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.

Book Short:  Two New Ones from Veteran Writers

I’m feeling very New York this week.  I just read both Outliers: The Story of Success, by Malcolm Gladwell, and Hot, Flat, and Crowded: Why We Need a Green Revolution – and How It Can Renew America, by Tom Friedman.  Both are great, and if you like the respective authors’ prior works, are must reads.

In Outliers, Gladwell’s simple premise is that talents are both carefully cultivated and subject to accidents of fate as much as they are genetic.  I guess that’s not such a brilliant premise when you look at it like that.  But as with his other two books, The Tipping Point (about how trends and social movements start and spread) and Blink (about how the mind makes judgments), his examples are fascinating, well researched, and very well written.  Here are a couple quick nuggets, noting that I don’t have the book in front of me, so my numbers might be slightly off:

• Of the 200 wealthiest people in human history, 9 were Americans born within 5 years of each other in the 1830s – far from a normal distribution for wealth holders/creators
• Most Silicon Valley titans were both within 2 years of each other in 1954-1955
• 40% of great hockey players are born in Q1; 30% in Q2; 20% in Q3; and 10% in Q4, as the “cutoff date” for most youth leagues is January 1, so the biggest/oldest kids end up performing the best, getting the best coaches and most attention that propels them throughout their careers

Also, as with his other books, it’s hard to necessarily draw great and sweeping conclusions or create lots of social policy, both of which are quite tempting, as a result of the data.  Scholarly, comprehensive research it might not be, but boy does he make you think twice about, well, lots of things.

In Hot, Flat, and Crowded, Tom Friedman makes a convincing case that two wrongs can make a right, or more to the point, that fixing two wrongs at the same time is a good way of fixing each one more than otherwise would be possible.  What I like best about this book is that it’s not just another liberal journalist trashing America — Friedman’s whole premise here (not to mention language) is fiercely optimistic and patriotic, that if we as a country take a sweeping global leadership role in containing CO2 emissions, we will both save the planet and revive our economy, sustaining our global economic leadership position into the next century at a time when others are decrying the end of the American empire.

His examples are real and vivid.  Like Gladwell, one never knows how unbiased or comprehensive Friedman is, but he covers some of these topics very poignantly:

• The very strong negative correlation between control of oil supply and democracy/freedom
• A comprehensive vision for the energy world of the future that’s very cool, apparently has already been piloted somewhere, and feels like it’s actually doable
• The startling numbers, even if you sort of know them already, about the sheer number of people who will be sharing our planet and consuming more and more resources in the coming decades
• How too many years of being a privileged nation has led to politics he brilliantly calls “dumb as we wanna be”

Friedman calls his mood sober optimism — that’s a good description.  It’s a very timely book as many Americans hold out hope for the new administration’s ability to lead the country in a positive direction and also restore American’s damaged image in the world come January 20. I have to confess that I still haven’t read Friedman’s The Earth Is Flat, although I read him in the New York Times enough and have seen enough excerpts (and lived in business enough the last 5 years!) to get the point.  And actually, Hot, Flat, and Crowded has enough of the “Flat” part in it that even if you haven’t read The Earth is Flat, you’ll get more than just the gist of it.

Book Short:  Required Reading

The Leadership Pipeline, by Ram Charan, Stephen Drotter, and James Noel, should be required reading for any manager at any level in any organization, although it’s most critical for CEOs, heads of HR, and first-time managers.  Just ask my Leaderhip Team at Return Path, all of whom just had to read the book and join in a discussion of it!

The book is easy to read, and it’s a great hands-on playbook for dealing with what the authors call the six leadersihp passages:

From Individual Contributor to Manager (shift from doing work to getting work done through others)

From Manager to Manager of Managers (shift to pure management, think beyond the function)

From Manager of Managers to Functional Manager (manage outside your own experience)

From Functional Manager to Business Manager (integrate functions, shift to profit and longer term views)

From Business Manager to Group Manager (holistic leadership, portfolio strategies, value success of others)

From Group Manager to Enterprise Manager (outward looking, handle external and multiple constituencies, balance strategic and visionary long-term thinking with the need to deliver short-term operating results)

All too often, especially in rapidly growing companies, we promote people and move them around without giving enough attention to the critical success factors involved in each new level of management.  I’ve certainly been guilty of that at Return Path over the years as well.  It’s just too easy to get trapped in the velocity of a startup someitmes to forget these steps and how different each one is.  This book lays out the steps very neatly.

It’s also one of the few business books that at least makes an attempt — and a good one at that — at adapting its model to small companies.  In this case, the authors note that the top three rungs of the pipeline are often combined in the role of CEO, and that Manager of Managers is often combined with Functional Managers.

Anyway, run, don’t walk, to buy this one!

Counter Cliche:  Head Lemming

Fred’s VC Cliche of the Week last week was that leadership is figuring out where everyone is going and then getting in front of them and saying “follow me.” While it’s certainly true that juming out in front of a well-organized, rapidly moving parade and becoming the grand marshal (or maybe the baton twirly person) is one path to successful leadership, CEOs do have to be careful about selecting the right parade to jump in front of for two reasons.

First, just because lots of people are going in a specific direction doesn’t mean it’s right.  There’s nothing good about ending up as the Head Lemming.  It just means you go over the cliff before the rest of the troops.  Lots of smart people thought home delivery of a stick of gum made sense and was worth investing in, but it certainly put a kink in George Shaheen’s career.

Second, even if the parade is a good one, the organization you run might not be best equipped to take advantage of it.  Again, you find yourself in the undesirable position of being the Head Lemming.  Gerry Levin and Steve Case fell in love with convergence story (one of the biggest parades of the last 10 years), but in the end, Time Warner and AOL just couldn’t cope with the merger.  Neither Gerry nor Steve survived the merger.

So if you’re going to follow the VC cliche and jump out in front of a crowd to lead it, make sure you select your crowd carefully.

Scaling Me

Two things have come up over the last couple years for me that are frustrations for me as a CEO of a high growth company.  These are both people related — an area that’s always been the cornerstone of my leadership patterns.  That probably makes them even more frustrating.

Frustration 1:  Not knowing if I can completely trust the feedback I get from deep in the organization.  I’ve always relied on direct interactions with junior staff and personal observation and data collection in order to get a feel for what’s going on.  But a couple times lately, people had been admonishing me (for the first time) when I’ve relayed feedback with comments like, “of course you heard that — you’re the CEO.”

So now the paranoid Matt kicks in a bit.  Can I actually trust the feedback I’m getting?  I think I can.  I think I’m a good judge of character and am able to read between the lines and filter comments and input and responses to questions I ask.  But maybe this gets harder as the organization grows and as personal connections to me are necessarily fewer and farther between.

Frustration 2:  Needing to be increasingly careful with what I say and how I say it.  This comes up in two different ways.  First, I want to make sure that while I’m still providing as transparent leadership as I can, that I’m not saying something that’s going to freak out a more junior staff member because they’re missing context or might misinterpret what I’m saying.  Ok, this one I can manage.

But the tougher angle on this is having unintended impact on people.  Throwing out a casual idea in a conversation with someone in the company can easily lead to a chain reaction of “Matt said” and “I need to redo my goals” conversations that aren’t what I meant.  So I’ve done some work to formalize feedback and communication loops when I have skip-level check-ins, but it’s creating more process and thought overhead for me than I’m used to.

Nothing is bad here – just signs of a growing organization – but some definite changes in how I need to behave in order to keep being a strong and successful leader.

The Advantage: Why Organizational Health Trumps Everything Else In Business is Patrick Lencioni’s newest book.  Unlike most or all of his other books (see the end of this post for the listing), this one is not a fable, although his writing style remains very quick and accessible.

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:

• The Three Signs of a Miserable Job (post, book)
• The Five Temptations of a CEO (post, book)
• The Four Obsessions of an Extraordinary Executive (post, book)
• Death by Meeting (post, book)
• The Five Dysfunctions of a Team (post, book, Field Guide)
• Silos, Politics and Turf Wars (post, book)
• Getting Naked (post, book)
• The Advantage (book)

Running a Productive Offsite

A couple OnlyOnce readers asked me to do a post on how I run senior team offsites.  It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.

My senior team has four offsites per year.  I love them.  They are, along with my Board meetings, my favorite times of the year at work.  Here’s my formula for these meetings:

–          WHY:  There are a few purposes to our offsites.  One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level.  So for us, these are the only times of the year that we are actually in the same place.  But even if we were all in one place, we’d still do them.  The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time.  The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics.  It’s critically important to build and sustain deep relationships across the Executive Team.  We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company.  As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical

–          WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total).  Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people).  That part is new as we’ve gotten bigger.  In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics

–          WHERE:  Offsites aren’t always offsite for us.  We vary location to make geography work for people.  And we try to contain costs across all of them.  So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel.  Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place.  Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night

–          WHEN:  4x/year at roughly equal intervals.  We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded.  Now we basically do them between Board meetings.  The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year.  Our general formula when it’s the smaller group is two days and at least one, maybe two dinners.  When it’s the larger group, it’s three days and at least two dinners.  For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.

–          WHAT:  Our offsites are super rigorous.  We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations.  The agenda for these offsites varies widely, but the format is usually pretty consistent.  I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union.  Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc.  We always try to spend half a day on team and individual development.  Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing.  Then we have a team development plan check-in that’s the same, but about how the team is interacting.  We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time.  Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!).  There’s also time at breaks for sub-group meetings and ad hoc conversations.  We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it.  Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m.  We usually have a closing check-out, next steps recap type of exercise as well.

–          HOW:  Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.

I’m sure I missed some key things here.  Team, feel free to comment and add.  Others with other experiences, please do the same!

Startup CEO (OnlyOnce- the book!), Part II – Crowdsourcing the Outline

As I mentioned a few weeks ago here, I’m excited to be writing a book called Startup CEO:  A Field Guide to Building and Running Your Company, to be published by Wiley & Sons next summer.  Since many readers of OnlyOnce are my target audience for the book, I thought I’d post my current outline and ask for input and feedback on it.  So here it is, still a bit of a work in progress.  Please comment away and let me know what you think, what’s missing, what’s not interesting!

1           Part One: Vision and Strategy (Defining the Company)
1.1          Setting the Company’s Agenda
1.2          NIHITO! (or, “Nothing Interesting Happens in the Office”)
1.3          Setting the Business Direction
1.4          Strategic Planning, Part I: Turning Concepts Into Strategy
1.5          Strategic Planning, Part II: Creating the Plan
1.6          Defining Mission, Vision and Values
1.7          Communicating Vision and Strategy
1.8          The Role of M&A
1.9          The Art of the Pivot
1.10       How Vision and Strategy Change over Time

2           Part Two: Talent (Building the Company’s Human Capital)
2.1          Building a Team
2.2          Scaling the Team
2.3          Culture
2.4          Interviewing
2.5          Recruiting
2.6          Onboarding
2.7          Setting Goals
2.8          Feedback
2.9          Development
2.10       Compensation
2.11       Promoting
2.12       Rewarding
2.13       Managing Remote Offices and Employees
2.14       Firing: When It’s Not Working
2.15       How Talent Changes over Time

3           Part Three: Execution (Aligning Resources with Strategy)
3.1          Making Sure There’s Enough Money in the Bank
3.2          Types of Financing
3.3          Fundraising Basics
3.4          Negotiating Deals
3.5          Pros and Cons of Outside Financing
3.6          Forecasting and Budgeting
3.7          Creating a Company Operating System
3.8          Meeting Routines
3.9          Driving Alignment
3.10       A Metrics-Driven Approach to Running a Business
3.11       Learning
3.12       Post-Mortems
3.13       Thinking About Exits
3.14       How Execution Changes over Time
3.14.1      Finance
3.14.2      Execution

4           Part Four: Management And Leadership (The How of Being a CEO)
4.1          Leading an Executive Team
4.2          Critical Personal Traits
4.3          Being Collaborative
4.4          Being Decisive: Balancing Authority and Consensus
4.5          The Value of Symbolism
4.6          Getting the Most out of People
4.7          Diving Deep without Being Disruptive
4.8          Articulating Purpose
4.9          Collecting Data from the Organization
4.10       Managing in an Economic Downturn
4.11       Managing in Good Times vs. Bad Times
4.12       Communication
4.12.1      Macro (to Your Company and Customers)
4.12.2      Micro (One-on-One)
4.13       How Management and Leadership Change over Time

5           Part Five: Boards (A Unique Aspect of the CEO’s Job)
5.1          Building Your Board
5.2          Meeting Materials
5.3          Meetings
5.4          Between Meetings
5.5          Making Decisions and Maximizing Effectiveness
5.6          The Social Aspects of Running a Board
5.7          Working with the Board on Compensation
5.8          Evaluating the Board
5.9          Serving on Other Boards
5.10       How Boards Change over Time

6           Part Six: Managing Yourself So You Can Manage Others
6.1          Creating a Personal Operating System
6.2          Working with an Executive Assistant
6.3          Working with a Coach
6.4          Finding Your Voice
6.5          The Importance of Peer Groups
6.6          Your Family
6.7          Taking Stock
6.8          Staying Fresh
6.9          Staying Healthy
6.10       Traveling

I was the head coach of my two older kids’ little league team this past spring.  The whole thing was a little bit of an accident – I vaguely volunteered for something and ended up in charge.  The commitment was a little daunting, but I was ok with it since the season was only a couple months long, it was both Casey and Wilson, and both kids, especially Wilson, are really into baseball.  Other than helping out a bit here and there, I’d never coached a sports team before.

What started off as an unclear assignment ended up as one of the most fun and fulfilling things I’ve done in years.  I loved every minute of it, looked forward to our practices and games, was hugely bummed out when we got rained out, and never had a moment where I couldn’t make the time for it (though clearly the hours had to come from somewhere!).  Given some of the overlap between leading a sports team and leading a company, I thought I’d reflect on the experience a bit here.  There are some common themes between this post and something I wrote years ago, Parenting and Corporate Leadership, with the same caveat that no, I don’t think employees are children or children are employees.  But here are some things I take away from the experience and apply or compare to work.

We established a clear philosophy and stuck to it.  That’s a step that lots of coaches – and managers in the workplace – miss.  The other coaches and I discussed this before the first practice, agreed on it, and shared it directly with the kids.  For this age group in particular, we felt that we were there first and foremost to have fun; second to learn the game; and third, to play hard and fair.  Note there was nothing in this about winning, and that we were really specific about the order of the three objectives.  Even 7 and 8 year olds know the difference between “win at all costs” and “have fun and play ball.”  We reinforced this at every practice and at every game.  Being intentional about a philosophy and communicating it (and of course sticking to it) are key for any leadership situation.

We got lucky.  As I repeatedly said to the parents on the team, we had a group of awesome kids – happy and generally paying attention, and not one troublemaker in the bunch; and we had a group of awesome parents – responsive, supportive, and not a single complaint about what position a kid was playing or where someone was in the batting order.  I’d heard horror stories about both kids and parents from other coaches ahead of time.  It’s possible that the other coaches and I did such a good job that both kids and parents were great all the time…but I think you have to chalk most of that up to the luck of the draw.  Work isn’t all that different.  Having stakeholders who are consistently positive forces is something that sometimes you can shape (you can fire problematic employees) but often you can’t, in the case of customers or even Board members.  Luck matters.

Stakeholder alignment was a critical success factor.  Having said that, I do think the coaches and I did a good job of keeping our stakeholders aligned and focusing on their needs, not ours.  We put extra effort into a regular cadence of communication with the parents in the form of weekly emails and a current web site.  We used those emails to highlight kids’ performance and also let parents know what we’d be working on in practice that week.  We made sure that we rotated kids in the batting order so that everyone got to bad leadoff once and cleanup once.  We rotated kids so that almost every kid played half of each game in the infield and half in the outfield.  We took any and all requests from kids who wanted to play a specific position for a few innings.  Many of these basic principles – communicating well, a clear operating system, listening to stakeholders, a People First approach – are lessons learned from work as a CEO.

Proper expectations and a large dose of patience helped.  After the first couple games, we were 0-2, and I was very frustrated.  But I reminded myself that 7 and 8 year olds are just kids, and my frustration wasn’t going to help us achieve our objectives of having fun and learning the game.  So I recalibrated my expectations and took much more of a laid-back attitude.  For example, any time I saw one kid goofing off a little bit in practice, I gently got him or her back in line.  But when I saw multiple kids’ attention fading, I took it as a sign that whatever I was doing as a coach wasn’t working, called a break, and did something else.  This kind of “look in the mirror” approach is always helpful at work, too.

Reward and recognition were key.  We definitely adopted a Whale Done! approach with the kids.  We got the kids in the dugout fired up to cheer on batters.  First base coaches did big high fives, smiles, and literal pats on the back for every hit.  Post-game huddles and emails to parents focused on highlights and what went right for the kids.  One of my favorite moments of the season was when one player, who only had one hit all year and struck out almost every time at bat, had two hits, an RBI, and a run scored in our final game.  Not just the coaches, but the other kids and all the parents went absolutely BANANAS cheering for this player, and it brought huge smiles to all our faces.  I am 100% certain that the focus on the positive encouraged the kids to try their hardest all season, much as I believe that same philosophy encourages people to take risks and work hard at the office.

The biggest thing I take back to the workplace with me from the experience.  I was reminded about how powerful achieving a state of “flow,” or “relaxed concentration” is.  I recounted these principles in this blog post from a couple different books I’ve read over the years – Mihaly Csikszentmihalyi’s Flow and Tim Gallway’s Inner Game books – Golf, Tennis, and Work.  The gist of achieving a state of flow is to set clear goals that are stretch but achievable, become immersed in the activity, pay attention to what’s happening, and learn to enjoy immediate experience.  All leaders – in sports, business, or any walk of life – can benefit from this way of living and leading.

I loved every minute of coaching.  It helped that we ended up with a really strong record.  But more than that, building relationships with a bunch of great kids and great parents was fun and fulfilling and incredibly thankful and rewarding.  The “thank you ball” that all the kids autographed for me is now a cherished possession.  Working and getting extra time with my own two kids was the icing on the cake.  All I want to know is…is it time for next season yet?  I am ready!

This post is really for Coaches Mike, Paul, and Oliver; and players Emily, Casey, Lauryn, Mike, Josh, Holden, Hudson, Wilson, Drew, Kevin, Matthew, and Christian.

My dad (one of my main CEO/entrepreneur role models) and I team-teach a business school class in entrepreneurial leadership every year at USD where a friend of his is the professor.  Sometimes I go in person, usually I just do it by video.  We did this a few weeks ago, and my dad talked through a decision-making framework that I’d never heard him mention before.

I sketched it out and really like it and am already using it internally, so I thought I would share it here as well:

To walk through it, delegating decision-making to someone on your team can be as simple as understanding where a decision falls along two different spectrums.  On the vertical axis is “How familiar is the person with this type of decision?” – meaning, has the person seen and made this kind of decision before?  This could be something like firing an employee, signing a contract, negotiating a vendor agreement.  On the horizontal axis is “What are the consequences of getting the decision wrong?” – which is really self explanatory…how big a deal is this?

The primary, upper right quadrant of “The person has made this decision before, and it’s not a huge deal” is an easy one – delegate the decision-making authority.  The two middle quadrants of “big deal, but familiar with the decision” and “never seen this before, but not a big deal” are ripe for the old adage of ask forgiveness later, not permission first, meaning it’s ok to delegate decision-making authority, but hold the person accountable for letting you know about decisions like that so you can be on the lookout for potential required clean-up.

But what I love most is the way my dad framed the final quadrant (lower left here), which is “high stakes decision, never seen this situation before.”  It can be tempting for a senior manager or CEO to just take this quadrant over and remove decision-making authority from a team member.  But it’s also a perfect teaching/coaching moment.  So the rule of thumb for this quadrant is “make the decision with me, but please come to me with a proposal on it.”

And that’s why my dad is such a great business mentor!

Last week I wrote about The Tension That Will Come With the Future of Work.  No one knows what the post-pandemic world of office vs. remote work will look like, but there are going to be some clear differences between how people will respond to being in offices or not being offices going forward.  As I said in that post, I think the natural, gravitational pull for senior people will be to do more remote work, because of a combination of their commutes, their personal time, their work setups at home, and their level of seniority…but with the possible exception of engineers, “all remote” may actually not be in the best interest of a number of junior or more introverted team members.

Two things popped up in the last few days that are making it clear to me that there’s another issue all of us — whether you’re a CEO or CXO or an entry level employee — will face.  We’ve become much more efficient in how we do our jobs and run our lives.  In my case, I’ll go ahead and say it — I’m addicted to the efficiency and scarcity of social interactions in my work life now in a way that I’m going to find hard to unwind, so I’m calling it “ruthless efficiency.”

Example 1 is a time-based example.  I’ve been doing virtually all client-related meetings, whether sales calls or customer success calls, in 30 minutes over Zoom or equivalent for a year now.  Sometimes I even get one done in 15 minutes.  Very, very rarely, I’ll book one for an hour.

One of my Bolster colleagues who lives not too far away in Connecticut is having drinks with a very important potential partner one night next week as the temperatures outside warm up here in the northeast.  She invited me to join — and really, I should join.  But then “ruthless efficiency math” sets into my thinking.  Instead of a 30 zoom, this will take me three hours – an hour drive each way plus the meeting.  Maybe I get lucky and I can do a call or two from the car, but is the meeting really worth 4-6x the amount of time just so I can be in person?  Even though this is the kind of thing I would have done without hesitation a year ago…that calculus is really hard to make from where I sit today.

Example 2 is an expense-based example.  We have spent basically $0 for a year on T&E.  Now we are planning some kind of a multi-day team meeting a few weeks from now around the 1-year anniversary of the company to work on planning for the next couple quarters.  The quarterly offsite, including travel, hotels, etc., has been a deeply-ingrained part of my leadership Operating System for 20-25 years now.  OF COURSE we should do this meeting in person and offsite if the public health environment allows it and people are comfortable.  But then “ruthless efficiency math” sets into my thinking.  What’s this meeting going to cost?  $10,000?  Depends where we do it and how many team members come since we have people in multiple cities.  But YIKES, that’s a lot of money.  We are a STARTUP.  Shouldn’t we use money like that for some BETTER purpose?

Forget the big things.  I think we all realize that we don’t have to hop on a plane now and do a day trip to the other coast or Europe or Asia for a couple meetings unless those meetings are do-or-die meetings.  It’s these little things that will be tough to readjust now that we’ve all gotten used to having hours upon hours, and dollars upon dollars, back on our calendars and balance sheets because we’ve gotten addicted to the amazing, and yet somewhat ruthless efficiency of the knowledge worker, pandemic, work from anywhere, get it done in 30 minutes on a screen way of life.