Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!”  I thought about it more after and came up with five reasons why. 

First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things so much easier and almost friction-free out of the gate here. 

Second, this is the “second lap around the track” for a few of us on the founding team in terms of starting something from scratch, and even those at the company who haven’t done a raw startup before are super experienced professionals and many have worked in and around early stage businesses a lot. All this combines to cut down our error rate, reduce anxiety, and speed up the pace of work. More friction-free or at least low-friction work.

Third, after a 20-year run at Return Path, it’s great to start with a clean slate. No mountains of tech debt and legacy code bases. No installed base of customers with contracts or pricing we no longer like or offer. No institutional debt like a messy cap table, legacy people issues, leases for offices we don’t want or need any more.  This also points to low friction as part of what’s going on…and while that’s a theme, the next two areas are different. 

The fourth reason I’m having a blast at Bolster is that I love — and really live in — the problem space we are working in.  When we started Return Path, I was deeply familiar with email marketing and the challenges faced by our client set and had a good vision for the early product.  But as the years went on, the product got geekier and nicher — and even when it wasn’t, I was never a USER of the product since I’m not an email marketer.  In fact, at our peak of 500 people, the company employed one email marketer and therefore had one user of our own product.  At Bolster, we have three user personas — Member, Client, and Partner.  And I’m all three of them.  I’m constantly in the product, multiple times a day.  I’m deeply familiar with all angles of the executive search and board building process.  It’s MUCH better to be this close to the product, and the same is true for many of our team members.

Finally, the thing I was really worried about with starting another company from scratch — moving from a leadership role into an individual contributor role — has been nothing short of fantastic.  I love working with clients.  I love talking to members.  I love advising and coaching CEOs. I love being a pretend product manager.  I love writing marketing copy.  It’s just great to be on the front lines. (I still love working on strategy and leading the board and engaging with people internally — but those are things that never stopped being part of my day to day.)

I was trying to think if there’s some priority to this list. Almost all of these items are or can be made to be true in your second+ startup. But while four of the five can theoretically be true in your first startup as well, I don’t think it’s quite the same. So I’d have to weight “second lap around the track” a bit higher and also note that during your second lap around the track, hand-picking your team and cap table, appreciating a clean slate, and appreciating individual contributor work are that much easier and things you can appreciate a lot more as a repeat entrepreneur.

It’s fairly rare in a startup or scaleup that you, as a CEO or CXO (Chief [fill in the function] Officer) of any kind, will have significant one-on-one time with other members of the executive suite; instead, you’re most likely to spend time with the team in executive meetings, at offsites, or during all-company events. So, when you do get that one-on-one time it’s important to make sure that it’s not only productive, but that it builds a stronger relationship between you and the other person.

As a CEO I learned that the best way to help people grow and develop, and to further develop a better understanding of each other, is to engage with them in a mix of work and non-work settings.  By that I mean, working together on some aspect of their part of the business. Since each role and each person performing that role are different, there aren’t any hard and fast rules, but I thought I would create a series of posts that provide some ideas on things I’ve done to develop a better relationship, better team, and better company for each CXO in a company. 

I also have a whole series of posts related to each function on the executive team — CFO, CMO, CTO, etc.  So each post is part of two series.  This is the inaugural for both, and it’s quite fitting as Q4 is, for most companies, budgeting and planning season.  So today’s topic is How I engage with the CFO.

When I get the chance to spend time with my CFO I’ve found that we both get the most value working on several “problems” together. For example, we do Mental Math together where we look at key metrics and test them, improve them, or decide to scrap them. We are always attuned to key metrics and from time to time, we project them forward in our minds. What will happen to a key metric if our business scales 10-fold or if it declines 10-fold, for example. 

We are constantly checking to see that our financial and operating results mesh with our mental math.  When looking at our cash balance, we’ll look back at the last financial statement’s cash number and mentally work our way to the current statement: operating profits or losses, big swings in AR or AP, CapEx, and other “below the line” items. Do they add up?  Can we explain what we’re seeing in plain English to other leaders or directors?  The same thing applies to operating metrics — the size of our database, our headcount, our sales commission rate, and so on.

I’ve found that by working on the mental math that we actually come to understand the dynamics of the business far better than merely looking at the numbers or comparing the numbers. The mental math approach forces both you and the CFO to engage with the results, question them, and anticipate how slight changes can impact the company going forward. And once you get to that point, you have the ability to creatively think about how you want to go forward.  Here’s a simple example from the early days of Return Path.  One day, my long-time business partner and CFO Jack and I were doing mental math around how many clients each of our Customer Success team members was handling.  We had an instinct that it wasn’t enough — and we did a quick “how many of those reps would we need if we were doing $100mm in revenue” check and blanched at the number we came up with.  That led to a major series of investments in automation and support systems for our CS team.

Another way that the CFO and I work together is in a game called “spotting the number that seems off.” In any spreadsheet or financial analysis there is bound to be something that doesn’t seem quite right and for some uncanny reason, I am really good at finding the off number. I’m sure this has driven CFOs crazy over my career, but for whatever reason I have some kind of weird knack for looking at a wall of numbers and finding the one that’s wrong.  It’s some combination of instincts about the business, math skills, and looking at numbers with fresh eyes. It’s not an indictment on the CFO’s results and it’s not a “gotcha” moment but it’s part of the partnership I have with my CFO that improves the quality of our work and quantitative reasoning. My hunch is that looking at something with fresh eyes, as opposed to being the person who produces the numbers in the first place, makes it easier to spot something that’s not quite right. Kind of like an editor working with you on an article or book—they always seem to pick up and point out something that you didn’t see even though you spent hours creating it and hours more reading and re-reading something.

A third way to work with the CFO is to create stories with numbers. The best CFOs are the ones who are also good communicators — but that only partly means they are good at public speaking.  Being able to tell a story with numbers and visuals is an incredibly important skill that not all CFOs possess.  Whether the communication piece is an email to leaders, a slide at an all-hands meeting, or a Board call, partnering with a CFO on identifying the top three points to be made and coming up with the relevant set of data to back the number up — and then making sure the visual display of that information is also easy to read and intellectually honest, can be the difference between helping others make good decisions or bad ones.

Of course, a CFO could create stories on their own but like much of storytelling (like screenwriters for movies, plays, or sitcoms, for example), the creative storytelling usually happens with a team. In presenting financial data to others so that it makes an impact, so that it motivates them to take an action or change a behavior, a team approach is best and the CEO-CFO team can be much more effective than either one of them alone.

You won’t have a lot of time to spend 1:1 with any given CXO on your team, including the CFO, but you can make the time you spend together work to your favor in developing a stronger relationship between you and the CFO, and help you build a stronger company that can scale quickly. Without a deep understanding and strong relationship with others on your leadership team, your decision-making, speed, and risk-taking can suffer. Make sure every minute you spend with the CFO is productive. That’s why working on things together like mental math, spotting the off number, and storytelling, can be powerful ways to help you build a better company. 

(Also posted to the Bolster Blog).

Book Short:  Required Reading, Part II

Every once in a while, a business book nails it from all levels.  Well written, practical, broadly applicable to any size or type of organization, full of good examples, full of practical tables and checklists.   The Leadership Pipeline, which I wrote about here over six years ago, is one of those books — it lays out in great and clear detail a framework for understanding the transition from one level to another in an organization and how work behaviors must change in order for a person to succeed during and on the other side of that transition.  In an organization like Return Path‘s which is rapidly expanding and promoting people regularly, this is critical.  We liked the book so much that we have adopted a lot of its language and have built training courses around it.

The book’s sequel, The Performance Pipeline (book, Kindle), also by Stephen Drotter but without the co-authors of the original book, is now out — and it’s just as fantastic.  The book looks at the same six level types in an organization (Enterprise Manager, Group Manager, Business Manager, Functional Manager, Manager of Managers, Manager of Others, and Self Managers/Individual Contributors) and focuses on what competencies people at each level must have in order to do their jobs at maximum effectiveness — and more important, in order to enable the levels below them to operate in an optimal way.

This book is as close to a handbook as I’ve ever seen for “how to be a CEO” or “how to be a manager.”  Coupled with its prequel, it covers the transition into the role as well as the role itself, so “how to become a CEO and be a great one.”  As with the prequel, the author also takes good care to note how to apply the book to a smaller organization (from the below list, usually the top three levels are combined in the CEO, and often the next two are combined as well).  No synopsis can do justice to this book, but here’s a bit of a sense of what the book is about:

• Enterprise Manager:  role is to Perpetuate the Enterprise and develop an Enterprise-wide strategic framework – what should we look like in 15-20 years, and how will we get the resources we need to get there?
• Group Manager:  role is to manage a portfolio of businesses and develop people to run them
• Business Manager:  role is to optimize short- and long-term profit and develop business-specific strategies around creating customer and stakeholder value
• Functional Manager:  role is to drive competitive advantage and functional excellence
• Manager of Managers:  role is to drive productivity across a multi-year horizon, and focus
• Manager of Others:  role is to enable delivery through motivation, context setting, and talent acquisition
• Self Managers/Individual Contributors:  role is to deliver and to be a good corporate citizen

I could write more, but there’s too much good stuff in this book to make excerpts particularly useful.  The Performance Pipeline is another one of those rare – “run, don’t walk, to buy” books.  Enjoy.  For many of my colleagues at RP – look out – this one is coming!

Selling a Line of Business

It’s been a couple of years since Return Path decided to focus on our deliverability business by divesting and spinning out our other legacy businesses. That link tells some of the story, and the rest is that subsequently, Authentic Response divested part of the Postmaster Direct business to Q Interactive.  Those three transactions, plus a number of experiences over the years on the buy side of similar transactions (Bonded Sender, Habeas, NetCreations), plus my learnings from talking to a number of other CEOs who have done similar things over the years, form the basis of this post.  The Authentic Response spin-out was also partially chronicled by Inc. Magazine in this article earlier this year.

It’s an important topic — as entrepreneurs build businesses, they frequently end up creating new revenue opportunities and go off on productive tangents.  Those new lines of business might or might not take off; but sometimes they can take off and still, down the road, end up being non-core to the overall mission of the company and therefore candidates for divestiture.  Even if they are good businesses, the overall enterprise might benefit from the focus or cash provided by a sale.  Look at the example of Occipital building the Red Laser app, then selling it to eBay to finance the rest of their business.

Here are some of the signs of a successful divestiture:

• Business is truly non-core or relies on starkly different competencies for success (e.g., one is B2B, the other is B2C)
• Business is growing rapidly and requires assistance to scale properly (either technology, or sales)
• Business has its own culture and operations and “a life of its own”

Conversely, here are some of the reasons why a divestitures of a business unit might stall or fail:

• Lack of a very compelling story as to why you’re selling the business unit
• Stand-alone financials of the unit are too hard for the buyer to determine with confidence
• Operations of the unit too tethered to the mothership
• There is some problem with the leadership of the unit (there is no stand-alone leader, the leader isn’t involved in the divestiture, the leader isn’t squarely behind the divestiture)
• Business performance weakens during the process

I have a couple points of advice to entrepreneurs in this situation.  The first is to clarify for yourself up front:  are you selling a true line of business, or are you selling assets?  If you are selling assets, you need to clearly define what they are, and what they aren’t, and you need to make sure all legal details (contracts, IP, etc.) are buttoned up before the process starts.

If you are selling a true line of business, beware that buyers will not be interested in doing any hard work, or if they feel like they have to do hard work, the price they pay for the business will reflect that in the form of a steep, steep discount.  The financials must be understandable and credible on a stand-alone basis.  The business must be completely separated from the core already.  The business must have its own management team, completely aligned with the decision to sell.

You also have to be extremely cognizant of the human aspects of what you’re doing.  Every culture is different, and I’m not advocating one style over another, but selling or spinning out a business is very different than selling a company.  There’s going to be a big difference in reactions, perceptions, hopes, and fears between the people in the core who are staying, and the people in the business unit that’s going.  Having a heightened awareness of those differences and factoring them into your communications plan is critical to success, as a poorly managed effort can end up harming both sides.

In terms of valuation expectations, don’t expect to get any credit for synergies.  You have to present them and sell them, and they may make the different between getting a deal done and not, but they will most likely not impact the price you get for the divestiture.

Finally, remember that buyers understand your psychology as well.  They know you’re selling the business for a reason (you need to raise cash, you’re concerned about its future performance, it’s become a distraction or has the potential to suck scarce resources out of your core, etc.).  They will completely understand the costs you carry, whether financial, opportunity, or mental, in continuing to own the business.  And they will factor that into the price they’re willing to offer.  Of course, as with all deals, the best thing you can do to maximize price is have multiple interested parties bidding on the deal!

Book Short:  Awesome Title, So-So Book

Strategy and the Fat Smoker (book, Kindle), by David Maister, was a book that had me completely riveted in the first few chapters, then completely lost me for the rest.  That was a shame.  It might be worth reading it just for the beginning, though I’m not sure I can wholeheartedly recommend the purchase just for that.

The concept (as well as the title) is fantastic.  As the author says in the first words of the introduction:

We often (or even usually) know what we should be doing in both personal and professional life.  We also know why we should be doing it and (often) how to do it.  Figuring all that out is not too difficult.  What is very hard is actually doing what you know to be good for you in the long-run, in spite of short-run temptations.  The same is true for organizations.

The diagnosis is clear, which is as true for organizations as it is for fat people, smokers, fat smokers, etc.  The hard work (pain) is near-term, and the rewards (gain) are off in the future, without an obvious or visible correlation.  As someone who has had major up and down swings in weight for decades, I totally relate to this.

But the concept that

the necessary outcome of strategic planning is not analytical insight but resolve,

while accurate, is the equivalent of an entire book dedicated to the principle of “oh just shut up and do it already.”  The closest the author comes to answering the critical question of how to get “it” done is when he says

A large part of really bringing about strategic change is designing some new action or new system that visibly, inescapably, and irreversibly commits top management to the strategy.

Right.  That’s the same thing as saying that in order to lose weight, not only do you need to go on a diet and weigh yourself once in a while, but you need to make some major public declaration and have other people help hold you accountable, if by no other means than causing you to be embarrassed if you fail in your quest.

So all that is true, but unfortunately, the last 80% of the book, while peppered with moderately useful insights on management and leadership, felt largely divorced from the topic.  It all just left me wanting inspirational stories of organizations doing the equivalent of losing weight and quitting smoking before their heart attacks, frameworks of how to get there, and the like.  But those were almost nonexistent.  Maybe Strategy and the Fat Smoker works really well for consulting firms – that’s where a lot of the examples came from.  I find frequently that books written by consultants are fitting for that industry but harder to extrapolate from there to any business.

Managing in a Downturn

I spoke at a NextNY event last night along with several others, including fellow entrepreneur David Kidder from Clickable and angel investor Roger Enhrenberg about this fine topic (Roger wrote a great post on it here) and thought I’d share a few of the key points made by all of us for anyone trying to figure out what to do tactically now that Sequoia has told us to be afraid, very afraid.

Hope is Not a Strategy:  Your business is not immune. It will do what everyone else’s will. Struggle to hit its numbers. Struggle to collect bills. Lose customers. There is no reason to hope you’ll be different.

Get Into the Jet Stream:  Develop your core revenue streams — and make sure they’re really your revenue, not just skimming tertiary revenue out of the ecosystem.  Investors will look to see how sustainable your model is with more scrutiny than ever.

It’s a Long Road to Recovery:  I don’t care what people say. There is no true “v-shaped” bounceback from a true downturn. Plan for a long (4-8 quarter) time to return to normalcy.

Budget Early and Often:  Things change rapidly in this kind of environment. Make sure you reforecast, especially cash flows and cash, monthly when you close the books.

Don’t Stop Thinking About Tomorrow:  If you have a real business, you need to be it for the long haul. Keep pursuing opportunities. Keep investing in the future. Don’t pare back your vision and ambitions. Just make more conservative investments, insist on shorter payback windows, and adjust expectations about timeframes.

Leadership Counts:  Your people are nervous. They’re concerned about their own bank accounts. Their jobs. Be even more present, more transparent, and more communicative. And set the right tone on expenses with your own decisions. The troops need to know that you care about them — and that the big boss has a steady hand on the wheel.

Doing Well by Doing Good, Part IV

This series of posts has mostly been about things that people or companies do that help make the world a better place — sometimes when it’s their core mission, other times (here and here) when it becomes an important supporting role at the company.

Today’s post is different — it’s actually a Book Short as well of a new book that’s coming out later this fall called Green to Gold:  How Smart Companies Use Environmental Strategy to Innovate, Create Value, and Build Competitive Advantage, published by Yale Press and written by Daniel Esty (a Yale professor and consultant), and a good friend of mine, Andrew Winston, a corporate sustainability consultant.

Green to Gold is a must-read for anyone who (a) holds a leadership position in business or is a business influencer, and (b) cares about the environment we live in.  Its subtitle really best describes the book, which is probably the first (or if not, certainly the best) documentation of successful corporate environmentalstrategy on the market.

It’s a little reminiscent to me of Collins Built to Last and Good to Great in that it is meticulously researched with a mix of company interviews/cooperation and empirical and investigative work.  It doesn’t have Collins “pairing” framework, but it doesn’t need to in order to make its point.

If you liked Al Gore’s movie, An Inconvenient Truth, this book will satisfy your thirst for information about what the heck the corporate world is doing or more important, can do, to do its part in not destroying our ecosystem.  If you didn’t like Gore’s movie or didn’t see it because you don’t like Al Gore or don’t think that many elements of the environmental movement are worthwhile, this book is an even more important read, as it brings the theoretical and scientific to the practical and treats sustainability as the corporate world must treat it in order to adopt it as a mainstream practice — as a driver of capitalistic profit and competitive advantage.

This is a really important work in terms of advancing the cause of corporate social responsibility as it applies to the environment.  Most important, it proves the axiom here that you can, in fact, Do Well by Doing Good.  If you’re interested, you can pre-order the book here.  Also, the authors are writing a companion blog which you can get to here.

Help Me, Help You, Part II

Thanks to the nearly 100 readers who responded to my reader survey this past week.  While I’m not sure it’s a truly statistically significant base of OnlyOnce’s audience (I’ll have to ask my friends over at Authentic Response), I’ll treat it like it is.  Here’s what I learned.  First, the general results:

• Satisfaction levels are good – 46% are regular readers and love it, 48% read occasionally and think it’s ok, and only 6% gave it an “eh – wouldn’t miss it if it went away”
• Entrepreneurship is the most popular topic, with 86% interest, and Leadership/Management is a close second at 82%.  Online/Email Marketing came in at 61% and Book Reviews at 43%.  Current Affairs and Travel (which I almost never use) were 31% and 25%, respectively
• 72% of people feel frequency at 1-2 posts a week is on target.  Only 4.5% want fewer posts, and 24% (those kind souls) want it more often
• Most people other than Return Path staff found the site through a link on another blog rather than search

Next, the open-ended comments were interesting.  A summary snapshot:

• Positive comments were generally about tone and candid approach, succinct posts, and topics.  One nice person noted his/her favorite thing was “the author” (thank you Mom/Dad/Grandma/Mariquita/Michael)
• Constructive comments varied.  Some good ones are noted below:
• “assumes a level of knowledge not everyone has”
• “too heralding of the VC view of the world”
• “too much focus on email/marketing,” “too local/American” (that’s who I am, though)
• “ I would like to see more about what it takes to be a CEO in day to day operations. what skills do you find you need, what obstacles do you come across, issues with driving a company.”
• “A little too much PRish in regards to Return Path”
• “It seems like everything you write about is too positive. Or at least a negative story with a happy ending. Nothing about what sucks to run a company. I run one and a lot of it does suck.”
• “Not enough personal stuff — who is the author?” (see the About Me link on the blog)
  
• “The word vigilante is bandied around way too much by the author”
• And of course someone noted as constructive feedback that I haven’t yet mentioned my mother’s name (sorry, Mom/Joyce!).  And one person suggested I shave.  Thanks, really.

Finally, the demographics of my audience:

• 3 % are under 24, 45% are 25-34, 41% are 35-49, 11% are over 49
• 80% male and 20% female (surprising)
• Company data wasn’t so interesting, or I phrased the question poorly – but one takeaway is that about 1/2 of readers seem to be “in the industry” generally speaking, with lots of Return Path staff subscribing as well as lots of other entrepreneurs and a handful of VCs
• Level/title was more interesting – nearly half the audience is SVP-level or above at their company

Thanks again, everyone, and I’ll take note of this feedback for future postings!

Book Short:  Virtuous Cycle

Danny Meyer’s Setting the Table: The Transforming Power of Hospitality in Business is a fun read if you’re a New Yorker who eats out a lot; a good read for entrepreneurs around scaling leadership skills as the business grows; and a great read for anyone who runs a serious customer service-oriented organization.  I’ve eaten at all of his restaurants multiple times over the years except for the new ones at MOMA (perhaps a few too many times at the Shake Shack), and while I like some more than others (perhaps the Shake Shack a bit too much), they all do have great hospitality as a common theme.

While there are a lot of good lessons in the book, Meyer talks about something he calls the Virtuous Cycle of Enlightened Hospitality that matches the general hierarchy of constituents or stakeholders in a business that I refer to at Return Path:   employees, customers, community, suppliers, investors.  His general point is that if you have happy employees, they make for happy customers, and returns for investors will follow.  While the specifics may or not be true of all businesses, I bet the first and last item are — especially for service-oriented businesses in any industry.  I wish we had a better handle on the Community aspect at Return Path, but we at least do an OK job at it, especially given the geographic diversity within the company.

(Note this was one of Fred’s favorite parts of the book as well from his review — nice to see a professional investor in agreement!)

Book Short:  Crazy Eights

In honor of Return Path being in the midst of its eighth year, I recently read a pair of books with 8 in the title (ok, I would have read them anyway, but that made for a convenient criterion when selecting out of my very large “to read” pile).

Ram Charan’s latest, Know-How:  The 8 Skills That Separate People People Who Perform From Those Who Don’t, was pretty good and classic Charan.  Quick, easy to skim and still get the main points.  The book lost a little credibility with me when Charan lionized Verizon (perhaps he uses a different carrier himself) and Bob Nardelli (the book was published before Nardelli’s high profile dismissal), but makes good points nonetheless.  Some of the 8 Skills he talks about are what you’d expect on the soft side of leadership — building the team, understanding the social system, judging people — but his best examples were particularly actionable around positioning, goal setting, and setting priorities.  The book reminded me much more of Execution and much less of Confronting Reality (which is a good thing).

For years I’ve felt like the last person around to still not have read The 7 Habits of Highly Effective People, so I thought I’d skip straight to the punchline and read Stephen Covey’s newer book, The 8th Habit:  From Effectiveness to Greatness.  Fortunately, as I’d hoped, the new book summarizes the prior book several times over, so if you haven’t read the first, you could certainly just start with this one.  The book also comes with a DVD of 16 short films, some of which are great — both inspirational and poignant.  Unlike most business books, the 8th Habit is NOT skimmable.  It almost has too much material in it and could probably be read multiple times or at least in smaller pieces.  The actual 8th habit Covey talks about is what he calls Find Your Voice and Help Others Find Their Voices and is a great encapsulation of what leading a knowledge worker business is all about.  But the book is much deeper and richer than that in its many models and frameworks and examples/tie-ins to business and goes beyond the “touchy feely” into hard-nosed topics around execution and strategy.

Now I’m looking for the DVD of the first season of Eight is Enough!

Collaboration is Hard, Part I

Every year when we do 360 reviews, a whole bunch of people at all levels in the organization have “collaboration” identified as a development item.  I’ve been thinking a lot about this topic lately and will do a two-part post on this.  So, first things first…what is collaboration and why is it so important?

Let’s start with the definition of collaboration from our friends at Wikipedia:

Collaboration is a process defined by the recursive interaction of knowledge and mutual learning between two or more people who are working together, in an intellectual endeavor, toward a common goal which is typically creative in nature. Collaboration does not necessarily require leadership and can even bring better results through decentralization and egalitarianism.

What does that mean in a business setting?  It means partnering with a colleague (either inside or outside of the company) on a project, and through the partnering, sharing knowledge that produces a better outcome than either party could produce on his or her own.  Interestingly, the last sentence of the definition implies that collaboration can happen across levels in an organization but is generally more effective when the parties who are collaborating are on somewhat equal footing.

Why is collaboration important?  There are probably a zillion reasons.  Let me take a stab at what I think are three important ones:

1. It’s not about hard assets any more. In a knowledge economy/company, sharing information and learnings is critical.  And that’s what’s at the heart of the collaborative process.  Each person in the organization does a different job; even those who are in the same role have different experiences with their role and different interactions both internally and externally as a result.  A collaborative process that by definition involves learning drives the organization forward and to a better place.  An example…if you have a deep working knowledge of your product, and your counterpart in marketing has a deep working knowledge of public relations, collaborating on a PR strategy to launch the product’s latest feature means that you will learn more about public relations and your colleague will learn more about your product.  In the end, you both get smarter, and the collective intellect of your organization grows — so your company gains incremental advantage over the competition as a result.
2. No man is an island. Most functions and business units are in some way interdependent.  Think back to the example of product and PR above.  Both parties learn through collaboration and make things better for the future.  Here’s the rub, though — the collaboration in that example is the only way to produce the right outcome.  So the prior point illustrates offense, but this one illustrates defense.  Failure to collaborate in this simple case would lead to a misguided PR launch strategy for the new product feature.  Either product would dictate the release strategy and text — missing some important subtleties about what reporters will/won’t pick up or without thinking through how different constituencies will react to the messaging — or PR would dictate the release strategy and timing — missing important but subtle points of competitive differentiation in the product features or botching a market-specific window for the announcement.
3. Leverage is king. If the first point illustrates offense (collaboration moves the organization forward) and the second one illustrates defense (failure to collaborate suboptimizes the quality of results), this one illustrates productivity (perhaps a subset of offense).  Collaboration gives leverage, which in turn gives productivity.   Let’s not pick on our poor product and PR people this time, though.  Let’s think about one of the most difficult things to do, which is to hire good people.  As I wrote a few years ago in The Hiring Challenge, the three things to do when hiring (which are all hard) are defining the job properly, finding the time to do it right, and remembering that the process doesn’t stop on the person’s first day on the job.  So where does collaboration come in?  Once your company is big enough to have a good HR person or team, the collaborative approach to having them help you with recruiting is the best option.  Sure, you can “throw it over the wall” to HR — give them a job title and location and comp range and see what happens.  And you will get some candidates, some of which might be ok.  Or you can forget about HR and try to do it yourself and not have time to get it right.  Or you can collaborate, bring HR into the discussion about the need for the position, the skills required, and the fit with your organization, even write a job description with HR and discuss which companies or types of companies you want to see on candidates’ resumes — and voila!  HR can go off and do 10x the work at 10x the quality.  For a little more up-front effort than the “throw it over the wall” approach, you leveraged yourself tremendously through what can be a very time consuming process.

Although my examples are by nature from my own industry for the past 12+ years, it’s hard to think of too many organizations or industries where collaboration isn’t critical to success.  Even in companies like investment banks or strategy consulting firms, which traditionally are very hierarchical, command-and-control organizations filled with brilliant individual contributors, the most successful companies (think Goldman Sachs, McKinsey) are the ones that seem to foster more collaboration than others in the development of their people and the development of shared intellectual capital that helps drive the organization forward and ahead of its competition.

In Part II, I’ll answer the title question here…why is collaboration hard?  Stay tuned!