The iPad’s Limitations as a Business Device

I love my iPad.  Let me just start with that.  I’ve found lots of use cases for it, and it’s very useful here and there for work.  But I’ve seen a bunch of people trying to use it as a primary business device, which I can’t quite figure out.  Here are the things that prevent me from making it my main business device:

• lack of keyboard (can mitigate with the keyboard dock, which I have)
• lack of mouse (not a killer limitation, just takes some getting used to, also the arrows on the keyboard dock help)
• lack of connection to files and true Office compatibility (this can largely be mitigated through a combination of the Dropbox or Box.net app and the QuickOffice app)
• lack of multitasking (this is the main killer)

Much of the time, I need to be rapidly switching between and simultaneously using email, the web, and multiple Office documents.  Having to basically shut down each one and then fire up another instead of having them all up at once on multiple monitors or at least easily accessible via alt-tab is a big pain, especially when trying to cut and paste things from one to another.   The iPad is awesome for many many things, and for limited work usage (other than complex spreadsheets), it works “well enough.”  But I would find it difficult to make it my primary business machine other than for a fairly short (1 day) business trip.

I recently returned from a six-week sabbatical. It was fantastic. I blogged about it here if you’re curious about the experience. It turned out that, while I was gone, we had probably the most successful, least dramatic six weeks in our 10 year history. I had assumed that’s because the team buckled down while I was out, and so did our Board.

Little did we know what really happened during that six week stretch. It’s often said that when the cat’s away, the mice play. The short video below is what greeted me today at an all-hands meeting. If the team can crank out such great work and have this much fun while I’m out, well, I guess I should take more time off!

Keeping Commitments

Today’s post is another in the series about our 13 core values at Return Path, about making commitments.  The language of our value specifically is:

We believe in keeping the commitments we make, and we communicate obsessively when we can’t

Making and keeping commitments is not a new value – it’s one of Covey’s core principles if nothing else.  I’m sure it has deeper roots throughout the history of mankind.  But for us, this is one of those things that is hard wired into the social contract of working here.  The value is more complicated than some of the other ones we have, and although it is short, it has three components that worth breaking down:

• Making commitments:  Goal setting, whether big company-wide goals, or smaller “I’ll have it to you by Tuesday” goals, is the foundation for a well-run, aligned, and fast-paced organization
  
• Keeping commitments:  If you can’t keep the overwhelming majority of your commitments, you erode the trust of your clients or colleagues and ultimately are unable to succeed
  
• Communicating when commitments can’t be met:  Nobody is perfect.  Sometimes circumstances change, and sometimes external dependencies prevent meeting a goal.  The prior two parts of this value statement are, in my mind, pay to play.  What separates the good from the great is this third piece — owning up loud and clear when you’re in danger of blowing a goal so that those who are counting on you know how to reset their own work and expectations accordingly
  

It’s worth noting on this one that the goal is as relevant EXTERNALLY as it is INTERNALLY.  Internal commitments are key around building an organization that knows how to collaborate and hand work off from group to group.  External commitments — from meeting investor expectations to client deliverables — keep the wheels of commerce flowing.

I’m enjoying articulating these values and hope they’re helpful for both my Return Path audience and my much larger non-Return Path audience.  More to come over time.

Why We Occasionally Celebrate International Talk Like a Pirate Day

No kidding – next Monday is September 19, and that is, among other things, International Talk Like a Pirate Day. We’ve done a variety of things to celebrate it over the years, not the least of which was a series of appropriately-themed singing telegrams we sent to interrupt all-hands meetings.  I can’t remember why we ever started this particular thing, but it’s one of many for us.  Why do we care?  Because

We are serious and passionate about our job and positive and light-hearted about our day

This is another one of Return Path’s philosophies I’m documenting in my series on our 13 core values.

I’m not sure I’d describe our work environment as a classic work hard/play hard environment. We’re not an investment bank. We don’t have all 20something employees in New York City. We’re not a homogeneous workforce with all of the same outside interests. So while we do work hard and care a lot about our company’s success, our community of fellow employees, solving our clients’ problems, and making a big impact on our industry and on end users’ lives, we also recognize that “playing hard” for us means having fun on the job.

It’s not as if we run an improv comedy troop in the lunch room or play incessant practical jokes on each other (though I have pulled off a couple sweet April Fool’s pranks over the years). But as the value is worded, we try to set a lighthearted and positive atmosphere. This one is a little harder to produce concrete examples of than some of our other core values that I’ve written up, but that doesn’t mean it’s any less important.

Whether it’s talking like a pirate, paying quiet homage to our unofficial mascot – the monkey, stopping for a few minutes to play a game of ping pong, or just making a silly face or poking fun of a close colleague in a meeting, I’m so happy that our company and Board have this value hard-wired in.  Life’s just too short not to have fun at every available opportunity!

B+ for Effort?

Effort is important in life.  If Woody Allen is right, and 80% of success in life is just showing up, then perhaps 89% is in showing up AND putting in good effort.  But there is no A for Effort in a fast-paced work environment.  The best you can get without demonstrating results is a B+.

The converse is also true, that the best you can get with good results AND without good effort is a B+.

Now, a B+ isn’t a bad grade either way.  But it’s not the best grade.  In continuing with this series of our 13 core values at Return Path, the next one I’ll cover is:

We believe that results and effort are both critical components of execution

We’ve always espoused the general philosophy that HOW you get something done is quite important.  For example, if the effort is poor and you get to the right place, maybe you got lucky.  Or even worse, maybe you wasted a lot of time to get there.  Or if you burned your colleagues or clients in the process of getting to the right place, a positive short-term result can have negative long-term consequences.

But when all is said and done, even with the most supportive culture that values effort and learning a lot (more on that in the next post in this series), results speak very loudly. Customers don’t give you a lot of credit for trying hard if you’re not effectively delivering product or solving their problems.  And investors ultimately demand results.

Our “talent development” framework at Return Path – the thing that we use to measure employee performance, reflects this dual view of execution:

The X axis is clearly labeled “Performance,” meaning results, and the Y axis is labeled “Potential – RP Expectations,” which basically means effort and fit with the culture at Return Path.  We plot out employees on the basis of their quantitative scores coming out of their performance reviews on this grid every year.  Which box any given employee falls in has a lot to do with how that employee is managed and coached in the coming months.  We’re always trying to move people up and to the right!

The definitions of the different boxes in this framework are telling and speak to the subject of this post.  To be an A player here, you have to excel in both effort and results – that’s our definition of successful execution.

Happy Thanksgiving, everyone!  We’re getting to the end of this series…only two more to go.

Management by Chameleon

When I first became a manager, back in the MovieFone days, I had the good fortune to have an extreme case of “first time manager”– I went from managing nobody to managing 1 person to managing something like 20 people inside 6 months.  As a result, I feel like I learned a couple lessons more quickly than I might otherwise have learned them.  One was around micromanagement and delegation.  When I went from 0 to 1 direct report, I micromanaged (I still feel bad about that, Alissa).  But when I went from 1 to 20, I just couldn’t micromanage any more, and I couldn’t do it all myself.  I had to learn how to delegate, though I’m sure I was clumsy at it at first.

The larger lesson I learned when I went from 1 direct report to 5 (each of whom had a team underneath her) is that different people and different teams require different management styles and approaches.  This is what I call management by chameleon.  As a chameleon has the same body but shows it differently as situations warrant, you can have a consistent management philosophy but show it differently when you are with different direct reports or teams.

On my original team at MovieFone, I had one person who was incredibly quantitative and detail/process oriented and who indirectly managed a lot of products and processes outside our group.  I had another who was a complete newbie to the company and to an operating role (she was a former management consultant) with a large number of entry level employees in the field.  I had another who was an insanely creative insomniac trying to blaze new trails and create editorial content inside a technology company.  A fourth was a very broad thinking generalist, one of those great corporate athletes, who managed whatever fell between the cracks.  And the last was a commercial banker turning herself into a relationship management specialist working with an unorthodox business model and partners who half the time felt threatened by us.

In short, I had five incredibly different people to manage with five incredibly different functions and team types/employees under them.

And I learned over time — I like to think I learned it in a hurry, but I’m sure it took a couple of years, and I’m probably still working on it — that trying to manage those people and the second-level identically was counterproductive.  A small example:  8 a.m. meetings for the insomniac never worked well.  A bigger example:  diving into strategic topics with the former consultant who just joined the team and had never managed anyone before was a little bit of focusing on the forest and forgetting about the trees.

At the end of the day, you are who you are as a manager.  You are hard-charging, you are great at developing individuals, you seek consensus.  But how you show these traits to your team, and how you get your team to do the work you need them to do, can differ greatly person by person.

Peter Principle, Applied to Management

My Management by Chameleon Post from a couple weeks ago generated more comments than usual, and an entertaining email thread among my friends and former staff from MovieFone.  One comment that came off-blog is worth summarizing and addressing:

There are those of us who should not manage, whose personalities don’t work in a management context, and there is nothing wrong with not managing.  Also, there promotion to management by merit has always been a curiosity to me. If I am good at my job, why does it mean that I would be good at managing people who do my job? In other words, a good ‘line worker’ doth not a good manager make. I’d prefer to see people adept at being team leads be hired in, to manage, then promotion of someone ill-fitted for such a position be appointed from within. This latter happens far to often, to the detriment of many teams and companies.

For those of you not familiar with the Peter Principle, the Wikipedia definition is useful, but the short of it is that “people are promoted to their level of incompetence, when they stop getting promoted…so in time, every post tends to be occupied by an employee who is incompetent to carry out their duties.”

Back when I worked in management consulting, I always used to wonder how it was that all the senior people spent all their time selling business.  They hadn’t been trained to sell business.  And a lot of the people great at executing complex analysis and client cases hated selling. Or look at the challenge the other way around:  should a company take its best sales people and turn them into sales managers?

We’ve had numerous examples over the years at Return Path of people who are great at their jobs but make terrible, or at least less great, managers.  The problem with promoting someone into a management role mistakenly isn’t only that you’re taking one of your best producers off “the line.”  The problem is that those roles are coveted because they almost always come with higher comp and more status; and if a promotion backfires, it generally (though not always) dooms the employment relationship.  People don’t like admitting failure, people don’t like “moving backward,” and comp is almost always an issue.

What can be done about this?  We have tried over the years to create a culture where being a senior individual contributor can be just as challenging, fun, rewarding, impactful, and well compensated as being a manager, including getting promotions of a different sort.  But there are limits to this.  One obvious one is at the highest levels of an organization, there can only be one or two people like this (at most) by definition.  A CEO can only have so many direct reports.  But another limit is societal. Most OTHER companies define success as span of control.  You get a funny look if you apply for a job with 15 years of experience and a $100k+ salary yet have never managed anyone before.  After all, the conventional wisdom mistakenly goes, how can you have a big impact on the business if all you do is your own work?

The fact is that management is a different skill.  It needs to be learned, studied, practiced, and reviewed as much as any other line of work.  In most ways, it’s even more critical to have competent and superstar managers, since they impact others all day long.  Obviously, people can be grown or trained into being managers, but the principle of my commenter – and “Peter” – is spot on:  just because you are good at one job doesn’t mean you should be promoted to the next one.

I’m not sure there’s a good answer to this challenge, but I welcome any thoughts on it here.

Over the past several months, I’ve published two series of posts on the Bolster blog about Boards. The first series is designed to help CEOs better understand how to build, diversify, and scale their boards of directors. I’ll write about the second one next week. Both series of posts will feature in the second edition of Startup Boards, a book originally published in 2014 by Brad Feld and Mahendra Ramsinghani. The second edition, which is also co-authored by me, will be out late this year or early next year.

As I’ve gone about building our business at Bolster, including leading several dozen board searches for companies of all sizes and stages from pre-revenue to public, I’ve noticed that there are still a lot of questions among company leaders about board-building best practices. Without a lot of documentation and analysis about private company boards, most startup CEOs learn about building and managing boards through trial and error. As a result, this critical component of corporate governance is often under-utilized. Directors’ skills and networks are under-leveraged, term lengths are rarely re-negotiated, and board diversity becomes an afterthought.

This is why I set out to publish a comprehensive look at building boards, written from one CEO to another. You can read the full series here:

• The New Way to Scale A Board of Directors
• The Purpose of a Board
• Size and Composition of Boards
• Board Evolution and Turnover
• Diversity in the Boardroom and The Importance of Appointing First-time Directors
• What to Look for in a Director
• How to Recruit and Interview Directors
• How to Onboard Directors, Especially First-time Directors
• How to Compensate Independent Directors
• How to Build a Director Bench or Advisory Board
• How to Evaluate Your Board

The team at Bolster also compiled all of these posts into an eBook you can download by clicking on this link, entitled How to Build Your Board. No matter where you are in your journey as a CEO or company leader, I hope this is a resource and reference for you to look back on over time.

By the way – if you’d like to get access to more content like this or start a search for an independent director for your own board, you can sign up as a Bolster client here.

I’ve always been a big believer in the consistent application frameworks for business thinking and decision-making.  Frameworks are just a great starting point to spark conversation and organize thinking, especially when you’re faced with a new situation.  Last year, I read Tom Friedman’s new book, Thank You for Being Late: An Optimist’s Guide to Thriving in the Age of Accelerations, and he had this great line that reminded me of the power of frameworks and that it extends far beyond business decision-making:

When you put your value set together with your analysis of how the Machine works and your understanding of how it is affecting people and culture in different contexts, you have a worldview that you can then apply to all kinds of situations to produce your opinions. Just as a data scientist needs an algorithm to cut through all the unstructured data and all the noise to see the relevant patterns, an opinion writer needs a worldview to create heat and light. 

In Startup CEO, I wrote about a bunch of different frameworks we have used over the years at Return Path, from vetting new business ideas to selecting a type of capital and investor for a capital raise.  I blogged about a new one that I learned from my dad a few months ago on delegation.  One of my favorite business authors, Geoffrey Moore, has developed more frameworks than I can count and remember about product and product-market fit.

But all frameworks can go stale over time, and they can also get bogged down and confused with pattern recognition, which has limitations.  To that end, Friedman also addressed this point:

But to keep that worldview fresh and relevant…you have to be constantly reporting and learning—more so today than ever. Anyone who falls back on tried-and-true formulae or dogmatisms in a world changing this fast is asking for trouble. Indeed, as the world becomes more interdependent and complex, it becomes more vital than ever to widen your aperture and to synthesize more perspectives.

Again, although Friedman talks about this in relation to journalism, the same can be applied to business.  Take even the most basic framework, the infamous BCG “Growth/Share Matrix” that compares Market Growth and Market Share and divides your businesses into Dogs, Cash Cows, Question Marks, and Stars.  Digital Marketing has disrupted some of the core economics of firms, so there are a number of businesses that you might previously have said were in the Dog quadrant but due to improved economics of customer acquisition can either be moved into Cash Cow or at least Question Mark.  Or maybe the 2×2 isn’t absolute any more, and it now needs to be a 2×3.

The business world is dynamic, and frameworks, ever important, need to keep pace as well.

A couple of months ago, I was doing an internal lunch & learn for senior managers, and the topic came up as to “how do our VC firms work?”  In the spirit of deeply understanding our customers’ businesses in order to better serve them, I thought the same would be true of our investors and Board members – that educating our team on the inner workings and economics of our investors would lead to greater empathy of one of our other key stakeholders.

So with no small amount of help from my long-time investor and director Brad Feld and his colleague Jason Mendelson, whose book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist I contributed to in a very small way by writing a series of sidebars called “The Entrepreneur’s Perspective” (that process led to my writing Startup CEO), I pulled together this presentation available on Slideshare entitled How Venture Capital Firms Work and Why You Should Care.

I redacted our cap table and pictures of our VCs, but otherwise, feel free to use it with your own management team, or even your whole company.

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

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

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

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

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

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

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

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