I’ve published two editions of Startup CEO, a sequel called Startup CXO, and am a co-author on the second edition of Startup Boards. We also just (2025) published mini-book versions of Startup CXO specifically for five individual functions, Startup CFO, Startup CRO, Startup CMO, Startup CPO, and Startup CTO.

You’re only a startup CEO once. Do it well with Startup CEO, a “master class in building a business.”

—Dick Costolo, Partner at 01A (Former CEO, Twitter)

Being a startup CEO is a job like no other: it’s difficult, risky, stressful, lonely, and often learned through trial and error. As a startup CEO seeing things for the first time, you’re likely to make mistakes, fail, get things wrong, and feel like you don’t have any control over outcomes.

As a Startup CEO myself, I share my experience, mistakes, and lessons learned as I guided Return Path from a handful of employees and no revenues to over $100 million in revenues and 500 employees.

Startup CEO is not a memoir of Return Path’s 20-year journey but a CEO-focused book that provides first-time CEOs with advice, tools, and approaches for the situations that startup CEOs will face.

You’ll learn:

How to tell your story to new hires, investors, and customers for greater alignment How to create a values-based culture for speed and engagement How to create business and personal operating systems so that you can balance your life and grow your company at the same time How to develop, lead, and leverage your board of directors for greater impact How to ensure that your company is bought, not sold, when you exit

Startup CEO is the field guide every CEO needs throughout the growth of their company and the one I wish I had.

“Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career.”

– Scott Dorsey, Managing Partner, High Alpha (Former CEO, ExactTarget)

One of the greatest challenges for startup teams is scaling because usually there’s not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. My team and I understand the scaling challenges—we’ve been there, and it took us nearly 20 years to scale and achieve a successful exit. Along the way we learned what worked and what didn’t work, and we share these lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a “CEO to CEO Advice” summary from me on what great looks like for that CXO, signs your CXO isn’t scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

A comprehensive guide on creating, growing, and leveraging a board of directors written for CEOs, board members, and people seeking board roles.

The first time many founders see the inside of a board room is when they step in to lead their board. But how do boards work? How should they be structured, managed, and leveraged so that startups can grow, avoid pitfalls, and get the best out of their boards? Authors Brad Feld, Mahendra Ramsinghani, and Matt Blumberg have collectively served on hundreds of startup and scaleup boards over the past 30 years, attended thousands of board meetings, encountered multiple personalities and situations, and seen the good, bad, and ugly of boards.

In Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, the authors provide seasoned advice and guidance to CEOs, board members, investors, and anyone aspiring to serve on a board. This comprehensive book covers a wide range of topics with relevant tips, tactics, and best practices, including:

• Board fundamentals such as the board’s purpose, legal characteristics, and roles and functions of board members;
• Creating a board including size, composition, roles of VCs and independent directors, what to look for in a director, and how to recruit directors;
• Compensating, onboarding, removing directors, and suggestions on building a diverse board;
• Preparing for and running board meetings;
• The board’s role in transactions including selling a company, buying a company, going public, and going out of business;
• Advice for independent and aspiring directors.

Startup Boards draws on the authors’ experience and includes stories from board members, startup founders, executives, and investors. Any CEO, board member, investor, or executive interested in creating an active, involved, and engaged board should read this book—and keep it handy for reference.

Five new mini-books from Startup CXO, but with new bonus material and an obvious focus on each specific functional area.

Each book has several topics in common – chapters on the nature of an executive’s role, how a fractional person works in that role, how the role works with the leadership team, how to hire that role, how the role works in the beginning of a startup’s life, how the role scales over time, and CEO:CEO advice about managing the role.

In Startup CTO (Technology and Product), the role-specific topics Shawn Nussbaum talks about are The Product Development Leaders, Product Development Culture, Technical Strategy, Proportional Engineering Investment and Managing Technical Debt, Shifting to a New Development Culture, Starting Things, Hiring Product Development Team Members, Increasing the Funnel and Building Diverse Teams, Retaining and Career Pathing People, Hiring and Growing Leaders, Organizing Collaborating with and Motivating Effective Teams, Due Diligence and Lessons Learned from a Sale Process, Selling Your Company, Preparation, and Selling Your Company/Telling the Story.

In Startup CMO, the role-specific topics Nick Badgett and Holly Enneking talk about are Generating Demand for Sales, Supporting the Company’s Culture, Breaking Down Marketing’s Functions, Events, Content & Communication, Product Marketing, Marketing Operations, Sales Development, and Building a Marketing Machine.

In Startup CFO, the role-specific topics Jack Sinclair talks about are Laying the CFO Foundation, Fundraising, Size of Opportunity, Financial Plan, Unit Economics and KPIs, Investor Ecosystem Research, Pricing and Valuation, Due Diligence and Corporate Documentation, Using External Counsel, Operational Accounting, Treasury and Cash Management, Building an In-House Accounting Team, International Operations, Strategic Finance, High Impact Areas for the Startup CFO as Partner, Board and Shareholder Management, Equity, and M&A.

In Startup CRO, the role-specific topics Anita Absey talks about are Hiring the Right People, Profile of Successful Sales People, Compensation, Pipeline, Scaling the Sales Organization, Sales Culture, Sales Process and Methodology, Sales Operating System, Marketing Alignment, Market Assessment & Alignment, Channels, Geographic Expansion, and Packaging & Pricing.

In Startup CPO (HR/People), the role-specific topics Cathy Hawley talks about are Values and Culture, Diversity Equity and Inclusion, Building Your Team, Organizational Design and Operating Systems, Team Development, Leadership Development, Talent and Performance Management, Career Pathing, Role Specific Learning and Development, Employee Engagement, Rewards and Recognition, Reductions in Force, Recruiting, Onboarding, Compensation, People Operations, and Systems.

I haven’t done short book summaries in a LONG time, but I’ll try to start adding that back into the mix as I read interesting and relevant books. Here’s one to add to your list: One Life to Lead, by Russell Benaroya. I was recently connected to Russell by a mutual friend, TA McCann at Pioneer Square Labs. TA had a sense Russell and I would hit it off, and we did. Russell is a multi-time founder/CEO, a Coach, and an author, so we have a lot in common.

One Life to Lead is an excellent book. First, it is short and easy to get through. Unlike a lot of business books, it doesn’t go on too long or contain anything extraneous. It’s to the point!

Second, the book is a business book that’s not really about business. It’s about life and what Russell calls Life Design, which is a great framing of how to be intentional about leading your life. 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, which I talk about in Startup CEO quite a bit in the nuts and bolts context of building your business.

Finally, Russell’s framework is easy to understand and full of concrete exercises you can to. Here are his five steps, but you’ll have to read the book to get the details:

• Ground stories with facts. This reminds me a lot of the principles we have taught team members over the years in our Action/Design (and related) trainings. First, start with absolute concrete facts that everyone will agree are facts.
• Establish your principles. This is brilliant. Your company has documented values or operating principles. Why don’t you?
• Harness energy from the environment. Figuring out what makes you tick, and what drains your energy, is so important.
• Get in and stay in your genius zone. Shouldn’t we all focus our time on the things we do best and love the most?
• Take action. How to put it together and make it all happen.

If you don’t get out in front of life, it will happen to you, and Russell’s framework is about how to make sure you are in the driver’s seat of your own life. Here’s to that.

Book Short:  Gladwell Lite

What the Dog Saw, And Other Adventures (book, Kindle) is Malcolm Gladwell’s latest book.  Unlike his three other books, which I quite enjoyed:

• The Tipping Point (about how trends and social movements start and spread)
• Blink (about how the mind makes judgments)
• Outliers: The Story of Success (about how talents are genetic, situational, and cultivated)

this was not a complete book, but rather a compendium of his New Yorker articles loosely grouped into three themes.

If you love Gladwell and don’t read The New Yorker, it’s not a bad read. He’s a fantastic writer, and his vignettes are interesting.  There are many “hmmm” moments as we learn why ketchup always tastes the same but mustard doesn’t; why Ron Popeil is a great salesman of kitchen gadgets; or why the inventor of the birth control pill thought the Pope would endorse it.  But it falls far short of his three books, which go deep into topics and leave a much more lasting impression/impact.

Book Short:  Blogging Alone?

I usually only blog about business books, but since I read Bowling Alone: The Collapse and Revival of American Community, by Robert Putnam, because of its connection to the topic of Internet community and social media, I’ll record some thoughts about and from it here.

It’s an interesting read, although a little long.  Putnam’s basic thesis is that America’s social capital — the things that have brought us physically and emotionally together as a country throughout much of the 20th century such as church, voting, and participation in civic organizations like the PTA or the Elks Club — are all severely on the decline.  The reasons in Putnam’s view are television (you knew all those re-runs of The Brady Bunch would eventually catch up to you), suburban sprawl, two-career families, and “generational values,” which is Putnam’s way of saying things like people in their 60s all read newspapers more than people in their 50s, who all read newspapers more than people in their 40s, etc.  He believes the decline is leading to things like worse schools, less safe neighborhoods, and poorer health.

The book does a good job laying out the decline in social capital with some really interesting and somewhat stunning numbers, but the book’s biggest shortcoming is that Putnam doesn’t do the work to determine causation.  I buy that there’s a correlation between less voting and less safe neighborhoods, for example, but the book doesn’t convince me that A caused B as opposed to B causing A, or C causing both A and B.  What I really wanted at the end of the book was for Putnam to go mano-a-mano with the Freakonomics guy for a couple hours.  Preferably in those big fake sumo suits.

The book was published in 2000, so probably written from 1997-1999, and therefore its treatment of the Internet was a little dated — so I found myself wanting more on that topic since so much of the social media revolution on the Internet is post-2004.  His basic view of the Internet is that it is in fact a bright spot in the decline of community, but that it’s changing the nature of communities.  Now instead of chatting with whoever is bowling in the next lane over at the Tuesday night bowling league on Main Street, we are in an online discussion group with other people who own 1973 BMW 2002 series cars, preferably the turbo-charged ones.  So the micro-communities of the Internet circa 2000 are more egalitarian (“on the Internet, no one knows you’re a dog”), but more narrow as well around interests and values.

What has social media done to Putnam’s theories in the last seven or eight years?  How have things like blogging, MySpace, LinkedIn, YouTube, and Photobucket changed our concept of community in America or in the world at large?  I welcome your comments on this and will write more about it in the future.

Book Short:  Blink Part II

Years ago I wrote a post about Malcolm Gladwell’s excellent book, Blink (post, buy).  While my post has lots of specifics in it for entrepreneurs, for VCs, and for marketers, my quick summary was this:

Where The Tipping Point theorizes about how humans relate to each other and how fads start and flourish in our society, Blink theorizes about how humans make decisions and about the interplay between the subconscious, learned expertise, and real-time inputs.  But Gladwell does more than theorize — he has plenty of real world examples which seem quite plausible, and he peppers the book with evidence from some (though hardly a complete coverage of relevant) scientific and quasi-scientific studies.

I recently finished another book, Thinking Fast, and Slow, by Daniel Kahneman, which was very similar.  I’d call it the academic version of Blink, or that Blink is the journalistic version of it.  Kahneman breaks down our ability to think and process information into what he calls System 1 (quick and intuitive) and System 2 (slower, rational and logical).  As he puts it:

In summary, most of what you (your System 2) think and do originates in your System 1, but System 2 takes over when things get difficult, and it normally has the last word.

The book is rich in examples, and while it’s a bit long and sometimes slow going, it is an excellent read if you want to learn more about how the brain works.  The work applications are many – we do a lot of work at Return Path on understanding and avoiding Unconscious Bias at work – and this book gave me a bunch of good ideas around that.  It’s clear that it’s impossible to become a true master of your intuition vs. logic, but you can design some systems, or at least insert some checks and balances into other systems, to blunt the impact of faulty intuition or lazy logic.  The book also has an overwhelming number of labels it applies to common situations – great, but hard to keep them all straight (the priming effect, anchors, endowment effect, etc.).

Perhaps the most interesting thing for me to ponder as an entrepreneur, though, was the section on Loss Aversion (another great label).  It turns out we humans are motivated more by fear of loss than by the prospect of gain.  A poignant example in the book is that professional golfers make a higher percentage of putts (I forget the actual number, but a real one, like 3-5%) for par than for birdie, when the putts are like-for-like in terms of distance and difficulty.  Saving par is more of a motivator than being under par.  The application for work is interesting.  As companies get larger, it can be difficult for founders and management teams to maintain the same level of bold risk-taking they did as smaller organizations.  Having something to lose is harder than having nothing to lose.  And yet, as they say, fortune favors the bold.  Growth stage companies need to figure out how to institutionalize risk taking and experimentation, including putting enough resources into those activities that will generate future growth, rather than simply protecting what’s already running.  (Of course, what’s already running needs investment, too.)

Thanks to my colleagues Dragana and Richard for recommending this book, and to Jamie for facilitating our office book club around it this month!

Book Short – Blink part III – Undo?

I just finished reading Michael Lewis’s The Undoing Project: A Friendship That Changed Our Minds, and honestly, I wish I could hit Life’s Undo button and reclaim those hours.  I love Michael Lewis, and he’s one of those authors where if he writes it, I will read it.  But this one wasn’t really worth it for me.

Having said that, I think if you haven’t already read both Malcolm Gladwell’s Blink (review, buy) and Daniel Kahneman’s Thinking, Fast and Slow (review, buy), then it might be worth it.  But having read those two books, The Undoing Project had too much overlap and not enough “underlap” (to quote my friend Tom Bartel) – that is, not enough new stuff of substance for me.  The book mostly went into the personal relationship between two academic thinkers, Daniel Kahneman and Amos Tversky.  It also touched on some of the highlights of their work, which, while coming out of the field of psychology, won them a Nobel prize in Economics for illuminating some of the underlying mechanics of how we make decisions.

The two most interesting pieces of their work to me, which are related in the book, are:

First, that human decision-making is incredibly nuanced and complex, and that at least 25% of the time, the transitive property doesn’t apply.  For example, I may prefer coffee to tea, and I may prefer tea to hot chocolate, but that doesn’t necessarily mean I prefer coffee to hot chocolate.

From the book, “When faced with complex multidimensional alternatives, such as job offers, gambles or [political] candidates, it is extremely difficult to utilize properly all the available information.” It wasn’t that people actually preferred A to B and B to C and then turned around and preferred C to A. It was that it was sometimes very hard to understand the differences. Amos didn’t think that the real world was as likely to fool people into contradicting themselves as were the experiments he had designed.  And the choice created its own context: Different features might assume greater prominence in the mind when the coffee was being compared to tea (caffeine) than when it was being compared to hot chocolate (sugar). And what was true of drinks might also be true of people, and ideas, and emotions. The idea was interesting: When people make decisions, they are also making judgments about similarity, between some object in the real world and what they ideally want. They make these judgments by, in effect, counting up the features they notice. And as the noticeability of features can be manipulated by the way they are highlighted, the sense of how similar two things are might also be manipulated.”

Second, what Kahneman and Tversky called Prospect Theory, which is basically that humans are more motivated by the fear of loss as opposed to the greed of gain.  I’ve written about the “Fear/Greed Continuum” of my former boss from many years ago before.  I’m not sure he knew about Kahneman and Tversky’s work when he came up with that construct, and I certainly didn’t know about it when I first blogged about it years ago.  Do this experiment – ask someone both of these questions:  Would you rather be handed $500 or have a 50% chance of winning $1,000 and a 50% of getting nothing?  Then, Would you rather hand me $500 or have a 50% chance of owing me $1,000 and a 50% chance of owing me nothing?  Most of the time, the answers are not the same.

For fun, I tried this out on my kids and re-proved Prospect Theory, just in case anyone was worried about it.

Anyway, bottom line on this book – read it if you haven’t ready those other two books, skip it if you have, maybe skim it if you’ve read one of them!

Book Short: Smaller is the New Small

Last month, it was Microtrends. This month, it’s MIT Professor Ted Sargent’s The Dance of Molecules: How Nanotechnology is Changing Our Lives. It seems like all the interesting things in life are just getting smaller and smaller. (Note to self: lose some weight.)

Sargent’s book is geeky but well-written. He dives into a couple dozen examples across many fields and disciplines of how nanotechnology holds extraordinary promise for solving some of mankind’s toughest scientific challenges — while creating a few new ethical and economic ones.

The science is for the most part beyond me, but the practical applications are fascinating:

– making solar power the sole source of global energy needs a possibility

– detecting cancer at the level of a single cancer cell rather than waiting to discover a grape-sized tumor; curing that cancer through embedded “pharmacy on a chip” drugs that release the right drugs over long periods of time locally at the spot of the disease

– figuring out how to keep proving the ever-more-challenging Moore’s law when only 4 years from now, parts of a transistor will need to be only 5 atoms across

– curing blindness with wireless retinal implants

Once every year or so, I read a book that makes me sad I didn’t go into engineering or science. The Dance of Molecules is that kind of book.

Book Short: How, Now

Every once in a while, I read a book that has me jump up and down saying “Yes! That’s so right!” How: Why How We Do Anything Means Everything in Business (and in Life), by Dov Seidman, was one of those books.  But beyond just agreeing with the things Seidman says, the book had some really valuable examples and two killer frameworks, one around culture, and one around leadership.

It’s a book about the way the world we now live in — a world of transparency and hyper-connectedness — is no longer about WHAT you do, but HOW you do it. It’s about how you can have a great brand and great advertising, but if your customers find out via a blog and YouTube clip that you run a low quality sweatshop in Malaysia, you are toast. It’s about you can…not outwork the competition, not outsmart the competition, but how you can out-behave the competition.

The book, which talks about principles like mutual gain, and thriving on the collaborative, reminds me a lot of a basic tenet of negotiation I learned years ago at the Harvard Program on Negotiation about finding a “third way” beyond a “me vs. you” negotiation by expanding the pie so both parties get more out of a deal.

Here are a few snippets from the book to inspire a purchase:

– How encouraging doctors to say “I’m sorry” radically reduces lawsuits

– How “micro-inequities” can subtly leech productivity from an organization

– How the majority of workers expect from their workplaces: equity, achievement, camaraderie

– How companies whose employees understand and embrace their mission, goals, and values see a 29% greater return than companies whose employees don’t

– How reputation is the new competitive advantage

– How people will do the right thing because in self-governing cultures, not doing the right thing no longer betrays just the company; it betrays individuals’ own values

– How increasing self-governance means moving values to the center of your efforts and making it clear — in how you reward, celebrate, communicate, and pursue — that those values form the guiding spirit of the enterprise

What type of organization do you run? One based on Anarchy & Lawlessness, one based on Blind Obedience, one based on Informed Acquiescence, or one of Values-Based Self-Governance? (Hint, it’s most likely the third category.) Read the book to find out more.

Book Short:  Deep Dive on Customer Development

I continue to be on a tear reading books about startups as I finish and get ready for the publication of Startup CEO (now available for pre-ordering at Amazon).   This week’s selection was The Startup Owners Manual:  A Step-by-Step Guide for Building a Great Company, by Steve Blank and Bon Dorf.  This book is a significantly more detailed version of Blank’s first book, The Four Steps to the Epiphany, which was a revolutionary book a few years ago that helped spawn the Lean Startup movement.

And when I say significantly, I mean it!  The Startup Owners Manual is 600 pages of really detailed how-to around the first two steps of Blank’s four steps, Customer Discovery and Customer Validation.  It doesn’t get into the last two steps at all, Customer Creation and Company Building.  It has a lot of overlap with Ash Maurya’s Running Lean (post, book), although it’s significantly more detailed.  And essentially, especially around the topic of “Company Building,” my book starts where this one stops.

One of Blank’s great lines in the book is that a “A startup is a temporary organization in search of a scalable, repeatable, profitable business model.”  That frames the whole Lean Startup movement really, really well.  The whole concept of Customer Discovery and Validation, of testing hypotheses, is critical to getting product-marketing fit right in a capital-efficient manner.  If I were starting Return Path today, we’d be using these methods from the get-go.

But Lean principles are wholly compatible with larger companies, as well, and in fact we use all of these principles in our product development organization today.  We adapt them for our size and scale and the fact that often we are selling either new or enhanced versions of existing product into existing customers, but our product teams have all embraced the Lean principles and the vocabulary around them, and our goal is that we should never bring a product to market that isn’t already being bought.

I love me a good framework. And Geoffrey Moore is the kind of good product/marketing frameworks for technology companies. Moore’s Zone to Win: Organizing to Compete in an Age of Disruption is a must-read for anyone managing a larger technology organization (start reading it when you get to 200-250 people – it’s never too early to worry about disruption). More important, it’s really a companion book or coda to Escape Velocity: Free Your Company’s Future from the Pull of the Past, so if you haven’t read that one, start there and read both sequentially. Zone to Win is quite short and punchy, and it doesn’t disappoint.

I can’t believe is that I never blogged about Escape Velocity before since it was a very influential book in how we managed a bunch of things at Return Path in the later years when we got larger and were more in “disrupt or be disrupted” mode. I’ll start with the essence of that book before I move onto Zone to Win. Escape Velocity‘s principal framework is to divide the different product lines/lines of business you have into three planning horizons:

• Horizon 1 (H1): Current businesses that should be profitable and sustainable
• Horizon 3 (H3): Nascent R&D efforts with the potential to be disruptors or game changers
• Horizon 2 (H2): The bridge between H1 and H3 where an R&D effort that is taking off is scaled and hopefully achieves the eponymous Escape Velocity

The essence of the book is to talk about how larger companies become completely slavish to H1 businesses, their cash cows, and struggle to escape from their pull, whether that’s internal resource allocation or customer-driven demands. Failure to innovate properly beyond H1 businesses is why companies die. But the rest of the book is a lot less memorable, and it doesn’t quite prompt you into action.

That’s where Zone to Win comes in, and it helps me understand where we really got a couple things really wrong at Return Path (as an aside, Moore once met my Return Path cofounder George at a conference, and when George described our business to him, he said “Ah, a blue collar business. Those can work, too.” I think I understand what he meant by that, although it doesn’t sound like a compliment!)

In Zone to Win, Moore shows you how to put the three Horizons into action by creating an overlay framework to managing your company to help optimize all three zones simultaneously. The four zones are:

The key takeaways for me from this framework as well as the notes of where we got things wrong at Return Path, even while acknowledging that we had to play across H1, H2, and H3 simultaneously, were:

• Performance Zone: Managing your main H1 business in a way that drives growth and customer success for the long haul
• Productivity Zone: Managing your main H1 business for optimal profitability and scalability
• Incubation Zone: Starting new H3 businesses and hoping they work
• Transformation Zone: Getting your H3 business through H2 and into H1 to the point where it’s at least 10% of your overall revenue

What we got right at Return Path was first recognizing that we needed to incubate new businesses as the growth in our core business started to slow down, as well as recognizing that we needed to step up our game in managing the core business for performance. So, Moore would say something like “congratulations, you drew up the correct strategy.” But we fell down on implementation for reasons in three of the four zones. Our problem with the Performance Zone is that we discovered the three horizon model too late — there were several years where we were running R&D experiments in the middle of the core business, which created chaos. By the time we got religion around it, we were constantly playing catch up redesigning our management processes — like the teenager still wearing his kid clothes looking awkward and misfit. In the Productivity Zone, we did invest in productivity, but we weren’t aggressive enough about insisting on End of Life for some programs or products, and and we were bogged down by a convoluted legacy implementation of our CRM system that we never wholesale fixed. But the biggest problem we ran into was in the Transformation Zone, where we tried to jam two new businesses through that zone at the same time instead of focusing all our energies on one. I bet we could have pulled off even more of a transformational success with our security business (the one further along) if we hadn’t also been trying to get our consumer insights business through H2 at the same time. At least Moore notes that’s the hardest zone to get right, so I don’t feel quite so dumb.

There were probably other exogenous factors that caused us to fall down on implementation, too, but I think this had a lot to do with it. And don’t get me wrong, Return Path was a success in the end. It just could have been more successful if we had caught this book and adhered rigorously sooner. It was even published in time — somehow we just missed it. We were lured by customer traction and market pull into thinking we could do both. And it’s certainly possible that we were advised against this by one or more of our board members and plowed ahead anyway.

Moore is a masterful writer. If you haven’t read Crossing the Chasm or Inside the Tornado, for example, if you’re a GenZ founder and you think “wow those books came out before I was born, they can’t be relevant,” you should start by reading them. They’re still 100% applicable today, and Moore’s subsequent editions have updated some of the case studies, even if not totally contemporary — and these are worth reading even as a raw startup (in fact, especially as a raw startup). But once you finish those and your business gets larger, go straight into Escape Velocity and be sure to add on Zone to Win.

I’ve written a bunch on this blog and in Startup CEO, about Agile Development and the Lean Canvas and Lean Startups in general (see a really old post on Agile Development from 10 years ago when we first adopted it here, and one on Agile Marketing here).  The basic premise of all of this is that there is an old way to build software products and businesses, and a new lighter way loosely based on Toyota’s lean manufacturing principles.  The old way is HEAVY — you spec out a product and build it and hope you got it right; you write a big business plan and start raising money and executing on it and hope your assumptions are correct.  The new way is LIGHTER — you co-create product with customers and develop a Minimum Viable Product so that by the time it’s ready to sell, some customers are already buying it; you create a business plan that is all about systematically testing the underlying assumptions first, then raising money and charging forward after you know what you’re dealing with.

As readers of this blog know, Return Path is a software/services company that cares about building a robust business, and we also have a lot of passion around building our organization and culture.  We’ve always been fairly progressive with our People practices and programs, and we’re also always trying to innovate to make those things more impactful, easier, and more fun.  And that brings us to the subject of this post.

Over the last 2 years, we have been working to make teams more effective (creatively, we called this work “Effective Teams”); we loosely used Patrick Lencioni’s 5 Dysfunctions of a Team as the framing for the work we do with teams.  We ensure they develop strong, trusting relationships, have the skills and courage to have healthy conflict, which means they can commit to the decisions they make; they then hold each other accountable and ultimately get better results.   In addition to regular team development activities, our teams now give each other regular feedback including team-based peer-to-peer feedback through a facilitated quarterly session.   We saw improvements in team development which were verified by an increase of 13% of positive results in team effectiveness surveys.

We are now working to ensure that teams are working in a more agile way, and that their stakeholders are involved in the creation and evaluation of team goals.   Through our “Agile Everywhere” initiative, our Effective Teams work is expanding to help teams develop more agile operating systems.  By June 30, teams will be using some of the agile methodologies to:

break work down into smaller pieces

check in frequently on progress

share feedback among team members and stakeholders

tune practices based on feedback

report results publicly and

establish a predictable operating system.

As with most of our People practices, we modeled this on the Executive Committee, and we’ve instituted  things like Daily Stand-ups and Trello Boards for a pretty disparate set of teams.  We’ve found some practices useful, and we’ve adapted some practices to meet our needs.  We are now in process of piloting these practices with 15 teams throughout the company.  Stay tuned!