(This post also appeared on Bolster.com)

As we wrote in our Founding Manifesto, Bolster was started in part to create a new way for startup and scaleup CEOs to think about growing their leadership teams.

Why do CEOs need help with this?

CEOs of any company have too many things to do at all times. This is even more true at startups and scaleups, which by definition are more fast-paced, dynamic, CEO-driven, and thinly staffed. All those challenges point directly to the specific challenge CEOs have with their leadership team.

Think about the journey of a company from a founding team to 50 employees. My long time friend and former board member Greg Sands once compared the phenomenon

of companies growing out of the startup stage to cell development in small organisms. Amoeba or paramecia consist of one cell, and that cell has to do everything: eat, move, sense its surroundings, and respond accordingly. When the cell divides, the new cells still need to do everything – they’re just attached to other cells. As organisms grow more complex, individual cells need to specialize. And when things get really complex, you need a liver, a spleen, a stomach, and a pancreas. By and large, startups work the same way. In the early stages, you have to hire generalists who are both willing and able to take on dozens of tasks at once. Your developers will have to speak with potential customers; your accountants will have to give advice on product direction; and the born salesperson on your team will need to put the phone down a few hours a day and set up a new employee’s computer. That’s a really different team than when you need functional managers on top of engineering, sales, etc. — not to mention needing strategic leadership of those functions as the company grows from 50 to 100 to 250 to 500 employees.

That’s the journey that startup and scaleup CEOs are on. It’s less of a journey and more of a roller coaster ride. Jason is running HR today…but tomorrow, the job of “head of HR” will be different, and Jason might or might not be capable of it. Then your VP Finance Sally gets lured away by an even hotter and sexier new startup and leaves a sudden, gaping hole on your team. Then cracks start to show up with the job Jamie is doing as your marketing director and you lose confidence that your upcoming product launch is going to be a success. Every time one of these events happens – whether it’s an actual event, or just an “aha moment” for you as CEO, you add something to your plate. You add tasks to take over work yourself. You add the task of finding a new person. You add stress from having to deal with one more critical thing.

Leveling up a leadership team is probably the hardest part of the CEO’s job. 

Why don’t current solutions meet the CEO’s needs? Well, of course they do, sometimes. The problem is that the current solutions either aren’t tailored to the needs of startup or scaleup CEOs, or they’re ad hoc and inefficient. Executive search is slow and expensive, and it produces expensive full-time executives. And no matter how good an executive search firm is, I’ve never met a CEO who has a better than 50% success rate in hiring new leaders from the outside. Ever. Add all that up – expensive, slow, medium success rate, and perhaps most important for a startup CEO, leaving you with expensive full-time headcount in multiple areas of your company – that is not a recipe for startup success when you’re sweating your burn rate.

Frequently, the CEO just taps her network for execs or for on-demand executives like the ones Bolster places — that could be asking board members or friends or advisors for suggestions. Quite frankly, those suggestions stand a better chance of success than transactional executive search since the candidate referral source is usually somewhat of an insider. But those searches are really disorganized or one-off. When a CEO turns to their network for spot help, they often aren’t running a comprehensive process, creating a serious job spec, seeing a broad set of candidates for comparisons, and the like. 

Our job at Bolster is to make all of this easier and lighter weight. The rise of the gig economy means that startups no longer need to rely on the painful binary choice of “the person/opening I have today” and “the expensive full-time exec coming in from the outside.”The new way to scale an executive team is with a mix of interim executive talent to quickly fill gaps, fractional executive talent to provide strategic oversight and guidance to a team, part-time, functional mentors/coaches/advisors to advise a less experienced functional leader, project-based consultants to fill in specific holes, and yes, the occasional full-time outside hire, possibly via a search firm (or if your fractional CXO loves your company and joins full-time!). 

With Bolster, you have a network of all those types of talent, well curated and well profiled, available for near-instant matches and near-instant start dates – and a suite of tools and services designed to help you proactively identify your needs across all your functional areas so you’re never scrambling your way out of a tight spot.

What about the existing team? If you’re a leader inside a startup or scaleup, Bolster is ALSO created for you. The painful binary choice CEOs face that I wrote above is particularly painful for you if you’re no longer scaling quickly enough. Frequently, promising junior people are layered or shuttered aside because the CEO doesn’t have the time, or the functional expertise required, to coach or mentor the person to success. Bolster creates an easy mechanism for CEOs to help pinpoint the areas in which you need growth and development as well as an easy way to find either temporary leadership or a function-specific advisor/mentor/coach to help you grow with the role and with the company.

The best startup CEOs I know are the ones who are already using multiple types of on-demand talent at the same time to help their companies along that journey from single-cell to complex organisms. I believe three years from today, the frequent usage of this kind of talent will move from the realm of early adopters to mainstream. The ones who embrace it first will have a competitive advantage.

Stuck In Legal, Responses

Well, I certainly struck a nerve with my Stuck In Legal rant/post last week.  As of now, there are 32 comments on the blog — my typical post generates 0-1 — and I've picked up between 50 and 75 new followers on Twitter, probably mostly because Fred tweeted about the post. 

Most of the comments on the blog were cheering me on; a couple were from lawyers, one well reasoned and another just a counter rant against stupid business people that had one or two good points buried in it.  You can certainly click through the link above if you want to read them.

But two comments didn't get put on the blog, which I thought I'd post here.  Keep the good thoughts coming on this topic.  It's an important one.

First, Jonathan Ezor (a professor of law and technology) posted his response — not a rebuttal — on the Business Week blog here.  He makes some very good points about how both sides, businessperson and counsel, can work better together to eliminate a bunch of the hassles I noted in my original post.

Second, Joe Stanganelli, a lawyer, emailed me the following, which was too long for my Intense Debate comment software to handle:

In defense of my profession…

EXPLANATIONS:

•Why companies' legal departments or outside counsel aren't directed to be as efficient in doing their work as their other departments

How exactly do you mean?  I'm not sure this is true.  Given the average amount of hours our profession works as it is, we *have* to be efficient.

I can tell you, however, that a huge pet peeve of us lawyers is when our clients essentially say (typically when they’re being billed hourly), "Gee, I want an answer to this very complex legal question that will require a lot of research because no statutes or case laws are directly on point, but don't spend a lot of time on it."

This is a bit like saying, “Look, don’t spend a lot of time on this transplant…I’ve got a meeting in an hour, and I’m trying to save money besides."

Also bear in mind that lawyers are not widget-makers or assembly line workers.  We aren’t even (usually) executive decision-makers.  We are in the knowledge and information industry.  We read, we think, and we write.  If you can provide us with some tips as to how to read, think, or write more efficiently, we would be delighted to hear them.

•Why companies insist on using their standard form of agreement if they're going to staff a legal department to review contracts anyway (this clearly wouldn't work if everyone in the world behaved this way)

The standard form of agreement has already (presumably) been determined by the company’s legal department to be the best form for the company's interests as part of the legal department’s careful legal analysis (i.e., the job they are paid to do).  Often, however, other companies, clients, etc. don’t use the standard form, or send their own form, or modify the standard form, or any number of other idiosyncrasies can happen with the execution of a contract.  All of these things have legal ramifications and have been the subject of past litigation.

•Why lawyers insist on answering questions with "because that's how all our contracts are" instead of applying their brains and logic to situations

(I'll try not to take too much offense at that last part.)

This generally happens because the answer “because that’s how all our contracts are” is a lot easier to say than to give the CEO a crash course in contract law.  It’s not fair, but it’s true.

A good lawyer, however, should at least be able to explain to boil it down to a few bullet points without being arrogant about it.

•Why business people seem to have no leverage with their legal departments, especially in larger companies, therefore surrendering the negotiation of business terms and the timing of relationship launches, technology usage, etc. to lawyers

This criticism is, if you’ll forgive me for saying so, a bit mind-blowing.  It’s not a matter of “leverage" at all.

Companies have legal departments as a preventative measure because they recognize that the best time to hire a lawyer is before you actually need one.  Most of law practice, in fact, is this “preventative law” and compliance work.  It saves the client (in this case, the company) time and money down the road by staving off lawsuits and liability.

These lawyers are in the business of protecting their clients from themselves – which the clients willingly pay them for because the clients (usually) recognize that they did not go to law school, pass the Bar Exam, and gain years of experiencing practicing law.

So when a company wants to launch a potentially harmful product via a distribution agreement that allows the distributor to get more money than he should because of a technicality, the legal department has to step in and tell the company, “YOU WILL GET SUED IF YOU DO THIS AND LOSE X AMOUNT OF DOLLARS!!!” or they aren’t doing their jobs.

A lawyer is a counselor – an advisor.  Any leader who totally disregards his advisors is not a good leader.

Again, this is not a matter of not having leverage with legal departments; it is a matter of not being able to change the law.

Please don’t shoot the messenger.

•Why in-house lawyers make the same dumb changes to wording and formatting that lawyers who bill by the hour make

The law is the law is the law; how the lawyer gets paid does not impact what the law is.  Those “dumb changes” are tried and true terminology that mean certain things in the courts and (usually) all the lawyers and judges know what they mean.  If the lawyers left it alone, your document or contract would potentially (perhaps even likely) mean something totally different.

Overall, please recognize that lawyers – at least in the legal department / “preventative law” context that you discuss – are in the risk management and compliance business.  They don’t make the law (at least, not the ones who work for you); they’re simply the guides who are navigating you – the layperson – through the legal system (one that took us years to understand).

After all, if you were blind, and you had a seeing-eye dog, would you get mad at the seeing-eye dog for not letting you cross the street when it’s a green light and a Mack truck is coming down the road?  Would you think that seeing-eye dogs were conspiring against you to not let you cross the street?

I will say this, though: Joshua Baer makes a great point.  A good lawyer should be able to provide you with a list of options, and explain (at least in a rudimentary fashion) the dollars-and-cents consequences of each one.  As J.P. Morgan said, “Well, I don't know as I want a lawyer to tell me what I cannot do. I hire him to tell how to do what I want to do.”

Counter Cliche:  Win The Peace

Fred’s VC cliche of the week this week is a good one, Hope for the Best and Prepare for the Worst.  It’s certainly true, as he says, for startups going through a financing, and in many other instances.  I may regret mixing business and politics here, but since Fred has done that before (with the same caveat), I’ll give it a shot as well.

As important as it is to prepare for the worst, entrepreneurs and politicians alike need to make sure they’re also planning to win the peace — in other words, planning for a successful outcome. 

How much happier would we be as a country at war right now if our administration had had a full plan in place for what to do after they toppled Saddam?  Similarly, CEOs need put some cycles against scenario planning for successful outcomes so they’re not caught flat footed when things go well.  How can lack of planning to win the peace come back to bite you?  Here are a few ways:

– You’re not staffed properly to support a big contract that comes in — and you have no pipeline of candidates or contractors to backfill

– You don’t have media buys lined up for an marketing campaign you want to run as soon as the financing closes

– You haven’t started an integration plan before a tenuous acquisition closes, so integration doesn’t happen quickly enough

There are certainly other examples as well, in war as in comapny-building, but what it all comes down to is the need to scenario plan for best cases as well as worst cases.  It’s all about avoiding costly lead times.

Secrets to Yawn-Free Board Meetings

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

The objective of board meetings should always be to have great conversations that help you and your executive team think clearly about the issues in front of you, as well as making sure your directors have a clear and transparent view of the state of the business. These conversations come from a team dynamic that encourages productive conflict. There’s no sure-fire formula for achieving this level of engagement, but here are three few guidelines you can follow to increase your chances.

Schedule board meetings in advance, and forge a schedule that works. Nothing is more disruptive – or more likely to drive low turnout – than last minute scheduling. Make sure you, or your executive assistant, knows board members’ general schedules and travel requirements, and whether they manage their own calendar or have their own executive assistant. Set your board meeting schedule for the year in the early fall, which is typically when people are mapping out most of their year’s major activities. If you know that one of your board members has to travel for your meetings, work with the CEOs of the other companies to coordinate meeting dates. Vary the location of meetings if you have directors in multiple geographies so travel is a shared sacrifice.

In the startup stage of our business at Return Path, we ran monthly meetings for an hour, mostly call-in. In the revenue stage, we moved to six to eight meetings per year, two hours in length, perhaps supplemented with two longer-form and in-person meetings. As a growth stage company, we run quarterly meetings. They’re all in-person, meaning every director is expected to travel to every meeting. We probably lose one director each time to a call-in or a no-show for some unavoidable conflict, but, for the most part, everyone is present. We leave four hours for every meeting (it’s almost impossible to get everything done in less time than that) and sometimes we need longer.

Many years, we also hold a board offsite, which is a meeting that runs across 24 hours, usually an afternoon, a dinner, and a morning, and is geared to recapping the prior year and planning out the next year together. It’s especially exhausting to do these meetings, and I’m sure it’s especially exhausting to attend them, but they’re well worth it. The intensity of the sessions, discussion, and even social time in between meetings is great for everyone to get on the same page and remember what’s working, what’s not, and what the world around us looks like as we dive into the deep end for another year.

Build a forward-looking agenda. The second step in having great board meetings is to set an agenda that will prompt the discussion that you want to have. With our current four-hour meetings, our time allocation is the following:

I. Welcomes and framing (5 minutes)

II. Official Business (no more than 15 minutes unless something big is going on)

III. Retrospective (45 minutes)

a. Target a short discussion on highlighted issues

b. Leave some time for Q&A

IV. On My Mind (2 hours)

a. You can spend this entire time on one topic, more than one, or all, as needed.

b. Format for discussions can vary—this is a good opportunity for breakout sessions, for example.

V. Executive Session (30 minutes)

This is your time with directors only, no observers or members of the management team (even if they are board members).

VI. Closed Session (30 minutes)

This is director-only time, without you or anyone else from the management team.

This agenda format focuses your meeting on the future, not the past. In the early years of the business, our board meetings were probably 75 percent “looking backwards” and 25 percent “looking forwards.” They were reporting meetings—reports which were largely in the hands of board members before the meetings anyway. They were dull as anything, and they were redundant: all of our board members were capable of processing historical information on their own. Today, our meetings are probably ten percent “looking backwards” and 90 percent “looking forwards”—and much more interesting as a result.

Separate background reading and presentation materials. Finally, focus on creating a more engaging dialogue during the meeting by separating background reading from presentation materials. In our early days, we created a huge Powerpoint deck as both a handout the week before the meeting and as the in-meeting deck. That didn’t create an engaging meeting.

There’s nothing more mind-numbing than a board meeting where the advance reading materials are lengthy Powerpoint presentations, than when the meeting itself is a series of team members standing up and going through the same slides, bullet by excruciating bullet—that attendees could read on their own.

When we separated the background and presentation materials, people were engaged by the Powerpoint—because it delivered fresh content. We started making the decks fun and engaging and colorful, as opposed to simple text and bullet slides. That was a step in the right direction, but the preparation consumed twice as much time for the management team, and we certainly didn’t get twice the value from it.

Now we send out a great set of comprehensive reading materials and reports ahead of the meeting, and then we have a completely Powerpoint-free meeting. No slides on the wall. This changes the paradigm away from a presentation—the whole concept of “management presenting to the board”—to an actual discussion. No checking email. No yawns. Nobody nodding off. Everyone—management and board—is highly engaged

As I mentioned earlier this summer, I’ve been working on a new startup the past few months with a group of long-time colleagues from Return Path.  Today, we are officially launching the new company, which is called Bolster.  The official press release is here.

Here’s the business concept.  Bolster is a talent marketplace, but not just any talent marketplace.  We are building a talent marketplace exclusively for what we call on-demand (or freelance) executives and board members.  We are being really picky about curating awesome senior talent.  And we are targeting the marketplace at the CEOs and HR leaders at venture- and PE-backed startups and scaleups.  We’re not a search firm.  We’re not trying to be Catalant or Upwork.  We’re not a job board. 

To keep both sides of the marketplace engaged with us, we are also building out suites of services for both sides – Members and Clients.  For Members, our services will help them manage their careers as independent consultants.  For Clients, our services will help them assess, benchmark and diversify their leadership teams and boards. 

We have a somewhat interesting founding story, which you can read on our website here.  But the key points are this.  I have 7 co-founders, with whom I have worked for a collective 88 years — Andrea Ponchione, Jack Sinclair, Shawn Nussbaum, Cathy Hawley, Ken Takahashi, Jen Goldman, and Nick Badgett.  We have three engineers with whom we’ve worked for several years who have been on board as contractors so far – Kayce Danna, Chris Paynes, and Chris Shealy.  We have four primary investors, who I’ve also known and worked closely with for a collective 77 years — High Alpha and Scott Dorsey (another veteran of the email marketing business), Silicon Valley Bank and Melody Dippold, Union Square Ventures and Fred Wilson, and Costanoa Ventures and Greg Sands.  Pretty much a Dream Team if there ever was one.

So how did our team and I get from Email Deliverability to Executive Talent Marketplace?  

It’s more straightforward than you’d think.  If you know me or Return Path, you know that our company was obsessed with culture, values, people, and leadership development.  You know that we created a cool workforce development nonprofit, Path Forward, to help moms who have taken a career break to care raise kids get back to work.  You know that I wrote a book for startup CEOs and have spent tons of time over the years mentoring and coaching CEOs.  Our team has a passion for helping develop the startup ecosystem, we have a passion for helping people improve and grow their careers and have a positive impact on others, and we have a passion for helping companies have a broad and diverse talent pipeline, especially at the leadership level.  Put all those things together and voila – you get Bolster!

There will be much more to come about Bolster and related topics in the weeks and months to come.  I’ll cross-post anything I write for the Bolster blog here on OnlyOnce, and maybe occasionally a post from someone else.  We have a few opening posts for Bolster that are probably running there today that I’ll post here over the next couple weeks.

If you’re interested in joining Bolster as an executive member or as a client, please go to www.bolster.com and sign up – the site is officially live as of today (although many aspects of the business are still in development, in beta, or manual).

Well, that’s a mouthful.  Let me break it down.

Ideas Matter Less Than Execution

Execution Matters Less Than Timing

Timing Matters Less Than Luck

There’s a persistent myth about entrepreneurs as heroes – the people with the brilliant ideas and Eureka moments that bring companies to life and create success.  I’ve never believed in that myth, or at least not in its universality, as I’ve always valued both ideation and execution in terms of business building.  But as I was thinking about that construct more the other day, it occurred to me that there’s actually a hierarchy of the two, and not just of the two, but of timing and luck as well.  The best businesses — the runaway successes — probably have all four of these things going, or at least three.  And in many cases, THE IDEA is the least important of the bunch.  Consider these examples:

Plaxo was launched a year or two before LinkedIn.

Friendster was launched a couple years before MySpace, which was launched before Facebook.  (You can go back even further and look at things like PlanetAll and Classmates.com).

Geocities predated blogging and Tumblr by more than a decade.

The Diamond Rio was launched three years before the first iPod.

Lycos, Excite, Infoseek, Altavista, Yahoo, and lots of other search engines and web crawlers were started well before Google.  Goto.com (Overture) did paid search before Google.

The ideas were all pretty similar.  In most cases, if not all, execution won out.  In the case of the iPod vs the Rio, it’s not that the world wasn’t ready for portable music – my Sony Walkman from the early 1980s is testament to that.  It’s that the combination of iTunes and the iPod, combined with Apple’s phenomenal design and packaging — all elements of execution — won the day.

The role that timing plays is also key.  Sometimes the world isn’t ready for a great technology yet, or it may be ready, but not for sustained growth and usage.  Friendster and MySpace vs. Facebook is the best example of this.  Facebook isn’t necessarily a better service, better marketed.  Friendster and MySpace were similarly viral in adoption at the beginning.  But the world was still in the Visionary or Early Adopter stage (in the language of Geoffrey Moore’s Crossing the Chasm).  By the time Facebook came around, the world was ready to mass adopt a social network.  Geocities, for example, was a big financial success at the time (Yahoo acquired the business for $5B – they “only” acquired Tumblr for $1B, give or take), but then it disappeared from the scene, where Tumblr seems much more durable.

The role of luck is harder to explain, or at least harder to separate from that of timing, and there’s a good argument that luck can be at the bottom of this particular chain, not the top (as in, luck is hard to separate from ideas).  Sometimes luck means avoiding bad luck, as in the story about Southwest Airlines — a great idea with promising early execution and good timing — narrowly avoiding a major crash during its first week of operations in 1967.  Sometimes luck means being in the right place at the right time, or making an accidental discovery, as in the case of the Princeton University professor, Edward Taylor, who discovered a powerful cancer treatment a bit accidentally while studying the pigments that produce the colors on the wings of butterflies for a completely unrelated purpose.

Don’t get me wrong.  Ideas are still important.  They are the spark that starts the fire.  And ideas can be partly created by the luck of being in the right place at the right time, so maybe this whole construct is more of a virtual circle than a hierarchy.  But entrepreneurs need to remember that a spark only gets you so far.  As the old saying goes, I’d rather be lucky than good!

Self-Discipline:  Broken Windows Applied to You

Just as my last post about New Shoes was touching a bit of a nerve around, as one friend put it, "mental housecleaning," my colleague Angela pointed me to a great post on a blog I've never seen before ("advice at the intersection of work and life" — I just subscribed), called How to Have More Self-Discipline.  Man, is that article targeted at me, especially about working out. 

I think the author is right — more discipline around the edges does impact happiness.  But it also impacts productivity.  Not just because working out gives you more energy.  Because having your act together in small ways makes you feel like you have your act together in all ways.  As the author notes (without this specific analogy), it's a little like the "broken windows" theory of policing.  You crack down on graffiti and broken windows, you stop more violent crime, in part because the same people commit small and large crimes, in part because you create a more orderly society in visible, if sometimes a bit small and symbolic, ways.

I agree that the best example in the "non work" world is fitness.  But what about the "work world"?  What's relevant around self-discipline for professionals?  Consider these examples:

– A clean inbox at the end of the day.  Yes, it's the David Allen theory of workplace productivity which I espouse, but it does actually work.  A clean mind is free to think, dream, solve problems.  The quickest path to keeping it clean is not having a pile of little things to deal with in front of it, taking up space

– Showing up on time.  It may sound dumb, but people who are chronically late to meetings are constantly behind.  The day is spent rushing around, cutting conversations short — in other words, unhappy and not as productive.  The discipline of ending meetings on time with enough buffer to travel or even just prepare for the next meeting so you can start it on time (and not waste the time of the other people in the meeting) is important.  Have too many meetings that you can't be at all of them on time?  Say no to some — or make them shorter to force efficiency.  There's nothing wrong with a 10-minute meeting

– Dressing for success.  We live in a casual world, especially in our industry.  I admit, once in a while I wear jeans or a Hawaiian shirt to work — even shorts if it's a particularly hot and humid day.  (And even in New York, not just in Boulder.)  But no matter what you wear, you can make sure you look neat and professional, not sloppy.  Skip the ripped jeans or faded/frayed/rock concert t-shirt.  Tuck in the shirt if it's that kind of shirt, and wear a belt.  The discipline of "dressing up" carries productivity a long way.  Want to really test this out at the edges?  Try wearing a suit or tie one day to work.  You feel different, and you sound different

– Doing your expenses.  Honestly, I've never seen an area where more smart and conscientious people fall apart than producing a simple expense report.  Come up with a system for it — do one every week, every trip on the plane home, every time you have an expense — and just take the 5 minutes and finish it off.  Sure, expenses are a pain, but they only really become a pain and a millstone around your brain when you let them sit for months because you "don't have time" to fill them out, then you get accounting all pissed off at you, and the project's size, complexity, and distance from the actual event all mount

– Follow rules of grammar and punctuation.  Writing, whether for external or internal consumption, is still writing.  I'm not sure when everyone became ee cummings and decided that it's ok to forget the basic rules of English grammar and punctuation.  Make sure your emails and even your IMs, at least when they're for business, follow the rules.  You look smarter when you do.  Maybe — maybe — with Twitter or SMS you can excuse some of this and go with abbreviations.  But I wouldn't normally consider a lot of those formal business communications

I could go on and on, but I think you get the idea.  A little self-discipline goes a long way at work (and in life)!

Feeling Less Like a Luddite:  Welcome, Lijit!

As I’ve written about a few times (here, here, and here), it’s easy to feel like a Luddite with the rapid pace of change of the web these days. Anyway, I’m feeling slightly less like one today with the addition of Lijit to my blog.

You’ll notice that I changed the search box from Google to Lijit on the right hand side of the page on OnlyOnce.  Lijit seems like it’s a better way to search a blog, and maybe other things as well.  Using Lijit, you can search not just the text of the blog itself (which is what Google allowed), but Lijit also goes out and searches a few other buckets of related content all in the same fell swoop.  So while it searches the blog, it also searches other sites that I run, other sites that are related to my site (e.g., blogs I subscribe to), other services where I might post content, like Flickr and Delicious and LinkedIn, and the open web.  Search results with four tabs — now that’s making good use of the web!

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.

Everything That is New is Old

With a full nod to my colleague Jack Sinclair for the title and concept here…we were having a little debate over email this morning about the value of web applications vs. Microsoft (perhaps inspired by Fred, Brad, and Andy’s comments lately around Microsoft vs. Apple).

Jack and his inner-CFO is looking for a less expensive way of running the business than having to buy full packages of Office for every employee to have many of them use 3% of the functionality.  He is also even more of a geek than I am.

I am concerned about being able to work effectively offline, which is something I do a lot.  So I worry about web applications as the basis for everything we do here.  We just launched a new internal web app last week for our 360 review process, and while it’s great, I couldn’t work on it on a plane recently as I’d wanted to.

Anyway, the net of the debate is that Jack pointed me to Google Gears, in beta for only a month now, as a way of enabling offline work on web applications.  It clearly has a way to go, and it’s unclear to me from a quick scan of what’s up on the web site whether or not the web app has to enable Gears or it’s purely user-driven, but in any case, it’s a great and very needed piece of functionality as we move towards a web-centric world.

But it reminded of me of an application that I used probably 10-12 years ago called WebWhacker (which still exists, now part of Blue Squirrel) that enables offline reading of static web pages and even knows how to go to different layers of depth in terms of following links.  I used to use it to download content sites before going on a plane.  And while I’m sure Google Gears will get it 1000x better and make it free and integrated, there’s our theme — Everything That is New is Old.

The iPhone?  Look at Fred’s picture of his decade old Newton (and marvel at how big it is).

Facebook?  Anyone remember TheSquare.com?

MySpace?  Geocities/Tripod.

LinkedIn?  GoodContacts.

Salesforce.com?  Siebel meets Goldmine/Act.

Google Spreadsheets?  Where to begin…Excel…Lotus 123…Quattro Pro…Visicalc/Supercalc.

RSS feeds?  Pointcast was the push precursor.

Or as Brad frequently says, derive your online business model (or at least explain it to investors) as the analog analog.  How does what you are trying to online compare to a similar process or problem/solution pair in the offline world?

There are, of course, lots of bold, new business ideas out there.  But many successful products in life aren’t version 1 or even version 3 — they’re a new and better adaptation of something that some other visionary has tried and failed at for whatever reason years before (technology not ready, market not ready, etc.).

Book Short:  A SPIN Selling Companion

At Return Path, we’re big believers in the SPIN Selling methodology popularized by Neil Rackham. It just makes sense. Spend more time listening than talking on a sales call, uncover your prospect’s true needs and get him or her to articulate the need for YOUR product. Though it doesn’t reference SPIN Selling, Why People Don’t Buy Things, by Kim Wallace and Harry Washburn is a nice companion read.

Rooted in psychology and cognitive science, Why People Don’t Buy Things presents a very practical sales methodology called Buying Path Selling. Understand how your prospect is making his or her buying decision and what kind of buyer he or she is, be more successful at uncovering needs and winning the business.

The book has two equally interesting themes, rich with examples, but the one I found to be easiest to remember was to vary your language (both body and verbal) with the buyer type. And the book illustrates three archetypes: The Commander, The Thinker, and The Visualizer. There are some incredibly insightful and powerful ways to recognize the buyer type you’re dealing with in the book.

But most of the cues the authors rely on are physical, and lots of sales are done via telephone. So I emailed the author to ask for his perspective on this wrinkle.  Kim wrote back the following (abridged):

Over the phone it is fairly easy to determine a prospect’s modality. I’ve developed a fun, conversational question which can be asked up front, “As you recall some of your most meaningful experiences at XYZ, what words, thoughts, feelings or visuals come to mind? Anything else?”

If you’re interested in letting your blog readers test their modalities, the link below will activate a quick 10 question quiz from our website that generates ones modality scores along how they compare with others. (It’s like Myers-Briggs applied to decision making.) http://www.wallacewashburn.com/quiz.shtml

In any case, if you are a sales, marketing, or client services professional (or even if you just play one on TV), Why People Don’t Buy Things is a quick, insightful read.  Thanks for the quick response, Kim!