It’s election season, the GOP convention is literally in my backyard, and while this is not a political blog, I can’t help myself. As we as Americans grapple with the question of who we want to be our next leader (or at least those people who live in the 11 annointed swing states do), I have had a lot of thoughts lately about the question of what makes a good leader, and what the differences are between successful leadership in politics and successful leadership in business.

James O’Toole’s article on President Bush on page 31 of the September issue of Fast Company (no link available yet) brings up a really interesting point in comparing Bush to former president Ronald Reagan. He asserts that “what made Reagan effective and respected was that his actions followed consistently from a positive worldview.” (I’d also argue that the positive worldview as a starting point had something to do with it, but that’s beside the point.) He goes on to say that Bush has an “implementation problem” in that he “has vacillated between contradictory approaches to leadership: realism and idealism.” His central thesis is stated very clearly that

“Realists and idealists can both be effective leaders. But one cannot be both at once…The leadership lesson for GW – and for any leader – is simple: Followers don’t much care if leaders are realists or idealists, but they distrust inconsistency.”

This may or may not be true in the political arena, but I know it’s not true in business. Jim Collins’ watershed books Built to Last and Good to Great — both must reads! — describe the ideal CEO as someone who can simultaneously be optimistic and idealistic about the future of the company while simultaneously recognizing and dealing with the realities of the short-term situation. Ironically for this posting, Collins calls this the Stockdale paradox, after retired Admiral James Stockdale, a military leader and erstwhile vice presidential candidate of Ross Perot in the 1992 election.

As CEO, I have to constantly be selling the vision of the company — what we’re trying to become and how we’re going to get there — in broad strokes to my investors, board, management team, employees, and even customers. It’s that vision that keeps the whole machine running and keeps everyone focused and excited and working hard towards our long-term goals. But I have to be equally vigilant about the mundane realities of the current quarter, making our numbers, containing costs, and running the machine. If I did either one without the other, I think the whole system would break down.

Is Bush’s problem, as O’Toole asserts, that he articulated two different types of reasons for the war in Iraq — one rooted in Realism (WMD) and one rooted in Idealism (freedom and democracy)? Same goes for his states reasons for the tax cut — Realism on the one hand (to stimulate the economy) and Idealism on the other hand (shrink government). I agree that the Bush Administration has occasional implementation problems and doesn’t have nearly the “following” that Reagan and other more successful leaders in the past have, but I don’t think they’re caused by combining Realism and Idealism in the President’s leadership style. I think the leader of the free world has to do both well, each at its appropriate time, in order to be effective at his job.

Next up in this series: Admitting Mistakes.

(This is the sixth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, 4, and 5.)

As these posts have been running, a few people have asked me to quickly compare this experience to the experience of being a Startup CEO.  And that’s an interesting way to think about it. In a lot of ways, the couple of weeks of getting the IRT up and running felt like starting up a new business, only a lot more intense.  Following the outline of sections in Startup CEO:  a field guide to scaling up your business…

Part One: Storytelling.  The whole timeframe was super compressed.  It took us 2 days to be able to spend 4 hours writing our initial pitch deck defining scope, structure, and staffing request – and that was while we were working hard on our first two workstreams.  In a startup environment, that process would have taken much longer, involved more customer discovery and product/market fit research and spending 100% of our time on that. But then we got our “approval and funding” in about 45 minutes – that would have taken weeks and involved dozens of pitch meetings.  In terms of creating the organization’s Mission, Vision, and Values, we didn’t even bother, although I think it helped that the three of us were generally on the same page with how to work and that urgency was the essence of our job. The larger emergency operations team that we were more or less embedded in also had a very clear set of values and operating principles on display…although we didn’t actually go read them, I think they were in sync with our view of our team’s mission and principles.  In terms of “bringing our story to life,” that was wholly unnecessary!

Part Two: Building The Company’s Human Capital.  Like a startup, getting it right with the first handful of employees means everything.  In this case, the first two deputies on the team, handpicked by the Governor’s staff, were awesome and critical.  Bringing someone in from the private sector to run a public sector team only works when the rest of the team is incredibly knowledgeable about how the machinery of state government works.  And in the end, I think Sarah will be a better leader for the team than I was because she had a combination of private and public sector experience (and within her public sector experience, she had a lot of emergency response experience).  In general, the recruiting process was soooo different than private sector and public sector normally are. The first two team members handpicked the best people they knew in other relevant parts of the government. People were brought onto the team after one short phone call.  Other state departments heads loaned their people willingly. No such thing as a comp negotiation or a reference check. There were a bunch of other things under the “Human Capital” heading that are interesting notes/comparables as well. First, feedback in a compressed-timeframe emergency is something that you absolutely can’t skip – and you can’t wait for a formal process either.  Our team was pretty good about giving feedback at least daily in a semi-structured way as well as in the moment. We didn’t really have time to get into things like career pathing and compensation and firing. We did, after about 6 days at the suggestion of Kacey, our Chief of Staff, move the team to almost entirely remote (other than leadership and occasional critical meetings). This worked surprisingly well for a workforce probably unaccustomed to remote work.  The rest of the world is also learning how to do a lot of that now, too.

Part Three: Execution.  This whole experience was 97% execution.  In fact, we had a hard time finding time for things like strategy and planning because there was a crushing amount of work to do (welcome to emergency response), and a small team to do it.  We didn’t have to worry about raising money, budgeting, forecasting, reporting, and some of the other major execution steps in the private sector. We did do a good job of creating goals and milestones for our workstreams, but even that took a couple of weeks, and in retrospect, I wish we’d been able to do some of those sooner.  In terms of how our work got done, we were very conscious of creating daily meeting routines to structure our day and work – but there was no such thing as even a weekly meeting (let alone monthly strategics or quarterly offsites!), only daily meetings, multiple times per day. One thing that was interesting – I talk in the book about being deliberate and consistent with your platforms, especially around communication.  Channel proliferation is a real issue today (much more so than when I wrote the book), but we had an interesting mismatch at the beginning. The public sector team was used to email, text, and Google hangouts for comms. Nothing else. The private sector team used those things but was a lot more comfortable with Trello, Zoom, and Slack. Thank goodness both teams used G-Suite and not a mix of that and LiveOffice. But getting everyone on the team to converge on a couple systems is a work in progress and was messy, as evidenced in this great moment where Kacey was holding a laptop up to an actual whiteboard to show one of our private sector teams how she was thinking about something. 

Part Four: Building and Leading a Board of Directors.  This is kind of N/A, although the proxy for it in our case on the IRT was the leadership structure of the Emergency Operations Center and then the Governor and the part of his cabinet that was keyed into the emergency response.  In this regard, the main differences between the private sector and public sector were speed/formality (no room for formality when you’re meeting daily or at a moment’s notice!), and, interesting, the need for integration. A company reports to its board on how it’s doing.  This team had to use its “board” to make sure it was integrating with other state agencies and initiatives. In this way, the team functioned more like a business unit within a company than an actual company.

Part Five: Managing Yourself So You can Manage Others.  This was obviously critical…and obviously quite difficult.  And within the overall Emergency Operations Center (outside of our team, the real emergency professionals), there were people, including leaders, who were working 7 days/week for multiple weeks on end, and long days, too.  At one point, the EOC leader posted this note on the wall, and he frequently took time in daily briefings to encourage everyone to take a day or two off and take care of themselves physically.  He role-modeled that behavior as well. You can only run a sprint for so long. Once it becomes clear it’s a marathon, well, you know.

Stay tuned for the final post in the series tomorrow…

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).

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

I received in the mail yesterday (by overnight priority mail, no less), a 400+ page prospectus from Mittal, a Dutch company in which I apparently own a few shares of stock through a managed mutual fund I’m part of. This book was BIG – well over 2 inches thick and big enough to have a binding strip instead of staples. And it had enough legalese in it to put anyone to sleep.

What did I do with it? After ranting about how silly it was to ever print such a thing for mass push distribution to an audience that largely doesn’t care about it — straight into the trash. With a big thud, of course.

What a ridiculous waste. Why print it on paper at all? Make it available online via pdf. Email shareholders or send them a postcard or leave an automated voicemail and ask them if they want a hard copy. Figure out which shareholders are in a managed fund, and send a single copy to the fund manager, since the individuals don’t even know they’re shareholders or don’t make decisions about individual stocks in the fund. Do something that costs less and doesn’t destroy trees that 99% of people will never read.

Shame on Mittal and their bankers, proudly displayed on the cover of the book — Goldman Sachs, Citigroup Credit Suisse, HSBC and Societe General.

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)

Retaining good people has always been at the top of my list, even in the dark days.  But hiring and managing in an environment that’s once-stagnant-now-growing presents some real challenges.  Many of these aren’t unique to startups — it’s always tough to find A players — but there are three things I’ve observed that are uniquely tough about hiring in an entrepreneurial environment:

The Best Laid Plans, IV

I have had a bunch of good comments from readers about the three posts in this series about creating strategic plans (input phase, analysis phase, output phase).  Many of them are leading me to write a fourth post in the series, one about how to make sure the result of the plan isn’t shelfware, but flawless execution.

There’s a bit of middleware that has to happen between the completion of the strategic plan and the work getting done, and that is an operating plan.  In my observation over the years, this is where most companies explode.  They have good ideas and capable workers, just no cohesive way to organize and contextualize the work.  There are lots of different formats operating plans can take, and a variety of acronyms to go with the formats, that I’ve heard over the years.  No one of these formats is “right,” but I’ll share the key process steps my own team and I went through just over the past few months to turn our strategic planning into action plans, synchronizing our activities across products and groups.

• Theme:  we picked a theme for the year that generally held the bulk of the key work together – a bit of a rallying cry
• Initiatives:  recognizing that lots of people do lots of routine work, we organized a series of a dozen “move the ball forward” projects into specific initiatives
• Communication:  we unveiled the theme and the initiatives to ALL at our annual business meeting to get everyone’s head around the work to be done in the upcoming year
• Plans:  each of the dozen initiative teams, and then also each team/department in the company (they’re different) worked together to produce a short (1-3 page) plan on a template we created, with a mission statement, a list of direct and indirect participants, important milestones and metrics
• Synchronization:  the senior management team reviewed all the plans at the same time and had a meaningful discussion to synchronize the plans, making edits to both substance and timing
• Scorecard:  we built our company scorecard for the year to reflect “green/yellow/red” grading on each initiative and visually display the most important 5-6 metrics across all initiatives
• Ongoing reporting:  we will publish the scorecard and updated to each initiative plan quarterly to the whole company, when we update them for Board meetings

As I said, there’s no single recipe for success here, but this is a variant on what we’ve done consistently over the years at Return Path, and it seems to be working well for us.  I think that’s the end of this series, and judging from the comments I’ve received on the blog and via email, I’m glad this was useful to so many people.