It feels as if almost everyone in our industry has read the famous Netflix culture deck on Slideshare, and with over 5mm views, that may not be too far off.  If you haven’t looked at it before, and if you care about your organization’s culture and how productive and happy employees are the best kind of employees, then take the time to flip through it.

As part of a benchmarking exercise we did on employers with unique and best HR/People practices a few years ago, a few of us did either site visits or at least live interviews with leaders at four companies, all of whom are pretty well known for progressive People practices that are also in-line with our company’s culture:  Morningstar, Gore, Nucor, and Netflix.  As part of this, we met in person with Patty McCord, Netflix’s long-time head of People.  It was a really informative meeting.

Now Patty has written a longform article in Harvard Business Review that shares a lot of what we learned from her in her office that day. It’s absolutely worth a read.  Netflix does have a pretty distinct culture and gets positive but mixed reviews on Glassdoor, so as with everything, I’m not advocating adopting everything they do lock, stock, and barrel.  But I can guarantee that some of the lessons that Patty shares are valuable no matter what your company is like.

(Written by both my Bolster co-founder Cathy Hawley and me)

I’ve attended two remote conferences, which Cathy dubbed “Zoomsites” — one here at Bolster and the Foundry Group CEO Summit.  Both hold interesting lessons for how these kinds of events can work well.

We founded Bolster two months into the COVID-19 pandemic, and our founding team had not met in person after 6 months of working together. Now, luckily, we’ve all worked together for many years, so we have a lot of trust built up, and have a very strong operating system which includes full team daily standups. Still, nothing beats face-to-face interaction. If you’ve ever founded a startup, you know how impactful it can be to work side by side, bounce ideas off each other, and collaborate as you learn more about opportunities and challenges in your market. 

We also have a strong belief in the power of the team, and the need to work together to ensure that we are aligned on all aspects of the business. And, we had a successful launch, with more interest in our marketplace than we had anticipated, so we knew we needed to step back to have a planning and strategy session.

We’ve done many executive offsites, and couldn’t imagine having an impactful offsite remotely, and we all agreed that we would be comfortable meeting up in person. So we started planning a 2-day offsite together in New York. Unfortunately, it turned out visitors to NY from Colorado and Indiana, the two states we were traveling from, needed to quarantine for 10 days when they got to NY. While technically we could get around this because we weren’t staying for 10 days, we decided to follow the spirit of the rules, and cancel our travel.

Since we really needed to have the planning and strategy session, and we’d blocked the two full days on our calendars, we decided to test out a ‘zoomsite’ – an all-remote video call. We modified the agenda a little – some things good in person fall flat on video. We knew we wanted to have really engaging conversations, and keep the agenda moving along, so that all eight of us could fully participate and complete the necessary work. I’m happy to say that we came out of the offsite with a revised strategic plan, new six-month goals set, and owners for each of the different workstreams. And, we had fun. Success!

The Foundry Group CEO Summit has been a different animal — it’s wrapping up today, but there’s been enough of it so far this week to comment on.  Foundry took a regular annual event with a large group (50-75) and moved it online.  They did a great job of adapting to the medium, spreading the event out with a few hours a day over multiple days to avoid Zoom fatigue and optimize attendance; scheduling content in shorter bursts than usual; making good use of breakout room technology; and encouraging heavy use of Zoom’s chat feature during sessions to make it as interactive as possible.  Like the Bolster event, there were some elements missing — all the great “hallway conversations” you have at in-person conferences where people are staying in the same hotel and seeing each other at meals, in the gym, between sessions, etc.  But it has also been a big success with enough community elements to make it worthwhile. 

Want to have a Zoomsite? Here are some tips:

• Make sure you have the tools needed for each activity. When you are brainstorming in person, you may use sticky notes or flip charts to write on. Remotely, you can use Google Docs or Sheets or tools like Note.ly or Miro
• Prep the sheets or docs ahead of time, so that people can engage in the activities easily. At our Zoomsite, we modified our blue-sky brainstorm session so that we each answered a few questions in a Google Sheet. We had a separate section for each person, and the exercise was easy to understand and engage in, and people got straight to work.
• Schedule in more breaks, shorter sessions, or less than full-day meetings. We had a couple of hour-long breaks during the day, which helped people to focus.  Foundry did a great job of getting everyone’s attention for a few hours every day, for more days than a normal in-person conference
• Plan your technology. At the Bolster meeting, we learned this the hard way. We tested out the idea of doing a “walk and talk” session where we’d each walk in our neighborhoods, and have a couple of strategic conversations just on the phone. Unfortunately, the technology didn’t work for everyone, as they hadn’t all used Zoom on their phones before, it was windy in some locations, and cell service dropped people from time to time.  Probably not the best idea we had!
• Include a social component. We were a little skeptical about this at the Bolster Zoomsite, but we’d always incorporated social time into offsites, and we really value connecting as people, not just as professionals, so we gave it a try. On the second day of our Zoomsite, we took a 2 hour break at the end of the day, and came back for drinks and dinner together. We had personal conversations, including sharing our favorite tv shows. Eight people on video eating together might sound odd, and we weren’t sure if it would work, but we all agreed that it was fun, and we’d do it again.  I missed the Foundry “Virtual Fun” session, but they did a virtual game show run by our sister portfolio company, Two-Bit Circus (and also had investigated Jack Box Games as another option for virtual games via Zoom screen share plus real-time voting and other engagement via phone).  I heard that session was great and engaging from people who attended

We all hope life returns to some kind of normal in 2021, though it’s unclear when that will be.  And there’s definitely value to doing meetings like this in person, but at least we now know that we can have a successful remote offsite or larger conference event.  As with everything, it will be interesting to see how the world is changed by COVID.  Maybe events like this will figure out how to mix remote and in-person participation, or alternate between event formats to keep travel costs down.

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

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

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

You can see the full list of blog posts here:

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

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

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

Techstars Roundup:  Why I Mentor Other Entrepreneurs

Yesterday was Demo/Investor day at Techstars in Boulder, Colorado.  A lot of people have written about it – Fred, Brad, and a great piece by Don Dodge on TechCrunch listing out all the companies.  My colleague George and I co-mentored two of the companies, SendGrid and Mailana, and we really enjoyed working with Isaac and Pete, the two entrepreneurs.

I posted twice earlier this summer on the TechStars experience.  My first post on this, Where do you Start?, was about whether to be methodical in business planning for a startup or dive right into the details.  My second post, One Pitfall to Avoid, was about making sure you don’t create a whizzy solution looking for a problem, but that you start with a problem that needs solving.

Rather than rehash what others have written about yesterday — yes, it was great and fun and energizing — I thought I’d focus on why I spend time mentoring new entrepreneurs.  I did it this year at TechStars, but I’ve done this informally for probably a dozen different entrepreneurs over the years in the community in general. 

Anyway, there are four main reasons I spend time mentoring other entrepreneurs (in no particular order):

It sharpens the saw.  This is Stephen Covey’s language from both The 7 Habits of Highly Effective People and The 8th Habit:  From Effectiveness to Greatness, and it simply refers to an activity that puls you out of the day to day and refreshes your brain because it’s different.  Running, playing guitar, mentoring sessions with entrepreneurs — they all clear the head and are just plain fun.

I get good specific ideas for my own business.  I think I came away from every single meeting I had with either entrepreneur this year with at least one new “to do” for myself and my team at Return Path.  There’s nothing quite like seeing how another company or entrepreneur operates to spur on good thinking, and in this case, both teams we worked with were working in the email space, so they were very relevant to our day-to-day.

I crystallize my own thoughts and ideas.  Much like writing this blog, problem/solution sessions with other entrepreneurs forces me to take a cloud of ideas down to a simple sentence or paragraph. 

I learn a lot about my colleagues.  This is a specific case for this year because I co-mentored these companies with George, although I guess bits and pieces of it have come up over the years as I’ve roped other colleauges into other situations.  George and I brought different ideas and frames of reference to our sessions with SendGrid and Mailana, and it was fun for me and a good learning experience as well to see how George approached the same problems I did.  Call it a “peek inside George’s brain.”

Hopefully I will get invited back to TechStars again next year as a mentor – it was great fun, and I’m incredibly proud of Pete and Isaac and their teams with how well they presented their companies yesterday!

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!

Everything That is New is Old

With a full nod to my colleague Jack Sinclair for the title and concept here…we were having a little debate over email this morning about the value of web applications vs. Microsoft (perhaps inspired by Fred, Brad, and Andy’s comments lately around Microsoft vs. Apple).

Jack and his inner-CFO is looking for a less expensive way of running the business than having to buy full packages of Office for every employee to have many of them use 3% of the functionality.  He is also even more of a geek than I am.

I am concerned about being able to work effectively offline, which is something I do a lot.  So I worry about web applications as the basis for everything we do here.  We just launched a new internal web app last week for our 360 review process, and while it’s great, I couldn’t work on it on a plane recently as I’d wanted to.

Anyway, the net of the debate is that Jack pointed me to Google Gears, in beta for only a month now, as a way of enabling offline work on web applications.  It clearly has a way to go, and it’s unclear to me from a quick scan of what’s up on the web site whether or not the web app has to enable Gears or it’s purely user-driven, but in any case, it’s a great and very needed piece of functionality as we move towards a web-centric world.

But it reminded of me of an application that I used probably 10-12 years ago called WebWhacker (which still exists, now part of Blue Squirrel) that enables offline reading of static web pages and even knows how to go to different layers of depth in terms of following links.  I used to use it to download content sites before going on a plane.  And while I’m sure Google Gears will get it 1000x better and make it free and integrated, there’s our theme — Everything That is New is Old.

The iPhone?  Look at Fred’s picture of his decade old Newton (and marvel at how big it is).

Facebook?  Anyone remember TheSquare.com?

MySpace?  Geocities/Tripod.

LinkedIn?  GoodContacts.

Salesforce.com?  Siebel meets Goldmine/Act.

Google Spreadsheets?  Where to begin…Excel…Lotus 123…Quattro Pro…Visicalc/Supercalc.

RSS feeds?  Pointcast was the push precursor.

Or as Brad frequently says, derive your online business model (or at least explain it to investors) as the analog analog.  How does what you are trying to online compare to a similar process or problem/solution pair in the offline world?

There are, of course, lots of bold, new business ideas out there.  But many successful products in life aren’t version 1 or even version 3 — they’re a new and better adaptation of something that some other visionary has tried and failed at for whatever reason years before (technology not ready, market not ready, etc.).

Only Twice? or The Un-Big Sur Marathon

Well, it wasn’t pretty, but Brad and I finished the 36th running of the New York City Marathon yesterday.  Here we are shortly after the end.

This was my second marathon.  When I finished Big Sur in 1996 with my friend Karl Florida, I had a nagging feeling that I’d do another one someday and figured it should be New York given how long I’ve lived here and what a great race it is.  From where I sit today, it’s hard to imagine doing another one.  Finishing is a truly great feeling, but boy is it a lot of work to get ready for it (not to mention a fair amount of pain both getting ready for it and doing it!).  Brad’s nuts — I say this with the utmost admiration — he’s in the process of doing 50 marathons, 1 in each state, mostly over the next 10 years.

The whole thing was incredible.  37,000 runners is just a sea of people.  There was never a point on the course when the field really thinned out – all you could see as a runner, in either direction, was just miles of heads bobbing up and down.  The crowd was amazing.  The New York Roadrunners Club estimates that 2 million people turn out to watch the marathon somewhere along the course, and I believe it.

The race was truly the opposite of the Big Sur Marathon, though.  Big Sur was silent, serene, and picturesque, with about 3,000 runners and zero spectators until about mile 24.  Yesterday’s race was raucous, crowded, and while Central Park and 5th Avenue were nice, you’d be hard pressed to call some of the sections of Queens and The Bronx we ran through picturesque.

Anyway…back to limping around the office today!

Last week, I wrote about Bringing People Along for The Ride by involving people in the process of ideating and creating change in your organization. That’s the most important thing you can do to make it easy for people to handle change.

But what about the people you don’t or can’t bring along for the ride in that way? If you organization has more than 10 people in it, there will inevitably be people where you’re IMPOSING CHANGE ON THEM. And honestly, even people who are involved in designing change still have to live through its impact.

Today’s post is about managing the actual impact.

The best thing you can do as a leader in helping your organization navigate change is to be empathetic to the fact that, even if you involve people in designing the solution, you are, in fact, making changes to their day to day lives. One of the best books I’ve ever read on this is Transitions: Making Sense of Life’s Changes, by William Bridges. And while there’s a lot more to the book than this one point, I’ll share two graphics from the book and its offshoots that say a lot.

Bridges’ basic concept is to think about changes as having three phases. The end of the old thing, the beginning of the new thing, and the time between the two – when the new thing has been announced, but the it hasn’t taken effect yet. Here’s a look at one powerful graphic on this front, where the point is that productivity (the red line) tanks briefly during the time of uncertainty with the overlay of human emotions at each phase.

Next let’s look at Bridges’ model for how to think about these three phases. This part is critical. They are not discrete phases, where everyone finished “ending” and moves onto “neutral” and then moves on to “new.” From the moment a change is in the offing, until after the change is implemented, people are simultaneously operating in all three zones at the same time, in different proportions.

That means when change starts, you’re already helping them understand that there will be a period of confusion followed by a bright new future. And it means that even when the bright new future has arrived, you’re still mindful of the confusion as well as the things that were special about the past.

I wrote about this a little bit in the second edition of Startup CEO and in this blog post on transitions and integration. The paragraph I’ll call out is:

For ourselves as leaders and me as CEO, knowing most of us would leave almost immediately post-deal, I wanted to have as elegant an exit as possible after 20 years. Fortunately, I had a good partner in this dialog in Mark Briggs, the acquiring CEO. Mark and I worked out rules of engagement and expenses associated with “the baton pass,” as we called it, that let our execs have the opportunity to say a proper goodbye and thank you to our teams, with a series of in-person events and a final RP gift pack. This was a really important way we all got closure on this chapter in our lives

The Baton Pass is a helpful analogy to think about this process. In a relay race, the two runners run alongside each other for a little while until they are at the same pace and proper spot, THEN one hands the other the baton. It’s the time when the past and the future collide, in a neutral zone. When you mark the great things and painful learnings that came before and launch into the bright new future.

The best thing you can do as a leader who is driving change through an organization is to Bring People Along for the Ride. Part of that is involving people in the creation of the new world. But it’s also recognizing that humans have to process change, and that takes time.

Blogiversary, Part IV

Four years on, as the British would say, OnlyOnce is going strong.  Cumulative stats show a steady 457 posts, about one every three days on average (same as it’s been all along), and a scant 409 non-spam comments. Maybe some day I’ll start being more edgy and provocative.  Or prolific.  Or Twitterific.  Or something.

Looking back over my initial “how’s it going” post and the last three anniversary posts, I’d say my reasons for blogging, out of my four original ones, have consolidated now around “Thinking” (writing short posts helps me crystallize my thinking) and “Employees” (one of our senior people once called reading OnlyOnce “getting a peek inside Matt’s head).  But I’d also add two new raisons d’etre to the list:

Book Reviews:  it’s not that I enjoy reading my own book reviews so much as I am glad I’m compiling a list of the business books I’m reading and what I think of them.  While it’s not comprehensive (I limit the blogging to business books, probably about 50% of what I read), it’s come in handy a few times to have a little online library for my own reference.

I like it:  I really, really enjoy writing.  I used to write all the time when I was younger.  High school newspaper editor, creative writing magazine founder, and all that.  I miss it.  Blogging is probably the only form of prose I regularly write now.  And it’s great.  The reawakening and sharpening of my writing skills has even inspired me to dive into a couple creative writing exercises, short stories mostly, in the past year.  So I just like doing it.

And isn’t that reason enough to do something?

I love the concept of Servant Leadership.  From the source, the definition is:

While servant leadership is a timeless concept, the phrase “servant leadership” was coined by Robert K. Greenleaf in The Servant as Leader, an essay that he first published in 1970. In that essay, Greenleaf said:

“The servant-leader is servant first… It begins with the natural feeling that one wants to serve, to serve first. Then conscious choice brings one to aspire to lead. That person is sharply different from one who is leader first, perhaps because of the need to assuage an unusual power drive or to acquire material possessions…The leader-first and the servant-first are two extreme types. Between them there are shadings and blends that are part of the infinite variety of human nature.

“The difference manifests itself in the care taken by the servant-first to make sure that other people’s highest priority needs are being served. The best test, and difficult to administer, is: Do those served grow as persons? Do they, while being served, become healthier, wiser, freer, more autonomous, more likely themselves to become servants? And, what is the effect on the least privileged in society? Will they benefit or at least not be further deprived?“

A servant-leader focuses primarily on the growth and well-being of people and the communities to which they belong. While traditional leadership generally involves the accumulation and exercise of power by one at the “top of the pyramid,” servant leadership is different. The servant-leader shares power, puts the needs of others first and helps people develop and perform as highly as possible.

This is a very broad societal definition, but it’s fairly easy to apply to a more narrow corporate, or even startup environment.  Are you as a CEO oriented primarily towards your people, or towards other stakeholders like customers or shareholders?  By the way, trying to do right by all three stakeholders is NOT a problem in a world of being oriented towards one.  It’s just a philosophy around which comes first, and why.  Our People First philosophy at Return Path is fair clear that at the end of the day, all three stakeholders win IF you do right by employees, so they do the best possible work for customers, so you build a healthy and profitable and growing business.

CEOs who practice Servant Leadership aren’t necessarily focused on power dynamics, or on helping those least privileged in society (at least not as part of their job)…but they are focused on making sure that their employees most important needs are met — both in the moment, as in making sure employees are empowered and not blocked or bottlenecked, and over the long haul, as in making sure employees have opportunities to learn, grow, advance their careers, make an impact, and have the ability to live a well balanced life.

I was in a meeting a couple weeks back with another leader and a few people on his team.  He *seemed* to practice Servant Leadership the way he was speaking to his team members.  But he wasn’t, really.  He was doing something I refer to as Sucking Down.  He was telling them things they clearly wanted to hear.  He was lavishing praise on them for minor accomplishments.  He was smiling and saying yes, when what he really meant was no.  He was practicing the art of Sucking Up, only to people on his team, not to a boss.  I got a sense that something wasn’t right during the meeting, and then post meeting, he actually fessed up to me — even bragged about it — that he was being disingenuous to get what he wanted out of his people.

There’s a clear difference between Servant Leadership and Sucking Down in the long run.  The danger comes in the moment.  Just as managers need to build good detection skills to sniff out evidence of someone on their team Sucking Up, employees need to be able to understand that clear difference in their managers’ behavior as they think about how to manage their careers, and even where to work.

Connecting with Other CEOs

CEOs get introduced to each other regularly.  Sometimes it’s through VCs or other investors, sometimes it’s through other CEOs, sometimes it’s because the two companies are already partners.  I try hard to meet personally or at least on the phone with other CEOs every time I get a chance, sometimes because there’s business to be done between Return Path and the other company; but always because I come away from every interaction I have with another CEO with some learnings to apply to myself and the company.

I have noticed two unrelated things over the years about my interactions with other CEOs who are in our industry, and therefore with whom I spend time more than once, that I find interesting:

First, the personality of the organization frequently (though not always) mirrors the personality of the CEO.  When the other CEO is responsive and easy to schedule a meeting with, it turns out the organization is pretty easy to work with as well.  When the other CEO is unresponsive to email or phone calls, or is inconsistent with communication patterns — one communication through LinkedIn, another via email, another via Twitter — people at Return Path who also work deeper within the other organization have experienced similar work styles.  I guess tone setting does happen from the C-suite!

Second, even when there is alignment of temperament per my above point, there is frequently a disconnect between CEOs and their teams when it comes to getting a deal done.  The number of times I’ve had a solid meeting of the minds with another CEO on a deal between our two companies, only to have it fall apart once the two teams start working through details is well north of 50% of the cases.  Why is this?  Maybe sometimes it’s unfortunately calculated, and the CEO is being polite to me but doesn’t really have any intent of moving forward.  In other cases, it’s a natural disconnect — CEOs have a unique view of their company and its long term strategy, and sometimes the people on their teams have different personal, vested interests that might conflict with a broader direction.  But in many cases, I think it’s also because some CEOs are weak at follow-up, and even if they give their team high-level direction on something don’t always check in to see how progress is or is not being made.  I know I’ve been guilty of this from time to time as well, so please don’t take this post to be self-righteous on this important point. Those of us who run organizations have a lot on our plates, and sometimes things fall between the cracks.  The best way to make sure this last point doesn’t happen is to really ensure the meeting of the minds exists — and for the two CEOs to hold each other accountable for progress on the relationship up and down the stack.

I will close this post by noting that most of the best relationships we as a company have are ones where the other CEO and I get along well personally and professionally, and where we let our teams work through the relationship details but where we hold them and each other accountable for results.