Challenging Authority

My dad told me a joke once about a kid who as a teenager thought his father was the dumbest person he’d ever met. But then, as the punchline goes, “By the time I’d graduated college, it was amazing how much the old man had learned.”

The older we get as humans, the more we realize how little we know — and how fallible we are. One of our 13 core values at Return Path gets right to the heart of this one:

We challenge complacency, mediocrity, and decisions that don’t make sense

I will note up front that this particular value statement is probably not as widely practiced as most of the others I’m writing about in this series of posts, but it’s as important as any of the others.

Very few things make me happier at work than when an employee challenges me or another leader — and quite frankly, the more junior and less well I know the employee, the better. No matter what the role, we hire smart, ambitious, and intellectually curious people to work at Return Path. Why let all that raw brainpower go to waste?  We thrive as a company in part because we are all trying to do a better job, and because we work with our eyes open to the things happening around us.

I have no doubt that some real percentage of the decisions that I or other leaders of the company make don’t make sense, either in full or in part. And I’m sure that from time to time we become complacent with things that are running smoothly or quietly, even if they’re not optimal or even moderately destructive.  That’s why I’m particularly grateful when someone calls me out on something. We have made great strides in and changes to the business over the years because someone on the team has challenged something. We’ve terminated employees who were poisonous to the organization, we’ve reversed course on strategic plans, we’ve even sold a business unit.

One of the things we do well is blend this value with one I wrote about a few weeks ago about being kind and respectful to each other.  The two play together very nicely in our culture.  People are generally constructive when they have feedback to give or are challenging authority, and people who receive feedback or challenges assume positive intent and nothing personal.  We specifically train people around these delicate balances both via the Action/Design framework and a specific course we teach called Giving and Receiving Feedback.

It takes courage to challenge authority. But then again, nothing great is ever accomplished in life without courage (and enthusiasm, so the old adage goes).

Size of Pie, a.k.a. What Type of Entrepreneur Are You?

Mmmm…pie.  A post that Fred had up a few weeks ago about an M&A Case study involving WhatCounts, a company in the email space that I’ve known and had a lot of respect for for years, got me thinking about two different topics.  The first is thinking about types of entrepreneurs.  I’ve always said there were two types:  serial entrepreneurs who are great at starting companies but less great at scaling them, and entrepreneurs who are often part of a group of founders but who go on to continue to run the business for the long-haul.

CEO David Geller’s quote that gets to the heart of this in Fred’s post was:

…a bigger piece of a smaller pie, at some point, is the same as a smaller piece of a much larger pie.  And, donʼt let anyone tell you that baking a bigger pie isnʼt a whole lot more difficult.

Although David is talking about taking in outside capital and founder dilution in pursuit of larger business growth and objectives, he is also getting to the same point about entrepreneur type.  Scaling an organization beyond proof of concept, happy few customers, and profitable to be a $50-100mm business (and beyond) requires a whole different skill set than starting something from scratch and turning an idea into reality.

And in a sense, David is right.  Baking a larger pie can be a whole lot more difficult for some entrepreneurs if they are more of the serial entrepreneur type, or at least it can be far less interesting and fulfilling if what gets you out of bed in the morning is creating new things.  But for other entrepreneurs who are more of the “run the business” variety, getting out of the creation phase and into the scaling phase is more interesting and maybe even less difficult.  Even though businesses are never de-risked and a larger business with more employees just means there are more chips on the proverbial table, baking a larger pie and tending to the things that come with it – people issues, innovating within a platform, solving customer problems – can be less daunting than creation for some entrepreneurs.  (Return Path is in its twelfth year – can you guess which kind I am?)

So David’s right in terms of his core point about founder equity value and how large a slice of how large a pie the founder ends up with.  But whether baking a larger pie is easier or harder is less about an inherent difficulty in pie-making and more about the type of entrepreneur involved.

I’ll cover my second reaction to Fred/David’s post next week.

(Post 1 of 4 in the series of Scaling CPO’s)

In most startups, the HR function starts out as tactical, because you have to get people hired and paid, and while you might have a founder or early-stage employee who can do these things, often these tasks are frequently outsourced to a PEO.  As the company grows, it probably in-sources payroll and benefits, hires a recruiter, and maybe has an HR Manager who handles the function. Depending on the number of roles you see being filled, the degree of specialization, or a host of other factors, an in-house team to handle the tactical aspects of HR makes a lot of sense. But at some point you may need to hire a Chief People Officer.

One sign that it’s time to hire a Chief People Officer is if you feel that you’re the driver of company values, that you’re the one talking about values and viewing the company and interactions with that lens—but you’re the only one that cares about the core values. If your HR function is only focused on the tactical aspects of the role and not on how values drive the company, you’ll need to consider a full-time People Officer because focusing on tactical functions only will not help your company scale.

Another sign is if you are spending too much of your own time training managers and leaders or working on interpersonal dynamics on your leadership team. What’s the right amount of time? I think of these tasks (if you’re a a CEO) as things where you should be more like a consultant rather than the driving force behind them. If you find that a large portion of your day or week is filled with people ops activities, it’s time to think about hiring someone.

A third sign that it might be time to hire a People officer can happen when your board asks you what your talent strategy is with respect to improving diversity, retention, and engagement metrics, while simultaneously decreasing average employee salary, and you don’t have a great answer. While it’s acceptable—occasionally—to not know the strategy at a detailed level for a particular part of your business, if you get asked a question by your board and haven’t the faintest idea on how you can get an answer, that ‘s a good sign that you should consider brining in a full-time Chief People Officer.

A fraction Chief People Officer may be a great option, especially if you have a very competent HR manager or director who has strategic inclinations but not enough experience operating as a strategic executive.  If you have a person who just needs a little more supervision in order to “level up” then a fractional executive could be helpful. Or, if you need someone to play more of a consigliere or team coach role to your executive team but don’t want to engage a coach — and your day-to-day HR leader is getting the job done but too junior to facilitate workshops for the senior team, a fractional executive would work. Finally, if you have a very junior HR function or are insourcing it for the first time and need help setting up the whole function from scratch at an advanced size relative to other functions, a fractional executive would be helpful.

As a startup it’s easy to focus on the day-to-day operational details of the People Ops team because those things—payroll, benefits, hiring, onboarding—are tangible and have metrics associated with them. But those things won’t help you scale. If you want to scale your company, if you want to go from $2 million in revenues to $50 million you’ll need to have a person in your organization who is passionate about the values and passionate about helping individual contributors and leaders connect their work to the values. A Chief People Officer will be able to step in and be a leader to the leadership team; after all, companies are built into greatness by people, so this key position is pivotal to the company. 

(You can find this post on the Bolster Blog here)

I wrote a post in 2013 entitled Debunking the Myth of Hiring for Domain Expertise vs. Functional Expertise. In it, I talk about how in hiring senior executives, sometimes you can’t get both functional expertise (great Head of X) and great domain expertise (subject matter expert in X), but that in scaling businesses, there’s another important vector to consider, which is that if your principal business challenge is scaling, then a critical thing to look for in a potential executive is experience with scaling businesses, or at least experience working at businesses of different sizes/stages.

Today’s post is about a fourth vector beyond functional expertise, domain expertise, and scaling expertise: Context, an important vector to consider as well. When I first had this thought, I was having trouble distinguishing it from domain expertise. Now a few months later, I think I am clear on the distinction.

I worked for a while as an interim executive at a company that had giant companies for clients – very, very large companies. Tens and Hundreds of Thousands of employees. And the scope of services we provided was very internal to our clients, meaning our services touch 100% of employees. Early in my career, I worked as a management consultant and did spend the bulk of two years working in very large companies, frequently onsite for several months at a time. Most of my career, though, I have worked in startups/small companies, and while the clients I’ve worked with often included some very large companies, we’ve typically served very small, externally-oriented teams at large companies. So my personal context for this job is somewhat limited.

Why is that relevant? It’s different to work in a small, well lit, high energy, open plan, newly designed urban office than it is to work in a massive footprint office filled with high-wall cubicles and no windows in a suburban office park. It’s different to work in an environment where there are 5+ layers of management between someone and a department head. It’s different to work in a place where career paths are largely vertical (or involve switching business units) as opposed to what I’m used to, which is careers that can Scale Horizontally. And on and on. All these things are important Context for how our clients consume our services. And they’re all different from what I’m used to.

There is no substitute for actually working years on end in large companies, just as there is no substitute for working years in the startup context. Having said that, I think context can be learned about as quickly as subject matter, and about at the same depth.

Why Email Will Win the Day

I attended the same presentation as Fred where a great B2C marketer talked about how she got a 40:1 payback for every dollar spent on email marketing versus an 8:1 payback on search. As head of an email marketing company, it was music to my ears.

But the “finite issue” Fred highlights is actually a great opportunity more than it is a drawback. Most marketers still have email addresses for less than 25% of their full customer database, meaning that if we do our job as an industry, we should be able to increase the availability of email addresses threefold in the coming couple of years. With the inevitable scale efficiencies in email marketing, that 40:1 number can become much bigger, maybe even as high as 100:1, over time.

The challenge for the industry is that this kind of transformation isn’t easy. A lot of the low-hanging fruit of early online adopters is gone. This means marketers are going to have to do more to embrace permission and drive organic list growth if they want to keep pushing the email ROI metric forward. Not necessarily brain bending stuff, but there aren’t a lot of shortcuts for it, either, and it requires a different mindset than traditional advertising and direct marketing. In the end, it all comes down to respecting the consumer and delivering the value exchange to customers.

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!