Nov 122015

You Have To Be All In, Until You’re Not

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.”

Sep 172015

The Playbook

As Return Path gets older, we are having more and more alums go on to be successful senior executives at other companies – some in our space, some not.  It’s a great thing, and something I’m really proud of.  I was wondering the other day if there’s effectively some kind of “RP Playbook” that these people have taken with them.  Here’s what I learned from asking five of them.

People-related practices are all prominent as part of the Playbook, not surprising for a People First company.  Our Peer Recognition program, which is almost as old as the company and has evolved over time, was on almost everyone’s list.  Open Vacation is also part of the mix, as was a focus on getting Onboarding right so new employees start off on the right foot.  Live 360s were on multiple lists, too, as were Skip-Level 1:1s.

Beyond People-related programs, though, there was general agreement among the five that the mentality of trust in management was something they brought with them in this mythical Playbook.  Specific examples include fostering a culture of idea sharing, having difficult conversations, driving as much self-management as possible, focusing on managing high performers as opposed to spending all our cycles on managing low performers, balancing freedom and flexibility with performance and accountability, and going above and beyond and bending rules for sick employees and their families.

Connections and networking – both internal and external – made the cut as well.  A lot of those, especially external ones, are used to foster benchmarking, best practices sharing, and “leveling up” to help teams and organizations scale by learning from others.

Finally, there were some specific execution-related Playbook items from establishing a vision, to translating it into goals and fostering alignment across the organization, to instituting processes and systems instead of throwing bodies at problems.  One important element of execution cited is the importance of giving new and existing managers the tools to grow as the company grows.

This is hardly an exhaustive Playbook and unscientific in its construction, but I thought the “top of mind” answers from five senior people I respect was an interesting list and probably the beginning of something broader.

Thanks to the following friends for their contributions to this post:  Jack Sinclair, CFO of Stack Overflow; Angela Baldonero, SVP Human Resources for Kimpton Hotels; Tom Bartel, CEO of ThreatWave; Chad Malchow, CRO for Gitlab; and Dennis Malaspina, CRO for Parsley.

Aug 272015

The Joy of Coaching

I was the head coach of my two older kids’ little league team this past spring.  The whole thing was a little bit of an accident – I vaguely volunteered for something and ended up in charge.  The commitment was a little daunting, but I was ok with it since the season was only a couple months long, it was both Casey and Wilson, and both kids, especially Wilson, are really into baseball.  Other than helping out a bit here and there, I’d never coached a sports team before.

What started off as an unclear assignment ended up as one of the most fun and fulfilling things I’ve done in years.  I loved every minute of it, looked forward to our practices and games, was hugely bummed out when we got rained out, and never had a moment where I couldn’t make the time for it (though clearly the hours had to come from somewhere!).  Given some of the overlap between leading a sports team and leading a company, I thought I’d reflect on the experience a bit here.  There are some common themes between this post and something I wrote years ago, Parenting and Corporate Leadership, with the same caveat that no, I don’t think employees are children or children are employees.  But here are some things I take away from the experience and apply or compare to work.

We established a clear philosophy and stuck to it.  That’s a step that lots of coaches – and managers in the workplace – miss.  The other coaches and I discussed this before the first practice, agreed on it, and shared it directly with the kids.  For this age group in particular, we felt that we were there first and foremost to have fun; second to learn the game; and third, to play hard and fair.  Note there was nothing in this about winning, and that we were really specific about the order of the three objectives.  Even 7 and 8 year olds know the difference between “win at all costs” and “have fun and play ball.”  We reinforced this at every practice and at every game.  Being intentional about a philosophy and communicating it (and of course sticking to it) are key for any leadership situation.

We got lucky.  As I repeatedly said to the parents on the team, we had a group of awesome kids – happy and generally paying attention, and not one troublemaker in the bunch; and we had a group of awesome parents – responsive, supportive, and not a single complaint about what position a kid was playing or where someone was in the batting order.  I’d heard horror stories about both kids and parents from other coaches ahead of time.  It’s possible that the other coaches and I did such a good job that both kids and parents were great all the time…but I think you have to chalk most of that up to the luck of the draw.  Work isn’t all that different.  Having stakeholders who are consistently positive forces is something that sometimes you can shape (you can fire problematic employees) but often you can’t, in the case of customers or even Board members.  Luck matters.

Stakeholder alignment was a critical success factor.  Having said that, I do think the coaches and I did a good job of keeping our stakeholders aligned and focusing on their needs, not ours.  We put extra effort into a regular cadence of communication with the parents in the form of weekly emails and a current web site.  We used those emails to highlight kids’ performance and also let parents know what we’d be working on in practice that week.  We made sure that we rotated kids in the batting order so that everyone got to bad leadoff once and cleanup once.  We rotated kids so that almost every kid played half of each game in the infield and half in the outfield.  We took any and all requests from kids who wanted to play a specific position for a few innings.  Many of these basic principles – communicating well, a clear operating system, listening to stakeholders, a People First approach – are lessons learned from work as a CEO.

Proper expectations and a large dose of patience helped.  After the first couple games, we were 0-2, and I was very frustrated.  But I reminded myself that 7 and 8 year olds are just kids, and my frustration wasn’t going to help us achieve our objectives of having fun and learning the game.  So I recalibrated my expectations and took much more of a laid-back attitude.  For example, any time I saw one kid goofing off a little bit in practice, I gently got him or her back in line.  But when I saw multiple kids’ attention fading, I took it as a sign that whatever I was doing as a coach wasn’t working, called a break, and did something else.  This kind of “look in the mirror” approach is always helpful at work, too.

Reward and recognition were key.  We definitely adopted a Whale Done! approach with the kids.  We got the kids in the dugout fired up to cheer on batters.  First base coaches did big high fives, smiles, and literal pats on the back for every hit.  Post-game huddles and emails to parents focused on highlights and what went right for the kids.  One of my favorite moments of the season was when one player, who only had one hit all year and struck out almost every time at bat, had two hits, an RBI, and a run scored in our final game.  Not just the coaches, but the other kids and all the parents went absolutely BANANAS cheering for this player, and it brought huge smiles to all our faces.  I am 100% certain that the focus on the positive encouraged the kids to try their hardest all season, much as I believe that same philosophy encourages people to take risks and work hard at the office.

The biggest thing I take back to the workplace with me from the experience.  I was reminded about how powerful achieving a state of “flow,” or “relaxed concentration” is.  I recounted these principles in this blog post from a couple different books I’ve read over the years – Mihaly Csikszentmihalyi’s Flow and Tim Gallway’s Inner Game books – Golf, Tennis, and Work.  The gist of achieving a state of flow is to set clear goals that are stretch but achievable, become immersed in the activity, pay attention to what’s happening, and learn to enjoy immediate experience.  All leaders – in sports, business, or any walk of life – can benefit from this way of living and leading.

I loved every minute of coaching.  It helped that we ended up with a really strong record.  But more than that, building relationships with a bunch of great kids and great parents was fun and fulfilling and incredibly thankful and rewarding.  The “thank you ball” that all the kids autographed for me is now a cherished possession.  Working and getting extra time with my own two kids was the icing on the cake.  All I want to know is…is it time for next season yet?  I am ready!

This post is really for Coaches Mike, Paul, and Oliver; and players Emily, Casey, Lauryn, Mike, Josh, Holden, Hudson, Wilson, Drew, Kevin, Matthew, and Christian.

Apr 292015

ReturnShip Program, Part II

Today marks the graduation for the six women who participated in our inaugural ReturnShip program, which I wrote about here and which was written up at least twice, in Harvard Business Review and in the San Francisco Chronicle.

The ReturnShip was a 14-week paid internship program designed for women who have been out of the workforce for more than 1 year to re-enter and  build credible and relevant experience, and to feed our funnel of prospective employees.

While there are still a couple things in the air, my guess is that at least three, and as many as five, of the program’s six participants, will continue their work at Return Path, either full time, part time, or as a contractor.  For many people who are returning to the workforce but still have full-time jobs at home, flexibility is the key.

The program was a huge success for us as a company, for the teams who worked with our six returnees, and I believe for the returnees as well.  We are already in the planning stages of the next wave of the program, potentially as early as this fall, where we’d like to expand the scope of the program in terms of departments covered, number of returnees, and geographies.  We learned a huge amount about, well, lots of things, from the last 14 weeks, and we’ll apply those learnings to the next wave.

I hope this work inspires other companies to do something similar, and we’d be happy to inspire anyone who wants to talk about it with us.  Most of all, I want to thank our six returnees, the managers who worked with them, and our People Team for being part of a bold and successful experiment.

Sep 252014


Post Traumatic Job Disorder.

As we have been scaling up Return Path, we have been increasingly hiring senior people in from the outside. We believe in promoting from within and do it all the time, but sometimes you need an experienced leader who has operated at or ahead of the scale you’re at.  Someone with deep functional expertise and a “been there, done that” playbook. When you get a hire like this right, it’s amazing how much that kind of person gets done, how quickly.

One of the pitfalls of those hires, though, is cultural fit. Many of the larger organizations in the world don’t have the kind of supportive, employee-centric cultures that we have here, or that startups tend to have in general. They tend to be much more hierarchical, political, command-and-control. There is a real risk that hiring a senior person who has been trained in environments like that will blow up on you — that, as I’ve written before, the body will reject the organ transplant.

I’ve taken to calling the problem PTJD, or Post-Traumatic Job Disorder. Some of the stories I’ve heard from senior people about their experiences with their bosses or even CEOs at prior companies include such things as:  being screamed at regularly, having had a gun pulled on you, having had a knife pulled on you, having been ignored and only spoken to once or twice a year, being the victim of sexual harassment. Nice.

Just like PTSD, many people can recover from PTJD by being placed in a different environment with some up-front reprogramming and ongoing coaching. But also like PTSD, there are times where people can’t recover from PTJD. The bad habits are too engrained. They are (virtually) shell shocked.

Assuming you do the same reprogramming and coaching work on any PTJD employee, the difference between an employee who recovers and one who does not recover is really hard to smoke out in an interview process. Almost all candidates like this (a) are very polished and now how to interview well, and (b) genuinely think they want to work in a more relaxed, contemporary environment.

Here are five things I’ve learned over the years that can help identify a PTJD candidate who is unlikely to recover, before you make the hire:

  1. Look for candidates who have bigger company experience, but who also have startup and growth/scaling experience.  As I’ve written before, stage experience is important because the person is more likely to really understand what he or she is getting into — and what their playbook of action is.
  2. Try to understand, if a candidate has been in a workplace that breeds PTJD, whether that person was just in the machine, or if the person actually ran the machine. In other words, a senior manager might be a better fit to recover from PTJD than a senior executive.
  3. Note that not all big companies are dysfunctional or lead to PTJD, so try to understand the reputation of the person’s employer. For example, in New York, it’s a pretty safe bet that someone coming from American Express has not only been well trained, but well cared for.
  4. Do reference checks differently. Do them yourself. Do them as if you were doing a 360 on the person (manager, peer, subordinate, even a junior person from another department). Do reference checks on the references (seriously – ask the references about each other) so you understand the biases each of them brings to the conversation with you.
  5. Focus on the first 90 days. Be relentless about how you onboard a potential PTJD victim. Give them more care, structure, praise, guidance, and criticism than you might otherwise give. Use an outside coach to augment your work, and assign a good executive buddy internally. And listen carefully to the feedback from the organization about the person, doing a deep 360 after a few months to see if the person is recovering, can recover, or can’t recover. If the latter, time to cut your losses early.

Thanks to some of my new executive colleagues here for inspiring this post, and I hope none of my friends who have served in the military take offense at this post. I am drawing an analogy, but I’m not truly suggesting that PTJD compares in any way, shape, or form to the horrors of war.

Sep 112014

The 2×4

The 2×4

I took a Freshman Seminar in my first semester at Princeton in 1988 with a world-renowned professor of classical literature, Bob Hollander.  My good friend and next-door neighbor Peggy was in the seminar with me.  It was a small group — maybe a dozen of us — meeting for three hours each week for a roundtable with Professor Hollander, and then writing the occasional paper.  Peggy and I both thought we were pretty smart.  We had both been high school salutatorians from good private schools and had both gotten into Princeton, right?

Then the first paper came due, and we were both a bit cavalier about it.  We wrote them in full and delivered them on time, but we probably could have taken the exercise more seriously and upped our game.  This became evident when we got our grades back.  One of us got a C-, and the other got either a D or an F.  I can’t remember exactly, and I can’t remember which was which.  All I remember is that we were both stunned and furious.  So we dropped by to see Professor Hollander during his office hours, and he said the same thing to each of us:  “Matt, sometimes you need a 2×4 between the eyes.  This paper is adequate, but I can tell it’s not your best work, it’s decent for high school but not for college, and almost all the others in the class were much more thoughtful.”


Ever since then, Peggy and I have talked about the 2×4, and how it helped us snap out of our own reality and into a new one with a significantly higher bar for quality.  That phrase made it into Return Path‘s lexicon years ago, and it means an equivalent thing — sometimes we have to have hard conversations with employees about performance issues.  The hardest ones are with people who think they are doing really well, when in reality they’re failing or in danger of failing.  That disconnect requires a big wakeup call — the 2×4 between the eyes — before things spiral into a performance plan or a termination.

Delivering a 2×4 between the eyes to an employee can feel horrible.  But it’s the best gift you can give that employee if you want to shake them back onto a successful trajectory.

Aug 282014

Physical Therapist or Chiropractor?

Physical Therapist or Chiropractor?

I was talking to a good friend the other day who is an executive coach. He was telling me that his clients are all over the map in terms of role (CEO or functional senior exec), need (small issue to large issue), company size and stage. But most important, he noted that his clients have different ways of learning, and that he has to tailor his coaching style to the client.

I had two main takeaways from this interaction.

First, he had a particularly memorable way of phrasing the differences in client learning styles that inform his approach. Some of his clients, he noted, need a physical therapist. They need someone to work with them every week, using whatever issues that come up that week as a means of stretching and building muscles. Other clients need a chiropractor. They are all good but once in a while need to stop by for him to wrench their spine for a few minutes and get things back in line. This is a brilliant metaphor.

Second, for anyone who manages, coaches, or mentors out there, if you can’t tailor your style to meet the needs of your direct reports or mentees, you aren’t being as effective as possible. We all learn and work in different ways. Good management isn’t ramming a set style down people’s throats. It’s getting the most out of people given who they are. I wrote a bit about this years ago and it’s still so true.

Filed under: Leadership, Management

Aug 142014

How to Manage Your Career

I gave a presentation to a few hundred Return Path employees in January at an all-hands conference we did called “How to Manager Your Career.”

The presentation has three sections — The Three Phases of a Career, How to Get Promoted, and How to Wow Your Manager.

While it’s not as good without the voiceover and interactivity, I thought I’d post it here…see the presentation on Slideshare.

As I said to my audience, if there’s one thing to take away from the topic, it’s this:

Managing your career is up to one, and only one person – you. 

It doesn’t matter how great a corporate culture you have, or how supportive your manager is.  You’re the only person who cares 100% of the time about your career, and you’re the only person with a longitudinal view of what you love, what you’re great at, where you’ve been, and where you want to go.

Jul 172014

The Gift of Feedback, Part IV

The Gift of Feedback, Part IV

I wrote a few weeks ago about my live 360 – the first time I’ve ever been in the room for my own review discussion.  I now have a development plan drafted coming out of the session, and having cycled it through the contributors to the review, I’m ready to go with it.  As I did in 2008, 2009, and 2011, I’m posting it here publicly.  This time around, there are three development items:

  1. Continue to spend enough time in-market.  In particular, look for opportunities to spend more time with direct clients.  There was a lot of discussion about this at my review.  One director suggested I should spend at least 20% of my time in-market, thinking I was spending less than that.  We track my time to the minute each quarter, and I spend roughly 1/3 of my time in-market.  The problem is the definition of in-market.  We have a lot of large partners (ESPs, ISPs, etc.) with whom I spend a lot of time at senior levels.  Where I spend very little time is with direct clients, either as prospects or as existing clients.  Even though, given our ASP, there isn’t as much leverage in any individual client relationship, I will work harder to engage with both our sales team and a couple of larger accounts to more deeply understand our individual client experience.
  2. Strengthen the Executive Committee as a team as well as using the EC as the primary platform for driving accountability throughout the organization.  On the surface, this sounds like “duh,” isn’t that the CEO’s job in the first place?  But there are some important tactical items underneath this, especially given that we’ve changed over half of our executive team in the last 12 months.  I need to keep my foot on the accelerator in a few specific ways:  using our new goals and metrics process and our system of record (7Geese) rigorously with each team member every week or two; being more authoritative about the goals that end up in the system in the first place to make sure my top priorities for the organization are being met; finishing our new team development plan, which will have an emphasis on organizational accountability; and finding the next opportiunity for our EC to go through a management training program as a team.
  3. Help stakeholders connect with the inherent complexity of the business.  This is an interesting one.  It started out as “make the business less complex,” until I realized that much of the competitive advantage and inherent value from our business comes fom the fact that we’ve built a series of overlapping, complex, data machines that drive unique insights for clients.  So reducing complexity may not make sense.  But helping everyone in and around the business connect with, and understand the complexity, is key.  To execute this item, there are specifics for each major stakeholder.  For the Board, I am going to experiment with a radically simpler format of our Board Book.  For Investors, Customers, and Partners, we are hard at work revising our corporate positioning and messaging.  Internally, there are few things to work on — speaking at more team/department meetings, looking for other opportunities to streamline the organization, and contemplating a single theme or priority for 2015 instead of our usual 3-5 major priorities.

Again, I want to thank everyone who participated in my 360 this year – my board, my team, a few “lucky” skip-levels, and my coach Marc Maltz.  The feedback was rich, the experience of observing the conversation was very powerful, and I hope you like where the development plan came out!

Apr 242014

Breaking New Ground on Transparency

Breaking New Ground on Transparency

I’ve written a lot over time about our Live 360 process for senior leaders in the business.  (This post is a good one, and it links to a couple earlier ones that are good, as well.)  We take a lot of pride in feedback and in transparency at Return Path, and after 15 years, even for an innovative business, it’s unusual that we do something big for the first time around people.  But we did today.

This image is of something never seen before at our company.  It’s my own handwritten notes about my own Live 360.

360 notes

It’s never been seen before, because no one has ever been physically present for his or her own review before.  In previous reviews, my Board, my exec team, and a few skip-levels gather in a room for 90 minutes with a facilitator to discuss my performance and behaviors.  Then the facilitator would go away and write up notes, and discuss them with me, then I’d produce a development plan.

Today, we decided to experiment with having me sit in my own review to add to the transparency and directness of the feedback.  My only role was to listen, ask (non-judgmental) clarifying questions, and take notes.  I left the room at the end in case someone wanted to say something without me hearing it directly, but although the conversation about the business continued, it didn’t sound like there was anything material about me that surfaced.

It was a little awkward at first, and it was interesting that some people addressed me directly while others spoke of me in the third person.  But once we got past that, the experience was incredibly powerful for me.  The first part — the “what do you appreciate about Matt” part — was humbling and embarrassing and gratifying all at the same time.

The meat of the review, though — the “how can we coach Matt on areas where he needs development” — was amazing.  I got great insights into a couple of major areas of work that I need to do, and that we need to do as a business.  I’m guessing I would have gotten them out of reading a summary of the review conversation, but hearing the texture of the conversation was much, much richer than reading a sanitized version of it on paper.  As always with reviews, there was the odd comment or two that annoyed me, but I felt like I handled them well without any defensive body language or facial expressions.

I will, as I’ve always done, post my development plan to my blog after I formulate it over the course of the next few weeks.  But for now, I just want to thank my Board and team for their awesomely constructive feedback and for helping us usher in a new era of increased transparency here.