Half the Benefit is in the Preparation

This past week, we had what has become an annual tradition for us – a two-day Board meeting that’s Board and senior management (usually offsite, not this year to keep costs down) and geared to recapping the prior year and planning out 2009 together.  Since we are now two companies, we did two of them back-to-back, one for Authentic Response and the other for Return Path.

It’s a little exhausting to do these meetings, and it’s 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 off the high dive for another year.

The most exhausting part is probably the preparation for the meetings.  We probably send out over 400 pages of material in advance – binders, tabs, the works.  It’s the only eco-unfriendly Board packet of the year.  It feels like the old days in management consulting.  It takes days of intense preparation — meetings, spreadsheets, powerpoints, occasionally even some soul searching — to get the books right.  And then, once those are out (the week before the meeting), we spend almost as much time getting the presentations down for the actual meeting, since presenting 400 pages of material that people have already read is completely useless.

By the end of the meetings, we’re in good shape for the next year.  But before the meetings have even started, we’ve gotten a huge percentage of the benefit out of the process.  Pulling materials together is one thing, but figuring out how to craft the overall story (then each piece of it in 10-15 minutes or less) for a semi-external audience is something entirely different.  That’s where the rubber meets the road and where good executives are able to step back; remember what the core drivers and critical success factors are; separate the laundry list of tactics from the kernel that includes strategy, development of competitive advantage, and value creation; and then articulate it quickly, crisply, and convincingly. 

I’m incredibly proud of how both management teams drove the process this year – and I’m charged up for a great 2009 (economy be damned!).

Book short:  Life Isn’t Just a Wiki

One of the best things I can say about Remote: Office Not Required,  by Jason Fried and David Heinemeier Hansson, is that it was short.  That sounds a little harsh – part of what I mean is that business books are usually WAY TOO LONG to make their point, and this one was blessedly short.  But the book was also a little bit of an angry rant against bad management wrapped inside some otherwise good points about remote management.

The book was a particularly interesting read juxtaposed against Simon Sinek’s Leaders Eat Last which I just finished recently and blogged about here, which stressed the importance of face-to-face and in-person contact in order for leaders to most effectively do their jobs and stay in touch with the needs of their organizations.

The authors of Remote, who run a relatively small (and really good) engineering-oriented company, have a bit of an extreme point of view that has worked really well for their company but which, at best, needs to be adapted for companies of other sizes, other employee types, and other cultures.  That said, the flip side of their views, which is the “everyone must be at their cubicle from 9 to 5 each day,” is even dumber for most businesses these days.  As usual with these things, the right answer is probably somewhere in between the extremes, and I was reminded of the African proverb, “If you want to go fast, go alone. If you want to go farm go together” when I read it.  Different target outcomes, different paths.

I totally agree with the authors around their comments about trusting employees and “the work is what matters.”  And we have a ton of flexibility in our work at Return Path.  With 400 people in the company, I personally spend six weeks over the summer working largely remote, and I value that time quite a bit.  But I couldn’t do it all the time.  We humans learn from each other better and treat each other better when we look at each other face to face.  That’s why, with the amount of remote work we do, we strongly encourage the use of any form of video conferencing at all times.  The importance of what the authors dismiss as “the last 1 or 2% of high fidelity” quality to the conversation is critical.  Being in person is not just about firing and hiring and occasional sync up, it’s about managing performance and building relationships.

Remote might have been better if the authors had stressed the value that they get out of their approach more than ranting against the approaches of others.  While there are serious benefits of remote work in terms of cost and individual productivity (particularly in maker roles), there are serious penalties to too much of it as well in terms of travel, communication burden, misunderstandings, and isolation.  It’s not for everyone.

Thanks to my colleague Hoon Park for recommending this to me.  When I asked Hoon what his main takeaway from the book was, he replied:

The importance of open communication that is archived (thus searchable), accessible (transparent and open to others) and asynchronous (doesn’t require people to be in the same place or even the same “timespace”).  I love the asynchronous communication that the teams in Austin have tried: chatrooms, email lists (that anyone can subscribe to or read the archives of), SaaS project management tools. Others I would love to try or take more advantage of include internal blogs (specifically the P2 and upcoming O2 WordPress themes; http://ma.tt/2009/05/how-p2-changed-automattic/), GitHub pull requests (even for non-code) and a simple wiki.

These are great points, and good examples of the kinds of systems and processes you need to have in place to facilitate high quality, high volume remote work.

We have a little more than two weeks of The Daily Bolster podcast under our belts now, and we’re off to a great start! I announced it here, and I thought I’d post links to the first bunch of episodes…I don’t think I’ll do this regularly, though. You can listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications.

Episode 1: 3 Tips to Scale Your Culture with Nick Mehta

Our very first guest on The Daily Bolster was Nick Mehta, CEO of Gainsight. As an early-stage startup or a small business, you have significant influence over the culture—but what happens when you’re one of many? Nick and I discussed what happens to company culture when you achieve your scaling and growth goals.

Episode 2: Managing Up with Cristina Miller

Executives are often caught in the middle of the leadership dynamic, managing both up and down the organization. Cristina Miller—a seasoned, results-driven executive and board member (including on Bolster’s board!) with a strong track record—shared what it looks like to set expectations and build a strong relationship with your CEO.

Episode 3: Common Mistakes Founders Make with Fred Wilson

Fred Wilson has been a venture capitalist since 1987 and has worked with me for over 20 years now—so it’s fair to say he’s witnessed a few founders and become familiar with their most common mistakes. Listen to this episode to learn how to recognize and avoid those mistakes for yourself.

Episode 4: Cultivating Talent to Promote Internally with Nick Francis

In this episode, Nick Francis—co-founder and CEO of Help Scout—joins me to discuss what it takes to cultivate in-house talent and embody organizational values. I talk about my playbook for building effective teams and developing leaders with a growth mentality as part of this.

Episode 5: Deep Dive with Jeff Epstein

Career shifts are more common now than ever, even for senior executives. Experienced CFO and operator (and one of my former board members) Jeff Epstein joined me for an extended episode about the ins and outs of career transitions and the surprises that come with them, from role changes to new industries to vastly different organizational structures. Tune in to follow the shifts in Jeff’s career journey, hear about the lessons he learned firsthand, and get his advice for founders looking to scale. “I always wanted to develop a circle of competence and then over time expand the circle,” Jeff says. “You just learn more.”

Episode 6: Hallmarks of Successful Founders with David Cohen

David Cohen, Founder and Chairman at Techstars, shares the top three signs he looks for that differentiate successful founders—things that are nearly impossible to fake. Either you have them, or you don’t. This one is awesome.

Episode 7: Success as a Fractional Exec with Courtney Graeber

If you know anything about Bolster, you know we’re a champion for fractional executives. As an Interim Chief People Officer, HR Executive Consultant, and trusted mentor to executive teams, Courtney Graeber provides feedback and recommendations that enhance organizational culture and attract, develop, and retain top talent. Many of her clients are navigating transitional periods—and that’s where Courtney’s expertise comes in. Listen in to learn what it’s like to be (or work with) a fractional head of people.

Episode 8: 3 Ways VCs Say “No” Without Saying “No” with Jenny Fielding

It’s important for founders to be able to hear what’s left unsaid in conversations with VCs. Sometimes, says one of NYC’s top pre-seed investors Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either.  Here, Jenny shares three signs a VC may be saying “no” without saying the words—and what founders should do next.

Episode 9: Building a Strong Culture with Jailany Thiaw

Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines, joins me to discuss the best ways to get company buy-in as you build and maintain a strong and welcoming culture—especially in an early stage or remote environment.

Episode 10: Deep Dive with Brad Feld

Brad Feld is partner and co-founder of Foundry, and a long time early stage investor and entrepreneur who I’ve also worked with for more than two decades. In this episode, he and I take a deep dive into how startups and venture capital have changed over the past 25 years—and what has stayed the same.  They also discuss the dynamics of startup boards, along with common characteristics that make founders or companies successful at scale.

Episode 11: The Value of Podcasting with Lindsay Tjepkema

This episode is all about podcasting. Meta, right? Lindsay Tjepkema is the CEO and co-founder of Casted, the podcasting solution for B2B marketers.  She and I dive into the reasons why podcasts are such a great way to get your voice—literally—out into the world. Tune in to hear Lindsay’s tips for starting a podcast as a CEO, setting expectations, asking meaningful questions, and creating human connection. We’ve loved partnering with Lindsay and her team so far on The Daily Bolster!

Episode 12: Interviewing for “Culture Fit” with Rory Verrett

What does it mean to interview for culture fit? How should CEOs and leaders go about doing it—and is there a better way? Rory Verrett is the founder and managing partner of Protégé Search, the leading retained search and leadership advisory firm focused on diverse talent, and is also on Bolster’s Board of Directors. He and I discuss why CEOs are not always the best arbiters of company culture, then we dive into what it means to look for specific values throughout the interview process, rather than the vague concept of a culture fit.

The Daily Bolster is for people in the startup world want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed. Instead, we’re getting straight to the point with mostly 5-minute episodes. Any and all feedback welcome!

My long-time friend and former Board member Brad Feld has become a prolific writer on the startup world over the years and is the person (other than me) most responsible for me getting into that scene as well. Startup CEO is part of his Startup Revolution series, which followed me writing an essay for Do More Faster, and then writing a series of sidebars call “The Entrepreneur’s Perspective” in Venture Deals.

All Brad’s books are listed here. If you’re in the startup universe, I’d encourage you to read all of them. I’m excited to dive into his newest book, The Startup Community Way, which comes out this week from our same publisher, John Wiley & Sons. I’ve gotten part of the way through an early copy, and I love it already.

The approach Brad and his co-author Ian Hathaway take is to evolve their Boulder Thesis from the original Startup Communities book. They dive into the topic and examine it from the perspective of a complex system, which of course anything as fragmented as an ecosystem of public, private, and academic organizations is.

The book — and the whole topic, quite frankly — remind me of a great management book I read several years ago by General Stanley McChrystal called Team of Teams. Organizations have gotten more complex and have had to adapt their structures, and the most successful ones are the ones that have shifted from hierarchical structures to node-based structures, or teams of teams, where individual, agile teams operate with loose points of connection to other teams that focus on dependencies and outcomes.

In the same way, startup communities and the broader ecosystems that touch them have changed and adapted, and the successful ones have learned how to stay loosely connected to other startup communities, prioritize collaboration, and remain focused on inclusion and entrepreneurial leadership.

Book Short:  Best Book Ever

The Hard Thing About Hard Things, by Ben Horowitz, is the best business book I’ve ever read.  Or at least the best book on management and leadership that I’ve ever read.  Period.

It’s certainly the best CEO book on the market.  It’s about 1000 times better than my book although my book is intended to be different in several ways.  I suppose they’re complementary, but if you only had time left on this planet for one book, read Ben’s first.

I’m not even going to get into specifics on it, other than that Ben does a great job of telling the LoudCloud/Opsware story in a way that shows the grit, psychology, and pain of being an entrepreneur in a way that, for me, has previously only existed in my head.

Just go buy and read the book.

Book Short:  The Little Engine that Could

Authors Steven Woods and Alex Shootman would make Watty Piper proud.  Instead of bringing toys to the children on the other side of the mountain, though, this engine brings revenue into your company.  If you run a SaaS business, or really if you run any B2B business, Revenue Engine:  Why Revenue Performance Management is the Next Frontier of Competitive Advantage, will change the way you think about Sales and Marketing. The authors, who were CTO and CRO of Eloqua (the largest SaaS player in the demand management software space that recently got acquired by Oracle), are thought leaders in the field, and the wisdom of the book reflects that.

The book chronicles the contemporary corporate buying process and shows that it has become increasingly like the consumer buying process in recent years.  The Consumer Decision Journey, first published by McKinsey in 2009, chronicles this process and talks about how the traditional funnel has been transformed by the availability of information and social media on the Internet.  Revenue Engine moves this concept to a B2B setting and examines how Marketing and Sales are no longer two separate departments, but stewards of a combined process that requires holistic analysis, investment decisions, and management attention.

In particular, the book does a good job of highlighting new stages in the buying process and the imperatives and metrics associated with getting this “new funnel” right.  One that resonated particularly strongly with me was the importance of consistent and clean data, which is hard but critical!  As my colleague Matt Spielman pointed out when we were discussing the book, the one area of the consumer journey that Revenue Engine leaves is out is Advocacy, which is essential for influencing the purchase process in a B2B environment as well.

One thing I didn’t love about the book is that it’s a little more theoretical than practical. There aren’t nearly enough detailed examples.  In fact, the book itself says it’s “a framework, not an answer.”  So you’ll be left wanting a bit more and needing to do a bit more work on your own to translate the wisdom to your reality, but you’ll have a great jumping off point.

Book Short: Not About Going With The…

Flow: The Psychology of Optimal Experience, by Mihaly Csikszentmihalyi (book, Kindle), was a great read and a nice change from either strictly business books or my regular fiction/non-fiction reading. It’s basically about the process of achieving happiness through control over one’s inner life, but it’s far from a self-help book. It’s almost more of practical psychology deep dive into what brings about happiness and peak performance – a state the author calls Flow but others have called other things over time, like being “in the zone.”

The author talks about achieving this control as synonymous with the enviable ability to persevere despite obstacles and setbacks and transform hopeless situations into challenges to be overcome, just through the force of personality. This ability comes directly from ways to order consciousness so as to be in control of feelings and thoughts. The normal entropy/chaos of the mind is the enemy. There were a few key moments or takeaways in the book for me.

1. When one’s experience is most positive – when one is achieving Flow – people cite the following conditions in this order of importance:

– Confront tasks we have a chance of completing

– Able to concentrate

– Concentration is possible because the task has clear goals and…

– …provides immediate feedback

– Act with a deep but effortless involvement that removes from awareness the worries and frustrations of everyday life

– Exercise a sense of control over actions

– Concern for the self disappears, yet paradoxically the sense of self emerges stronger after the experience is over

2. Becoming more Autotelic – learning how to make experiences ends in and of themselves – coming from the Greek words for “self” and “goal,” this concept is savoring a given activity for its own sake, NOT for its consequences and is a key to achieving Flow. Whether you create a mental construct around beating a personal record, doing math or pattern matching in your head, or something else, being able to focus enough energy on the task at hand and not be distracted by the world around (present or future) is key. It’s a little like what I wrote a few months ago about how achieving mental discipline in the small areas of one’s life can lead to much greater things by building confidence and clearing mental clutter.

3. The concept of the “Flow channel” – as skill increases, challenges must also increase proportionally in order for us to continue learning, growing, and excelling – and achieving Flow.

4. Transformational coping is the ability to cheat chaos – transforming a hopeless situation into a new flow activity that can be controlled and enjoyed and emerge stronger from…

– Unselfconscious self-assurance – ego absent but confident, not at odds with environment but part of it

– Focusing attention on the world – looking outward, not inward

– The discovery of new solutions – being able to perceive unexpected opportunities as a result

5. How to develop the autotelic self

– Set clear goals

– Become immersed in the activity

– Pay attention to what’s happening

– Learn to enjoy immediate experience

The book reminded me of a couple other things I’ve read, in case any of these resonate with you. First, Tim Gallwey’s “Inner Game” books where he talks about “relaxed concentration,” basically the Flow state, and the inner conflict between focus on the event and focus on the consequences, between mental chaos and mental discipline, personified as Self 1 and Self 2. If you haven’t read these, any are good and give you the general idea, depending on which piques your interest the most: The Inner Game of Golf (book, Kindle), The Inner Game of Tennis (book only), and The Inner Game of Work (book, Kindle). Second, David Allen’s Getting Things Done theory about how a clear, uncluttered mind can do its best work. As Flow says, achieving an ordered mental condition is difficult – unless a person knows how to give order to his or her thoughts, attention will be attracted to whatever is most problematic at the moment.

I’m not sure this book short does the book justice. It’s pretty complex and is rich with examples, but Flow (book, Kindle) is well worth a read if you’re into the theory of self control leading to better results and more happiness in life. Thanks to my friend Jonathan Shapiro for this book.

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

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

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

What’s the zoom version of this?

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

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

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

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

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

Book Short: The Anti-Level-5 Leader

The Five Temptations of a CEO, another short leadership fable in a series by Patrick Lencioni, wasn’t as meaningful to me as the last one I read, The Four Obsessions of an Extraordinary Executive (post, link), but it wasn’t bad and was also a quick read.

The book to me was the 30 minute version of all the Level-5 Leadership stuff that Collins wrote about in Good to Great and Built to Last. All that said, it was a good quick read and a reminder of what not to do. The temptations are things that most CEOs I’ve ever known (present company very much included) have at least succumbed to at one point or another in their career. That said, you as a CEO should quit or be fired if you have them in earnest, so hopefully if you do have them, you recognize it and have them in diminishing quantities with experience, and hopefully not all at once:

– The temptation to be concerned about his or her image above company results

– The temptation to want to be popular with his or her direct reports above holding them accountable for results

– The temptation to ensure that decisions are correct, even if that means not making a decision on limited information when one is needed

– The temptation to find harmony on one’s staff rather than have productive conflict, discussion, and debate

– The temptation to avoid vulnerability and trust in one’s staff

I’m still going to read the others in Lencioni’s series as well. They may not be the best business books ever written, but they’re solid B/B+s, and they’re short and simple, which few business books are and all should be!

Book Short:  Crazy Eights

In honor of Return Path being in the midst of its eighth year, I recently read a pair of books with 8 in the title (ok, I would have read them anyway, but that made for a convenient criterion when selecting out of my very large “to read” pile).

Ram Charan’s latest, Know-How:  The 8 Skills That Separate People People Who Perform From Those Who Don’t, was pretty good and classic Charan.  Quick, easy to skim and still get the main points.  The book lost a little credibility with me when Charan lionized Verizon (perhaps he uses a different carrier himself) and Bob Nardelli (the book was published before Nardelli’s high profile dismissal), but makes good points nonetheless.  Some of the 8 Skills he talks about are what you’d expect on the soft side of leadership — building the team, understanding the social system, judging people — but his best examples were particularly actionable around positioning, goal setting, and setting priorities.  The book reminded me much more of Execution and much less of Confronting Reality (which is a good thing).

For years I’ve felt like the last person around to still not have read The 7 Habits of Highly Effective People, so I thought I’d skip straight to the punchline and read Stephen Covey’s newer book, The 8th Habit:  From Effectiveness to Greatness.  Fortunately, as I’d hoped, the new book summarizes the prior book several times over, so if you haven’t read the first, you could certainly just start with this one.  The book also comes with a DVD of 16 short films, some of which are great — both inspirational and poignant.  Unlike most business books, the 8th Habit is NOT skimmable.  It almost has too much material in it and could probably be read multiple times or at least in smaller pieces.  The actual 8th habit Covey talks about is what he calls Find Your Voice and Help Others Find Their Voices and is a great encapsulation of what leading a knowledge worker business is all about.  But the book is much deeper and richer than that in its many models and frameworks and examples/tie-ins to business and goes beyond the “touchy feely” into hard-nosed topics around execution and strategy.

Now I’m looking for the DVD of the first season of Eight is Enough!

Book Short:  Tales of Two Cities

Return Path is basically dual-headquartered in New York City and Broomfield, Colorado, so two recently published books which provide history and insights into the tech industry in those two cities were both of interest to me.

Startup Communities: Building an Entrepreneurial Ecosystem in Your City, by Brad Feld (book, kindle) came out a few months ago and is part of Brad’s Startup Revolution series which will also include my upcoming book Startup CEO, to be published this fall.  In the book, Brad uses the example of the Boulder/Denver area and a few different sectors to demonstrate a blueprint to creating an entrepreneurial ecosystem – the kind that are popping up all over the world of late.

Tech and the City: The Making of New York’s Startup Community, by Alessandro Piol (kindle only) hits on many of the same themes and topics as they relate to New York City, although the book is more of a history of the New York tech scene than a framework with examples.  The book draws heavily on quotes from Fred Wilson, like Brad, a long time friend and Board member.  One of the things the book left me thinking about was what the New York tech scene will look like in 30 years after the new Cornell-Technion campus is up and running.  That plus the current momentum of the tech industry in New York, plus the sheer commercial scale of the city, could really produce an interesting environment down the road that actually starts to rival Silicon Valley, though rival probably isn’t the right word.

All in, these two books do a good job of chronicling the industry I work in, in the two cities where I work, but they also abstract nicely to broader principles about public-private collaboration as well as sector development.