I was talking to a CEO the other day who believed it was “wrong” (literally, his word) to meet directly 1:1 with people in the organization who did not report to him.  I’ve heard from other CEOs in the past that they’re casual or informal or sporadic about this practice, but I’ve never heard someone articulate before that they actively stayed away from it.  The CEO in question’s feeling was that these meetings, which I call Skip-Level Meetings, disempowers managers.

I couldn’t disagree more.  I have found Skip-Level Meetings to be an indispensable part of my management and leadership routine and have done them for years.  If your culture is set up such that you as CEO can’t interact directly and regularly with people in your organization other than the 5-8 people who report to you, you are missing out on great opportunities to learn from and have an impact on those around you.

That said, there is an art to doing these meetings right, in ways that don’t disempower people or encourage chaos.  Some of these themes will echo other things I’ve written in recent posts like Moments of Truth and Scaling Me.  My five rules for doing Skip-Level Meetings are:

1. Make them predictable.  Have them on a regular schedule, whatever that is.  The schedule doesn’t have to be uniform across all these meetings.  I have some Skip-Levels that I do monthly, some quarterly, some once a year, some “whenever I am in town.”
   
2. Use a consistent format.  I always have a few questions I ask people in these meetings – things about their key initiatives, their people, their roadblocks, what I can do to help, what their POV is about the company direction and performance, how they are feeling about their role and growth.  I also expect that people will come with questions or topics for me.  If I have more meaty ad hoc topics, I’ll let the person know ahead of time.
   
3. Vary the location.  When I have regular Skip-Levels with a given person, I try to do the occasional one over a meal or drink to make it a little more social.  For remote check-ins, I now always do Skype or Videophone.
   
4. Do groups.  Sometimes group skip-levels are fun and really enlightening, either with a full team, or with a cross-section of skip-levels from other teams.  Watching people relate to each other gives you a really different view into team dynamics.
   
5. Close the loop.  I almost always check-in with the person’s manager BEFORE AND AFTER a Skip-Level.  Before, I ask what the issues are, if there is anything I should push on or ask.  After, I report back on the meeting, especially if there are things the person and I discussed that are out of scope for the person’s job or goals, so there are no surprises.

 I’m sure there are other things I do as well, but I can’t imagine running the company without this practice.  Doing it often and well EMPOWERS people in the company…I’d argue that managers who feel disempowered by it aren’t managers you necessarily want in your business unless you really run a command-and-control shop.

My dad (one of my main CEO/entrepreneur role models) and I team-teach a business school class in entrepreneurial leadership every year at USD where a friend of his is the professor.  Sometimes I go in person, usually I just do it by video.  We did this a few weeks ago, and my dad talked through a decision-making framework that I’d never heard him mention before.

I sketched it out and really like it and am already using it internally, so I thought I would share it here as well:

To walk through it, delegating decision-making to someone on your team can be as simple as understanding where a decision falls along two different spectrums.  On the vertical axis is “How familiar is the person with this type of decision?” – meaning, has the person seen and made this kind of decision before?  This could be something like firing an employee, signing a contract, negotiating a vendor agreement.  On the horizontal axis is “What are the consequences of getting the decision wrong?” – which is really self explanatory…how big a deal is this?

The primary, upper right quadrant of “The person has made this decision before, and it’s not a huge deal” is an easy one – delegate the decision-making authority.  The two middle quadrants of “big deal, but familiar with the decision” and “never seen this before, but not a big deal” are ripe for the old adage of ask forgiveness later, not permission first, meaning it’s ok to delegate decision-making authority, but hold the person accountable for letting you know about decisions like that so you can be on the lookout for potential required clean-up.

But what I love most is the way my dad framed the final quadrant (lower left here), which is “high stakes decision, never seen this situation before.”  It can be tempting for a senior manager or CEO to just take this quadrant over and remove decision-making authority from a team member.  But it’s also a perfect teaching/coaching moment.  So the rule of thumb for this quadrant is “make the decision with me, but please come to me with a proposal on it.”

And that’s why my dad is such a great business mentor!

Book Short – A Smattering of Good Ideas that further my Reboot path

Ram Charan’s The Attacker’s Advantage was not his best work, but it was worth the read.  It had a cohesive thesis and a smattering of good ideas in it, but it felt much more like the work of a management consultant than some of his better books like Know How (review, buy), Confronting Reality (review, buy), Execution (review, buy), What the CEO Wants You to Know ( buy), and my favorite of his that I refer people to all the time, The Leadership Pipeline (review, buy).

Charan’s framework for success in a crazy world full of digital and other disruption is this:

Perceptual acuity (I am still not 100% sure what this means)

1. A mindset to see opportunity in uncertainty
2. The ability to see a new path forward and commit to it
3. Adeptness in managing the transition to the new path
4. Skill in making the organization steerable and agile

The framework is basically about institutionalizing the ability to spot pending changes in the future landscape based on blips and early trends going on today and then about how to seize opportunity once you’ve spotted the future.  I like that theme.  It matches what I wrote about when I read Mark Penn’s Microtrends (review, buy) years ago.

Charan’s four points are important, but some of the suggestions for structuring an organization around them are very company-specific, and others are too generic (yes, you have to set clear priorities).  His conception of something he calls a Joint Practice Session is a lot like the practices involved in Agile that contemporary startups are more likely to just do in their sleep but which are probably helpful for larger companies.

I read the book over a year ago, and am finally getting around to blogging about it.  That time and distance were helpful in distilling my thinking about Charan’s words.  Probably my biggest series of takeaways from the book – and they fit into my Reboot theme this quarter/year, is to spend a little more time “flying at higher altitude,” as Charan puts it:  talking to people outside the company and asking them what they see and observe from the world around them; reading more and synthesizing takeaways and applicability to work more; expanding my information networks beyond industry and country; creating more routine mechanisms for my team to pool observations about the external landscape and potential impacts on the company; and developing a methodology for reviewing and improving predictions over time.

Bottom line:  like many business books, great to skim and pause for a deep dive at interesting sections, but not the author’s best work.

Book Short:  Scrum ptious 

I just finished reading Scrum: The Art of Doing Twice the Work in Half the Time, by Jeff Sutherland and JJ Sutherland. This reading was in anticipation of an Agile Facilitation training my executive team and I are going through next week, as part of Return Path’s  Agile Everywhere initiative. But it’s a book I should’ve read along time ago, and a book that I enjoyed.

Sutherland gets credit for creating the agile framework and bringing the concept scrum to software development over 20 years ago. The book very clearly lays out not just the color behind the creation of the framework, and the central tenets of practice again, but also clear and simple illustrations of its value and benefits.  And any book that employs the Fibonacci series and includes Theodore Roosevelt’s “Man in the Arena” quote — my all-time favorite — is off to a good start by me.

I’ve always appreciated a lot of the underlying philosophy of Agile, such as regularly checking on projects, course correcting in response to feedback from customers or other stakeholders, and working hard to remove any impediments to progress in real time.

One of the author’s most poignant points is that “multitasking makes you stupid.”  I hadn’t focused in the past how agile allows you to clear away context shifts to focus on one task at a time, but that’s another great take away from the book.

Our Agile Everywhere initiative, which is designed to improve productivity across the organization, as well as increase accountability through transparency, is even more critical in my view after having read this book.

The thing that I am left struggling with, which is still very much a work in progress for us, and hopefully something that we will address more head on in our training next week, is the application of the agile framework to teams that are not involved in the production of a tangible work product, such as executive or other leadership teams.  That is something that our Agile Everywhere deployment team has developed a theory about, but it still hasn’t entirely sunk in for me.

I can’t wait for next week’s training session!  If you have any experience applying the agile framework to different types of teams in your company I’d love to hear more about it in the Comments.

One of the things I’ve learned over the years is that as the organization scales, you have to be all-in, until you’re not.  What the heck does that mean?

It means that, other than confiding your indecision to a very small number of trusted advisors on a given issue, indecision is poison to the people around you and to the organization in general.  So even if you’re thinking of doing something new or different or making a tough call on something, you generally need to project confidence until you’ve made the call.

One example of this is around a decision to fire someone on the team, especially a senior executive.  Public indecision about this reminds me of years ago when George Steinbrenner owned the Yankees.  Every time he contemplated firing a manager, which was often, he was very public about it.  It turned the manager into a lame duck, ignored by players and mocked by the press.  No good for the manager or for the players, unhelpful for the team as a whole.  It’s the same in business.  Again, other than a small group of trusted advisors, your people have to have your full backing until the moment you decide to remove them.

Another example of this is a shift in strategy.  Strategy drives execution – meaning the course you chart translates into the goals and activities of all the other people in your organization.  Mobilizing the troops is hard enough in the first place, and it requires a tremendous amount of leadership expressing commitment.  If you’re contemplating a shift in strategy, which of course happens a lot in dynamic businesses, and you share your thinking and qualms broadly, you risk paralyzing the organization or redirecting activities and goals without intending to or without even knowing it.

Some people might look at this concept and cry “foul – what about Transparency?”  I don’t buy that.  As I wrote recently in The Difference Between Culture and Values, “When you are 10 people in a room, Transparency means you as CEO may feel compelled to share that you’re thinking about pivoting the product, collect everyone’s point of view on the subject, and make a decision together. When you are 100 people, you probably wouldn’t want to share that thinking with ALL until it’s more baked, you have more of a concrete direction in mind, and you’ve stress tested it with a smaller group, or you risk sending people off in a bunch of different directions without intending to do so. When you are 1,000 employees and public, you might not make that announcement to ALL until it’s orchestrated with your earnings call, but there may be hundreds of employees who know by then. A commitment to Transparency doesn’t mean always sharing everything in your head with everyone the minute it appears as a protean thought.  At 10 people, you can tell everyone why you had to fire Pat – they probably all know, anyway.  At 100 people, that’s unkind to Pat.  At 1,000, it invites a lawsuit.”

Book Short:  Best Book Ever

The Hard Thing About Hard Things, by Ben Horowitz, is the best business book I’ve ever read.  Or at least the best book on management and leadership that I’ve ever read.  Period.

It’s certainly the best CEO book on the market.  It’s about 1000 times better than my book although my book is intended to be different in several ways.  I suppose they’re complementary, but if you only had time left on this planet for one book, read Ben’s first.

I’m not even going to get into specifics on it, other than that Ben does a great job of telling the LoudCloud/Opsware story in a way that shows the grit, psychology, and pain of being an entrepreneur in a way that, for me, has previously only existed in my head.

Just go buy and read the book.

Lean In, Part II

My post about Sheryl Sandberg’s Lean In a couple months ago created some great dialog internally at Return Path.  It also yielded a personal email from Sheryl the day after it went up encouraging me to continue “talking about it,” as the book says, especially as a male leader.  Along those lines, since I wrote that initial post, we’ve had a few things happen here that are relevant to comment on, so here goes.

We partnered  with the National Center for Women & IT to provide training to our entire organization on unconscious bias.  We had almost 90% of the organization attend an interactive 90 minute training session to explore how these biases work and how to discuss these issues with others.   The goals were to identify what unconscious bias is and how it affects the workplace, identify ways to address these barriers and foster innovation, and provide practice tools for reducing unconscious biases.   While the topic of unconscious bias in the workplace isn’t only about gender, that’s one major vector of discussion.  We had great feedback from across the organization that people value this type of dialog and training.  It’s now going to be incorporated into our onboarding program for new employees.

Second, as I committed to in my original post, we ran a thorough gender-based comp study.  As I suspected, we don’t have a real issue with men being paid more than women for doing the same job, or with men and women being promoted at different rates.    That’s the good news.  However, the study and the conversations that we had around it yielded two other interesting conclusions.  One is that that we have fewer women in senior positions than men, though not too far off our overall male:female ratio of 60:40.  On our Board, we have no women.  On our Executive Committee, we have 1 of 10 (more on this below).  On our Operating Committee, we have 8 of 25.  Of all Managers at the company, we have 32 of 88.  So women skew to more junior roles.

The other is that while we do a good job on compensation equity for the same position, it takes a lot of deliberate back and forth to get to that place.  In other words, if all we did was rely on people’s starting salaries, their performance review data, and our standard raise percentages, we would have some level of gender-based inequality.  Digging deeper into this, it’s all about the starting point.  Since we have far more junior/entry level women than men, the compensation curve for women ends up needing to be steeper than that of men in order to level things out.  So we get to the right place, but it takes work and unconventional thinking.

Finally, I had an enlightening process of recruiting two new senior executives to join the business in the past couple of months.   I knew I wanted to try and diversify my executive team, which was 25% female, so I made a deliberate effort to focus on hiring senior women into both positions.  I intended to hire the best candidate, and knew I’d only see male candidates unless I intentionally sourced female candidates.  For both positions, sourcing with an emphasis on women was VERY DIFFICULT, as the candidate pools are very lopsided in favor of men for all the reasons Sheryl noted in her book.  But in both cases, great female candidates made it through as finalists, and the first candidate to whom I offered each job was female – both superbly qualified.  In both cases, for different reasons I can’t go into here, the candidates didn’t end up making it across the finish line.  And then in both cases, when we opened up the search for a second round, the rest of the candidate pool was male, and I ended up hiring men into both roles.  Now my resulting exec team is even more heavily male, which was the opposite of my intention.  It’s very frustrating, and it leaves us with more work to do on the women-in-leadership topic, for sure.

So…some positives and some challenges the last few months on this topic at Return Path.  I’ll post more as relevant things develop or occur.  We are going to be doing some real thinking, and probably some program development, around this important topic.

(This is the second in a series of three posts on this topic.)

In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them.

Selecting a CEO Mentor is literally like selecting a teacher but at a vocational school, not at a research university.  You want to select someone who has done something several times or for several years; done it really well; documented it in some organized way (at least mentally); and can articulate what they did, why, what worked and what didn’t, and help you apply it to your situation.  Do you want to be taught how to be an electrician by someone with a PhD in Electrical Engineering, or by someone who has been a master electrician for 20 years?   Fit matters mostly around values.  It’s hard to get advice from someone whose values are quite different, as their experiences and their metrics for what did and didn’t work won’t apply well to yours.  Fit is a lot less around personality, although you have to be able to get along and communicate with the person at a basic level  Find someone with the right experience set that you can learn from RIGHT NOW.  Or at least this year.  Maybe the person is the right mentor next year, maybe not.  Depends on what you need.  For example, if you’re running a $10mm revenue DTC company, find someone who has scaled a company in the DTC or adjacent eCommerce space to at least $25-50mm. 

Although I’ve been very international in getting mentoring as a CEO over the years, I’ve never hired a formal CEO Mentor. Several people, from my dad to my independent directors to the members of my CEO Forum have played that role for me at different times over the years. Knowing what I know now, I’m working with CEO Mentors who have experience with talent marketplaces at different scale, since this is a new industry for me.

Selecting a CEO Coach is different.  I got lucky in my selection of a CEO Coach almost 20 years ago.  My board member Fred Wilson told me I needed to work with one, I naively rolled my eyes and said ok, he introduced me to Marc Maltz, I told Marc something like “I need a coach because clearly I need to learn how to manage my Board better,” and for some reason, he decided to take the assignment.  I got lucky because Marc ended up being exactly the right coach for me, going on 20 years now, but I didn’t know that at the time.  

Selecting a CEO Coach is all about who you “click with” personality wise, and what you need in order to be pushed to grow developmentally.  CEO Coaches come on a spectrum ranging from what I would call “Quasi-Psychiatrist” on one end, to “Quasi-Management Consultant” on the other end.  The former can be incredibly helpful — just note that you will find yourself talking about your thoughts, feelings, and family of origin a fair bit as a means of uncovering problems and solutions.  The latter can be helpful as well — just note that you will find yourself talking about business strategy and having someone hold up the proverbial mirror so you can see you the way other people see you as the CEO, quite a bit.  There is no right or wrong universal answer here to what makes someone the right choice for you.  For me, if one end of the spectrum is a 1 and the other is a 5, I prefer working with people who are in the 3-4 range.  

Therapy and coaching are different, though.  A good CEO Coach who is a 1 will refer clients to therapy if they see the need. While coaching can “feel” therapeutic, and actually may be therapeutic, it is not a replacement for therapy. The differences between the 1s and the 5s are not just style differences but also really what you want the content of the coaching to be.  A 1 is going to help you discover and drive to your leadership style.  A 5 is going to help you align those decisions to how you actually act, what approaches you bring to the organization and how you address challenges.  Some CEO Coaches can move back and forth between all of these, but knowing where you sit with your needs relative to the coach’s natural style when you pick a coach is critical.

I know CEOs who have shown tremendous growth as humans and leaders with Coaches who are 1s and Coaches who are 5s.  A good CEO Coach is someone you can work with literally forever.   

I always encourage CEOs to interview multiple Coaches and specifically ask them what their coaching process is like and what their coaching philosophy is.  How do they typically start engagements.  How structured or unstructured are they in their work?  Check references and ask some of their other CEO clients what it’s been like to work with them.  This is all true to a much lesser extent with Mentors.  In both cases, you should probably do a test session or two before signing up for a longer-term engagement.  You wouldn’t buy a car without taking it for a test drive.  This is an even more consequential decision.  

And in both cases, there should be no ego in the process.  You should never feel like you’re being sold by a CEO Coach or CEO Mentor.  And they shouldn’t feel hurt by you picking someone else, either.  Alignment and chemistry are so critical – there is no way to have that with every person, and the good professionals in this industry should know that.

The bottom line is that hiring a CEO Mentor is low risk. If it’s not working out, you stop engaging. Hiring a CEO Coach is a longer-term decision, and it’s worth having couple of sessions with a coach before making the commitment.

Next post in the series coming:  How to get the most out of working with a CEO Mentor or CEO Coach 

Jim Collins, in both Good to Great and Built to Last talked about the BHAG – the Big, Hairy Audacious Goal – as one of the drivers of companies to achieve excellence.  Perhaps that’s true, especially if those goals are singular enough and simplified enough for an entire company of 100-1000-10000 employees to rally around.

I have also observed over the years that both star performers and strong leaders drive themselves by setting large goals.  Sometimes they are Hairy or Audacious.  Sometimes they are just Big.  I suppose sometimes they are all three.  Regardless, I think successfully managing to and accomplishing large personal goals is a sign of a person who is driven to be an achiever in life – and probably someone you want on your team, whether as a Board member, advisor, or employee, assuming they meet the qualifications for the role and fit the culture, of course.

I’m not sure what the difference is between Hairy and Audacious.  If someone knows Jim Collins, feel free to ask him to comment on this post.  Let’s assume for the time being they are one and the same.  What’s an example of someone setting a Hairy/Audacious personal goal?  My friend and long-time Board member Brad Feld set out on a quest 9 years ago to run a marathon in each of the 50 states by the age of 50.  Brad is now 9 years in with 29 marathons left to go.  For those of you have never run a marathon (and who are athletic mortals), completing one marathon is a large, great and noteworthy achievement in life.  I’ve done two, and I thought there was a distinct possibility that I was going to die both times, including one I ran with Brad .  But I’ve never felt better in my life than crossing the finish tape those two times.  I’m glad I did them.  I might even have another one or two in me in my lifetime.  But doing 50 of them in 9 years?  That’s a Hairy and Audacious Goal.

For me, I think the Big goal may be more personally useful than the Hairy or Audacious.  The difference between a Big goal and a Hairy/Audacious one?  Hard to say.  Maybe Hairy/Audacious is something you’re not sure you can ever do, where Big is just something that will take a long time to chip away at.  For example, I started a quest about 10-12 years ago to read a ton of American history books, around 50% Presidential biographies, from the beginning of American history chronologically forward to the present.  This year, I am up to post-Civil War history, so roughly Reconstruction/Johnson through Garfield, maybe Arthur.  I read plenty of other stuff, too – business books, fiction, other forms of non-fiction, but this is a quest.  And I love every minute of it.  The topic is great and dovetails with work as a study in leadership.  And it’s slowly but surely making me a hobby-level expert in the topic.  I must be nearing Malcolm Gladwell’s 10,000 hours by now.

The reason someone sets out on a personal quest is unclear to me.  Some people are more goal-driven than others, some just like to Manage by Checklist, others may be ego-driven, some love the challenge.  But I do think that having a personal quest can be helpful to, as Covey would say, Sharpen the Saw, and give yourself something to focus personal time and mental/physical energy on.

Just because someone isn’t on a personal quest doesn’t mean they’re not great, by the way.  And someone who is on a quest could well be a lunatic.  But a personal quest is something that is useful to look for, interesting and worth learning more about if discovered, and potentially a sign that someone is a high achiever.

(Excerpted from Chapter 12 of Startup CEO)

As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things:

1. Asking for feedback
2. Accepting feedback gracefully
3. Acting on feedback
4. Asking for follow‐up feedback on the same topic to see how you did

In some respects, asking for it is the easy part, although it may be unnatural. You’re the boss, right? Why do you need feedback? The reality is that all of us can always benefit from feedback. That’s particularly true if you’re a first‐time CEO. Even more experienced CEOs change over time and with changing circumstances. Understanding how the board and your team experience your behavior and performance is one of the only ways to improve over time. It’s easier to ask for feedback if you’re specific. I routinely solicit feedback in the major areas of my job (which mirror the structure of this book):

Strategy. Do you think we’re on target with what we’re doing? Am I doing a good enough job managing to our goals while also being nimble enough to respond to the market?

Staff management/leadership. How effective am I at building and maintaining a strong, focused, cohesive team? Do I have the right people in the right roles at the senior staff level?

Resource allocation. Do I do a good enough job balancing among competing priorities internally? Are costs adequately managed?

Execution. How do the team and I execute versus our plans? What do you think I could be doing to make sure the organization executes better?

Board management/investor relations. Do you think our board is effective and engaged? Have I played enough of a role in leading the group? Do you as a director feel like you’re contributing all you can? Do I strike the right balance between asking and telling? Are communications clear enough and regular enough?

Accepting feedback gracefully is even harder than the asking part. You may or may not agree with a given piece of feedback, but the ability to hear it and take it in without being defensive is the only way to make sure that the feedback keeps coming. Sitting with your arms crossed and being argumentative sends the message that you’re right, they’re wrong, and you’re not interested. If you disagree with something that’s being said, ask questions. Get specifics. Understand the impact of your actions rather than explaining your intent.

The same logic applies to internalizing and acting on the feedback. If you fail to act on feedback, people will stop giving it to you. Needless to say, you won’t improve as a CEO. Fundamentally, why ask for it if you’re not going to use it? And that leads right into the fourth point, closing the loop with the person who gave you feedback on whether or not your actions achieved the desired change.

(This is the second post in the series… the first one When to Hire your first Chief Privacy Officer is here)

Most Chief Privacy Officers are fairly specialized, often coming from a legal or law enforcement background, but regardless of background I’ve found that ideal startup Chief Privacy Officers do three things particularly well.

First, a great Chief Privacy Officer will work to create educated evangelists inside the company.  Our Privacy team at Return Path, under Dennis Dayman’s leadership, had a lot of experience and industry certifications, but that experience was not something only for regulators and other companies, or only bragging rights within their team. They also took the time to make sure others in the company, especially in the product management and engineering teams, received some of that same training and those same certifications.  By not making the Privacy team a single point of knowledge or failure, Dennis was able to make Privacy part of our product strategy and offense as opposed to a mitigation or defensive function

A second ideal characteristic of a Privacy Officer is that they also handle the basics of InfoSec, in addition to privacy.  If you’re actually a security-related company or a massive consumer or financial organization, you may need a dedicated Chief Information Security Officer.  If you aren’t, then a good Chief Privacy Officer should be able to handle a number of the functions that a CISO would otherwise handle, especially on the policy and communication front.

And third, a great Chief Privacy Officer is an excellent communicator, both internally and externally, and they help connect you to the relevant members of your community or ecosystem.  When we had a sizable data breach on Thanksgiving Day about 10 years ago, our fractional head of privacy, Tom Bartel, was on the spot. He wrote emails and external blog posts that needed almost no review.  He was also instantly communicating with dozens of his counterparts at related companies so that the industry knew where we stood and what we were doing about the problem.  It was like an instant activation of an emergency response system!

Don’t wait until you have a data breach to hire a great Chief Privacy Officer because by the time you need one it will be too late.

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