As I mentioned the other day, the second edition of Startup CEO is out.  This post is a teaser for the content in one of the new chapters in this edition on Authentic Leadership.

As I mentioned last week, the book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events. Two of those principles, which are timeless and transcend turmoil, uncertainty, time and place, are creating space to think and reflect and being intentional in your actions. In a world in which CEOs are increasingly called upon to deal with more than traditional business (pricing, strategy, go-to market approaches, team building, etc.) it’s imperative to approach and solve challenging situations from a foundation that doesn’t waver. 

At Return Path our values were the foundation that provided a lens through which we made every decision. Well, not every decision, only the good ones. When we strayed from our core values, that got us into trouble. The other principle, outlined in Chapter 1 of the Second Edition, is leading an organization authentically.

Let me provide a couple concrete examples of what I mean by “Authentic Leadership” since the term can be interpreted many ways.

One example is to avoid what I call the “Say-Do” gap.  This is obviously a very different thread than talking about how the company relates to the outside world and current events.  But in some ways, it’s even more important.  A leader can’t truly be trusted and followed by their team without being very cognizant of, and hopefully avoiding close to 100%, any gap between the things they say or policies they create, and the things they do.  There is no faster way to generate muscle-pulling eyerolls on your team than to create a policy or a value and promptly not follow it. 

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

What does that say about the CEO? How engaged are employees likely to be, how much effort are they willing to devote to the company if there are special rules for the executives? You can make any rule you want — as you probably know if you have read a bunch of my posts or my book over the years, I’m a proponent of rule-light environments — but you can’t make rules for everyone else that you aren’t willing to follow yourself unless you own the whole company and don’t care what anyone thinks about you or says about you behind your back.

Beyond avoiding the Say-Do Gap, this new chapter of the book on Authentic Leadership also talks about how CEOs respond to current events in today’s increasingly politicized and polarized world.  This has always felt to me like a losing proposition for most CEOs, which I talk about quite a bit in the book.  When the world is polarized, whatever you do as CEO, whatever position you take on things, is bound to upset, alienate, or infuriate some nontrivial percentage of your workforce.  I even give some examples in the book of how I focused on using the company’s best interests and the company’s values as guideposts for reacting (or not reacting) to politically divisive or charged issues like guns or “religious liberty” laws.  I say this noting that there are some people who *believe* that their side of an issue like this is right, and the other side is wrong, but the issues have some element of nuance to them.

Today’s world feels a bit different, and I’m not sure what I would be doing if I was leading a known, scaled enterprise at this stage in the game.  The largely peaceful protests around all aspects of racial injustice in America in the wake of the murder of George Floyd — and the brutality and senselessness of that murder itself — have caused a tidal wave of dialog reaching all corners of the country and the world.  The root of this issue doesn’t feel to me like one that has a lot of nuance or a second side to the argument.  After all, what reasonable person is out there arguing that George Floyd’s death was called for, or even that black Americans don’t have a deep-seeded and widespread reasonable claim to inequality…even if their view of what to do about it differs?

I *think* what I would be doing in a broader leadership role today is figuring out what my organization could be doing to help reduce or eliminate structural racial inequality where we could based on our business, as opposed to driving my organization to take a specific political stand. I know for sure that I wouldn’t solicit feedback from a select group of people only, but I would create a space where voices from across the organization (and stakeholders outside of it as well) could be heard. That’s not a solution, but a start, and in challenging times making a little bit of headway can lead to a cascading effect. It can, if you keep the momentum.

And, in line with “authentic leadership,” it’s okay to admit that you don’t have the answers, that you might not even know the questions to ask. But doing nothing, or operating in a “business as usual” way won’t make your company stronger, won’t open up new opportunities, won’t generate new ideas, and won’t sit well with your employees, who are very much thinking about these issues. 

So, in today’s challenging times I would follow my own advice, be thoughtful and reflective, and intentional in searching for common solutions.  I’d try to avoid “mob mentality” pressure — but I would also be listening carefully to my stakeholders and to my own conscience.

In the coming weeks, I’ll write posts that get into some of the other topics I cover in the book, but none of them will be as good as reading the full thing!

My latest book (I’m a co-author along with Brad Feld and Mahendra Ramsinghani), Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, is now live on Amazon – today is publication day! The book is a major refresh of the first edition, now eight years old. I was quoted in it extensively but not an official author – Brad and Mahendra were nice enough to share that with me this time. The book includes a lot of new material and new voices, including a great Foreword by Jocelyn Mangan from Him for Her and Illumyn. It’s aligned with Startup CEO and Startup CXO in look and in format and is designed to be an easy-to-read operator’s manual to private company boards of directors. Brad also blogged about it here.

We’ve done a lot of work around startup boards at Bolster the past couple of years, including working with over 30 CEOs to help them hire amazing new independent board members. Our landmark Board Benchmark study last year highlighted the problem with startup boards, but also the opportunity that lies within: not enough diversity on the boards, but also not nearly enough independent directors — and a lot of open seats for independent directors that could be filled. That conclusion led me to my Startup Board Mantra of 1-1-1: Independent directors from Day 1, 1 member of the management team, and 1 independent for every 1 investor.

As we posted on the Bolster blog last week, our quick refresh of the Board Benchmark study revealed some good news and some bad news about progress on diversity in the boardroom with startups. The good news is that the needle is starting to move very slowly, and that independent directors present the best opportunity to add diversity to boards. Our data shows that half of all new directors brought onto boards in the last year were independents, and of those, 57.9% were women and 31.6% were non-White board members. Those numbers are well above the prior study’s benchmarks of 36% and 23%, respectively (our experience running board searches skews even further to women and non-White directors being hired).

The bad news is how slowly the needle is moving — only 20% of open independent board seats were filled over the previous year, which is a lot of missed opportunity. The main takeaway is that while overall representation on boards is still skewed largely White and male, the demographic profile of new board appointments looks a lot different from the representation on boards today, indicating that CEOs are making intentional changes to their board composition.

Startup boards are a great way to drive grassroots change to the face of leadership in corporate America. More CEOs need to follow up by filling their open board seats and fulfilling their stated desires to improve diversity in the boardroom. This takes time and prioritization — these are the places where we see board searches either never get off the ground, or falling down once they do, for all the searches we either run or pitch at Bolster.

Hopefully Startup Boards will help the startup ecosystem get there.

Doing Well by Doing Good, Part IV

This series of posts has mostly been about things that people or companies do that help make the world a better place — sometimes when it’s their core mission, other times (here and here) when it becomes an important supporting role at the company.

Today’s post is different — it’s actually a Book Short as well of a new book that’s coming out later this fall called Green to Gold:  How Smart Companies Use Environmental Strategy to Innovate, Create Value, and Build Competitive Advantage, published by Yale Press and written by Daniel Esty (a Yale professor and consultant), and a good friend of mine, Andrew Winston, a corporate sustainability consultant.

Green to Gold is a must-read for anyone who (a) holds a leadership position in business or is a business influencer, and (b) cares about the environment we live in.  Its subtitle really best describes the book, which is probably the first (or if not, certainly the best) documentation of successful corporate environmentalstrategy on the market.

It’s a little reminiscent to me of Collins Built to Last and Good to Great in that it is meticulously researched with a mix of company interviews/cooperation and empirical and investigative work.  It doesn’t have Collins “pairing” framework, but it doesn’t need to in order to make its point.

If you liked Al Gore’s movie, An Inconvenient Truth, this book will satisfy your thirst for information about what the heck the corporate world is doing or more important, can do, to do its part in not destroying our ecosystem.  If you didn’t like Gore’s movie or didn’t see it because you don’t like Al Gore or don’t think that many elements of the environmental movement are worthwhile, this book is an even more important read, as it brings the theoretical and scientific to the practical and treats sustainability as the corporate world must treat it in order to adopt it as a mainstream practice — as a driver of capitalistic profit and competitive advantage.

This is a really important work in terms of advancing the cause of corporate social responsibility as it applies to the environment.  Most important, it proves the axiom here that you can, in fact, Do Well by Doing Good.  If you’re interested, you can pre-order the book here.  Also, the authors are writing a companion blog which you can get to here.

I haven’t done a book review yet on this blog because I haven’t found a very relevant one. I will do more as I go here — I’ve actually read a few pretty useful business books lately — but there’s no better book to kick off a new category of postings here than the one I just finished: The MouseDriver Chronicles: The True-Life Adventures of Two First-Time Entrepreneurs.

The book details how two freshly-minted Wharton MBAs skipped the dot com and investment banking job offers to start a two-person company that produced the MouseDriver (a computer mouse shaped like a the head of a golf club) back in 1999-2000. It’s a great, quick read and really captures the spirit of much of what I’m trying to do with this blog, which is talk about first-time CEO issues, or company leadership/management issues in general.

Although it’s not about an internet business, the book also has an interesting side story, which is the powerful impact that email had on the MouseDriver business, with an email newsletter the entrepreneurs started that developed great readership and ultimately some viral marketing. Sort of like a blog, circa 1999.

Thanks to Stephanie Miller at Return Path for giving me the book!

It’s good that my friend Brad Feld‘s new book (co-authored by Dave Jilk, who I’ve also known on and off over the years), is divided into 52 chapters and is designed as a bit of a devotional, to be read one chapter per week.

Each chapter of The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors is, as the authors write in the Introduction, worth “chewing on a while.” The structure of the book is laid out as:

The book contains fifty-two individual chapters (one for each week) and is divided into five major sections (Strategy, Culture, Free Spirits, Leadership, and Tactics). Each chapter begins with a quote from one of Nietzsche’s works, using a public domain translation, followed by our own adaptation of the quote to 21st-century English. Next is a brief essay applying the quote to entrepreneurship. About two-thirds of the chapters include a narrative by or about an entrepreneur we know (or know of), telling a concrete story from their personal experience as it applies to the quote, the essay, or both.

That structure is perfect for me. I did ok in Philosophy classes, but I wouldn’t say it was my preferred subject. So the fact that Brad and Dave turned every Nietzsche quote into plain English before applying it to entrepreneurship and disruption was a welcome tactic to make the book as accessible as possible.

I wrote one of the essays in the book on creating a Company Operating System, which is in the chapter called “Doing is not Leading.” It’s an honor to be included as a contributor alongside a number of awesome CEOs, including Reid Hoffman, Ingrid Alongi, Daniel Benhammou, Sal Carcia, Ben Casnocha, Ralph Clark, David Cohen, Mat Ellis, Tim Enwall, Nicole Glaros, Will Herman, Mike Kail, Luke Kanies, Walter Knapp, Gary LaFever, Tracy Lawrence, Jenny Lawton, Seth Levine, Bart Lorang, David Mandell, Jason Mendelson, Tim Miller, Matt Munson, Ted Myerson, Bre Pettis, Laura Rich, Jacqueline Ros, and Jud Valeski.

In his Foreword, Reid Hoffman connects the dots perfectly:

Returning to Nietzsche, let’s examine why he in particular is such an apt patron philosopher for entrepreneurs. Nietzsche was rebelling against a stultifying philosophical practice that exalted the past—specifically the ideals and images of former thinkers and former leaders. He wanted to refocus on the now, on what humanity was and what it could become. As part of his rebellion, Nietzsche philosophized with a hammer: he wanted to destroy the old mindsets that locked people into the past, and thus better equip them to embrace the possibility of the new. Nietzsche’s desire to shift mindsets is also why he emphasized new styles of argument. Whereas most philosophers would typically open an argument in a classical form or by reviewing a historical great, Nietzsche would lead with an arresting aphorism or a completely new mythological narrative. He was, above all else, a disruptor of pieties and convention, always in search of new and original ways to be contrarian and right, never satisfied with the status quo. This is exactly the kind of mindset entrepreneurs should adopt. This is why a daily practice of philosophy can be the way that an entrepreneur moves from good to great. And, why a daily practice of Nietzsche is a great practice of philosophy for entrepreneurs.

What I love about the book is that you can read any given chapter at any time without having to read it front to back, and the combination of Nietzsche and entrepreneur essays makes the topics come to list. Pick one — they are organized into five sections, Strategy, Culture, Free Spirits, Leadership, and Tactics — and you’re sure to get both something chewy (e.g, thoughtful) and delicious (e.g., practical).

As part of the new section on Exits in the Second Edition of the book (order here), there’s a final chapter around you as CEO and thinking about what you do next.  I’ll start this post by saying, while am really happy with where I am now (more to come on that!), I am not happy with the way I handled my own “next steps” after the Return Path exit.  I did follow some of my own advice, but not enough of it.  I jumped back into the fray way too quickly.

Some exits leave CEOs in a position of never having to work again – those are good in that they give you more time to think about what’s next and more options for what’s next, but no financial forcing function to do anything.  Some CEOs want to work again in the same field, doing another startup or being hired to run a larger company or focusing on serving on boards and mentoring other CEOs.  Some want to transition to a different kind of work entirely.  

But no matter what your circumstances are, the most important thing you can do after selling your startup is to downshift and take time off.  You probably haven’t done that in years, maybe decades.  You may feel like you only have one gear – ON – but in fact, you can get into new patterns of life and take time to enjoy and appreciate things you may have neglected for years and do some of what Stephen Covey calls “Sharpen the saw.”  Here’s an excerpt from the book about this:

There’s more to thinking about your next step than just clearing your head, of course.  You have to spend some cycles being reflective about the journey you just went on.  Our senior team, including a couple long time alumni, gathered and did what I call the “ultimate post mortem,” reflecting on lessons learned over 20 years.  I spent some time thinking about how to tell my story, what my own narrative was about the journey.  And I came up with my framework for deciding what to do next – that checklist of the things I wanted and didn’t want in my next job, which is detailed in the book, and which I’ll talk about more in the weeks to come as we prepare for the public launch of our new company.  But for now, this is the final teaser post I’ll write about the Second Edition of Startup CEO:  A Field Guide to Scaling Up Your Business. Next week, though, I will write about the sequel my colleagues and I are writing at our new business.

• Not all successful CEOs are extroverts: Financial News – Yahoo! Finance
  Brad tipped me off to this article — it’s a good one and draws on a lot of the work and thinking done by Jim Collins in both Good to Great and Built to Last (links to both books on my blog in the books sidebar).
  (tags: Books Entrepreneur Management)

Alter Ego

A couple people have asked me recently how I work with an Executive Assistant, what value that person provides, and even questioned the value of having that position in the company in an era where almost everything can be done in self-service, lightweight ways. At my old company (in the 90s), each VP-level person and up had a dedicated assistant – the world certainly doesn’t require that level of support any more.  In our case, Andrea has other tasks for the company that take up about half of her time.

I happen to have the absolute best, world class role model assistant in Andrea, who I’ve had the pleasure of working with for almost seven years now (which is a reminder to me that she has a sabbatical coming up soon!).

This is an important topic.  It’s tempting for CEOs of startups, and even companies that are just out of the startup phase, to want to do it all themselves…or feel like they don’t need help on small tasks.  My argument against those viewpoints is that your time is your scarcest resource as the leader of an organization, and anything you can do to create more of it for yourself is worthwhile.  And a good assistant does just that – literally creates time for you by offloading hundreds of small things from your plate that sure, you could do, but now you don’t have to.

I asked Andrea to write up for me a list of the major things she does for me (although she didn’t realize it was going to turn into a blog post at the time).  I’ll add my notes after each bullet point in italics on the value this creates for me.

• Updates and maintains calendar, schedules meetings and greets visitors – My calendar is like a game of sudoku sometimes.  I can and do schedule my own things, but Andrea handles a lot of it.  She also has access to all my staff’s calendars so she can just move things around to optimize for all of us.  Finally, she and I review my calendar carefully, proactively, to make sure I’m spending my time where I want to spend it (see another item below)
• Answers and screens direct phone line – The bigger we get, the more vendors call me. I can’t possibly take another call from a wealth management person or a real estate broker.  Screening is key for this!
• Plans and coordinates company-wide meetings and events – This is an extension of managing my calendar and accessing other executives’ calendars…and a pretty key centralized function.
• Plans and coordinates Executive Committee offsite’s – Same, plus as part of my theme of “act like you’re the host of a big party,” I like this to be planned flawlessly, every detail attended to.  I do a lot of that work with Andrea, but I need a partner to drive it.
• Collects and maintains confidential data – Every assistant I’ve ever had starts by swearing an oath around confidentiality.
• Prepares materials for Board Meetings and Executive Committee meetings – Building Board Books is time consuming and great to be able to offload.  We put together the table of contents, then everyone pours materials into Andrea, and poof!  We have a book.  For staff meetings, she manages the standing agenda, changes to it, and the flow of information and materials so everyone has what they need when they need it to make these meetings productive from start to finish.  In our case, Andrea is part of the Executive Committee and joins all of our meetings so she is completely up to speed on what’s going on in the company – this really enables her to add value to our work.  She’s also not just a passive participant – some great ideas have come from her over the years!
• Coordinates and books travel (domestic and international) – Painful and time consuming, not because Expedia is hard to use but because there is a lot of change, complexity, and tight calendars to manage and coordinate for certain trips.  And while it takes a while to get an assistant up to speed on how you like to travel or how you think about travel, this is a big time saver.
• Prepares expense reports – Same thing – you CAN do it, but easier not to.
• Manages staff gifts and Anniversary presents for all employees – This is a big one for me.  I send every employee an anniversary gift each year and call them.  Once a month, a stack of things to sign magically appears on my desk…and then gets distributed.  Andrea manages the schedule, the inventory of gifts, the distribution of gifts to managers.
• Manages investor database – I assume someday we’ll have a system for this, but for now, IR is a function that Andrea coordinates for me and Jack, my CFO.
• Assist Executive Committee with project as needed – The person in this role for you ends up being really valuable to help anyone on your staff with major projects.  Good use of time.
• Prepares Quarterly Time Analysis for CEO – This is a big one for me.  Every quarter, Andrea downloads my calendar and classifies all of my time, then produces an analysis showing me where I’m spending time my classifications are – Internal, External, non-RP, free, travel, Board/Investor.  This really helps us plan out the next quarter so I’m intentional about where I put my hours, and then it helps her manage my calendar and balance incoming requests.
• Help with communications – This one was not on Andrea’s list, but I’m adding it.  She ends up drafting some things for me (sometimes as small as an email, sometimes as large as a presentation, though with a lot more guidance), which is helpful…it’s always easier to edit something than create it.  I also usually ask Andrea to read any emails I send to ALL ahead of time to make sure they make sense from someone’s perspective other than my own, and she’s very helpful in shaping things that way.

This may not be true of all companies at all sizes and stages, but for companies like ours, I’d classify a great assistant as a bit of an alter ego, one definition of which is “second self” – literally an extension of you as CEO.  That means the person is acting AS YOU, not just doing things FOR YOU.  Think about the transitive property here.  Everything you do as CEO is (in theory) to propel the whole company forward.  So everything your alter ego does is the same.  A great assistant isn’t just your administrative assistant.  A great assistant is an overall enabler of company success and productivity.  You do have to invest a lot of time in getting someone up to speed in this role for them to be effective, and you have to pay well for performance, but a great assistant can literally double your productivity as CEO.

Managing by Checklist

The Checklist Manifesto:  How to Get Things Right, started as an article in The New Yorker a few years ago by Atul Gawande and then turned into a book as well (book, Kindle).  I haven’t read the book; the story in the article is about life-and-death issues and how Intensive Care Units in hospitals work most successfully when they “manage by checklist” — they keep thousands of small steps performed by different people in order.

The story is very telling for business as well and reminiscent of David Allen’s productivity books, Getting Things Done: The Art of Stress-Free Productivity and Ready for Anything: 52 Productivity Principles for Work and Life. The reality as far as I’m concerned is that no matter who you are, no matter what role you play in an organization, my guess is that there are some routine or recurring tasks you perform where having a tight checklist is a no-brainer.  Between eliminating missed steps and increasing productivity by not having to reinvent the wheel…we may not be saving lives in dramatic fashion in most businesses, but we all have jobs to do and want to do them as well as possible.

Thanks to my colleague Tami Forman for pointing me to this.  At a minimum, the article is a great read.  And oddly, I had this post drafted for quite a while – I decided to post it today when I saw Jeff Ogden’s post about the same topic in reference to yesterday’s emergency landing at JFK.

A Little Quieter Than Usual, For Now

As many of you know, I’m writing a book called Startup CEO:  a Field Guide to Building and Running Your Company, which is due to the publisher in a few weeks.  I’d originally thought the book would be an easy project since the idea was to “turn my blog into a book.”  But then it turned out that for the book I wanted to write, I’d only written about 1/3 of the content on the blog already!

So the past few weeks I’ve been writing my brains out.  I now have a nearly 100,000 word draft, which needs to be edited down quite a bit, charts and tables inserted, outside contributors added in.

For the next handful of weeks, I’m going to post a bit less frequently than usual – probably every other week – as a result.  But once I get through this period, I’ll come roaring back with TONS of new content written for the book!

Blogiversary, Part VII

Today marks the seventh anniversary of OnlyOnce.  I haven’t marked the date with a post in three years, but here was my last such post (with links to prior posts in it).  In sum up until now, my reasons for blogging have been written up as:

• “Thinking” (writing short posts helps me crystallize my thinking)
• “Employees” (one of our senior people once called reading OnlyOnce “getting a peek inside Matt’s head)
• My book reviews help me crystallize my takeaways from books and serve as a bit of a personal reference library
• I like writing and don’t get to do it often

After seven years, though, I’m going to add another important point of value for me for writing OnlyOnce:  now, at 672 posts (including 27 that are scheduled but not yet posted – easy a record for me), this blog now serves as a repository for me of my own lessons learned, best practices, anecdotes, and aphorisms.  Thanks to Lijit, it’s easy for me and others to search.  Thanks to the new WordPress format and design by my friends at Slice of Lime, the categories and tagging make it much easier to navigate.

I probably get one question a week from a fellow CEO or prospective entrepreneur or employee that, instead of typing out an answer or setting up a meeting, I can actually just send a link as a starting point.  Sometimes there are follow-up questions, sometimes there aren’t.  But the blog is proving to be a very efficient form of documentation.