Startup CEO (OnlyOnce – the book!), Part III – Pre-Order Now

My book, Startup CEO:  A Field Guide to Scaling Up Your Business, is now available for pre-order on Amazon in multiple formats (Print, Kindle), which is an exciting milestone in this project!  The book is due out right after Labor Day, but Brad Feld tells me that the more pre-orders I have, the better.  Please pardon the self-promotion, but click away if you’re interested!

Here are a few quick thoughts about the book, though I’ll post more about it and the process at some point:

• I’ll be using the hashtag #startupceo more now to encourage discussion of topics related to startup CEOs – please join me!
• The book has been described by a few CEOs who read it and commented early for me along the lines of “The Lean Startup movement is great, but this book starts where most of those books end and takes you through the ‘so you have a product that works in-market – now what?’ questions”
• The book is part of the Startup Revolution series that Brad has been working on for a couple years now, including Do More (Even) Faster, Venture Deals, Startup Communities, and Startup Life (with two more to come, Startup Boards and Startup Metrics)
• Writing a book is a LOT harder than I expected!

At this point, the best thing I can do to encourage you to read/buy is to share the full and final table of contents with you, sections/chapters/headings.  When I get closer in, I may publish some excerpts of new content here on Only Once.  Here’s the outline:

Part I: Storytelling

• Chapter 1: Dream the Possible Dream…Entrepreneurship and Creativity, “A Faster Horse,” Vetting Ideas
• Chapter 2: Defining and Testing the Story…Start Out By Admitting You’re Wrong, A Lean Business Plan Template, Problem, Solution, Key Metrics, Unique Value Proposition and Unfair Advantages, Channels, Customer Segments, Cost Structure and Revenue Streams
• Chapter 3: Telling the Story to Your Investors…The Business Plan is Dead. Long Live the Business Plan, The Investor Presentation, The Elevator Pitch, The Size of the Opportunity, Your Competitive Advantage, Current Status and Roadmap from Today, The Strength of Your Team, Summary Financials, Investor Presentations for Larger Startups
• Chapter 4: Telling the Story to Your Team…Defining Your Mission, Vision and Values, The Top-down Approach, The Bottom-Up Approach, The Hybrid Approach, Design a Lofty Mission Statement
• Chapter 5: Revising the Story…Workshopping, Knowing When It’s Time to Make a Change, Corporate Pivots: Telling the Story Differently, Consolidating, Diversifying, Focusing, Business Pivots: Telling a Different Story
• Chapter 6: Bringing the Story to Life…Building Your Company Purposefully, The Critical Elements of Company-Building, Articulating Purpose:  The Moral of the Story, You Can Be a Force for Helping Others—Even If Indirectly

Part II: Building the Company’s Human Capital

• Chapter 7: Fielding a Great Team…From Protozoa to Pancreas, The Best and the Brightest, What About HR?, What About Sales & Marketing?, Scaling Your Team Over Time
• Chapter 8: The CEO as Functional Supervisor…Rules for General Managers
• Chapter 9: Crafting Your Company’s Culture…, Introducing Fig Wasp #879, Six Legs and a Pair of Wings, Let People Be People, Build an Environment of Trust
• Chapter 10: The Hiring Challenge…Unique Challenges for Startups, Recruiting Outstanding Talent, Staying “In-Market”, Recruitment Tools, The Interview: Filtering Potential Candidates, Two Ears One Mouth, Who Should You Interview?, Onboarding: The First 90 Days
• Chapter 11: Every Day in Every Way, We Get a Little Better…The Feedback Matrix, 1:1 Check-ins, “Hallway” Feedback, Performance Reviews, The 360, Soliciting Feedback on Your Own Performance, Crafting and Meeting Development Plans      
• Chapter 12: Compensation…General Guidelines for Determining Compensation, The Three Elements of Startup Compensation, Base Pay, Incentive Pay, Equity              
• Chapter 13: Promoting                …Recruiting from Within, Applying the “Peter Principle” to Management, Scaling Horizontally, Promoting Responsibilities Rather than Swapping Titles               
• Chapter 14: Rewarding: “It’s the Little Things” That Matter…It Never Goes Without Saying, Building a Culture of Appreciation
• Chapter 15: Managing Remote Offices and Employees…Brick and Mortar Values in a Virtual World, Best Practices for Managing Remote Employees
• Chapter 16: Firing: When It’s Not Working…No One Should Ever Be Surprised to Be Fired, Termination and the Limits of Transparency, Layoffs

Part III: Execution

• Chapter 17: Creating a Company Operating System…Creating Company Rhythms, A Marathon? Or a Sprint?
• Chapter 18: Creating Your Operating Plan and Setting Goals…Turning Strategic Plans into Operating Plans, Financial Planning, Bringing Your Team into Alignment with Your Plans, Guidelines for Setting Goals
• Chapter 19: Making Sure There’s Enough Money in the Bank…Scaling Your Financial Instincts, Boiling the Frog, To Grow or to Profit? That Is the Question, First Perfect the Model, Choosing Growth, Choosing Profits, The Third Way
• Chapter 20: The Good, the Bad, and the Ugly of Financing…Equity Investors, Venture Capitalists, Angel Investors, Strategic Investors, Debt, Convertible Debt, Venture Debt, Bank Loans, Personal Debt, Bootstrapping, Customer Financing, Your Own Cash Flow
• Chapter 21: When and How to Raise Money…When to Start Looking for VC Money, The Top 11 Takeaways for Financing Negotiations
• Chapter 22: Forecasting and Budgeting…Rigorous Financial Modeling, Of Course You’re Wrong—But Wrong How?, Budgeting in a Context of Uncertainty, Forecast, Early and Often
• Chapter 23: Collecting Data…External Data, Learning from Customers, Learning from (Un)Employees, Internal Data, Skip-Level Meetings, Subbing, Productive Eavesdropping
• Chapter 24: Managing in Tough Times…Managing in an Economic Downturn, Hope Is Not a Strategy—But It’s Not a Bad Tactic, Look for Nickels and Dimes under the Sofa, Never Waste a Good Crisis, Managing in a Difficult Business Situation
• Chapter 25: Meeting Routines…Lencioni’s Meeting Framework, Skip-Level Meetings, Running a Productive Offsite
• Chapter 26: Driving Alignment…Five Keys to Startup Alignment, Aligning Individual Incentives with Global Goals
• Chapter 27: Have You Learned Your Lesson?…The Value (and Limitations) of Benchmarking, The Art of the Post-Mortem
• Chapter 28: Going Global…Should Your Business Go Global?, How to Establish a Global Presence, Overcoming the Challenges of Going Global, Best Practices for Managing International Offices and Employees
• Chapter 29: The Role of M&A…Using Acquisitions as a Tool in Your Strategic Arsenal, The Mechanics of Financing and Closing Acquisitions, Stock, Cash, Earn Out, The Flipside of M&A: Divestiture, Odds and Ends, Integration (and Separation)
• Chapter 30: Competition…Playing Hardball, Playing Offense vs. Playing Defense, Good and Bad Competitors
• Chapter 31: Failure…Failure and the Startup Model, Failure Is Not an Orphan

Part IV: Building and Leading a Board of Directors

• Chapter 32: The Value of a Good Board…Why Have a Board?, Everybody Needs a Boss, The Board as Forcing Function, Pattern Matching, Forests, Trees, Honest Discussion and Debate
• Chapter 33: Building Your Board…What Makes a Great Board Member?, Recruiting a Board Member, Compensating Your Board, Boards as Teams, Structuring Your Board, Board Size, Board Committees, Chairing the Board, Running a Board Feedback Process, Building an Advisory Board
• Chapter 34: Board Meeting Materials…“The Board Book”, Sample Return Path Board Book, The Value of Preparing for Board Meetings
• Chapter 35: Running Effective Board Meetings…Scheduling Board Meetings, Building a Forward-Looking Agenda, In-Meeting Materials, Protocol, Attendance and Seating, Device-Free Meetings, Executive and Closed Sessions
• Chapter 36: Non-Board Meeting Time…Ad Hoc Meetings, Pre-Meetings, Social Outings
• Chapter 37: Decision-Making and the Board…The Buck Stops—Where?, Making Difficult Decisions in Concert, Managing Conflict with Your Board
• Chapter 38: Working with the Board on Your Compensation and Review…The CEO’s Performance Review, Your Compensation, Incentive Pay, Equity, Expenses
• Chapter 39: Serving on Other Boards…The Basics of Serving on Other Boards, Substance, or Style?

Part V: Managing Yourself So You Can Manage Others

• Chapter 40: Creating a Personal Operating System…Managing Your Agenda, Managing Your Calendar, Managing Your Time, Feedback Loops
• Chapter 41: Working with an Executive Assistant…Finding an Executive Assistant, What an Executive Assistant Does
• Chapter 42: Working with a Coach…The Value of Executive Coaches, Areas Where an Executive Coach Can Help
• Chapter 43: The Importance of Peer Groups…The Gang of Six, Problem-Solving in Tandem
• Chapter 44: Staying Fresh…Managing the Highs and Lows, Staying Mentally Fresh, At Your Company, Out and About, Staying Healthy, Me Time
• Chapter 45: Your Family…Making Room for Home Life, Involving Family in Work, Bringing Work Principles Home
• Chapter 46: Traveling…Sealing the Deal with a Handshake, Making the Most of Travel Time, Staying Disciplined on the Road
• Chapter 47: Taking Stock of the Year…Celebrating “Yes”; Addressing “No”, Are You Having Fun?, Are You Learning and Growing as a Professional?, Is It Financially Rewarding?, Are You Making an Impact?
• Chapter 48:  A Note on Exits…Five Rules of Thumb for Successfully Selling Your Company

 If you’re still with me and interested, again here are the links to pre-order (Print, Kindle).

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.

Secrets to Yawn-Free Board Meetings

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

The objective of board meetings should always be to have great conversations that help you and your executive team think clearly about the issues in front of you, as well as making sure your directors have a clear and transparent view of the state of the business. These conversations come from a team dynamic that encourages productive conflict. There’s no sure-fire formula for achieving this level of engagement, but here are three few guidelines you can follow to increase your chances.

Schedule board meetings in advance, and forge a schedule that works. Nothing is more disruptive – or more likely to drive low turnout – than last minute scheduling. Make sure you, or your executive assistant, knows board members’ general schedules and travel requirements, and whether they manage their own calendar or have their own executive assistant. Set your board meeting schedule for the year in the early fall, which is typically when people are mapping out most of their year’s major activities. If you know that one of your board members has to travel for your meetings, work with the CEOs of the other companies to coordinate meeting dates. Vary the location of meetings if you have directors in multiple geographies so travel is a shared sacrifice.

In the startup stage of our business at Return Path, we ran monthly meetings for an hour, mostly call-in. In the revenue stage, we moved to six to eight meetings per year, two hours in length, perhaps supplemented with two longer-form and in-person meetings. As a growth stage company, we run quarterly meetings. They’re all in-person, meaning every director is expected to travel to every meeting. We probably lose one director each time to a call-in or a no-show for some unavoidable conflict, but, for the most part, everyone is present. We leave four hours for every meeting (it’s almost impossible to get everything done in less time than that) and sometimes we need longer.

Many years, we also hold a board offsite, which is a meeting that runs across 24 hours, usually an afternoon, a dinner, and a morning, and is geared to recapping the prior year and planning out the next year together. It’s especially exhausting to do these meetings, and I’m sure it’s especially exhausting to attend them, but they’re well worth it. The intensity of the sessions, discussion, and even social time in between meetings is great for everyone to get on the same page and remember what’s working, what’s not, and what the world around us looks like as we dive into the deep end for another year.

Build a forward-looking agenda. The second step in having great board meetings is to set an agenda that will prompt the discussion that you want to have. With our current four-hour meetings, our time allocation is the following:

I. Welcomes and framing (5 minutes)

II. Official Business (no more than 15 minutes unless something big is going on)

III. Retrospective (45 minutes)

a. Target a short discussion on highlighted issues

b. Leave some time for Q&A

IV. On My Mind (2 hours)

a. You can spend this entire time on one topic, more than one, or all, as needed.

b. Format for discussions can vary—this is a good opportunity for breakout sessions, for example.

V. Executive Session (30 minutes)

This is your time with directors only, no observers or members of the management team (even if they are board members).

VI. Closed Session (30 minutes)

This is director-only time, without you or anyone else from the management team.

This agenda format focuses your meeting on the future, not the past. In the early years of the business, our board meetings were probably 75 percent “looking backwards” and 25 percent “looking forwards.” They were reporting meetings—reports which were largely in the hands of board members before the meetings anyway. They were dull as anything, and they were redundant: all of our board members were capable of processing historical information on their own. Today, our meetings are probably ten percent “looking backwards” and 90 percent “looking forwards”—and much more interesting as a result.

Separate background reading and presentation materials. Finally, focus on creating a more engaging dialogue during the meeting by separating background reading from presentation materials. In our early days, we created a huge Powerpoint deck as both a handout the week before the meeting and as the in-meeting deck. That didn’t create an engaging meeting.

There’s nothing more mind-numbing than a board meeting where the advance reading materials are lengthy Powerpoint presentations, than when the meeting itself is a series of team members standing up and going through the same slides, bullet by excruciating bullet—that attendees could read on their own.

When we separated the background and presentation materials, people were engaged by the Powerpoint—because it delivered fresh content. We started making the decks fun and engaging and colorful, as opposed to simple text and bullet slides. That was a step in the right direction, but the preparation consumed twice as much time for the management team, and we certainly didn’t get twice the value from it.

Now we send out a great set of comprehensive reading materials and reports ahead of the meeting, and then we have a completely Powerpoint-free meeting. No slides on the wall. This changes the paradigm away from a presentation—the whole concept of “management presenting to the board”—to an actual discussion. No checking email. No yawns. Nobody nodding off. Everyone—management and board—is highly engaged

The Best Place to Work, Part 6: Let People Be People

Last week, in this continuing series on creating the best place to work, I talked about being a great enabler of people, meaning you do your best to let people do their best work.  This week, I want to talk about Letting People Be People.

I wrote about topic a bit this last year when I wrote my series on Return Path’s Core Values, in particular the post on our value People Work to Live, Not Live to Work .

Work-life balance is critical.  I’ve worked in a grind-it-out 100-hour/week environment as an analyst before.  Quite frankly, it sucks.  One week I actually filled in 121 on my hourly time sheet as a consultant.  If you’ve never calculated the denominator, it’s only 168.  Even being well paid as a first-year analyst out of college, the hourly rate sucked.  Thinking about 121 gives me the shivers today…and it certainly puts into perspective that whether you work 40, 45, 50, 55, or 60 hours in a given week can pale by comparison, and all still let you have a life.  An average week of 40 hours probably doesn’t make sense for a high-growth company of relatively well-paid knowledge workers.  But at 121 you barely get to shower and sleep.

While you may get a lot done working like a dog, you don’t get a lot more done hour for hour relative to productive people do in a 50-week environment.  Certainly not 2x.  People who say they thrive on that kind of pressure are simply lying – or to be fair, they’re not lying, but they are pretending they wouldn’t prefer a different environment, which is likely disingenuous and a result of rationalizing their time spent at work.  Your productivity simply diminishes after some number of hours.  So as a CEO, even a hard-charging one, I think it’s better to focus on creating a productive environment than an environment of sustained long hours.

Work has ebbs and flows just like life has ebbs and flows.  As long as the work generally gets done well and when you need it, you have to assume that sometimes, people will work long hours in bursts and sometimes, people will work fewer hours.  Work-life balance is not measured in days or even weeks, but over the long term.  So to that end, We Let People Be People as a means of trading off freedom and flexibility for high levels of performance and accountability.  At Return Path, we create an environment where people can be people by:

• Giving generous maternity leave and even paternity leave, at least relative to norms in the US
• Having a flexible “work from home” policy, as people do have personal things to do during the business day from time to time
• Allowing even more flexible work conditions for anyone (especially new parents) – 3 or 4 days/week if we can make it work
• Letting people take a 6-week paid sabbatical after 7 years, then after every 5 years after that
• Having an “open vacation” policy where people can take as much vacation as they want, as long as they get their jobs done

As with all the posts in this series, this is meant to be general, not specific.  But these are a few of the things we’ve done to Let People Be People, which has created an incredibly productive environment here where people have fun, lead their lives, and still get their jobs done well and on time.

First in my series of posts around creating the best place to work  is to Surround yourself with the best and brightest.  This one is simple.  Build the best team you can possibly build…as you need it.

As a founder, you may be the best person at doing everything in your company, especially if you are a technical founder.  But as my long-time Board member at Return Path Greg Sands always says, when the organism grows, cells start to specialize.  Eventually, you need a liver and a brain.  Just like companies need a head of sales and a CFO (not to imply that Anita likes the occasional cocktail or that Jack likes math – turns out both like both).

How does this come into play as a CEO?

-Don’t be afraid to hire people better than you at their specialty – older, wiser, more experienced, more expensive

– Check references carefully – don’t get suckered in by resume or rolodex – some successful big company people don’t actually know how to do work or build a business, so you have to dig and find back-channel references

– Don’t overhire before you’re ready, but especially as a start-up, better to hire 3 months before you need the position, not 6 months too late

-Remember that you are the CEO.  Even if you hire very experienced people in specific roles, you have the best global view of everything going on in the company.  And you need to pay attention to people on your team and actively manage them, even experts who are older or wiser than you are

Surrounding yourself with the best and brightest can be daunting and even threatening to some CEOs.  But you have to do it to grow your business.  And you have to keep doing it as you keep growing your business (and your staff has to do the same!).

5 Ways to Get Your Staff on the Same Page

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

When a major issue arises, is everybody at your company serving the same interests? Or is one person serving the engineering team, another person serving the sales team, one board member serving the VC fund, another serving the early-stage “angels” and another serving the CEO? If that’s the case, then your team is misaligned. No individual department’s interests are as important as the company’s.

To align everyone behind your company’s interests, you must first define and communicate those goals and needs. This requires five steps:

1. Define the mission. Be clear to everyone about where you’re going and how you’re going to get there (in keeping with your values).
2. Set annual priorities, goals, and targets. Turn the broader mission into something more concrete with prioritized goals and unambiguous success metrics.
3. Encourage bottom-up planning. You and your executive team need to set the major strategic goals for the company, but team members should design their own path to contribution. Just be sure that you or their managers check in with them to assure that they remain in synch with the company’s goals.
4. Facilitate the transparent flow of information and rigorous debate. To help people calibrate the success, or insufficiency, of their efforts, be transparent about how the organization is doing along the way. Your organization will make better decisions when everyone has what they need to have frank conversations and then make well-informed decisions.
5. Ensure that compensation supports alignment (or at least doesn’t fight it). As selfless as you want your employees to be, they’ll always prioritize their interests over the company’s. If those interests are aligned – especially when it comes to compensation – this reality of human nature simply won’t be a problem.

Taken in sequence, these steps are the formula for alignment. But if I had to single out one as the most important, it would be number 5: aligning individual incentives with companywide goals.

It’s always great to hear people say that they’d do their jobs even if they weren’t paid to, but the reality of post-lottery-jackpot job retention rates suggests otherwise. You, and every member of your team, “work” for pay. Whatever the details of your compensation plan, it’s crucial that it aligns your entire team behind the company’s best interests.

Don’t reward marketers for hitting marketing milestones while rewarding engineers to hit product milestones and back office personnel to keep the infrastructure humming. Reward everybody when the company hits its milestones.

The results of this system can be extraordinary:

• Department goals are in alignment with overall company goals. “Hitting product goals” shouldn’t matter unless those goals serve the overall health of your company. When every member of your executive team – including your CTO – is rewarded for the latter, it’s much easier to set goals as a company. There are no competing priorities: the only priority is serving the annual goals.
• Individual success metrics are in alignment with overall company success metrics. The one place where all companies probably have alignment between corporate and departmental goals is in sales. The success metrics that your sales team uses can’t be that far off from your overall goals for the company. With a unified incentive plan, you can bring every department into the same degree of alignment. Imagine your general counsel asking for less extraneous legal review in order to cut costs
• Resource allocation serves the company, rather than individual silos. If a department with its own compensation plan hits its (unique) metrics early, members of that team have no incentive to pitch in elsewhere; their bonuses are secure. But if everyone’s incentive depends on the entire company’s performance, get ready to watch product leads offering to share developers, unprompted.

This approach can only be taken so far: I can’t imagine an incentive system that doesn’t reward salespeople for individual performance. And while everyone benefits when things go well, if your company misses its goals, nobody should have occasion to celebrate. Everybody gets dinged if the company doesn’t meet its goals, no matter how well they or their departments performed. It’s a tough pill to swallow, but it also important preventive medicine.

Book Short:  On The Same Page

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:

1. Build and maintain a cohesive leadership team
2. Create organizational clarity
3. Overcommunicate organizational clarity
4. 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!

In addition to our work on helping CEOs understand board-building best practices, which I posted about last week, I’ve spent the past several months publishing a second series of blog posts to help current and aspiring directors (really, any senior executive!) understand the behind-the-scenes details of private company board service. This second series is also now an eBook and its content will also feature in the upcoming second edition of Startup Boards that I’m collaborating on with Brad Feld and Mahendra Ramsinghani.

When Bolster published the findings of our Board Benchmarking study, we revealed that 4 out of 5 seats on private company boards today are held by individuals who are white, and 86% of director seats are held by men.

And we also learned that 2 out of 3 CEOs are open to bringing on first-time directors to their boards, largely to help add some much-needed diversity to the most senior ranks of corporate service. To assist current and aspiring board directors out there, we decided to aggregate our team’s collective brainpower to shed light on how to get recruited for a board role, what to expect once you’re there, and how to make an impact.

You can see the full list of blog posts here:

• Introduction to Startup Boards
• How to Prepare Yourself to Get on Your First Board
• Should You Serve on an Advisory Board?
• Interviewing for a Board Role
• What You Need to Know About Board Compensation
• Preparing for Your First Board Meeting
• Corporate Governance as a Board Member
• How to Be a Great Board Member
• When Things Aren’t Black and White: How to Deal with Murky Areas
• Giving Difficult Feedback and Making Your Voice Heard
• How to Know if You’re Doing a Good Job as a Board Member

You can download all of these in an eBook, How to Succeed in Your First Board Role, from the Bolster web site.

We hope this book helps inspire and empower you on your own journey as a board director. And if you’d like to get access to more exclusive content like this and be considered for a board role in the future, you can sign up as a Bolster member here.

Automated Love

Return Path is launching a new mini feature sometime this week to our clients.  Normally I wouldn’t blog about this — I think this is mini enough that we’re probably not even saying much about it publicly at the company.  But it’s an interesting concept that I thought I’d riff on a little bit.

I forget what we’re calling the program officially — probably something like “Client Status Emails” or “Performance Summary Alerts” — but a bunch of us have been calling it by the more colorful term “Automated Love” for a while now.

The art of account management or client services for an on-demand software company is complex and has evolved significantly from the old days of relationship management.  Great account management now means a whole slew of new things, like Being The Subject Matter Expert, and Training the Client.  It’s less about the “hey, how are things going?” phone call and more about driving usage and value for clients.

As web services have taken off, particularly for small businesses or “prosumers,” most have built in this concept of Automated Love.  The weekly email from the service to its user with charts, stats, benchmarks, and links to the web site, occasionally with some content or blog posts.  It’s relatively easy (most of the content is database driven), it reminds customers that you’re there, working on their behalf in the background, it tells them what happened on their account or how they’re doing, it alerts them to current or looming problems, and it drives usage of your service.  As a bonus for you internally, usually the same database queries that produce a good bit of Automated Love can also alert your account management team when a client’s usage pattern of your service changes or stops entirely.

While some businesses with low values of any single customer value can probably get away with having a client service function based ENTIRELY on Automated Love, I think any business with a web service MUST have Automated Love as a component of its client service effort.

I love innovation, and process is no different than product or business model in that regard. I’ve run and attended several hundred board meetings over the years, both those of companies where I’ve been CEO or Chairman, and those where I’m a director. I’ve written a lot about how I like running board meetings in Startup CEO, and as I mentioned the other day, I’m a co-author of a Second Edition of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, which is coming out in June and is available to pre-order now, along with Brad Feld and Mahendra Ramsinghani.

There are two adaptations I’ve made to my standard board routines in the last year or so, one driven by the pandemic and one not.

In olden times (that makes me sound like I’m 400 years old, but “pre-covid” sounds so clinical), I used to have a board dinner the night before or after every board meeting, and of course, everything was in person. That was a really important ritual in my mind towards the end of building the board as an effective team, where people on the team know each other as people, share things going on in their lives, share vulnerabilities, and develop bonds of trust. Without regular in-person meetings and dinners or social events, that gets a lot harder. Even when we get back to “normal,” I imagine the most we’ll do in-person board meetings is 1-2x/year.

What’s the zoom version of this?

We now do two 30-minute Executive Sessions (directors only) one before the board meeting officially starts and observers and team join, as well as the traditional one after the meeting ends. The purposes of the two sessions are different. The standard post-meeting Executive Session follows up on the meeting and has me talk about business or team issues that I don’t want to talk about with the full group present or get feedback from the board. But the one before the meeting is almost entirely social. I try to come up with a different question or topic to get all of us talking that is not about Bolster. Last week’s meeting was a simple “what’s the best thing that’s happened to you so far in 2022, and what’s the worse?” One time I asked everyone to show a picture from their phone photo roll and talk about it. You get the idea. It’s not the same as a dinner, but it seems like an effective substitute given the medium.

The second adaptation, and full credit to Fred for suggesting this one a while back, is the post-meeting survey. Now immediately after every Board meeting, I send a simple Google form to each director with the following questions:

• What are 1-3 areas/specifics where we are doing well?
• What are 1-3 areas/specifics you’re concerned about or where we could do better?
• Did the board book have the right level of detail and commentary?  Is there anything you’d like to see change about the format or the content?
• Did the meeting meet your objectives for learning and discussion? 
• If not, why not?
• Do you have any other feedback for Matt at this time?

I get great feedback, almost immediately and always from all board members, while things are still fresh in everyone’s mind. I’m planning to do this whether or not the meeting is remote…although it’s definitely good when the meeting is remote, and things like Executive Session, Closed Session, and debrief with me after Closed Session are quick or sometimes rushed.

There’s always room for innovation, even in standard and time-tested processes like board meetings.

Fred, Brad, and Jerry have done a bunch of postings recently, and threaten to do more, sharing the VC perspective on many aspects of startups and entrepreneurship. I thought it might be interesting to share the entrepreneur’s perspective on the same subjects. I’ll try to cross-post and keep pace, but I’m already a couple behind, and I can’t crank out postings as fast as these guys can! (For reference, Fred and Brad are on my board, and Jerry as Fred’s partner is an advisor to my company, Return Path.)

Topic 1: Boards of Directors. All three have many good points. Brad says that boards come in three flavors (working, reporting, and lame duck), and that small companies need working boards which include other entrepreneurs in the industry as well as management and investors. He also advises to take good care of directors and not let them get bored. Fred calls the good ones engaged boards (interactive, candid, engaged, passionate, and involved) and says that while you can have a good company without an engaged board and even with a bored bored on occasion, to have a great business you need an engaged board. Finally, Jerry says that you should pick your board carefully and build it with some diversity like you would a management team and to avoid people who will yes you.

I basically agree with all of these points, and would add the following four thoughts for entrepreneurs:

1. Building a board can be one of a CEO’s greatest trump cards. Without being even a little bit disingenuous, you can use the “I’m the CEO and would like to talk to you about a potential board seat with my company” as an entree to meet face to face with some of the most interesting, senior, brand-name people in your industry (turns out, flattery will occasionally get you somewhere). Use this card wisely and sparingly, and always be prepared to follow up on your meetings, but take full advantage of it as a way to network. You never know what opportunities you’ll uncover along the way.

2. Don’t think of managing your Board as a burden. Communicate early and often to your Board members and make sure all big conversations and debates are pre-wired in one-to-one conversations before Board meetings, and that debates are framed and researched properly in advance of meetings. Nail the basics (reporting, financial reviews, well-crafted and easy-to-read materials sent out several days before the meeting), so you can focus the valuable meeting time on strategy, not on the minutiae.

3. Figure out how to work differently with investor directors and outside directors. VCs who sit on your board have very different interests, time availability, and things to contribute than outside directors, especially non-retired industry executives. Not all directors are created equally, and you don’t have to behave as if they are.

4. Sit on a board yourself. There’s nothing like a real-live counterpoint to make you take a step back and think about how to build and run an effective board. Find something — another startup, a nonprofit, your high school or college alumni association — to join as a board member. Watch and learn.

All that said, the most important thing I’ve found in running a board is following Brad, Jerry, and Fred’s collective wisdom about fostering an engaged/working board. Definitely don’t let them get bored on you!