Book (Not So) Short:  Raise Your Hand If You’re Sure

I couldn’t get the catchy jingle from the 80’s commercial for Sure deodorant (you remember, the one with the Statue of Liberty at the end of it – thanks, YouTube) out of my head while I was reading the relatively new book, Confidence: How Winning Streaks and Losing Streaks Begin and End.  Written by HBS professor Rosabeth Moss Kantor, Confidence is one of the few business books I’ve read that’s both long and worth reading in full.

The book has scores of examples of both winning and losing streaks, from sports, business, politics, and other walks of life, and it does a great job of breaking down the core elements that go into creating a winning streak or turnaround (Accountability, Collaboration, Innovation).  Kantor also puts a very fine point on the “doom loop” of losing streaks and just how hard it is to turn them around.  The book also has a good crisp definition of why winning streaks end — arrogange, anyone? — and has consistent, but not preachy recipes for avoiding pitfalls and driving success.  All in all, very inspirational, even if many of the roots of success lie in well-documented leadership qualities like those expressed in Jim Collins’ Built to Last and Good to Great.  The book is good enough that Kantor can even be forgiven for lauding Verizon, probably the most consistently awful customer service company I’ve ever dealt with.

But even more of the roots of success and disappointment around streaks are psychological, and these examples really rang true for me as I reflected back on our acquisition of the troubled NetCreations in 2004.  That company was in the midst of a serious slump, a losing streak dating back to 2000, at the peak of the original Internet boom.  Year over year, the company had lost revenues, profits, customers, and key personnel.  Its parent company saw poor results and set it into the doom loop of starving it for resources and alternating between ignoring it and micromanaging it, and when we acquired the business, we found great assets and some fantastic people (many of whom I’m proud to say are still with us today), but a dispirited, blame-oriented, passive culture that was poised to continue wallowing in decline.

I can hardly claim that we’ve turned the business around in full, or that I personally made happen whatever turnaround there has been, but I do think we did a few things right as far as Kantor and Confidence would see it.  Her formula for a turnaround (Espouse the new message, Exemplify it with leadership actions, Establish programs to systematically drive it home throughout the organization) is right in line with our philosophy here at Return Path.

First, we accelerated the separation and autonomy of a fledgeling NetCreations spin-off unit, now our Authentic Response market research group, and let a culture of collaboration and innovation flourish under an exceptionally talented leader, Jeff Mattes.

But that was the easy part (for me anyway), because that part of the business was actually working well, and we just let it do its thing, with more support from HQ.  The turnaround of the core list rental and lead generation business of NetCreations, the original Postmaster Direct, was much tougher and is still a work in progress.  In the last six months, we’ve finally turned the corner, but it hasn’t been easy.  Even though we knew lots of what had to be done early on, actually doing it is much harder than b-school platitudes or even the best-written books make it seem.

The one thing that Kantor probably gives short shrift to, although she does mention it in passing a couple times, is that frequently turnarounds require massive major amounts of purging of personnel (not just management) to take hold.  As one of my former colleagues from Mercer Management Consulting used to say, “sometimes the only way to effect Change Management is to change management.”  Sometimes even very talented people are just bogged down with baggage — the “ghost of quarters past” — and nothing you do or say can break that psychological barrier.

Boy, have we learned that lesson here at Return Path the hard way.  I’m extremely grateful to our team at Return Path, from the old RP people who’ve seen it all happen, to the old NetCreations people who are thriving in the new environment, to the new blood we’ve brought in to help effect the turnaround, for playing such important roles in our own Confidence-building exercises here.  And I’m super Confident that 2007 will be the year that we officially turn the old NetCreations/Postmaster losing streak into a big, multi-year winning streak.

Anyway, I realize this may redefine the “short” in book short, but Confidence is without question a good general management and leadership read.

7 Years On

My last September 11 as a New York City resident. I walked down to the World Trade Center site this morning as I have each of the last six 9/11s and rang The Bell of the Unforgotten, which is the New York City Fire Department’s port-a-memorial that they bring out for the day. As a long-time member of the lower Manhattan community, the day always bring out a lot of reflection for me. Seeing the memorial flood lights on tonight will do the same and bookend the day.

The main thing I was thinking about this morning was why there’s been nothing really built yet on the site. World Trade Center 7 (which is actually adjacent to the main site) went up in a hurry a few years ago (pictured here under construction four years ago), but nothing else.

My general understanding of the situation is that the holdup has not been around clean-up or pre-construction the last several years, but all about legal, political, and insurance issues. And that smacks to me of a leadership problem. I realize there are a lot of parties involved, and a lot at stake, but it’s just embarrassing to America that we haven’t rebuilt the site — and fast. Set an example to the rest of the world that we react swiftly and don’t let the bad guys knock us down…and keep us down.

It feels to me like a President who actually understood leadership would have gotten all the parties in a room together and not let them out until there was agreement on a plan. Don’t just let “the system” play things out laissez faire, but actually play them out in a hurry so the country and city can move forward. It feels like the kind of thing Reagan or Clinton would have done.

As I reflect on this today, the one thing I’m happy about is that no matter who wins the White House, America will be getting a leadership upgrade.

The Gift of Feedback

My colleague Anita Absey always says that “feedback is a gift.”  I’ve written in the past about our extensive 360 review process at Return Path, and also about how I handle my review and bring the Board in on it.  But this past week, I finished delivering all of our senior staff 360 reviews, and I received the write-up and analysis of my own review.  And once again, I have to say, the process is incredibly valuable. 

For the first time in a long time this year, I got a resounding “much improved” on all of my prior year’s development items from my team and from the Board.  This was great to hear.  As usual, this year’s development items are similarly thoughtful and build on the prior ones, in the context of where the business is going.  Since one of my prior year’s items was “be as transparent as possible,” I thought I’d share my development plan for the coming 12-18 months here on my blog.  If you’re reading this and you report to me, you’ll get a longer form debrief at our next offsite.

1. Continue making the organization more of a Hedgehog, lending more focus to our mission and removing distractions wherever possible.

2. Move the organization’s leadership team from “pacesetting” to “authoritative” management styles by focusing more on :

    a. standards of excellence around employee behavior and performance: develop a more clear performance management system, raise the bar on accountability around leadership and management issues, shift management training from tools to values-based coaching

    b. clear communication loops: balance open door policy with manager empowerment by getting the executive in charge to fix issues (instead of fixing them myself) and/or facilitating stronger manager-employee communication

    c. constant translation of vision into execution: foster clearer context and deeper employee engagement by not just communicating vision, but communicating HOW the vision becomes reality at every opportunity

3. Sharpen elbows further around leadership team: identify key attributes of success, weed out underperformers, re-scope other roles, and clarify “partner for success” opportunities as part of core responsibilities. Make each individual’s development needs public in the senior team (I guess this is the first step towards that!)

4. Make the organization more nimble, inspiring a bias for action through shifts in priorities and cross-functional swat teams where required

So there you go.  If you work at Return Path, please feel free to hold my feet to the fire in the coming months on these points!

This is another big week for us at Bolster. On the heels of the announcement we made last month about our Series B financing, we are now announcing the launch of a new program called Bolster Prime and a new venture capital fund called Bolster Ventures. These are important steps in Bolster’s evolution and in the fulfillment of our mission, what we call internally our “Big Idea,” which is to empower the innovation economy.  

The roots of Bolster Prime and Bolster Ventures pre-date the founding of Bolster. In our prior lives, the Bolster founders worked together to scale up a business called Return Path and also 

worked as advisors and mentors to numerous early stage founders and startups. One of the things we noted in our very first post, now part of the About Us section of Bolster.com, was:

After exiting Return Path [the company where our founding team worked for many years], we wanted to do for others what we did for each other as a seasoned executive team. We wanted to know: “How could we help other CEOs, executives and boards bolster themselves to go the distance and scale with their organizations?”

While the founding team was exploring potential business opportunities that allowed us to make a bigger impact on the world, Silicon Valley Bank and High Alpha Innovation were together envisioning a platform to help VC-backed portfolio companies more effectively navigate the complex world of executive talent needs. When our three groups came together, we realized we shared a vision to build a company that puts people first in all aspects to drive high-growth businesses.

I’ve never written before about those other “potential business opportunities” that our team was exploring along with our prior investment syndicate, Fred Wilson from Union Square Ventures, Greg Sands from Costanoa Ventures, and Brad Feld from Foundry. The one our team was particularly excited about was a concept we were calling at the time “Venture Acceleration Partners.” The key points in the pitch deck we created were:

• There is a gap in the market of investors adding “management” value to portfolio companies between Accelerators/Incubators/Studios at the low end and Private Equity firms and very large VCs at the high end. What about the middle?
  
• “The middle” consists of venture-backed companies that are neither early stage nor mature. They are typically founder-led, often by a first-time CEO with new or incomplete management teams who need a lot of mentorship/development, and with a diversified cap table of firms that don’t own operating or consulting practices to help guide the scaling process.
  
• These companies tend to have consistent and stage-unique challenges around scaling execution across every aspect of the business.
  
• By creating an advisory firm made up of seasoned operators, we can quickly identify the risk areas and provide mentoring, guidance and execution to management teams for defined periods of time to keep them on the right track and increase their companies’ performance.
  
• We want to create a firm that has enough skin in the game to have long-term relationships with management teams…and that doesn’t charge (much) for services because incentives are aligned as a co-investor.

Our original deck envisioned a firm that was sort of a hybrid of a “McKinsey for startups” and a venture investor. When I shared that pitch deck (and two other ones I’ll save for another day), with my long-time friend Scott Dorsey from High Alpha, he responded by sharing with me a related pitch deck he was working on with corporate partner Silicon Valley Bank out of the High Alpha Studio for a talent marketplace. We immediately looked at each other and said “we should put all of these ideas together with this founding team, High Alpha and SVB, and the Return Path investors, and change the way startups connect with talent.” That’s what we did, and we almost immediately started building the first part of the Bolster business, which was the talent marketplace.

About six months into our journey building Bolster, I was talking to Brad and reminded him that I was interested in bringing the Venture Acceleration idea to life now that we had a vibrant talent marketplace up and running at Bolster. 

Standing up a new program of this magnitude with limited resources at the same time as building a new venture capital firm from the ground up, on top of a still pretty brand new startup – that felt like a tall order, even for a large and senior founding team like ours. We needed another senior leader to join our team. 

Brad’s visceral response in this conversation was a very clear, “you should hire Jenny.” Enter Jenny Lawton. Jenny is someone I’d known peripherally for many years as a mutual friend and colleague of Brad, but we weren’t particularly close. We agreed to meet for breakfast at a diner halfway between our houses at a time in the pandemic when there wasn’t a whole lot of in-person meetings going on. 

As Jenny’s written about this week, it was the right call at the right time – we had a full meeting of the minds about the role mentorship plays in supporting entrepreneurs, the unmet needs of entrepreneurs even with all the support out there from accelerators and investors, and the desire that both of us had here in the back half of our careers to, as Steve Jobs would say, “make a dent in the universe.” Jenny’s experience as a multiple-time senior executive and startup advisor (including four years as the COO of Techstars) was a perfect match for us. She joined our team pretty quickly, first fractionally (the Bolster way, right?), then full-time in the middle of 2021. 

And the rest, as they say, is history. Working as part of the Bolster leadership team this past year, Jenny has spearheaded the creation of Bolster Prime, from selling and mentoring the first few clients personally, to designing the curriculum and programmatic learning, to figuring out the right positioning and pricing to developing the recruiting strategy for the program. We’ve worked together and along with the rest of the team at Bolster to bring in an amazingly talented group of experienced former and current CEOs and other senior operators as our first group of mentors.  Any entrepreneur would be lucky to have one of these mentors in their corner. We’ve now raised a venture capital fund as first-time fund managers from our own investors and our program’s mentors, all of whom believe in the power of Bolster as the next generation platform to help empower the innovation economy. 

Most good ideas swim in a sea of comparables. There are now a handful of other firms out there that combine advice for entrepreneurs with capital. But we believe our model, with thousands of Bolster Member CXOs already on board, is unique. Bolster Prime and Bolster Ventures, powered by Bolster’s on-demand talent marketplace, is here to help early stage founders reimagine the way they scale up their leadership teams, their boards, and themselves. We are changing the way the startup game is played. Come take a look and see what’s in it for you.

As I finished up my work on the Second Edition of Startup CEO:  A Field Guide to Scaling Up Your Business and started working on a new startup, my colleagues and I started envisioning a new book as a sequel or companion to Startup CEO that is going to be published on June 9 with our same publisher, Wiley & Sons.  The book is called Startup CXO:  A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Simply put, the first book left me with the nagging feeling that it wasn’t enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to grow a company?  If you’re leading HR, or Finance, or Marketing, or any key function inside a startup, what resources are available to you? What should you be thinking about?  What does ‘great’ look like?  What challenges lurk around the corner as you scale your function that you might not be focused on today?  If you’re a CEO who has never managed all these functions before, what should you be looking for when you hire and manage all these people?  If you’re an aspiring executive, from entry-level to manager to director, what do you need to think about as you grow your career and develop your skills?

Startup CXO is a “book of books,” with one section for each major function inside a company.  Each section is be composed of 15-20 discrete short chapters outlining the key “playbooks” for each functional role in the company – Chief People Officer, Chief Financial Officer, Chief Marketing Officer, Chief Revenue Officer, etc., hence the title Startup CXO – which is a generally accepted label in the startup ecosystem for “Chief ____ Officer.”

Here are the front and back covers of the book, with some great endorsements we’re so proud of on the back.

This is an important topic to write about at this particular time because America’s “startup revolution” continues to gather steam.  There are only increasing numbers of venture capital investors, seed funds, and accelerators supporting increasing numbers of entrepreneurial ventures.  While there are a number of books in the marketplace about CEOs and leadership, and some about individual functional disciplines (lots of books about the topic of Sales, the topic of Product Development), there are very few books that are practical how-to guides for any individual function, and NONE that wrap all these functions into a compendium that can be used by a whole startup executive team.  Very simply, each section of this book serves as a how-to guide for a given executive, and taken together, the book will be a good how-to guide for startup executive teams in general.

Startup CXO has my name on it as principal author, and I’m writing parts of it, but I can’t even pretend to write it on my own, so the book has a large number of contributors who have the experience, credibility, and expertise to share something of value with others in their specific functional disciplines — most of my Bolster co-founders are writing sections, and the others are being written by former Return Path executive colleagues — Jack Sinclair, Cathy Hawley, Ken Takahashi, Anita Absey, George Bilbrey, Dennis Dayman, Nick Badgett, Shawn Nussbaum, and Holly Enneking.

Startup CXO is also pretty closely related to Bolster’s business, since we are in the business of helping assess and place on-demand CXO talent, and as such, the final section of the book has a series of chapters written by Bolster members who are career Fractional Executives about their experience as a Fractional CXO.

The book is available for pre-order now at Amazon and Barnes & Noble.

Oh, and stay tuned for a third book in the series (kind of) due out late this year. More on that over the summer as the project takes shape!

(This post, written by my co-founder Cathy Hawley, also appeared on Bolster.com)

The gig economy is a labor market where short-term or freelance roles are more prevalent than permanent positions. It’s generally characterized by having independent contractors rather than full-time positions, but in some locations and for some types of roles, gig workers may be part-time or fixed-term employees.

The gig economy that started with roles like artists, drivers and web designers is quickly expanding to include executive-level roles. There are  a few trends in today’s workplace that are driving this expansion. Startups and scaleups have more flexible, remote-friendly work environments and are looking for creative, less expensive ways of accelerating growth. Executives have shorter average job tenure and are more often displaced or between roles, and they are also interested in the flexibility that gig work can give them.

In a study conducted by MavenLink/Research Now, “The White Collar Gig Economy,” 47% of companies state they are looking to hire contractors to fill management and senior executive roles, including c-suite contractors. At the same time, 63% of full-time executives would switch to become a contractor, given the opportunity. These trends will be accelerated by the current economic downturn and recovery, as some companies have fewer resources, and more executives are displaced.

At the executive level, there are a few different types of roles that could be considered ‘gigs’. The most common two are coaching and project-based consulting.  Coaching or advising, and particularly CEO coaching and advising, has become very prevalent over the last 10 years. The CEO hires a coach who can help them navigate new situations and challenges. Often, CEO coaches stay with a CEO for a number of years, helping guide and support them through the stages of company growth. There are also coaches and advisors for other functional areas to provide similar support for other executives, although more commonly these coaches are hired for specific initiatives. 

Then there  is project-based consulting, where executive-level talent is hired to run a specific project such as reviewing a company’s packaging and pricing, performing due diligence on an acquisition, creating a Diversity, Equity and Inclusion strategy, or creating an investor deck for a fundraising event. This type of consulting isn’t new, and it’s similar to what large consulting firms offer. It seems to be more prevalent now for very senior roles than it ever has been in the past.

But the gig economy for executives now reaches well beyond coaches and consultants.  There are also executives who are hired into interim leadership roles while a company searches for a permanent placement. Some roles take a long time to find the right person, but there’s an urgent need for someone to take on the leadership mantle in the interim. If the interim executive is a good fit, and is open to it, it’s not uncommon for this individual to be considered for the permanent position.  “Try before you buy” works both ways — it can be good for the company and good for the executive, too.

An up-and-coming type of executive gig role is the fractional role. We are seeing this more and more in the last couple of years.  Fractional executives can either be consultants or employees, since the expectation is a long-term relationship, on a part-time basis. For example, 3 days or a certain number of hours per week. The fractional executive is responsible for all functional areas as a full-time executive in that same role. The company may be too small to need (or afford) their level of expertise on a full time basis, but needs more than just an advisor or project consultant. The fractional executive generally remains with a company until the company needs a full-time leader for that function, in which case either the fractional executive goes full-time, or the company hires someone new.  Fractional executives may support more than one client at a time, and may also come with a team of more junior functional experts who can support them to take on more work.

Finally, for our purposes at Bolster, joining a company’s board of directors could be considered taking a ‘gig’ role since it’s not a full-time executive role.  Startups and scaleups need independent directors, and their needs change based on their size, stage and strategy. We see a growing trend of companies contracting with directors for 1 -2 years rather than lifetime service. 

There’s a real opportunity right now for companies to capitalize on the expertise of this talent pool without having to hire them for long-term full time roles, and for executives who want to contribute their skills and expertise without the commitment of a 80-hour work week. Bolster is helping bring these two audiences together in a marketplace that matches on-demand executives with companies who need their services the most. Bolster also provides services for members so they can focus on their consulting rather than their business, and for companies to evaluate their executive teams and boards.

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

Harry Potter was lucky.  He had, in Albus Dumbledore, the ultimate wise elder, in his corner.  Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys.

All of us would benefit from having an Albus Dumbledore in our lives.  But most of us don’t — and most of the people we’d call on to be that wise elder in our corner aren’t capable of the full range of advice and counsel that Dumbledore is. 

Why work with a Coach or a Mentor?  I’ll start this post with a quick argument in favor of CEO Coaches and Mentors (sometimes called Advisors).  Even as a 20-something first-time CEO years ago, I was deeply skeptical of the value of a Coach, but that was in 1999 or 2000 when coaches weren’t so commonplace.  Now that their value seems much more obvious, and there are so many amazing Mentors and Coaches available, I’m surprised by how many CEOs I speak to still seem skeptical about their value.  Just think — the world’s greatest athletes, the ones who get paid zillions of dollars because they are the best in the world at something, use MULTIPLE coaches DAILY to perfect their craft and keep them focused.  Why should Rafael Nadal or Serena Williams have a trainer and a coach, but not you?

I’ve benefited over the years from the advice of more people than I can ever count or thank.  But when it comes to being a CEO, I have leveraged the counsel of a CEO Coach or Mentor principally in three different areas:

1. Functional topics on the craft of being a CEO from the lofty “how to run a board meeting” to the nitty gritty details of “how to do a layoff”
2. Developmental/behavioral topics like “how I show up as a leader in the organization,” or “how to be a better listener”
3. Team Effectiveness topics like “how do I get the most out of my leadership team,” or “why doesn’t Person X trust Person Y and how does that impact team performance?”

In some unusual circumstances, you can find a person who does all three of these things for you and can scale as you and your company grow.  But for the most part, getting all three of these things requires engaging two different people, and maybe even more mentors.  

What’s the difference between a CEO Mentor and a CEO Coach?  Counsel on Item 1 above — what I would call CEO Mentorship — almost certainly requires someone to have been a CEO — preferably multiple times, or for a long period of time, or through multiple stages of company growth, or two or three of those qualifiers.  This is the kind of person who can literally teach you how to do CEO things.  These people are super busy, they won’t have open ended amounts of time for you, but you should expect sage wisdom and answers when you need them.  And you can have more than one of them at a time, or change them out as your company evolves and your needs change.

Counsel on items 2 and 3 — what I would call CEO Coaching — frequently come together in a professional who is and has been for a while, a coach.  The person might have had a significant career in business before becoming a coach but wasn’t necessarily a CEO.  The person probably has some kind of academic grounding, like a Master’s degree in Organizational Development or Industrial Psychology, or a Certificate in Coaching.  This is the kind of person who can do things for you and your team like facilitate meetings, run assessments like Myers-Briggs or DISC, and coach other leaders on your team.  This person is dedicated to helping you be the best leader, professional, and CEO that you can be and must be both empathetic and comfortable pushing you hard.  

Sometimes you get mentorship and coaching in the same person, but almost only with CEO Coaches who are also CEO Mentors by my definition above.

Five signs you need a CEO Mentor and/or Coach:

• You are playing ‘whack-a-mole’ — running from crisis to crisis in your organization and are not able to make time to think, be current with email, or make time for important things like hiring senior executives
• Your board is getting frustrated with you, your team and/or the lack of progress in the business
• The company isn’t scaling as fast as it should
• Your leadership team is not a cohesive team and you are in the middle of all decisions
• The company has high employee turnover and/or poor reviews on Glassdoor 

Do yourself and your company a favor and invest in a CEO Coach and Mentor(s). It’s an investment in accelerating your own and your company’s success. In later posts, I’ll talk about how to hire and best leverage both Coaches and Mentors. 

Next post in the series coming:  How to Select a CEO Mentor or CEO Coach

It’s good that my friend Brad Feld‘s new book (co-authored by Dave Jilk, who I’ve also known on and off over the years), is divided into 52 chapters and is designed as a bit of a devotional, to be read one chapter per week.

Each chapter of The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors is, as the authors write in the Introduction, worth “chewing on a while.” The structure of the book is laid out as:

The book contains fifty-two individual chapters (one for each week) and is divided into five major sections (Strategy, Culture, Free Spirits, Leadership, and Tactics). Each chapter begins with a quote from one of Nietzsche’s works, using a public domain translation, followed by our own adaptation of the quote to 21st-century English. Next is a brief essay applying the quote to entrepreneurship. About two-thirds of the chapters include a narrative by or about an entrepreneur we know (or know of), telling a concrete story from their personal experience as it applies to the quote, the essay, or both.

That structure is perfect for me. I did ok in Philosophy classes, but I wouldn’t say it was my preferred subject. So the fact that Brad and Dave turned every Nietzsche quote into plain English before applying it to entrepreneurship and disruption was a welcome tactic to make the book as accessible as possible.

I wrote one of the essays in the book on creating a Company Operating System, which is in the chapter called “Doing is not Leading.” It’s an honor to be included as a contributor alongside a number of awesome CEOs, including Reid Hoffman, Ingrid Alongi, Daniel Benhammou, Sal Carcia, Ben Casnocha, Ralph Clark, David Cohen, Mat Ellis, Tim Enwall, Nicole Glaros, Will Herman, Mike Kail, Luke Kanies, Walter Knapp, Gary LaFever, Tracy Lawrence, Jenny Lawton, Seth Levine, Bart Lorang, David Mandell, Jason Mendelson, Tim Miller, Matt Munson, Ted Myerson, Bre Pettis, Laura Rich, Jacqueline Ros, and Jud Valeski.

In his Foreword, Reid Hoffman connects the dots perfectly:

Returning to Nietzsche, let’s examine why he in particular is such an apt patron philosopher for entrepreneurs. Nietzsche was rebelling against a stultifying philosophical practice that exalted the past—specifically the ideals and images of former thinkers and former leaders. He wanted to refocus on the now, on what humanity was and what it could become. As part of his rebellion, Nietzsche philosophized with a hammer: he wanted to destroy the old mindsets that locked people into the past, and thus better equip them to embrace the possibility of the new. Nietzsche’s desire to shift mindsets is also why he emphasized new styles of argument. Whereas most philosophers would typically open an argument in a classical form or by reviewing a historical great, Nietzsche would lead with an arresting aphorism or a completely new mythological narrative. He was, above all else, a disruptor of pieties and convention, always in search of new and original ways to be contrarian and right, never satisfied with the status quo. This is exactly the kind of mindset entrepreneurs should adopt. This is why a daily practice of philosophy can be the way that an entrepreneur moves from good to great. And, why a daily practice of Nietzsche is a great practice of philosophy for entrepreneurs.

What I love about the book is that you can read any given chapter at any time without having to read it front to back, and the combination of Nietzsche and entrepreneur essays makes the topics come to list. Pick one — they are organized into five sections, Strategy, Culture, Free Spirits, Leadership, and Tactics — and you’re sure to get both something chewy (e.g, thoughtful) and delicious (e.g., practical).

(This is the sixth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, 4, and 5.)

As these posts have been running, a few people have asked me to quickly compare this experience to the experience of being a Startup CEO.  And that’s an interesting way to think about it. In a lot of ways, the couple of weeks of getting the IRT up and running felt like starting up a new business, only a lot more intense.  Following the outline of sections in Startup CEO:  a field guide to scaling up your business…

Part One: Storytelling.  The whole timeframe was super compressed.  It took us 2 days to be able to spend 4 hours writing our initial pitch deck defining scope, structure, and staffing request – and that was while we were working hard on our first two workstreams.  In a startup environment, that process would have taken much longer, involved more customer discovery and product/market fit research and spending 100% of our time on that. But then we got our “approval and funding” in about 45 minutes – that would have taken weeks and involved dozens of pitch meetings.  In terms of creating the organization’s Mission, Vision, and Values, we didn’t even bother, although I think it helped that the three of us were generally on the same page with how to work and that urgency was the essence of our job. The larger emergency operations team that we were more or less embedded in also had a very clear set of values and operating principles on display…although we didn’t actually go read them, I think they were in sync with our view of our team’s mission and principles.  In terms of “bringing our story to life,” that was wholly unnecessary!

Part Two: Building The Company’s Human Capital.  Like a startup, getting it right with the first handful of employees means everything.  In this case, the first two deputies on the team, handpicked by the Governor’s staff, were awesome and critical.  Bringing someone in from the private sector to run a public sector team only works when the rest of the team is incredibly knowledgeable about how the machinery of state government works.  And in the end, I think Sarah will be a better leader for the team than I was because she had a combination of private and public sector experience (and within her public sector experience, she had a lot of emergency response experience).  In general, the recruiting process was soooo different than private sector and public sector normally are. The first two team members handpicked the best people they knew in other relevant parts of the government. People were brought onto the team after one short phone call.  Other state departments heads loaned their people willingly. No such thing as a comp negotiation or a reference check. There were a bunch of other things under the “Human Capital” heading that are interesting notes/comparables as well. First, feedback in a compressed-timeframe emergency is something that you absolutely can’t skip – and you can’t wait for a formal process either.  Our team was pretty good about giving feedback at least daily in a semi-structured way as well as in the moment. We didn’t really have time to get into things like career pathing and compensation and firing. We did, after about 6 days at the suggestion of Kacey, our Chief of Staff, move the team to almost entirely remote (other than leadership and occasional critical meetings). This worked surprisingly well for a workforce probably unaccustomed to remote work.  The rest of the world is also learning how to do a lot of that now, too.

Part Three: Execution.  This whole experience was 97% execution.  In fact, we had a hard time finding time for things like strategy and planning because there was a crushing amount of work to do (welcome to emergency response), and a small team to do it.  We didn’t have to worry about raising money, budgeting, forecasting, reporting, and some of the other major execution steps in the private sector. We did do a good job of creating goals and milestones for our workstreams, but even that took a couple of weeks, and in retrospect, I wish we’d been able to do some of those sooner.  In terms of how our work got done, we were very conscious of creating daily meeting routines to structure our day and work – but there was no such thing as even a weekly meeting (let alone monthly strategics or quarterly offsites!), only daily meetings, multiple times per day. One thing that was interesting – I talk in the book about being deliberate and consistent with your platforms, especially around communication.  Channel proliferation is a real issue today (much more so than when I wrote the book), but we had an interesting mismatch at the beginning. The public sector team was used to email, text, and Google hangouts for comms. Nothing else. The private sector team used those things but was a lot more comfortable with Trello, Zoom, and Slack. Thank goodness both teams used G-Suite and not a mix of that and LiveOffice. But getting everyone on the team to converge on a couple systems is a work in progress and was messy, as evidenced in this great moment where Kacey was holding a laptop up to an actual whiteboard to show one of our private sector teams how she was thinking about something. 

Part Four: Building and Leading a Board of Directors.  This is kind of N/A, although the proxy for it in our case on the IRT was the leadership structure of the Emergency Operations Center and then the Governor and the part of his cabinet that was keyed into the emergency response.  In this regard, the main differences between the private sector and public sector were speed/formality (no room for formality when you’re meeting daily or at a moment’s notice!), and, interesting, the need for integration. A company reports to its board on how it’s doing.  This team had to use its “board” to make sure it was integrating with other state agencies and initiatives. In this way, the team functioned more like a business unit within a company than an actual company.

Part Five: Managing Yourself So You can Manage Others.  This was obviously critical…and obviously quite difficult.  And within the overall Emergency Operations Center (outside of our team, the real emergency professionals), there were people, including leaders, who were working 7 days/week for multiple weeks on end, and long days, too.  At one point, the EOC leader posted this note on the wall, and he frequently took time in daily briefings to encourage everyone to take a day or two off and take care of themselves physically.  He role-modeled that behavior as well. You can only run a sprint for so long. Once it becomes clear it’s a marathon, well, you know.

Stay tuned for the final post in the series tomorrow…

Post 4 of 4 in the series of Scaling CPO’s- the other posts are, When to Hire your First Chief People Officer, What does Great Look like in a Chief Privacy Officer and Signs your Chief Privacy Officer isn’t Scaling.

You won’t have a ton of time to engage with the Chief People Officer but there are a few ways where I’ve typically spent the most time, or gotten the most value out or my interactions with them. So, you’ll need to capitalize during those few moments when you do get a chance to engage with the Chief People Officer.

I ALWAYS work with the CPO as a direct report.  No matter who my HR leader is, no matter how big my executive team is, no matter how junior that person is compared to the other executives. I will always have that person report directly to me and be part of the senior most operating group in the company.  That sends the signal to everybody in the company that the People function (and quite frankly, diversity, culture, and a whole host of other things) are just as important to me as sales or product. I guess that’s walking the walk, not just talking. If I’m not serious about diversity, about our core values, and about the people in the company, no one else will be either. So, I always have the CPO as a direct report.

A second way to engage with the CPO is to insist on hearing about ALL people issues. First, I am a very “retail-oriented” CEO, and I like to engage with people in the business—at all levels, in all departments, and in all locations.  So I like know what’s going on with people — who is doing particularly well and about to be promoted, who is struggling, who is a flight risk, who is going through some personal issue (good or bad) that we should know about. This isn’t prying into people’s lives, but a real way to engage with people beyond business and a way to show that you care about them as a person. Even more than just me wanting to be in the know, I want others in the company to have a deep level of awareness of our contributors. For example, in our Weekly Sales Forecast meeting at Return Path, because our head of People knew that I wanted to know about all these details on our employees, they insisted that all the other People Business Partners roll those issues up as well. That means everybody in the room was in the know as well.  It’s not just to have a better understanding of people, there’s a business case for knowing what’s going on at a very detailed level and the number of issues we nipped in the bud, the number of opportunities we were able to jump on to help employees over the years because of this retail focus, has been immense.

I also engage with the CPO as an informal coach for myself and with my external coach.  In an earlier post I mentioned that a great Chief People Officer can—and should—call a CEO out when a CEO needs to be called out.  And that also means that great Chief People Officers engage with CEOs deeply about how they are doing, they help CEOs process difficult situations, and help them see things they might not otherwise see.  Being a CEO is a lonely job sometimes, and it’s good to have a People partner to be able to collaborate with on some of the most personal and sensitive issues.

Finally, I engage with the CPO to design and execute Leadership/Management training.  This is an important skill that a great CPO brings to the company and I have found that it is the best way to create a multiplier effect of employee engagement and productivity. The CPO in your organization needs to teach all leaders and managers how to be excellent at those crafts — and how to do them in ways that are consistent with your company’s values.  This is a tall order for one person to put together so I always took a lot of time, in large blocks of hours or days, to either co-create leadership training materials and workshops with my head of People, or to lead sessions at those workshops and engage with the company’s managers and leaders in a very personal way.  That always felt to me like a very high ROI use of time.

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

(Post 1 of 4 in the series of Scaling CPO’s)

In most startups, the HR function starts out as tactical, because you have to get people hired and paid, and while you might have a founder or early-stage employee who can do these things, often these tasks are frequently outsourced to a PEO.  As the company grows, it probably in-sources payroll and benefits, hires a recruiter, and maybe has an HR Manager who handles the function. Depending on the number of roles you see being filled, the degree of specialization, or a host of other factors, an in-house team to handle the tactical aspects of HR makes a lot of sense. But at some point you may need to hire a Chief People Officer.

One sign that it’s time to hire a Chief People Officer is if you feel that you’re the driver of company values, that you’re the one talking about values and viewing the company and interactions with that lens—but you’re the only one that cares about the core values. If your HR function is only focused on the tactical aspects of the role and not on how values drive the company, you’ll need to consider a full-time People Officer because focusing on tactical functions only will not help your company scale.

Another sign is if you are spending too much of your own time training managers and leaders or working on interpersonal dynamics on your leadership team. What’s the right amount of time? I think of these tasks (if you’re a a CEO) as things where you should be more like a consultant rather than the driving force behind them. If you find that a large portion of your day or week is filled with people ops activities, it’s time to think about hiring someone.

A third sign that it might be time to hire a People officer can happen when your board asks you what your talent strategy is with respect to improving diversity, retention, and engagement metrics, while simultaneously decreasing average employee salary, and you don’t have a great answer. While it’s acceptable—occasionally—to not know the strategy at a detailed level for a particular part of your business, if you get asked a question by your board and haven’t the faintest idea on how you can get an answer, that ‘s a good sign that you should consider brining in a full-time Chief People Officer.

A fraction Chief People Officer may be a great option, especially if you have a very competent HR manager or director who has strategic inclinations but not enough experience operating as a strategic executive.  If you have a person who just needs a little more supervision in order to “level up” then a fractional executive could be helpful. Or, if you need someone to play more of a consigliere or team coach role to your executive team but don’t want to engage a coach — and your day-to-day HR leader is getting the job done but too junior to facilitate workshops for the senior team, a fractional executive would work. Finally, if you have a very junior HR function or are insourcing it for the first time and need help setting up the whole function from scratch at an advanced size relative to other functions, a fractional executive would be helpful.

As a startup it’s easy to focus on the day-to-day operational details of the People Ops team because those things—payroll, benefits, hiring, onboarding—are tangible and have metrics associated with them. But those things won’t help you scale. If you want to scale your company, if you want to go from $2 million in revenues to $50 million you’ll need to have a person in your organization who is passionate about the values and passionate about helping individual contributors and leaders connect their work to the values. A Chief People Officer will be able to step in and be a leader to the leadership team; after all, companies are built into greatness by people, so this key position is pivotal to the company. 

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