How to Engage with Your CFO
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.Â
(Also posted to the Bolster Blog).
Top 3 Mistakes Early Stage Founders Make
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.
- 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. - 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. - 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).
What Does Great Look Like in a Chief Revenue Officer?
(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)
Open Expense Policy
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.
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.
A Couple Tweaks to Running Great Board Meetings
I love innovation, and process is no different than product or business model in that regard. I’ve run and attended several hundred board meetings over the years, both those of companies where I’ve been CEO or Chairman, and those where I’m a director. I’ve written a lot about how I like running board meetings in Startup CEO, and as I mentioned the other day, I’m a co-author of a Second Edition of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, which is coming out in June and is available to pre-order now, along with Brad Feld and Mahendra Ramsinghani.
There are two adaptations I’ve made to my standard board routines in the last year or so, one driven by the pandemic and one not.
In olden times (that makes me sound like I’m 400 years old, but “pre-covid” sounds so clinical), I used to have a board dinner the night before or after every board meeting, and of course, everything was in person. That was a really important ritual in my mind towards the end of building the board as an effective team, where people on the team know each other as people, share things going on in their lives, share vulnerabilities, and develop bonds of trust. Without regular in-person meetings and dinners or social events, that gets a lot harder. Even when we get back to “normal,” I imagine the most we’ll do in-person board meetings is 1-2x/year.
What’s the zoom version of this?
We now do two 30-minute Executive Sessions (directors only) one before the board meeting officially starts and observers and team join, as well as the traditional one after the meeting ends. The purposes of the two sessions are different. The standard post-meeting Executive Session follows up on the meeting and has me talk about business or team issues that I don’t want to talk about with the full group present or get feedback from the board. But the one before the meeting is almost entirely social. I try to come up with a different question or topic to get all of us talking that is not about Bolster. Last week’s meeting was a simple “what’s the best thing that’s happened to you so far in 2022, and what’s the worse?” One time I asked everyone to show a picture from their phone photo roll and talk about it. You get the idea. It’s not the same as a dinner, but it seems like an effective substitute given the medium.
The second adaptation, and full credit to Fred for suggesting this one a while back, is the post-meeting survey. Now immediately after every Board meeting, I send a simple Google form to each director with the following questions:
- What are 1-3 areas/specifics where we are doing well?
- What are 1-3 areas/specifics you’re concerned about or where we could do better?
- Did the board book have the right level of detail and commentary? Is there anything you’d like to see change about the format or the content?
- Did the meeting meet your objectives for learning and discussion?Â
- If not, why not?
- Do you have any other feedback for Matt at this time?
I get great feedback, almost immediately and always from all board members, while things are still fresh in everyone’s mind. I’m planning to do this whether or not the meeting is remote…although it’s definitely good when the meeting is remote, and things like Executive Session, Closed Session, and debrief with me after Closed Session are quick or sometimes rushed.
There’s always room for innovation, even in standard and time-tested processes like board meetings.
What Men’s Rooms Can Teach Us About Leadership and Management
I hope this post doesn’t gross anyone out or offend anyone. I admit it’s a little weird, and that it’s more accessible to men. Hopefully everyone can get my point, even if men get it a bit more. I’m channeling Brad as I write this. So bear with me.
Here is a picture of a men’s room with floor mats under the urinals.

The difference between using a men’s room that has floor mats and using a men’s room that does not have floor mats is profound in multiple ways. I’ll leave out the specifics, but you can imagine the comparative experiences if you haven’t had one or both.
A really good floor mat, from a quick scan of Amazon and Uline just now, costs $11 if you buy in bulk and is built to last 4-6 weeks. That gives us an annual per urinal expense of about $100 – trivial in the scheme of maintaining an office, restaurant, or place of business.
But here’s the thing. These floor mats are few and far between. I don’t have scientific research on the matter, but I’d guess that between 1 in 5 and 1 in 10 places of business have them. Maybe even fewer.
So, urinal floor mats are (a) cheap, (b) easy to acquire, and (c) make a profound difference in the environment. And yet, they are only have 10-20% market penetration at most.
That market penetration is not far off from the prevalence of very good leadership and management in business. I hear stories all the time from executives about absolutely terrible leadership practices. I also hear plenty of stories that aren’t awful, but are evidence of non-leadership or non-management. The experience of working for a good manager, or in an organization with strong leadership, is profoundly different than working with the absence of those things.
To complete the analogy, good management and leadership are also (a) cheap, (b) easy to acquire, and (c) make a profound difference in the work environment. Sure, you can’t buy good leadership online, but it’s not all that difficult to be a caring, supportive, transparent manager. Heck, there’s even a book called The One Minute Manager.
So why the low market penetration of both? It makes no logical sense. It’s not as if most people haven’t had the experience of using a urinal with a floor mat…or of having a really good leader or manager. It’s not as if leaders and decision makers don’t appreciate those things themselves.
The answer boils down to three simple points that anyone who is a manager or leader can do, any day:
- You have to pay attention
- You have to care
- You have to act
Great leaders and managers exhibit all three of these traits. They pay attention to things around them, noting that Everything is Data. They care about people, about experiences, about impressions, about reputations. And when they notice that something is off – however small it is – they care enough to remember and then take the time to act. To make a small change. Send an email. Have a quick conversation. Make a suggestion. Give someone quick praise or constructive feedback.
And to come back to where this post started – it’s also not that hard to have a nice men’s room at your office or business or restaurant. You just have to pay attention to the fact that it’s a much better experience to buy floor mats. You have to care about the experience in the men’s room (for yourself, for employees, for customers, for vendors, for visitors). And then you have to act and either buy the stupid mats or ask an office manager to do the same!
The Impact of a Good Coach
I’m pretty close to the executive coaching world. My wife Mariquita is an extraordinary CEO coach. I’ve worked for decades with Marc Maltz from Hoola Hoop, who helped me transform everything about how I lead organizations. I’ve been friends with Jerry Colonna of Reboot fame for years (I did a fun podcast with Jerry last year called “Everyone is Scalable). I’m pretty good friends with Chad Dickerson. Bolster’s marketplace helps place CEO coaches and even has a programmatic approach to coaching and mentoring called Bolster Prime. The list goes on.
My friend Mitch, a fellow baseball coach, gave me a fun book a couple years ago that is a page-a-day called Coach: 365 Days of Inspiration for Coaches and Players, by Matthew Kelly. It’s a compilation of quotes. Some are better than others. But I just love this one from a couple weeks ago. While obviously it is in the sports context, the sentiments are the same around executive coaching.
Marc and I had one senior executive who we worked with years ago. They had significant personality and style issues that weren’t working well in our culture. They were abrupt, needlessly angry, and cultivated relationships based on fear, not based on trust. Marc and I were tearing our hair out trying to give this person feedback and coaching. Nothing was working. Then I delivered a 2×4 between his eyes. They argued with me and Marc and said that the problem was us…not them. That we were soft.
Two days went by. Then we met with them again. They came into the meeting visibly upset, shaking their head and a bit choked up. They opened the meeting by saying, “I went home and complained to my spouse about your feedback. And my spouse told me that, actually, you are right, and that I should ask my kids. My whole family feels the same way you do. More than my job is at risk — my marriage and family are at risk, too.”
Months and years later, with a ton of coaching and feedback and support from Marc and me and the rest of our executive team, this person had really turned it around. They were doing better at work. They were doing better at home. The work was long and painful and not without its bumps and backtracks. But the person made changes that were meaningful and permanent to all their relationships, not just something in the moment at work. It’s a clear case of this quote — coaching changed his life.
As I’ve said before, People are People. It doesn’t matter if you’re at home or at work. It doesn’t matter if you’re a B2C person or a B2B person. While there are some prominent examples of individuals throughout history who have very different work and home personae (John D. Rockefeller is one that comes to mind, but I’m sure there are other famous ruthless businesspeople who were empathetic and loving spouses and parents), most of us are simply humans, works in progress. We learn something in Context A, and it’s part of us when we are also in Context B.
The impact of a good coach goes way beyond how you lead your organization.
Unknown Unknowns
Unknown Unknowns
There are known knowns. These are things we know that we know. There are known unknowns. That is to say, there are things that we know we don’t know. But there are also unknown unknowns. There are things we don’t know we don’t know.”  –Donald Rumsfeld
Say what you will about Rumsfeld or the Iraq war, but this is actually a great and extensible quote. And more to the point, I’d say that one of the main informal jobs of a CEO, sort of like Connecting the Dots in that it’s not one of the three main roles of a CEO) is to understand and navigate known unknowns and unknown unknowns for your organization (hopefully you already understand and navigate the known knowns!). Here’s what I mean:
- An example of a known unknown is that a new competitor could pop up and disrupt your business from below (e.g., the low end) at any minute. Or let’s say your biggest partner buys one of your competitors. These are the kinds of things you and your team should be cognizant of as possibilities and always thinking about how to defeat
- While I suppose unknown unknowns are by definition hard to pin down, an example of an unknown unknown is something like a foreign leader deciding to nationalize the industry you’re in including your local subsidiary, or a young and healthy leader in your organization dying unexpectedly, or September 11. I suppose these are “black swan” events that Nassim Nicholas Taleb made famous in his book.
Helping your team identify potential known unknowns and think three steps ahead is critical. But helping your team turn unknown unknowns into known unknowns is, while much harder, probably one of the best things you can do as CEO of your organization. And there are probably two ways you can do this, noting that by definition, you’ll never be able to know all the unknowns. As you might expect, the way to do that comes down to increasing your pool of close-at-hand knowledge.
OnlyOnce – The Car
OnlyOnce – The Car
Not really contemplating a brand extension to my blog — the book is enough, but my friend Bill Wise just saw this car today in Larchmont, NY!
Playing To Win
Playing To Win
This weekend’s reading included Hardball, by George Stalk and Rob Lachenauer, which started as an article in Harvard Business Review sometime last year. The book is a fleshed out version of the article, so don’t expect meaningful new revelations if you’ve already read it, but it is an incredibly valuable read, with lots more and more detailed case studies.
As with most business books, it’s not really geared towards small, entrepreneurial companies, but that doesn’t matter. Most of the principles of competition — and how to win — are timeless. The basic principles, each of which gets a chapter, are on Unleashing Massive Force, Exploiting Anomalies (perfect for the data junkie within), Threatening the Competition’s Profit Zones, Plagiarizing with Pride, Breaking Compromises, and M&A.
Breaking Compromises is my favorite, because it deals with a facet of human nature that I think can be devastating to business: the “that’s the way it’s always worked” conundrum, otherwise known as “baggage.” Why does XYZ happen in our business, illogical as it may seem? Because that’s how we’ve always done it!
We have a (new) mechanism for dealing with the problem of baggage at Return Path, which is meant to be disarming, a bit funny, but dead serious at the same time. Any time anyone spots someone answering a question or a challenge with the “that’s the way it works” response, they’re strongly encouraged to pull themselves out of the situation and respond with a catchphrase like “baggage alert,” or “boy, that duffle bag must be heavy,” or “hey, nice napsack – is that new or have you had it for a while?” While it may be a little embarrassing to the recipient, it’s meant to challenge norms and bring about creative thought at all levels of the business.
Breaking Compromises has led to Southwest and Jet Blue, to Saturn (the car, not the planet), and to automobile leasing. Just think about what it — and the other tactics espoused in Hardball — can do for your company or industry.