There’s been a growing cry for tech companies to add diversity to their leadership teams and boards, and for good reason. Those two groups are the most influential decision making bodies inside companies, and it’s been well documented that diverse teams, however you define diversity — diversity of demographics, thoughts, professional experience, lived experience — make better decisions. 

Gender, racial, and ethnic representation in executive teams and in board rooms are not new topics.  There’s been a steady drumbeat of them over the last decade, punctuated by some big newsworthy moments like the revelations about Harvey Weinstein and the tragic murder of George Floyd.  

It’s also true that in people-focused organizations, and most tech companies claim to be just that, it’s beneficial to have different types of leaders in terms of role modeling and visibility across the company. As one younger woman on my team years ago said, “if you can see it…you can be it!”

My company Bolster is a platform for CEOs to efficiently build out their executive teams and boards. But while nearly every search starts with a diversity requirement, many don’t end that way. 

Here’s why, and here’s what can be done about it. 

For boards, the “why” is straightforward. Board searches are almost never a priority for CEOs. They’re viewed as optional. Bolster’s Board Benchmark study in 2021 indicated that only a third of private companies have independent directors at all;even later stage private companies only have independent directors two-thirds of the time. That same study indicated that 80% of companies had open Board seats. The comparable longitudinal study in 2022 indicated that the overwhelming majority of those open board seats were still open. 

Independent directors are usually the key to diversity, as the overwhelming majority of founders and VCs are still white and male. It takes a lot of time and effort to recruit and hire and onboard new directors, and in the world of important versus urgent, it will always be merely important. Without prioritizing hiring independents, board diversity may be a lofty goal, but it’s also an empty promise. I wrote about my Rule of 1s here and in Startup Boards – I wish more CEOs and VCs took the practice of independent boards and board diversity seriously. The silver lining here is that when CEOs do end up prioritizing a search for an independent director, they are increasingly open to diverse directors, even if those people have less experience than they might want. That openness to directors who may never have been on a corporate board (but who are board-ready), who may be a CXO instead of a CEO, is key. Of the several dozen independent directors Bolster has helped match to companies in the past year, almost 70% of them are from demographic populations that are historically underrepresented in the boardroom.

Diversity is stalling for Senior Executive hiring for the opposite reason. Exec hires are usually urgent enough that CEOs prioritize them. And they frequently start their searches by talking about the importance of diversity. But Senior Executives are much more often hired for their resume than for competency or potential. Almost all executive searches start with some variation of this line, which I’m lifting directly from a prior post: “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to be hired. They have made a ton of money, and they have moved beyond that job in their career progression. So inevitably, the search moves on to look for the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people may or may not be easy to find or available, but they feel less risky. In the somewhat insular world of tech, those candidates are also far less likely to be diverse in background, experience, thought, or, yes, demographics.

Running a comprehensive executive search based on competencies, cultural fit, scale experience, and general industry or analogous industry experience is much harder. It takes time, patience, digging deeper to surface overlooked candidates or to check references, and probably a little more risk taking on the part of CEOs. And while CEOs may be willing to take some risk on a first-time independent director, fewer are willing to take a comparable level of risk on an unproven or less known executive hire. 

For some CEOs, the answer is just to take more risk — or more to the point, recognize that any senior hire carries risk along a number of dimensions, so there’s no reason to prioritize your narrow view of resume pedigree over any critical vector. For others, the answer may be to bring the focus of diversity in senior hires to “second level” leaders like Managers, Directors, or VPs, where the perceived risk is lower, and the willingness to invest in training and mentorship is higher. Those people in turn can be promoted over time into more senior positions. 

Not every executive or board hire has to be demographically diverse. Not every executive team or board has to have individual quotas for different identity groups, and diversity has many flavors to it. But without doing the work, tech CEOs will continue to bemoan the lack of diversity in their leadership ranks, and miss out on the benefits of diverse leadership, while not taking ownership for those efforts stalling.

I wrote part I of this post in 2011, and I feel even more strongly about it today. I generally keep this blog away from politics (don’t we have enough of that running around?), but periodically, I find some common sense, centrist piece of information worth sharing. In this case, I just read a great and very short book, Six Amendments: How and Why We Should Change the Constitution, by former Supreme Court Justice John Paul Stevens, that, if you care about the polarization and fractiousness going on in our country now, you’d appreciate.

If nothing else, the shattered norms and customs of the last several years should point people to the fact that our Constitution needs some revision. Not a massive structural overhaul, but some changes on the margin to keep it fresh, as we approach its 250th anniversary in the next couple decades.

Book Short: Sequel Not Worth It

Mastering the 7 Essentials of High Growth Companies, by David Thomson, was a poor sequel to the solid Blueprint to a Billion [review] [buy]– and not worth reading if you’ve read the original.  It was very short for its price and contained mildly interesting examples of “blueprint companies” that augmented the original book but didn’t uncover any new material or add any thinking to the mix.  Basically, it was like another couple chapters that should have been part of Blueprint.

It is not a bad buy in lieu of the original if you haven’t read either one yet, as Blueprint is a bit longer than necessary, but otherwise, you can skip this one.

On a side note – the author’s interactive scorecard is a decent diagnostic tool (though also, I am sure, a lead gen tool for his consulting business).

Thanks to my friend and long-time former Board member Jeff Epstein, I recently downed a new book, You’re in Charge – Now What?, by Thomas Neff and James Citrin.  I’m glad I read it.  But it was one of those business books that probably should have just been a Harvard Business Review article.  It’s best skimmed, with helpful short summaries at the end of every chapter that you could blow through quickly instead of hanging on every word. 

The authors’ 8-step plan is laid out as:

1. Prepare yourself during the countdown
2. Align expectations
3. Shape your management team
4. Craft your strategic agenda
5. Start transforming culture
6. Manage your board/boss
7. Communicate
8. Avoid common pitfalls

Ok fine, those make sense on the surface. Here are three things that really stood out for me from the book:

First, “working” before you’re officially working – the countdown period. I tried hard NOT to do this when I was between things, but I’m glad I did the things I did, and now, I wish I had done more. The most poignant phrase in the book is “scarce time available during your first hundred days.” That is an understatement. As my “to read” pile grows and grows and grows with no end in sight…I wish I had done more pre-work.

Second, remember that in every interaction, you are being evaluated as much as you are evaluating. And note that for many people, they will be thinking very critically, things like “do I want to work with this person…is he/she showing signs that he/she wants to work with me?” Yes, we all know as leaders, we live in a fishbowl. But I think that may be even more true during the first couple months on the job.

Finally, this phrase stood out for me: “Acknowledging and in some cases embracing your predecessor can sustain a sense of continuity within the organization and instill a sense of connectivity with employees’ shared past.” There is frequently a temptation to focus on things that need change, which invariably there are…and which invariably you will hear from people who are happy to find a willing new ear to listen to them. But this posture of acknowledge/embrace is especially true in my case, where my predecessor is the founder and 25-year CEO who continues on as our active chairman.

I know there are a ton of books like this on the market, and while I’ve only read this one, I’d say that if you’re starting a new CEO or executive-level job, this is a good one to at least skim to get some ideas.

A Sense of Urgency, by John Kotter, is a solid book – not his best, but worth a read and happily short, as most business books should be.  I originally was going to hold off on writing this post until I had more time, but the subject matter alone made me think that was a mistake and that I should write it while it’s fresh in my mind.  <g>

The three tools to fight complacency are the organizing framework for the book — bring the outside in, behave with urgency every day, and turn crises into opportunities — are all good thoughts, and good reminders of basic management principles.  But there were a couple other themes worth calling out even more.

First up, the notion that there is a vicious cycle at play in that urgency begets success which creates complacency which then requires but does not beget urgency.  The theme is really that success can drive arrogance, stability, and scale that requires inward focus — not that success itself is bad, just that it requires an extra level of vigilance to make sure it doesn’t lead to complacency.  I’ve seen this cycle at different times over the years in lots of organizations, and it’s one of the reasons that if you look at the original companies on the Dow Jones Industrials index when it was expanded from 12 to 30 around 100 years ago, only one of them (GE) still exists.

Second, that busy-ness can masquerade as urgency but actually undermines urgency.  A full calendar doesn’t mean you’re behaving with urgency.  Kotter’s example of an Indian manager is great:

If you watch the Indian manager’s behavior carefully and contrast it with the hospital executive’s, you find that the former relentlessly eliminates low-priority items from his appointment diary. He eliminates clutter on the agenda of the meetings that do make it into his diary. The space that is freed up allows him to move faster. It allows him to follow up quickly on the action items that come out of meetings. The time freed up allows him to hold impromptu interactions that push along important projects faster. The open space allows him to talk more about issues he thinks are crucial, about what is happening with customers and competitors, and about the technological change affecting his business.

Finally, Kotter’s theme of “Urgent patience” is a wonderful turn of phrase.  As he says,

It means acting each day with a sense of urgency but having a realistic view of time. It means recognizing that five years may be needed to attain important and ambitious goals, and yet coming to work each day committed to finding every opportunity to make progress toward those goals.

How true is that?  It’s not just that big ships take a long time to turn…it’s that big opportunities take a long time to pursue and get right.  If they didn’t…everyone would do them!  Urgent patience is what allows you to install a bias for action in your team without causing panic and frenzy, which is never productive.

Thanks to my friend Chad Dickerson for recommending this book, a great read as part of Operation Reboot Matt.

Book Short:  Internet True Crime

Fatal System Error: The Hunt for the New Crime Lords Who Are Bringing Down the Internet, by Joseph Menn (book, kindle) was a bit of a disappointment.  I was really hoping for more of an explanation of how the “business” of Internet crime works — what the economics are like, what the landscape/scope/sectors are like, who the players are.

What I got was a bit of a true crime novel, the story of Barrett Lyon and Andy Crocker, who are respectively a geek and a cop, and their very specific stories of tracking down a handful of internet criminals around a handful of technical tactics (DDOS attacks and botnets).  It wasn’t bad, the stories were ok and occasionally entertaining, but it was very narrow.

It felt to me like there is a much more interesting story to tell around criminals who USE the Internet to commit crimes as opposed to people attacking the infrastructure.  Has anyone ever run across a book like that?

Book Short:  And It’s Not Just Because I’m In It

Debbie Weil’s The Corporate Blogging Book is a good super quick read for any CEO or senior executive who is contemplating starting a blog — or even better, for those who have decided not to do so.

Weil’s writing style is great and very informal (blog-like, in fact) – a representative snippet is where she tells readers that there are two types of information to worry about posting on a blog, in her words, “stuff you don’t to reveal and stuff you could get sued for.”  And her range of topics is great and deals with issues head-on. Things like fear of losing control, time commitment, and ghost writing are all well covered.

Chapter 8 also includes a great Cliff’s Notes guide to web 2.0 technologies — RSS, podcasting, wikis, tagging — which is useful if you still Feel Like a Luddite about those things.

I did contribute a couple interviews to the book, as did most of the other oft-cited CEO bloggers like Mark Cuban and Jonathan Schwartz in whose company I am somewhat embarrassed and humbled to be. But don’t let that deter you from picking up a copy if you are in the target audience!

Book Short:  Way, Way Beyond Books

The Everything Store: Jeff Bezos and the Age of Amazon, by Brad Stone, was a great read.  Amazon is a fascinating, and phenomenally successful company, and Jeff is a legendary technology leader.  The Everything Store is a company and personal biography and totally delivers.

Forget about the fact that Amazon is now almost $100B in revenues and still growing like mad.  I find it even more amazing that a single company could be the largest ecommerce site on the planet while successfully pioneering both cloud computing services and e-readers.  The stories of all these things are in the book.

As a CEO, I enjoyed reading more of the vignettes behind the things that Amazon is reputationally known for in the tech world – doors as desks, their unique meeting formats, the toughness of the culture, the extensive risk taking of growth over profits, and what works and does not work about Bezos’ authoritative and domineering style.  And it’s always great to be reminded that even the biggest and best companies had to cheat death 10 times over before “arriving.”

This is good fun and learning for anyone in the business world.  It reminded me most of Walter Isaacson’s biography of Steve Jobs ,which I wrote about here, although it’s more of a company history and less of a biography than the Jobs book.

Book Short:  Shamu-rific

I re-read an old favorite last night in preparation for a management training course I’m co-teaching today at Return Path:  Ken Blanchard’s Whale Done! The Power of Positive Relationships.  I was reminded why it’s an old favorite.  It has a single concept which is simple but powerful.  And yes, it’s based loosely on killer whale  training tactics.

Accentuate the positive.

The best example in the book is actually a personal one more than a professional one.  The main character of the book has a “problem” in that he chronically works late, then comes home and gets beat up by his wife about coming home so late.  The result?  No behavior change — and probably even a reinforcement of the behavior because, after all, who wants to come home and get beat up?  The change as a result of the new philosophy?  The wife thanks her husband when he does come home at a more reasonable hour, makes him a nice dinner, etc. which makes the husband WANT to come home earlier.

That’s probably a poor paraphrasing of the story, and as I’m typing the story out here, boy does it sound a bit 1950s in terms of its portrayal of gender role stereotypes.  Nonetheless, I think it makes the point well.

Try it out sometime at work (or at home).  Pick a behavior you want to see more of out of a direct report, especially one that’s linked to another behavior you don’t like.  Accentuate the positive.  Make the person WANT to do more of it.  And watch the results!

Book Short:  Culture is King

Tony Hsieh’s story, Delivering Happiness (book, Kindle), is more than just the story of his life or the story of Zappos. It’s a great window into the soul of a very successful company and one that in many ways has become a model for great culture and a great customer service model.  It’s a relatively quick and breezy read, and it contains a handful of legendary anecdotes from Zappos’ history to demonstrate those two things — culture and customer service — in action.

As Hsieh himself says in the book, you can’t copy this stuff and believe it will work in your company’s environment as it does in Zappos’.  You have to come up with these things on your own, or better yet, you have to create an environment where the company develops its own culture and operating system along the broad lines you lay out.  I think Return Path has many similarities with Zappos in how we seek out WOW experiences and in our Core Values, as well as the evolutionary path we took to get to those places.  But as much as I enjoyed reading about a like-minded company, I also recognized the specific things that were different and had a good visceral understanding as to WHY the differences exist.

It is the rare company that gets to $1 billion in revenue ever – let alone within a decade.  For that reason alone, this is a worthwhile read.  But if you are a student of organizational culture and believe in the power of values-driven organizations, this is good affirmation and full of good examples.  And if you’re a doubter of the power of those things, this might just convince you to think twice about that!

Book Short:  Legal Aid

The Entrepreneur’s Guide to Business Law, by Constance Bagley (HBS) and Craig Dauchy (Cooley Godward), while not exactly a page-turner, is a great reference book for even experienced CEOs. It’s pretty broad in its coverage of all major legal issues an entrepreneur will face, from patent law to firing employees.

Remember, you may make fun of lawyers on occasion or grips about their fees, but they DID attend law school for three years, after all. If nothing else, the $20 on this book will almost certainly save you at least 10x that in reduced legal fees someday, for something.