Last week, I wrote about Inquiry vs. Advocacy, an important principle I learned early in life and then explored more deeply in an Action/Design workshop my coach Marc took our whole leadership team through years ago.

This week, I’ll continue to riff on the theme of communications tools in the CEO toolbelt by talking about The Ladder of Inference (detailed article here). This is a great graphic from the article:

Any time you’re struggling with opinions vs. opinions or people are jumping to conclusions based on a narrow set of evidence, this framework is your friend. The best way to start any tricky conversation with those characteristics is to start “at the bottom of the ladder,” meaning you start by reviewing the available data on the topic at hand. As John Adams said, “facts are stubborn things,” so start by agreeing on a common set of irrefutable data on the topic. Then you can take a step up the ladder to a more productive conversation about interpretations, then ultimately come to decisions or conclusions.

Jim Barksdale, the former CEO of Netscape had a great saying that supports this principle, too: “If we have data, let’s look at the data. If all we have are opinions, let’s go with mine.”

The language our team developed around this is easy. It’s like a safe word. Any time someone is jumping to conclusions without being rigorous about the underlying data, they’ll be the recipient of a comment like “wow you went right up to the top of the ladder on that one!” Either that, or someone will pull out a wonderful reference to Office Space.

My cofounder Cathy wrote a great post on the Bolster blog back in January called Procrastinating Executive Development, in which she talks about the fact that even executives who appreciate the value of professional development usually don’t get to it because they’re too busy or don’t realize how important it is. I see this every day with CEOs and founders. Cathy had a well phrased but somewhat gentle ask at the end of her post:

My ask for all CEOs is this: give each of your executives the gift of feedback now, and hold each other accountable for continued growth and development to match the growth and development of your company.

Let me put it in starker terms:

Grow or Die.

Every executive, every professional, can scale further than they think is possible, and further than you think is possible. Most of us do have some ceiling somewhere…but it will take us years to find it (if we ever find it). The key to scaling is a growth mentality. You have to not just value development, you have to crave it, view it as essential, and prioritize it.

Startups are incredibly dynamic. You’re creating something out of nothing. Disrupting an industry. Revolutionizing something. Putting a dent in the universe. For a startup to succeed, it has to constantly put something in market, learn, calibrate, accelerate, maybe pivot, and most of all grow. How can a leader of a startup scale from one stage of life to the next without focusing on personal growth and development if the job changes from one quarter to the next?

I was lucky enough to have a great leadership team at my prior company, Return Path, over the course of 20 years. Within that long block of time with many executives, there was a particular period of time, roughly 2004-2012, that I jokingly refer to as the “golden age.” That’s when we grew the business from roughly $5mm in revenue to $50 or $60mm. The remarkable thing was that we executed that growth with the same group of 5-6 senior executives. A couple new people joined the team, and we struggled to get one executive role right, but by and large one core group took us from small to mid-sized. Why? We looked at each other — literally, in one meeting where we were talking about professional development — and said, “we have to commit to individual coaching, to team coaching, and to growth as leaders, or the company will outpace us and we’ll be roadkill.”

That set us on a path to focus on our own growth and development as leaders. We were constantly reading and sharing relevant articles, blog posts, and books. We engaged in a lot of coaching and development instruments like MBTI, TKI, and DISC. We learned the value of retrospectives, transparent 360s, and a steady diet of feedback. We challenged ourselves to do better. We worked at it. As one of the members of the Golden Age said of our work, “we went to the gym.”

The “Grow or Die” mantra is real. You can’t possibly be successful in today’s world if you’re not learning, if you don’t have a growth mentality. You are never the smartest person in the room. The minute you are convinced that you are…you’re screwed.

If you don’t believe me, look at the development of your business itself as a metaphor for your own development as a leader. What happens to your startup if it stops growing?

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

If I had to pick one human trait that is the single most impactful in one’s ability to have positive and successful interpersonal relationships, there’s a hands-down winner: Self-Awareness. This is true no matter what kind of relationships you’re talking about — parent, manager, executive, friend, partner or spouse.

Someone shared a framework with me years ago that helps explain why this is true, which I’ve been meaning to blog about for a long time. I found this image, which is close enough to the 2×2 that was once drawn for me on a whiteboard.

The framework is at once incredibly simple and incredibly complex.

Having true self-awareness and the ability to be reflective, to take in input and feedback, and the ability to accurately self-assess is where it all starts. “I am unhappy today,” “I am doing a bad job right now,” “I am not good at doing this task” are all pretty difficult things to say to yourself. And yet, without those, it’s impossible to progress through this framework.

I learned this framework where boxes II and III in what you see in this graphic are the other way around, but I’m not sure that matters as much as box I being first and box IV being last.

Once you have a solid level of self-awareness, you can exert some level of self-control. That’s not a guarantee — self-control is its own animal, but you can’t manage what you can’t understand. Empathy is similarly a follow-on to self-awareness, but also its own trait. How can you possibly understand what someone else is going through if you don’t understand what you’re going through?

The final box — Influence — is the result of building on all three of the prior traits. It’s impossible to influence others, to have deep and lasting relationships, and to be able to work productively together, without having a solid level of empathy and self-control.

You can be a leader without any of these traits if you’re an autocrat, whether a political one or a corporate one. If people MUST listen to you, then you can tell them what to do. But founders, especially ones who control their companies, shouldn’t be under the misapprehension that they are influencing others if what they’re really doing is ordering them around.

Can self-awareness be taught, or is it something you’re either born with or not? While most traits have a balance of nature and nurture, I am a big believer that self-awareness can largely be learned over time, so let’s call it a 10/90 on the nature/nurture scale. I’ve had a lot of influencers in my life who have, in their own ways helped me learn the practice of self-awareness, from my parents, to the professor in college who gave me my first 2×4, to my first couple of managers in my early jobs, Neal and Eleanor, to my coach, Marc who gave me my first 360, to my long-time colleagues along the way at Return Path and Bolster, to my wife, Mariquita, even to my kids. I’m sure I’m forgetting many others along the way. I’m thankful to all of them.

Want to improve your practice of management? Leadership? Collaboration and teamwork?

It all starts with self-awareness.

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?

(This blog post was first published as an article in Entrepreneur Magazine on April 15.)

Creating strong boards can help propel a board forward. Weak and ineffective boards hold a company back.

As a CEO, one of the most important (yet overlooked) tools in the playbook is building and leading a board of directors. Throughout my 20+ years of entrepreneurship, I’ve led four companies (including Bolster, where I’m a co-founder and CEO today) and served on eight boards. I’ve learned that strong boards can help propel a company forward and I’ve also witnessed how weak and ineffective boards can hold companies back. Mediocre or mismanaged advice, plus lack of accountability, can do long-term damage to a business as well.

Drawing from personal experience and anecdotes from dozens of Bolster’s client CEOs, here are some tried and true “Seven Habits of Highly Effective Boards.”

Habit 1: Begin with the board in mind

A lot of CEOs treat board curation as an afterthought, which means that boards tend to consist largely of who happened to be in their network at the company’s inception: investors. CEOs also tend to treat their boards as a distraction or an annoyance. Both of these lines of thought are problematic. 

Boards should be viewed as a CEO’s second team (along with their management team), as a strategic weapon that helps the company succeed and as an opportunity to bring new voices and perspectives. Research has shown the more independent and diverse a board is, the better it performs.

Habit 2: Be proactive about board recruiting

Devote as much focus to building a board as to building the executive team. This process is time-consuming and can’t be delegated to anyone else. Aspire to reach people who may feel out of reach. Asking someone to join the board is a big honor, so that ask becomes a good calling card. When recruiting, interview as many contenders as possible, don’t be afraid to reject those who aren’t a good fit and have finalists audition by attending a board meeting. Source broadly, too. Diversity is really important for many reasons; challenge any recruiter, agency or platform to surface diverse board candidates.

Habit 3: Keep your board balanced using the Rule of 1s

Whether it’s a three-person startup board or a seven-person scale-up board, it should include representation from all three director types: investors, management directors and independents. A few basic principles on board composition that work well are what I call the Rule of 1s: First, boards should include one, and only one member of the management team: the CEO. Even if co-founders or C-level managers are shareholders, don’t burn a board seat for a perspective that you have access to regularly. Second, for every new investor to the board, add one independent director, which is the biggest opportunity to introduce external perspectives. If your board gets too crowded with subsequent funding rounds, ask one or more investors to take observer seats to make space for independents. And don’t be afraid to change your board composition over time. Companies are dynamic and boards should be, too.

Habit 4: Cultivate mutual accountability and respect

While a board might seem intimidating, work past the power dynamic and push toward collaboration and mutual accountability. To ensure board members are prepared for meetings, keep commitments and leverage their networks, set the example by demonstrating preparation, consistency and reliability. By regularly delivering pre-read materials to the board several days in advance, the board will build a new habit. By soliciting feedback from board members after each meeting (and even offering them feedback), you’ll show the board that you’re listening. Over time, they’ll lean in, too.

Habit 5: Drive intellectually honest discussions

Even on the healthiest leadership teams, it can be scary to disagree with or challenge a sitting CEO (after all, they are still the one in charge!). But this power dynamic flips in a boardroom, which gives that group a unique opportunity to push and challenge business assumptions. While it may be tempting to look for board members with softer dispositions, it can be more beneficial to have tough, direct board members who aren’t afraid to express their opinions, but who are also good listeners and learners. My favorite discussions are conversations where I’m pushed to consider a different direction. It helps get more done, surfaces better ideas and increases the effectiveness of the company.

Habit 6: Lean in on strategic, lean out on tactics

Even board members who are talented operators have a hard time parachuting into any given situation and being super useful. Getting operational help requires a lot of regular engagement on a specific issue or area. But they must be strategically engaged and understand the fundamental dynamics and drivers of your business: economics, competition and ecosystem. This is an easy habit to reinforce in meetings. If board directors drift toward getting too tactically in the weeds, that’s great feedback to offer after the meeting.

Habit 7: Think outside the box

Good board members understand all the pieces on the chess table; great board members go one step further and pattern match to provide advice, history, context and anticipated consequences. This is an enormous benefit to CEOs focused on the minutiae of the day-to-day, particularly if a business operates in a trailblazing industry where many of the rules may not yet be written. As a CEO, if you’ve never seen something first hand before, it’s hard to get clarity and external perspectives, which is why it’s crucial that great board members bring pattern recognition and “out-of-the-box thinking” to their role.

At the end of the day, boards are there to support and direct a company. There’s no perfect formula, but by implementing these steps with a few healthy habits, CEOs can cultivate strong, dynamic boards for their companies.

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 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.

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.

Book Short:  Required Reading, Part II

Every once in a while, a business book nails it from all levels.  Well written, practical, broadly applicable to any size or type of organization, full of good examples, full of practical tables and checklists.   The Leadership Pipeline, which I wrote about here over six years ago, is one of those books — it lays out in great and clear detail a framework for understanding the transition from one level to another in an organization and how work behaviors must change in order for a person to succeed during and on the other side of that transition.  In an organization like Return Path‘s which is rapidly expanding and promoting people regularly, this is critical.  We liked the book so much that we have adopted a lot of its language and have built training courses around it.

The book’s sequel, The Performance Pipeline (book, Kindle), also by Stephen Drotter but without the co-authors of the original book, is now out — and it’s just as fantastic.  The book looks at the same six level types in an organization (Enterprise Manager, Group Manager, Business Manager, Functional Manager, Manager of Managers, Manager of Others, and Self Managers/Individual Contributors) and focuses on what competencies people at each level must have in order to do their jobs at maximum effectiveness — and more important, in order to enable the levels below them to operate in an optimal way.

This book is as close to a handbook as I’ve ever seen for “how to be a CEO” or “how to be a manager.”  Coupled with its prequel, it covers the transition into the role as well as the role itself, so “how to become a CEO and be a great one.”  As with the prequel, the author also takes good care to note how to apply the book to a smaller organization (from the below list, usually the top three levels are combined in the CEO, and often the next two are combined as well).  No synopsis can do justice to this book, but here’s a bit of a sense of what the book is about:

• Enterprise Manager:  role is to Perpetuate the Enterprise and develop an Enterprise-wide strategic framework – what should we look like in 15-20 years, and how will we get the resources we need to get there?
• Group Manager:  role is to manage a portfolio of businesses and develop people to run them
• Business Manager:  role is to optimize short- and long-term profit and develop business-specific strategies around creating customer and stakeholder value
• Functional Manager:  role is to drive competitive advantage and functional excellence
• Manager of Managers:  role is to drive productivity across a multi-year horizon, and focus
• Manager of Others:  role is to enable delivery through motivation, context setting, and talent acquisition
• Self Managers/Individual Contributors:  role is to deliver and to be a good corporate citizen

I could write more, but there’s too much good stuff in this book to make excerpts particularly useful.  The Performance Pipeline is another one of those rare – “run, don’t walk, to buy” books.  Enjoy.  For many of my colleagues at RP – look out – this one is coming!

(This is the second post in the series… the first one When to Hire your first Chief Privacy Officer is here)

Most Chief Privacy Officers are fairly specialized, often coming from a legal or law enforcement background, but regardless of background I’ve found that ideal startup Chief Privacy Officers do three things particularly well.

First, a great Chief Privacy Officer will work to create educated evangelists inside the company.  Our Privacy team at Return Path, under Dennis Dayman’s leadership, had a lot of experience and industry certifications, but that experience was not something only for regulators and other companies, or only bragging rights within their team. They also took the time to make sure others in the company, especially in the product management and engineering teams, received some of that same training and those same certifications.  By not making the Privacy team a single point of knowledge or failure, Dennis was able to make Privacy part of our product strategy and offense as opposed to a mitigation or defensive function

A second ideal characteristic of a Privacy Officer is that they also handle the basics of InfoSec, in addition to privacy.  If you’re actually a security-related company or a massive consumer or financial organization, you may need a dedicated Chief Information Security Officer.  If you aren’t, then a good Chief Privacy Officer should be able to handle a number of the functions that a CISO would otherwise handle, especially on the policy and communication front.

And third, a great Chief Privacy Officer is an excellent communicator, both internally and externally, and they help connect you to the relevant members of your community or ecosystem.  When we had a sizable data breach on Thanksgiving Day about 10 years ago, our fractional head of privacy, Tom Bartel, was on the spot. He wrote emails and external blog posts that needed almost no review.  He was also instantly communicating with dozens of his counterparts at related companies so that the industry knew where we stood and what we were doing about the problem.  It was like an instant activation of an emergency response system!

Don’t wait until you have a data breach to hire a great Chief Privacy Officer because by the time you need one it will be too late.

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

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

Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent.

One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events.  Particularly if you’re a B2B company that engages with clients during the sales process, you’ll probably find yourself at a lot of client meetings and events, either internal or external.  Your CRO will be there, too, which gives you a great opportunity to spend large blocks of time together in transit, or a good deal of time together socially. One thing we learned during the work-at-home pandemic is just how much time we save by not traveling.  So when life resumes to normal, why waste time in an Uber or on a plane when you can have a deep strategic conversation or even a personal/social one with one of your senior executives? Of course, you have to actually be more proactive in meeting with your CRO since you won’t have events that naturally bring you together, but I’ve found that the early morning time in the hotel gym or late-night drink in the lobby bar before heading up to bed now translates to time I can have with my CRO. 

Another way to engage with the CRO is In a Weekly Forecast meeting.  Jeff Epstein, former CFO of Oracle, was one of my long-time board members at Return Path and he helped us architect a new core business process once our sales team got large and mature and geographically disparate enough that it was hard for us to have a solid forecast.  Both me and our CFO engaged in the Weekly Forecast meeting and because of that we forced the discipline of a good roll-up of all regions and business units. The CRO and all sales managers attended and knew that we were paying attention to the numbers and trends and asking tough questions. Our attendance was a forcing function for the CRO so that they organized a pre-meeting the prior day with all teams and units to prepare, and that in and of itself had a cascading effect through the organization of adding discipline, rigor, and accuracy to the forecast.  It also made me a lot more empathetic to my CRO’s issues with respect to the sales leadership team.

Finally, the other way that I engaged with the CRO was ad hoc, either internally or in-market.  My most successful heads of sales have been good at winding me up and pointing me at things as needed, whether that means getting on a plane or Zoom to help close a deal or save a client, or doing a 1:1 mentoring session with a key employee. So, not all interactions with the CRO have to be initiated by the CEO, and a great CRO will use the CEO, leverage their time, when it’s needed.

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