As I mentioned the other day, the second edition of Startup CEO is out.  This post is a teaser for the content in one of the new chapters in this edition on Authentic Leadership.

As I mentioned last week, the book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events. Two of those principles, which are timeless and transcend turmoil, uncertainty, time and place, are creating space to think and reflect and being intentional in your actions. In a world in which CEOs are increasingly called upon to deal with more than traditional business (pricing, strategy, go-to market approaches, team building, etc.) it’s imperative to approach and solve challenging situations from a foundation that doesn’t waver. 

At Return Path our values were the foundation that provided a lens through which we made every decision. Well, not every decision, only the good ones. When we strayed from our core values, that got us into trouble. The other principle, outlined in Chapter 1 of the Second Edition, is leading an organization authentically.

Let me provide a couple concrete examples of what I mean by “Authentic Leadership” since the term can be interpreted many ways.

One example is to avoid what I call the “Say-Do” gap.  This is obviously a very different thread than talking about how the company relates to the outside world and current events.  But in some ways, it’s even more important.  A leader can’t truly be trusted and followed by their team without being very cognizant of, and hopefully avoiding close to 100%, any gap between the things they say or policies they create, and the things they do.  There is no faster way to generate muscle-pulling eyerolls on your team than to create a policy or a value and promptly not follow it. 

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

What does that say about the CEO? How engaged are employees likely to be, how much effort are they willing to devote to the company if there are special rules for the executives? You can make any rule you want — as you probably know if you have read a bunch of my posts or my book over the years, I’m a proponent of rule-light environments — but you can’t make rules for everyone else that you aren’t willing to follow yourself unless you own the whole company and don’t care what anyone thinks about you or says about you behind your back.

Beyond avoiding the Say-Do Gap, this new chapter of the book on Authentic Leadership also talks about how CEOs respond to current events in today’s increasingly politicized and polarized world.  This has always felt to me like a losing proposition for most CEOs, which I talk about quite a bit in the book.  When the world is polarized, whatever you do as CEO, whatever position you take on things, is bound to upset, alienate, or infuriate some nontrivial percentage of your workforce.  I even give some examples in the book of how I focused on using the company’s best interests and the company’s values as guideposts for reacting (or not reacting) to politically divisive or charged issues like guns or “religious liberty” laws.  I say this noting that there are some people who *believe* that their side of an issue like this is right, and the other side is wrong, but the issues have some element of nuance to them.

Today’s world feels a bit different, and I’m not sure what I would be doing if I was leading a known, scaled enterprise at this stage in the game.  The largely peaceful protests around all aspects of racial injustice in America in the wake of the murder of George Floyd — and the brutality and senselessness of that murder itself — have caused a tidal wave of dialog reaching all corners of the country and the world.  The root of this issue doesn’t feel to me like one that has a lot of nuance or a second side to the argument.  After all, what reasonable person is out there arguing that George Floyd’s death was called for, or even that black Americans don’t have a deep-seeded and widespread reasonable claim to inequality…even if their view of what to do about it differs?

I *think* what I would be doing in a broader leadership role today is figuring out what my organization could be doing to help reduce or eliminate structural racial inequality where we could based on our business, as opposed to driving my organization to take a specific political stand. I know for sure that I wouldn’t solicit feedback from a select group of people only, but I would create a space where voices from across the organization (and stakeholders outside of it as well) could be heard. That’s not a solution, but a start, and in challenging times making a little bit of headway can lead to a cascading effect. It can, if you keep the momentum.

And, in line with “authentic leadership,” it’s okay to admit that you don’t have the answers, that you might not even know the questions to ask. But doing nothing, or operating in a “business as usual” way won’t make your company stronger, won’t open up new opportunities, won’t generate new ideas, and won’t sit well with your employees, who are very much thinking about these issues. 

So, in today’s challenging times I would follow my own advice, be thoughtful and reflective, and intentional in searching for common solutions.  I’d try to avoid “mob mentality” pressure — but I would also be listening carefully to my stakeholders and to my own conscience.

In the coming weeks, I’ll write posts that get into some of the other topics I cover in the book, but none of them will be as good as reading the full thing!

It’s election season, the GOP convention is literally in my backyard, and while this is not a political blog, I can’t help myself. As we as Americans grapple with the question of who we want to be our next leader (or at least those people who live in the 11 annointed swing states do), I have had a lot of thoughts lately about the question of what makes a good leader, and what the differences are between successful leadership in politics and successful leadership in business.

James O’Toole’s article on President Bush on page 31 of the September issue of Fast Company (no link available yet) brings up a really interesting point in comparing Bush to former president Ronald Reagan. He asserts that “what made Reagan effective and respected was that his actions followed consistently from a positive worldview.” (I’d also argue that the positive worldview as a starting point had something to do with it, but that’s beside the point.) He goes on to say that Bush has an “implementation problem” in that he “has vacillated between contradictory approaches to leadership: realism and idealism.” His central thesis is stated very clearly that

“Realists and idealists can both be effective leaders. But one cannot be both at once…The leadership lesson for GW – and for any leader – is simple: Followers don’t much care if leaders are realists or idealists, but they distrust inconsistency.”

This may or may not be true in the political arena, but I know it’s not true in business. Jim Collins’ watershed books Built to Last and Good to Great — both must reads! — describe the ideal CEO as someone who can simultaneously be optimistic and idealistic about the future of the company while simultaneously recognizing and dealing with the realities of the short-term situation. Ironically for this posting, Collins calls this the Stockdale paradox, after retired Admiral James Stockdale, a military leader and erstwhile vice presidential candidate of Ross Perot in the 1992 election.

As CEO, I have to constantly be selling the vision of the company — what we’re trying to become and how we’re going to get there — in broad strokes to my investors, board, management team, employees, and even customers. It’s that vision that keeps the whole machine running and keeps everyone focused and excited and working hard towards our long-term goals. But I have to be equally vigilant about the mundane realities of the current quarter, making our numbers, containing costs, and running the machine. If I did either one without the other, I think the whole system would break down.

Is Bush’s problem, as O’Toole asserts, that he articulated two different types of reasons for the war in Iraq — one rooted in Realism (WMD) and one rooted in Idealism (freedom and democracy)? Same goes for his states reasons for the tax cut — Realism on the one hand (to stimulate the economy) and Idealism on the other hand (shrink government). I agree that the Bush Administration has occasional implementation problems and doesn’t have nearly the “following” that Reagan and other more successful leaders in the past have, but I don’t think they’re caused by combining Realism and Idealism in the President’s leadership style. I think the leader of the free world has to do both well, each at its appropriate time, in order to be effective at his job.

Next up in this series: Admitting Mistakes.

Half the Benefit is in the Preparation

This past week, we had what has become an annual tradition for us – a two-day Board meeting that’s Board and senior management (usually offsite, not this year to keep costs down) and geared to recapping the prior year and planning out 2009 together.  Since we are now two companies, we did two of them back-to-back, one for Authentic Response and the other for Return Path.

It’s a little exhausting to do these meetings, and it’s 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 off the high dive for another year.

The most exhausting part is probably the preparation for the meetings.  We probably send out over 400 pages of material in advance – binders, tabs, the works.  It’s the only eco-unfriendly Board packet of the year.  It feels like the old days in management consulting.  It takes days of intense preparation — meetings, spreadsheets, powerpoints, occasionally even some soul searching — to get the books right.  And then, once those are out (the week before the meeting), we spend almost as much time getting the presentations down for the actual meeting, since presenting 400 pages of material that people have already read is completely useless.

By the end of the meetings, we’re in good shape for the next year.  But before the meetings have even started, we’ve gotten a huge percentage of the benefit out of the process.  Pulling materials together is one thing, but figuring out how to craft the overall story (then each piece of it in 10-15 minutes or less) for a semi-external audience is something entirely different.  That’s where the rubber meets the road and where good executives are able to step back; remember what the core drivers and critical success factors are; separate the laundry list of tactics from the kernel that includes strategy, development of competitive advantage, and value creation; and then articulate it quickly, crisply, and convincingly. 

I’m incredibly proud of how both management teams drove the process this year – and I’m charged up for a great 2009 (economy be damned!).

Book Short: The Anti-Level-5 Leader

The Five Temptations of a CEO, another short leadership fable in a series by Patrick Lencioni, wasn’t as meaningful to me as the last one I read, The Four Obsessions of an Extraordinary Executive (post, link), but it wasn’t bad and was also a quick read.

The book to me was the 30 minute version of all the Level-5 Leadership stuff that Collins wrote about in Good to Great and Built to Last. All that said, it was a good quick read and a reminder of what not to do. The temptations are things that most CEOs I’ve ever known (present company very much included) have at least succumbed to at one point or another in their career. That said, you as a CEO should quit or be fired if you have them in earnest, so hopefully if you do have them, you recognize it and have them in diminishing quantities with experience, and hopefully not all at once:

– The temptation to be concerned about his or her image above company results

– The temptation to want to be popular with his or her direct reports above holding them accountable for results

– The temptation to ensure that decisions are correct, even if that means not making a decision on limited information when one is needed

– The temptation to find harmony on one’s staff rather than have productive conflict, discussion, and debate

– The temptation to avoid vulnerability and trust in one’s staff

I’m still going to read the others in Lencioni’s series as well. They may not be the best business books ever written, but they’re solid B/B+s, and they’re short and simple, which few business books are and all should be!

Political versus Corporate Leadership, Part II: Admitting Mistakes

The press conference this past spring where President Bush embarrassingly refused to admit that he had ever made any big mistakes, other than to reiterate his gaffe at trading Sammy Sosa when he owned the Texas Rangers, brings up another issue in this series: is it good for leaders, both political and corporate, to admit mistakes?

On the corporate side, I think the ability to admit a mistake is a must. Again, I’ll refer back to Jim Collins’ books Good to Great and Built to Last, both of which talk about humility and the ability to admit mistakes as a critical component of emotional intelligence, the cornerstone of solid leadership. And in another great work on corporate leadership, The Fifth Discipline, writer Peter Senge talks about “learning systems” and the “learning organization” as far superior companies. My experience echoes this. Publicly admitting a mistake, along with a careful distillation of lessons learned, can go a long way inside a company to strengthening the bond between leader and team, regardless of the size of the company.

But in politics, the stakes are higher and weirder — and the organization is a nation, not a company. Publicly admitting a single mistake can be a leader’s downfall. It’s too easy these days for political opponents to seize on a mistake as a “flip flop” and turn a candidate’s own admission into a highly-charge negative ad.

There was a fantastic op-ed in The Wall Street Journal back on April 15 on this topic, which unfortunately doesn’t have an available link at the moment, entitled “Bush Enters a Political Quandary As He Faces Calls for an Apology.” I’ll try to both quote from and summarize the article here since it’s central to this topic:

“For a politician, is an apology a sign of weakness or strength? That is the debate now swirling around President Bush after a prime-time news conference in which he refused reporters’ invitations to acknowledge any specific mistakes in handling the issue of terrorism or offer an apology to Sept. 11 victims’ families. Mr. Bush deflected the invitation, saying, ‘Here’s what I feel about that: The person responsible for the attacks was Osama bin Laden.’ Mr. Bush’s quandary is a time-honored struggle for politicians. While some have found a public apology helps them out of a tough spot, others discovered it can fuel more criticism. So far, there isn’t a definitive answer.”

The article goes on to say that while Harry Truman’s “the buck stops here” mentality was de rigeur in the Beltway for a while (through Kennedy’s Bay of Pigs fiasco and Reagan’s poor handling of Beirut), nowadays, apologies are a dreaded last resort. The reason? The rise of partisanship and the use of ethics and congressional or special counsel investigations used to humiliate or defeat political opponents by raising the spectre of corruption. The examples? Gingrich’s struggles in 1996 over his book; Clinton’s ridiculous linguistics machinations (“it depends what the definition of ‘is’ is”) around the Lewinsky scandal; and Lott’s downfall over segregationist comments.

The piece wraps up by saying that “Mr. Bush was backed into the apology quandary by one of his administration’s toughest critics, former White House terrorism expert Richard Clarke…Since then, White House officials have been pressured to do likewise [apologize to victims’ families about the government’s failings on 9/11] — or explain why they won’t…[but] aides are convinced that admitting error would only embolden Mr. Bush’s critics in the Democratic Party and the news media.”

So the question is: would Bush be better off by saying “Sorry, folks, we thought there were WMD in Iraq, but it turns out we were wrong. And we miscalculated how difficult it would be to win the war, how many troops it would take, and how many lives would be lost. I still feel like it was right for us to go to war there for the following four reasons…”?

I’m not sure about that. He’d certainly be more intellectually honest, and a number of people in intellectual circles would feel better about him as a leader, but my guess is that he thinks it would cost him the election in today’s environment. My conclusion is that today’s system is discouraging politicians from admitting mistakes, and that it will take an exceptionally courageous leader (neither Bush nor Kerry as far as I can tell) to do so.

In the end, while humility appeals to many people in a leader, it’s not for everyone. Fortunately for us, CEOs don’t have to run for office and most CEOs don’t have to face some the same level of public, personally competitive, and media scrutiny that politicians do. Now that’s an interesting conclusion that I didn’t intend at the beginning of the post — being a good political leader and being a good politician are sometimes deeply at odds with each other.

Next up in the series: Not sure! Any ideas? Please comment on the blog site or by emailing me.

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.

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.

How to Wow Your Employees

Here at Return Path we like to promote a culture of WOW and a culture of hospitality.  Some of you may be asking, Why Wow your employees?   The answer is, there is nothing more inspirational than showing an employee that you care about him or her as an individual.  The impact a WOW has is tremendous.  Being a manger is like being in a fishbowl.  Everything you do is scrutinized by your team.  You lead by example whether you want to or not and showing your own vulnerability/humanity has an amazing bonding effect.

Why do you want to foster Wow moments with your team?  High performing teams have a lot of Wow going on.  If all members of a team see Wow regularly, they are all inspired to do more sooner and better.

Here are 15 ways to Wow your employees

1. Take them or her to lunch/breakfast/drinks/dinner quarterly individually, one nice one per year
2. Learn their hobbies and special interests; when you have a spiff to give, give one that is in line with these
3. Remember the names of their spouse/significant other/kids/pets
4. Share your development plan with them and ask for input against it at least quarterly
5. Respond to every email from your staff by the end of the day; sooner if you are on the TO line
6. Ask them what they think of a piece of work you’re doing
7. Ask them what they think of the direction the company is going, or a specific project
8. Periodically take something off each one’s plate, even if it’s clearly theirs to do
9. Periodically tell them to take a day off to recharge, ideally around something important in their lives
10. End every meaningful interaction by asking how they are doing and feeling about work
11. End every interaction by asking what you can be doing to help them do a better job and advance their career
12. Read all job openings and highlight ones that match their interests for future positions
13. Read the weekly award list and call out those FROM and TO your team in staff meetings
14. Send a handwritten note to their home when you have a moment of appreciation for them
15. (If your employee has a team he/she manages) Ask for input before every skip-level interaction and summarize each one after the fact in an email or in person

I try to have Wow moments regularly with people at all levels in the organization.  Here’s one that sticks with me.  At the Colorado summer party several years ago, I went up to someone who was a few layers down in the organization and said hi to her husband and dog by name.  I had met them before, and I work at remembering these things.  The husband was blown away – I hadn’t talked to him in probably two years.  In front of the employee, he gushed – “this is exactly why my wife loves working here – we are totally committed to being part of the RP family.”

There are as many ways to be a great manager and WOW your employees as there are stars in the sky…hopefully these ideas give you a framework to make these your own!

I wrote a colorfully-named post years ago called Onboarding vs. Waterboarding, which detailed out some of the general principles around onboarding new employees that our companies have used over the years. A few weeks back, one of our clients and fellow CEOs of a Series C Ed:Tech company asked me for tips on onboarding senior executives, and some of what I said varied from or built on that earlier post.

Here are a few of the themes we riffed on:

1. Treat the new hire onboarding like you would a merger integration. Why? Well, because adding a new exec to your company is kind of like…a merger integration. Make a long checklist. Assign each item an owner and participating parties. Have a weekly meeting with all key stakeholders specifically to review the onboarding plan. In other words, don’t just leave it up to you, the new exec, and a Day 1 overview meeting with “business as usual” check-ins. Make it its own thing.
   
2. Take great care to communicate expectations and changes internally when the new exec starts. Any new exec, but especially one in a newly-created or upgraded role, will carry a new role description which by definition changes expectations and responsibilities both of the new exec’s role and of other execs’ roles (and possibly your own role or Level-2 team members’ roles). Make it super clear to the organization both in a meeting and in writing what those changes are. If people used to go to you for X, and now they have to go to New Exec for X, don’t leave that to the guesswork and imagination of your team.
   
3. Get out in front of the fact that your exec team has changed. As I always say, any time you change one person on a team (add or subtract), you have…a new team. Treat a new exec onboarding as such, though this will take time. Team dynamics will change, and you need to drive that process. You also need to make sure any shared language and tools on the team take a beat and include the new person. Did you run a DISC or use Myers-Briggs two years ago with your exec team? Great, do it again with the new team. Did you do a major trust/vulnerability exercise at an exec offsite last year? Better do a new one from scratch. This may sound like extra overhead, but it’s worth it. You don’t want the new person to always feel like the new person who is missing an inside joke. Plus, those kinds of things are always good hygiene for exec teams.
   
4. Begin with the end in mind. On Day 1, your new exec won’t know where the bathroom is, unless you are an all-remote company of course. Your objective is for the new exec to be just as autonomous as all other execs ASAP. So, work backwards from 90 or 180 or some other number of days on the question of autonomy. Build this into your integration checklist and weekly integration check-ins (see above), but note this is also a mental evolution both you and the new exec (and the rest of your exec team and the new person’s direct reports) need to go through. Some areas will be more logical for the new exec to be autonomous on Day 1 or at least Month 1. Some will take longer. Be explicit about defining those things.

Special thanks to my friend Amir for inspiring this post!

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?

Scaling the Team

(This post was requested by my long-time Board member Fred Wilson and is also running concurrently on his blog today.  I’ll be back with the third and fourth installments of “The Best Laid Plans” next Thursday and the following Thursday)

When Return Path reached 100 employees a few years back, I had a dinner with my Board one night at which they basically told me, “Management teams never scale intact as you grow the business.  Someone always breaks.”  I’m sure they were right based on their own experience; I, of course, took this as a challenge.  And ever since then, my senior management team and I have become obsessed with scaling ourselves as managers.  So far, so good.  We are over 300 employees now and rapidly headed to 400 in the coming year, and the core senior management team is still in place and doing well.  Below are five reasons why that’s the case.

1. We appreciate the criticality of excellent management and recognize that it is a completely different skill set from everything else we have learned in our careers.  This is like Step 1 in a typical “12-step program.”  First, admit you have a problem.  If you put together (a) management is important, (b) management is a different skill set, and (c) you might not be great at it, with the standard (d) you are an overachiever who likes to excel in everything, then you are setting the stage for yourself to learn and work hard at improving at management as a practice, which is the next item on the list.
2. We consistently work at improving our management skills.  We have a strong culture of 360 feedback, development plans, coaching, and post mortems on major incidents, both as individuals and as a senior team.  Most of us have engaged on and off over the years with an executive coach, for the most part Marc Maltz from Triad Consulting.  In fact, the team holds each other accountable for individual performance against our development plans at our quarterly offsites.  But learning on the inside is only part of the process.
3. We learn from the successes and failures of others whenever possible.  My team regularly engages as individuals in rigorous external benchmarking to understand how peers at other companies – preferably ones either like us or larger – operate.  We methodically pick benchmarking candidates.  We ask for their time and get on their calendars.  We share knowledge and best practices back with them.  We pay this forward to smaller companies when they ask us for help.  And we incorporate the relevant learnings back into our own day to day work.
4. We build the strongest possible second-level management bench we can to make sure we have a broad base of leadership and management in the company that complements our own skills.  A while back I wrote about the Peter Principle, Applied to Management that it’s quite easy to accumulate mediocre managers over the years because you feel like you have to promote your top performers into roles that are viewed as higher profile, are probably higher comp – and for which they may be completely unprepared and unsuited.  Angela Baldonero, my SVP People, and I have done a lot here to ensure that we are preparing people for management and leadership roles, and pushing them as much as we push ourselves.  We have developed and executed comprehensive Management Training and Leadership Development programs in conjunction with Mark Frein at Refinery Leadership Partners.  Make no mistake about it – this is a huge investment of time and money.  But it’s well worth it.  Training someone who knows your business well and knows his job well how to be a great manager is worth 100x the expense of the training relative to having an employee blow up and needing to replace them from the outside.
5. We are hawkish about hiring in from the outside.  Sometimes you have to bolster your team, or your second-level team.  Expanding companies require more executives and managers, even if everyone on the team is scaling well.  But there are significant perils with hiring in from the outside, which I’ve written about twice with the same metaphor (sometimes I forget what I have posted in the past) – Like an Organ Transplant and Rejected by the Body.  You get the idea.  Your culture is important.  Your people are important.  New managers at any level instantly become stewards of both.  If they are failing as managers, then they need to leave.  Now.

I’m sure there are other things we do to scale ourselves as a management team – and more than that, I’m sure there are many things we could and should be doing but aren’t.  But so far, these things have been the mainstays of happily (they would agree) proving our Board wrong and remaining intact as a team as the business grows.