I have an end of year work routine that’s a pull-up and self-assessment. I’ve been doing this for years, and I’ve written about its evolution in Part I and Part II of this series.

I’ve always taken a few minutes at this time of the year to ask myself these four questions:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

If I answer at least 2.5 of these questions as yes, I feel like things are on track. If I am below that, or even at 2.5 sometimes, it’s time for a rethink of what I’m doing or how I’m doing it.

I was having lunch with my friend Bryton, the CEO of Aquabyte, a few weeks back, and that conversation spurred on a 5th question, which I’ll now add to my end of year routine:

• Am I excited about what I’m doing?

I’ve realized now that I’m over two years into the journey at Bolster that there’s a significant value in being really into the subject matter of the business. I thought I was at Return Path…but now I realize that I wasn’t nearly as excited about what I was doing as I could have been. Our work at Bolster of helping founders be more successful is more personally meaningful to me than solving email deliverability challenges. That work had real impact on the world…but I just wasn’t into it as much.

And that makes a big difference in answering the general question of “Am I on track?” at the end of the year. I’ll skip next week and see you all in 2023. Happy New Year and Happy Holidays, everyone!

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)

This is the second post in the series…. the first one When to hire your first Chief People Officer is here).

While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything illegal, discriminatory, or harassing, you’ll end up in legal trouble and you’ll lose—big time. So, it’s not enough, if you’re expanding rapidly, to “just get a Chief People Officer,” you need to hire a great Chief People Officer and I have found that great Chief People Officers do three things particularly well:

The most important characteristic or attribute of a great Chief People Officer is that they believe their function is strategic. In Startup CXO Chief People Officer Cathy Hawtrey wrote about the ways in which HR/People can be a strategic function and not just a tactical corporate function.  It’s true of most functions, but for whatever reason, (likely past experience), HR leaders frequently don’t view themselves or their functions as strategic, which is not only a huge missed opportunity but maybe says something more important about the confidence level of the Chief People Officer.  If that’s their frame of reference, then they will likely be tactical managers, they’ll keep the trains running on time, but you won’t be able to anticipate the changing talent landscape, much less be strategic about it.  If they believe they can move the needle on the business by improving engagement and productivity and efficiency, if they believe they can make the executive team more effective by helping you with team facilitation and coaching…they can do anything.

A second important characteristic of the Chief People Officer is courage—they have the courage to call you (you, the CEO) out on things directly and firmly when they see you doing or saying anything that is a bit off. It could be around language, inclusion, values, authenticity, or anything else, but they don’t let it slide or ignore it. The CPO, along with you, are the principal stewards of the company’s values and culture.  Even the best CEOs benefit from having a watchdog from time to time.

A third critical trait of a great Chief People Officer is that they think about investment in People in terms of ROI.  It’s one thing to run a killer recruiting function and fill seats efficiently, with high quality, as asked.  It’s an entirely different thing to start the recruiting process by asking if the role is needed, at that level and compensation band, or whether there are other people, fractional people, contractors, or shifts in lower value activities that could be put to work instead.  Only heads of People with deep understandings of the business can transform the function from a gatekeeper/”no” role into a business accelerator.

A great Chief People Officer is all of these things—strategic, courageous, and financially astute. Above all, great Chief people Officers know that they are the role model within a company and that their behavior, their language, their inclusiveness is setting the tone and providing a template for others to follow. 

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

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)

Post 4 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO, When it is Time to Hire Your First Chief Financial Officer, and What Does “Great” Look Like in a CFO?)

While all the functions of a team are needed, perhaps the most critical function to make sure your company is able to scale is the CFO. Cash flow, investments into the business, compensation, budgets—nearly everything that happens in a company flows through the CFO—and it should. So, getting this role right is one of the most important tasks of any startup team. But how do you know if your CFO is up to the task of scaling?

For CEOs, one of the first things that’s a telltale sign is what I call the gut check: do you have an uneasy feeling about cash, either that you’re running out of cash, or that you’re unsure how much cash you’re burning through and how fast you’re spending it?  Do you spend a lot of your time dealing with finance-related issues like fundraising, debt, investors, or cap table questions? Are you on the hot seat during board meetings on finance-related questions, metrics, runway, cash burn, or other issues? Trust your gut. If you have even a little uneasiness about how your CFO is operating, it’s probably worth heeding. You might not have a person capable of scaling, or you might have to invest more resources (time, mentor, fractional executive) to level up your CFO.

For members of the executive team, a telltale sign is whether or not your CFO engages with you and your team to understand your part of the business. Do they spend time learning and steeping in the substance of the business? Do they interact with all the functional leads like product, marketing, and People? Do they spend time in-market with customers, partners, or vendors? Sure, a CFO can understand the business by looking at the numbers, but you’ll never be able to scale if that’s the primary focus of your CFO because the numbers—all of them, and all of the time—are lagging. It’s impossible to be proactive if your CFO is totally focused on the numbers but doesn’t understand your functional issues, timelines, upcoming events or expenditures—and why. A CFO who is capable of scaling doesn’t see their role as “corporate,” as “administrative,” or as an enforcement function. They see it as strategic and as a partner to other parts of the business.

Other Signs Your CFO Isn’t Scaling

One sign of a CFO that can’t scale is whether or not they’re scrambling to hit deadlines. Everybody has to pull an all-weekend stint or over-nighter—occasionally, but if it happens regularly…it probably isn’t going to improve over time as things become more complex in the business. There’s always a pending crunch time that requires their personal attention and a ton of manual work – the monthly close, the audit, the budget, commission planning, compensation cycles.  These things are not surprises, and they come up the same time every month, quarter, or year. CFOs who are mired in doing all these things personally and manually haven’t built the systems, teams, or processes required to scale the business.

Another sign that your CFO can’t scale is if their solution to problems is to throw more people at it. If the accounting teams swells in size you might have a CFO who can’t think strategically about creating innovative processes and systems. “Throwing bodies at the problem” is easy because it’s the path of least resistance, but would your CFO allow other teams to do that? Accounting teams in particular tend to be the most traditional, paper-based teams and don’t need to be. Your CFO should be thinking strategically about how to scale financial systems with process and procedure rather than adding headcount.

A final obvious sign that your CFO isn’t scaling is if they get forecasts wrong, or don’t even try to do them.  Especially while your startup is in burn mode and constantly calculating its runway and months until the next required financing, regular and accurate/conservative forecasts are critical.  Even without a ton of revenue visibility on forward looking sales, good CFOs should have enough of a grip on expenses, cash flow, and order-to-cash dynamics to produce good, rolling 12-month cash forecasts. Anything short of that and you’ll be blindsided in the market, unable to take advantage of opportunities, or limping along with so-so growth for a long time.

In many startups people are learning on the fly but at some point you’ll begin to wonder whether everyone’s able to keep up or, more importantly, whether the people you have will be able to help your company scale. The CFO role touches every part of the organization and it’s critical to figure out earlier rather than later if your CFO can scale or whether you need to go in another direction.

(Posted on the Bolster blog here).

Across 22 years and two companies now, our system of giving performance feedback has evolved significantly. I thought I’d take a pass at chronicling it here and seeing if I had any learnings from looking at the evolution. Here’s how things evolved over the years:

• Written performance reviews. The first year of Return Path, we had a pretty standard process for reviews. They were more or less “one-way” (meaning managers wrote reviews for their direct reports), and they only happened annually.
• Written 360 reviews. We pretty quickly moved from one-way reviews to 360s. I wrote about this here, but we always felt that being able to give/receive feedback in all directions was critical to getting a full picture of your strengths and weaknesses.
• Live 360 reviews. In addition to the above post/link, I wrote about this a bit further here and here. The short of it is that we evolved written 360s for senior leaders into facilitated live conversations among all the reviewers in order to resolve conflicting feedback and prioritize action items.
• Live 360 reviews with the subject in the room. I wrote about this here…the addition of the subject of the review into an observer/clarifying role present for the facilitated live conversation.
• Peer feedback. At some point, we started doing team-based reviews on a regular cadence (usually quarterly) where everyone on a team reviews everyone on a team round-robin style in a live meeting.

The evolution follows an interesting pattern of increasing utility combined with increasing transparency. The more data that is available to more people, the more actionable the feedback has gotten.

The pluses of this model are clear. A steady diet of feedback is much better than getting something once a year. Having the opportunity to prioritize and clarify conflicts in feedback is key. Hearing it firsthand is better than having it filtered.

The biggest minuses of this model are less clear. One could be that in round robin feedback, unless you spend several hours at it, it’s possible that some detail and nuance get lost in the name of prioritization. Another could be that so much transparency means that important feedback is hidden because the people giving the feedback are nervous to give it. One thing to note as a mitigating factor on this last point is that the feedback we’re talking about coming in a peer feedback session is all what I’d call “in bounds” feedback. When there is very serious feedback (e.g., performance or behavioral issues that could lead to a PIP or termination), it doesn’t always surface in peer feedback sessions – it takes a direct back channel line to the person’s manager or to HR.

The main conclusion I draw from studying this evolution is that feedback processes by design vary with culture. The more our culture at Return Path got deeper and deeper into transparency and into training people on giving/receiving feedback and training on the Difficult Conversations and Action/Design methodologies, the more we were able to make it safe to give tough feedback directly to someone’s face, even in a group setting. That does not mean that all companies could handle that kind of radical transparency, especially without a journey that includes increasing the level of transparency of feedback one step at a time. At Bolster, where the culture is rooted in transparency from the get go, we have been able to start the feedback journey at the Peer Feedback level, although now that I lay it out, I’m worried we may not be doing enough to make sure that the peer feedback format is meaningful enough especially around depth of feedback!

The old carpenter’s axiom of being extra careful to plan before executing is something not enough executives take to heart in business. Just like cutting a piece of wood a little too long, sometimes you execute in ways that can be modified on the fly; but other times, just like the cases where you cut a piece of wood too short, you can’t. And of course, in business, sometimes it’s somewhere in between. Some examples:

• One example that’s a little more literal is around cutting staff or planning a layoff. Layoffs are traumatic for everyone involved – mostly those impacted, but for you as CEO and for your remaining organization as well. Being thoughtful about how much you cut and (unlike the case of a piece of wood) erring on the side of cutting more than you think you need to can prevent you from having to do a second set of even more traumatic layoffs down the road
  
• Getting a lease on a new office? Plan, plan, and plan again – you can end up spending too much if you get too much space and can’t sublet it…you have a real headache if you don’t get enough space and need to scramble for more
  
• Planning a major investment in a new product? You don’t want to spin up a whole new effort internally and hire people before you’ve done enough discovery and planning to know it’s worth it

It’s an interesting question as to whether or not this axiom conflicts with the startup mentality of moving quickly and with agility. I don’t think it does, although in the startup ecosystem, a lot of fixed decisioning has moved to variable, which means you may be faced with fewer times where you need to measure twice. For example, a lot of SaaS licenses you have to buy are per-seat, or AWS costs are fluid. All that is much easier than perpetual license software models or standing up servers in a data center.

I’m a big fan of Eisenhower’s line that “plans are nothing but planning is everything.” That’s why I like to measure twice, cut once when I’m working on something big. It just raises the odds of getting it right, whatever it is.

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.

Curbing My Enthusiasm

For the first time since I started blogging over four years ago, I have recently run into several examples in a short period of time where I’d love to blog about something happening in the business, and I think it would make for a great blog posting, but I can’t do it.  Why can’t I?  Lots of different reasons:

– Don’t want to telegraph strategy to the competition

– Don’t want to compromise an employee (current or former)

– Worried about downstream legal ramifications

There are other reasons as well, but these are the main three.  I love transparency as much as the next person (and more than most), but these scenarios have to trump transparency in my position as a CEO.  Hopefully the passage of time and the release of news will mean that I can still do the blog postings, but as more of a post mortem than something in the moment. 

But I hate curbing my own enthusiasm.  It’s a definite frustration in this case, and a new one.

I just said this to a fellow little league coach, and it’s certainly true for baseball.  I’ve coached games with sloppy and/or blowout wins in the past.  You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game.  And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run.  You are sad about the L, but at least you left it all out on the field.

Is that statement true in business?

What’s an example of a “bad” win?  Let’s say you close a piece of business with a new client…but you did it by telling the client some things that aren’t true about your competition.  Your win might not be sustainable, and you’ve put your reputation at risk.  Or what about a case where you release a new feature, but you know you’ve taken some shortcuts to launch it on time that will cause downstream support problems?  Or you negotiate the highest possible valuation from a new lead investor, only to discover that new lead investor, now on your Board, expects you to triple it in four years and is way out of alignment with the rest of your cap table.

On the other side, what’s an example of a “good” loss?  We’ve lost accounts before where the loss was painful, but it taught us something absolutely critical that we needed to fix about our product or service model.  Or same goes for getting a “pass” from a desirable investor in a financing round but at least understanding why and getting a key to fixing something problematic about your business model or management team.

What it comes down to is that both examples – little league and business – have humans at the center.  And while most humans do value winning and success, they are also intrinsically motivated by other things like happiness, growth, and truth.  So yes, even in business, sometimes a good loss is better than a bad win.