Boards That Lead, by Ram Charan, Dennis Carey, and Michael Useem, was recommended to me by a CEO Coach in the Bolster network, Tim Porthouse, who said he’s been referring it to his clients alongside Startup Boards. I don’t exactly belong in the company of Ram Charan (Brad and Mahendra probably do!), so I was excited to read it. While it’s definitely the “big company” version to Startup Boards, there are some good lessons for startup CEOs and founder to take away from it.

The best part about the book as it relates to ALL boards is the framework of Partner, Take Charge, Stay out of the Way, and Monitor. You can probably lump all potential board activities into these four buckets. If you look at it that way…these are pretty logical:

• Monitor – what you’d expect any board to do
• Stay out of the Way – basic execution/operations
• Partner – strategy, goals, risk, budget, leadership talent development
• Take Charge – CEO hiring/firing, Exec compensation, Ethics, and Board Governance itself.

There was an interesting nugget in the book as well called the Central Idea that I hadn’t seen articulated quite this way before. It’s basically a statement of what the business is and how it’s going to win. It’s about a page long, 8-10 bullet points, and it includes things like mission, strategy, key goals, and key operating pillars that underlie the goals. It basically wraps up all of Lencioni’s key questions in one page with a little more meat on the bones. I like it and may adopt it. The authors put the creation of the Central Idea into the Take Charge bucket, but I’d put it squarely in the Partner bucket.

Other than that, the book is what you’d expect and does have a lot of overlap with the world of startups. Its criteria for director selection are very similar to what we use at Bolster, as is its director evaluation framework. The book has a ton of handy checklists as well, some of which are more applicable than others to startups, for example Dealing with Nonperforming Directors and Spotting a Failing CEO.

All in, a good read if you’re a student of Boards.

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).

• Why I think ClickFraud is far greater than imagined. – Blog Maverick – www.blogmaverick.com _
  Dallas Mavs owner and Internet entrepreneur Mark Cuban on Click Fraud, a notorious member of the Internet Axis of Evil
  (tags: Email Technology Media Marketing)

Chink in the Open Source Armor?

I discovered something by accident yesterday about Firefox (which I love) that is giving me a little pause around the beauty of open source.  Maybe I’m missing something – if I am, please comment.

I went to download some new extensions into Firefox, and the Mozilla site said I had to upgrade to the new version of Firefox (1.0.4) in order to access any extensions.

Before I did the upgrade on my machine, I upgraded my colleague Lisa’s (I was about to show her what extensions were, so I figured it would be best to make a clean start there with 1.0.4).  But once I upgraded her, I discovered that none of the extensions I use in Firefox are compatible with the new 1.0.4 version.

So, I can’t download any new extensions until I upgrade…but I can’t upgrade if I want to keep my existing extensions.  Seems like this is a problem with community-based development, although as my colleague Jack says, “I am surprised FireFox doesn’t build the backwards compatibility since open source extentsions are so important to their business model.”

Deliverability Resources

After my last posting on email deliverability, a few people emailed me to ask about different resources that Return Path has published over the last six months or so on the subject. 

Clicking this link will take you to the white paper download form on our web site, which has all the white papers we’ve written in the past 12 months or so listed, and the most recent one on deliverability pre-checked to get you started.  You can check as many of the boxes you want in one shot, and although the download will trigger an email and/or call from someone in our sales department, you can simply respond to the email and tell them thanks but no thanks if you’re not interested in learning more about our services (of course, you’re also welcome to take the call if you’re interested). 

Anyway, deliverability topics we’ve covered of late which are on this list inclue:

Email Blocking and Filtering Report

Beyond Authentication: Keys to Email Delivery Success

Bonded Sender Increases Email Deliverability by more than 20%

Email Accreditation Programs: What Is All the Buzz About?

Back to the Basics: Deliverability 101 – Getting your email into the inbox

Email Indigestion: How to Avoid Deliverability Failures by Optimizing Your Permission Practices

Email Deliverability Rates Impacted by Time Campaigns Sent

The Secret Role of the Email Address Book…and what it means for your email delivery

How Data Partners Impact Your Email Performance: The checklist for all email aquisition marketers to live by.

Avoiding the Spam Filter Trap

Enjoy!

I attended two offsites in the last two weeks – both great in terms of seeing people in person.  Interesting how differently they handled COVID protocols, although they were different groups with different vibes.

One was a CEO conference for one of my VC’s portfolios.  There was a huge emphasis in all the pre-conference comms about COVID.  And lots of testing.  We all got mailed a very sophisticated in-house PCR test ahead of time to take and photograph/upload, complete with chemical reagents and some kind of centrifuge.  Then those of us who flew in for the event had to do an on-site rapid test before entering the opening reception and even had a side room to sit in for 15 minutes while we were waiting for the rest results.  Once in the room, everyone was super awkward at the beginning.  Should I wear a mask?  Do I shake hands?  Hug?  Wave?  Bump elbows?  But once we got into the flow of the meeting, people were more relaxed and interactive…even some close talking.

The other was my company, Bolster – our first ever “all hands” meeting in person (we started the company just 18 months ago and have people in multiple locations).  The COVID topic was almost nonexistent.  We only have 25 people, and everyone is vaccinated, no one is immuno-compromised, and the couple of people with young and unvaccinated children are very much not on lockdown (that could be more regional – I see that more in NY than in CA).  We simply asked people to get tested before they come on the honor system and then told people when we got there that people should do whatever they were comfortable doing in terms of masks and contact, no judgment.  There was no awkwardness that I could tell at all.

In terms of the meetings themselves, both were great – it was fantastic to be live with other humans!  While there is a lot to be said for the efficiency of 15 and 30 minute meetings on Zoom, that pattern of work can’t be 100% of your year.  It doesn’t allow for serendipitous hallway interactions or highly effective design collaboration like whiteboards and post-its do.

What neither group nailed was blending people actually at the offsite with a few people who didn’t want to, or couldn’t, attend in person.  That’s got to become the norm for offsites going forward, for sure.  Videoconference software or hardware/software combinations need to get better at supporting the hybrid environment for sure, but so do meeting facilitators.

All in, while I’m looking forward to traveling less in the future, there’s much to be said for meeting in person from time to time and figuring out how to optimize that time.

Pret a Manager

My friend James is the GM of the Pret a Manger (a chain of about 250 “everyday luxury” quick service restaurants in the UK and US) at 36th and 5th in Manhattan.  James recently won the President’s Award at Pret for doing an outstanding job opening up a new restaurant.  As part of my ongoing effort to learn and grow as a manager, I thought it would be interesting to spend a day shadowing James and seeing what his operation and management style looked like for a team of two dozen colleagues in a completely different environment than Return Path.  That day was today.  I’ll try to write up the day as combination of observations and learnings applied to our business.  This will be a much longer post than usual.  The title of this post is not a typo – James is “ready to manage.”

1. Team meeting.  The day started at 6:45 a.m. pre-opening with a “team brief” meeting.  The meeting only included half a dozen colleagues who were on hand for the opening, it was a mix of fun and serious, and it ended with three succinct points to remember for the day.  I haven’t done a daily huddle with my team in years, but we do daily stand-ups all across the company in different teams.  The interesting learning, though, is that James leaves the meeting and writes the three points on a whiteboard downstairs near the staff room.  All staff members who come in after the meeting are expected to read the board and internalize the three points (even though they missed the meeting) and are quizzed on them spontaneously during the day.  Key learning:  missing a meeting doesn’t have to mean missing the content of the meeting.

2. Individual 1:1 meeting.  I saw one of these, and it was a mix of a performance review and a development planning session.  It was a little more one-way in communication than ours are, but it did end up having a bunch of back-and-forth.  James’s approach to management is a lot of informal feedback “in the moment,” so this formal check-in contained no surprises for the employee.  The environment was a little challenging for the meeting, since it was in the restaurant (there’s no closed office, and all meetings are done on-site).  The centerpiece of the meeting was a “Start-Stop-Continue” form.  Key learning:  Start-Stop-Continue is a good succinct check-in format.

3. Importance of values.  There were two forms of this that I saw today.  One was a list of 13 key behaviors with an explanation next to each of specific good and bad examples of the behavior.  The behaviors were very clear and were “escalating,” meaning Team Members were expected to practice the first 5-6 of them, Team Leads the first 7-8, Managers the first 10, Head Office staff the first 12, Executives all 13 (roughly).  The second was this “Pret Recipe,” as posted on the public message board (see picture below).  Note – just like our values at Return Path, it all starts with the employee.  One interesting nugget I got from speaking to a relatively new employee who had just joined at the entry level after being recruited from a prominent fast food chain where he had been a store general manager was “Pret really believes this stuff — no lip service.”

I saw the values in action in two different ways.  The first was on the message board, where each element of the Pret Recipe was broken out with a list of supporting documents below it, per the below photo.  Very visual, very clear.

The second was that in James’s team meeting and in his 1:1 meeting, he consistently referenced the behaviors.  Key learning:  having values is great, making them come to life and be relevant for a team day-in, day-out is a lot harder but quite powerful when you get it right.

4. Managing by checklist.  I wrote about this topic a while ago here, but there is nothing like food service retail to demand this kind of attention to detail.  Wow.  They have checklists and standards for everything.  Adherence to standards is what keeps the place humming.  Key learning:  it feels like we have ~1% of the documentation of job processes that Pret does, and I’m thinking that as we get bigger and have people in more and more locations doing the same job, a little more documentation is probably in order to ensure consistency of delivery.

5. Extreme team-based and individual incentive compensation.  Team members start at $9/hour (22% above minimum wage that most competitors offer).  However, any week in which any individual store passes a Mystery Shopper test, the entire staff receives an incremental $2/hour for the whole week.  Any particular employee who is called out for outstanding service during a Mystery Shop receives a $100 bonus, or a $200 bonus if the store also passes the test.  The way the math works out, an entry level employee who gets the maximum bonus earns a 100% bonus for that week.  But the extra $2/hour per team member for a week seemed to be a powerful incentive across the board.  Key learning: team-based incentive comp is something we use here for executives, but maybe it’s worth considering for other teams as well.

6. Integrated systems.  Pret has basically one single software system that runs the whole business from inventory to labor scheduling to finances.  All data flows through it directly from point of sale or via manager single-entry.  All reports are available on demand.  The system is pretty slick.  There doesn’t seem to be much use of side systems and side spreadsheets, though I’m sure there are some.  Key learning: there’s a lot to be said for having a little more information standardized across the business, though the flip side is that this system is a single point of failure and also much less flexible than what we have.

7. Think time.  I’ve written a little about working “on the business, not in the business,” or what I call OTB time, once before, and I have another post queued up for later this summer about the same.  Brad Feld also very kindly wrote about it in reference to Return Path last week.  Working in retail means that time to work on IMPORTANT BUT NOT URGENT issues is extremely hard to come by and fragmented.  I suspect that it comes more at the end of the day for James, and it probably comes a lot more when he doesn’t have someone like me observing him and asking him questions.  But his “office” (below), exposed to the loud music and sounds and smells of the kitchen, certainly doesn’t lend itself to think time!  Key learning:  of course customers come first, but boy is it critical to make space to work OTB, not just ITB.  Oh, and James needs a new chair that’s more ergonomically compatible with his high countertop desk.

Years ago, I spent a few weekends working in my cousin Michael’s wine store in Hudson, NY, and I wrote up the experience in two different posts on this blog, the first one about the similarities between running a 2-person company and a 200-person company, and the second one about how in a small business, you have to wear one of every kind of hat there is.  My conclusion then was that there are more similarities than differences when it comes to running businesses of different types.  My conclusion from today is exactly the same, though the focus on management made for a very different experience.

Thanks to James, Gustavo, Orlanda, Shawona, and the rest of the team at the 36th & 5th Pret for putting up with the distraction of me for the bulk of the day today — I learned a lot (and particularly enjoyed the NYC Meatball Hot Wrap) and now have to figure out how to return the favor to you!

(This is the second in a series of three posts on this topic.)

In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them.

Selecting a CEO Mentor is literally like selecting a teacher but at a vocational school, not at a research university.  You want to select someone who has done something several times or for several years; done it really well; documented it in some organized way (at least mentally); and can articulate what they did, why, what worked and what didn’t, and help you apply it to your situation.  Do you want to be taught how to be an electrician by someone with a PhD in Electrical Engineering, or by someone who has been a master electrician for 20 years?   Fit matters mostly around values.  It’s hard to get advice from someone whose values are quite different, as their experiences and their metrics for what did and didn’t work won’t apply well to yours.  Fit is a lot less around personality, although you have to be able to get along and communicate with the person at a basic level  Find someone with the right experience set that you can learn from RIGHT NOW.  Or at least this year.  Maybe the person is the right mentor next year, maybe not.  Depends on what you need.  For example, if you’re running a $10mm revenue DTC company, find someone who has scaled a company in the DTC or adjacent eCommerce space to at least $25-50mm. 

Although I’ve been very international in getting mentoring as a CEO over the years, I’ve never hired a formal CEO Mentor. Several people, from my dad to my independent directors to the members of my CEO Forum have played that role for me at different times over the years. Knowing what I know now, I’m working with CEO Mentors who have experience with talent marketplaces at different scale, since this is a new industry for me.

Selecting a CEO Coach is different.  I got lucky in my selection of a CEO Coach almost 20 years ago.  My board member Fred Wilson told me I needed to work with one, I naively rolled my eyes and said ok, he introduced me to Marc Maltz, I told Marc something like “I need a coach because clearly I need to learn how to manage my Board better,” and for some reason, he decided to take the assignment.  I got lucky because Marc ended up being exactly the right coach for me, going on 20 years now, but I didn’t know that at the time.  

Selecting a CEO Coach is all about who you “click with” personality wise, and what you need in order to be pushed to grow developmentally.  CEO Coaches come on a spectrum ranging from what I would call “Quasi-Psychiatrist” on one end, to “Quasi-Management Consultant” on the other end.  The former can be incredibly helpful — just note that you will find yourself talking about your thoughts, feelings, and family of origin a fair bit as a means of uncovering problems and solutions.  The latter can be helpful as well — just note that you will find yourself talking about business strategy and having someone hold up the proverbial mirror so you can see you the way other people see you as the CEO, quite a bit.  There is no right or wrong universal answer here to what makes someone the right choice for you.  For me, if one end of the spectrum is a 1 and the other is a 5, I prefer working with people who are in the 3-4 range.  

Therapy and coaching are different, though.  A good CEO Coach who is a 1 will refer clients to therapy if they see the need. While coaching can “feel” therapeutic, and actually may be therapeutic, it is not a replacement for therapy. The differences between the 1s and the 5s are not just style differences but also really what you want the content of the coaching to be.  A 1 is going to help you discover and drive to your leadership style.  A 5 is going to help you align those decisions to how you actually act, what approaches you bring to the organization and how you address challenges.  Some CEO Coaches can move back and forth between all of these, but knowing where you sit with your needs relative to the coach’s natural style when you pick a coach is critical.

I know CEOs who have shown tremendous growth as humans and leaders with Coaches who are 1s and Coaches who are 5s.  A good CEO Coach is someone you can work with literally forever.   

I always encourage CEOs to interview multiple Coaches and specifically ask them what their coaching process is like and what their coaching philosophy is.  How do they typically start engagements.  How structured or unstructured are they in their work?  Check references and ask some of their other CEO clients what it’s been like to work with them.  This is all true to a much lesser extent with Mentors.  In both cases, you should probably do a test session or two before signing up for a longer-term engagement.  You wouldn’t buy a car without taking it for a test drive.  This is an even more consequential decision.  

And in both cases, there should be no ego in the process.  You should never feel like you’re being sold by a CEO Coach or CEO Mentor.  And they shouldn’t feel hurt by you picking someone else, either.  Alignment and chemistry are so critical – there is no way to have that with every person, and the good professionals in this industry should know that.

The bottom line is that hiring a CEO Mentor is low risk. If it’s not working out, you stop engaging. Hiring a CEO Coach is a longer-term decision, and it’s worth having couple of sessions with a coach before making the commitment.

Next post in the series coming:  How to get the most out of working with a CEO Mentor or CEO Coach 

(This is the second post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Introductory post is here.)

Tuesday, March 17, Day 1

• Extended stay hotel does not have a gym.  Hopefully there is one at work
• Walking into office for the first time.  We are in a government building in a random town just south of Denver that houses the State Emergency Operations Center (SEOC) and the Department of Homeland Security and Emergency Management.  These are the teams who are on point for emergency response in Colorado when there is any kind of fire, flood, cyberattack, or other emergency
• 
• 
• MAJOR Imposter Syndrome – I don’t know anything about anything
• 7:45 meeting with Stan
• 8:15 department briefing
• Met two deputies – Kacey Wulff and Kyle Brown.  Both seem awesome. On loan from governor’s health care office and insurance department
• Team “get to know you” was 4 minutes long.  So different than calm normal 
• Emergency Operations Center in Department of Public Health
• Small open room with over 100 people in it and everyone freaking out about not following best practices – no social distancing
• 
• Leader giving remote guidelines
• Lots of “Sorry, who are you and why are you here?”
• Local ops leader Mike Willis excellent – calm, inspirational, critical messages around teamwork, self-management, check ego at the door (turns out he is a retired Brigadier General)
• HHS call – maxxed at 300 participants, people not getting through, leader had to ask people to volunteer to get off the line (oops)
• Lunch and snacks in mass quantities here – it’s not quite Google, but this part does feel very startup.  I wonder if the Emergency Ops Center does this all the time or just in a crisis. Guessing crisis only but still super nice.  Also guessing I will gain weight this week between this and all gyms in the state being closed down
• Lots of new people and acronyms
• Multiple agencies at multiple layers of government require a lot of coordination and leadership that’s not always there, but everyone was incredibly clear, effective, low ego.  A lot of overlap
• Got my official badge – fancy
• Jared calls – just spoke to Pence, his guy is going to call you – tell him what we need…”uh, ok, now all I have to do is figure out what we need!”
• Fog of War – this room is healthy and bustling and a little disconnected from what’s going on, no freak out
• Kacey and call from Lisa about Seattle being on “Critical Care” because they don’t have enough supplies, meaning they are prepared to let the sickest people die – oh shit, we can’t let that happen here (or is it too late?)
• Got oriented, sort of
• Slight orientation to broader command structure and team
• My charter and structure are a little fuzzy, guess that’s why I’m here to figure that out
• Late night working back at hotel.  Thinking I will become a power user of UberEats this week

Wednesday, March 18, Day 2

• Gym at work is closed along with all gyms everywhere.  Looks like a lot of hotel floor exercises are in order
• Ideas and efforts and volunteers coming in like mad and random from the private sector – no one to corral, some are good, some are duplicative, all are well intentioned.  Lots of “solve the problem 5 ways”
• Shelter in place?  Every day saves thousands of lives in the model – credibility with governor
• State-level work is so inefficient for global and national problems, but Trump said “every man for himself” basically when it comes to states
• Not feeling productive
• Productivity is in the eye of the beholder.  Kacey totally calmed me down. Said I am adding value in ways I don’t think about (not sure if she was just being nice!):
  • Connection to Governor really useful for crisis team
  • Basic management and leadership stuff good
  • Asking dumb questions
  • Out of the box thinking
  • Liaison to industry and understanding that ecosystem
  • Arms and legs
  • People used to working in teams on things – different expectations in general
• Ok, so maybe I am helping
• Colleague tells me about Drizly, the UberEats equivalent for alcohol delivery. Good discovery.

Thursday, March 19, Day 3

• Weird – my back feels better than it has in months.  Maybe it’s the pilates, but still, seems weird.  I wonder if the higher altitude helps. If so, we will be moving to Nepal. Have to remember to mention that to family later
• Governor Policy meeting 9 am – “Cuomo is killing it” – words matter – “shelter in place” and “extreme social distancing” debate
• “The models are wrong – so let’s average them”
• We need 10,000 ventilators. We have 700.  Uh oh.
• Raised issues around test types and team capacity…Gov expanded scope to include app and still pushing hard on test scaling.  Gov asked for proposal for expanded scope and staff by 4:30. Guess that’s the day today!
• Recruited Brad to lead Private Sector side of the IRT’s work. Important to have a great counterpart on that side. Glad he agreed to do it, even though he’s already vice chair of another state task force on Economic Recovery
• Senior Ops leader interrupts someone during daily briefing – quietly says to the whole room “not vetted, not integrated, not helpful” – incredible.  In the moment, in public which normally you don’t want to do but had no choice in this circumstance – 6 words gave actionable and gentle feedback. Great example of quiet leadership
• Private sector inbound – well intentioned and innovative but overwhelming and hard to figure out how to fit in with public sector (e.g., financing to spin up distributed manufacturing)
• Team huddled and created proposal for new name, structure, staffing, charter, rationale, etc.
• Present to senior EOC staff for vetting, feedback
• Feels like I’m adding value finally – plan creation and “bring stakeholders along for the ride” presentation/vetting AND getting the team to stop being hair on fire and focus on thinking and planning and staffing
• Present to Gov – “brilliant” – then after, Kyle says “I’ve worked for multiple governors and senators, and this is the first time I’ve heard something called brilliant” (not sure it was brilliant)
• Now to operationalize it, stand up a team, replace myself so I can get home once this is marching in the right direction at the right speed
• Transferable skills (leadership, comms, strategy, planning) – not just missing context here but missing triple context – healthcare, public sector, CO
• Day 3.  Feels like longer
• Still, feels like adding value now.  Whew.  
• Dinner with a Return Path friend who came down to my hotel’s breakfast room, picked up takeout on the way, and sat 6 feet apart. 

Stay tuned for more tomorrow…

In Search of Automated Relevance

A bunch of us had a free form meeting last week that started out as an Email Summit focused on protocols and ended up, as Brad put it, with us rolling around in the mud of a much broader and amorphous Messaging Summit.  The participants (and some of their posts on the subject) in addition to me were Fred Wilson (pre, post), Brad Feld,  Phil Hollows, Tom Evslin (pre, post), and Jeff Pulver (pre, post).  And the discussion to some extent was inspired by and commented on Saul Hansell’s article in the New York Times about “Inbox 2.0” and how Yahoo, Google, and others are trying to make email a more relevant application in today’s world; and Chad Lorenz’s article in Slate called “The Death of Email” (this must be the 923rd article with that headline in the last 36 months) which talks about how email is transitioning to a key part of the online communications mix instead of the epicenter of online communications.

Ok, phew, that’s all the background. 

With everyone else’s commentary on this subject already logged, most of which I agree with, I’ll add a different $0.02.  The buzzword of the day in email marketing is “relevance.”  So why can’t anyone figure out how to make an email client, or any messaging platform for that matter, that starts with that as the premise, even for 1:1 communications?  I think about messaging relevance from two perspectives:  the content, and the channel.

Content.  In terms of the content of a message, I think of relevance as the combination of Relationship and Context.  The relationship is all about my connection to you.  Are you a friend, a friend of a friend, or someone I don’t know that’s trying to burrow your way onto my agenda for the day?  Are you a business that I know and trust, are you a carefully screened and targeted offer coming from an affiliate of a business I trust, or are you a spammer? 

But as important as the relationship is to the relevance of your message to me, the context is equally important.  Let’s take Brad as an example.  I know him in two distinct contexts:  as one of my venture investors, and as an occasional running partner.  A message from Brad (a trusted relationship) means very different things to me depending on its context.  One might be much more relevant than the other at any moment in my life.

Channel.  The channel through which I send or receive a message has an increasing amount to do with relevance as well.  As with content, I think of channel relevance as the combination of two things –  device, and technology.  For me, the device is limited to three things, two with heavy overlap.  The first is a fixed phone line – work or home (I still think cell service in this country leaves a lot to be desired).  The second is a mobile device, which could mean voice but could also mean data.  The third is a computer, whether desktop or laptop.  In terms of technology, the list is growing by the day.  Voice call, email, IM, Skype, text message, social network messaging, and on and on.

So what  do I mean about channel relevance?  Sometimes, I want to send a message by email from my smartphone.  Sometimes I want to send a text message.  Sometimes I want to make a phone call or just leave a voicemail.  Sometimes I even want to blog or Twitter.  I have yet to desire to send a message in Facebook, but I do sometimes via LinkedIn, so I’m sure I’ll get there.  Same goes for the receiving side.  Sometimes I want to read an email on my handheld.  Sometimes a text message does the job, etc.  Which channel and device I am interested in depends to some extent on the content of the message, per above, but sometimes it depends on what I’m doing and where I am.

So what?  Starting to feel complex?  It should be.  It is.  We all adjusted nicely when we added email to our lives 10 years ago.  It added some communication overhead, but it took the place of some long form paper letters and some phone calls as well.  Now that we seem to be adding new messaging channels every couple weeks, it’s becoming increasingly difficult to get the relevance right.  Overlaying Content (Relationship and Context) with Channel (Device and Technology) creates a matrix that’s very difficult to navigate.

How do we get to a better place?  Technology has to step in and save the day here.  One of the big conclusions from our meeting was that no users care about or even know about the protocol – they just care about the client they interact with.  Where’s the ultra flexible client that allows me to combine all these different channels, on different devices?  Not a one-size-fits-all unified messaging service, but something that I can direct as I see fit?  There are glimmers of hope out there – Gmail integrating IM and email…Simulscribe letting me read my voicemail as an email…Twitter allowing me to input via email, SMS, or web…even good old eFax emailing me a fax – but these just deal with two or three cells in an n-dimensional matrix.

As our CTO Andy Sautins says, software can do anything if it’s designed thoughtfully and if you have enough talent and time to write and test it.  So I believe this “messaging client panacea” could exist if someone put his or her mind to it.  One of the big questions I have about this software is whether or not relevance can be automated, to borrow a phrase from Stephanie Miller, our head of consulting.  Sure, there is a ton of data to mine – but is there ever enough?  Can a piece of software figure out on its own that I want to get a message from Brad about “running” (whatever channel it comes in on) as a text message on my smartphone if we’re talking about running together the next day, but otherwise as an RSS feed in the same folder as the posts from his running blog, but a voicemail from Brad about “running the company” (again, regardless of how he sends it) as an email automatically sorted to the top of my inbox?  Or do I have to undertake an unmanageable amount of preference setting to get the software to behave the way I want it to behave?  And oh by the way, should Brad have any say over how I receive the message, or do I have all the control?  And does the latter question depend on whether Brad is a person or a company?

What does this mean for marketers?  That’s the $64,000 question.  I’m not sure if truly Automated Relevance is even an option today, but marketers can do their best to optimize all four components of my relevance equation:  content via relationship and context, and channel via device and technology.  A cocktail of permission, deep behavioral analysis, segmentation, smart targeting, and a simple but robust preference center probably gets you close enough.  Better software that works across channels with built-in analytics – and a properly sized and whip smart marketing team – should get you the rest of the way there.  But technology and practices are both a ways off from truly automated relevance today.

I hope this hasn’t been too much rolling around in the mud for you.  All thoughts and comments (into my fancy new commenting system, Intense Debate) are welcome!

An Undignified End to an Internet Pioneer

I was one of Wingspan Bank’s first customers when they opened their online banking system as a division of Bank One back in 1997 or so.  Wingspan closed its doors and merged with Bank One probably about 6 years ago now, with (if I remember correctly) only 77,000 customers — obviously, the world had changed a lot, and online banking no longer required a dedicated “online bank.”

Even after Wingspan closed, I kept my Wingspan-turned-Bank One account, although there wasn’t much money in it and I didn’t really use it for much of anything.  Finally, last week, I decided to close the account — easy, I figured, since Bank One had merged with Chase, which is where we have our main savings and checking accounts.

Well, after three phone calls and one fax, the conclusion was that there was no way to automatically merge the Bank One and Chase accounts or even electronically transfer the funds from one to the other as part of the same bank (hello, merger integration?).  So in the end, my big experimental Wingspan online banking account drew to a close with a paper check mailed to me so I could re-deposit it at Chase.  Even for a connoisseur of irony, that seemed like a bit much to me.