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

Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent.

One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events.  Particularly if you’re a B2B company that engages with clients during the sales process, you’ll probably find yourself at a lot of client meetings and events, either internal or external.  Your CRO will be there, too, which gives you a great opportunity to spend large blocks of time together in transit, or a good deal of time together socially. One thing we learned during the work-at-home pandemic is just how much time we save by not traveling.  So when life resumes to normal, why waste time in an Uber or on a plane when you can have a deep strategic conversation or even a personal/social one with one of your senior executives? Of course, you have to actually be more proactive in meeting with your CRO since you won’t have events that naturally bring you together, but I’ve found that the early morning time in the hotel gym or late-night drink in the lobby bar before heading up to bed now translates to time I can have with my CRO. 

Another way to engage with the CRO is In a Weekly Forecast meeting.  Jeff Epstein, former CFO of Oracle, was one of my long-time board members at Return Path and he helped us architect a new core business process once our sales team got large and mature and geographically disparate enough that it was hard for us to have a solid forecast.  Both me and our CFO engaged in the Weekly Forecast meeting and because of that we forced the discipline of a good roll-up of all regions and business units. The CRO and all sales managers attended and knew that we were paying attention to the numbers and trends and asking tough questions. Our attendance was a forcing function for the CRO so that they organized a pre-meeting the prior day with all teams and units to prepare, and that in and of itself had a cascading effect through the organization of adding discipline, rigor, and accuracy to the forecast.  It also made me a lot more empathetic to my CRO’s issues with respect to the sales leadership team.

Finally, the other way that I engaged with the CRO was ad hoc, either internally or in-market.  My most successful heads of sales have been good at winding me up and pointing me at things as needed, whether that means getting on a plane or Zoom to help close a deal or save a client, or doing a 1:1 mentoring session with a key employee. So, not all interactions with the CRO have to be initiated by the CEO, and a great CRO will use the CEO, leverage their time, when it’s needed.

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

A friend of mine just emailed me and asked how I collect feedback from the Board after Board meetings. I have a good routine for this which I wrote about a little bit here but have since expanded.

First, we are disciplined about leaving an hour at the end of the board meeting for the following three things :

• Executive session – directors only, including me – sometimes I’ll have my CFO Jack come for a few minutes at the beginning, depending on the topics. The topics can be about people on the team, or things I’m concerned about that I didn’t want to talk about with observers and team present. I tee up any topics in a separate memo that I send only to board members when I send the main board book out. My board meetings are very inclusive – lots of team members and observers present, so it’s good to have this time available case the Board wants to talk more openly with me about something or ask questions they didn’t feel like asking with the broader group in the room.
• Closed session – I leave, so I give non-management directors an opportunity to talk about any issues related to me.
• CEO Debrief – I ask one director to take notes for me during Closed Session, then that person calls me back in to debrief anything.

All three of these are important, and it’s important to do them every meeting, even if you don’t have any specific issues to discuss. That way, no one freaks out (including you) if suddenly and unexpectedly, there’s a part of the meeting to which they’re not invited.

The key to this is really leaving time for it. Now that board meetings are often on Zoom, a lot of CEOs have shrunk the time to 2-3 hours to avoid Zoom fatigue, but that doesn’t usually leave a full hour for this end-of-meeting routine. Finish your main meeting, give everyone 10 minutes to breathe, then come back for the final three steps of the meeting.

Then, I use this form after every meeting, which was a suggestion from Fred a few years back (not here or here, though these are also really good posts he wrote on this topic). I sent it during Executive Session and ask people to fill it out immediately after the meeting while things are fresh in their minds.

Quick, easy, effective. You should never finish a Board meeting and have no idea how it went.

Book Short:  Vulnerability Applied to Leadership

Getting Naked:  A Business Fable About Shedding The Three Fears That Sabotage Client Loyalty (book, Kindle), is Patrick Lencion’s latest fable-on-the-go book, and it’s as good a read as all of his books (see list of the ones I’ve read and reviewed at the end of the post).

The book talks about the power of vulnerability as a character trait for those who provide service to clients in that they are rewarded with levels of client loyalty and intimacy.  Besides cringing as I remembered my own personal experience as an overpaid and underqualified 21 year old analyst at how ridiculous some aspects of the management consulting industry are…the book really made me think.  The challenge to the conventional wisdom of “never letting ‘em see you sweat” (we *think* vulnerability will hurt success, we *confuse* competence with ego, etc.) is powerful.  And although vulnerability is often uncomfortable, I believe Lencioni is 100% right – and more than he thinks.

First, the basic premise of the book is that consultants have three fears they need to overcome to achieve nirvana – those fears and the mitigation tactics are:

1. Fear of losing the business:  mitigate by always consulting instead of selling, giving away the business, telling the kind truth, and directly addressing elephants in the room
2. Fear of being embarrassed:  mitigate by asking dumb questions, making dumb suggestions, and celebrating your mistakes
3. Fear of feeling inferior:  mitigate by taking a bullet for the client, making everything about the client, honoring the client’s work, and doing your share of the dirty work

But to my point about Lencioni being more right than he thinks…I’d like to extend the premise around vulnerability as a key to success beyond the world of consulting and client service into the world of leadership.  Think about some of the language above applied to leading an organization or a team:

• Telling the kind truth and directly addressing elephants in the room:  If you’re not going to do this, who is?  There is no place at the top of an organization or team for conflict avoidance
• Asking dumb questions:  How else do you learn what’s going on in your organization?  How else can you get people talking instead of listening?
• Making dumb suggestions:  I’d refer to this more as “bringing an outside/higher level perspective to the dialog.”  You never know when one of your seemingly dumb suggestions will connect the dots for your team in a way that they haven’t done yet on their own (e.g., the suggestions might not be so dumb after all)
• Celebrating your mistakes:  We’re all human.  And as a leader, some of your people may build you up in their mind beyond what’s real and reasonable.  Set a good example by noting when you’re wrong, noting your learnings, and not making the same mistake twice
• Taking a bullet for your team, making everything about your team and honoring your team’s work:  Management 101.  Give credit out liberally.  Take the blame for team failings.
• Doing your share of the dirty work:  An underreported quality of good leaders.  Change the big heavy bottle on the water cooler.  Wipe down the coffee machine.  Order the pizza or push the beer cart around yourself.  Again, we’re all human, leaders aren’t above doing their share to keep the community of the organization safe, fun, clean, well fed, etc.

There’s a really powerful message here.  I hope this review at least scratches the surface of it.

The full book series roundup as far as OnlyOnce has gotten so far is:

• The Three Signs of a Miserable Job (post, book)
• The Five Temptations of a CEO (post, book)
• The Four Obsessions of an Extraordinary Executive (post, book)
• Death by Meeting (post, book)
• The Five Dysfunctions of a Team (post, book, Field Guide)
• Silos, Politics and Turf Wars (post, book)
• Getting Naked (post, book)

The Catcher Hypothesis

Here’s an interesting nugget I just picked up from Harvard Business Review’s March issue in an article entitled “Making Mobility Matter,” by Richard Guzzo and Haig Nalbantian.

Of the 30 teams in Major League baseball, 12 of the managers are former catchers.  A normal distribution would be 2 or 3.  Sounds like a case of a Gladwellian Outlier, doesn’t it?  The authors explain their theory here…that catchers face their teammates, that they are closest to the competition, that they have to keep track of a lot of things at once, be psychiatrists to flailing pitchers, etc.  Essentially that the kind of person who is a successful catcher has all the qualities of a successful manager.

What’s the learning for business?  Part of having a strategic orientation towards the people in the business is making sure that you’re creating development paths for people, which is both good for them and good for the organization to train future leaders.  Another part is making sure great people don’t get bored — especially in tough economic times when organizations aren’t growing, new roles aren’t opening up, and promotions and even lateral moves are harder to come by.

Back to the Catcher Hypothesis.  A good strategic people plan, whether or not you have a head of HR to develop it (if you don’t, it’s your job!), will identify “training ground” positions within your organization.  The larger we get, the more of these we try to carve out.  Sometimes it’s pulling people out of their current roles (fully or partially) and putting them in charge of a high-profile short-term, cross-functional project.  We have a couple more formal roles at the entry level, one in account management and one in application support, so we can start growing our own talent and reduce reliance on more expensive outside hires.  Another we are developing now is basically a “mini-GM” role, which should develop a whole future generation of leaders as the company grows from ~200 people to hopefully a much larger group down the road.

Who plays Catcher in your organization?

More thoughts on some of Fred’s and Brad’s points about VC deal algebra, valuation, and liquidation preferences for venture-funded startups. My apologies if this gets a little too technical or too long!

On liquidation preference: Preferred stock makes sense, participating preferred makes less sense. Sure, a VC who puts capital at risk in a startup should be entitled to get his or her money out before management and common shareholders who are paid to run the business. But I’ve always had an issue (even when I was in the venture business, although admittedly not as a partner) with the participating preferred security which allows VCs to get their money out first, and then still receive their proportional share of the rest. Fred calls this “a loan with an option,” and that’s the best presentation I’ve ever heard of the security. But what’s always struck me as a bit over the top about this is that it gives VCs downside protection at the same time they’re negotiating even more upside in a deal.

One simple solution to this, if you can negotiate it, is a “kickout” provision which makes the participation feature on the security go away if the company becomes worth a multiple (usually 2x or 3x) of the post-money valuation of the financing. In other words, it gives the VC the downside protection they want but gives you and other shareholders more of the upside if things go really, really well.

On valuation and deal algebra: I completely agree that valuation is a derived number and that it’s completely misunderstood in early stage investing. However, I think that while there may be low correlation between valuation and what the business is worth today, there are a few things that have always bugged me about VC valuations:

While I understand that valuation is more a function of future potential than current value, it sometimes feels like companies get punished for having a track record. Let me clear about my point – it’s not that that I actually think VCs lower valuations unfairly when companies demonstrate poor results. It’s actually the opposite. VCs are quick to bid up the valuation on companies that don’t have revenue or even a lot of operations just because the idea is cool or because the theoretical market is large (Friendster, anyone?). I don’t think VCs as a group do a good enough job of risk-adjusting or future-competition-adjusting valuations for new companies, or they get caught up in what Fred once called Venture Fratricide and just pour money into new sectors en masse. This has the unintended side effect of making management teams of existing companies feel like their ideas aren’t interesting any more because they’re not new and shiny.

Second, it’s interesting to note that while VCs use valuation as a way of placing limits and getting protection on their bet about the future potential of the company and entrepreneur, entrepreneurs have no corresponding mechanism to place limits or receive protection against having a bad VC. (VCs actually have many tools at their disposal to reign in poorly performing management teams once the deal is signed – they can fire them, cram them down, force all their common stock to be on a vesting schedule or subject to clawback.) But make no mistake about it – a bad VC can almost kill a company, or certainly keep it from realizing its full potential, and once that deal is signed, the entrepreneur typically has little recourse. I’m not sure there’s an easy solution to this particular problem either, but it’s one that’s worth thinking through with a good lawyer the next time you negotiate a term sheet with a new venture investor (and certainly one that is easier to negotiate if you either have a good track record as an entrepreneur or multiple VCs interested in your company). I made one suggestion around participation in future financings in my earlier posting on term sheet negotiations — item #8.

The final thing that’s bugged me about valuations stems from what Fred calls the 1/3 rule (1/3 of a VC’s investments work out well, 1/3 go sideways, 1/3 go bad). As a result of the rule, valuations and deal structures can end up being about VCs getting as much upside as possible out of their winning deals to cover their losses from their zero-return deals. What bugs me about this is that entrepreneurs don’t have that same luxury of a diversified portfolio – they are 100% invested in terms of their human capital and often their investment capital in their company. I fully realize that this is the nature of the beast, but I’ve always felt as a result that entrepreneurs should negotiate – and VCs should be willing to give – proportionally much more upside to management in the event that the deal turns out to be a big winner. This point relates back to my first point about participating preferred securities.

Next up in this series…Reverse Engineering Venture Economics, and managing other kinds of investors (Angel and Strategic).

Book Short:  Next, Write a Sequel

Written by Rodd Wagner and James K. Harter and billed as “the long awaited sequel to First, Break All the Rules” (one of the best management books I’ve ever read), I thought 12: The Elements of Great Managing, was good, but not great.  12…, along with the original book First… and Now, Discover Your Strengths, the latter two both by Marcus Buckingham, are all based on an extensive database of research done on corporate America by the Gallup organization over many years.  All three are valuable reads in one way or another, although I found this to be the weakest of the three.  (Note that Now… is different from the other two in that it’s not about management, it’s about self-management — very different, though based on the same research.)

Anyway, the elements of great managing, so say the authors, is all about creating employee engagement.  I totally buy into that.  And since no book short on 12… would be complete if it didn’t list out the 12…

1. Do I know what is expected of me at work?
2. Do I have the materials and equipment I need to do my work right?
3. At work, do I have the opportunity to do what I do best every day?
4. In the last seven days, have I received recognition or praise for doing good work?
5. Does my supervisor, or someone at work, seem to care about me as a person?
6. Is there someone at work who encourages my development?
7. At work, do my opinions seem to count?
8. Does the mission/purpose of my company make me feel my job is important?
9. Are my co-workers committed to doing quality work?
10. Do I have a best friend at work?
11. In the last six months, has someone at work talked to me about my progress?
12. This last year, have I had the opportunities at work to learn and grow?

The book fleshes out each of the 12, gives examples (some of which are better/clearer than others), and then addresses compensation in a very interesting chapter at the end.  Key takeaways on comp:

– Higher pay doesn’t guarantee greater engagement
– Good and bad employees are equally likely to think they deserve a raise
– Money without meaning isn’t enough
– Most employees, most of the time, feel undercompensated
– Individual pay can/should be private, but comp criteria should be very public
– People who feel well-compensated generally work harder

The book also cites a very provocative article suggesting that organizations would handle comp better if they made everyone’s comp public (in contrast to the final bullet above, yes).  I’m going to write more about compensation in future postings, so I’ll leave this section on those notes.

Finally, the book’s two closing thoughts are perhaps its most prescient:  one critical element of BEING a great manager is HAVING a great manager; and the managers who put the most into their people, get the most out of their people.

Change of Name

Fellow CEO Greg Reinacker posted an open question on his blog about whether he should change the name of his company, NewsGator. This is a GREAT topic.

We struggled with it for years at MovieFone, because at some point, the Internet became a huge part of the business, and the name seemed antiquated. Plus, everyone knew us by the phone number, 777-FILM (or whatever number it happened to be in any given city). But it had 10 years of brand equity at that point behind it.

Return Path used to be called uLocate.com a really long time ago, and we changed the name to be less “dot com” three months after we got started (that’a story for another posting as well). People ask me all the time if I sitll think that Return Path is the best name possible for the company. I’m sure there’s a better one out there, but I am sure it’s going to be hard to convince me to change it. Why? Let’s start with these 3 reasons:

1. It’s close enough. We’re in the email business, in general, and Return Path is a good name for people in the industry to remember (it’s the first two words in every email header) for people in the industry, and it’s easy enough to say.

2. It has good equity. Almost five years in, most of our customers and industry watchers know it. Of course, it’s not Coke and has limited equity in the grand scheme of things, but its equity relative to the size of our enterprise is meaningful. That’s the important part. There’s a reason GE is still called GE even though its primary business is financial services now.

3. I have no idea what business we’re going to be in three years from now. Ok that’s an overstatement. I’m pretty sure we’ll still be in email. But while there are perhaps more appropriate names for us today, in today’s dynamic technology market, the company might look very different down the road, and changing a name is painful enough that I wouldn’t do it without a MAJOR event underway like a dramatic change of focus for the company, or a massive acquisition.

That said, if I had happened to name the company CompuTyco or EmailEnron, I’d change it because the collateral damage or risk thereof. If my mom had named me Adolph, Osama, or Saddam, I’d also be headed down to the courthouse to switch to a new one. They’re not as evil as a bad dictator of course, but Gator has so much baggage — they changed their own name to Claria!

So Greg, change that name despite the challenges outlined above. You’re lucky in that t’s still early enough for you. Just make sure you pick a new name that’s flexible and extensible into other areas in case the business you have in three years isn’t the business you have today. And don’t bother with an expensive naming consultant (let me know if you want to hear about that nightmare). Just have a good, structured brainstorm with your team.

Book Short: Chip Off the Old Block

I have to admit, I was more than a little skeptical when Craig Spiezle handed me a copy of The Speed of Trust, by Stephen M. R. Covey, at the OTA summit last week. The author is the son of THE Stephen Covey, author of the world famous Seven Habits of Highly Effective People as well as The Eighth Habit (book, post). Would the book have substance and merit or be drafting off the dad’s good name?

I dog-ear pages of books as I read them, noting the pages that are most interesting if I ever want to go back and take a quick pass through the book to remind me about it (and yes, Ezra, I can do this on the Kindle as well via the bookmark feature). If dog-ear quantity is a mark of how impactful a book is, The Speed of Trust is towards the top of the list for me.

The book builds nicely on Seven Habits and The Eighth Habit and almost reads like the work of Stephen the father. The meat of the book is divided into two sections: one on developing what Covey calls “self trust,” a concept not unlike what I blogged about a few months ago, that if you make and keep commitments to yourself, you build a level of self-confidence and discipline that translates directly into better work and a better mental state. The other core section is one on building trust in relationships, where Covey lists out 13 behaviors that all lead to the development of trust.

In fact, we just had a medium-size trust breach a couple weeks ago with one of our key clients. Reading the book just as we are struggling to “right the wrong” was particularly impactful to me and gave me a number of good ideas for how to move past the issue without simply relying on self-flagellation and blunt apologies. This is a book full of practical applications.

It’s not a perfect book (no book is), and in particular its notion of societal trust through contribution is a bit weak relative to the rest of the book, but The Speed of Trust is an excellent read for anyone who wants to understand the fastest way to build — and destroy — a winning culture. It reads like a sequel of Covey senior’s books, but that’s a good thing.

Techstars Roundup:  Why I Mentor Other Entrepreneurs

Yesterday was Demo/Investor day at Techstars in Boulder, Colorado.  A lot of people have written about it – Fred, Brad, and a great piece by Don Dodge on TechCrunch listing out all the companies.  My colleague George and I co-mentored two of the companies, SendGrid and Mailana, and we really enjoyed working with Isaac and Pete, the two entrepreneurs.

I posted twice earlier this summer on the TechStars experience.  My first post on this, Where do you Start?, was about whether to be methodical in business planning for a startup or dive right into the details.  My second post, One Pitfall to Avoid, was about making sure you don’t create a whizzy solution looking for a problem, but that you start with a problem that needs solving.

Rather than rehash what others have written about yesterday — yes, it was great and fun and energizing — I thought I’d focus on why I spend time mentoring new entrepreneurs.  I did it this year at TechStars, but I’ve done this informally for probably a dozen different entrepreneurs over the years in the community in general. 

Anyway, there are four main reasons I spend time mentoring other entrepreneurs (in no particular order):

It sharpens the saw.  This is Stephen Covey’s language from both The 7 Habits of Highly Effective People and The 8th Habit:  From Effectiveness to Greatness, and it simply refers to an activity that puls you out of the day to day and refreshes your brain because it’s different.  Running, playing guitar, mentoring sessions with entrepreneurs — they all clear the head and are just plain fun.

I get good specific ideas for my own business.  I think I came away from every single meeting I had with either entrepreneur this year with at least one new “to do” for myself and my team at Return Path.  There’s nothing quite like seeing how another company or entrepreneur operates to spur on good thinking, and in this case, both teams we worked with were working in the email space, so they were very relevant to our day-to-day.

I crystallize my own thoughts and ideas.  Much like writing this blog, problem/solution sessions with other entrepreneurs forces me to take a cloud of ideas down to a simple sentence or paragraph. 

I learn a lot about my colleagues.  This is a specific case for this year because I co-mentored these companies with George, although I guess bits and pieces of it have come up over the years as I’ve roped other colleauges into other situations.  George and I brought different ideas and frames of reference to our sessions with SendGrid and Mailana, and it was fun for me and a good learning experience as well to see how George approached the same problems I did.  Call it a “peek inside George’s brain.”

Hopefully I will get invited back to TechStars again next year as a mentor – it was great fun, and I’m incredibly proud of Pete and Isaac and their teams with how well they presented their companies yesterday!

Book Short:  Loving the Strengths Movement More Than the Book

I’m a big believer in the so-called Strengths Movement — that we would all be better served by playing to our strengths than agonizing over fixing our weaknesses. I think it’s true both in professional and personal settings.

The books written by Marcus Buckingham that come out of Gallup’s extensive research into corporate America, First, Break All the Rules (about management) and Now, Discover Your Strengths (self-management) are both quite good.  Another book written by someone else off the same research corpus, 12: The Elements of Great Managing is ok, but not as good, as I wrote about here.

Buckingham’s newest, Go Put Your Strengths to Work: 6 Powerful Steps to Achieve Outstanding Performance, is fine and has some good points but is way too long, a little hokey, and has a lot of online companion material that is far more interesting sounding than it is actually useful.

The book does build nicely on Now, Discover Your Strengths by giving you inspiration and a framework for taking those signature themes from the prior book and translating them into action — stuff you actually do every day that plays to your strengths and draws out your weaknesses.  And that’s helpful.  Some of his suggestions for what you do with that information are ok but a bit common sense only and way too drawn out (“here’s how to talk to your boss…”).

To be fair, I am going to do some of the work that Buckingham recommended doing — so I guess that says something about the power of the book, or at least the movement underlying it.  But not the best read in the world.

Book Short: The Joys of Slinging Hash

Patrick Lencioni’s The Three Signs of a Miserable Job is a good read, as were his last two books, The Five Temptations of a CEO (post, link), and The Four Obsessions of an Extraordinary Executive (post, link).  They’re all super short, easy reads (four express train rides on Metro North got the job done), with a single simple message and great examples.  This one is probably my second favorite so far.

This book, which has a downright dreary title, is great.  It points to and proposes a solution to a problem I’ve thought about for a long time, which is how do you create meaning for people in their day to day work when they’re not doing something intrinsically meaningful like curing a disease or feeding the homeless.  His recipe for success is simple:

– Get people to articulate the relevance in their jobs…the meaning they derive out of their work…an understanding of the people whose lives are made better, even in small ways, by what they do every day

– Get people to measure what they do (duh, management 101), IN RELATION TO THE RELEVANCE learnings from the last point (ahh, that’s an interesting twist)

– Get to know your people as people

All of these are things you’d generally read in good books on management, but this book ties them together artfully, simply, and in a good story about a roadside pizza restaurant.  It also stands in stark contrast to the book I reviewed and panned a few days ago by Jerry Porras in that it is nothing but examples from non-celebrities, non-success stories — ordinary people doing ordinary jobs.

Brad has blogged glowingly about Death by Meeting, so I’ll probably make that my next Lencioni read next month, with two more to go after that.