I received in the mail yesterday (by overnight priority mail, no less), a 400+ page prospectus from Mittal, a Dutch company in which I apparently own a few shares of stock through a managed mutual fund I’m part of. This book was BIG – well over 2 inches thick and big enough to have a binding strip instead of staples. And it had enough legalese in it to put anyone to sleep.

What did I do with it? After ranting about how silly it was to ever print such a thing for mass push distribution to an audience that largely doesn’t care about it — straight into the trash. With a big thud, of course.

What a ridiculous waste. Why print it on paper at all? Make it available online via pdf. Email shareholders or send them a postcard or leave an automated voicemail and ask them if they want a hard copy. Figure out which shareholders are in a managed fund, and send a single copy to the fund manager, since the individuals don’t even know they’re shareholders or don’t make decisions about individual stocks in the fund. Do something that costs less and doesn’t destroy trees that 99% of people will never read.

Shame on Mittal and their bankers, proudly displayed on the cover of the book — Goldman Sachs, Citigroup Credit Suisse, HSBC and Societe General.

Complex Collaborations

I just read a new book entitled Business Without Boundaries:  An Action Framework for Collaborating Across Time, Distance, Organization, and Culture.  I happen to know one of the authors, Don Mankin, who was on our trip to Antarctica last year.  The book is a good, quick read for anyone running an organization that requires any degree of complex collaboration, whether in the form of multiple offices with a single company, close relationships with suppliers or customers or channel partners, or even a joint venture.

Mankin and his co-author Susan Cohen present three case studies:  John Deere, Radica, and Solectron.  They then tie their learnings together into a solid framework that’s almost a how-to checklist for organization leaders to follow.  While the writers take an academic approach, the learnings and framework steps presented are anything but academic — they place a huge premium, for example, on relationship building and communication patterns.  These are all things we’ve worked through over the years at Return Path, whether managing employees across multiple offices  or in working with some of our reseller partners or clients.

All in, it’s a good read — and not just because I hung out with this guy in an igloo for two weeks!

Fig Wasp #879

I have 7 categories of books in my somewhat regular reading rotation:  Business (the only one I usually blog about), American History with a focus on the founding period, Humor, Fiction with a focus on trash, Classics I’ve Missed, Architecture and Urban Planning (my major), and Evolutionary Biology.  I’m sure that statement says a lot about me, though I am happy to not figure it out until later in life.  Anyway, I just finished another fascinating Richard Dawkins book about evolution, and while I usually don’t blog about non-business books, this one had an incredibly rich metaphor with several business lessons stemming from it, plus, evolution is running rampant in our household this week, so I figured, what the heck?

The Dawkins books I’ve read are The Selfish Gene (the shortest, most succinct, and best one to start with), The Blind Watchmaker (more detail than the first), Climbing Mount Improbable (more detail than the second, including a fascinating explanation of how the eye evolved “in an evolutionary instant”), The Ancestor’s Tale (very different style – and a great journey back in time to see each fork in the evolutionary road on the journey from bacteria to humanity), and The God Delusion (a very different book expounding on Dawkins’ theory of atheism).  All are great and fairly easy to read, given the topic.  I’d start with either The Selfish Gene or maybe The Ancestor’s Tale if you’re interested in taking him for a spin.

So on to the tale of Fig Wasp #879, from this week’s read, Climbing Mount Improbable.  Here’s the thing.  There are over 900 kinds of fig trees in the world.  Who knew?  I was dimly aware there was such a thing as a fig tree, although quite frankly I’m most familiar with the fig in its Newton format.  Some species reproduce wildly inefficiently — like wild grasses, whose pollen get spread through the air, and with a lot of luck, 1 in 1 billion (with a “b”) land in the right place at the right time to propagate.  At the opposite end of the spectrum stands the fig tree.  Not only do fig trees reproduce by relying on the collaboration of fig wasps to transport their pollen from one to the next, but it turns out that not only are there over 900 different kinds of fig trees on earth, there are over 900 different kinds of fig wasps — one per tree species.  The two have evolved together over thousands of millenia, and while we humans might take the callous and uninformed view that a fig tree is a fig tree, clearly the fig wasps have figured out how to swiftly and instinctively differentiate one speices from another.

So what the heck does this have to do with business?  Three quick lessons come mind.  I’m sure there are scores more.

1. Collboration only works when each party benefits selfishly from it.  Fig wasps don’t cross-pollenate fig trees bcause the fig trees ask nicely or will fire them if they don’t.  They do their job because their job is independently fulfilling.  If they don’t — they probably die of starvation.  They’re just programmed with a very specific type of fig pollen as their primary input and output.  We should all think about collaboration this way at work.  I wrote a series of posts a couple years back on the topic of Collboration Being Hard, and while all the points I make in those posts are valid, I think this one trumps all.  Quite frankly, it calls on the core principle from the Harvard Project on Negotiation, which is that collaboration requires a rethinking of the pie, so that you can expand the pie.  That’s what the fig trees and fig wasps have done, unwittingly.  Each one gets what it needs far more so than if it had ever consulted directly with the other.  The lesson:  Be selfish, but do it in a way that benefits your company.

2. Incredibly similar companies can have incredibly distinct cultures.  900+ types of fig tree, each one attracting one and only one type of fig wasp.  Could there be anything less obvious to the untrained human eye?  I assume that not only would most of us not be able to discern one tree or wasp type from another, but that we wouldn’t be able to disdcern discern any of the 900+ types of trees or wasps from thousands or hundreds of thousands or millions (in the case or urbanites) types of trees or bugs in general!  But here’s the thing.  I know hundreds of internet companies.  Heck, I know dozens of email companies.  And I can tell you within 5 minutes of walking around the place or meeting an executive which ones I’d be able to work for, and which ones I wouldn’t.  And the older/bigger the company, the more distinct and deeply rooted its culture becomes.  The lessons:  don’t go to work for a company where you’d even remotely uncomfortable in the interview environment; cultivate your company’s culture with same level of care and attention to detail that you would your family — regardless of your role or level in the company!

3. Leadership is irrelevant when the operating system is tight.  You think fig wasps have a CEO?  Or a division president who reports into the CEO that oversees both fig wasps and fig trees, making sure they all cross-pollenate before the end of the quarter?  Bah.  While as a CEO, you may be the most important person in the organization sometimes, or in some ways, I can easily construct the argument that you’re the least important person in the shop as well.  If you do your job and create an organization where everyone knows the mission, the agenda, the goal, the values, the BHAG, whatever you want to call it — withoutit needing to be spelled out every day — you’ve done your job, because you’ve made a company where people rock ‘n’ roll all night and every day without you needing to be in the middle of what they’re doing. 

I’m sure there are other business lessons from evolutionary biology…send them along if you have good thoughts to share!

Running a Productive Offsite

A couple OnlyOnce readers asked me to do a post on how I run senior team offsites.  It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.

My senior team has four offsites per year.  I love them.  They are, along with my Board meetings, my favorite times of the year at work.  Here’s my formula for these meetings:

–          WHY:  There are a few purposes to our offsites.  One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level.  So for us, these are the only times of the year that we are actually in the same place.  But even if we were all in one place, we’d still do them.  The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time.  The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics.  It’s critically important to build and sustain deep relationships across the Executive Team.  We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company.  As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical

–          WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total).  Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people).  That part is new as we’ve gotten bigger.  In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics

–          WHERE:  Offsites aren’t always offsite for us.  We vary location to make geography work for people.  And we try to contain costs across all of them.  So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel.  Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place.  Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night

–          WHEN:  4x/year at roughly equal intervals.  We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded.  Now we basically do them between Board meetings.  The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year.  Our general formula when it’s the smaller group is two days and at least one, maybe two dinners.  When it’s the larger group, it’s three days and at least two dinners.  For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.

–          WHAT:  Our offsites are super rigorous.  We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations.  The agenda for these offsites varies widely, but the format is usually pretty consistent.  I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union.  Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc.  We always try to spend half a day on team and individual development.  Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing.  Then we have a team development plan check-in that’s the same, but about how the team is interacting.  We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time.  Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!).  There’s also time at breaks for sub-group meetings and ad hoc conversations.  We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it.  Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m.  We usually have a closing check-out, next steps recap type of exercise as well.

–          HOW:  Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.

I’m sure I missed some key things here.  Team, feel free to comment and add.  Others with other experiences, please do the same!

Lean In, Part II

My post about Sheryl Sandberg’s Lean In a couple months ago created some great dialog internally at Return Path.  It also yielded a personal email from Sheryl the day after it went up encouraging me to continue “talking about it,” as the book says, especially as a male leader.  Along those lines, since I wrote that initial post, we’ve had a few things happen here that are relevant to comment on, so here goes.

We partnered  with the National Center for Women & IT to provide training to our entire organization on unconscious bias.  We had almost 90% of the organization attend an interactive 90 minute training session to explore how these biases work and how to discuss these issues with others.   The goals were to identify what unconscious bias is and how it affects the workplace, identify ways to address these barriers and foster innovation, and provide practice tools for reducing unconscious biases.   While the topic of unconscious bias in the workplace isn’t only about gender, that’s one major vector of discussion.  We had great feedback from across the organization that people value this type of dialog and training.  It’s now going to be incorporated into our onboarding program for new employees.

Second, as I committed to in my original post, we ran a thorough gender-based comp study.  As I suspected, we don’t have a real issue with men being paid more than women for doing the same job, or with men and women being promoted at different rates.    That’s the good news.  However, the study and the conversations that we had around it yielded two other interesting conclusions.  One is that that we have fewer women in senior positions than men, though not too far off our overall male:female ratio of 60:40.  On our Board, we have no women.  On our Executive Committee, we have 1 of 10 (more on this below).  On our Operating Committee, we have 8 of 25.  Of all Managers at the company, we have 32 of 88.  So women skew to more junior roles.

The other is that while we do a good job on compensation equity for the same position, it takes a lot of deliberate back and forth to get to that place.  In other words, if all we did was rely on people’s starting salaries, their performance review data, and our standard raise percentages, we would have some level of gender-based inequality.  Digging deeper into this, it’s all about the starting point.  Since we have far more junior/entry level women than men, the compensation curve for women ends up needing to be steeper than that of men in order to level things out.  So we get to the right place, but it takes work and unconventional thinking.

Finally, I had an enlightening process of recruiting two new senior executives to join the business in the past couple of months.   I knew I wanted to try and diversify my executive team, which was 25% female, so I made a deliberate effort to focus on hiring senior women into both positions.  I intended to hire the best candidate, and knew I’d only see male candidates unless I intentionally sourced female candidates.  For both positions, sourcing with an emphasis on women was VERY DIFFICULT, as the candidate pools are very lopsided in favor of men for all the reasons Sheryl noted in her book.  But in both cases, great female candidates made it through as finalists, and the first candidate to whom I offered each job was female – both superbly qualified.  In both cases, for different reasons I can’t go into here, the candidates didn’t end up making it across the finish line.  And then in both cases, when we opened up the search for a second round, the rest of the candidate pool was male, and I ended up hiring men into both roles.  Now my resulting exec team is even more heavily male, which was the opposite of my intention.  It’s very frustrating, and it leaves us with more work to do on the women-in-leadership topic, for sure.

So…some positives and some challenges the last few months on this topic at Return Path.  I’ll post more as relevant things develop or occur.  We are going to be doing some real thinking, and probably some program development, around this important topic.

The Phoenix Project:  a novel about IT, DevOps, and Helping Your Business Win, by Gene Kim, Kevin Behr, and George Spafford  is a logical intellectual successor and regularly quotes Eli Goldratt’s seminal work The Goal and its good but less known sequel It’s Not Luck.

The more business books I read, the more I appreciate the novel or fable format. Most business books are a bit boring and way too long to make a single point. The Phoenix Project is a novel, though unlike Goldratt’s books (and even Lencioni’s), it takes it easy on the cheesy and personal side stories. It just uses storytelling techniques to make its points and give color and examples for more memorable learning.

If your organization still does software development through a waterfall process or has separate and distinct development, QA, and IT/Operations teams, I’d say you should run, not walk, to get this book. But even if you are agile, lean, and practice continuous deployment, it’s still a good read as it provides reminders of what the world used to be like and what the manufacturing-rooted theories are behind these “new” techniques in software development.

I am so glad our technology team at Return Path, led by my colleagues Andy Sautins and David Sieh, had the wisdom to be early adopters of agile and lean processes, continuous deployment many years ago, and now dockers. Our DevOps process is pretty well grooved, and while I’m sure there are always things to be done to improve it…it’s almost never a source of panic or friction internally the way more traditional shops function (like the one in the book). I can’t imagine operating a business any other way.

Thanks to my long time friend and Board member Greg Sands of Costanoa Venture Capital for suggesting this excellent read.

I realize I haven’t posted much lately.  As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004.  That inspired me to create a blog for entrepreneurs and leaders.  I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO:  A Field Guide to Scaling Up Your Business back in 2013.

Today is a special day in my entrepreneurial journey and in the life of the company that I started back in 1999 (last century!), Return Path, as we announce that Return Path has entered into a definitive agreement to be acquired by an exciting new company called Validity.  Press release is here.

Over almost 20 years, we’ve built Return Path into one of the largest and (I think) most respected companies in the email industry.  We’ve had a culture of innovation that has led to some groundbreaking products for our customers and partners to help make email marketing work better for consumers as well as marketers, and to help keep inboxes safe and clean for mailbox providers and security companies.  

But the company is unusual in many respects.  One of those is longevity. I’m not sure how many Internet companies started in 1999 are still private, backed and led by the same team the whole time, and generally in the same business they started in.  Another is our values-driven “People First” culture. From Day 1, we have believed that if we attract and retain and develop and invest in the best people, we will make our customers successful with great products and service, and that if we do right by our customers, we will do right long term by our shareholders.  While I know that not every employee who ever walked through our doors had a great experience, I know most did and hope that all of them realize we tried our best. Finally, I’m proud that our company gave birth to a non-profit affiliate Path Forward a few years back at the hands of executives Andy Sautins, Cathy Hawley, and Tami Forman.  Path Forward helps parents get back to work after a career break and helps companies improve their gender diversity and hiring biases and has already been a game changer for dozens of companies and hundreds of women.

Today, Return Path serves almost 4,000 customers in almost every country on the globe, with $100 million in revenue, profitable, and excited about the next leg of our brands’ and our products’ lives in the care of Validity.  If you haven’t heard of Validity before today, watch out – you will hear a LOT about them in the weeks and months ahead. They are an incredibly exciting new company with a vision to help tens of thousands of companies across the globe improve their data quality but also help them use data to improve business results.  That vision, inspired by a new friend, CEO Mark Briggs, is a wonderful fit for Return Path’s products and services and people.

To finish this post where I started, Fred’s exact words in that post which got this blog going were:

What does this mean for entrepreneurs and managers? It means that the first time you run a business, you should admit what you are up against. Don’t let ego get in the way. Ask for help from your board and get coaching and mentoring. And recognize that you may fail at some level. And don’t let the fear of failure get in the way. Because failure isn’t fatal. It may well be a required rite of passage.

All of that is true and has been great advice for me over the years.  But Fred left out one important piece, which is that entrepreneurs need to constantly thank the people around them who either work their butts off as colleagues in the business or who give them helpful advice and coaching.  Return Path’s journey has been a long one, longer than most, and the full list of people to thank is too long for a blog post.

I’ve noted Fred and Brad in this post already and I want to thank them and also thank Greg Sands from Costanoa Ventures, the third member of our “dream team” investor syndicate, for their friendship and unwavering support and good counsel for me and Return Path for almost two decades, as well as many other board members we’ve had over the years including long-time independent directors Jeff Epstein, Scott Petry, and Scott Weiss.

I want to thank my co-founders Jack Sinclair and George Bilbrey, and anyone who has ever been on my executive team, including long-time execs Ken Takahashi, Shawn Nussbaum, Cathy Hawley, Dave Wilby, Anita Absey, Angela Baldonero, Andy Sautins, Louis Bucciarelli, Mark Frein, and David Sieh.  There’s nothing quite like being in the proverbial foxhole with someone during a battle or two or ten to forge a tight bond. I want to thank Andrea Ponchione, my extraordinary assistant for 14 years, who keeps me running, sane, and smiling every day. I want to thank my executive coach Marc Maltz and the members of my CEO Forum for allowing me to be unplugged and for their friendship and advice.  I want to thank all of Return Path’s 430 employees today and over 1,300 ever for their hard work in building our company and culture together and for our 4,000 customers and partners for putting their faith in us to help them solve some of their biggest challenges with email.

Finally, no thank you list for this journey would be complete without saying a special thank you to my wonderful wife Mariquita and kids Casey, Wilson, and Elyse.  They deserve some kind of special honor for being inspirational cabin-mates on the entrepreneurial roller coaster without ever being asked if they were up for it.

This event may inspire me to begin writing more regularly again on OnlyOnce.  Stay tuned!

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).

This is the second post in the series…. the first one When to hire your first Chief People Officer is here).

While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything illegal, discriminatory, or harassing, you’ll end up in legal trouble and you’ll lose—big time. So, it’s not enough, if you’re expanding rapidly, to “just get a Chief People Officer,” you need to hire a great Chief People Officer and I have found that great Chief People Officers do three things particularly well:

The most important characteristic or attribute of a great Chief People Officer is that they believe their function is strategic. In Startup CXO Chief People Officer Cathy Hawtrey wrote about the ways in which HR/People can be a strategic function and not just a tactical corporate function.  It’s true of most functions, but for whatever reason, (likely past experience), HR leaders frequently don’t view themselves or their functions as strategic, which is not only a huge missed opportunity but maybe says something more important about the confidence level of the Chief People Officer.  If that’s their frame of reference, then they will likely be tactical managers, they’ll keep the trains running on time, but you won’t be able to anticipate the changing talent landscape, much less be strategic about it.  If they believe they can move the needle on the business by improving engagement and productivity and efficiency, if they believe they can make the executive team more effective by helping you with team facilitation and coaching…they can do anything.

A second important characteristic of the Chief People Officer is courage—they have the courage to call you (you, the CEO) out on things directly and firmly when they see you doing or saying anything that is a bit off. It could be around language, inclusion, values, authenticity, or anything else, but they don’t let it slide or ignore it. The CPO, along with you, are the principal stewards of the company’s values and culture.  Even the best CEOs benefit from having a watchdog from time to time.

A third critical trait of a great Chief People Officer is that they think about investment in People in terms of ROI.  It’s one thing to run a killer recruiting function and fill seats efficiently, with high quality, as asked.  It’s an entirely different thing to start the recruiting process by asking if the role is needed, at that level and compensation band, or whether there are other people, fractional people, contractors, or shifts in lower value activities that could be put to work instead.  Only heads of People with deep understandings of the business can transform the function from a gatekeeper/”no” role into a business accelerator.

A great Chief People Officer is all of these things—strategic, courageous, and financially astute. Above all, great Chief people Officers know that they are the role model within a company and that their behavior, their language, their inclusiveness is setting the tone and providing a template for others to follow. 

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

This is the third post in the series. The first one When to hire your first CPO is here and What does Great Look Like in a CPO is here).

Chief Privacy Officers who aren’t scaling well past the startup stage are the ones who typically have the following characteristics and you should look for some of these telltale signs.

First, if your Chief Privacy Officer looks at you sideways when you ask for a strategy or even a mitigation plan for a breach, then you might have a bigger problem than the fact that you don’t have a plan.  While we like to talk about things like Privacy by Design and using data protection as an offensive strategic weapon, the reality is that Chief Privacy Officers need to have actionable plans in place at all times for the areas where they judge your company to be the most vulnerable.  If you ask to see the plan or get briefed on it and you get back a blank stare, you know you have a reactive person on your hands for what needs to be a thoughtful proactive role.

Second, you might have a Chief Privacy Officer who is not scaling if they would rather lecture you on GDPR than talk about why your data protection plan will win business.  Privacy people can be geeky, legally-oriented, policy-focused and very technical.  All that is well and good but there is so much more that a great Privacy Officer can do. For example, if your Chief Privacy Officer can’t engage in strategy with you and other executives and understand the levers of your business and how their role can help further them, you may as well use an outside law firm instead of taking up a valuable seat at the table internally.

The Privacy team can be small and somewhat insulated from the business, but your Chief Privacy Officer needs to be able to engage the entire company, they need to be thinking strategically about the business, and they need to have short- and long-term plans in place for contingencies and forseeable roadblocks. If they can’t bring these skills to the table at startup scale, how can they bring them to the table when things really take off?

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

Across 22 years and two companies now, our system of giving performance feedback has evolved significantly. I thought I’d take a pass at chronicling it here and seeing if I had any learnings from looking at the evolution. Here’s how things evolved over the years:

• Written performance reviews. The first year of Return Path, we had a pretty standard process for reviews. They were more or less “one-way” (meaning managers wrote reviews for their direct reports), and they only happened annually.
• Written 360 reviews. We pretty quickly moved from one-way reviews to 360s. I wrote about this here, but we always felt that being able to give/receive feedback in all directions was critical to getting a full picture of your strengths and weaknesses.
• Live 360 reviews. In addition to the above post/link, I wrote about this a bit further here and here. The short of it is that we evolved written 360s for senior leaders into facilitated live conversations among all the reviewers in order to resolve conflicting feedback and prioritize action items.
• Live 360 reviews with the subject in the room. I wrote about this here…the addition of the subject of the review into an observer/clarifying role present for the facilitated live conversation.
• Peer feedback. At some point, we started doing team-based reviews on a regular cadence (usually quarterly) where everyone on a team reviews everyone on a team round-robin style in a live meeting.

The evolution follows an interesting pattern of increasing utility combined with increasing transparency. The more data that is available to more people, the more actionable the feedback has gotten.

The pluses of this model are clear. A steady diet of feedback is much better than getting something once a year. Having the opportunity to prioritize and clarify conflicts in feedback is key. Hearing it firsthand is better than having it filtered.

The biggest minuses of this model are less clear. One could be that in round robin feedback, unless you spend several hours at it, it’s possible that some detail and nuance get lost in the name of prioritization. Another could be that so much transparency means that important feedback is hidden because the people giving the feedback are nervous to give it. One thing to note as a mitigating factor on this last point is that the feedback we’re talking about coming in a peer feedback session is all what I’d call “in bounds” feedback. When there is very serious feedback (e.g., performance or behavioral issues that could lead to a PIP or termination), it doesn’t always surface in peer feedback sessions – it takes a direct back channel line to the person’s manager or to HR.

The main conclusion I draw from studying this evolution is that feedback processes by design vary with culture. The more our culture at Return Path got deeper and deeper into transparency and into training people on giving/receiving feedback and training on the Difficult Conversations and Action/Design methodologies, the more we were able to make it safe to give tough feedback directly to someone’s face, even in a group setting. That does not mean that all companies could handle that kind of radical transparency, especially without a journey that includes increasing the level of transparency of feedback one step at a time. At Bolster, where the culture is rooted in transparency from the get go, we have been able to start the feedback journey at the Peer Feedback level, although now that I lay it out, I’m worried we may not be doing enough to make sure that the peer feedback format is meaningful enough especially around depth of feedback!