I used to describe our culture and our employees and our leaders at Return Path as a family.

That was a mistake. It was just plain wrong. It served us well in some respects, but it bit us in the ass on others.

Great groupings of people at work are teams, not families. You can have a highly functional family. But you don’t have high performing families. Work teams need to be high performing.

Here’s what I mean.

The family metaphor worked well at Return Path around the principles of caring for people and lifting each other up. Those elements of a culture are absolutely critical. I don’t regret them for a minute.

But the downside of that metaphor is that families by definition stay families. Sure, spouses can get divorced, but usually not after years of trying to make it work. And kids and parents can’t stop being relatives. Families also don’t typically have metrics and have a structural impetus to improve how they relate to each other, or to some kind of tangible output.

The practical problem with the family metaphor comes down to holding on to people too long when those people aren’t performing well. While I am a big believer that past high performance is both an indicator of future high performance and earns you as an employee a little extra grace when something goes wrong, those things can’t be absolute in business, and they have a clock on them. High performing businesses go the extra mile for their people when their people are going through a rough patch in their lives, and they should be willing to invest in coaching and development when their people need a boost or some kind of corrective action. But not indefinitely.

So even with all the caring and lifting each other up…the family is just the wrong metaphor for a business.

Here’s why the team is the right one, and I’ll use the language of sports teams here a bit more than I normally do.

Teams train together. They have a common goal, which is winning. They know that they are only as good as their weakest link. They have leaders like coaches, managers, GMs, and captains, who they look to for guidance and direction. They are disappointed when they fall short of their goals.

But — and this is the critical learning — the best teams, the highest performing teams in the world, don’t only focus on performance, metrics, and improvement. They care about their people and lift them up. Sure, there are winning teams with tyrannical bosses like the 1970s Yankees. But would you have rather been on one of the George Steinbrenner/Billy Martin teams, or worked for Joe Torre or even Joe Girardi?

The best groupings of people at work are high performing teams…AND they care about each other as people. They just don’t care about each other as people to the detriment of the team, at least not longer than a very brief cure period would allow when something goes sideways.

You can lead your organization to have the orientation of a team, with some of the best elements of families. But not the other way around.

I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject.

Your Leadership Game: “No Comment.”

Should you speak up about news events/ politics?

Most of the time, I say, no!

Startup CEOs feel pressure to speak up on news events: Black Lives Matter, Abortion, LBGTQ+ rights, the conflict in Israel/Palestine, Trump vs. Biden. Many tell me they feel pressured to say something, but are deeply conflicted.

Like you, I am deeply distressed by wars, murder, restrictions on human rights, bias, and hate. But if we feel something, should we say something?

Before you speak up, ask the following questions:

1.      Mission relevance. Is your startup’s success or mission on the line? Are customers or employees directly impacted? Example: It makes sense for Airbnb to advocate when a city tries to ban short-term rentals. It makes sense to advocate for your LBGTQ+ employees when a state tries to restrict their rights.

2.      Moving the needle. Will speaking out change anything? If you “denounce” something or “take a stand,” what really happens? Example: If you have employees in a state banning abortion and you tell them your startup will support them as much as the law allows, this could create great peace of mind for employees. But if your startup does not operate in Ukraine or Russia, then denouncing Russia does little (and Russia does not care!)

3.      Expertise. Do you have a deep understanding of the situation? It’s usually more complicated than it appears, especially at first. Once you speak out, you have painted yourself into a corner you will be forced to defend.

4.      Precedence and equivalence. If you issue a statement about today’s news event, will you react to tomorrow’s event? Why not? Where do you draw the line?Someone will be offended that you spoke up about X but not Y.

5.      Backlash. Are you ready to spend significant time engaging with those who disagree with you?It can get ugly quickly, and mistakes can be costly. Plus, the American public is tiring of business leaders commenting on the news.

6.      Vicarious liability. Who are you speaking for? When you say, “Our startup denounces X”?Does the whole company denounce it? You don’t know, and probably not. Does the Leadership Team? They may feel pressured to support you. What you are really saying is, “I denounce X!” OK, great, then say it to your friends and family. Leave your startup to talk about business.

If your answers are “yes,” – then speak out.

If not, I recommend keeping quiet.

In my opinion, our job is to build great companies, not debate current events.

By not speaking out, you can say, “We don’t talk politics here.” You can shut down any two-sided arguments at work and say, “Let’s get back to work,”removing a big distraction. Remember when employees protested because Google was bidding for Pentagon contracts?

I realize that you will be challenged to make a statement, that, “Saying nothing is unacceptable/ complicit.” But whoever challenges you will only be satisfied if you support their view.

If you still want to speak out, I respect your choice. Some of you will be angry with me for writing this, and I accept that. I’m asking you to think carefully before you make a statement.

This is the third post in the series. The first one When to hire your first CPO is here and What does Great Look Like in a CPO is here).

Chief Privacy Officers who aren’t scaling well past the startup stage are the ones who typically have the following characteristics and you should look for some of these telltale signs.

First, if your Chief Privacy Officer looks at you sideways when you ask for a strategy or even a mitigation plan for a breach, then you might have a bigger problem than the fact that you don’t have a plan.  While we like to talk about things like Privacy by Design and using data protection as an offensive strategic weapon, the reality is that Chief Privacy Officers need to have actionable plans in place at all times for the areas where they judge your company to be the most vulnerable.  If you ask to see the plan or get briefed on it and you get back a blank stare, you know you have a reactive person on your hands for what needs to be a thoughtful proactive role.

Second, you might have a Chief Privacy Officer who is not scaling if they would rather lecture you on GDPR than talk about why your data protection plan will win business.  Privacy people can be geeky, legally-oriented, policy-focused and very technical.  All that is well and good but there is so much more that a great Privacy Officer can do. For example, if your Chief Privacy Officer can’t engage in strategy with you and other executives and understand the levers of your business and how their role can help further them, you may as well use an outside law firm instead of taking up a valuable seat at the table internally.

The Privacy team can be small and somewhat insulated from the business, but your Chief Privacy Officer needs to be able to engage the entire company, they need to be thinking strategically about the business, and they need to have short- and long-term plans in place for contingencies and forseeable roadblocks. If they can’t bring these skills to the table at startup scale, how can they bring them to the table when things really take off?

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

Angry, Defiant, and Replete with Poor Grammar

I didn’t see Bush’s farewell address on TV on Thursday, but Mariquita and I did see his press conference on Monday.  It was exactly what you’d expect it to be and quite frankly just like the last eight years:  angry, defiant, and replete with poor grammar.

I’ve said repeatedly that I think Bush has destroyed the Republican party and will go down in history as one of the worst presidents this country has ever had, if not the worst.  It’s not surprising that his tone at the end is as the title of this post describes.  But it is a shame.  His whole administration is a shame.  The really sad part is that it didn’t have to be.  People make mistakes — even really bad ones.  And they can recover from them and go on to do great things in life if two conditions exist:

1. They solicit feedback on their performance, and

2. The internalize and act on that feedback

Bush not only didn’t “get” these two points; he seemed to revel in them.  “Not paying attention to polls” and “At least you know where I stand” seemed to him to be pillars of strength as opposed to pillars of ignorance and complete and total lack of intellectual curiosity.  You don’t have to try to win a popularity contest to find out when something is going wrong on your watch.  And you can be bold, admit a failure, learn from it, and move on instead of just digging yourself deeper and deeper into the same hole.

I read a great article in The Economist last night that summarized its current view of Bush’s legacy, and in fact it noted a bunch of areas in which Bush appeared to learn from his mistakes, though he probably wouldn’t phrase it that way.  The fact that his second administration did do more to reach out to key allies in Germany and France is one example.  And to the article’s credit, it even noted some of Bush’s accomplishments, or at least the areas in which his thinking was right — those those are just dwarfed in the end by his failings.  

At any rate, I’m delighted he’ll be leaving office on Tuesday.  Inauguration day is one of my favorite days in America, and I look forward with optimism to the incoming administration as I always do, regardless of how I voted.

But as for Bush, I think I’d rather have the pilot of that USAir flight as my commander in chief.  Now there’s a guy (I don’t even know his name, and I probably never will) who had a quick grasp of a difficult situation and produced a brilliant and elegant solution in short order!

Post 4 of 4 in the series of Scaling CMO’s- the other posts are, When to Hire your First Chief Customer Officer, What does Great Look like in a Chief Customer Officer and Signs your Chief Customer Officer isn’t Scaling.

You can engage with each person on the executive team one-on-one to understand what their issues and challenges are, but I’ve found that engaging with the CCO offsite with customers is far more productive and leads to a better understanding of the service organization than any other meeting time. I have typically spent the most time with or gotten the most value out of CCOs over the years doing the following.

In person at “Canary in the Coal Mine” customers. They don’t use canaries any more in coal mines, but the principle applies to companies: What are the early warning signs that you’ve got big problems looming? The earlier you discover those problems the better, and the CCO is usually the first person to figure out that something isn’t right with your product or service. I always find that the largest clients, the most demanding ones, the ones who push you around, the ones who are highly critical or you, are the ones who make your company a better company.  At Return Path, we had those types of clients over the years, from eBay, to DoubleClick, to Microsoft, to Groupon, to Facebook, to Bank of America—and that’s just the short list off the top of my mind.  The demanding customer is the one who breaks things and forces you to own up to your lack of scalability.  They also either take you to task or threaten to pull their business if you don’t clean up your act.  As painful as some of those meetings are, they are also ones I always wanted to attend in person with my CCO, both so I could eat whatever form of crow needed to be eaten as the Chief Crow Eater (which sends a very powerful message to the customer), and also because the CCO and I could experience the chirping of the canary in the coal mine and learn from the experience together.

While it’s important to engage with the CCO in the critical meetings with demanding customers, it’s also important to understand the base.  There’s an old saying from the hardware world that goes, “God was able to create the world in only 7 days because God didn’t have an installed base.”  The new world of Internet technologies, SaaS, and agile development is one where your installed base of customers is your biggest asset, not a millstone around your neck.  Some of the most meaningful experiences I had over the years with our CCOs was to be in market, spending time with all kinds of customers together in small groups and large, deeply understanding their needs and use of our product.

The CCO role is one that is easy to ignore or put on the back burner if things are going smoothly at your company, but as CEO I feel that it is best to stay close to the market and engaging with the CCO with demanding customers and with the base is a good way to understand your company and CCO better.

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

It Never Goes Without Saying

Remember that old adage, "It goes without saying…"?  That saying shouldn’t exist inside a well-run company.  Communication — real communication, not implied communication — is the foundation for a successful business.

We human beings live for "moments."  We mark time by observing regular occasions like birthdays, anniversaries, and holidays.  While religions and cultures differ on the details, we mark the cycle of life with things like baby namings, bar mitzvahs, confirmations, first communions, weddings, and funerals. 

There’s no reason the workplace should be any different.  Think about these few examples where it could "go without saying," but where you’re so much better off creating that "moment" by:

– Publicly acknowledging a member of your team for reaching an employment anniversary (the bigger the number, the heartier the acknowledgment)

– Laying the groundwork for a new initiative by reminding the team in a meeting or email about the company’s mission and how this initiative fits into the big picture

– Marking the end of a project or a transition period with a celebration

– Meeting two weeks after the end of a project or a crisis to do a post-mortem analyzing what went well and defining lessons learned for the next time

– Publicly thanking a colleague for helping out on something — anything

– Giving an employee a quick reprimand or constructive feedback right after an incident (probably privately) instead of letting the issue fester and its details slip from short-term memory

Clear, simple communication is the cheapest and easiest way to create a fun, rewarding, accountable, and focused work environment.

It’s election season, the GOP convention is literally in my backyard, and while this is not a political blog, I can’t help myself. As we as Americans grapple with the question of who we want to be our next leader (or at least those people who live in the 11 annointed swing states do), I have had a lot of thoughts lately about the question of what makes a good leader, and what the differences are between successful leadership in politics and successful leadership in business.

James O’Toole’s article on President Bush on page 31 of the September issue of Fast Company (no link available yet) brings up a really interesting point in comparing Bush to former president Ronald Reagan. He asserts that “what made Reagan effective and respected was that his actions followed consistently from a positive worldview.” (I’d also argue that the positive worldview as a starting point had something to do with it, but that’s beside the point.) He goes on to say that Bush has an “implementation problem” in that he “has vacillated between contradictory approaches to leadership: realism and idealism.” His central thesis is stated very clearly that

“Realists and idealists can both be effective leaders. But one cannot be both at once…The leadership lesson for GW – and for any leader – is simple: Followers don’t much care if leaders are realists or idealists, but they distrust inconsistency.”

This may or may not be true in the political arena, but I know it’s not true in business. Jim Collins’ watershed books Built to Last and Good to Great — both must reads! — describe the ideal CEO as someone who can simultaneously be optimistic and idealistic about the future of the company while simultaneously recognizing and dealing with the realities of the short-term situation. Ironically for this posting, Collins calls this the Stockdale paradox, after retired Admiral James Stockdale, a military leader and erstwhile vice presidential candidate of Ross Perot in the 1992 election.

As CEO, I have to constantly be selling the vision of the company — what we’re trying to become and how we’re going to get there — in broad strokes to my investors, board, management team, employees, and even customers. It’s that vision that keeps the whole machine running and keeps everyone focused and excited and working hard towards our long-term goals. But I have to be equally vigilant about the mundane realities of the current quarter, making our numbers, containing costs, and running the machine. If I did either one without the other, I think the whole system would break down.

Is Bush’s problem, as O’Toole asserts, that he articulated two different types of reasons for the war in Iraq — one rooted in Realism (WMD) and one rooted in Idealism (freedom and democracy)? Same goes for his states reasons for the tax cut — Realism on the one hand (to stimulate the economy) and Idealism on the other hand (shrink government). I agree that the Bush Administration has occasional implementation problems and doesn’t have nearly the “following” that Reagan and other more successful leaders in the past have, but I don’t think they’re caused by combining Realism and Idealism in the President’s leadership style. I think the leader of the free world has to do both well, each at its appropriate time, in order to be effective at his job.

Next up in this series: Admitting Mistakes.

If Only International Relations Were This Easy

Iceland is one of those weird places on earth where two continental plates meet — and you can see it. Here we are, me on the American plate and Mariquita on the Eurasian plate, with the earth seemingly coming apart at the seams in between.

If anyone’s interested in a short travelog to Iceland, here it is.

Retaining good people has always been at the top of my list, even in the dark days.  But hiring and managing in an environment that’s once-stagnant-now-growing presents some real challenges.  Many of these aren’t unique to startups — it’s always tough to find A players — but there are three things I’ve observed that are uniquely tough about hiring in an entrepreneurial environment:

Sometimes It’s Worth Travelling 5,000 Miles for a 5 Minute Meeting

I re-learned this lesson shortly before the holidays.  We’re negotiating a big deal with a company out on the west coast, and we were at a tense and critical spot in the negotiations.  I knew that the only way to move the deal forward to a handshake and a term sheet was to meet face to face with the decision makers on the other side of the table, in person. 

So I got on a plane.  It wasn’t my first choice of activities, and although I was able to work a couple of other meetings into the trip, the trip was a long way to go for a really short meeting.  But it was 100% worthwhile, with a very specific mission accomplished.

As I mentioned in one of my earliest posts, it’s important to be "Present AND Accounted For" in business settings, and with everyone’s busy schedules and increasingly frenzied and multi-tasking office environments, it’s harder than ever to really get someone’s attention.  There’s just no substitute for looking someone in the eye and doing a real handshake, not a virtual one.

Boiling the Frog

We boiled the frog recently at Return Path. 

What the heck does this mean?  There was an old story, I’ve since been told apocryphal, we told a lot back when I was a management consultant trying to work on change management projects.  It was basically that:

If you throw a frog into a pot of boiling water, it will leap right back out.  But if you put a frog in a pot of water on the stove and then heat it up to boiling, you’ll boil the frog because it never quite realized that it’s being cooked until its muscles and brain are slightly too cooked to jump out.

How have we boiled the frog?  Two ways recently.  First, we let a staffing problem sneak up on us.  We were short one person in a critical area (accounting and business operations), and we had decided to try to go without the extra person for a month or two for cost-savings reasons.  Then, another person in that group unexpectedly left.  Then, another person in that group got seriously sick and was out for several weeks.  The result?  We were down three people in an area very quickly, without a proper pipeline of candidates coming in the door for any of the open positions.  So for a period of time, we can’t get the things done out of that group we want to get done, despite the heroic efforts of the remaining people in the group.

Second, we have had an Exchange server problem that has been plaguing one of our three offices for six months now (no, the irony of an email company having internal email problems isn’t lost on us).  In retrospect, the first time we had a big problem with it, we should have dropped everything, brought in an outside consultant, and done a rapid-fire infrastructure upgrade/replacement.  But we were truly boiled here — we kept thinking we’d fixed the problem, the situation kept deteriorating slowly enough to the point where the productivity of this one office was seriously compromised for a few weeks.  Happily, I can report this weekend that our IT team is cuting over to our new environment — "the promised land," as they call it.

How do you stop yourself from getting boiled?  I think you have to:

1. Recognize when you’re in a pot of water.  What areas of your company are so mission critical that they’re always at risk?  Have you done everything you can do to eliminate single points of failure? 

2. Recognize when someone turns on the burner.  Do you know the early-warning signs for all of these areas?  Can you really live without an extra person or two in that department?  Is it ok if that server doesn’t work quite right?

3. Recognize when you care about the frog.  You can’t solve all problems, all of the time.  Figuring out which ones need to be solved urgently vs. eventually vs. never is one of the most important roles a decision-maker in a company can make.