Aug 4 2022

Our Operating Philosophy – the Mostly Self Managed Organization (MSMO)

Last week, I wrote about the concept of the Operating Philosophy, and how it fits with a company’s Operating Framework and Operating System and defines the essence of who you are as a company…what form of company you are.

While we had a loose Operating Philosophy at Return Path, we never really crisply articulated it, and that caused some hand-wringing at various points over the years, as different people interpreted our “People First” mantra in different ways. So this time around at Bolster, we’re trying to be more intentional about this up front. We have labeled our company a “Mostly Self Managed Organization” or MSMO (pronounced Miz-Moh). We made those up.

Our Operating Philosophy – we are a Mostly Self-Managed Organization, or MSMO (pronounced Miz-Mo, a term we just made up). The MSMO is the product of years of work, research, practical learning, and thinking on our part.  Self-Management has been important to me my whole career as a manager and leader.  Over the last 15 years, the team and I have studied various forms of self-management with interviews and onsite meetings at Netflix, Gore, Nucor, Morningstar, and Zappos.  While we implemented some aspects of it at Return Path, we are trying to take the implementation a step further here at Bolster from the beginning.

Of all those companies, what we’re doing is probably closest to the Operating Philosophy of W.L. Gore & Associates, which you can find written out online without a name but with the description that “individuals don’t need close supervision; what they need is mentoring and support.” The embodiments of the Operating Philosophy at Gore may be different from those we create at Bolster, but the essence of the philosophies is pretty similar.

Why a MSMO?  We employ smart people, and smart people crave autonomy, purpose, and mastery (according to Daniel Pink) and do their best work when they have those things in alignment.  

So, how do we define self-management at Bolster?  We aren’t going to be a DAO.  I don’t think that model works for a for-profit multifaceted corporation – complete Self-Management is too chaotic.  Leadership and mentorship matter and make a difference in guiding strategy, critical decisions, and careers. Holocracies or other unnamed structures like that of Morningstar are ok, but they are so rigidly ideological that they require an immense amount of work-around, or scaffolding, to be practical.

But we aren’t a traditional fixed top-down hierarchy, either.  We are going to run the business in a way that lets people co-create their work and be responsible for driving their own feedback and development with a support structure.  That’s the ideology we have. Letting talented people loose to do their best work is critical; but leadership, judgment, and experience matter, too. If not, why bother having a CEO, or a VP of anything? Why not just pay everyone the same thing and hope they can all figure out the complexities of the business together?

We believe the MSMO is the best operating philosophy to allow high performers to do their best work. 

At Bolster, we are leaning into things like social contracts, peer feedback, career mentorship, individuals translating our Operating Framework into priorities and work, flexible work streams and team leadership, instead of fixed permanent hierarchies, rotating chairs of key company meetings, and market-level-based compensation.  

What we are steering away from are things like traditional titles, micromanaging or overmanaging, traditional performance reviews linked to compensation and complex incentive compensation structures, and fixed organization boundaries and structure.

We’ll see if our MSMO Operating Philosophy works. If not, we’ll iterate on it. That’s the good thing about adherence to an ideology of philosophy as opposed to an ideology of practices. Who knows – maybe the MSMO concept and even its quirky name will catch on!

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Jul 28 2022

The Concept of the Operating Philosophy

I’ve always been a big believer in the Operating Framework and the Operating System as two of the management underpinnings behind every well run company.

The Operating Framework is the company’s Mission, Vision, Values, Strategic Objectives, and Key Metrics. Companies have all sorts of different labels for this, from Balanced Scorecard to Salesforce’s V2MOM to Patrick Lencioni’s 6 Questions. It’s what you have to define up front, refresh annually, and tweak quarterly so that people in the company are aligned and know where you’re going.

The Operating System, as I wrote extensively about in Startup CEO, is the collection of practices, meetings, mailing lists, routines/rhythms, and behaviors that your company and team use and depend on to run the business on a day to day basis. It’s what you have to put in place and tweak as needed so work gets done efficiently – the thing that turns the sprint of a raw startup into the marathon of a scaling business.

But there’s a third leg to the stool of company management underpinnings that’s often overlooked and underappreciated – the company’s Operating Philosophy. The Operating Philosophy is the intellectual underpinning of how you want to run and lead the business. It’s related to, but different from, your company’s values. Think of it as the essence of how you want to work and shape the work of others…what defines your form of company.

You can run a company perfectly well without a clear Operating Philosophy, especially with a tight Operating Framework and Operating System in place. But my guess is that you have one, you just haven’t articulated it yet, and you might benefit from doing so. At least that was our experience where we had an undefined but real one at Return Path and have now tried to define one front and center at Bolster.

A useful way to think about these three legs of the stool is the analogy of government (bear with me on this and pretend like our government in the US isn’t quite as dysfunctional as it is at the moment). Our Operating Framework is the Constitution – it lays out the broad contours of what our government does. Our mission, vision, and values. Our Operating System is the collection of policies, practices, and programs that run the country, from the timing and cadence of elections, to the ways the three branches of government enact and execute policy, to the ways state and local governments fit in. Our Operating Philosophy is the Declaration of Independence. It’s our essence. It is what separates our form of government from other forms of government. We are a Representative Democracy, a Constitutional Federal Republic. We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness. That to secure these rights, Governments are instituted among Men, deriving their just powers from the consent of the governed.

Some examples? Zappos is a Holocracy – defined as a system of corporate governance whereby members of a team or business form distinct, autonomous, yet symbiotic, teams to accomplish tasks and company goals. The concept of a corporate hierarchy is discarded in favor of a flat organizational structure where all workers have an equal voice while simultaneously answering to the direction of shared authority. Patagonia (and lots of other companies) is a Delaware Public Benefit Corporation (PBC or often called a B Corporation), which must by law follow Stakeholder Capitalism and not Shareholder Capitalism. Plenty of crypto organizations are set up as DAOs (Decentralized Autonomous Organizations), which is a group of people who come together without a central leader or company dictating any of the decisions, built on a blockchain using smart contracts and a currency of tokens that give them the ability to vote on decisions that are made around how the pool of money is spent and managed.

Hopefully that makes sense. Next week, I’ll talk about our Operating Philosophy at Bolster.

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Jul 21 2022

Giving Away Credit – Added Rationale

I just finished up a coaching call with a late-stage CEO client, and we were talking about a situation where he helped tee up a couple successes for a new senior executive on his team and then promptly gave the exec credit for the successes. That’s good form as a leader – you take the blame when things go wrong but give away credit when things go well.

But my client articulated a selfish reason to this that goes beyond the “good leadership form” argument that I’d never thought of before:

“When you give them the credit, you win twice.”

What he meant by that is that you get your first win when you bolster the person on your team by giving them the win. And you get your second win when others (the rest of the team, your board, etc.) see the goodness that happened and realize that it happened on your watch as the CEO — either by hiring the person who got the credit, or by orchestrating the broader scenario.

After all, who doesn’t want to win twice?

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Jul 14 2022

Second Lap Around the Track

I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap.

Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is different from those same things in first-time founders. Not every single multi-time founder has every single one of these traits, but they all have a majority of them and form a pretty common pattern. I’ve noticed this with non-profit founders as well as for-profit ones.

  • They have an Easier Time Recruiting team members and investors. That may sound obvious, but there are significant benefits to it. They also tend to have Much Cleaner Cap Tables, because they lived the horrors of a messy cap table when they exited their last company without thinking about that topic ahead of time!
  • They have a Big Vision. Once you’ve had an exit, whether successful or not or somewhere in between, you don’t want to focus on something niche. You want to go all-in on a big problem.
  • They are interested in creating Portfolio Effect. A number of repeat founders want to start multiple business at the same time, are actually doing it, or are creating some kind of studio model that creates multiple businesses. Once you have a big team, a track record with investors, and a field of deep expertise, it’s interesting to think about creating multiple related paths (and hedges) to success.
  • They are driving to be Efficient in Execution and Find Leverage wherever they can. One multi-time founder I talked to a few weeks ago was bragging to me about how few people he has in his finance team. At Bolster, our objective is to build a big business on a small team, looking for opportunities to use our own network of fractional and project-based team members wherever possible.
  • They are Impatient for Progress. While being mindful that good software takes time to build no matter how many engineers you hire, repeat founders tend to have fleshed out their vision a couple layers deep and are always eager to be 6 months ahead of where they are in terms of execution, which leads me to the next point, that…
  • They are equally Impatient for Success (or Failure). More than just wanting to be 6 months ahead of where they are in seeing their vision come to life, they want to get to “an answer” as soon as possible. No one likes wasting time, but when you’re on your second or third company, you value your time differently. As a friend of mine says in a sales context, “The best answer you can get from a prospect is ‘yes’ – the second best answer you can get is a fast ‘no’.” The same logic applies to success in your nth startup. Succeed or Fail – you want to find out fast.
  • They are Calm and Comfortable in Their Own Skin. At this stage in the game, repeat founders are more relaxed. They know their strengths and weaknesses and have no problem bringing in people to shore those things up. They know that if things don’t work out with this one, there’s more to life.
  • They are stronger at Self Management. They are more efficient. They exercise more. They sleep more. They spend more time with family and friends. They work fewer hours.

Anyone else ever notice these traits, or others, in repeat founders?

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Jul 7 2022

What a CEO Should Do

Fred Wilson wrote an iconic blog post years ago entitled What a CEO does. In it, he outlined three broad themes:

A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.

I wrote a response in a post entitled What Does a CEO Do, Anyway?, in which I added some specificity to those three items and added three key behaviors of successful CEOs. I also added to Fred’s list when I wrote Startup CEO, CEOs have to build and lead a board of directors, CEOs have to manage themselves, and CEOs ultimately have to think about and execute exits.

But recently, as I’ve been coaching a few CEOs, I’ve answered the question differently, because the questions have been a little less about the broad themes and more about how to prioritize — how to know what NOT to do. So in addition to Fred’s wisdom and my other thoughts above, here’s the answer I’m giving CEOs these days:

  • First, do what you MUST do. There are some things that are in your job description. Do them first. You have to run your board meeting. You have to pitch investors. You have to write performance reviews for your direct reports.
  • Second, do what ONLY YOU can do. There are also some things that, while not in your job description, are things that CEOs and/or founders have special impact when they do. No one can call a team member who just lost a parent or spouse and offer support and sympathy like you can. No one can get on a plane and save a key customer from leaving you like you can. No one can congratulate a sales rep on a key win like you can.
  • Third, do what you’re BEST IN CLASS at. Finally, there are things that may be in other people’s job descriptions, but where you’re the stronger executer. I remember reading years ago that Bill Gates, long after he even stopped being CEO of Microsoft and was Chairman, still got involved in some major technical architecture decisions and reviews. Whatever your superpower is, or whatever it was when you were in your pre-CEO jobs, there’s no reason not to jump in and help your team excel at (and ideally train/mentor them) whenever you can.

After that, you can fill in the rest of your time with other tasks. In the world of Covey’s big rocks, this is all the sand. All the other things that come by your desk or inbox that people ask of you. They are the least important. Hopefully this is another helpful lens on how CEOs should spend their time.

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Jun 30 2022

Book Short: Loved Loved

I enjoy reading books written by people I know. I can always picture the person narrating the book, or hear their voice saying the words, I can periodically see their personality showing through the words on the page, and books bring out so much more detail than I’d ever get from a conversation. Loved: How to Rethink Marketing for Tech Products, by Martina Lauchengco, is one of those books. Martina is an operating partner at Costanoa Venture Capital, an investor in both Return Path and Bolster, and I’d known Martina for several years before she joined Costanoa through Greg Sands. She’s the best product marketer on the planet. She’s the also one of the nicest people around.

Product Marketing is a tricky discipline. A brand marketer on my leadership team years ago referred to it somewhat derisively as a “tweener” function, one of those things that’s not quite marketing and not quite product. We didn’t get the function right for many years at Return Path because we treated it that way, thinking “well, it’s neither fish nor fowl, so we’re not quite sure what to do with it.” Then we hired Scott Roth, who has gone on to have a storied career as a multi-time CEO. Scott’s background was in product marketing. He said to me in his interview process, “Product Marketing isn’t a tweener function with no home. It’s a glue function. It holds product and marketing together.” It’s amazing how that simple change in framing, combined with great leadership, led us to completely rethink the function and make it one of the most important functions in the company.

Martina brings that to live with Loved. Simply put, Loved is a handbook or a field guide to running the Product Marketing function. I can imagine it being a section of Startup CXO in that way — it’s incredibly practical, hands-on, how-to, and rich with examples from Martina’s amazing career at Microsoft, Netscape, Silicon Valley Product Group, and Costanoa. And she believes in Agile Marketing, which is always a plus in my book (and I find rare in marketers).

Martina has lots of great frameworks and stories in the book – key responsibilities of product marketing, key metrics, the release scale, the connection to Geoffrey Moore’s TALC, strategies for messaging, pricing and packaging, and more. I won’t spoil more than one here, but I will paraphrase one that I found particularly impactful, a bit of a checklist on the essence of great product marketing:

  • Share data around shifting trends in buyer behavior
  • Connect your product’s purpose with broader trends
  • Rebrand to make your product seem bigger than it is (and save room for expansion down the road)
  • Make it free, especially if you’re defining a new category
  • Share the “why” and advance access with influencers

If the measure of a book’s impact is how many pages you dog ear or highlight, this says it all about Loved.

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Jun 23 2022

Two Great Lines (and One Worrisome One) About the Current Macroeconomic Situation

I was trading emails a few weeks ago Elliot Noss from Tucows about the current state of the economy after being on a panel together about it, and he wrote:

The market is fascinating right now. Heated competition AND layoffs and hiring freezes. It feel like an old European hotel where there are two faucets, one is too hot and the other too cold.

While a quick rant about European hotel bathrooms could be fun…we’ll just stick to the sink analogy. As anyone who has ever tried to use one of these sinks that Elliot describes knows, they’re hard to use and illogical. Sure, sometimes you want freezing water and sometimes you want scalding water (I guess), but often, you want something in between. And the only way to achieve that is to turn on both freezing and scalding at the same time? That’s weird.

Then I was on another email thread recently with a group of CEOs, when John Henry from Ride With Loop said this:

Whatever the climate, we all surely agree there is no bad time to build a good business.

How true that is!

But here’s the worrisome part. It’s impossible to predict what’s going to happen next. We are in uncharted territory here with a land war in Europe, a partial global oil embargo of a top tier oil producer, a pandemic, supply chain problems, etc. etc. There are days and circumstances where everything feels normal. Plenty of businesses, especially in the tech sector, are kicking ass. And yet there are days and circumstances that feel like 2001 or 2009. It’s tough to navigate as a startup CEO. Yes, it’s obvious you should try to have a couple years of cash on hand, and that you should be smart about investments and not get too far ahead of revenue if you’re in certain sectors (presumably if you’re in an R&D intensive field and weren’t planning to have revenue for years on end, life isn’t all that different?). But beyond that, there’s no clear playbook.

And that’s where the worrisome line comes in. I saw Larry Summers on Meet the Press last weekend, who predicted that

a recession would come in late 2023.

Wait, what? Aren’t things messed up now? Yes, inflation is high, the stock market is down, and interest rates are creeping up. But the economy is still GROWING. Unemployment is still LOW. Summers’ point is a reminder that contraction is likely, but it may still be a ways off, it depends how the Fed handles interest rate hikes (and about a zillion other things), and it’s impossible to predict. That was more worrisome to me. If we’re navigating choppy waters now, it may not just be for a couple of quarters. It may be that 4-6 quarters from now, we are in for 2-3 quarters of contraction. That is a more than most companies are able to plan for from a cash perspective.

Frothy macro environments lead to bad businesses getting created, too many lookalike businesses popping up, or weak teams getting funded. When the tide goes out, as they say, you can see who is swimming naked. But if you’re building a good business, one that has staying power and a clear value proposition, with real people or clients paying real money for a real product or service, and if you’re serious about building a good company, keep on keeping on. Be smart about key decisions, especially investment decisions, but don’t despair or give up.

We’ll all get through this.

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Jun 15 2022

Startup Boards, the book, and also why they matter more than ever these days

My latest book (I’m a co-author along with Brad Feld and Mahendra Ramsinghani), Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, is now live on Amazon – today is publication day! The book is a major refresh of the first edition, now eight years old. I was quoted in it extensively but not an official author – Brad and Mahendra were nice enough to share that with me this time. The book includes a lot of new material and new voices, including a great Foreword by Jocelyn Mangan from Him for Her and Illumyn. It’s aligned with Startup CEO and Startup CXO in look and in format and is designed to be an easy-to-read operator’s manual to private company boards of directors. Brad also blogged about it here.

We’ve done a lot of work around startup boards at Bolster the past couple of years, including working with over 30 CEOs to help them hire amazing new independent board members. Our landmark Board Benchmark study last year highlighted the problem with startup boards, but also the opportunity that lies within: not enough diversity on the boards, but also not nearly enough independent directors — and a lot of open seats for independent directors that could be filled. That conclusion led me to my Startup Board Mantra of 1-1-1: Independent directors from Day 1, 1 member of the management team, and 1 independent for every 1 investor.

As we posted on the Bolster blog last week, our quick refresh of the Board Benchmark study revealed some good news and some bad news about progress on diversity in the boardroom with startups. The good news is that the needle is starting to move very slowly, and that independent directors present the best opportunity to add diversity to boards. Our data shows that half of all new directors brought onto boards in the last year were independents, and of those, 57.9% were women and 31.6% were non-White board members. Those numbers are well above the prior study’s benchmarks of 36% and 23%, respectively (our experience running board searches skews even further to women and non-White directors being hired).

The bad news is how slowly the needle is moving — only 20% of open independent board seats were filled over the previous year, which is a lot of missed opportunity. The main takeaway is that while overall representation on boards is still skewed largely White and male, the demographic profile of new board appointments looks a lot different from the representation on boards today, indicating that CEOs are making intentional changes to their board composition.

Startup boards are a great way to drive grassroots change to the face of leadership in corporate America. More CEOs need to follow up by filling their open board seats and fulfilling their stated desires to improve diversity in the boardroom. This takes time and prioritization — these are the places where we see board searches either never get off the ground, or falling down once they do, for all the searches we either run or pitch at Bolster.

Hopefully Startup Boards will help the startup ecosystem get there.

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Jun 9 2022

Open All-Hands Meetings

I love stealing/borrowing other people’s good ideas for management and leadership when they’re made public, and I always encourage others to do so from me. I call it “plagiarizing with pride.” So I was intrigued when I saw a new way of doing all-hands meetings published by my friend Daniel Odio (DROdio) on his founder community called FounderCulture. You can see the original post here.

We’ve experimented with different formats and cadences for all-hands meetings over the years. They tend to vary with the size of the company and complexity of the material to cover. Larger companies usually fall into the rhythm of doing quarterly all-hands meetings sometime after the end of the quarter, usually around a Board meeting, with a quarterly recap and forecast for next quarter.

But for early stage companies, there’s no tried-and-true method. We struggled with that for a while at Bolster. Weekly felt too much. Quarterly felt like too little. It seemed weird for me or my co-founders to just have a meeting where we talked at everyone…and it also seemed weird to just host an “open mic night” type meeting. Then I saw DROdio’s video, and we adapted it. It’s working pretty well for us. Here’s what we do in what we’re calling our Open All-Hands Meeting:

  • We hold an all-hands meeting every Monday for :30
  • A different team member is responsible for being the host/chair/emcee for each meeting
  • We run the meeting off of a dedicated Trello board with specific columns of information. Everyone is invited to contribute to the Trello board in the days leading up to the meeting. The columns are:
    • Values-Kudos-Good News: Anyone can call out anyone for doing something that demonstrates one of the company’s values, that is just a big thank you, or that is some other piece of karmic goodness they want to share
    • Wins: All client wins are shown here with some detail, each in its own card with its owner highlighted
    • #MAD: This is where we trade items on which we Made A Decision during the prior week, big or small. We’ve always struggled with the best way to keep everyone informed on things like this…and this works really well for that purpose
    • Learnings/Product Ideas: Anyone can populate this with anything they want as they go about their work and either come across learnings or product ideas they want to share
    • Announcements: Pretty self-explanatory, any corporate announcement, new employee introductions, etc.
    • Swim Lane Updates: Each we, we ask one or two of our functional or project areas to do a deep dive update — Product, Finance, Sales, Marketing, Ops, etc. — and this is also where we’ll do product demos of newly released functionality
    • Permanent Items: this isn’t a column that’s read…it just warehouses things we want on the board like the schedule of hosts, schedule of swim lane updates, instructions for running the meeting, recordings of prior meetings
    • BOLSTER 2022: this isn’t a column that’s read…it contains our mission, values, strategy, and key strategic initiatives and metrics for the year
    • Archive: this isn’t a column that’s read…it just contains the prior week’s items
  • There’s a series of light integrations between Slack, Hubspot, and Trello to automatically populate Trello based on certain channels, keywords, and emojis. Every week, the board is automatically wiped clean after the meeting
  • The host moves the meeting from column to column and card to card, sometimes reading the cards, and sometimes asking the person who submitted the card to read it or give color commentary on it
  • I do jump in from time to time, as do some of my co-founders or our other leaders, to give extra commentary or amplify something or help connect the dots. But that’s about as formal as my role gets other than…
  • …when we do have a quarterly board book and board meeting, I host that one meeting and recap the meeting, ask other leaders to comment on specific topics, and facilitate Q&A on the materials we send out ahead of time. So I’m hosting 4 meetings per year
  • The host can add a personal touch to any meeting. Custom wallpaper for the Trello board. Asking everyone in the company who has a pet to send in a photo of the pet ahead of time and introducing their furry friends during the meeting. Playing intro or outro music to fit the occasion. Doing spot surveys or game show questions to keep things lively. Interviewing new team members. Asking everyone to do a one-sentence “here’s what I’m working on this week” at the end of the meeting
  • Finally, the host passes the baton from one person to the next each week. No one can escape this responsibility!

In addition to the Open All-Hands Meeting format, I send the company an email every Friday with some musings on the prior week. The content of these varies widely – from “what I did last week,” to “here’s something I saw that’s interesting,” to welcoming new team members with their bios, to customer testimonials. Sometimes other founders write these. They’re a good way to add a personal touch to the operating system of the company — and we also send these to our board and major shareholders every week so they, too, can keep a finger on the pulse.

These two things together are proving to be a good Operating System for keeping everyone informed, aligned, and connected on a weekly basis.

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Jun 2 2022

Book Short: New to the Canon of Great CEO Books

Please go put Decide and Conquer: 44 Decisions that will Make or Break All Leaders by David Siegel on your reading list, or buy it. David’s book is up there on my list with Ben Horowitz’s The Hard Thing About Hard Things. It’s a totally different kind of book than Startup CEO, and in some ways a much better one in that there’s a great through-line or storyline, as David shares his leadership framework in the context of his journey of getting hired to replace founder Scott Heiferman as Meetup’s CEO after its acquisition by WeWork, including some juicy interactions with Adam Neumann, through the trials and tribulations of WeWork as a parent company, through COVID and its impact on an in-person meeting facilitator like Meetup, through to the sale of Meetup OUT of WeWork.

It’s hard to do the book justice with a quick write up. It’s incredibly concise. It’s clear. It’s witty. Most of all, it’s very human, and David shares a very human, common sense approach to leadership. I particularly like a device he uses to reinforce his main points and principles by bolding the key phrases every time they show up in the book: be kind, be confident, be bold, expand your options, focus on the long-term picture, be pragmatic, be honest, be speedy, do what’s right for the business, work for your people and they’ll work for you, be surprised only about being surprised. These all resonate with me so much.

One of the interesting things about the book is that David is a CEO, but not a founder (although he was sort of a re-founder in this case). A lot of CEO books talk about how to run a company, or give stories from the trials and tribulations thereof, but few focus on the elements of interviewing for the CEO job, or taking over the reins of a company in the midst of a turbulent flight. So the book is about getting the job, starting the job, doing a turnaround, leading a company through growth, a buy-out, and managing a company inside of another company. And because Meetup is such an iconic brand and business, it’s easy to understand a lot of the backdrop to David’s story.

I just met David for the first time a few weeks ago. We knew a bunch of people in common from his DoubleClick days. We instantly hit it off and traded copies of our books, and then were reading them at the same time trading emails about the parts that clicked. I just can’t recommend the book enough to any CEO or founder. In my view, it joins a pretty elite canon.

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May 26 2022

Signs Your CFO Isn’t Scaling

Post 4 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO, When it is Time to Hire Your First Chief Financial Officer, and What Does “Great” Look Like in a CFO?)

While all the functions of a team are needed, perhaps the most critical function to make sure your company is able to scale is the CFO. Cash flow, investments into the business, compensation, budgets—nearly everything that happens in a company flows through the CFO—and it should. So, getting this role right is one of the most important tasks of any startup team. But how do you know if your CFO is up to the task of scaling?

For CEOs, one of the first things that’s a telltale sign is what I call the gut check: do you have an uneasy feeling about cash, either that you’re running out of cash, or that you’re unsure how much cash you’re burning through and how fast you’re spending it?  Do you spend a lot of your time dealing with finance-related issues like fundraising, debt, investors, or cap table questions? Are you on the hot seat during board meetings on finance-related questions, metrics, runway, cash burn, or other issues? Trust your gut. If you have even a little uneasiness about how your CFO is operating, it’s probably worth heeding. You might not have a person capable of scaling, or you might have to invest more resources (time, mentor, fractional executive) to level up your CFO.

For members of the executive team, a telltale sign is whether or not your CFO engages with you and your team to understand your part of the business. Do they spend time learning and steeping in the substance of the business? Do they interact with all the functional leads like product, marketing, and People? Do they spend time in-market with customers, partners, or vendors? Sure, a CFO can understand the business by looking at the numbers, but you’ll never be able to scale if that’s the primary focus of your CFO because the numbers—all of them, and all of the time—are lagging. It’s impossible to be proactive if your CFO is totally focused on the numbers but doesn’t understand your functional issues, timelines, upcoming events or expenditures—and why. A CFO who is capable of scaling doesn’t see their role as “corporate,” as “administrative,” or as an enforcement function. They see it as strategic and as a partner to other parts of the business.

Other Signs Your CFO Isn’t Scaling

One sign of a CFO that can’t scale is whether or not they’re scrambling to hit deadlines. Everybody has to pull an all-weekend stint or over-nighter—occasionally, but if it happens regularly…it probably isn’t going to improve over time as things become more complex in the business. There’s always a pending crunch time that requires their personal attention and a ton of manual work – the monthly close, the audit, the budget, commission planning, compensation cycles.  These things are not surprises, and they come up the same time every month, quarter, or year. CFOs who are mired in doing all these things personally and manually haven’t built the systems, teams, or processes required to scale the business.

Another sign that your CFO can’t scale is if their solution to problems is to throw more people at it. If the accounting teams swells in size you might have a CFO who can’t think strategically about creating innovative processes and systems. “Throwing bodies at the problem” is easy because it’s the path of least resistance, but would your CFO allow other teams to do that? Accounting teams in particular tend to be the most traditional, paper-based teams and don’t need to be. Your CFO should be thinking strategically about how to scale financial systems with process and procedure rather than adding headcount.

A final obvious sign that your CFO isn’t scaling is if they get forecasts wrong, or don’t even try to do them.  Especially while your startup is in burn mode and constantly calculating its runway and months until the next required financing, regular and accurate/conservative forecasts are critical.  Even without a ton of revenue visibility on forward looking sales, good CFOs should have enough of a grip on expenses, cash flow, and order-to-cash dynamics to produce good, rolling 12-month cash forecasts. Anything short of that and you’ll be blindsided in the market, unable to take advantage of opportunities, or limping along with so-so growth for a long time.

In many startups people are learning on the fly but at some point you’ll begin to wonder whether everyone’s able to keep up or, more importantly, whether the people you have will be able to help your company scale. The CFO role touches every part of the organization and it’s critical to figure out earlier rather than later if your CFO can scale or whether you need to go in another direction.

(Posted on the Bolster blog here).

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