In 2005, I wrote a post called Unfolding the Map in which I looked at these two seemingly opposing philosophies from successful entrepreneurs:

• If you don’t have a map, you can’t get lost
• If you don’t have a map, you can’t get where you’re going

and tried to combine them when thinking about product roadmapping. The same contradiction and combination could be applied to anything, including coaching and development.

That’s why I was excited to read my friend Matt Spielman’s new book, Inflection Points: How to Work and Live with Purpose. Matt worked at Return Path twice over the years — first as employee #3 (more on that in a minute) and then over a decade later as CMO. We live near each other and know each other’s families. I’ve been lucky enough to see his career unfold and develop into what it is today, a flourishing coaching business called Inflection Point Partners that helps clients tremendously…and that also feeds Matt’s soul.

When I first met Matt and he joined me and Jack to launch Return Path in 1999, he was fresh out of business school and focused on sales and marketing from his prior career in investment banking. Our idea was that he would do the same for us as we got our product in market. But as I started focusing more on what kind of company we wanted to build and how to get there, Matt became my leading thought partner on those topics. When we got to about 25 people, he and I created a new role for him — head of Human Capital and Organization Development. While a bit clunky, that title meant that Matt was the principal person helping me create at small scale what we later branded our People First philosophy. That philosophy and the practices we developed out of it led to 20 years of a strong track record of investing in people and helping over 1,300 colleagues grow their careers by being simple, actionable, and broad-based in the way we handled feedback and development planning. This started back in 2000.

Matt’s book puts the ethos that I saw percolating over 20 years ago into a tight framework around his coaching methodology of the GPS (Game Plan System). The book is short and sweet and walks through both the philosophy and the framework in accessible terms. And while it’s true that you have to be open to new ideas, open to serendipity, and go with flow sometimes…it’s also true that if you have specific goals in mind, you are unlikely to achieve them without a focused effort.

I’ve written a lot about coaching lately between The Impact of a Good Coach and another recent post about a strong coaching framework about intentionality in Russell Benaroya’s book. In that second post, I noted that “While I have become less and less of a life planner as I’ve gotten older under the headline of ‘man plans, God laughs,’ I am a huge believer in being intentional about everything. And that pretty much sums up Matt’s book: If you don’t have a map, you can’t get where you’re going.

(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 going to be an interesting week.  I expect in a couple days, a group of friends and former Return Path colleagues and I are going to officially start a new company once initial funding closes.  I will write about that down the road, but first, this message brought to you by COVID-19.)

I just returned from spending an intense two weeks in Denver.  On March 15, my long-time friend and Board member Brad Feld called me with an interesting idea.  His friend, Colorado Governor Jared Polis (who I’d met a briefly couple times over the years), had an idea of starting and rapidly scaling up a task force in the state government and wanted to tap a private sector entrepreneur to lead the effort.  After some back and forth over 36 hours, and strong encouragement from Mariquita to go help despite the pending lockdown at home in New York, I decided to jump on a plane and go do it. Here’s the description of the group, called the Innovation Response Team (IRT) that I wrote up on LinkedIn:

Governor Jared Polis established the state of Colorado’s COVID-19 Innovation Response Team (IRT), and I was its initial leader to get it off the ground. The team is responsible for pulling together rapid-response creative programs as part of the state’s response to the pandemic that require entrepreneurial, out-of-the-box thinking and deep connections to the private sector (as well as cross-agency within various levels of government), integrated with the state’s Emergency Operations Center. Along with two key deputies from state government, I was responsible for starting the group, both the public sector and private sector sides; recruiting the state team, a leader for the private sector side, and a long-term replacement for myself; and leading the development of the group’s structure, workstreams, and initial plans along with the rest of the team. In the first two weeks, the team grew from 0 to over 200 people (including an army of private sector volunteers) and started to make a significant impact on the state’s response to the crisis.

At Brad’s suggestion out of the gate, I took daily notes as the project unfolded.  I thought the most interesting way to present the experience here on OnlyOnce (because you *definitely* Only lead a COVID-19 state emergency task force Once) would be to share the daily chronicle, a few days at a time, along with a couple photos I took along the way.  So I’ll do that here, then at the end, I’ll do a wrap-up post that compares the work to running a private sector company.  Because the pace of news around COVID-19 is moving so fast, I’ll post a few days’ worth of daily notes at a time.

Sunday, March 15 – Day -1

• Brad text/call to ask me if I’m interested in doing this
• Lukewarm – not excited about leaving home for 2-4 weeks
• Mariquita encourages me to do it – “when else are you going to get an opportunity to have an impact like this?”
• Jared (Governor) called (spoke a mile a minute), outlined his vision and a couple potential workstreams and discussion ends with “talk tomorrow”
• Can’t sleep – started a Google doc in bed with notes on the first workstreams

Monday, March 16, Day 0

• More back and forth with Jared and his team – Lisa (Chief of Staff) and Stan (supervising cabinet member)
• Officially invited to come at 3 pm
• Kids bummed but supportive
• By 6 pm, packed, cleaned up odds and ends at home and was in a car to Kennedy
• 8 pm flight and airport both still ⅔ full 
• Feeling full of purpose
• Worked on more reading and enhanced doc and Day 1 goals
• Texted Brad:  “Thank you. Wish me luck. I don’t know what the fuck I’m doing. Fortunately I never have and that’s usually been ok.”  Brad LOL.
• Notified parents…a bit shocked
• Good to see and surprise Khalid, the driver we used for years at Return Path
• Crashed in extended stay hotel

Stay tuned for more tomorrow! Apologies if any of these notes or posts aren’t quite right…anyone who was there doing the work with me, please send me any corrections you’d like me to post!

Book Short:  Alignment Well Defined, Part II

Getting the Right Things Done:  A Leader’s Guide to Planning and Execution, by Pascal Dennis, is an excellent and extraordinarily practical book to read if you’re trying to create or reengineer your company’s planning, goal setting, and accountability processes. It’s very similar to the framework that we have generally adapted our planning and goals process off of at Return Path for the last few years, Patrick Lencioni’s The Advantage (book, post/Part I of this series).  My guess is that we will borrow from this and adapt our process even further for 2014.

The book’s history is in Toyota’s Lean Manufacturing system, and given the Lean meme floating around the land of tech startups these days, my guess is that its concepts will resonate with most of the readers of this blog.  The book’s language — True North and Mother Strategies and A3s and Baby A3s — is a little funky, but the principles of simplicity, having a clear target, building a few major initiatives to drive to the target, linking all the plans, and measuring progress are universal.  The “Plan-Do-Check-Adjust” cycle is smart and one of those things that is, to quote an old friend of mine, “common sense that turns out is not so common.”

One interesting thing that the book touches on a bit is the connection between planning/goals and performance management/reviews.  This is something we’ve done fairly well but somewhat piecemeal over the years that we’re increasingly trying to link together more formally.

All in, this is a good read.  It’s not a great fable like Lencioni’s books or Goldratt’s classic The Goal (reminiscent since its example is a manufacturing company).  But it’s approachable, and it comes with a slew of sample processes and reports that make the theory come to life.  If you’re in plan-to-plan mode, I’d recommend Getting the Right Things Done as well as The Advantage.

Taking Stock

Every year around this time, I take a few minutes to reflect on how the business is doing, on my goals and development plans, and on what I want to accomplish in the coming year.  Although most of that work is focused on how to move the business forward, I also make sure to take stock of my own career trajectory.  I always ask myself three questions when I do this:

1. Am I having fun at work?
2. Am I learning and growing as a professional?
3. Is my work financially rewarding enough, either in the short term or in the long term?

Of course, I always shoot for 3 YES responses.  Then I know my career is on track.  But as long as I get 2 YESses, then I feel like I’m in good shape, and I know which one to work on in the coming year.  I’m not sure I’ve ever had a situation in the dozen years of running Return Path where I’ve had 0 or 1 YESses.  If I did, I’d probably spend more time thinking about whether I was still in the right job for me.

I think these three questions can work for anyone, not just a CEO.  Hopefully everyone takes the time to take stock like this at least once a year.  It’s healthy for everyone’s career development.

Challenging Authority

My dad told me a joke once about a kid who as a teenager thought his father was the dumbest person he’d ever met. But then, as the punchline goes, “By the time I’d graduated college, it was amazing how much the old man had learned.”

The older we get as humans, the more we realize how little we know — and how fallible we are. One of our 13 core values at Return Path gets right to the heart of this one:

We challenge complacency, mediocrity, and decisions that don’t make sense

I will note up front that this particular value statement is probably not as widely practiced as most of the others I’m writing about in this series of posts, but it’s as important as any of the others.

Very few things make me happier at work than when an employee challenges me or another leader — and quite frankly, the more junior and less well I know the employee, the better. No matter what the role, we hire smart, ambitious, and intellectually curious people to work at Return Path. Why let all that raw brainpower go to waste?  We thrive as a company in part because we are all trying to do a better job, and because we work with our eyes open to the things happening around us.

I have no doubt that some real percentage of the decisions that I or other leaders of the company make don’t make sense, either in full or in part. And I’m sure that from time to time we become complacent with things that are running smoothly or quietly, even if they’re not optimal or even moderately destructive.  That’s why I’m particularly grateful when someone calls me out on something. We have made great strides in and changes to the business over the years because someone on the team has challenged something. We’ve terminated employees who were poisonous to the organization, we’ve reversed course on strategic plans, we’ve even sold a business unit.

One of the things we do well is blend this value with one I wrote about a few weeks ago about being kind and respectful to each other.  The two play together very nicely in our culture.  People are generally constructive when they have feedback to give or are challenging authority, and people who receive feedback or challenges assume positive intent and nothing personal.  We specifically train people around these delicate balances both via the Action/Design framework and a specific course we teach called Giving and Receiving Feedback.

It takes courage to challenge authority. But then again, nothing great is ever accomplished in life without courage (and enthusiasm, so the old adage goes).

Fred beat me to it. I wasn’t at a computer to post this yesterday on the actual 4th of July, so today will have to do. I’ve read lots of books on the American revolution and the founding fathers over the years. It’s absolutely my favorite historical period, probably because it appeals to the entrepreneur in me. Think about what our founding fathers accomplished:

– Articulated a compelling vision for a better future with home democratic rule and capitalist principles. Life, liberty, and the pursuit of happiness is really the ultimate tag line when you think about it.

– Raised strategic debt financing from, and built critical strategic alliances with France, the Netherlands, and Spain.

– Assembled a team of A players to lead the effort in Washington, Adams, Jefferson, Franklin, Hamilton, and numerous others who haven’t been afforded the same level of historical stature.

– Built early prototypes to prove the model of democratic home rule in the form of most of the 13 colonial assemblies, the Committees of Correspondence, and the Articles of Confederation.

– Relentlessly executed their plans until they were successful, changing tactics several times over the years of 1774-1783 but never wavering from their commitment to the ultimate vision.

– Followed through on their commitments by establishing a new nation along the principles to which they publicly committed early on, and taking it to the next level with the Constitution and our current form of government in 1789.

And let’s not forget, these guys accomplished all of this at a time when it took several days to get a letter from Virginia to Boston on horseback and six weeks to get a message across the Atlantic on a sailboat. Can you imagine what Washington would have been able to accomplish if he could have IMd with Adams in Paris?

So happy 4th to all, with a big thanks to this country’s founding fathers for pulling off the greatest spin-off of all time.

Promiscuity

I figure the title will entice someone new to read this (although he or she might be sorely disappointed with the actual content).  Fred’s posting today about VCs’ conflicts of interest, besides giving me fodder for my weekly counter-cliche posting, brings up another interesting point, one about entrepreneurs and their levels of confidentiality or secrecy about their business plans.

I heard a quote once from Vinod Khosla of Kleiner Perkins that has stayed with me for years:  that “to be successful in the new economy you must be open to the point of promiscuity.”  I think Khosla is right.  As Fred says, VCs are notorious for meeting lots of companies before making an investment, and as an entrepreneur on the other side of the table, it’s impossible to completely protect your ideas and thoughts if you want to attract outside capital.  You just have to trust that the VCs are going to be as honest as possible in how they use the information you share with them.  Same goes for potential partnerships and even M&A as well.  You simply can’t have productive conversations on those topics without opening the proverbial kimono at least a little bit.

But being promiscuous with the state secrets of your business carries certain risks as well.  If the partnership or M&A conversation goes awry, you could easily find yourself with a competitor that knows part of your game plan.  We’ve had this happen at least once at Return Path, and to this day, it still irritates the heck out of us.  But we still think we made the right decision at the time to share that information — and now at least we know that our new competitor isn’t creative enough to come up with his own ideas!

On a completely side note, anyone who’s not using desktop search like Google or the Lookout plugin for Outlook is missing out.  I couldn’t remember the exact quote from Vinod Khosla, but I remembered that it was emailed to me years ago by my colleague Mary Lynn McGrath.  It took Lookout 0.06 seconds to find the exact email from September of 2000 using keywords McGrath and Vinod.  Amazing (and thanks again, Mary Lynn!).

The Value of Paying Down Technical Debt

Our Engineering team has a great term called Technical Debt, which is the accumulation of coding shortcuts and operational inefficiencies over the years in the name of getting product out the door faster that weighs on the company’s code base like debt weighs on a balance sheet.  Like debt, it’s there, you can live with it, but it is a drag on the health of the technology organization and has hard servicing costs.  It’s never fun to pay down technical debt, which takes time away from developing new products and new features and is not really appreciated by anyone outside the engineering organization.

That last point is a mistake, and I can’t encourage CEOs or any leaders within a business strongly enough to view it the opposite way.  Debt may not be fun to pay off, but boy do you feel better after it’s done.  I attended an Engineering all-hands recently where one team presented its work for the past quarter.  For one of our more debt-laden features, this team quietly worked away at code revisions for a few months and drove down operational alerts by over 50% — and more important, drove down application support costs by almost 90%, and all this at a time when usage probably doubled.  Wow. 

I’m not sure how you can successfully scale a company rapidly without inefficiencies in technology.  But on the other side of this particular project, I’m not sure how you can afford NOT to work those ineffiencies out of your system as you grow.  Just as most Americans (political affiliation aside) are wringing their hands over the size and growth of our national debt now because they’re worried about the impact on future generations, engineering organizations of high growth companies need to pay attention to their technical debt and keep it in check relative to the size of their business and code base.

And for CEOs, celebrate the payment of technical debt as if Congress did the unthinkable and put our country back on a sustainable fiscal path, one way or another!

As a long Post Script to this, I asked our CTO Andy and VP Engineering David what they thought of this post before I put it up.  David’s answer was very thoughtful and worth reprinting in full:

 I’d like to share a couple of additional insight as to how Andy and I manage Tech Debt in the org: we insist that it be intentional. What do I mean by “intentional”

•  There is evidence that we should pay it
• There is a pay off at the end

 What are examples of “evidence?”

•  Capacity plans show that we’ll run out of capacity for increased users/usage of a system in a quarter or two
• Performance/stability trends are steadily (or rapidly) moving in the wrong direction
• Alerts/warnings coming off of systems are steadily or rapidly increasing

 What are examples of “pay off?”

•  Increased system capacity
• Improved performance/stability
• Decreased support due to a reduction in alerts/warnings

 We ask the engineers to apply “engineering rigor” to show evidence and pay-offs (i.e. measure, analyze, forecast).

 I bring this up because some engineers like to include “refactoring code” under the umbrella of Tech Debt solely because they don’t like the way the code is written even though there is no evidence that it’s running out of capacity, performance/stability is moving in the wrong direction, etc. This is a “job satisfaction” issue for some engineers. So, it’s important for morale reasons, and the Engineering Directors allocate _some_ time for engineers to do this type of refactoring.  But, it’s also important to help the engineer distinguish between “real” Tech Debt and refactoring for job satisfaction.

Last week, I wrote about the concept of the Operating Philosophy, and how it fits with a company’s Operating Framework and Operating System and defines the essence of who you are as a company…what form of company you are.

While we had a loose Operating Philosophy at Return Path, we never really crisply articulated it, and that caused some hand-wringing at various points over the years, as different people interpreted our “People First” mantra in different ways. So this time around at Bolster, we’re trying to be more intentional about this up front. We have labeled our company a “Mostly Self Managed Organization” or MSMO (pronounced Miz-Moh). We made those up.

Our Operating Philosophy – we are a Mostly Self-Managed Organization, or MSMO (pronounced Miz-Mo, a term we just made up). The MSMO is the product of years of work, research, practical learning, and thinking on our part.  Self-Management has been important to me my whole career as a manager and leader.  Over the last 15 years, the team and I have studied various forms of self-management with interviews and onsite meetings at Netflix, Gore, Nucor, Morningstar, and Zappos.  While we implemented some aspects of it at Return Path, we are trying to take the implementation a step further here at Bolster from the beginning.

Of all those companies, what we’re doing is probably closest to the Operating Philosophy of W.L. Gore & Associates, which you can find written out online without a name but with the description that “individuals don’t need close supervision; what they need is mentoring and support.” The embodiments of the Operating Philosophy at Gore may be different from those we create at Bolster, but the essence of the philosophies is pretty similar.

Why a MSMO?  We employ smart people, and smart people crave autonomy, purpose, and mastery (according to Daniel Pink) and do their best work when they have those things in alignment.  

So, how do we define self-management at Bolster?  We aren’t going to be a DAO.  I don’t think that model works for a for-profit multifaceted corporation – complete Self-Management is too chaotic.  Leadership and mentorship matter and make a difference in guiding strategy, critical decisions, and careers. Holocracies or other unnamed structures like that of Morningstar are ok, but they are so rigidly ideological that they require an immense amount of work-around, or scaffolding, to be practical.

But we aren’t a traditional fixed top-down hierarchy, either.  We are going to run the business in a way that lets people co-create their work and be responsible for driving their own feedback and development with a support structure.  That’s the ideology we have. Letting talented people loose to do their best work is critical; but leadership, judgment, and experience matter, too. If not, why bother having a CEO, or a VP of anything? Why not just pay everyone the same thing and hope they can all figure out the complexities of the business together?

We believe the MSMO is the best operating philosophy to allow high performers to do their best work. 

At Bolster, we are leaning into things like social contracts, peer feedback, career mentorship, individuals translating our Operating Framework into priorities and work, flexible work streams and team leadership, instead of fixed permanent hierarchies, rotating chairs of key company meetings, and market-level-based compensation.  

What we are steering away from are things like traditional titles, micromanaging or overmanaging, traditional performance reviews linked to compensation and complex incentive compensation structures, and fixed organization boundaries and structure.

We’ll see if our MSMO Operating Philosophy works. If not, we’ll iterate on it. That’s the good thing about adherence to an ideology of philosophy as opposed to an ideology of practices. Who knows – maybe the MSMO concept and even its quirky name will catch on!

I am fortunate in my current job to spend a lot of time talking to other founders and CEOs. I mentor and coach them, my company and I help counsel them on executive and board searches, and I spend time with them at conferences and seminars. Even when I am giving them advice, I always take time to learn what they’re doing, what works, and what doesn’t work. I’ve noticed a consistent set of behaviors and practices common among the successful founder operators – the ones who go on to lead their companies through multiple chapters of growth and sometimes never hire the “seasoned operator” to come in and take over. 

#1 – They are students of the game. It’s easy to get mired in the day to day details of building a business from scratch. The best founders are the ones who take time to watch, read, and learn. They want to see what other entrepreneurs do and they ask probing questions about what works and doesn’t work. They read blog posts, articles, and books. They listen to podcasts and constantly try to apply learnings to their company. They seek out coaches and mentors. 

#2 – They have positive and regular (and sometimes extreme) personal habits. It’s easy to get sucked into working all the time when you’re building a business from scratch and counting every penny and every minute. However, observing how successful CEOs manage their time shows that either very early mornings or very late nights are pretty common, and not in the way you might think. A 4:30 or 5 am alarm for regular exercise, or drawing a hard line around “no work after 6” means the leader is committed to personal time to stay fresh, and connect with friends and family. Abraham Lincoln is quoted as having said “Give me 6 hours to chop down a tree, and I will spend the first four sharpening the axe.”

#3 – They know how to leverage themselves. It’s easy as a founder to think you’re the only person who can get something done. Delegation is hard, and it often involves investing more time to train someone else how to do something than doing it yourself. The best founders figure out how to squeeze every minute out of the day by remembering that building a startup is a team sport and that building up the team around them is the key to their own productivity. 

#4 – They have great work hygiene. It’s easy to not respond to emails or texts or Slack messages because they’re not the most important thing you have going on. It’s easy to not send a Thank You note after a meeting or take time to connect with a colleague on a human level. The best founders are the ones who know the power of their own words, the power of their own presence, and who find the time to inject that power into others’ lives.

#5 – They have a recurring belief in creative destruction. It’s easy to create a new company because there’s a need in the market to disrupt incumbents. Creative destruction is central to the story of entrepreneurs everywhere. It’s very hard to apply that same creative destruction mentality to your own work. The best founder operators are the ones who are not just capable of tearing down an industry…but are equally capable and enthusiastic about tearing down their own product, their own team, and their own business processes in order to build them back up. MVPs are often too “M” and need to be replaced and upgraded consistently over time.

None of these practices is the path of least resistance—they require extra effort. I’m not sure what the cause and effect is here. A weak founder with bad product market fit and an untrusting attitude towards employees can’t just start waking up early and reading a lot and magically become successful. But on the margin, enough correlation leads me to believe that there’s something in the combination of these practices that leads to the competitive edge, the informed intuition, the vision, and the ability to motivate the people around them that are common in successful founder operators.