(Post 4 of 4 in the series on Scaling CMOs – other posts are, When to Hire your First Chief Marketing Officer, What Does Great Look like in a Chief Marketing Officer and Signs your Chief Marketing Officer isn’t Scaling)

Similar to interactions with all CXOs, you’ll have to capitalize on your moments but there are a few ways I’ve typically spent the most time or gotten the most value out of CMOs over the years.

 One of the key ways to engage with the CMO is to include them in meetings with the rest of the go-to-market (GTM) executives as a group, not in a silo.  While of course I have always had 1:1 meetings with my CMO, I find that the most valuable conversations are the ones with the GTM group as a group, talking about shared objectives and the underlying drivers and coordination points to get there. You might say, “Well, Matt, that’s true of all the GTM executives,” but I disagree. It’s even more important to have the CMO in the same room as the other GTM roles like Sales, Account Management, and Partnerships because marketing needs to be on the leading edge of GTM, not just a function working in a silo at the direction of the other GTM leaders. A lot of what happens in the GTM meetings is nuanced and since Marketing has to somehow make everything tangible, the earlier they hear about it and can start thinking about it the better off the whole company is.

On the other end of the spectrum, I find it very useful to create a thinking session with the CMO, where we take time away from the day-to-day to do deep dives on strategic topics like the company’s positioning, voice, or brand.  Sometimes I like to do these in the context of reading a relevant marketing book or business journal article, or after reading something I ran across on the internet, or something I learned at a conference—something that piqued my interest. Sometimes I don’t have a perspective or an idea, but the thinking session is valuable either way.  I find that the most creative thinking and ideas happen in some of these longer form, unstructured conversations. These sessions are not limited to ideas, positioning, or branding because even the quantitative part of marketing involves a lot of creativity. So, the thinking session can be wide open in terms of agenda, but it needs to be scheduled and done, otherwise all these ideas just ramble around and we don’t make as much progress.

Finally, a lot of my engagement with the CMO is actually a continuation of a longer relationship, before they become the CMO.  Let me explain what I mean. For years, we went through CMOs at Return Path at the same clip as other companies: every 1-2 years we’d make a change and bring in the new flavor-of-the-month CMO and we had a pattern of hiring them from the outside.  Over time, though, we realized that we would be much better served by having more continuity in marketing by investing in our own people and promoting them from within.  The last few CMOs we had at Return Path were all promoted into the role — so I got to know them pretty extensively ahead of time. I was not only thrilled to give them a shot at the top job, but I was in a great place to understand their strengths and weaknesses coming into the role so I could most effectively mentor them.  Of course, you can say the same thing for the other functional departments, but marketing is more acute based on the average tenure of CMOs.

(You can find this post on the Bolster blog here).

I wrote a post the other day about innovating employee benefits practices, and I realized I’d never documented a couple other ways in which we have always tried to innovate People practices. Here’s one of them: the Open Expense Policy, which I wrote about in the second edition of Startup CEO in a new chapter on Authentic Leadership when talking about the problem of the “Say-Do” gap.  Here’s what I wrote:

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

When we started Return Path, we had a similar policy. It was standard issue. But then over time as our culture became stronger and our People First philosophy and approach became something we evangelized more, we realized that traditional expense was at odds with our deeply held value of trusting employees to make good decisions and giving them the freedom and flexibility they needed to do their best work.

So we blew up the traditional policy and replaced it with a very simple one — “use your best judgment on expenses and try to spend the company’s money like it’s your own.” That policy is still in place today for our team at Bolster. We do have people sign off on expense requests that come in through the Expensify system, mostly because we have to, but unless there is something extremely profligate, no one really says a word.

Similar to what happened when we switched to an Open Vacation policy, we had some concerns from managers about employees abusing the new un-policy, so we had to assure them we’d have their back. But do you know what happened when we implemented the new policy? We got a bunch of emails from team members thanking us for trusting them with the company’s money. And the average amount of expenses per employees went down. That’s right, down. Trusting people to exercise good judgment and spend the company’s money as if it was their own drove people to think critically about expenses as opposed to “spend to the limit.”

I don’t think in 15+ years of operating with an Open Expense policy that any of us have had to call out an employee’s expenses as being too high more than once or twice. That’s what the essence of employee trust is about. Manage exceptions on the back end, don’t attempt to control or micromanage behavior on the front end.

I love stealing/borrowing other people’s good ideas for management and leadership when they’re made public, and I always encourage others to do so from me. I call it “plagiarizing with pride.” So I was intrigued when I saw a new way of doing all-hands meetings published by my friend Daniel Odio (DROdio) on his founder community called FounderCulture. You can see the original post here.

We’ve experimented with different formats and cadences for all-hands meetings over the years. They tend to vary with the size of the company and complexity of the material to cover. Larger companies usually fall into the rhythm of doing quarterly all-hands meetings sometime after the end of the quarter, usually around a Board meeting, with a quarterly recap and forecast for next quarter.

But for early stage companies, there’s no tried-and-true method. We struggled with that for a while at Bolster. Weekly felt too much. Quarterly felt like too little. It seemed weird for me or my co-founders to just have a meeting where we talked at everyone…and it also seemed weird to just host an “open mic night” type meeting. Then I saw DROdio’s video, and we adapted it. It’s working pretty well for us. Here’s what we do in what we’re calling our Open All-Hands Meeting:

• We hold an all-hands meeting every Monday for :30
• A different team member is responsible for being the host/chair/emcee for each meeting
• We run the meeting off of a dedicated Trello board with specific columns of information. Everyone is invited to contribute to the Trello board in the days leading up to the meeting. The columns are:
  • Values-Kudos-Good News: Anyone can call out anyone for doing something that demonstrates one of the company’s values, that is just a big thank you, or that is some other piece of karmic goodness they want to share
  • Wins: All client wins are shown here with some detail, each in its own card with its owner highlighted
  • #MAD: This is where we trade items on which we Made A Decision during the prior week, big or small. We’ve always struggled with the best way to keep everyone informed on things like this…and this works really well for that purpose
  • Learnings/Product Ideas: Anyone can populate this with anything they want as they go about their work and either come across learnings or product ideas they want to share
  • Announcements: Pretty self-explanatory, any corporate announcement, new employee introductions, etc.
  • Swim Lane Updates: Each we, we ask one or two of our functional or project areas to do a deep dive update — Product, Finance, Sales, Marketing, Ops, etc. — and this is also where we’ll do product demos of newly released functionality
  • Permanent Items: this isn’t a column that’s read…it just warehouses things we want on the board like the schedule of hosts, schedule of swim lane updates, instructions for running the meeting, recordings of prior meetings
  • BOLSTER 2022: this isn’t a column that’s read…it contains our mission, values, strategy, and key strategic initiatives and metrics for the year
  • Archive: this isn’t a column that’s read…it just contains the prior week’s items
• There’s a series of light integrations between Slack, Hubspot, and Trello to automatically populate Trello based on certain channels, keywords, and emojis. Every week, the board is automatically wiped clean after the meeting
• The host moves the meeting from column to column and card to card, sometimes reading the cards, and sometimes asking the person who submitted the card to read it or give color commentary on it
• I do jump in from time to time, as do some of my co-founders or our other leaders, to give extra commentary or amplify something or help connect the dots. But that’s about as formal as my role gets other than…
• …when we do have a quarterly board book and board meeting, I host that one meeting and recap the meeting, ask other leaders to comment on specific topics, and facilitate Q&A on the materials we send out ahead of time. So I’m hosting 4 meetings per year
• The host can add a personal touch to any meeting. Custom wallpaper for the Trello board. Asking everyone in the company who has a pet to send in a photo of the pet ahead of time and introducing their furry friends during the meeting. Playing intro or outro music to fit the occasion. Doing spot surveys or game show questions to keep things lively. Interviewing new team members. Asking everyone to do a one-sentence “here’s what I’m working on this week” at the end of the meeting
• Finally, the host passes the baton from one person to the next each week. No one can escape this responsibility!

In addition to the Open All-Hands Meeting format, I send the company an email every Friday with some musings on the prior week. The content of these varies widely – from “what I did last week,” to “here’s something I saw that’s interesting,” to welcoming new team members with their bios, to customer testimonials. Sometimes other founders write these. They’re a good way to add a personal touch to the operating system of the company — and we also send these to our board and major shareholders every week so they, too, can keep a finger on the pulse.

These two things together are proving to be a good Operating System for keeping everyone informed, aligned, and connected on a weekly basis.

I love innovation, and process is no different than product or business model in that regard. I’ve run and attended several hundred board meetings over the years, both those of companies where I’ve been CEO or Chairman, and those where I’m a director. I’ve written a lot about how I like running board meetings in Startup CEO, and as I mentioned the other day, I’m a co-author of a Second Edition of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, which is coming out in June and is available to pre-order now, along with Brad Feld and Mahendra Ramsinghani.

There are two adaptations I’ve made to my standard board routines in the last year or so, one driven by the pandemic and one not.

In olden times (that makes me sound like I’m 400 years old, but “pre-covid” sounds so clinical), I used to have a board dinner the night before or after every board meeting, and of course, everything was in person. That was a really important ritual in my mind towards the end of building the board as an effective team, where people on the team know each other as people, share things going on in their lives, share vulnerabilities, and develop bonds of trust. Without regular in-person meetings and dinners or social events, that gets a lot harder. Even when we get back to “normal,” I imagine the most we’ll do in-person board meetings is 1-2x/year.

What’s the zoom version of this?

We now do two 30-minute Executive Sessions (directors only) one before the board meeting officially starts and observers and team join, as well as the traditional one after the meeting ends. The purposes of the two sessions are different. The standard post-meeting Executive Session follows up on the meeting and has me talk about business or team issues that I don’t want to talk about with the full group present or get feedback from the board. But the one before the meeting is almost entirely social. I try to come up with a different question or topic to get all of us talking that is not about Bolster. Last week’s meeting was a simple “what’s the best thing that’s happened to you so far in 2022, and what’s the worse?” One time I asked everyone to show a picture from their phone photo roll and talk about it. You get the idea. It’s not the same as a dinner, but it seems like an effective substitute given the medium.

The second adaptation, and full credit to Fred for suggesting this one a while back, is the post-meeting survey. Now immediately after every Board meeting, I send a simple Google form to each director with the following questions:

• What are 1-3 areas/specifics where we are doing well?
• What are 1-3 areas/specifics you’re concerned about or where we could do better?
• Did the board book have the right level of detail and commentary?  Is there anything you’d like to see change about the format or the content?
• Did the meeting meet your objectives for learning and discussion? 
• If not, why not?
• Do you have any other feedback for Matt at this time?

I get great feedback, almost immediately and always from all board members, while things are still fresh in everyone’s mind. I’m planning to do this whether or not the meeting is remote…although it’s definitely good when the meeting is remote, and things like Executive Session, Closed Session, and debrief with me after Closed Session are quick or sometimes rushed.

There’s always room for innovation, even in standard and time-tested processes like board meetings.

I hope this post doesn’t gross anyone out or offend anyone. I admit it’s a little weird, and that it’s more accessible to men. Hopefully everyone can get my point, even if men get it a bit more. I’m channeling Brad as I write this. So bear with me.

Here is a picture of a men’s room with floor mats under the urinals.

The difference between using a men’s room that has floor mats and using a men’s room that does not have floor mats is profound in multiple ways. I’ll leave out the specifics, but you can imagine the comparative experiences if you haven’t had one or both.

A really good floor mat, from a quick scan of Amazon and Uline just now, costs $11 if you buy in bulk and is built to last 4-6 weeks. That gives us an annual per urinal expense of about $100 – trivial in the scheme of maintaining an office, restaurant, or place of business.

But here’s the thing. These floor mats are few and far between. I don’t have scientific research on the matter, but I’d guess that between 1 in 5 and 1 in 10 places of business have them. Maybe even fewer.

So, urinal floor mats are (a) cheap, (b) easy to acquire, and (c) make a profound difference in the environment. And yet, they are only have 10-20% market penetration at most.

That market penetration is not far off from the prevalence of very good leadership and management in business. I hear stories all the time from executives about absolutely terrible leadership practices. I also hear plenty of stories that aren’t awful, but are evidence of non-leadership or non-management. The experience of working for a good manager, or in an organization with strong leadership, is profoundly different than working with the absence of those things.

To complete the analogy, good management and leadership are also (a) cheap, (b) easy to acquire, and (c) make a profound difference in the work environment. Sure, you can’t buy good leadership online, but it’s not all that difficult to be a caring, supportive, transparent manager. Heck, there’s even a book called The One Minute Manager.

So why the low market penetration of both? It makes no logical sense. It’s not as if most people haven’t had the experience of using a urinal with a floor mat…or of having a really good leader or manager. It’s not as if leaders and decision makers don’t appreciate those things themselves.

The answer boils down to three simple points that anyone who is a manager or leader can do, any day:

• You have to pay attention
• You have to care
• You have to act

Great leaders and managers exhibit all three of these traits. They pay attention to things around them, noting that Everything is Data. They care about people, about experiences, about impressions, about reputations. And when they notice that something is off – however small it is – they care enough to remember and then take the time to act. To make a small change. Send an email. Have a quick conversation. Make a suggestion. Give someone quick praise or constructive feedback.

And to come back to where this post started – it’s also not that hard to have a nice men’s room at your office or business or restaurant. You just have to pay attention to the fact that it’s a much better experience to buy floor mats. You have to care about the experience in the men’s room (for yourself, for employees, for customers, for vendors, for visitors). And then you have to act and either buy the stupid mats or ask an office manager to do the same!

I’m pretty close to the executive coaching world. My wife Mariquita is an extraordinary CEO coach. I’ve worked for decades with Marc Maltz from Hoola Hoop, who helped me transform everything about how I lead organizations. I’ve been friends with Jerry Colonna of Reboot fame for years (I did a fun podcast with Jerry last year called “Everyone is Scalable). I’m pretty good friends with Chad Dickerson. Bolster’s marketplace helps place CEO coaches and even has a programmatic approach to coaching and mentoring called Bolster Prime. The list goes on.

My friend Mitch, a fellow baseball coach, gave me a fun book a couple years ago that is a page-a-day called Coach: 365 Days of Inspiration for Coaches and Players, by Matthew Kelly. It’s a compilation of quotes. Some are better than others. But I just love this one from a couple weeks ago. While obviously it is in the sports context, the sentiments are the same around executive coaching.

Marc and I had one senior executive who we worked with years ago. They had significant personality and style issues that weren’t working well in our culture. They were abrupt, needlessly angry, and cultivated relationships based on fear, not based on trust. Marc and I were tearing our hair out trying to give this person feedback and coaching. Nothing was working. Then I delivered a 2×4 between his eyes. They argued with me and Marc and said that the problem was us…not them. That we were soft.

Two days went by. Then we met with them again. They came into the meeting visibly upset, shaking their head and a bit choked up. They opened the meeting by saying, “I went home and complained to my spouse about your feedback. And my spouse told me that, actually, you are right, and that I should ask my kids. My whole family feels the same way you do. More than my job is at risk — my marriage and family are at risk, too.”

Months and years later, with a ton of coaching and feedback and support from Marc and me and the rest of our executive team, this person had really turned it around. They were doing better at work. They were doing better at home. The work was long and painful and not without its bumps and backtracks. But the person made changes that were meaningful and permanent to all their relationships, not just something in the moment at work. It’s a clear case of this quote — coaching changed his life.

As I’ve said before, People are People. It doesn’t matter if you’re at home or at work. It doesn’t matter if you’re a B2C person or a B2B person. While there are some prominent examples of individuals throughout history who have very different work and home personae (John D. Rockefeller is one that comes to mind, but I’m sure there are other famous ruthless businesspeople who were empathetic and loving spouses and parents), most of us are simply humans, works in progress. We learn something in Context A, and it’s part of us when we are also in Context B.

The impact of a good coach goes way beyond how you lead your organization.

Unknown Unknowns

OnlyOnce – The Car

Not really contemplating a brand extension to my blog — the book is enough, but my friend Bill Wise just saw this car today in Larchmont, NY!

Counter Cliche:  How Much Paranoia is Too Much Paranoia?, Part II

After the original posting, one of my readers wrote in with the following question:

I was one of the first employees at a pre-funding enterprise social networking company, after having consulted on doing their business plan for them (not coming up with it; mainly turning the CEO and CTO’s engineer-speak into English). 

So with all that background, when you say “open book” to your employees, can you break that out some more?  I have an idea of what I think that means, and what it doesn’t, but I’d love to hear your thoughts on it too.

My thoughts on this are quite simple.  We are willing to share everything internally other than compensation.  We publish detailed monthly financials and reporting to the team, and we ask that they treat the information as extremely confidential.  We have had only good things come from this level of openness with our team.  Good ideas, good esprit de corps, and a radical reduction in fear of the unknown (the old "Looks like we had a bad quarter, does that mean I need to look for a job now?  Are we running out of money?"). 

In fact, I know one other CEO who goes so far as to publish an only-slightly modified version of his Board books to the entire company.

Transparency is a good thing.

How to Wow Your Manager

Last week, I talked about how to Wow your employees.  Now I am going to discuss the converse of that – How to Wow your Manager.  Why Wow your manager?  Even if you are senior leader in an organization, the Wow factor is still important.

What impact does a Wow have?  It sends the signal that you are on top of things.  Symbolism is important.  It also advances the cause further and faster.  Why do you want to foster Wow moments with your team?  High performing teams have a lot of Wow going on.  If all members of a team see Wow regularly, they are all inspired to do more sooner, better.

Here are my top 10 examples on how to WOW your manager, along with the intended impact:

1. Show up for every check-in with the full agenda – send it a day or more ahead (Give your manager time and space to prepare)
2.  When you are asking your manager to communicate something (an email to the team, a reference letter, etc.), draft it for him or her (Editing is much easier than creating)
3.  Do a start-stop-continue analysis once a year on all of your key activities (Make yourself as efficient and effective as possible – that’s your responsibility as much as your manager’s)
4.  Own your own development plan and check in on it at least quarterly (Those who own their own career paths progress more quickly down them)
5. Read a relevant business book and ask your manager to discuss insights with you (Staying current with best practices in your field – books, articles, blog posts, videos, mentors, lectures –  is key in a learning organization)
6.  Dress for success – even casual can be neat and “client ready” (Your presence has an impact on those around you.  There’s no reason anyone should ever have to comment on your clothes, your hair, or any aspect of your personal hygiene)
7. Respond to every email where you are on the TO line within a day, even if it’s to say you will respond longer form later (At Return Path,  you have to be in the jet stream of communications. Otherwise, you find yourself in the exhaust of the jet stream)
8. End every meaningful interaction by asking for informal feedback on how you’re doing and what else you can be doing (Again, part of being in a learning organization…and taking more tasks on is always a sign that you are ready for more responsibility)
9. Do something that’s not required but that you feel is a best practice (This shows you’re on top of your game.  One example:  I send the Board a summary, the details, and the YoY trending of all of my expenses every year.  I don’t have to, but enough CEOs out there have high profile expense problems that I decided it’s a good practice.  They all LOVE it)
10.  (If you have staff reporting into you) Show up for every check-in with  your manager with a list of all staff issues and highlights (You need to bubble things up, both good and bad, so your manager is on top of his or her overall team and (a) is never surprised by events, (b) knows how best to handle skip-level communications, and (c) can think more broadly about resource deployment across the organization)

Good Help is Hard to Find

We’re having a bitch of a time lately hiring good sales people.  We’re growing like crazy this year and are trying to invest more in our salesforce, but it’s not easy.  And we’re a good catch.  Good brand, healthy company, good comp and benefits, charming CEO, the works.

I just traded emails with a friend who is CEO of another online marketing services firm who said the same thing, with the exact same explanation I have:

I have been so unimpressed with everyone from our space (weak links drop out, mediocrity churns from company to company, and true talent is retained).

Anyway, we have gotten very lucky with a few key hires the past few months — and we certainly work like mad to retain the talent we have (or at least we try hard!) — but the reality is that it’s a good year for Internet businesses, and it’s hard to get people to jump ship when they have an established book of business and good commission check flow. 

Most of the people I know who are doing well with sales recruiting in our space these days, including ourselves, are mostly pulling people out of adjacent industries or even out of clients.  I’d ask my general readership for advice, but I assume if you have the secret sauce here, you’ll hoard it for yourself!