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!

Give the Gift of a 360 to Your Board of Directors

I recently ran our biennial Board 360, and I thought it would be interesting to share the details.  Attached are a few pages from, my book, Startup CEO:  A Field Guide to Scaling Up Your Business  which describe the process as well as share the survey I developed, which I adapted from one that the legendary Bill Campbell uses at larger public companies like Intuit.

If you’ve read this blog a lot over the years, you know that we are big on 360s for staff at all levels at Return Path , and at some point a few years ago, I thought, “hmmm, shouldn’t we do this for the Board as well?”

Most of our directors had never been part of one before as Board members, and they reacted to it with varying levels of interest and trepidation.  But all of them loved the output and the discussion we had afterwards.  Extending the level of transparency we have internally to the Board was a great thing and a great use of time, and I think making the Board members review themselves and their peers critically and then seeing the results sharpened overall Board performance.

The document also shares the survey we use, which we have each director take anonymously and compile the results to share in Executive Session at a Board meeting.  We also ask a few members of the senior management team to fill out the survey as well so the Board gets feedback from them, too.

5 Ways to Get Your Staff on the Same Page

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

When a major issue arises, is everybody at your company serving the same interests? Or is one person serving the engineering team, another person serving the sales team, one board member serving the VC fund, another serving the early-stage “angels” and another serving the CEO? If that’s the case, then your team is misaligned. No individual department’s interests are as important as the company’s.

To align everyone behind your company’s interests, you must first define and communicate those goals and needs. This requires five steps:

1. Define the mission. Be clear to everyone about where you’re going and how you’re going to get there (in keeping with your values).
2. Set annual priorities, goals, and targets. Turn the broader mission into something more concrete with prioritized goals and unambiguous success metrics.
3. Encourage bottom-up planning. You and your executive team need to set the major strategic goals for the company, but team members should design their own path to contribution. Just be sure that you or their managers check in with them to assure that they remain in synch with the company’s goals.
4. Facilitate the transparent flow of information and rigorous debate. To help people calibrate the success, or insufficiency, of their efforts, be transparent about how the organization is doing along the way. Your organization will make better decisions when everyone has what they need to have frank conversations and then make well-informed decisions.
5. Ensure that compensation supports alignment (or at least doesn’t fight it). As selfless as you want your employees to be, they’ll always prioritize their interests over the company’s. If those interests are aligned – especially when it comes to compensation – this reality of human nature simply won’t be a problem.

Taken in sequence, these steps are the formula for alignment. But if I had to single out one as the most important, it would be number 5: aligning individual incentives with companywide goals.

It’s always great to hear people say that they’d do their jobs even if they weren’t paid to, but the reality of post-lottery-jackpot job retention rates suggests otherwise. You, and every member of your team, “work” for pay. Whatever the details of your compensation plan, it’s crucial that it aligns your entire team behind the company’s best interests.

Don’t reward marketers for hitting marketing milestones while rewarding engineers to hit product milestones and back office personnel to keep the infrastructure humming. Reward everybody when the company hits its milestones.

The results of this system can be extraordinary:

• Department goals are in alignment with overall company goals. “Hitting product goals” shouldn’t matter unless those goals serve the overall health of your company. When every member of your executive team – including your CTO – is rewarded for the latter, it’s much easier to set goals as a company. There are no competing priorities: the only priority is serving the annual goals.
• Individual success metrics are in alignment with overall company success metrics. The one place where all companies probably have alignment between corporate and departmental goals is in sales. The success metrics that your sales team uses can’t be that far off from your overall goals for the company. With a unified incentive plan, you can bring every department into the same degree of alignment. Imagine your general counsel asking for less extraneous legal review in order to cut costs
• Resource allocation serves the company, rather than individual silos. If a department with its own compensation plan hits its (unique) metrics early, members of that team have no incentive to pitch in elsewhere; their bonuses are secure. But if everyone’s incentive depends on the entire company’s performance, get ready to watch product leads offering to share developers, unprompted.

This approach can only be taken so far: I can’t imagine an incentive system that doesn’t reward salespeople for individual performance. And while everyone benefits when things go well, if your company misses its goals, nobody should have occasion to celebrate. Everybody gets dinged if the company doesn’t meet its goals, no matter how well they or their departments performed. It’s a tough pill to swallow, but it also important preventive medicine.

Startup CEO “Bibliography”

A couple people who read Startup CEO:  A Field Guide to Scaling Up Your Business asked me if I would publish a list of all the other business books I refer to over the course of the book.  Here it is — I guess in some respects an all-time favorite list for me of business books.

• The Lean Startup by Eric Ries
• The Four Steps to the Epiphany by Steven Gary Blank
• Running Lean by Ash Maurya
• The Entrepreneur’s Guide to Customer Development: A Cheat Sheet to the Four Steps to the Epiphany by Brant Cooper and Patrick Vlaskovits
• Profitable Growth Is Everyone’s Business by Ram Charan
• The Innovator’s Dilemma by Clay Christensen
• The Innovator’s Solution by Clay Christensen
• Purple Cow by Seth Godin
• The Goal by Eliyahu M. Goldratt
• It’s Not Luck by Eliyahu M. Goldratt
• Blue Ocean Strategy by Chan Kim and Renee Mauborgne
• Crossing the Chasm by Geoffrey Moore
• Inside the Tornado by Geoffrey Moore
• Escape Velocity by Geoffrey Moore
• Climbing Mount Improbable by Richard Dawkins
• Topgrading by Brad Smart
• The One Minute Manager by Ken Blanchard
• Whale Done by Ken Blanchard
• High Output Management by Andy Grove
• Three Signs of a Miserable Job by Patrick Lencioni
• The Five Temptations of a CEO by Patrick Lencioni
• The Four Obsessions of an Extraordinary Executive by Patrick Lencioni
• Death by Meeting by Patrick Lencioni
• The Advantage: Why Organizational Health Trumps Everything Else in Business by Patrick Lencioni
• Hardball by George Stalk and Rob Lachenauer
• The Seven Habits of Highly Effective People by Stephen Covey
• The Eighth Habit by Stephen Covey
• Good to Great by Jim Collins
• Built to Last by Jim Collins

And here’s the list of books in Brad Feld’s Startup Revolution series other than Startup CEO:

• Startup Communities: Building and Entrepreneurial Ecosystem in Your City by Brad Feld
• Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur by Brad Feld and Amy Batchelor
• Startup Metrics: Making sense of the numbers in your startup by Brad Feld (not yet published)
• Startup Boards: Getting the Most out of Your Board of Directors by Brad Feld and Mahendra Ramsinghani
• Venture Deals by Brad Feld and Jason Mendelson
• Do More Faster: TechStars Lessons to Accelerate Your Startup by Brad Feld and David Cohen

(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 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)

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.

Over the past several months, I’ve published two series of posts on the Bolster blog about Boards. The first series is designed to help CEOs better understand how to build, diversify, and scale their boards of directors. I’ll write about the second one next week. Both series of posts will feature in the second edition of Startup Boards, a book originally published in 2014 by Brad Feld and Mahendra Ramsinghani. The second edition, which is also co-authored by me, will be out late this year or early next year.

As I’ve gone about building our business at Bolster, including leading several dozen board searches for companies of all sizes and stages from pre-revenue to public, I’ve noticed that there are still a lot of questions among company leaders about board-building best practices. Without a lot of documentation and analysis about private company boards, most startup CEOs learn about building and managing boards through trial and error. As a result, this critical component of corporate governance is often under-utilized. Directors’ skills and networks are under-leveraged, term lengths are rarely re-negotiated, and board diversity becomes an afterthought.

This is why I set out to publish a comprehensive look at building boards, written from one CEO to another. You can read the full series here:

• The New Way to Scale A Board of Directors
• The Purpose of a Board
• Size and Composition of Boards
• Board Evolution and 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 Independent Directors
• How to Build a Director Bench or Advisory Board
• How to Evaluate Your Board

The team at Bolster also compiled all of these posts into an eBook you can download by clicking on this link, entitled How to Build Your Board. No matter where you are in your journey as a CEO or company leader, I hope this is a resource and reference for you to look back on over time.

By the way – if you’d like to get access to more content like this or start a search for an independent director for your own board, you can sign up as a Bolster client 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).