Fred Wilson has a great posting today about how as a VC, it’s important to tell CEOs the truth when you don’t fund them so they can learn from the experience. As someone who’s been dinged by his share of VC’s (although not yet by Fred), I completely agree. He drew a great comparison to a conversation he had with a woman on an airplane about telling someone she didn’t want to go on a second date with him.

I’ve always felt that as a manager, firing someone is a lot like breaking up with a significant other. As the song says, Breaking Up is Hard to Do! This is particularly true when the person is either a long-time employee or is someone you have to lay-off, where the termination is not his or her fault.

When I think back to the first time I ever had to fire a person while I was at MovieFone, I remember it as one of the most horrific experiences of my life. Not to be glib about it, but I think it was harder on me than it was on her (and it was a lay-up – she was being fired for cause!).

Anyway, for an empathetic person, it is hard to look people in the eye and tell them they don’t have a job any more, whatever the reason. And I also think that people are generally well-served, even if they don’t think about it that way at the time, if they can understand why they’re being let go so they can continue to constructively develop their careers going forward and seek out jobs for which they might be a better fit.

Of course, in a non-layoff situation, someone being terminated should know why they’re being fired because a good manager would have coached them and given them appropriate warnings and conversations along the way, but that’s the subject of another posting.

RSS and Email’s Demise, Continued

Thanks to my colleague Tom Bartel, I discovered two good postings this week that I thought I’d pass on.

The first one by Ed Brill talks about Email vs. RSS and is a great contribution to the debate. It has some similar thoughts to my original posting about Prepping RSS for Prime Time.

The second one by Christopher Knight is entitled 22 Reasons Why Email Is Not Dead and is a great contribution to the dialog I contributed to in my Rumors of Email’s Demise posting a while back.

Counter Cliche:  Don’t Just Do Something, Stand There

Fred had a great posting the other day about Analysis Paralysis.  And he’s right, a lot of the time.  But I’ve always thought that Newton’s third law of motion can be applied to cliches — that every cliche has an equal and opposite cliche (think “Out of Sight, Out of Mind” vs. “Absence Makes the Heart Grow Fonder”).

The counter cliche to Analysis Paralysis is “Don’t Just Do Something, Stand There” — another great lesson taught to me by my old boss at MovieFone.  While startup businesses generally do need to move quickly and nimbly, there are times and places, particularly when negotiating something, where stopping or moving very slowly works to your advantage.  This can be true in any situation — hiring someone, working on a strategic partnership, acquiring a company or selling your own company, and yes, on occasion, even in closing business with a client.

Slowing down or stopping a negotiation helps you accomplish two critical things to achieving an optimal result:

1. It allows you to gain a little perspective on what you’re negotiating and consider other alternatives.  It’s easy to get caught up in the heat of a negotiation.  While that negotiating process can be addictive, you always want to make sure you really want what you’re going after and that you’ve taken every step you can to shore up your alternatives.

2. It lets you see how important the deal is to the other party.  If you change the pace of a negotiation, you can more easily see how the other party responds to that change of pace.  Do they fade away, or do they keep calling and pressing for forward movement?

There’s a time and a place for everything in a startup.  Sometimes it’s to run hard, but sometimes it’s to stand still.

Fred’s VC Cliche of the Week this week is called "the pass," which is the euphemism that VCs have adopted when they decide not to invest in a particular company or entrepreneur.  Fred’s VC wisdom comes down to this:

1 – Say no quickly to the things you know you aren’t going to do

2 – Don’t take an opportunity into diligence unless you are willing to spend enough time to truly  undersand it, and if you don’t invest, make sure you are willing to spend time explaining why.

It won’t make it any easier on the entrepreneur who is trying to find someone to invest in his business that you are passing, but they might learn something from the discussion, and in the end you will gain their respect.

And in this age where VCs and their money are a dime a dozen and great entrepreneurs are rare, respect from entrepreneurs is critical to success in the VC business.

The counter cliche is that the same advice applies to entrepreneurs who "pass" on a particular VC.  There are many times where startups (especially good ones) have offers on the table or are pursuing them from multiple VCs.  That strategy is a must and one that I’ve blogged about before. 

VCs may be a dime a dozen, but great ones are hard to find.  If you find yourself in the position of having to "pass" on one of them — follow Fred’s advice and do it quickly, politely, and without wasting any more of their time.

Just Say No

A recent study by AOL (published here in CNET) says that on average, people in America check email five times per day and can’t go without it for more than three days at a time.  And six out of ten respondents said they check email on vacation.

While I’m as guilty as anyone of perpetuating these statistics, I am a big fan of taking regular time off from email.  Whether it’s a day each week, or a whole weekend here or there, or at least one week vacation per year, it’s important to Just Say No every once in a while.  Even Fred took an email holiday recently, to great success, I believe.  The great thing about email is that they’ll all be there waiting for you when you log back in.

My 360 on Your 360

Last year, I wrote about the 360 review process we do at Return Path, which is a great annual check-in on staff development and leadership/management.  In Part I of What a View, I described the overall process.  In Part II, I talked specifically about how my review as CEO worked, which is a little different.

This year, we changed the format of our reviews in two ways. First, for senior staff, we continued to do the live, moderated discussions, but we dropped having people also fill out the online review form.  It was duplicative, and the process already consumes enough time that we decided to cut that part out, which I think worked well. 

Second, for my review, instead of having the Board review me separately from the senior staff, I combined efforts and had all of them participate in my live moderated discussion together.  I also think this worked well, although we did receive some feedback about how to modify the format slightly for next year.  It was great for the Board to get a window into how the team feels about me, and vice versa, and it produced a single, unified development plan for me, which is much more helpful than two sets of feedback about different questions and issues.

The one theme that came out of this year’s live reviews, which is definitely worth thinking about, is the impact of the Heisenberg Uncertainty Principle, that once something is observed, the act of observing it can actually change it.  Because the live discussions are face to face (anonymous to the person being reviewed, but not anonymous among the reviewers), some people mentioned that they were conscious of what they were saying in the presence of others in the company.  Others didn’t particularly care about that but did say things that could be construed as negative about some of their fellow reviewers.  Someone came up to me after one session and said "I wonder what the rest of the group thought of my comments — I need a 360 on your 360!"

The reality is that transparency is a good thing.  There shouldn’t be any state secrets about someone’s performance, especially when the person is in a senior management position.  All people always have things they can improve upon, and the open discussion around what they are and why they happen produce MUCH better results for the people being reviewed, uncomfortable as it may be at times.

The sessions are confidential, so participants should feel comfortable that their thoughts won’t be shared outside the room.  Plus, we provide a mechanism to give feedback that really is hard to provide in public for whatever reason via email or one-on-one conversations with the moderator.

Another Entrepreneur Blog

My friend Jason Devitt, founder and CEO of mobile application company Vindigo, is contemplating his next career move and has started to blog more actively about entrepreneurship (after a 9-month around-the-world honeymoon which made for a great travel blog).

His most recent post is about what it takes to be an entrepreneur, which I thought was great, and he promises more good ones on related topics to come soon.

A Thankful Moment

While there are certainly some aspects of being a CEO that are full of those proverbial thankless tasks…there are some moments that are just the opposite.  And boy are those rewarding.

I had one this morning.  While I frequently get nice emails or handwritten cards from employees after they interview or start or get a promotion or raise — and those are all great — this is one I can easily blog about because it’s online.

Yesterday was the first official day of work for Neil Schwartzman, who actually joined us many months ago as a consultant running compliance for our Sender Score Certified whitelist but just finally became a full-time employee as we set up a Canadian entity and International entity and whatever our lawyers and accountants told us we had to do in order to be legit about hiring out of the country.

Neil’s thank you post is very entertaining (I promise, our objective isn’t to have employees drinking and slacking off!), but more than that, rewarding in that he says we do a good job at Return Path of walking the walk around ethics, reputation, and high standards in what we do for the email ecosystem.  Now that’s rewarding.

But in some ways, it’s even more meaningful coming from Neil.  Just as he says he took a risk in coming to work with us, we took a risk in bringing him on board.  As a leading voice in the anti-spam community, Neil is exactly the kind of person that spooks out some of our clients who think of anti-spammers as the enemy.  Our view is, as you can imagine, more nuanced.  Anti-spammers who do their job well are a legitimate marketer’s best friend because they are keeping the inbox clean of actual spam.  As we tell our clients, we are a big tent here — the only way we will solve our clients’ deliverability problems is by working WITH the receivers of the world on common language, rules, standards, and metrics — not working AGAINST them.  And that’s where Neil has done such a great job for us so far — bringing his unique perspective on the spam problem and working alongside many others on our deliverability team like Tom Bartel, Tom Sather, Leslie Price, Melinda Plemel to help keep the world safe for email.

So thanks, Neil…and right back at you!

Advisory Boards

This is a topic that’s come up a fair amount lately here. Advisory Boards can be great sources of help for entrepreneurs. They can also be great things to participate in. Here are a handful of quick tips for both sides of the equation.

If you are building an advisory board:

– Figure out what kind of Advisory Board you want to build — is it one that functions as a group, or is it one that’s a collection of individual advisers, and a Board in name only?

– Clarify the mission, role, and expected time required from advisers on paper, both for yourself and for people you ask

– Be prepared to pay for people’s time somehow (see below)

– Figure out the types of people you want on your Advisory Board up front, as well as a couple candidates for each “slot.” For example, you may want one financial adviser, one industry adviser, one seasoned CEO to act as a mentor or coach, and one technical adviser

– Aim high. Ask the absolute best person you can get introduced to for each slot. People will be flattered to be asked. Many will say yes. The worst they will do is say no and refer you to others who might be similarly helpful (if you ask for it)

– Work your Advisory Board up to the expectation you set for them.  Make sure you include them enough in company communications and documents so they are up to speed and can be helpful when you need them.  Treat them as much like a Board of Directors as you can

If you are asked to serve on an advisory board:

– Make sure you are interested in the subject matter of the company, or

– That you have a good reason to want to spend time with the entrepreneur or the other Advisory Board members for other reasons, and

– Don’t be afraid to say no if these conditions aren’t met (it’s your time, no reason to be too altruistic)

– Clarify up front the time commitment

– Try to get some form of compensation for your effort, whether a modest option grant (size totally depends on the time commitment), or the ability to invest in the company

– Be sure to let your employer know. Ask for permission if the business you’re advising is at all related to your company, and get the permission in writing for your HR file

– Follow through on your commitment to the entrepreneur, and resign from the Advisory Board if you can’t

Those are some initial thoughts — any others out there?

Feeling Less Like a Luddite:  Welcome, Meebo!

As I’ve written about on occasion (here, here), it’s easy to feel like a Luddite with the rapid pace of change of the web these days.  Anyway, I’m feeling slightly less like one today with the addition of Meebo to my blog.

I read about Meebo in David Kirkpatrick’s Fast Forward column last week, and it was such a cool idea, I had to install it right away.  Basically, it adds a widget to the right sidebar of my blog which allows readers to Instant Message me any time I’m online if they’re reading my blog (anonymously, I think, and regardless of whether or not they have a Meebo account, although I needed to create one in order to install it on OnlyOnce).

Having a Meebo account is also basically like having a web-based version of Trillian, so I can get on IM from any computer with a browser at any time.

Should be an interesting way to hear more from readers.  We’ll see.  Meebo Me!

The Business of Being a Scumbag

I’ve written a couple of times about what Fred calls the Internet’s Axis of Evil.  But David Kirkpatrick from Fortune just blew me away yesterday with his lurid description of the Internet’s crime scene.  This is a must-read for anyone who works in the online medium.