Apr 15 2021

Should CEOs wade into Politics?

This question has been on my mind for years. In the wake of Georgia passing its new voting regulations, a many of America’s large company CEOs are taking some kind of vocal stance (Coca Cola) or even action (Major League Baseball) on the matter. Senate Majority Leader Mitch McConnell told CEOs to “stay the hell out of politics” and proceeded to walk that comment back a little bit the following day. The debate isn’t new, but it’s getting uglier, like so much of public discourse in America.

Former American Express CEO Harvey Golub wrote an op-ed earlier this week in The Wall Street Journal entitled Politics is Risky Business for CEOs (behind a paywall), the subhead of which sums up what my point of view has always been on this topic historically — “It’s imprudent to weigh in on issues that don’t directly affect the company.” His argument has a few main points:

  • CEOs may have opinions, but when they speak, they speak for and represent their companies, and unless they’re speaking about an issue that effects their organization, they should have Board approval before opening their mouths
  • Whatever CEOs say about something political will by definition upset many of their employees and customers in this polarized environment (I agree with this point a lot of the time and wrote about it in the second edition of Startup CEO)
  • There’s a slippery slope – comment on one thing, you have to comment on all things, and everything descends from there

So if you’re with Harvey Golub on this point, you draw the boundaries around what “directly affects” the company — things like employment law, the regulatory regime in your industry, corporate tax rates, and the like.

The Economist weighed in on this today with an article entitled CEO activism in America is risky business (also behind a paywall, sorry) that has a similar perspective with some of the same concerns – it’s unclear who is speaking when a CEO delivers a political message, messages can backfire or alienate stakeholders, and it’s unclear that investors care.

The other side of the debate is probably best represented by Paul Polman, longtime Unilever CEO, who put climate change, inequality, and other ESG-oriented topics at the center of his corporate agenda and did so both because he believed they were morally right AND that they would make for good business. Unilever’s business results under Polman’s leadership were transformational, growing his stock price almost 300% in 10 years and outpaced their peers, all as a “slow growth” CPG company. Paul’s thinking on the subject is going to be well documented in his forthcoming book, Net Positive: How Courageous Companies Thrive by Giving More Than They Take, which he is co-authoring with my good friend Andrew Winston and which will come out later this year.

While I still believe that on a number of issues in current events, CEOs face a lose-lose proposition by wading into politics, I’m increasingly moving towards the Paul Polman side of the debate…but not in an absolute way. As I’ve been wrestling with this topic, at first, I thought the definition of what to weigh in on had to come down to a definition of what is morally right. And that felt like I was back in a lose-lose loop since many social wedge issues have people on both sides of them claiming to be morally right — so a CEO weighing in on that kind of issue would be doomed to alienate a big percentage of stakeholders no matter what point of view he or she espouses.

But I’m not sure Paul and Andrew are absolutists, and that’s the aha for me. I believe their point is that CEOs need to weigh in on the things that directly affect their companies AND ALSO weigh in on the things that indirectly affect their companies.

So if you eliminate morality from the framework, where do you draw the line between things that have indirect effects on companies and which ones do not? If I back up my scope just a little bit, I quickly get to a place where I have a different and broader definition of what matters to the functioning of my industry, or to the functioning of commerce in general without necessarily getting into social wedge issues. For want of another framework on this, I landed on the one written up by Tom Friedman and Michael Mandelbaum in That Used to be Us: How America Fell Behind in the World It Invented and How We Can Come Back, which I summarized in this post a bunch of years ago — that America has lost its way a bit in the last 20-40 years because we have strayed from the five-point formula that has made us competitive for the bulk of our history:

  • Providing excellent public education for more and more Americans
  • Building and continually modernizing our infrastructure
  • Keeping America’s doors to immigration open
  • Government support for basic research and development
  • Implementation of necessary regulations on private economic activity

So those are some good things to keep in mind as indirectly impacting commercial interests and American competitiveness in an increasingly global world, and therefore are appropriate for CEOs to weigh in on. And yes, I realize immigration is a little more controversial than the other topics on the list, but even most of the anti-immigration people I know in business are still pro legal immigration, and even in favor of expanding it in some ways.

And that brings us back to Georgia and the different points of view about whether or not CEOs should weigh in on specific pieces of legislation like that. Do voting rights directly impact a company’s business? Not most companies. But what about indirect impact? I believe that having a high functioning democracy that values truth, trust, and as widespread legal voter participation as possible is central to the success of businesses in America, and that at the moment, we are dangerously close to not having a high functioning democracy with those values.

I have not, as Mitch McConnell said, “read the whole damn bill,” but it doesn’t take a con law scholar to note that some pieces of it which I have read — no giving food or water to people in voting lines, reduced voting hours, and giving the state legislature the unilateral ability to fire or supersede the secretary of state and local election officials if they don’t like an election’s results — aren’t measures designed to improve the health and functioning of our democracy. They are measures designed to change the rules of the game and make it harder to vote and harder for incumbents to lose. That is especially true when proponents of this bill and similar ones in other states keep nakedly exposing the truth when they say that Republicans will lose more elections if it’s easier for more people to vote, instead of thinking about what policies they should adopt in order to win a majority of all votes.

And for that reason, because of that bill, I am moving my position on the general topic of whether or not CEOs should wade into politics from the “direct impact” argument to the “indirect impact” one — and including in that list of indirect impacts improving the strength of our democracy by, among other things, making it as easy as possible for as many Americans to vote as possible and making the administration of elections as free as possible from politicians, without compromising on the principle of minimizing or eliminating actual fraud in elections, which by all accounts is incredibly rare anyway.

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Apr 8 2021

How to Select a CEO Mentor or CEO Coach

(This is the second in a series of three posts on this topic.)

In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them.

Selecting a CEO Mentor is literally like selecting a teacher but at a vocational school, not at a research university.  You want to select someone who has done something several times or for several years; done it really well; documented it in some organized way (at least mentally); and can articulate what they did, why, what worked and what didn’t, and help you apply it to your situation.  Do you want to be taught how to be an electrician by someone with a PhD in Electrical Engineering, or by someone who has been a master electrician for 20 years?   Fit matters mostly around values.  It’s hard to get advice from someone whose values are quite different, as their experiences and their metrics for what did and didn’t work won’t apply well to yours.  Fit is a lot less around personality, although you have to be able to get along and communicate with the person at a basic level  Find someone with the right experience set that you can learn from RIGHT NOW.  Or at least this year.  Maybe the person is the right mentor next year, maybe not.  Depends on what you need.  For example, if you’re running a $10mm revenue DTC company, find someone who has scaled a company in the DTC or adjacent eCommerce space to at least $25-50mm. 

Although I’ve been very international in getting mentoring as a CEO over the years, I’ve never hired a formal CEO Mentor. Several people, from my dad to my independent directors to the members of my CEO Forum have played that role for me at different times over the years. Knowing what I know now, I’m working with CEO Mentors who have experience with talent marketplaces at different scale, since this is a new industry for me.

Selecting a CEO Coach is different.  I got lucky in my selection of a CEO Coach almost 20 years ago.  My board member Fred Wilson told me I needed to work with one, I naively rolled my eyes and said ok, he introduced me to Marc Maltz, I told Marc something like “I need a coach because clearly I need to learn how to manage my Board better,” and for some reason, he decided to take the assignment.  I got lucky because Marc ended up being exactly the right coach for me, going on 20 years now, but I didn’t know that at the time.  

Selecting a CEO Coach is all about who you “click with” personality wise, and what you need in order to be pushed to grow developmentally.  CEO Coaches come on a spectrum ranging from what I would call “Quasi-Psychiatrist” on one end, to “Quasi-Management Consultant” on the other end.  The former can be incredibly helpful — just note that you will find yourself talking about your thoughts, feelings, and family of origin a fair bit as a means of uncovering problems and solutions.  The latter can be helpful as well — just note that you will find yourself talking about business strategy and having someone hold up the proverbial mirror so you can see you the way other people see you as the CEO, quite a bit.  There is no right or wrong universal answer here to what makes someone the right choice for you.  For me, if one end of the spectrum is a 1 and the other is a 5, I prefer working with people who are in the 3-4 range.  

Therapy and coaching are different, though.  A good CEO Coach who is a 1 will refer clients to therapy if they see the need. While coaching can “feel” therapeutic, and actually may be therapeutic, it is not a replacement for therapy. The differences between the 1s and the 5s are not just style differences but also really what you want the content of the coaching to be.  A 1 is going to help you discover and drive to your leadership style.  A 5 is going to help you align those decisions to how you actually act, what approaches you bring to the organization and how you address challenges.  Some CEO Coaches can move back and forth between all of these, but knowing where you sit with your needs relative to the coach’s natural style when you pick a coach is critical.

I know CEOs who have shown tremendous growth as humans and leaders with Coaches who are 1s and Coaches who are 5s.  A good CEO Coach is someone you can work with literally forever.   

I always encourage CEOs to interview multiple Coaches and specifically ask them what their coaching process is like and what their coaching philosophy is.  How do they typically start engagements.  How structured or unstructured are they in their work?  Check references and ask some of their other CEO clients what it’s been like to work with them.  This is all true to a much lesser extent with Mentors.  In both cases, you should probably do a test session or two before signing up for a longer-term engagement.  You wouldn’t buy a car without taking it for a test drive.  This is an even more consequential decision.  

And in both cases, there should be no ego in the process.  You should never feel like you’re being sold by a CEO Coach or CEO Mentor.  And they shouldn’t feel hurt by you picking someone else, either.  Alignment and chemistry are so critical – there is no way to have that with every person, and the good professionals in this industry should know that.

The bottom line is that hiring a CEO Mentor is low risk. If it’s not working out, you stop engaging. Hiring a CEO Coach is a longer-term decision, and it’s worth having couple of sessions with a coach before making the commitment.

Next post in the series coming:  How to get the most out of working with a CEO Mentor or CEO Coach 

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Apr 1 2021

The Difference Between a CEO Coach and a CEO Mentor and Why Every CEO Needs Both

(This is the first in a series of three posts on this topic.)

Harry Potter was lucky.  He had, in Albus Dumbledore, the ultimate wise elder, in his corner.  Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys.

All of us would benefit from having an Albus Dumbledore in our lives.  But most of us don’t — and most of the people we’d call on to be that wise elder in our corner aren’t capable of the full range of advice and counsel that Dumbledore is. 

Why work with a Coach or a Mentor?  I’ll start this post with a quick argument in favor of CEO Coaches and Mentors (sometimes called Advisors).  Even as a 20-something first-time CEO years ago, I was deeply skeptical of the value of a Coach, but that was in 1999 or 2000 when coaches weren’t so commonplace.  Now that their value seems much more obvious, and there are so many amazing Mentors and Coaches available, I’m surprised by how many CEOs I speak to still seem skeptical about their value.  Just think — the world’s greatest athletes, the ones who get paid zillions of dollars because they are the best in the world at something, use MULTIPLE coaches DAILY to perfect their craft and keep them focused.  Why should Rafael Nadal or Serena Williams have a trainer and a coach, but not you?

I’ve benefited over the years from the advice of more people than I can ever count or thank.  But when it comes to being a CEO, I have leveraged the counsel of a CEO Coach or Mentor principally in three different areas:

  1. Functional topics on the craft of being a CEO from the lofty “how to run a board meeting” to the nitty gritty details of “how to do a layoff”
  2. Developmental/behavioral topics like “how I show up as a leader in the organization,” or “how to be a better listener”
  3. Team Effectiveness topics like “how do I get the most out of my leadership team,” or “why doesn’t Person X trust Person Y and how does that impact team performance?”

In some unusual circumstances, you can find a person who does all three of these things for you and can scale as you and your company grow.  But for the most part, getting all three of these things requires engaging two different people, and maybe even more mentors.  

What’s the difference between a CEO Mentor and a CEO Coach?  Counsel on Item 1 above — what I would call CEO Mentorship — almost certainly requires someone to have been a CEO — preferably multiple times, or for a long period of time, or through multiple stages of company growth, or two or three of those qualifiers.  This is the kind of person who can literally teach you how to do CEO things.  These people are super busy, they won’t have open ended amounts of time for you, but you should expect sage wisdom and answers when you need them.  And you can have more than one of them at a time, or change them out as your company evolves and your needs change.

Counsel on items 2 and 3 — what I would call CEO Coaching — frequently come together in a professional who is and has been for a while, a coach.  The person might have had a significant career in business before becoming a coach but wasn’t necessarily a CEO.  The person probably has some kind of academic grounding, like a Master’s degree in Organizational Development or Industrial Psychology, or a Certificate in Coaching.  This is the kind of person who can do things for you and your team like facilitate meetings, run assessments like Myers-Briggs or DISC, and coach other leaders on your team.  This person is dedicated to helping you be the best leader, professional, and CEO that you can be and must be both empathetic and comfortable pushing you hard.  

Sometimes you get mentorship and coaching in the same person, but almost only with CEO Coaches who are also CEO Mentors by my definition above.

Five signs you need a CEO Mentor and/or Coach:

  • You are playing ‘whack-a-mole’ — running from crisis to crisis in your organization and are not able to make time to think, be current with email, or make time for important things like hiring senior executives
  • Your board is getting frustrated with you, your team and/or the lack of progress in the business
  • The company isn’t scaling as fast as it should
  • Your leadership team is not a cohesive team and you are in the middle of all decisions
  • The company has high employee turnover and/or poor reviews on Glassdoor 

Do yourself and your company a favor and invest in a CEO Coach and Mentor(s). It’s an investment in accelerating your own and your company’s success. In later posts, I’ll talk about how to hire and best leverage both Coaches and Mentors. 

Next post in the series coming:  How to Select a CEO Mentor or CEO Coach

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Mar 25 2021

Addicted to Ruthless Efficiency

Last week I wrote about The Tension That Will Come With the Future of Work.  No one knows what the post-pandemic world of office vs. remote work will look like, but there are going to be some clear differences between how people will respond to being in offices or not being offices going forward.  As I said in that post, I think the natural, gravitational pull for senior people will be to do more remote work, because of a combination of their commutes, their personal time, their work setups at home, and their level of seniority…but with the possible exception of engineers, “all remote” may actually not be in the best interest of a number of junior or more introverted team members.

Two things popped up in the last few days that are making it clear to me that there’s another issue all of us — whether you’re a CEO or CXO or an entry level employee — will face.  We’ve become much more efficient in how we do our jobs and run our lives.  In my case, I’ll go ahead and say it — I’m addicted to the efficiency and scarcity of social interactions in my work life now in a way that I’m going to find hard to unwind, so I’m calling it “ruthless efficiency.”

Example 1 is a time-based example.  I’ve been doing virtually all client-related meetings, whether sales calls or customer success calls, in 30 minutes over Zoom or equivalent for a year now.  Sometimes I even get one done in 15 minutes.  Very, very rarely, I’ll book one for an hour.

One of my Bolster colleagues who lives not too far away in Connecticut is having drinks with a very important potential partner one night next week as the temperatures outside warm up here in the northeast.  She invited me to join — and really, I should join.  But then “ruthless efficiency math” sets into my thinking.  Instead of a 30 zoom, this will take me three hours – an hour drive each way plus the meeting.  Maybe I get lucky and I can do a call or two from the car, but is the meeting really worth 4-6x the amount of time just so I can be in person?  Even though this is the kind of thing I would have done without hesitation a year ago…that calculus is really hard to make from where I sit today.

Example 2 is an expense-based example.  We have spent basically $0 for a year on T&E.  Now we are planning some kind of a multi-day team meeting a few weeks from now around the 1-year anniversary of the company to work on planning for the next couple quarters.  The quarterly offsite, including travel, hotels, etc., has been a deeply-ingrained part of my leadership Operating System for 20-25 years now.  OF COURSE we should do this meeting in person and offsite if the public health environment allows it and people are comfortable.  But then “ruthless efficiency math” sets into my thinking.  What’s this meeting going to cost?  $10,000?  Depends where we do it and how many team members come since we have people in multiple cities.  But YIKES, that’s a lot of money.  We are a STARTUP.  Shouldn’t we use money like that for some BETTER purpose?

Forget the big things.  I think we all realize that we don’t have to hop on a plane now and do a day trip to the other coast or Europe or Asia for a couple meetings unless those meetings are do-or-die meetings.  It’s these little things that will be tough to readjust now that we’ve all gotten used to having hours upon hours, and dollars upon dollars, back on our calendars and balance sheets because we’ve gotten addicted to the amazing, and yet somewhat ruthless efficiency of the knowledge worker, pandemic, work from anywhere, get it done in 30 minutes on a screen way of life.

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Mar 22 2021

OnBoards Podcast

My podcast with OnBoards is live, talking with Raza and Joe about the importance of adding independence, first-time directors, and diversity to startup boards, and how Bolster helps companies achieve that quickly and inexpensively.

I’m writing a lot about Boards at the moment on the Bolster blog. We’re compiling all of those posts into a couple of eBooks. Once all of that is done, I’ll put some digests up here on StartupCEO.com as well as make the eBooks available for download.

But the gist of it is that we are working hard to break the logjam of diversity on startup boards, and we’re starting to meet with some great success with our clients.

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Mar 18 2021

The Tension That Will Come With the Future of Work

The Tension That Will Come With the Future of Work

A lot has been written about the Work From Anywhere life that knowledge workers are leading right now due to the pandemic, and what will come next.  Fred has a great post on it, and I’m curious to see how his and Joanne’s “Home Office Away From Home” space called FrameWork does when it opens.  In that post, he references a few other posts and articles worth reading:

Instead of entering the debate about what the future will look like, which no one really knows other than to say “not like the past,” I want to focus on a tension I’ve been mulling over lately, and that is the tension between a company’s leaders and its employees.  You could also call it a tension between extroverts and introverts.  And in this regard, Packy McCormick is both right and wrong about the debate:  right in the sense that employees will make the decision, not companies; wrong in the sense that the best employees “are not going to work for companies that make them shave, get dressed, hop into a car or a crowded subway, and sit at a desk in an office five days a week with their headphones on trying to avoid distractions and get work done.”  That’s a blanket statement that, as with most blanket statements, misses an incredibly important point.

That some people like, want to, need to, or benefit from working in offices more often than not.

That those people are some of the most talented, creative, and high potential people in an organization.

And that those people are frequently the ones with the least “voice” in an organization — new employees, younger workers, introverts, and people from underrepresented groups.

It will be really easy for senior people who, in many cases, have longer commutes and kids they are now accustomed to seeing a lot more, not to mention really nice and private home offices, to default to working from home.  In many cases, they’ve already done more of that than most employees, well, because they can.  But the problem is that those people are perfectly fine working from home.  Work and decisions come to them.  Their career trajectories are pretty set.  They will seek out anyone in the organization to ask them any question, any time.

But think about the topic from the perspective of an entry level account coordinator, an associate product manager, a graphic designer in marketing, a financial analyst in the FP&A group, or an AR specialist in accounting. .  Less exposure to decision makers can’t possibly help this.  If you’re one of those people, here are the things you miss out on when there’s no office:

  • You don’t get to participate in or overhear interesting conversations in the break/lunch room or at the water cooler about something going on in the company that you’re not working on.  This reduces your ability to learn in unstructured ways at work or get thoroughly onboarded into a new company
  • You don’t get to see who comes and goes from the office or different meeting rooms.  This may sound silly, but watching a business in, seeing who is in a glass-walled conference room or what slides are up on the wall, helps employees stimulate good ideas about their day to day work.  This limits your ability to connect the dots and better understand the big picture at work 
  • You don’t get to have a casual conversation with your department head or CEO in the elevator or hallway or a conference room between meetings.  That “skip level” leader is much less likely to know who you are or what you do.  This can make it harder for you, the next time you have an idea you want to share or feedback you want to give, to approach a leader.  It also makes it a little tougher for you the next time you’re in line for some kind of promotion or development opportunity

Of course all employees CAN in theory make themselves known, can learn, can seek out others in the organization, and can try to re-create hallway serendipity from the comfort of their own Zoom screens.  It just doesn’t come naturally to most; practically speaking for many, it’s impossible; and it’s particularly hard for younger or quieter team members.  There’s a ton of research about how women in particular aren’t as comfortable advocating for themselves when it comes time to ask for a raise or a promotion.  If you’re the CEO of a 100 person organization, you might be inclined to chat with the new entry level AR person at the coffee machine for a few minutes; you’re unlikely to be excited about a 30-minute Zoom with her.  

(By the way, this whole construct may be different for engineering, where engineers are likely more comfortable with remote work AND aren’t held back in their career development as a result.)

I’ll close this post with an anecdote.  As part of our work at Bolster, I was doing something called an Executive Team Scalability Assessment with the CEO of a $75mm SaaS company a month or so ago.  When we were doing a review of how strongly each of his leaders role modeled company values, he paused when he got to one leader and said, “I honestly don’t know.  That person has only been here 10 months, but don’t worry, that’s just because of the pandemic.  I haven’t seen them in action.”  10 months!  People will discover at some point that it was much easier to “lift and shift” an existing organization to the cloud in year 1 of the pandemic than it will be to sustain or build a culture with a lot of new employees in year 2 or 3 of remote-first work.

CEOs who care about their culture, their people, inclusion and belonging, and their people’s professional development will have to really re-think how things work if they are going to steer their companies towards remote-only policies, or even remote-first employees, and still be inclusive workplaces.  That doesn’t mean it can’t be done.  But gravitating to a remote-only way of life, even if it’s personally enticing or if some talented and vocal employees demand it, may not be in the best interest of their overall company and employee population.

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Mar 16 2021

Soliciting Feedback on Your Own Performance as CEO

(Excerpted from Chapter 12 of Startup CEO)

As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things:

  1. Asking for feedback
  2. Accepting feedback gracefully
  3. Acting on feedback
  4. Asking for follow‐up feedback on the same topic to see how you did

In some respects, asking for it is the easy part, although it may be unnatural. You’re the boss, right? Why do you need feedback? The reality is that all of us can always benefit from feedback. That’s particularly true if you’re a first‐time CEO. Even more experienced CEOs change over time and with changing circumstances. Understanding how the board and your team experience your behavior and performance is one of the only ways to improve over time. It’s easier to ask for feedback if you’re specific. I routinely solicit feedback in the major areas of my job (which mirror the structure of this book):

Strategy. Do you think we’re on target with what we’re doing? Am I doing a good enough job managing to our goals while also being nimble enough to respond to the market?

Staff management/leadership. How effective am I at building and maintaining a strong, focused, cohesive team? Do I have the right people in the right roles at the senior staff level?

Resource allocation. Do I do a good enough job balancing among competing priorities internally? Are costs adequately managed?

Execution. How do the team and I execute versus our plans? What do you think I could be doing to make sure the organization executes better?

Board management/investor relations. Do you think our board is effective and engaged? Have I played enough of a role in leading the group? Do you as a director feel like you’re contributing all you can? Do I strike the right balance between asking and telling? Are communications clear enough and regular enough?

Accepting feedback gracefully is even harder than the asking part. You may or may not agree with a given piece of feedback, but the ability to hear it and take it in without being defensive is the only way to make sure that the feedback keeps coming. Sitting with your arms crossed and being argumentative sends the message that you’re right, they’re wrong, and you’re not interested. If you disagree with something that’s being said, ask questions. Get specifics. Understand the impact of your actions rather than explaining your intent.

The same logic applies to internalizing and acting on the feedback. If you fail to act on feedback, people will stop giving it to you. Needless to say, you won’t improve as a CEO. Fundamentally, why ask for it if you’re not going to use it? And that leads right into the fourth point, closing the loop with the person who gave you feedback on whether or not your actions achieved the desired change.

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Mar 11 2021

Second Verse, Same as the First…Except Way Better

Almost a year into my second journey as a startup CEO at Bolster, and I’m getting more and more questions from other CEOs about what it’s like doing a second startup after almost 20 years at the first one…and achieving pretty good scale by the end.  The short answer is, it’s the same, only it’s way better.  Here’s why.

I’m more confident.  So is our whole founding team.  When Jack and I started Return Path, we were 29.  This time, we were 49 — and the average age of the founders was probably 46 or 47.  The bottom line is that we don’t know everything about the business we’re building, but we know what we’re doing in terms of building a business, a startup, a software company, a service-oriented business, leading a team, planning, executing, and on and on.  Confidence in all of those areas means large portions of our day and brain space are freed up to focus on the actual construction of the business without worrying if we’re doing things right or wrong.

It’s much easier to build a startup today.  1999 wasn’t the dark ages, but it feels like a different millennium in terms of what it’s like to start a technology company from scratch.  The cloud and micro services/APIs mean that we are able to build our platform much more quickly at much lower cost than in the past.  And in terms of tooling the business, we got up and running with about 20 different DIY cloud/SaaS solutions in about 6 weeks for a cost of less than $10k/year.

We are sharper on execution and impatient for success.  Your first startup in your 20s is a lot about “enjoying the startup journey.”  This time around, our team is significantly more focused on critical stage-gate success metrics.  In both cases of course, the objective was to win, but this time around, we are much more focused on getting to that point sooner and with less waste.

We are a lot more productive.  Ok, fine, we’re cheating because of COVID and working from home.  No train commutes.  No plane trips.  No water cooler chatter.  No fluff.  It’s not sustainable, and I’ll write about that more in a future post.  But it’s leading to a surge of productivity like I’ve never experienced or seen before in my career.  I do like to think at least some of it comes from professional maturity — we’ll see when life returns to something more closely approximating normal.

I am having a blast being on the front lines.  I went from running a 500-person company, where I’d honed my job and skill set around communication, people issues, and mobilizing the army to go do things…to spending less than 5% of my time running the company and managing people.  Now depending on the moment, I’m an SDR, a customer success manager, a product manager, and a marketing copywriter.  And probably some other things, too.  And I love every minute of it.  It’s a lot more fun to see the direct impact of my actions on the business as opposed to only really seeing the direct impact of my actions on the people in the business (and occasionally then on some aspect of the business as an individual contributor).

Maybe I’m not having a typical second startup experience.  I know some friends who had successful first exits and hated going back to square one, or failed at a second business and were really disappointed about it, only to shift careers.  But my experience so far is a much better second verse, even though it’s a bit like the first.

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Mar 10 2021

StartupCEO.com: A New Name for OnlyOnce

Welcome to the new StartupCEO.com!

I started writing this blog in May of 2004 with an objective of writing about the experience of being a first-time entrepreneur — a startup CEO — inspired by a blog post written by my friend, long-time Board member and mentor Fred Wilson entitled “You’re only a first time CEO once.”  The blog and the receptivity I got along the way from fellow startup CEOs encouraged me to write a book called Startup CEO:  A Field Guide to Scaling Up Your Business, which was originally published in 2013 and then again as a second edition last year in 2020.

Today I am relaunching the blog as StartupCEO.com both to reflect that relevance of that brand as the book continues to get good traction in the startup ecosystem, and to reflect the fact that I’m now on my second startup as CEO, so “Only Once” doesn’t seem so fitting any more.

The web site has a very minimalist design – and I realize many of you read posts on either RSS or email — those will still operate the same as they have been (no new RSS feed).

As I approach the first anniversary of starting our new company, Bolster, where we help startup CEOs scale their teams, themselves, and their boards, I am recommitting to this blog and will try to post at least once a week.  Because there is a lot of overlap between this blog and Bolster’s blog (which I’d encourage you to subscribe to here either by email or RSS), posts will occasionally show up on both blogs, or I’ll put digests of Bolster blog posts here.  

But the Bolster blog will be broader and will also have many additional authors besides me, while this blog will remain distinct about some of the experiences I’m having as a startup CEO.

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Feb 3 2021

Use Cases to Bolster Your Team: How to Leverage On-Demand Talent in Your Business

(This post was written by my colleague Bethany Crystal and originally published on the Bolster blog yesterday. While I am still trying to figure out what posts to put on this blog vs. Bolster’s blog since the blogs are pretty similar, I will occasionally run something in both places.)

At Bolster, we believe that 2021 will mark the rise of the on-demand economy for executives. More than ever before, executives are seeking out roles that distinctly aren’t full-time for a variety of reasons – they’re in between full-time roles and want to stay engaged and meet a wide range of potential employers; they’re retired or semi-retired/post-exit and want to keep working, just not full-time; they’re fully employed but are looking for advisory opportunities to help others; or they are committed to the more flexible lifestyle that being an on-demand affords. As business leaders, you might be wondering how to take advantage of this trend and incorporate on-demand talent onto your existing team. Don’t worry – we’ve got you covered.

Let’s start with a quick primer on the distinct types of on-demand talent. Here are the four most common themes we see among our member network at Bolster:

The Four Types of On-Demand Talent

  1. Interim: Someone who is partially or fully dedicated to working with your company, but only temporarily (you can think of them as “filling a gap”)
  2. Fractional: Someone who works part-time (or “fractionally”) with your company on an ongoing basis (they “own” the function on a long-term, part-time basis)
  3. Advisor or Coach: Someone who supports your existing team by offering external advising, coaching, or mentorship as needed (this might be on a temporary or long-term basis)
  4. Project-Based: Someone who is brought on to complete a specific project or a fixed span of work (this is the closest to typical consulting work)

Depending on your business needs, the capacity of your existing team, and your resourcing, you might find it useful to have one or more on-demand executives in the mix at any given time. We’ve also found this can be a great way to keep things fresh at the leadership level and make sure new ideas are circulated with some regularity.

Business Opportunities for On-Demand Talent

While every company’s on-demand talent needs will vary, we’ve already seen a few patterns emerge from the 2,000 executives in our member network. Here are a few times to think about bringing on-demand work to your business.

Choose interim work if you need…

  • A temporarily placeholder at the exec level
    Whether unexpected or planned, transitions at the executive level can come with a high cost: Any week that goes by with an unfilled seat adds more work to the team, contributes to business lag, or both. While full executive searches can take six months (or more!) to get right, many CEOs find it helpful to bring on interim help as a “stopgap” in the meantime. The most obvious benefit of interim on-demand work is to prevent your business from falling behind in areas where you may not have a deep bench below the executive level. And you might also consider that bringing in a seasoned professional as you conduct your full-time search will give your team a proxy to compare against, making that placement process a bit easier. Last – while it’s not a guarantee, there’s always the chance that your interim hire is a great fit for you and wants to stick around for the long term! You then benefit from an on-the-job “interview” or audition.
  • Surge capacity staffing
    Imagine a situation where your business doesn’t need an executive in a particular function. You’re small, scrappy, and you’re getting along perfectly well with the team you have in place – and you can fill in the bits of executive leadership required for that function yourself from time to time. But then something pops up where you need to be the CEO and can’t afford to ALSO be the CXO. An interim CXO could be the right solution. For example, the 3-5 months run-up to a Series A or B financing could be a good time to bring on an experienced CFO if your only relevant team members are handling AP, AR, and Payroll. Or you could be working on your company’s public launch with a less experienced marketing team and an agency – and an interim CMO could make all the difference between success and sideways.
  • Parental leave coverage
    With a growing business trend of increased parental leave coverage, CEOs are starting to use interim executives to fill holes that might temporarily exist on the leadership team. Interim work is particularly useful if there isn’t an obvious “second in command” role on that team who might take on a stretch project in their absence. Implemented correctly, bringing on an interim exec can also help to squash any fears of “getting replaced” while someone is away on leave. As an added bonus, bringing in a new face (if only temporarily) can give the remaining team a chance to “try out” a new leadership style and share feedback about what worked and didn’t work during the interim period.

Choose fractional work if you need…

  • A seasoned professional’s experience and skillset (but not all the time)
    Before every full-time leadership hire, there is the sticky “in between” period of need. That’s the period when some work starts piling up, but not quite enough to fill an entire work week for one person at the executive level – or the period when you know you need a more seasoned leader in a function but just can’t afford one full-time. If you don’t have an experienced executive in the role, you miss opportunities for effectively setting up scalable practices and processes. Often, a lack of senior focus in a functional area means that you miss strategic opportunities, and sometimes it also means that you expose yourself to risk that could be avoided with the right person having ownership of the function. This is the perfect time to introduce fractional work to your business. The most classic example of fractional executive talent is the CFO who oversees the bookkeeping and accounting for several companies at once. But you can find a fractional executive for just about anything. You might consider this type of on-demand executive if you don’t yet have anyone in that functional area, if you have a team of less experienced specialists or even a more junior generalist leader in that functional area, if you want a taste of what it’d be like to dedicate more resources there, or if you need just a few things done right, without having to think about them yourself.

Choose advisory or coaching work if you need…

  • Mentorship for your current executives
    Sometimes it’s helpful to see what “great” looks like in order to achieve greatness yourself. If you’re looking for a way to give a current leader an added boost to their development plan, consider bringing on someone who can serve as a mentor or advisor on a temporary or long-term basis. Someone who has been in your shoes before and can give advice and guidance based on their experience. This on-demand exec role has two big benefits: The first being that it demonstrates to your executive team that you’re committed to their ongoing success and growth, which boosts morale (and hopefully performance). The second is that you’ll be able to equip your current team with the tools they each need to scale instead of having to bring on a new wave of executives for each business stage. The advisor or coach usually works a few hours per month, once they’ve set up a strong coaching relationship.
  • Access to top talent without the full-time price tag
    Just as remote work unlocked the potential to find “the best of the best” without geographic constraints, on-demand work does the same at the executive level. More and more, we’re seeing CEOs incorporate advisors to their business as a way to gain exposure to best in class talent (at a fraction of the cost). This can be a great way to introduce subject matter or functional expertise into your organization without committing to a full-time salary.

Choose project work if you need…

  • A fixed-scope expert engagement at the executive level
    Just as tools like Task Rabbit made it possible to find experts to accomplish tasks on a personal level (such as moving furniture or painting a bedroom), on-demand talent makes it possible to find seasoned executives to complete one-off projects at an expert level. That’s why, on Bolster, we ask each each member to indicate what roles they can take on, and also what projects they can be hired to do. As a CEO, you might consider outsourcing some of the crunchy stuff at the exec level that might take a lot of time, or in cases where you need a quick turnaround to get to an MVP. Common projects we’ve seen to date include building sales commission plan structures, designing a go-to-market launch plan for a new product, running due diligence on an acquisition, overhauling pricing and packaging, working on a strategic plan, TAM analysis, budgeting process, or creating a diversity & inclusion strategy for the company.
  • An experimental project that won’t distract the current team
    One final area where you might consider on-demand work is for a project that feels more like an addendum to your current business, or an early experiment. At Bolster, we brought on an on-demand executive to help us think through and roll out a brand new product that we’re in the early days of testing right now. We’ve seen other CEOs use project-based work at the exec level for things like evaluating market expansion possibilities or speccing out the MVP of a potential new product.

This is just a short list of some of the possibilities where on-demand talent might support you in your business today. One of our favorite parts about this type of work is just that – the flexibility it offers to you and your team. Whether your business is just getting started or if you’re operating on all cylinders, don’t forget to consider on-demand work as part of your CEO toolkit for this year and beyond.

– Bethany Crystal, February 2, 2021

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Dec 8 2020

Introducing the Bolster Board Benchmarking Survey

Over the years,  I’ve had a list of nagging questions every time I’ve contemplated my board, but didn’t have anyone I could turn to who had deep, broad advice on this topic. Those questions were:

  • How big should my board be at this stage?  
  • How many independent directors should I have? 
  • What is the right profile of an independent director? 
  • How many options should I give a board member? 
  • How do I find the best, diverse, talent for my board openings?

That’s why Bolster is excited to announce the launch of our first CEO tool: Board Benchmarking. This application (which is free!) is the first of a series of tools that we’re designing to help CEOs understand the performance, design, and impact of themselves, their executive teams, and their boards. The results of this first application will shed light on the independence, diversity, and compensation of private company boards that’s never been available on a broad basis before.

Why are we starting with Board Benchmarking?

  1. Increasing Board Diversity is top of mind right now…
    …and that means CEOs need to have a handle on three things at the same time to get it right:  appropriate board size/number of independent seats, a talent pipeline that is diverse and well vetted, and clear compensation guidelines for independent directors.  Diverse employee populations and customer bases start with having a diverse board and a CEO (you!) who is attuned to the benefits of diversity at the top.  The longer you wait to prioritize diversity in the boardroom, the harder it becomes to change the makeup of your board. Culture becomes entrenched, recruiting becomes driven by referrals, and before you know it, everyone in an organization looks and thinks a little bit the same way. By capturing data on the diversity and composition of startup boards, we hope to offer an industry-wide snapshot to help CEOs start to have what can often be tricky conversations with their VCs about board size and composition as early as possible. And by pairing that with Bolster’s unique marketplace for diverse and vetted Board-ready talent, we hope to help CEOs slay all three dragons (number of independent seats, talent pipeline, and comp guidelines) at the same time.
  1. Private company board composition is notoriously tricky to benchmark.
    Unlike public companies, which are required to disclose the identities and compensation packages for their boards of directors, private board structure tends to remain…well, private! While this makes sense from a regulatory perspective, it often means private companies CEOs are taking a shot in the dark when it comes to things like when to add independent directors and how much to pay them. By aggregating and anonymizing thousands of data points across hundreds of private companies, we hope to (for the first time ever) provide CEOs with a very real, in-the-moment look at how their board today stacks up against others in similar cohorts.
  1. Filling an open board seat is a high-priority item for a CEO, and a tough one to get right.
    It’s said that good choices come from good options.  Early benchmarking results show that half of startup CEOs expect to fill an open board position within the next 12 months. Just as it’s critically important to get the right executives around your (well, now virtual) table, it’s equally, if not even more  important to build a board that effectively supports you, your company, and your customers. Every month that goes by with a board vacancy is another month where you’re potentially leaving valuable introductions and perspectives on the table. We hope that by exposing these board searches across such a broad subset of companies, we’ll also empower CEOs to take immediate next steps to fill those vacancies — including help recruiting multiple board candidates directly from the Bolster network.

As we conduct this survey over the next month, we’ll provide greater visibility into the size, composition, diversity, and director compensation of private company boards. We’re also establishing robust pipeline partnerships to amplify board-ready talent from organizations with diverse membership of African American, Hispanic/Latinx, and women orgs. So for anyone interested in adding qualified diverse talent to their boards, we’ll be ready.

Participants who complete the survey will receive early access to your benchmark results and a comprehensive guide to building and managing your Board of Directors. 

In early Q1, we’ll invite all participants of our Board Benchmarking survey to log in to Bolster and view their results interactively. CEOs will be able to see how their own boards stack up compared to others in the VC portfolio network or other cohorts. VC partners will be able to see patterns across the entire portfolio. 

Watch this space in the coming days and weeks for CEO-specific content about hiring Board members. 

We invite you to register as a Bolster client to participate in our Board Benchmarking survey today.

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