I keep expecting one of his books to be repetitive or boring, but Patrick Lencioni’s The Five Dysfunctions of a Team held my interest all the way through, as did his others. It builds nicely on the last one I read, Death by Meeting (post, link).
I’d say that over the 9 1/2 years we’ve been in business at Return Path, we’ve systematically improved the quality of our management team. Sometimes that’s because we’ve added or changed people, but mostly it’s because we’ve been deliberate about improving the way in which we work together. This particular book has a nice framework for spotting troubles on a team, and it both reassured me that we have done a nice job stamping out at least three of the dysfunctions in the model and fired me up that we still have some work to do to completely stamp out the final two (we’ve identified them and made progress, but we’re not quite there yet.
The dysfunctions make much more sense in context, but they are (in descending order of importance):
Absence of trust
Fear of conflict (everyone plays politically nice)
Lack of commitment (decisions don’t stick)
Avoidance of accountability
Inattention to results (individual ego vs. team success)
For those who are wondering, the two we’re still working on at the exec team level here are conflict and commitment. And the two are related. If you don’t produce engaged discussion about an issue and allow everyone to air their opinions, they will invariably be less bought into a decision (especially one they don’t agree with). But we’re getting there and will continue to work aggressively on it until we’ve rooted it out.
There’s one other interesting takeaway from the book that’s not part of the framework directly, which is that an executive has to be first and foremost a member of his/her team of peers, not the head of his/her department. That’s how successful teams get built. AND (this is key) this must trickle down in the organization as well. Everyone who manages a team of group heads or managers needs to make those people function well as a team first, then as managers of their own groups second.
At any rate, another quick gem of a book. I’m kind of sorry there’s only one left in the series.
The Three Signs of a Miserable Job (post, link), The Five Temptations of a CEO (post, link), and The Four Obsessions of an Extraordinary Executive (post, link) are all related around the topic of management.
Death by Meeting (post, link), The Five Dysfunctions of a Team (post, link), and Silos, Politics and Turf Wars, on the other hand, are all related around the topic of leading a team and healthy team dynamics. This latest book, which is the last of his six books for me, rounds out this topic nicely, in a fun “novel” format as is the case with his other books.
The book hammers home the theme of an executive team needing to first be a team and then second be a collection of group heads as a means of breaking down barriers that exist inside organizations. It also lays out a framework for creating high-level alignment inside a team. The framework may or may not be perfect — we are using a different one at Return Path (the Balanced Scorecard) that accomplishes most of the same things — but for those companies who don’t have one, it’s as good as any.
The most compelling point in the book, though is the point that teams often make the most progress, change the most, and do their best work when their backs are up against a wall. And the point Lencioni makes here is — “why wait for a crisis?”
At any rate, another good, quick book, and absolutely worth reading along with the others, particularly along with the other two closely related ones. I’m definitely sorry to be done with the series. We may try the “field guide” companion to The Five Dysfunctions and see how the practical exercises work out.
Being on the same page with your team, or your whole company for that matter, is a key to success in business. The Four Obsessions of an Extraordinary Executive, by Patrick Lencioni, espouses this notion and boils down the role of the CEO to four points:
Build and maintain a cohesive leadership team
Create organizational clarity
Overcommunicate organizational clarity
Reinforce organizational clarity through human systems
Those four points sound as boring as bread, but the book is anything but. The book’s style is easy and breezy — business fiction. One of the most poignant moments for me was when the book’s “other CEO” (the one that doesn’t “get it”) reflects that he “didn’t go into business to referee executive team meetings and delivery employee orientation…he loved strategy and competition.” Being a CEO is a dynamic job that changes tremendously as the organization grows. This book is a great handbook for anyone transitioning out of the startup phase, or for anyone managing a larger organization.
I haven’t read the author’s other books (this is one in a series), but I will soon!
I liked this book a lot. First, the beginning section is a bit of a recap of his Five Dysfunctions of a Team which I think was his best book. And the ending section is a recap of his Death by Meeting, another really good one. The middle sections of the book are just a great reminder of the basic building blocks of creating and communicating strategy and values – about driving alignment.
But the premise, as the subtitle indicates, is that maintaining organizational health is the most important thing you can do as a leader. I tell our team at Return Path all the time that our culture is a competitive advantage in many ways, some quantifiable, and others a little less tangible.
A telling point in the book is when Lencioni is relaying a conversation he had with the CEO of a client company who does run a healthy organization – he asked, “Why in the world don’t your competitors do any of this?” And the client responded, “You know, I honestly believe they think it’s beneath them.” Lencioni goes on to say, “In spite of its undeniable power, so many leaders struggle to embrace organizational health because they quietly believe they are too sophisticated, too busy, or too analytical to bother with it.” And there you have it. More examples of why “the soft stuff” is mission critical.
Lencioni’s “Recipe for Organizational Health” (the outline of the book):
– Build a Cohesive Leadership Team
– Create Clarity
– Overcommunicate Clarity
– Reinforce Clarity
And his recipe for creating a tight set of “mission/vision/values” (the middle of the book):
1. Why do we exist?
2. How do we behave?
3. What do we do?
4. How will we succeed?
5. What is most important, right now?
6. Who must do what?
While there are lots of other good frameworks for doing all of this, Lencioni’s models and books are great, simple reminders of one of the CEO’s most important leadership functions. We’re recrafting our own mission and values statements at the moment at Return Path, and we’re doing it using this 6-Question framework instead of the classic “Mission/Vision/Values” framework popularized a few years back by Harvard Business Review.
The full book series roundup as far as OnlyOnce has gotten so far is:
A couple people who read Startup CEO: A Field Guide to Scaling Up Your Business asked me if I would publish a list of all the other business books I refer to over the course of the book. Here it is — I guess in some respects an all-time favorite list for me of business books.
Was anyone else as appalled as I am by the contents of Connie Loizos’s recent article, Coming out of COVID, investors lose their taste for board meetings? The stories and quotes in the article about VCs reducing their interest and participation in Board meetings, not showing up, sending the junior associate to cover, etc. are eye opening and alarming if widespread.
The reasons cited in the article are logical—overextended VCs, Zoom fatigue, and newbie directors. Connie’s note that “privately, VCs admit they don’t add a lot of value to boards” is pretty funny to read as a CEO who has heard a ton of VCs talk about how much value they add to boards (although the good ones DO add a lot of value!).
For the most part, everything about the substance of this article just made me angry.
Disengaged or dysfunctional boards aren’t just bad for CEOs and LPs; they’re bad for everyone. If the world has truly become a place where the board meeting is nothing more than a distraction for CEOs, and investors think it’s a tax they can’t afford, then it’s time to hit the reset button on boards and board meetings.
Here are four things that need to happen in this reset:
VCs need to do their job well or stop doing it. The argument that investors did too many deals in the pandemic so now they don’t have any time is a particularly silly one, since the pandemic reduced the amount of time VCs needed to spend on individual board meetings as well. I used to have four board meetings each year with directors who were traveling for the meetings, having dinners, spending time with the team and sitting in on committee meetings.
Today, boards are lucky to have one in-person meeting a year (more on that later). And as everything else takes less time, and there’s little transit, any given VC should have doubled the time they spend on board meetings.
Serving on a board post-investment is a central part of the VC role. They have obligations to the founders they back and to the LPs they represent. The entire role is “find deals, execute deals, manage the portfolio.”
If they no longer have time for the third job, they need to admit that to both founders and LPs before stepping down. If a VC can’t be bothered to focus on minding their investments and adding value, they should work with the company to find their replacement.
CEOs need to take their job as leader of the board seriously. Would a good CEO just throw their hands up if they found management team meetings boring or a waste of time? No. They’d fix the structure of the team or meetings. If not, they shouldn’t be the CEO.
It’s no different with boards. Whether or not the CEO is the board chair, they’re the leader of the organization. So, one of the few “must do” items in their job description is leading the board. The board is part of the CEO’s team, just like the management team.
CEOs get to call the meetings, run the meetings, and insist on attendance. The CEO’s obligation is to make it easy and meaningful for everyone so the board isn’t a tax but rather a secret weapon for the company’s success. As my long-time independent director Scott Weiss used to tell me, boards consume whatever you put in front of them. Garbage in, garbage out. That means paying careful attention to the board materials, to meeting etiquette, and everything in between.
Here’s one tip on making Board prep more efficient: work your Operating System and your Board Book formats so you do one set of reporting for the company and management team that is 95% reusable without any changes for your board.
The format for Board meetings needs to evolve. Board meetings need to evolve in our world of hybrid work just as office work needs to evolve. The format that works for in-person can’t just “lift and shift” to Zoom as is, indefinitely.
Here’s how I’m steering my board:
I insist on one or two “old school” meetings per year, meaning in-person attendance required, half a day long, and including a meal and even an activity. If I’m only going to see my directors together infrequently, I make it mandatory, but I also make it worthwhile and fun.
Remote meetings that happen between the in-person meetings are becoming shorter and tighter. I still send out a lot reading material beforehand, but I make sure to keep the focus on a fixed number of major topics to keep the discussion engaging.
We need a new set of expectations around Zoom meeting etiquette for long meetings. It’s okay to ask people to close their email, browser, and Slack before the meeting starts. If a meeting is more than two hours long, a 15 minute break in the middle is important. Use breakout rooms to mix up topic discussions and working sessions.
I am trying a new meeting format to maximize director conversation and team development. I start every meeting with a director-only session for half an hour that’s not exactly an Executive Session but is more fun and social—usually including a nonwork discussion topic, as if we were sitting around the dinner table having a cocktail. That gets the conversational juices flowing. Then when my team and observers join the meeting, I ask those people to turn their video off, and I ask directors to adjust their Zoom setting to “hide participants not on video” to keep the number of Zoom squares down to the bare minimum. Any time a team member or observer wants to engage in a particular topic, they turn their video on. Then we follow the meeting with Executive Session and Closed Session and a single-director debrief with me. That is a lot of moving pieces to manage, I find that but doing so keeps the meeting fresh and well paced.
Finally, I’m following Fred Wilson’s advice and running a very short survey post-meeting to ask directors basic questions so they can summarize their thinking for me and the team: What are we doing well? What do we need more work on? And did the meeting meet your expectations?
Companies need to Follow the Rule of 1s
The secret to engaged and diverse boards is to mix up their membership more than most companies do. Our Board Benchmark study at Bolster indicates that the vast majority of private company boards have no independent directors at all—only founders and investors—and every year, the vast majority of the “open independent seats” specified in those companies’ charters go unfilled.
It’s hard work hiring a new independent board member, and it rarely rises to the top of the CEO’s priority list. But the more independent the board is, and the more diverse the board is in every way (in terms of demographics as well as experience and background), the more robust the conversations around the table become, and the more valuable the board is to the CEO.
My Rule of 1s for building highly effective boards is simple:
Add independent directors to your board on Day 1
Try to limit your Board to 1 founder/team member
Then, for every 1 investor on your board,
Add 1 independent director
A great board is one of a company’s greatest assets. A weak board can kill a company. A mediocre board is just a waste of time. There’s no question that running an effective board, or serving as an effective director, takes serious time and energy and diligence. But that’s not a reason not to try.
As we wrote in Bolster’s Founding Manifesto, one of the reasons we started Bolster was to create a new way; a faster, easier, and more cost-effective way, for startup and scaleup CEOs to grow their boards of directors and make them more diverse.
There’s a lot of research out there that the more independent a board is, the better it performs for companies — and that there’s a high degree of correlation between more independent boards and higher performing companies as well. There’s also a lot of research out there that shows that teams which have diversity of gender and race/ethnicity perform better. And everyone who has ever been on a high-functioning board of directors knows that a board is a team.
These facts are well known, yet it is still the case that most private company boards are overwhelmingly made up of founders and investors who are still largely white and male. I believe that the lack of independence and diversity on boards is a big miss for the whole startup ecosystem, and it’s a part of the startup game that we at Bolster want to help change.
Startup boards are tricky things. One of the very unique aspects of a CEO’s job that sets it apart from other executive positions is building and leading a board of directors. But most startup CEOs have either little or no experience building and leading a board, so that part of the job tends to default to a “because that’s the way I assume it’s always been done” kind of task. Of course, if you’re not intentional about building and managing a board, you’re likely to get lousy results.
Building, shaping, and leading a world class board is one of the single most important things startup CEOs can do to help their businesses thrive and become industry leaders. It’s on par with building and leading an executive team. I’ve seen amazing companies held back by weak and ineffective boards and investor syndicates, and I’ve seen so-so companies succeed because the strategic advice, experience, and accountability coming out of the board room drives the management team in extraordinary ways.
So how is Bolster helping startup CEOs change the game with respect to Boards? We are doing three things.
First, as you know, what gets measured gets managed. Our first-of-its-kind Board Benchmark application will soon produce an industry standard set of data around private company boards. You can’t find data on private company boards but we’ll soon have important data like size, composition (independents/management/investors), independent director compensation and diversity (gender/race-ethnicity/age). This will help answer questions that I know I have had many times over the years as a CEO such as
How big should my board be at this stage?
How many independent directors should I have?
What is the right profile of an independent director?
How many options should I give a board member?
Starting next week, we’re opening up our Board Benchmark application to any company who creates a free Bolster account. It will tell us a lot about the baseline across the ecosystem, and it will answer a lot of questions startup and scaleup CEOs have but can’t get answers to. Although this is an ongoing real-time benchmark tool, I’ll post some results here when we have enough critical mass to start reporting out.
Second, Bolster is in the talent business, and helping match VC-backed companies with a strong diverse slate of board candidates who are well-matched with their company is at the core of our business. We are already working on many searches for independent board members, and we’ll only be doing more of them as our client base and member base grow.
Finally, this blog post is the beginning of a whole series of posts about startup boards that we hope will demystify them a bit and help change the world’s thinking about how to grow them. Some of the material I will borrow from other blog posts I’ve written, or from the Board of Directors section of Startup CEO. Some will come from other influential VC and CEO bloggers and from Brad Feld and Mahendra Ramsinghani’s book Startup Boards.But much of the content will be new. And because Bolster is a two-sided marketplace, roughly half of the content will be aimed at startup CEOs and the other half at executives who are interested in serving on boards and aren’t sure how to get from where they are today into a board room. We’ll be sending out all the CEO posts as an eBook to CEOs who complete the Board Benchmark study, and all the Member posts as an eBook to Bolster members who fill out their Board profiles. I’ll post both of those eBooks here eventually as well.
For CEOs, the topics we will cover include
The purpose of a board
Size and composition on boards
Board evolution & turnover
Diversity in the boardroom and the importance of appointing first-time directors
What to look for in a director
How to recruit and interview directors
How to onboard directors, especially first time directors
How to compensate directors
How to build a director bench or Advisory Board
How to evaluate your board
For executives searching for a board role, the topics we will cover include
What startup corporate boards look like
How to prepare yourself to get on your first board
Should you serve on an advisory board?
How to interview for a Board role
What you need to know about board compensation
How to approach your first board meeting
How to think about corporate governance as a board member
How to be a great board member
How to give advice or difficult feedback as a board member
Making sure your voice is heard during a board meeting
How to know if you’re doing a good job as a board member
We believe that boards can make or break a company and we intend to chart a new course for startup boards. I look forward to sharing thoughts and data with you on that topic in the weeks to come.
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.
Getting Naked: A Business Fable About Shedding The Three Fears That Sabotage Client Loyalty (book, Kindle), is Patrick Lencion’s latest fable-on-the-go book, and it’s as good a read as all of his books (see list of the ones I’ve read and reviewed at the end of the post).
The book talks about the power of vulnerability as a character trait for those who provide service to clients in that they are rewarded with levels of client loyalty and intimacy. Besides cringing as I remembered my own personal experience as an overpaid and underqualified 21 year old analyst at how ridiculous some aspects of the management consulting industry are…the book really made me think. The challenge to the conventional wisdom of “never letting ‘em see you sweat” (we *think* vulnerability will hurt success, we *confuse* competence withego, etc.) is powerful. And although vulnerability is often uncomfortable, I believe Lencioni is 100% right – and more than he thinks.
First, the basic premise of the book is that consultants have three fears they need to overcome to achieve nirvana – those fears and the mitigation tactics are:
Fear of losing the business: mitigate by always consulting instead of selling, giving away the business, telling the kind truth, and directly addressing elephants in the room
Fear of being embarrassed: mitigate by asking dumb questions, making dumb suggestions, and celebrating your mistakes
Fear of feeling inferior: mitigate by taking a bullet for the client, making everything about the client, honoring the client’s work, and doing your share of the dirty work
But to my point about Lencioni being more right than he thinks…I’d like to extend the premise around vulnerability as a key to success beyond the world of consulting and client service into the world of leadership. Think about some of the language above applied to leading an organization or a team:
Telling the kind truth and directly addressing elephants in the room: If you’re not going to do this, who is? There is no place at the top of an organization or team for conflict avoidance
Asking dumb questions: How else do you learn what’s going on in your organization? How else can you get people talking instead of listening?
Making dumb suggestions: I’d refer to this more as “bringing an outside/higher level perspective to the dialog.” You never know when one of your seemingly dumb suggestions will connect the dots for your team in a way that they haven’t done yet on their own (e.g., the suggestions might not be so dumb after all)
Celebrating your mistakes: We’re all human. And as a leader, some of your people may build you up in their mind beyond what’s real and reasonable. Set a good example by noting when you’re wrong, noting your learnings, and not making the same mistake twice
Taking a bullet for your team, making everything about your team and honoring your team’s work: Management 101. Give credit out liberally. Take the blame for team failings.
Doing your share of the dirty work: An underreported quality of good leaders. Change the big heavy bottle on the water cooler. Wipe down the coffee machine. Order the pizza or push the beer cart around yourself. Again, we’re all human, leaders aren’t above doing their share to keep the community of the organization safe, fun, clean, well fed, etc.
There’s a really powerful message here. I hope this review at least scratches the surface of it.
The full book series roundup as far as OnlyOnce has gotten so far is:
I’ve written a few things about my Board of Directors over the years, some of which I note below. Part I of this series isn’t particularly useful, though there’s an entertaining link in it to a video of Fred that’s worth looking at if you know or follow him.
Today, we are happy to announce that we are adding a new independent director, Scott Petry, the founder of Postini and now a senior email product leader at Google (read the official press release [here]). Scott’s a fantastic addition to our already strong Board, and the process of recruiting and adding him has made me reflect a bit on my Board and its strengths and weaknesses, so I thought I’d share a couple of those thoughts here.
I think Return Path has cultivated a very high functioning Board over the years, and I feel very fortunate to have the group that we have. Here are the top five things I think make our Board special, in no particular order.
We have great individuals on the Board. Each of our individual Board members — Fred Wilson, Greg Sands, Scott Weiss, Scott Petry, and Brad Feld (now officially an observer), (in addition to me) — could anchor a super strong Board in his own right and have all served on multiple Boards of related companies. And not only do these guys know their stuff…they do their homework. They all come to every meeting very well prepared.
The individual Board members are different but have different experiences and personalities that complement each other nicely. Among the three VCs on the Board, two have operating experience, one as a founder and one in product management. Among the two industry CEOs, one has more of a business development focus, and the other has deep technical expertise. Some directors are excitable and a bit knee-jerk, others are more reflective; some are aggressive and others are more conservative; some have extremely colorful metaphors, others are a bit more steeped in traditional pattern recognition.
We have built a great team dynamic that encourages productive conflict. I assume a lot of rooms full of great directors of different types are so ego-laden that people just talk over each other. Our group, for whatever reason, doesn’t function that way. We are engaged and in each others’ faces during meetings, no one is afraid to voice an opinion, and we listen to each other. Some of this may be the way we spend time together outside of Board rooms, which I wrote about in The Social Aspects of Running a Board. Some is about just making sure to have fun, which I wrote about in The Good, The Board, and The Ugly (Part I, Part II, Part III), I talk about other aspects of running a good Board, including making sure to have fun – that post includes an entertaining picture of now-Twitter CEO Dick Costolo and a few of his friends from his FeedBurner days.
We are deliberate about connecting the Board and the Executive team, and the rest of the company. We encourage every director to have a direct relationship with every one of my direct reports. They connect both during and outside of meetings, and they have gotten to know each other well over the years. This is much more helpful to us than a more traditional “hourglass” structure where all connections go through the CEO.
We run great meetings. We send out a single, well-organized document several days before the meeting. Board members do their homework. We focus on current and future issues more than reporting on historical numbers, and we no longer do any presentations — it’s all discussion (I also wrote about a lot of this here in PowerPointLess).
Welcome to the Return Path family, Scott P – we are delighted to have you on board our Board!
(This post was requested by my long-time Board member Brad Feld and is also running concurrently on his blog today)
I’ve written a bunch of posts over the years about how I manage my Board at Return Path. And I think part of having awesome Board members is managing them well – giving transparent information, well organized, with enough lead time before a meeting; running great and engaging meetings; mixing social time with business time; and being a Board member yourself at some other organization so you see the other side of the equation. All those topics are covered in more detail in the following posts: Why I Love My Board, Part II, The Good, The Board, and The Ugly, and Powerpointless.
But by far the best way to make sure you have an awesome board is to start by having awesome Board members. I’ve had about 15 Board members over the years, some far better than others. Here are my top 5 things that make an awesome Board member, and my interview/vetting process for Board members.
Top 5 things that make an awesome Board member:
They are prepared and keep commitments. They show up to all meetings. They show up on time and don’t leave early. They do their homework. The are fully present and don’t do email during meetings
They speak their minds. They have no fear of bringing up an uncomfortable topic during a meeting, even if it impacts someone in the room. They do not come up to you after a meeting and tell you what they really think. I had a Board member once tell my entire management team that he thought I needed to be better at firing executives more quickly!
They build independent relationships. They get to know each other and see each other outside of your meetings. They get to know inviduals on your management team and talk to them on occasion as well. None of this communication goes through you
They are resource rich. I’ve had some directors who are one-trick or two-trick ponies with their advice. After their third or fourth meeting, they have nothing new to add. Board members should be able to pull from years of experience and adapt that experience to your situations on a flexible and dynamic basis
They are strategically engaged but operationally distant. This may vary by stage of company and the needs of your own team, but I find that even Board members who are talented operators have a hard time parachuting into any given situation and being super useful. Getting their operational help requires a lot of regular engagement on a specific issue or area. But they must be strategically engaged and understand the fundamental dynamics and drivers of your business – economics, competition, ecosystem, and the like
My interview/vetting process for Board members:
Take the process as seriously as you take building your executive team – both in terms of your time and in terms of how you think about the overall composition of the Board, not just a given Board member
Source broadly, get a lot of referrals from disparate sources, reach high
Interview many people, always face to face and usually multiple times for finalists. Also for finalists, have a few other Board members conduct interviews as well
Check references thoroughly and across a few different vectors
Have a finalist or two attend a Board meeting so you and they can examine the fit firsthand. Give the prospective Board member extra time to read materials and offer your time to answer questions before the meeting. You’ll get a good first-hand sense of a lot of the above Top 5 items this way
Have no fear of rejecting them. Even if you like them. Even if they are a stretch and someone you consider to be a business hero or mentor. Even after you’ve already put them on the Board (and yes, even if they’re a VC). This is your inner circle, and getting this group right is one of the most important things you can do for your company
I asked my exec team for their own take on what makes an awesome Board member. Here are some quick snippets from them where they didn’t overlap with mine (with only two inside jokes that I couldn’t resist putting up for the Board):
Ethical and high integrity in their own jobs and lives
Comes with an opinion
Thinking about what will happen next in the business and getting management to think ahead
Call out your blind spots
Remembering to thank you and calling out what’s right
Role modeling for your expectations of your own management team – Do your prep, show up, be fully engaged, be brilliant/transparent/critical/constructive and creative. Then get out of our way
Offer tough love…Unfettered, constructive guidance – not just what we want to hear
Pattern matching: they have an ability to map a situation we have to a problem/solution at other companies that they’ve been involved in – we learn from their experience…but ability and willingness to do more than just pattern matching. To really get into the essence of the issues and help give strategic guidance and suggestions
Ability to down 2 Shake Shack milkshakes in one sitting
Colorful and unique metaphors
Disclaimer – I run a private company. While I’m sure a lot of these things are true for other types of organizations (public companies, non-profits, associations, etc.), the answers may vary. And even within the realm of private companies, you need to have a Board that fits your style as a CEO and your company’s culture. That said, the formula above has worked well for me, and if nothing else, is somewhat time tested at this point!
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