framework about intentionality in Russell Benaroya’s book. In that second post, I noted that “While I have become less and less of a life planner as I’ve gotten older under the headline of ‘man plans, God laughs,’ I am a huge believer in being intentional about everything. And that pretty much sums up Matt’s book: If you don’t have a map, you can’t get where you’re going.

Oct 31 2019

Book Short – You’re in Charge – Now What?

Thanks to my friend and long-time former Board member Jeff Epstein, I recently downed a new book, You’re in Charge – Now What?, by Thomas Neff and James Citrin.  I’m glad I read it.  But it was one of those business books that probably should have just been a Harvard Business Review article.  It’s best skimmed, with helpful short summaries at the end of every chapter that you could blow through quickly instead of hanging on every word. 

The authors’ 8-step plan is laid out as:

  1. Prepare yourself during the countdown
  2. Align expectations
  3. Shape your management team
  4. Craft your strategic agenda
  5. Start transforming culture
  6. Manage your board/boss
  7. Communicate
  8. Avoid common pitfalls

Ok fine, those make sense on the surface. Here are three things that really stood out for me from the book:

First, “working” before you’re officially working – the countdown period. I tried hard NOT to do this when I was between things, but I’m glad I did the things I did, and now, I wish I had done more. The most poignant phrase in the book is “scarce time available during your first hundred days.” That is an understatement. As my “to read” pile grows and grows and grows with no end in sight…I wish I had done more pre-work.

Second, remember that in every interaction, you are being evaluated as much as you are evaluating. And note that for many people, they will be thinking very critically, things like “do I want to work with this person…is he/she showing signs that he/she wants to work with me?” Yes, we all know as leaders, we live in a fishbowl. But I think that may be even more true during the first couple months on the job.

Finally, this phrase stood out for me: “Acknowledging and in some cases embracing your predecessor can sustain a sense of continuity within the organization and instill a sense of connectivity with employees’ shared past.” There is frequently a temptation to focus on things that need change, which invariably there are…and which invariably you will hear from people who are happy to find a willing new ear to listen to them. But this posture of acknowledge/embrace is especially true in my case, where my predecessor is the founder and 25-year CEO who continues on as our active chairman.

I know there are a ton of books like this on the market, and while I’ve only read this one, I’d say that if you’re starting a new CEO or executive-level job, this is a good one to at least skim to get some ideas.

Mar 29 2006

Book short: Myers-Briggs Redux

Book short:  Myers-Briggs Redux

Instinct:  Tapping Your Entrepreneurial DNA to Achieve Your Business Goals, by Tom Harrison of Omnicom, is an ok book, although I wouldn’t rush out to buy it tomorrow.  The author talks about five broad aspects of our personalities that influence how we operate in a business setting:  Openness to Experience, Conscientiousness, Extroversion, Agreeableness, and Neuroticism.  These traits are remarkably similar to those in the popular Myers-Briggs Type Indicator that so many executives have taken over the years.

It’s not just that you want to be high, high, high, high, and low in the Big 5.  Harrison asserts that successful entrepreneurs need a balance of openness and conscientiousness in order to be receptive to new ideas, but be able finish what you start; a balance of extroversion and agreeableness so that you have enough energy but also have the ability to work with others; and not too much neuroticism, as you have to be able to take risks.

The book not only talks about how to spot these factors, but how to work around them if you don’t have them (that part is particularly useful, but he doesn’t do it for all five factors).  He also talks about the entrepreneurial addiction to success, and creating the all-important Servant CEO culture, which I certainly agree with and wrote about early on in this blog in my “Who’s The Boss?” posting.

Harrison does have a great section on how “Nice Guys” can and should be winners; how being nice and having guts aren’t mutually exclusive, and he gives a well-written Twelve Rules for expressing the Nice Guy gene:

– Don’t walk on other people, but don’t let them walk on you

– Respect the big idea in everyone

– Own everything

– Never let ’em see you sweat Keep it simple

– Never think in terms of “So what have you done for me today?”

– More is less

– Live your word consistently

– Don’t lie:  fix what’s causing you to think you need to lie

– Never forget to thank, congratulate, or acknowledge people for their efforts

– Keep your door and your heart open

– Never stand in the way of balance

The most annoying part of the book is that Harrison keeps making references to a handful of genetic studies about twins to prove on and off that traits are inherited and that inherited traits can be expressed in different ways.  These references are mildly interesting, but they detract from the substance of the book.

Overall, the book has some interesting points in it, but it’s too much like Jim Collins’ Good to Great and Built to Last, only without the depth of business research and case studies.  Plus, Harrison does the one thing I find most irritating in business books — he is clearly an expert in one thing (business), but he unnecessarily pretends to be an expert in another thing (genetics) in order to make his point.

Jan 5 2023

Book Short: Must-Read for CXOs

Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, by Sarah E. Brown, is an amazing book – and one that fits really well with our Startup Revolution series, in particular our book Startup CXO.

I kept thinking as I was reading it that it was the other side of the proverbial coin…that Startup CXO was about the details of each executive job in a company…but Sarah’s book is about the things common to ALL executive jobs – how to get them, how to succeed at them, essentially how to BE an executive. I read it front to back in a single day one weekend and loved it.

Some of the most insightful moments in her book are:

  • Why big company executives who join startups often struggle
  • How to get promoted by proactively doing the next job – act “as if” – while still excelling at your current job
  • The importance of managing to the CEO’s preferred work style (personally…I’d debate this – I think CEO’s should manage to their CXOs’ work styles or at least make it a two-way street, but her point is very valid!)
  • Why executives shouldn’t just up and quit with “two weeks’ notice” but that executives also need to be mentally prepared to be shown the door when they resign
  • The importance of getting your hands dirty and not being “above” doing the work of your team
  • Mastering the art of data-driven storytelling

Sarah quotes a number of CEOs throughout the book who I know and respect, from Nick Mehta at Gainsight to Mindy Lauck at Broadly. It was fun to read the book and see a number of very familiar names in it along the way.

Sarah and I did an interesting format – sort of a “dueling fireside chat” about our respective books on a webinar last fall. We had a fantastic conversation that could have gone on for hours. If you’re an executive – or an aspiring executive – you should go read her book.

Feb 2 2017

Book Short – A Smattering of Good Ideas that further my Reboot path

Book Short – A Smattering of Good Ideas that further my Reboot path

Ram Charan’s The Attacker’s Advantage was not his best work, but it was worth the read.  It had a cohesive thesis and a smattering of good ideas in it, but it felt much more like the work of a management consultant than some of his better books like Know How (review, buy), Confronting Reality (review, buy), Execution (review, buy), What the CEO Wants You to Know ( buy), and my favorite of his that I refer people to all the time, The Leadership Pipeline (review, buy).

Charan’s framework for success in a crazy world full of digital and other disruption is this:

Perceptual acuity (I am still not 100% sure what this means)

  1. A mindset to see opportunity in uncertainty
  2. The ability to see a new path forward and commit to it
  3. Adeptness in managing the transition to the new path
  4. Skill in making the organization steerable and agile

The framework is basically about institutionalizing the ability to spot pending changes in the future landscape based on blips and early trends going on today and then about how to seize opportunity once you’ve spotted the future.  I like that theme.  It matches what I wrote about when I read Mark Penn’s Microtrends (review, buy) years ago.

Charan’s four points are important, but some of the suggestions for structuring an organization around them are very company-specific, and others are too generic (yes, you have to set clear priorities).  His conception of something he calls a Joint Practice Session is a lot like the practices involved in Agile that contemporary startups are more likely to just do in their sleep but which are probably helpful for larger companies.

I read the book over a year ago, and am finally getting around to blogging about it.  That time and distance were helpful in distilling my thinking about Charan’s words.  Probably my biggest series of takeaways from the book – and they fit into my Reboot theme this quarter/year, is to spend a little more time “flying at higher altitude,” as Charan puts it:  talking to people outside the company and asking them what they see and observe from the world around them; reading more and synthesizing takeaways and applicability to work more; expanding my information networks beyond industry and country; creating more routine mechanisms for my team to pool observations about the external landscape and potential impacts on the company; and developing a methodology for reviewing and improving predictions over time.

Bottom line:  like many business books, great to skim and pause for a deep dive at interesting sections, but not the author’s best work.

Mar 24 2005

From Blog to Book – Beyond Bullets

From Blog to Book – Beyond Bullets

Hats off to fellow blogger Cliff Atkinson, who has just published a book called Beyond Bullet Points.  Cliff and his company, Sociable Media, consult on PowerPoint and presentations and have a great theory about how to do great presentations.

They follow the “clear, simple, and please God not so boring” guidelines espoused by a number of us in the business world, including Brad and of course Seth.  (BTW, if you haven’t read Seth’s e-book/treatise on Really Bad PowerPoint, you should do that as well, although I can’t find a link to it at the moment.)

One of the coolest parts of the book is that it really started out as Cliff’s blog, Beyond Bullets, then got Microsoft’s attention, then became a book.  What a great demonstration of old and new media reinforcing each other!

Jul 28 2009

Book Short: Worth Buying Free

Book Short:  Worth Buying Free

The cynic in me wanted to start this book review of  Free: The Future of a Radical Price, by Chris Anderson, by complaining that I had to pay for the book.  But it ended up being good enough that I won’t do that (plus, the author said there are free digital versions available — though the Kindle edition still costs money).  At any rate, a bunch of reviews I read about the book panned it when compared to Anderson’s prior book, The Long Tail (post, link to book).

I won’t get into the details of the book, though you’ll get an idea from the paragraph below, but Anderson has a few gems worth quoting:

  • Any topic that can divide critics into two opposite camps — “totally wrong” and “so obvious” — has got to be a good one
  • Free makes Paid more profitable
  • Younger players have more time than money…older players have more money than time
  • Doing things we like without pay often makes us happier than the work we do for a salary
  • It’s true that each generation takes for granted some things their parents valued, but that doesn’t mean that generation values everything less

While Free is s probably not quite as good as The Long Tail, it does a good job of organizing and classifying and explaining the power of different economic models that involve a free component, and I found it very thought provoking about our own business at Return Path.

We already do a couple forms of Free — we practice the “third party” model, by giving things away to ISPs but selling them to mailers; and we practice Freemium by providing Senderscore.org and Feedback Loops for free in order to attract paying customers to our testing and monitoring application and whitelist.  But could we do others?  Maybe.  They may not be revolutionary, but they’re smart marketing.

As some of the reviewers write, the book isn’t the be-all-end-all of marketing, it overreaches at times, and it is more applicable to some businesses than others, but Free was definitely worth paying for.

Jan 16 2006

Book short: Proto Gladwell

Book short:  Proto Gladwell

I’m sure author Robert Cialdini would blanch if he read this comparison, but then again, I can’t be the first person to make it, either.  His book, Influence:  The Psychology of Persuasion, is an outstanding read for any marketing or sales professional, but boy does it remind me of Malcolm Gladwell’s The Tipping Point and Blink (book; blog post).  Of course, Cialdini’s book came out a decade before Gladwell’s!  Anyway, Influence is a great social science look at the psychology that makes sales and marketing work.

Cialdini talks about sales and marketing professionals as “compliance practitioners,” which is a great way to think about them, quite frankly.  He boils down the things that make sales and marketing work to six core factors: consistency, reciprocation, social proof, authority, liking, and scarcity.

Reciprocation – we hate being in a state of being beholden so much that we might even be willing to do a larger favor than the one done for us in order to remove the state.  Think about “free gifts” in merchandising as an example of this, or being in a negotiation where someone trying to make a cold sale on you offers a fallback, smaller sale.  For example, you don’t want to buy anything from the boy scout, but after you say no to the $5 raffle ticket and he asks about the $1 candy bar, you feel more obligated to buy the $1 candy bar because the boy scout has “given” on his initial request.

Consistency – once we have made a choice, personal and interpersonal pressures force us to back it up and justify our earlier decision – even more so when in writing or when declared to others.  This is why marketers love getting testimonials from customers; the testimonial locks the customer in emotionally, as well as encouraging others to buy the product.

Social proof – if others think it’s correct, it must be correct, especially if those other people are like us.  There are some scary examples in the book here, such as Reverand Jim Jones and The People’s Temple mass suicides.  Gripping, but creepy.

Liking – we listen to people we like, and we like people to whom we’re similar or who are physically attractive.  This section was especially reminiscent of Blink, but with different and more marketer-focused examples.

Authority – we have an extreme willingness to listen to authority, even when the authority isn’t quite relevant.  This is why celebrity endorsements work so well.

Scarcity – we have a extreme motivation of fear of loss, either or something, or of the opportunity to have something.  Who doesn’t like to keep doors open as long as possible?

The one place the book falls down a little bit is in the sections at the end of each chapter talking about how to resist that particular technique through jujitsu – the art of “turning the enemy’s strength to your advantage.”  While nice in theory, Cialdini’s examples aren’t super helpful beyond saying “when you think you’re getting suckered, stop — and then say no.”

Overally, though, the book is well written and choc full of examples.  Thanks to marketer Mallory Kates for sending me this great book!