(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 

Clients at Different Levels

Recently, I’ve become more aware that we have a huge range of clients when it comes to the level of the person we interact with at the client organization.  I suppose this has always been true, but it’s struck me much more of late as we’ve really ramped up our client base in the social networking/web 2.0 arena, where most of our clients are CEOs and COOs as opposed to Email Marketing Managers.

Of course, we don’t care who our day-to-day client is, as long as the person is enough of a decision maker and subject matter expert to effectively partner with us, whether it’s on deliverability via Sender Score or on list management or advertising via the Postmaster Network.  There are two main differences I have seen between the levels of client.  I suppose neither one is an earth-shattering revelation in the end, though.

First, the CEO/COO as client tends to be a MUCH MORE ENGAGED and knowledgeable client.  Some of these people know far, far more about the ins and outs of micro details of their businesses (and in the case of deliverability, the micro details of how ISPs filter email) than our average client.  I’d expect this type of client to be in command of the macro details of his or her business, but the level of "in the weeds" knowledge is impressive.  These clients are thirsty for information that goes beyond the scope of our work together.

Second, the CEO/COO as client is MUCH MORE PASSIONATE about his or her business.  It pisses them off when their email doesn’t get delivered.  They care deeply that our Postmaster opt-in might impact their registration rates by 0.5%.  They get very animated in discussions and tend to nod and gesture a lot more than take notes in a notebook.

My main takeaway from this?  If you run a business — how do you make sure your front line people are as fired up as you are?  You may never be able to give people the same kind of macro view you have of the company or the industry (although you can certainly make a good effort at it), but keeping people excited about what they do and igniting their intellectual curiosity on a regular basis will almost certainly lead to more successful outcomes in the details of your company.

Why CEOs Shouldn’t Mess with Engineers

I went to the Vasa Royal Warship Museum in Stockholm the other day, which was amazing – it had a breathtakingly massive 17^th century wooden warship, which had been submerged for over 300 years, nearly intact as its centerpiece.  It’s worth a visit if you’re ever there.

The sad story of its sinking seems to have several potential causes, but one is noteworthy both in terms of engineering and leadership.  The ship set sail in 1628 as the pride of the Swedish navy during a war with Poland.  It was the pride of King Gustavus Adolphus II, who took a keen personal interest in it.  But the ship sank literally minutes after setting sail.

How could that be?  While the king was quick to blame the architect and shipbuilder, later forensics proved both to be mostly blameless.

Likely cause #1:  after the ship was designed and construction was under way, the King overruled the engineers and added much heavier cannons on the upper armament deck.  The ship became top-heavy and much less stable as a result, and while the engineers tried to compensate with more ballast below, it wasn’t enough.

Likely cause #2:  the King cut short the captain’s usual stability testing routines because he wanted to get the ship sailing towards the enemy sooner.

Let’s translate these two causes of failure into Internet-speak.  #1:  In the middle of product development, CEO rewrites the specs (no doubt verbally), overruling the product managers and the engineers, and forces mid-stream changes in code architecture.  #2:  In order to get to market sooner, the CEO orders short-cuts on QA.  I’m sure you’ll agree the results here aren’t likely to be pretty.

So product-oriented leaders everywhere…remember the tale of Gustavus Adolphus and the Vasa Royal Warship and mind the meddling with the engineers!

The Rumors of Email’s Demise Have Been Greatly Exaggerated, Part V

Thank goodness I can finally write a positive piece under this headline, and not a rebuttal like I did here, here, here, and here.

It seems like there are signs of an email marketing renaissance left, right, and center these days.  First, the industry has enjoyed significant growth this year.  Every vendor I speak with in the space except for one or two is posting record numbers — whether they sell data, technology, or services.  And lots of vendors have been swallowed up by larger multi-channel CRM or DM companies for nice prices.  Every marketer or publisher I speak with is investing more money into their email programs, and they are seeing stellar returns.  In fact, their most persistent complaint is that they can’t get enough good names on their lists fast enough.

But beyond those signs, the much-maligned email channel has finally garnered some positive press of late.  First, as, Ellen Byron wrote on November 23 in her Wall Street Journal article entitled “Email Ads Grow Up – Department Stores Discover Devoted Fashion Fans Read Messages in Their Inboxes,” consumers are beginning to much more easily separate spam from commercial email they want, one consumer even going so far as to call emails she receives from retailers “like a quick shopping trip…a guilty pleasure.”

Byron also went on to quantify what some mailers are doing to tilt the balance of their marketing spend ever so slightly in the direction of email.  For example, The Gap is diverting over $26mm that they spent last holiday season on TV towards online and magazine.  And analysts point out that no matter how much marketers spend on their email programs, it’s still a small fraction of what it costs to create and insert a big print or broadcast spot.  I couldn’t even find the full article to link to, but it wouldn’t matter, as you have to be a Journal subscriber to read it (annoying).

And today, email industry guru Bill McCloskey wrote an admittedly self/industry-serving piece about how he is seeing the signs of this email renaissance moving into 2006 as well, starting with the fact that trade associations like the ESPC and the DMA are doing more to step up to the plate in terms of defending and promoting the email channel with the press and consumers.  He also cites the fact that consumers are getting more used to spam and mentally separating out good email from bad email as a reason for the comeback.  Bill even goes so far as to say that “email will surpass search in the battle for marketers’ hearts and minds.”  The full article is here, but warning again, you have to be a Mediapost subscriber to read it (free but still annoying).

It’s nice to see the media tide turning here towards a more rational, balanced position on email.  It’s not just about spam and scams — it’s about the power, customization, and intimacy of the channel!

A Viral Marketing Program That Needs to See a Doctor

I hate sites that make you register in order to read things sent by friends.  What a crappy consumer experience.  If you’re going to make people register to use the site, fine.  But at least allow a small crack in the walled garden for friends to read articles and try your site out.

Today, my friend Len Ellis sent me what looked like a really interesting article in Ad Age via the “send to a friend function.”  When I clicked through the link in the email, it first made me complete a lengthy registration process, including various special offer checkboxes and subscription offers for the magazine and its newsletters.

I went ahead and did this because I was interested in the article.  Then I had to wait for a confirmation email, click on it, and then finally got to see the article.  Except it turns out that what I got to see was the headline and first sentence.  Then Ad Age tole me that in order to read the whole article, I either have to subscribe to the print edition and fill out more forms or pay.  Forget it.  I’ll ask Len to copy the text of the article and send it to me directly.

Why even bother having a “send to a friend” function?

Lighten Up!

As with Brad, I love a good rant, and Dave McClure’s wild one this week about how VCs and Lawyers Need to Simplify, Innovate, and Automate is fantastic.  I have a roughly 3 foot shelf in my office that has all the bound paper documentation for the financings and M&A we’ve done here over the years and have always felt like it’s an enormous waste on many levels.  The insanity of the faxes, zillions of signatures, original copies, and triplicates is overwhelming.

But the core of the rant is a beautiful and simple suggestion that those who invest in lightweight technology companies and automation platforms should learn how to use just those technologies in their own businesses.  I couldn’t agree more, and it reminds me of my least favorite answer EVER from a VC about why some piece of legal documentation had to be done a certain way:  “Because that’s the way we always do it.”  That argument doesn’t even work when a parent uses it on a 5 year old!

I think lawyers are particularly problematic to this cause, because even if an innovative VC wanted to do things easier and differently, the lawyers would probably throw up all over it.  But in the end, if the VC is the client, he or she can and should overrule and manage counsel.  The world is now moving at too quick a pace to keep deal paperwork in the stone ages.

I’m thrilled to announce The Daily Bolster — a quick-hitting podcast for startup leaders scaling their businesses. It’s the actionable insight you need to scale—in about 5 minutes. The first episode drops this coming Monday.

Our team created The Daily Bolster for folks in the startup world who — like me — want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed (which usually ends up sounding like Alvin & The Chipmunks, anyway).

Instead, we’re getting straight to the point. GTTFP, as Brad says.

Starting next week, I will be joined every day by experienced operators and industry experts who share their real-world experiences and practical advice. Each day of the week, we’ll cover a different topic or theme:

• Monday: CEO Tips & Tricks
• Tuesday: Scaling Yourself & Your Team
• Wednesday: The View from the Board Room
• Thursday: Ask Bolster (this one will be more like 20-30 minutes to go deeper with someone)

The schedule is jam-packed with dynamic guests and punchy interviews. Whether you tune in every day, when you see a guest you’re especially interested in, or only on Tuesdays, we’re so excited to share these conversations with you.

In Week 1, I welcome Gainsight CEO Nick Mehta, board member extraordinaire and marketplace guru Cristina Miller, Union Square Ventures partner Fred Wilson, Helpscout CEO Nick Francis, and Bessemer Operating Partner and veteran CFO Jeff Epstein. They’ll share their practical advice and real-world experiences around professional development, company culture, startup strategy, and tips and tricks for executive growth.

Check out the season preview to learn more. You can also sign up for email notifications, to make sure you never miss an episode. The daily email will also include a pull quote and clips in case even the 5-minute version is too long for you.

You can subscribe to The Daily Bolster on these platforms: Bolster, YouTube, Apple, Google, Spotify, Amazon, Stitcher, Pandora, and Castbox, plus we’ll put each episode up on LinkedIn and Twitter. You should either follow me (T, LI) or Bolster (T, LI) on those to see the content.

I help mentor CEOs on executive hiring all the time. One common refrain I hear when we’re talking about requirements for the job is about something I like to call The Mythical Playbook. If I only had the exec with the right playbook, thinks the hiring CEO, all my problems in that executive’s area would be magically solved.

I once hired a senior executive with that same mentality. They had the pedigree. They had taken a similar SaaS company in an adjacent space from $50mm to $250mm in revenue in a sub-group within their functional area. They had killer references who said they were ready to graduate to the C-level job. They had The Playbook! 

Suffice to say, things did not go as planned. I ignored an early sign of trouble, at my own peril. The exec came to me with a new org chart for the department, one with 45 people on it instead of the 20-25 who were currently there. I believed the department was understaffed but was surprised to see the magnitude of the ask. When I pushed back in general, the response I got was “I plan to overspend and overdeliver.” Hmm, ok. I don’t mind that, although a more detailed plan might be useful.  

Then I pushed back on a specific hire, pointing to a box in the org chart with a title that didn’t make sense to me. The response I got was “Yeah, I’m not entirely sure what that person does either, but I know I need that, trust me.” Yikes. 

There are two reasons why The Playbook is mythical. 

The first reason there’s no such thing as a Playbook for executives is that every situation is different. No two companies are identical in terms of offering or culture or structure. Even within the same industry, no two competitive landscapes are the same at different points in time. If life as a senior executive were as simple as following a Playbook, people would make a zillion dollars off publishing Playbooks, and senior executive jobs would be easier to do, and no one would get fired from them.

Now, I’m not saying there isn’t value in analogous experience. There is! But when hiring an executive, you’re not solely looking for someone who claims to know all the answers based on previous experience. That is a recipe for blindly following a pattern that might or might not exist. The value in the analogous experience is in knowing what things worked, sure, but more importantly in knowing when they worked, why they worked, under what conditions they worked, what alternatives were considered, and what things fell apart on the road to success. A Playbook is only useful if it can be applied thoughtfully and flexibly to new situations.

The second reason there’s no such thing as a Playbook when it comes to hiring executives is that the person who might have written the Playbook is actually not available for your job. Most CEOs start a search by saying, “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to you. They have made a ton of money, and they have moved beyond your job in their career progression. What you want is the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people are much harder to find. And when you find them, they don’t have the Playbook. They may have seen a couple chapters of it, but that’s about all.

In the end, the department I referenced above was more successful, but not because of adherence to the new exec’s entire Playbook. The Playbook got the department out over its skis – we overspent, but we did not overdeliver. The new exec ended up leaving the company before they could implement a lot, and that person’s successor ended up refocusing and rightsizing the department. That said, the best thing the department got out of the exec with the Playbook was their successor, which was huge — one element of a strong exec’s Playbook is how to build a machine as opposed to just playing whack-a-mole and solving problems haphazardly.

(Note – I am using the singular they in this and in other posts now, as Brad. Mahendra, and I chose to do in Startup Boards. I don’t love it, but it seems to be becoming the standard for gender neutral writing, plus it helps mask identities as well when I write posts like this.)

OnlyOnce Now MultiLingual

If you look in the left sidebar of OnlyOnce, you will now see a box that says “Translate This Page” with a dropdown that lets you pick the language.  Google Translate takes over from there and does the heavy lifting. 

Global world…awesome service.  Thanks, Google!

Thanks Brad and Ross for the tip.

What Separates Good Teams from Bad Teams?

Every once in a while, I have a conversation that forces me to distill an idea to a sound bite – those frequently become blog posts.  Many happen with members of my team at Return Path, or my friend Matt on our Saturday morning runs, or my Dad or Mom, or Mariquita.  This one happened at dinner the other night with Mariquita and my in-laws Rick and Carmen.

The subject came up about managing a senior team, and different iterations of teams I’ve managed over the years.  And the specific question we posed was “What are the most significant characteristics that separate good teams from bad teams?”  Here’s where the conversation went…“I believe that 100% of the members of good teams can, 100% of the time”

1. Get outside of themselves.  They have no personal agenda, only the best interests of the company, in mind.  They make every effort to see issues on which they disagree from the opposing point of view
2. Understand the difference between fact and opinion.  As my friend Brad says, “The plural of anecdotes is not data.”  And as Winston Churchill said, “Facts are stubborn things.”  If everyone on a team not only understands what is a fact and what is not a fact, AND all team members are naturally curious to understand and root out all the relevant facts of an issue, that’s when the magic happens

Of course there are many other characteristics or checklists of characteristics that separate good teams from bad teams.  But these feel to me like pretty solid ones – at least a good starting point for a conversation around the conference room table.

When a group of us had dinner back in May, Brad posted that it was remarkable that 4 of the 6 people had blogs. Then Amy started a blog, making it 5 of 6. Today, Mariquita and her friend Sharon launched their blog about wine, making it a clean sweep.

There is almost a complete dearth of blog information and commentary about wine. You can tell — the URL she was able to get on Typepad was wine.blogs.com! When Mariquita and I went looking into other wine blogs a couple months ago, all we found were one or two somewhat lame ones, one not updated since February, one not updated since April, none with interesting information that helps average people learn more about how to buy, pair, and enjoy wine.

I think this will be a fun single-topic blog. Enjoy the first posting, and welcome to the blog world, Mariquita and Sharon!