As we wrote in Bolster’s Founding Manifesto, one of the reasons we started Bolster was to create a new way; a faster, easier, and more cost-effective way, for startup and scaleup CEOs to grow their boards of directors and make them more diverse.

There’s a lot of research out there that the more independent a board is, the better it performs for companies — and that there’s a high degree of correlation between more independent boards and higher performing companies as well. There’s also a lot of research out there that shows that teams which have diversity of gender and race/ethnicity perform better. And everyone who has ever been on a high-functioning board of directors knows that a board is a team.

These facts are well known, yet it is still the case that most private company boards are overwhelmingly made up of founders and investors who are still largely white and male. I believe that the lack of independence and diversity on boards is a big miss for the whole startup ecosystem, and it’s a part of the startup game that we at Bolster want to help change.

Startup boards are tricky things. One of the very unique aspects of a CEO’s job that sets it apart from other executive positions is building and leading a board of directors. But most startup CEOs have either little or no experience building and leading a board, so that part of the job tends to default to a “because that’s the way I assume it’s always been done” kind of task. Of course, if you’re not intentional about building and managing a board, you’re likely to get lousy results. 

Building, shaping, and leading a world class board is one of the single most important things startup CEOs can do to help their businesses thrive and become industry leaders. It’s on par with building and leading an executive team. I’ve seen amazing companies held back by weak and ineffective boards and investor syndicates, and I’ve seen so-so companies succeed because the strategic advice, experience, and accountability coming out of the board room drives the management team in extraordinary ways.

So how is Bolster helping startup CEOs change the game with respect to Boards? We are doing three things. 

First, as you know, what gets measured gets managed. Our first-of-its-kind Board Benchmark application will soon produce an industry standard set of data around private company boards. You can’t find data on private company boards but we’ll soon have important data like size, composition (independents/management/investors), independent director compensation and diversity (gender/race-ethnicity/age). This will help answer questions that I know I have had many times over the years as a CEO such as 

• 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? 

Starting next week, we’re opening up our Board Benchmark application to any company who creates a free Bolster account. It will tell us a lot about the baseline across the ecosystem, and it will answer a lot of questions startup and scaleup CEOs have but can’t get answers to. Although this is an ongoing real-time benchmark tool, I’ll post some results here when we have enough critical mass to start reporting out.

Second, Bolster is in the talent business, and helping match VC-backed companies with a strong diverse slate of board candidates who are well-matched with their company is at the core of our business. We are already working on many searches for independent board members, and we’ll only be doing more of them as our client base and member base grow.

Finally, this blog post is the beginning of a whole series of posts about startup boards that we hope will demystify them a bit and help change the world’s thinking about how to grow them. Some of the material I will borrow from other blog posts I’ve written, or from the Board of Directors section of Startup CEO. Some will come from other influential VC and CEO bloggers and from Brad Feld and Mahendra Ramsinghani’s book Startup Boards. But much of the content will be new. And because Bolster is a two-sided marketplace, roughly half of the content will be aimed at startup CEOs and the other half at executives who are interested in serving on boards and aren’t sure how to get from where they are today into a board room. We’ll be sending out all the CEO posts as an eBook to CEOs who complete the Board Benchmark study, and all the Member posts as an eBook to Bolster members who fill out their Board profiles. I’ll post both of those eBooks here eventually as well.

For CEOs, the topics we will cover include 

• The purpose of a board
• Size and composition on boards
• Board evolution & turnover
• Diversity in the boardroom and the importance of appointing first-time directors
• What to look for in a director
• How to recruit and interview directors
• How to onboard directors, especially first time directors
• How to compensate directors
• How to build a director bench or Advisory Board
• How to evaluate your board

For executives searching for a board role, the topics we will cover include 

• What startup corporate boards look like
• How to prepare yourself to get on your first board
• Should you serve on an advisory board?
• How to interview for a Board role
• What you need to know about board compensation
• How to approach your first board meeting
• How to think about corporate governance as a board member
• How to be a great board member
• How to give advice or difficult feedback as a board member
• Making sure your voice is heard during a board meeting
• How to know if you’re doing a good job as a board member

We believe that boards can make or break a company and we intend to chart a new course for startup boards. I look forward to sharing thoughts and data with you on that topic in the weeks to come.

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.

(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.

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.

You, Too, Can Take Six Weeks Off

Note:  I have been really quite on OnlyOnce for a few months, I realize.  It’s been a busy stretch at work and at home.  I keep a steady backlog of blog topics to write about, and finally today I’ve grabbed a couple minutes on a flight to knock one out.  We’ll see if this starts me back on a more steady diet of blogging – I miss it!

I’ve written in the past about our sabbatical policy at Return Path, from what it is (here) to how much I enjoyed my own (here), to how great it is when my direct reports have been on Sabbatical so I can walk a few miles in their shoes (here and here).

But recently, a fellow CEO asked me if there was a special set of rules or advice on taking a sabbatical as a CEO.  My quick answer to his specific question was:

Well, first, you and your co-founder can’t take them at the same time. 🙂

But I have a longer list of thoughts as well.  It’s not easy, but as I’ve said many times, it’s important and wonderful.  Some tips:

• You have to make sure your balance sheet is strong and you’re not raising a round of financing
• You’re best off doing it a week or two after a Board meeting (and obviously, don’t miss one)
• You need everyone on your team to know about it and get excited for you!  They will rally/rise to the occasion more than you think
• You have to do a total disconnect, otherwise it doesn’t count.  Literally turn off email.  But make sure the team knows they can call you if there’s a true emergency
• Put someone in charge of keeping a running list of things that happened and be in charge of your “re-boarding”
• Put one person clearly in charge while you’re out, or tell your senior team that they’re responsible for collectively being in charge – either can work as long as you’re clear about it
• Be prepared to cancel or shift your plans if an emergency comes up before you leave

This last one is important.  I’ve postponed sabbaticals twice, and while it’s been a little tumultuous both at work and at home, it’s been better than going on a sabbatical and interrupting it with work, which I’ve also done.

Speaking of which…I’m coming up on my 17^th anniversary, which in our book means it’s time for another one!

(This is the second post in the series…….the first one on When to Hire your First Chief Revenue Officer is here.)

If you’re looking for a great CRO, one thing you want to avoid is being “sold” by a dynamic and engaging salesperson instead of finding the best CRO for your company. Over the two-plus decades of working closely with CROs I figured out what “great” looks like and I’ve found that there are five things that great CROs do. While you might not find all these characteristics and attributes in one person, you should definitely look for them!

First, a great CRO knows when to turn up the volume, and when not to.  Thinking through our metaphor/framework for enterprise sales that I wrote about in an earlier post – from Whiteboard to Powerpoint to PDF – great CROs know when they aren’t yet in PDF mode.  In the early days when your organization is selling on Whiteboard or figuring out the transition to Powerpoint, when you’re adding sales reps like crazy, this is not the time to quickly get to the PDF stage even though everyone in your organization will be clamoring for that. Sure, there could be a ton of opportunity to pursue but scaling quickly is inefficient and unlikely to be successful because scaling before the PDF stage still depends on the success of individual hunters.  Only when the organization has made the true transition to PDF can a sales machine scale rapidly, and a great CRO understands this.

Second, a great CRO gives credit to others first when things go well and looks inward first when things go poorly.  This is easier said than done because the tendency for people in any organization is self-preservation and the easiest way to do this is take credit and blame others. But the geat CROs are the first ones to thank their fellow executives in marketing, in product, in finance, for collaboration and successes.  They are also the first ones to thank their team publicly for a good quarter.  When they miss a quarter, the first thing they do is figure out why the Sales team blew it, as opposed to blaming the product or marketing or economy…or even customers themselves.

Third, a great CRO is maniacally focused on building a conveyor belt-style pipeline for sales talent so they don’t lose momentum when a rep quits or gets fired.  Notice that I didn’t say a great CRO was “focused” on building the pipeline or “passionate” about building the pipeline—I used the term “maniacal” because that’s what a great CRO looks like to everyone else in the organization: a crazy, intense, nonstop, extremist who religiously works on their talent pipeline.  “Quota just walked out the door” is never something you’ll hear from a great CRO because that’s not an option in a well-tuned sales machine where multiple layers of reps are consistently trained, managed, and groomed for the next level of selling. 

Fourth, a great CRO will be able to say “no” to overpaying and over-promoting without ruffling feathers on the sales team. An inability to stay disciplined on compensation is the second-worst thing a Sales leader can do and if they get compensation wrong by paying reps too much base or having too much commission in easily-repeatable form, you’ll pay for it—without the producivity gains. Reps who are overpaid get “fat and happy,” when what you want is for them to be “lean and hungry.” The worst thing a CRO can do? The worst thing a CRO can do, and something the great CROs won’t do despite great pressure, is to promote a superstar sales rep with no management aptitude or training into a sales manager role. I’ve seen this play out several times and it doesn’t end well. Either the superstar will not be able to lead and will exit the organization, or the superstar will end up poisoning an entire team and lots of your reps will exit the organization.  Great CROs know how to say no to the misguided request for a promotion and how to keep people engaged without overpaying them.

Fifth, a great CRO deosn’t belive in the “magic rolodex” (yes, I realize that term is a bit dated!). They might have a magic rolodex, deep networks, and personal ties to players in the ecosystem, but unless you are hiring a sales rep who literally just finished selling a competitive solution to the same target customer set, sales reps who claim they come with a built-in book of business can only deliver on that promise 1% of the time.  It’s alluring — but it just doesn’t work out that way.  Great CROs know how to ferret that out and hire instead the reps who will fit in the company culture and work to improve the processes and systems in place.

Hiring a great CRO isn’t easy but hiring the first (or last) person you interview because of their excellent communication skills will be a disaster. Look for a CRO who understands the pacing to scaling, is humble enough to give credit to others and avoid blaming, and who is “maniacal” about the team—coaching and mentoring them, providing the rails so that the team can do their best work.

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

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.

It’s fairly rare in a startup or scaleup that you, as a CEO or CXO (Chief [fill in the function] Officer) of any kind, will have significant one-on-one time with other members of the executive suite; instead, you’re most likely to spend time with the team in executive meetings, at offsites, or during all-company events. So, when you do get that one-on-one time it’s important to make sure that it’s not only productive, but that it builds a stronger relationship between you and the other person.

As a CEO I learned that the best way to help people grow and develop, and to further develop a better understanding of each other, is to engage with them in a mix of work and non-work settings.  By that I mean, working together on some aspect of their part of the business. Since each role and each person performing that role are different, there aren’t any hard and fast rules, but I thought I would create a series of posts that provide some ideas on things I’ve done to develop a better relationship, better team, and better company for each CXO in a company. 

I also have a whole series of posts related to each function on the executive team — CFO, CMO, CTO, etc.  So each post is part of two series.  This is the inaugural for both, and it’s quite fitting as Q4 is, for most companies, budgeting and planning season.  So today’s topic is How I engage with the CFO.

When I get the chance to spend time with my CFO I’ve found that we both get the most value working on several “problems” together. For example, we do Mental Math together where we look at key metrics and test them, improve them, or decide to scrap them. We are always attuned to key metrics and from time to time, we project them forward in our minds. What will happen to a key metric if our business scales 10-fold or if it declines 10-fold, for example. 

We are constantly checking to see that our financial and operating results mesh with our mental math.  When looking at our cash balance, we’ll look back at the last financial statement’s cash number and mentally work our way to the current statement: operating profits or losses, big swings in AR or AP, CapEx, and other “below the line” items. Do they add up?  Can we explain what we’re seeing in plain English to other leaders or directors?  The same thing applies to operating metrics — the size of our database, our headcount, our sales commission rate, and so on.

I’ve found that by working on the mental math that we actually come to understand the dynamics of the business far better than merely looking at the numbers or comparing the numbers. The mental math approach forces both you and the CFO to engage with the results, question them, and anticipate how slight changes can impact the company going forward. And once you get to that point, you have the ability to creatively think about how you want to go forward.  Here’s a simple example from the early days of Return Path.  One day, my long-time business partner and CFO Jack and I were doing mental math around how many clients each of our Customer Success team members was handling.  We had an instinct that it wasn’t enough — and we did a quick “how many of those reps would we need if we were doing $100mm in revenue” check and blanched at the number we came up with.  That led to a major series of investments in automation and support systems for our CS team.

Another way that the CFO and I work together is in a game called “spotting the number that seems off.” In any spreadsheet or financial analysis there is bound to be something that doesn’t seem quite right and for some uncanny reason, I am really good at finding the off number. I’m sure this has driven CFOs crazy over my career, but for whatever reason I have some kind of weird knack for looking at a wall of numbers and finding the one that’s wrong.  It’s some combination of instincts about the business, math skills, and looking at numbers with fresh eyes. It’s not an indictment on the CFO’s results and it’s not a “gotcha” moment but it’s part of the partnership I have with my CFO that improves the quality of our work and quantitative reasoning. My hunch is that looking at something with fresh eyes, as opposed to being the person who produces the numbers in the first place, makes it easier to spot something that’s not quite right. Kind of like an editor working with you on an article or book—they always seem to pick up and point out something that you didn’t see even though you spent hours creating it and hours more reading and re-reading something.

A third way to work with the CFO is to create stories with numbers. The best CFOs are the ones who are also good communicators — but that only partly means they are good at public speaking.  Being able to tell a story with numbers and visuals is an incredibly important skill that not all CFOs possess.  Whether the communication piece is an email to leaders, a slide at an all-hands meeting, or a Board call, partnering with a CFO on identifying the top three points to be made and coming up with the relevant set of data to back the number up — and then making sure the visual display of that information is also easy to read and intellectually honest, can be the difference between helping others make good decisions or bad ones.

Of course, a CFO could create stories on their own but like much of storytelling (like screenwriters for movies, plays, or sitcoms, for example), the creative storytelling usually happens with a team. In presenting financial data to others so that it makes an impact, so that it motivates them to take an action or change a behavior, a team approach is best and the CEO-CFO team can be much more effective than either one of them alone.

You won’t have a lot of time to spend 1:1 with any given CXO on your team, including the CFO, but you can make the time you spend together work to your favor in developing a stronger relationship between you and the CFO, and help you build a stronger company that can scale quickly. Without a deep understanding and strong relationship with others on your leadership team, your decision-making, speed, and risk-taking can suffer. Make sure every minute you spend with the CFO is productive. That’s why working on things together like mental math, spotting the off number, and storytelling, can be powerful ways to help you build a better company. 

(Also posted to the Bolster Blog).

I just did a podcast recording the other day for someone who asked me the biggest mistakes founders make and what to do about them. I divided my response into “early stage” and “later stage” founders. Here’s a summary of what I said about early stage founders.

1. They cling to a “good enough person” or someone who is a good performer but a weak cultural fit because they either feel beholden to that person for their output, or worse, they’re actually afraid of losing them because they’ll miss a milestone or maybe trigger some other departure.
   
   The “what to do” of course is to have courage and make the change! I wrote an essay years ago in Brad Feld and David Cohen’s book, Do More Faster, entitled Hire slowly, Fire quickly, in which I compared a poor cultural fit to a cancer that can infect the whole body of your company. A “good enough” person obviously isn’t quite that toxic, but someone like that can still prevent you from achieving your potential. In either case, the faster you realize what’s going on and make a move, the better off you are.
   
2. They get the balance wrong between “leading with vision” and “listening to customers”. Both are important for founders, but you can’t do too much of either. It’s really easy to get led to a too-narrow Product/Market Fit definition that has you building something awesome that only a dozen customers will be excited about That said, founders also have to listen if enough potential customers people say no. Your vision could just be too far ahead of the market.
   
   You have to get around this by constantly checking your enthusiasm with a mix of cold hard logic. Lots of market traction is great — but is all that traction coming from the same type of customer? Have you run your idea or wireframes by different segments, different buyers, different sizes of company (if B2B) or lots of different demographics (if B2C)? Are all of them equally enthusiastic and willing to buy? A complete lack of market traction when you’re sure your vision right is equally vexing. If literally everyone is saying “no” or worse, some polite but noncommittal version of yes, are you working to shape the vision, or at least shape how you articulate it? Sometimes your vision might be right, but your messaging might be off. Try different ones on for size.
   
3. They focus on fundraising and valuation over business fundamentals. Especially in this day and age, it’s really easy to get caught up in the “more money” hamster wheel. Raise, raise, raise. Finish one round, immediately start working on the next.
   
   In the end, business fundamentals matter — no fundamentals, no business (e.g., no next round). More than that, spend more time caring about your customers and learning and telling stories about how you made their lives better with your product or service. That’s more important to your next fundraise than just blowing through one round of money to get to the next.

Next week: the later stage founder answer (link won’t be live until 12/16/2021).

(Post 4 of 4 in the series on Scaling CMOs – other posts are, When to Hire your First Chief Marketing Officer, What Does Great Look like in a Chief Marketing Officer and Signs your Chief Marketing Officer isn’t Scaling)

Similar to interactions with all CXOs, you’ll have to capitalize on your moments but there are a few ways I’ve typically spent the most time or gotten the most value out of CMOs over the years.

 One of the key ways to engage with the CMO is to include them in meetings with the rest of the go-to-market (GTM) executives as a group, not in a silo.  While of course I have always had 1:1 meetings with my CMO, I find that the most valuable conversations are the ones with the GTM group as a group, talking about shared objectives and the underlying drivers and coordination points to get there. You might say, “Well, Matt, that’s true of all the GTM executives,” but I disagree. It’s even more important to have the CMO in the same room as the other GTM roles like Sales, Account Management, and Partnerships because marketing needs to be on the leading edge of GTM, not just a function working in a silo at the direction of the other GTM leaders. A lot of what happens in the GTM meetings is nuanced and since Marketing has to somehow make everything tangible, the earlier they hear about it and can start thinking about it the better off the whole company is.

On the other end of the spectrum, I find it very useful to create a thinking session with the CMO, where we take time away from the day-to-day to do deep dives on strategic topics like the company’s positioning, voice, or brand.  Sometimes I like to do these in the context of reading a relevant marketing book or business journal article, or after reading something I ran across on the internet, or something I learned at a conference—something that piqued my interest. Sometimes I don’t have a perspective or an idea, but the thinking session is valuable either way.  I find that the most creative thinking and ideas happen in some of these longer form, unstructured conversations. These sessions are not limited to ideas, positioning, or branding because even the quantitative part of marketing involves a lot of creativity. So, the thinking session can be wide open in terms of agenda, but it needs to be scheduled and done, otherwise all these ideas just ramble around and we don’t make as much progress.

Finally, a lot of my engagement with the CMO is actually a continuation of a longer relationship, before they become the CMO.  Let me explain what I mean. For years, we went through CMOs at Return Path at the same clip as other companies: every 1-2 years we’d make a change and bring in the new flavor-of-the-month CMO and we had a pattern of hiring them from the outside.  Over time, though, we realized that we would be much better served by having more continuity in marketing by investing in our own people and promoting them from within.  The last few CMOs we had at Return Path were all promoted into the role — so I got to know them pretty extensively ahead of time. I was not only thrilled to give them a shot at the top job, but I was in a great place to understand their strengths and weaknesses coming into the role so I could most effectively mentor them.  Of course, you can say the same thing for the other functional departments, but marketing is more acute based on the average tenure of CMOs.

(You can find this post on the Bolster blog here).

I wrote a post the other day about innovating employee benefits practices, and I realized I’d never documented a couple other ways in which we have always tried to innovate People practices. Here’s one of them: the Open Expense Policy, which I wrote about in the second edition of Startup CEO in a new chapter on Authentic Leadership when talking about the problem of the “Say-Do” gap.  Here’s what I wrote:

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

When we started Return Path, we had a similar policy. It was standard issue. But then over time as our culture became stronger and our People First philosophy and approach became something we evangelized more, we realized that traditional expense was at odds with our deeply held value of trusting employees to make good decisions and giving them the freedom and flexibility they needed to do their best work.

So we blew up the traditional policy and replaced it with a very simple one — “use your best judgment on expenses and try to spend the company’s money like it’s your own.” That policy is still in place today for our team at Bolster. We do have people sign off on expense requests that come in through the Expensify system, mostly because we have to, but unless there is something extremely profligate, no one really says a word.

Similar to what happened when we switched to an Open Vacation policy, we had some concerns from managers about employees abusing the new un-policy, so we had to assure them we’d have their back. But do you know what happened when we implemented the new policy? We got a bunch of emails from team members thanking us for trusting them with the company’s money. And the average amount of expenses per employees went down. That’s right, down. Trusting people to exercise good judgment and spend the company’s money as if it was their own drove people to think critically about expenses as opposed to “spend to the limit.”

I don’t think in 15+ years of operating with an Open Expense policy that any of us have had to call out an employee’s expenses as being too high more than once or twice. That’s what the essence of employee trust is about. Manage exceptions on the back end, don’t attempt to control or micromanage behavior on the front end.