Should You Have a Board?

As I mentioned last week, Fred’s post from a few months ago about an M&A Case study involving WhatCounts had a couple of provocative thoughts in it from CEO David Geller.  The second one I wanted to address is whether or not you should have take on institutional investors and have a Board.  As David said in the post:

Fewer outsiders dictating (or strongly suggesting) direction means that you will be able to pursue your goals more closely and with less friction

Although I have a lot of respect for David, I disagree with the notion that outsiders around the Board table is inherently bad for a business, or at least that the friction from insights or suggestions provided by those outsiders is problematic.

While that certainly CAN be the case, it can also be the case that outside views and suggestions and healthy debate, as long as incentives are aligned, people are smart, and founders manage the discussion well, can be enormously productive for a business.  I recognize that I’ve been very lucky that the Board members we’ve had at Return Path over the years have not been dogmatic or combative or dumb, but I do think selection and management of Board members is something very much in a CEO’s control.

But beyond the issue of who sets the agenda, Boards create an atmosphere of accountability for an organization, which drives performance (and many other positive qualities) from the top down in a business.  Budgeting and planning, reporting on performance, organizing and articulating thoughts and strategy – all these things are crisper when there’s someone to whom a CEO is answering.

As a telling case in points, I’ve known two CEOs over the years in the direct marketing field who have more or less owned their companies but insisted on having Boards.  While I’m not sure if those Boards had the ultimate power to remove the owner as CEO (which is the case in a venture-dominated Board and of course an important distinction), I do know that having a Board served them and their organizations quite well.  The fact that they didn’t have to have “real Boards” but chose to anyway – and ran spectacular businesses – is a good controlled case study for me in the value of this discipline.

How Much Marketing Is Too Much Marketing?

It seems like a busy holiday season is already underway for marketers, and hopefully for the economy, shoppers as well.  Just for kicks, I thought I’d take a rough count of how many marketing messages I was exposed to in a given day.  Here’s what the day looked like:

5:30 a.m. – alarm clock goes off with 1010 WINS news radio in the middle of an ad cycle – 2 ads total.  Nice start to the day.

5:45-6:30 – in the gym, watching Today In New York News on NBC for 30 minutes, approximately 6 ad pods, 6 ads per pod – 36 ads total.  So we’re at 38, and it’s still dark out.

7:00 – walk to subway and take train to work, then walk to office from subway.  Probably see 6 outdoor ads of various kinds on either walk, then about 8 more on the subway within clear eyeshot – 20 ads total.

7:30 – quick scan of My Yahoo – 2 ads total.

7:32 – read Wall St. Journal online, 15 page views, 3 ads per page – 45 ads total.

7:40 – Catch up on RSS feeds and blogs, probably about 100 pages total, only 50% have ads – 50 ads total (plus another 25 during the rest of the day).

7:50 – Sift through email – even forgetting the spam and other crap I delete – 10 ads total (plus another 10 during the rest of the day).

8:00-noon – basically an ad free work zone, but some incidental online page views are generated in the course of work – 25 ads total, plus a ton of Google paid search ads along the way.

Noon-1 p.m. – walk out to get lunch and come back to office, so some outdoor ads along the path – 12 ads total.

1-7 p.m. – same work zone as before – 25 ads total, plus lots of Google.

7 p.m. – walk to Madison Square Garden to see the Knicks get clobbered by Milwaukee, see lots of outdoor ads along the way – 20 ads total.

7:30-9:30 – at the Garden for the Knicks game, bombarded by ads on the scoreboards, courtside, sponsorship announcements, etc.  Approximately 100 ads total (and that’s probably being exceptionally generous).

9:30 – subway ride and walk home – 14 ads total.

10:00 – blitz through episodes of The Daily Show and West Wing in TiVo.  8 minutes of :30 advertising per half hour, or 48 ads total, fortunately can skip most of them with TiVo.

11:00 – flip through issue of The New Yorker before bed – 50 ads total.

Total: 492 ads.

I’m sure I missed some along the way, and to be fair, I am counting the ads I skipped with TiVo — but hey, I’m also not counting all the ads I saw on Google, so those two should wash each other out.  On the other hand, if I drove to and from work in California, I’d have seen an extra 100 billboards, and if I read the New York Times print edition, I’d have seen an extra 100 print ads.

Approximate cost paid to reach me as a consumer today (assuming an average CPM of $10): just under $5.  Sanity check on that — $5/day*200 million Americans who are “ad seers”*365 days is a $365 billion advertising industry, which is probably in the right ballpark.

What are the two ads I consciously acted on?  An offer from LL Bean through email (I’m on their list) for a new fleece I’ve been meaning to get, and a click on one of the Google paid search results.  No doubt, I subconsciously logged some good feelings or future purchase intentions for any number of the other ads.  Or at least so hope all of the advertisers who tried to reach me.

What’s the message here?  A very Seth Godin-like one.  Nearly all of the marketing thrown at me during the day (Seth would call it interrupt marketing) — on the subway, at the Garden, on the sidebar of web pages — is just noise to me.  The ones I paid attention to were the ones I WANTED to see:  the email newsletter I signed up for from a merchant I know and love; and a relevant ad that came up when I did a search on Google.

Brand advertising certainly has a role in life, but permission and relevance rule the day for marketers.  Always.

First in my series of posts around creating the best place to work  is to Surround yourself with the best and brightest.  This one is simple.  Build the best team you can possibly build…as you need it.

As a founder, you may be the best person at doing everything in your company, especially if you are a technical founder.  But as my long-time Board member at Return Path Greg Sands always says, when the organism grows, cells start to specialize.  Eventually, you need a liver and a brain.  Just like companies need a head of sales and a CFO (not to imply that Anita likes the occasional cocktail or that Jack likes math – turns out both like both).

How does this come into play as a CEO?

-Don’t be afraid to hire people better than you at their specialty – older, wiser, more experienced, more expensive

– Check references carefully – don’t get suckered in by resume or rolodex – some successful big company people don’t actually know how to do work or build a business, so you have to dig and find back-channel references

– Don’t overhire before you’re ready, but especially as a start-up, better to hire 3 months before you need the position, not 6 months too late

-Remember that you are the CEO.  Even if you hire very experienced people in specific roles, you have the best global view of everything going on in the company.  And you need to pay attention to people on your team and actively manage them, even experts who are older or wiser than you are

Surrounding yourself with the best and brightest can be daunting and even threatening to some CEOs.  But you have to do it to grow your business.  And you have to keep doing it as you keep growing your business (and your staff has to do the same!).

Sometimes the work we do as CEOs, leaders, management teams is glamorous, and sometimes it’s not. But it all matters. One thing we tried to do at Bolster this past year is to really amp up employee benefits. The war for talent is real. The Great Resignation is real. Sometimes startups like ours have natural advantages in terms of attracting and retaining talent such as being made up of letting people in on the ground floor of something, having small teams so individual impact is easy to see, being mission-driven and full of creativity and purpose, and having equity to give that could be very valuable over time. But sometimes startups like ours have natural disadvantages around recruiting like having less certain futures, being relatively unknown to potential employees, being unable to pay huge salaries in the face of the Googles and Facebooks of the world, and having limited career path options since the teams are so small.

My co-founders and I have always been big believers in innovating People Practices. We did an enormous amount of work around this at our prior company, Return Path, which has been pretty well documented and we feel was very successful. Things like our People First philosophy of investing in our team, an extraordinary amount of transparency in the way we ran the company, a sabbatical policy, an open vacation policy, a peer recognition system, 360 reviews (I’ve written about this a lot, but I don’t have a great single post on it – this one is good enough and has some links to others), and an open expense policy.

Most of those things, when we started doing them 20 years ago, were revolutionary. We had our own version of the then-infamous Netflix deck even before we saw the Netflix deck. But today, many of those people practices are more common, not quite table stakes, but not exactly unique either. So this year when we set out to do our annual retrospective and planning process, we decided to try to innovate on a fairly standard topic for people, employee benefits. Although there’s not a lot of room for innovation on this topic, we are doing a few things that new and existing employees alike have told us are noteworthy, so I thought I would share them here.

We started by getting the basics right. We have a good solid health plan, dental plan, vision, transit benefits, etc. And we are paying 100% of the basic plan and allowing employees to pay more for a premium plan. That’s not the innovative part.

Next, we decided to max out the HSA contribution. HSAs and FSAs are some of those things that people don’t really think about, or they think “oh that’s great, employees can set aside health care expenses pre-tax.” But employer contribution to them matters, especially because the plans are portable. So we are giving people whatever the legal limit is towards their HSA, something in the neighborhood of $7k/year for a family plan or $3k for an individual plan. This is real money in people’s pockets, and it takes away from fears and concerns about health and wellness.

Next, we decided to begin addressing two things we felt were always weird quirks or inequities in benefit plans. One is the fact that employees who DO take advantage of your benefits program essentially get a huge additional amount of compensation than employees who DON’T because they are on their spouse’s plan. So we decided to give all employees who DON’T use our benefits program a monthly stipend. The amount doesn’t quite equal what we would be paying for their health insurance (which varies widely for employees based on single vs. family plans), but it’s a material number. So those people who aren’t on our plan still receive a healthcare proxy benefit from us.

Another (and the final thing I’ll talk about today) was instituting a 401k match, but doing so with a dollar cap instead of a percentage cap. Percentage caps FEEL fair, but they’re not fair since the company ends up paying more money towards the retirement plan of the people who earn the most money and who presumably need that benefit the least. The IRS tries to help do this leveling with their nondiscrimination testing, but that doesn’t come close to achieving the same outcome because it’s about employee contributions, not employer matches. By instituting a dollar cap, we are making the statement that we value all employees’ retirements equally. Incidentally, this simple change is proving to be very difficult to implement since our systems and benefits providers aren’t set up to do it, but we will persevere and find workarounds and get it right.

Investing in our people is critical to who we are as a business, and if you take your business seriously, it should be in your playbook as well. Benefits sound like a dumb area in which to innovate since they’re very common across all companies other than the percentage of the premium covered…but there’s still room for creativity even in that field.

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.

Alter Ego

A couple people have asked me recently how I work with an Executive Assistant, what value that person provides, and even questioned the value of having that position in the company in an era where almost everything can be done in self-service, lightweight ways. At my old company (in the 90s), each VP-level person and up had a dedicated assistant – the world certainly doesn’t require that level of support any more.  In our case, Andrea has other tasks for the company that take up about half of her time.

I happen to have the absolute best, world class role model assistant in Andrea, who I’ve had the pleasure of working with for almost seven years now (which is a reminder to me that she has a sabbatical coming up soon!).

This is an important topic.  It’s tempting for CEOs of startups, and even companies that are just out of the startup phase, to want to do it all themselves…or feel like they don’t need help on small tasks.  My argument against those viewpoints is that your time is your scarcest resource as the leader of an organization, and anything you can do to create more of it for yourself is worthwhile.  And a good assistant does just that – literally creates time for you by offloading hundreds of small things from your plate that sure, you could do, but now you don’t have to.

I asked Andrea to write up for me a list of the major things she does for me (although she didn’t realize it was going to turn into a blog post at the time).  I’ll add my notes after each bullet point in italics on the value this creates for me.

• Updates and maintains calendar, schedules meetings and greets visitors – My calendar is like a game of sudoku sometimes.  I can and do schedule my own things, but Andrea handles a lot of it.  She also has access to all my staff’s calendars so she can just move things around to optimize for all of us.  Finally, she and I review my calendar carefully, proactively, to make sure I’m spending my time where I want to spend it (see another item below)
• Answers and screens direct phone line – The bigger we get, the more vendors call me. I can’t possibly take another call from a wealth management person or a real estate broker.  Screening is key for this!
• Plans and coordinates company-wide meetings and events – This is an extension of managing my calendar and accessing other executives’ calendars…and a pretty key centralized function.
• Plans and coordinates Executive Committee offsite’s – Same, plus as part of my theme of “act like you’re the host of a big party,” I like this to be planned flawlessly, every detail attended to.  I do a lot of that work with Andrea, but I need a partner to drive it.
• Collects and maintains confidential data – Every assistant I’ve ever had starts by swearing an oath around confidentiality.
• Prepares materials for Board Meetings and Executive Committee meetings – Building Board Books is time consuming and great to be able to offload.  We put together the table of contents, then everyone pours materials into Andrea, and poof!  We have a book.  For staff meetings, she manages the standing agenda, changes to it, and the flow of information and materials so everyone has what they need when they need it to make these meetings productive from start to finish.  In our case, Andrea is part of the Executive Committee and joins all of our meetings so she is completely up to speed on what’s going on in the company – this really enables her to add value to our work.  She’s also not just a passive participant – some great ideas have come from her over the years!
• Coordinates and books travel (domestic and international) – Painful and time consuming, not because Expedia is hard to use but because there is a lot of change, complexity, and tight calendars to manage and coordinate for certain trips.  And while it takes a while to get an assistant up to speed on how you like to travel or how you think about travel, this is a big time saver.
• Prepares expense reports – Same thing – you CAN do it, but easier not to.
• Manages staff gifts and Anniversary presents for all employees – This is a big one for me.  I send every employee an anniversary gift each year and call them.  Once a month, a stack of things to sign magically appears on my desk…and then gets distributed.  Andrea manages the schedule, the inventory of gifts, the distribution of gifts to managers.
• Manages investor database – I assume someday we’ll have a system for this, but for now, IR is a function that Andrea coordinates for me and Jack, my CFO.
• Assist Executive Committee with project as needed – The person in this role for you ends up being really valuable to help anyone on your staff with major projects.  Good use of time.
• Prepares Quarterly Time Analysis for CEO – This is a big one for me.  Every quarter, Andrea downloads my calendar and classifies all of my time, then produces an analysis showing me where I’m spending time my classifications are – Internal, External, non-RP, free, travel, Board/Investor.  This really helps us plan out the next quarter so I’m intentional about where I put my hours, and then it helps her manage my calendar and balance incoming requests.
• Help with communications – This one was not on Andrea’s list, but I’m adding it.  She ends up drafting some things for me (sometimes as small as an email, sometimes as large as a presentation, though with a lot more guidance), which is helpful…it’s always easier to edit something than create it.  I also usually ask Andrea to read any emails I send to ALL ahead of time to make sure they make sense from someone’s perspective other than my own, and she’s very helpful in shaping things that way.

This may not be true of all companies at all sizes and stages, but for companies like ours, I’d classify a great assistant as a bit of an alter ego, one definition of which is “second self” – literally an extension of you as CEO.  That means the person is acting AS YOU, not just doing things FOR YOU.  Think about the transitive property here.  Everything you do as CEO is (in theory) to propel the whole company forward.  So everything your alter ego does is the same.  A great assistant isn’t just your administrative assistant.  A great assistant is an overall enabler of company success and productivity.  You do have to invest a lot of time in getting someone up to speed in this role for them to be effective, and you have to pay well for performance, but a great assistant can literally double your productivity as CEO.

Symbolism in Action

A couple months ago, I wrote about how the idiots who run the Big 3 US automakers in Detroit don’t have a clue about symbolism — the art or the science of it.  Yesterday, I wrote about how I think the non-headcount cuts to G&A that we’re making at Return Path during these challenging economic times will be positive for the company in the long run.  The two topics are closely related.

Obama announces on Day 1 that White House staffers who make more than $100k won’t be getting a pay raise this year.  Presumably all of those people just started their jobs on January 20 and wouldn’t be eligible for a raise until 2010.  Return Path cuts pilates classes in its Colorado office — an expense that must cost around $3,000/year.  Practically speaking, it won’t make a difference to our budget one way or another.  Microsoft lays off 1,400 people — a real number, certainly for those families — but that’s the equivalent of Return Path laying off 2 people. 

Sometimes the symbolic is just that.  It is something designed to send a signal to others, and not much more.  You could argue that all three examples above mean nothing in reality, so they were just symbolic.  A waste of time.

You can also make the argument that sometimes, when done right, symbolism turns into action as it motivates or serves as a catalyst for other changes.  Obama’s cuts may be fictitious, but they set the tone for broader action across a 2mm person bureaucracy.  Pilates in the office?  Feels too excessive these days, even for a company obsessed with its employees and their well being, in an era where we’re cutting back other things that are more serious.  Microsoft has gobs of cash and doesn’t need to worry about its future, but it wants to tell the other 99% of its employee population that it’s time to buckle down and fly straight.  And they will.

Anyone who thinks the synbolic doesn’t influence the practical should think again.  Or just talk to Caroline Kennedy about the impact of her admission that she hadn’t voted in years on her political ambitions.

Closer to the Front Lines, II

Last year, I wrote about our sabbatical policy and how I had spent six weeks filling in for George when he was out.  I just finished up filling in for Jack (our COO/CFO) while he was out on his.  Although for a variety of reasons I wasn’t as deeply engaged with Jack’s team as I was last year with George’s, I did find some great benefits to working more directly with them.

In addition to the ones I wrote about last year, another discovery, or rather, reminder, that I got this time around was that the bigger the company gets and the more specialized skill sets become, there are an increasing number of jobs that I couldn’t step in and do in a pinch.  I used to feel this way about all non-technical jobs in the early years of the company, but not so much any more. 

Anyway, it’s always a busy time doing two jobs, and probably both jobs suffer a bit in the short term.  But it’s a great experience overall for me as a leader.  Anita’s sabbatical will also hit in 2010 — is everyone ready for me to run sales for half a quarter?

The Good, The Board, and The Ugly, Part II

Much has been written of late on various VC and entrepreneur blogs on effective management of a Board of Directors, Board materials, running good Board meetings, and the like.  A couple years ago, I even wrote out a few tips for those things myself.

But here’s one critical ingredient of a good Board you won’t find in all those posts:  have fun!  This picture was from today’s Halloween Board meeting at Feedburner…as one of Dick’s colleagues labeled it, The Dawn of the Living Costolos.

Happy Halloween!

I’ve written a lot about Boards this past year related to Bolster’s work in helping founders/CEOs build great boards:

• The New Way to Scale a Board of Directors
• My New Startup Board Mantra – 1:1:1
• The Startup Ecosystem Needs More Independent Board Members – That’s the Clearest Path to Having Better and More Diverse Boards
• Startup Boards eBook: How to Build Your Board
• Startup Boards eBook: How to Succeed in Your First Board Role

But more recently, I’ve been thinking a lot about Board effectiveness, as I’ve been working with Brad Feld and Mahendra Ramsinghani on a second edition of Startup Boards, which will be published in mid-2022. And in the middle of our feverish writing and editing, Reid Hoffman sent Brad a great document which I want to amplify here:

Some of these rituals are more important than others (or at least more widely applicable), but they’re all worth reading. I am definitely going to start incorporating some version of the “Dory and Pulse” ritual into my meetings to make sure we’re covering everything that each director wants to cover in meetings (or answer smaller things ahead of time).

Thanks to Reid for this great contribution to the world of Startup Boards.

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.