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!

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?

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.

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.

Don’t Ever Do a Conference Call from an Airport

Ever.  Just say no thank you, you’re not available.  Airports are terrible places to be on a phone call.  You can’t hear the call, the call is barraged with P.A. system announcements.  It’s disjointed and difficult. 

Better to force the call to happen at another time or send a delegate from your team or company on your behalf.  If you *must* do a call from an airport, I’d say best practices are:

1. Let the meeting organizer know ahead of time that you have no choice (if the meeting must be scheduled at that time)

2. Remind all participants up front that you’re in an airport

3. Make liberal use of the mute and unmute functions.  Phones all have different ways of doing this, but most conference call platforms have universal *6 mute and *7 unmute commands

4. If you can’t hear everything you need to hear on the call, ask one meeting participant at the end of the call if they can recap key items and next steps for you after the fact

Who Said VCs Don’t Add Value?

In case there’s anyone out there who reads my blog but not Brad Feld’s — if you’re a Firefox user, you have to read this posting about pipelining and take the two minutes to implement it.  It’s phenomenal.

Thanks, Brad!

(This is the second post in the series….the first one When to hire your first CBDO is here)

One of the tricky things about finding a great CBDO is that the role is fairly nuanced and there’s not a degree a person can get in “business development.” So you’re left with searching for someone based partially on experience, reputation, and alignment with your company culture and goals. But over the course of my career I have figured our what “great” looks like for the CBDO and I’m confident that what worked for us at Return Path and Bolster will work for any startup.

First, a great CBDO should have a good balance of the three core components Ken Takahashi outlined in his section of Startup CXO.  Those three components include partnerships, M&A, and strategy.  Even if a person started their careers out as an investment banker or a management consultant, or some other specialized field, they should still be able to bring all three competencies to bear to help further the goals of their team – to optimize the company’s place in the ecosystem. A one-trick pony will get you nowhere in the ecosystem and the CBDO needs to be a competent generalist in a wide range of skills.

Second, a great CBDO will look at business strategy first before trying to solve a problem because a solution that doesn’t advance the strategy will fail. It’s not enough to be able to develop a strategy, the great CBDOs will return to that strategy constantly. If a CBDO is highly skilled at one of the components, say M&A, they are likely to risk becoming the the proverbial hammer in search of a nail and they will put a primacy on M&A deals. The strategy acts as a safeguard to pursuing something because the CBDO wants it amd instead helps them pursue something that fits with the overal strategic drivers of the business. So, strategy is king in the CBDO world.

Third, a great CBDO will see the whole system at a company, not just one thing. They’ll see product (and all of its components) as well as go-to-market (and all of its components). Like the CEO, CFO, and Chief People Officer, the CBDO needs to have a holistic approach to everything and not only be closely aligned with the market-facing organizations. 

You can find this post on the Bolster Blog here.

(This is the second post in the series… the first one When to Hire your first Chief Customer Officer is here)

I mentioned in an earlier post that few startups begin with a full-time Chief Customer Officer and the likely scenario is to promote someone from within the service organization to that role. It’s possible that the person who takes on the CCO role will be ideal for the job, but often startups end up searching for someone outside the organization to lead the customer success team. Either way, promoting from within or hiring from outside, there are several telltale characteristics that great Chief Customer Officers share, and there are three things they do particularly well.

First, the CCO is the primary evangelist across your executive team and entire organization and this message should be so constant and consistent that everyone in your organization will be able to finish the sentence of the CCO. At Return Path our CCO, George Bilbrey, was constantly reminding everyone that the purpose of Return Path was to do the job the customer hired us to do.  In non-professional service businesses, where the bulk of the organization is not face-to-face with customers on a regular basis, it can be very easy for employees, teams, and projects to quickly become internally focused.  They focus on projects, milestones, internal metrics—all the things that customers don’t care about. The great CCO is the one who brings the Outside In, every day.

 A great CCO is equal parts quantitative and qualitative.  Almost all high-level work that the CCO and their team does includes quantitative measures: math, metrics, analytics, and statistics.  Net Promoter Score analysis.  Customer segmentation.  Customer profitability. Anything worth knowing has usually got a measurement behind it and the CCO must nail these or, if partnering with the CFO or someone else, at least be fluent in them.  And the greatest CCOs are also the ones with the most customer empathy, something that comes by listening carefully to customers, and I mean really listening. Once they understand customers on an emotional level the great CCOs have the ability to relate that feeling to others in the company, and to other customers.  They can recite customer and experience stories like a politician giving a stump speech.

The final characteristic or skill of a great CCO is that they like designing processes.  Account Management, Customer Success, Support, Onboarding, Professional Services, Knowledge Management — all the different teams reporting to a CCO — must work together in a seamless way to apply their specific areas of expertise to bring general solutions to the customer.  The head of the team, the CCO, must be a rock star at process envisioning and design, and at engaging teams in the process.  Otherwise, the teams will be inefficient, hand-offs will be missed, there will be no single source of truth, and customers will not be well served.

Whether your CCO is promoted from within your organization or hired from the outside, the great ones all have the same traits: evangelists for the customer, quantitative and qualitative skills, and a passion for processes that connect disparate parts of the organization into a seamless, functioning team.

(You can find this post on the Bolster Blog here)

New Daily Read

If you haven’t seen it or heard about it yet, run – don’t walk – to sign up for either the RSS feed or daily email digest from Silicon Alley Insider, a new publication that’s a sort of NYC based version of ValleyWag.  SAI is run by famed analyst Henry Blodget and was started by former DoubleClick CEO and CTO Kevin Ryan and Dwight Merriman, now serial Silicon Alley entrepreneurs (at an epic pace, no less).

The writing is easy and has a bit of that tabloid feel to it, but that’s a nice change.  The fact that the publication fills a void that’s been open for years since the disappearance of Jason Calacanis’ Silicon Alley Reporter is somewhat unexplainable, but I’m glad to see the void filled.  It’s still early days for the publication (the site says "beta" on it), but it’s a must-read if you’re in the Internet business…even if you’re on the west coast!