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May 6 2010

New People Electrify the Organization

New People Electrify the Organization

 

We had a good year in 2009, but it was tough.  Whose wasn’t?  Sales were harder to come by, more existing customers left or asked for price relief than usual, and bills were hard to collect.  Worse than that, internally a lot of people were in a funk all year.  Someone on our team started calling it “corporate ennui.”  Even though our business was strong overall and we didn’t do any layoffs or salary cuts, I think people had a hard time looking around them, seeing friends and relatives losing their jobs en masse, and feeling happy and secure.  And as a company, we were doing well and growing the top line, but we froze a lot of new projects and were in a bit of a defensive posture all year.

 

What a difference a year makes.  This year, still not perfect, is going much better for us.  Business conditions are loosening up, and many of our clients have turned the corner.  Financially, we’re stronger than ever.  And most important, the mood in the company is great.  I think there are a bunch of reasons for that – we’re investing more, we’re doing a ton of new innovation, people have travel budgets again, and people see our clients and their own friends in better financial positions.

 

But by far, I think the most impactful change to the organizational mood we’re seeing is a direct result of one thing:  hiring.  We are adding a lot of new people this year – probably 60 over the course of the year on top of the 150 we had at the beginning of the year.  And my observation, no matter which office of ours I visit, is that the new people are electrifying the organization.  Part of that is that new people come in fresh and excited (perhaps particularly excited to have a new job in this environment).  Part of it is that new people are often pleasantly surprised by our culture and working environment.  Part of it is that new people come in and add capacity to the team, which enables everyone to work on more new things.  And part of it is that every new person that comes in needs mentoring by the old timers, which gives the existing staff reminders and extra reason to be psyched about what they’re doing, and what the company’s all about.

 

Whether it’s one of these things or all of them, I’m not sure I care.  I’m just happy the last 18 months are over.  The world is a brighter place, and so is Return Path.  And to all of our new people (recent and future), welcome…thanks for reinvigorating the organization!

 

Sep 17 2020

Bolster’s Founding Manifesto

(This post also appeared on Bolster.com and builds on last week’s post where I introduced my new startup, Bolster)

Welcome to Bolster, the on-demand executive talent marketplace. We are creating a platform that is the new way to scale an executive team and board.

verb: bolster; 3rd person present: bolsters; past tense: bolstered; past participle: bolstered; gerund or present participle: bolstering

support, boost, strengthen, fortify, solidify, reinforce, augment, reinvigorate, enhance, improve, invigorate, energize, spur, expand, galvanize, underpin, deepen, complement

We believe that startups and scaleups are not average companies. Their rapid growth means their appetite for talent constantly outstrips their budget — and that they can’t spend months searching for it. Their dynamic industries dictate that they keep pace with bigger and better funded competitors. Their leadership teams — the people and the roles — are always changing. Their CEOs spend a ton of time hiring and coaching their leaders and shaping the complexion and direction of the team. They stress out about big expensive new executive hires when sometimes they just need to level-up an existing manager or “try before they buy.” Their Boards frequently jump in to help, but those efforts can be a little ad hoc and inefficient.

We believe that experienced executives working as consultants is the wave of the future. The number of career executives who work flexibly and on-demand for a living is skyrocketing in recent years. People are more often “between things” and are interested in plugging into shorter-term engagements while continuing to look for their next full-time role. People are retiring younger, yet wanting to keep contributing. And even fully-employed execs like to advise companies and serve on Boards. Whether these people are career consultants or are looking for a “side hustle” or just to pay something forward to a future generation of leaders, they all have two common problems: finding work is time consuming and they’re often not good at or don’t like doing it; and managing their back office, everything from insurance to legal to tax to marketing, is a drain on time that could otherwise be spent with clients or family.

We believe that a new kind of talent marketplace is needed to meet the unique and complex requirements of both audiences — the freelance, or flexible, seasoned executive, and the startup or scaleup CEO who thinks holistically about his or her leadership team and carefully tends them like a garden. We are building a platform to make instant, tailored, vetted matches between talent and companies without the randomness of a job board and without the theater, long lead times, and cost, of a full service agency 

Service marketplaces like ours work best when they help their stakeholders solve other meaningful, related problems.In this case, we believe that the need for back office services will help executive consultants focus on more important things. And we believe that CEOs need lightweight and dynamic support in thinking through the composition and skills required of their executive teams both today and 6-18 months in the future.

That is the essence of the business we are building. A business to quickly match awesome companies with awesome freelance executives and to help both sides be better at what they do. We are here to make it easier for you to:

  • Bolster your executive team. For our Clients, our pledge to you is that we will quickly and cost-effectively fill the gaps in your leadership ranks (whether interim, fractional, advisory, board, or project-based) with trusted, curated talent, and that we will give you a platform to evaluate your overall leadership team and help you think through your future needs as your company evolves. Think of us as a shortcut to scaling your leadership team.
  • Bolster your board. The best boards are the ones with multiple independent directors who come from diverse backgrounds with diverse points of view. We also pledge to our Clients that we will find great matches to help fill out their boardrooms as their strategic advisory needs change over time.
  • Bolster your work. For our Members, our pledge to you is that we will find you the right kind of interesting clients and help you manage your back office so you can focus on your work (and all the other important things in your life!).
  • Bolster your portfolio. For our Portfolio Partners, VC and PE board members, our pledge to you is that we will make it easier for you and your firm to both drive successful on-demand executive placements for your portfolio company CEOs, and to manage and expand your firm’s network of flexible executive talent. 

We are an experienced team of entrepreneurs and operators who have scaled multiple businesses throughout our careers. All of us worked together as part of the leadership team at Return Path, a leading email technology company that we scaled from 0 to $100mm in revenue and 500 employees in 12 locations around the world while winning numerous Employer of Choice awards. All of us have independent experience scaling other businesses, small and large, public and private. All of us have experience being on-demand executives as well — whether interim, fractional, advisory, project-based, or board roles, we know the landscape of both our members and our clients. 

We’ve all dealt with the stress of having product-market fit and market opportunities but not being able to capitalize on those opportunities because we were missing key talent. And we’ve tried everything from executive search firms (expensive, time-consuming, and slow), to leveling up people (will they be able to grow into the role?), to leaning in to our board (hit or miss, inefficient). Heck, we’ve been desperate enough to follow up on the “my cousin’s boyfriend has an uncle, and he might know someone” lead.

We believe there is a better way for startups and scaleups to find executive talent. Along the way, I published a book about scaling startups called Startup CEO: A Field Guide to Scaling Up Your Business that has sold over 40,000 copies to CEOs around the world. And our whole team is working on a new book called Startup CXO: A Field Guide to Scaling Up Your Teams, which is coming out in early 2021. Our team has a maniacal focus on helping startup teams scale and flourish and on helping leaders develop into the best version of themselves. That’s what we’re all about. 
Plus, we have an amazing group of investors behind us who know how to grow businesses like ours and have incredible reach into the startup and scaleup world. More about that later. For now, we are excited to soft launch Bolster and begin unleashing the power of on-demand executive talent to our Clients. Thank you for being on this journey with us. If you’re interested in the somewhat unusual story of how the company was founded, it’s here.

Mar 22 2016

A New Path Forward

A New Path Forward

Welcome to the world, Path Forward, Inc.!

I’m thrilled to announce the launch today of Path Forward, a new non-profit with a goal of empowering millions of women to rejoin the workforce after taking time out for childcare. We are launching today with a Crowdrise campaign.   See more about that below.  And we launched with a bang, too – the organization is featured in this really amazing story on Fortune.

The concept started at Return Path two years ago, as I wrote about here and again here, when our CTO Andy Sautins came to me with a simple but powerful idea of creating a structured program of paid fellowships with training for women who want to reenter the workforce but find it difficult to do so because of rusty skills, lapsed networks, or societal bias. We expanded the program later that year with partner companies ReadyTalk, SendGrid, MWH Global, SpotX, and Moz, as I wrote about here.  The response from both participants and companies has been nothing short of amazing.

The day after I put up that last post about v2 of the program, a human resources leader at PayPal gave me a call and asked if we could help them structure a program for their engineering organization, too.  That’s when it struck me that the idea of midcareer internships as one means of providing an on-ramp to the paid workforce for people who’d been focused on caregiving could work for many companies, and also that for this program to work and scale up, it couldn’t be an “off the side of the desk” project for the People Team at Return Path.  So we decided to create a new company separate from Return Path to carry out this important work.  And we decided that with a practical, but social mission, it should be a non-profit, dedicated to creating and managing networks of companies offering opportunities to many more people.

To date, the program has served nearly 50 participants (mostly women, but a couple of stay-at-home dads, too!) and 7 companies in 6 cities around the world, producing an impressive 80% hire rate.  The participants who have been hired by us and our partner organizations have made impressive contributions to their companies’ businesses and cultures.  The companies have benefitted from their experience and passion.  That’s what I call product-market fit.  Now it’s time to officially launch the new organization, and scale it up!  Our BHAG (Big Hairy Audacious Goal, in the language of Jim Collins) is that within 10 years, we want to serve 10,000 companies and 1 million women and men.  We want to reduce the penalty that caregivers face when they take time away from paid work.  We want to transform lives by getting people who want to work, back to work in jobs that leverage all their many skills and talents.  We want to help companies tap into an incredibly important but overlooked part of the talent pool to grow their workforces.  We want to change the world.

We’ve been able to assemble a strong Board of Directors to lead this effort.  Joanne Wilson, often better known as Gotham Gal and the founder of the Women’s Entrepreneur Festival, is joining me as Board Co-chair. Joanne is a force to be reckoned with in championing women founders in tech.  Brad Feld joins our Board with great credentials as an early-stage investor, but more importantly he’s served for more than 10 years as Board Chair of the National Center for Women and Technology.  Media luminary and investor Cathie Black was most recently the President of Hearst Magazines having previously served as President and Publisher of USA Today.  Cathie has been the “first” woman many times and has broken her share of glass ceilings.  Rajiv Vinnakota is the Executive Vice President of the Youth & Engagement division at the Aspen Institute and prior to that was the co-founder and CEO of The SEED Foundation, a non-profit managing the nation’s first network of public, college-preparatory boarding schools for underserved children which he started and successfully scaled up for more than 17 years.  Cathy Hawley, our long-time VP of People at Return Path, gets (though often deflects) the lion’s share of the credit for conceiving and championing the original return to work program at Return Path.  It is, truly, an embarrassment of riches. We are so thrilled to have them all on board Path Forward’s Board.

On the staff side I’m also pleased to announce that one of my long-time executive lieutenants at Return Path, Tami Forman, has accepted the role of Executive Director of Path Forward. I can’t think of anyone better for this role. Tami is the consummate storyteller, which every good founder and Startup CEO needs to be! More importantly she has been living and breathing work/life integration for eight years since the birth of her daughter (followed by a son). She is absolutely passionate about the idea that women can have jobs and families and live big lives. And, more importantly, she’s dedicated to the idea that taking a “break” (she and I agree it’s not a break!) to care for a loved one shouldn’t sideline anyone’s career dreams.

I can’t wait to see how far this idea can go. I truly believe this program can have a measurable, positive impact on thousands of companies across the country and the world.

Please join me and Tami and our talented Board on this journey.  Help us change the world.  There are three ways to participate:

(Please note – we haven’t yet received word of our non-profit status yet from the IRS, though we expect it in the next couple of months.  As such, any donation now is not tax deductible until after the certification comes through.  While there’s some risk that we don’t gain non-profit status…we don’t think the risk is large.)

Feb 16 2025

Why Executive Searches are So Slow, and What You Can Do About That as a Candidate

It’s been a big break between posts – as many of you probably know, I moved to Board Chair and left the CEO role at Bolster last summer (it’s now in the very capable hands of my friend and co-founder Cathy Hawley), and I’m now CEO of a super cool AI company called Acrolinx.  So yes, that means I went through a job search – and I found my ultimate job as a result of an inbound cold email from a headhunter!  The rich irony in that as someone who founded an executive search platform is not lost on me.

So when a good friend of mine who is also between CEO gigs and looking at several opportunities asked me the other day “why is this process so slow, and what can I do about it?” I riffed with him on the theme for a bit and thought I’d share my thinking here. 

Why Executive Searches are Slow

My top three reasons on this are pretty varied – there’s no specific theme.

  1. Boards aren’t efficient hiring managers. When hiring a CEO, even the best intentioned boards can be slow to move. Frequently they operate with a search committee, and even if there’s a lead director on the search committee or even no actual search committee, by design they need to operate with a high degree of consensus. Organizing five calendars to meet with or debrief on a candidate can take weeks. And a single loud voice saying “no” or “not sure” can paralyze a board. All this is true for a CEO search but can also be true when a less experienced CEO is trying to hire a CXO and needs a lot of Board involvement in the process. At Bolster, we’ve worked on mitigating this by getting the key decision-makers aligned on search criteria at the beginning of the search, prepping interviewers, and creating a scorecard for each candidate that is visible to all decision-makers, but sometimes that doesn’t matter.
  2. Boards and CEOs often don’t know what they want.  Whether a company is hiring a role for the first time or replacing an executive, they often get to a generic job spec but don’t actually know what they’re looking for. Not all CEOs are created equal. Not all CROs have the same core competencies. At Bolster, we developed a description of role archetypes for each C-suite or Head-or role that helps with this process (eg for a CFO, do you want an Accounting type, a Finance/Ops type, or a Deal type?). But even if a Board or hiring CEO has this level of detail down, it can still be a murky picture, trapped between the company’s past successes and failures on one side and its future needs on the other. Processes move slowly because it take a while for the picture to become less murky – circumstances around the company evolve, or people see how the company operates without this role as others pick up the slack, and therefore the needs of the role shift or come into focus. Sometimes meeting a series of candidates is the only thing that can help drive this focus, and per the first bullet above, this just takes time. If a company has a strong search partner, that may speed things up via quick presentation of calibration candidates.
  3. There’s no precipitating crisis.  Most companies and departments, most of the time, are not in crisis. A lot of companies can operate without a given executive, even a CEO, for quite some time. Some things done (don’t) get done. Other people rise to the occasion and pick up the most important items. Or the company has hired an interim or fractional executive as a stop gap measure. Without a specific and clear sense of urgency, searches often don’t have a driving force. Sometimes there’s a precipitating crisis like a system outage or massive customer churn or the company running out of cash that can provide that driving force, but that is not the norm.

What Can You as a Candidate Do About It?

The answer is probably “not much.”  But if my own search was any indicator, I’d give you the same advice I give people internally at my company when they ask me how to get a promotion.  My answer is “start doing the job today, don’t wait to actually get the job.”  Obviously a candidate for a CEO role or any other executive role can’t actually start doing the job as an existing employee could start taking on additional pieces of work.  But there are a lot of things you can do to “act as it” and get the hiring Board or hiring CEO’s attention.  For example:

  • As a CEO candidate, be a management consultant.  Work on designing a strategy for the company you want to work for.  Do a tremendous amount of homework you can do from the outside – read analyst reports, get stealth demos, do market and customer interviews.  You don’t have to explain what you’re up to in terms of identifying the company.  You can say you’re interviewing for a CEO role in the sector.  Or even that you’re doing market research.  But proactively sending the hiring board a strategy deck and asking for the next meeting is a good way of differentiating yourself as a candidate and potentially accelerating a process.
  • As a CRO candidate, go try to sell the company’s product.  Do it to a couple “friendlies” (e.g, people who are friends of yours, not active customers or prospects of the company you’re interviewing with) so you don’t tread on the actual business.  But create your own deck.  Get meetings.  Write up your experience.  Sending the CEO or board an email that says “Hey, I have a prospect already in the final stage of the funnel for you, can we work together to close her?” is a sure way to differentiate yourself as a candidate and potentially accelerate a process.

There may be a macro answer here as well.  The market is still choppy, and boards and CEOs are more conservative in most sectors and subsectors than they are in go-go times.  So that may be slowing things down in general and may even make it harder to act as-if.  But that doesn’t mean you can’t try.

Nov 17 2006

The Good, The Board, and The Ugly, Part III

The Good, The Board, and The Ugly, Part III

To recap other postings in this series:  my original, Brad Feld’s, Fred Wilson’s first, Fred’s second, Tom Evslin’s, and my lighter-note follow-up.

So speaking of lighter-note takes on this topic, Lary Lazard, Tom Evslin’s fictional CEO who ran Hackoff.com, now has his own tips for effective board management.  You have to read them yourself here, but I think my favorite one is #3, which starts off:

Never number the pages of what you are presenting.  Lots of time can be used constructively figuring out what page everybody is on.

Enjoy.

Oct 5 2005

What a View, Part II

What a View, Part II

In Part I, I talked about how Return Path’s 360 reviews have become a central part of our company’s human capital strategy over the past five years.  While most staff members’ reviews have been done for weeks or months now, I just finished up the final portion of my own review, which I think is worth sharing.

I always include my Board in my own 360.  My process is as follows:

1. I send the Board all the raw (and summarized) data from the staff reviews of me, both quantitative and qualitative.

2. I send the Board a list of questions to think about in terms of their view of my performance (see below).

3. I have a third party moderator, in my case a great OD consultant/executive coach that I work with, Marc Maltz from Triad Consulting, meet with the Board (without me present) for 1-2 hours to moderate a discussion of these questions.

4. The moderator summarizes the conversation and helps me marry the feedback from the Board with the feedback from my team.

The questions I ask them to consider are different from the question my staff answers about me, because the relationship and perspective are different.  For each question, I also summarize what their collective response was the prior year to refresh their memory.

1. Staff management/leadership:  How effective am I at building and maintaining a strong, focused, cohesive team?  Do I have the right people in the right roles at the senior staff level?

2. Resource allocation:  Do I do a good enough job balancing among competing priorities internally?  Are costs adequately managed?

3. Strategy:  Did you feel like last year’s strategy session was thorough enough?  Do you think we’re on target with what we’re doing?  Am I doing a good enough job managing to it while being nimble enough to respond to the market?

4. Execution:  How do I and the team execute vs. plan?  What do you think I could be doing to make sure the organization executes better?

5. Board management/investor relations:  Do you think our board is effective and engaged?  Have I played enough of a role in leading the group?  Do you as a director feel like you’re contributing all you can contribute?  Do I strike the right balance between asking and telling?  Are communications clear enough and regular enough?

6. Please comment on how I have handled some of the major issues in the past 12 months (with a listing of critical incidents).

The feedback I got is incredibly valuable, and once I marry it with the feedback I got from my staff, I will have my own killer development plan for the next 12-24 months.

Aug 26 2010

Style, or Substance?

Style, or Substance?

I had an interesting conversation the other day with a friend who sits on a couple of Boards, as do I (besides Return Path’s).  We ended up in a conversation about some challenges one of his Boards is having with their CEO, and the question to some extent boiled down to this:  a Board is responsible for hiring/firing the CEO and for being the guardians of shareholder value, but what does a Board do when it doesn’t like the CEO’s style?

There are lots of different kinds of CEOs and corporate cultures.  Some are command-and-control, others are more open, flat, and transparent.  I like to think I and Return Path are the latter, and of course my bias is that that kind of culture leads to a more successful company.  But I’ve worked in environments that are the former, and, while less fun and more stressful, they can also produce very successful outcomes for shareholders and for employees as well.

So what do you do as a Board member if you don’t like the way a CEO operates, even if the company is doing well?  I find myself very conflicted on the topic, and I’m glad I’ve never had to deal with it myself as an outside Board member.  I certainly wouldn’t want to work in an organization again that had what I consider to be a negative, pace-setting environment, but is it the Board’s role to shape the culture of a company?  Here are some specific questions, which probably fall on a spectrum:

Is it grounds for removal if you think the company could be doing better with a different style leader at the helm?  Probably not.

Is it fair to expect a leader to change his or her style just because the Board doesn’t like it?  Less certain, but also probably not.

Is it fair to give a warning or threaten removal if the CEO’s style begins to impact performance, say, by driving out key employees or stifling innovation?  Probably.

Is it fair to give feedback and coaching?  Absolutely.

This is one of those very situation-specific topics, but probably a good one for others to weigh in on.  I do come back to the question of whether it is part of a Board’s role to shape the culture of a company.  Is that just style…or is it substance?

Jul 1 2014

Book Short: Culture is King

Book Short:  Culture is King

Joy, Inc.:  How We Built a Workplace People Love, by Richard Sheridan, CEO of Menlo Innovations, was a really good read. Like Remote  which I reviewed a few weeks ago, Joy, Inc. is ostensibly a book about one thing — culture — but is also full of good general advice for CEOs and senior managers.

Also like Remote, the book was written by the founder and CEO of a relatively small firm that is predominately software engineers, so there are some limitations to its specific lessons unless you adapt them to your own environment. Unlike Remote, though, it’s neither preachy nor ranty, so it’s a more pleasant read.  And I suppose fitting of its title, a more joyful read as well. (Interestingly on this comparison, Sheridan has a simple and elegant argument against working remotely in the middle of the book around innovation and collaboration.)

Some of the people-related practices at Sheridan’s company are fascinating and great to read about. In particular, the way the company interviews candidates for development roles is really interesting — more of an audition than an interview, with candidates actually writing code with a development partner, the way the company writes code. Different teams at Return Path interview in different ways, including me for both the exec team and the Board, but one thing I know is that when an interview includes something that is audition-like, the result is much stronger. There are half a dozen more rich examples in the book.

Some of the other quotable lines or concepts in the book include:

  • the linkage between scalability with human sustainability (you can’t grow by brute force, you can only grow when people are rested and ready to bring their brain to work)
  • “Showcasing your work is accountability in action” (for a million reasons, starting with pride and ending with pride)
  • “Trust, accountability, and results — these get you to joy” (whether or not you are a Myers-Briggs J, people do get a bit of a rush out of a job well done)
  • “…the fun and frivolity of our whimsically irreverent workplace…” (who doesn’t want to work for THAT company?)
  • “When even your vendors want to align with your culture, you know you’re on the right path” (how you treat people is how you treat PEOPLE, not just clients, not just colleagues)
  • “One of the key elements of a joyful culture is having team members who trust one another enough to argue” (if you and I agree on everything, one of us is not needed)
  • “The reward is in the attempt” (do you encourage people to fail fast often enough?)
  • “Good problems are good problems for the first five minutes. Then they just feel like regular problems until you solve them” (Amen, Brother Sheridan)

The benefits of a joyful culture (at Return Path, we call it a People-First culture) have long been clear to me. As Sheridan says, we try to “create a culture where people want to come to work every day.” Cultures like ours look soft and squishy from the outside, or to people who have grown up in tough, more traditional corporate environments. And to be fair, the challenge with a culture like ours is keeping the right balance of freedom and flexibility on one side and high performance and accountability on the other. But the reality is that most companies struggle with most of the same issues — the new hire that isn’t working out or the long-time employee who isn’t cutting it any more, the critical path project that doesn’t get done on time, the missed quarter or lost client.  As Sheridan notes though, one key benefit of working at a joyful company is that problems get surfaced earlier when they are smaller…and they get solved collaboratively, which produces better results. Another key benefit, of course, is that if you’re going to have the same problems as everyone else, you might as well have fun while you’re dealing with them.

If you don’t love where you work and wish you did, read Joy, Inc. If you love where you work but see your company’s faults and want to improve them, read Joy, Inc. If you are not in either of the above camps, go find another job!

Apr 29 2008

Executive and Closed Sessions

Executive and Closed Sessions

Brad has a good post up about what he calls “closed sessions” in Board meetings — time at the end of the meeting reserved for a conversation with Board members ONLY, no other observers or non-Board management.  While we differ in terminology, I agree completely with the sentiment and with his logic.

We call the part of the meeting that Brad describes the Executive Session.  We’ve always done them.  And the Board and I find it incredibly useful, and a good practice, even if there are no contentious or puzzling issues during a meeting.  Not that our Board holds back much, but the Executive Session is a good time for us to connect 100% freely about management issues as well as elements of business strategy and performance that might be better hashed out without others present.

We also have an additional part of the meeting at the very end which we call the Closed Session.  This part of the meeting has NO MANAGEMENT in it, even me, although I’m Chairman of the Board.  This time allows the other directors an even greater degree of freedom to discuss the business or my performance without worrying about saying something in front of me — and without hearing my opinion.

Both sessions are incredibly valuable parts of high functioning Boards.

Oct 7 2011

Must-Read New Blog

Must-Read New Blog

I’ve talked about Why I Love My Board a few times in the past.  I was reminded at my quarterly Board meeting and dinner this week that it’s a great and unusually strong group, and we’re lucky to have them.  Fred and Brad have both been prolific bloggers for years,and I know many of you follow their blogs closely.  Think of that as getting a taste of the input and wisdom you’d get by having them on your Board.

In a very exciting development, one of my independent directors, Scott Weiss, has now started blogging on the Andreessen-Horowitz platform.  Scott is probably our most outspoken and colorful director (and that’s saying something).  Scott just joined Andreessen-Horowitz as a partner in their fund, so he now a VC, but his experience as an operator both at Hotmail in Internet 1.0 and then at Ironport have been incredibly valuable for me as an entrepreneur, and I expect most of his posts to focus on the entrepreneur’s perspective.

Two of Scott’s first three posts, Looking Bigger and Ridiculously Transparent, are perfect examples of the value I’ve gotten out of my six year relationship with Scott as a Board member.  If you want a taste of what it would be like to have him in your corner…subscribe to his blog!

Dec 22 2007

Book Short: a Corporate Team of Rivals

Book Short:  a Corporate Team of Rivals

One of the many things I have come to love about the Christmas holiday every year is that I get to go running in Washington DC.  Running the Monuments is one of the best runs in America.  Today, at my mother-in-law’s suggestion, I stopped i8n at the Lincoln Memorial mid-run and read his second inaugural address again (along with the Gettysburg Address).  I had just last week finished Doris Kearns Goodwin’s Team of Rivals:  The Political Genius of Abraham Lincoln, and while I wasn’t going to blog about it as it’s not a business book, it’s certainly a book about leadership from which any senior executive or CEO can derive lessons.

Derided by his political opponents as a “second-rate Illinois lawyer,” Lincoln, who arrived somewhat rapidly and unexpectedly on the national scene at a time of supreme crisis, obviously more than rose to the occasion and not only saved the nation and freed the slaves but also became one of the greatest political leaders of all time.  He clearly had his faults — probably at the top of the list not firing people soon enough like many of his incompetent Union Army generals — but the theme of the book is that he had as one of his greatest strengths the ability to co-opt most of his political rivals and get them to join his cabinet, effectively neutering them politically as well as showing a unity government to the people.

This stands in subtle but important contrast to George Washington, who filled his cabinet with men who were rivals to each other (Hamilton, Jefferson) but who never overtly challenged Washington himself.

Does that Team of Rivals concept — in either the Lincoln form or the Washington form — have a place in your business?  I’d say rarely in the Lincoln sense and more often in the Washington sense.

Lincoln, in order to be effective, didn’t have much of a choice.  Needing regional and philosophical representation on his cabinet at a time of national crisis, bringing Seward, Chase, and Bates on board was a smart move, however much a pain in the ass Chase ended up being.  There certainly could be times when corporate leadership calls for a representative executive team or even Board, for example in a massive merger with uncertain integration or in a scary turnaround.  But other than extreme circumstances like that, the Lincoln model is probably a recipe for weak, undermined leadership and heartache for the boss.

The Washington model is different and can be quite effective if managed closely.  One could argue that Washington didn’t manage the seething Hamilton and frothy Jefferson closely enough, but the reality is that the debates between the two of them in the founding days of our government, when well moderated by Washington, forged better national unity and just plain better results than had Washington had a cabinet made up of like-minded individuals.  As a CEO, I love hearing divergent opinion on my executive team.  That kind of discussion is challenging to manage — at least in our case we don’t have people at each other’s throats — but as long as you view your job as NOT to create compromises to appease all factions but instead to have the luxury of hearing multiple well articulated points of view as inputs to a decision you have to make, then you and your company end up with a far, far better result.