I’ve always been a big believer in the Operating Framework and the Operating System as two of the management underpinnings behind every well run company.

The Operating Framework is the company’s Mission, Vision, Values, Strategic Objectives, and Key Metrics. Companies have all sorts of different labels for this, from Balanced Scorecard to Salesforce’s V2MOM to Patrick Lencioni’s 6 Questions. It’s what you have to define up front, refresh annually, and tweak quarterly so that people in the company are aligned and know where you’re going.

The Operating System, as I wrote extensively about in Startup CEO, is the collection of practices, meetings, mailing lists, routines/rhythms, and behaviors that your company and team use and depend on to run the business on a day to day basis. It’s what you have to put in place and tweak as needed so work gets done efficiently – the thing that turns the sprint of a raw startup into the marathon of a scaling business.

But there’s a third leg to the stool of company management underpinnings that’s often overlooked and underappreciated – the company’s Operating Philosophy. The Operating Philosophy is the intellectual underpinning of how you want to run and lead the business. It’s related to, but different from, your company’s values. Think of it as the essence of how you want to work and shape the work of others…what defines your form of company.

You can run a company perfectly well without a clear Operating Philosophy, especially with a tight Operating Framework and Operating System in place. But my guess is that you have one, you just haven’t articulated it yet, and you might benefit from doing so. At least that was our experience where we had an undefined but real one at Return Path and have now tried to define one front and center at Bolster.

A useful way to think about these three legs of the stool is the analogy of government (bear with me on this and pretend like our government in the US isn’t quite as dysfunctional as it is at the moment). Our Operating Framework is the Constitution – it lays out the broad contours of what our government does. Our mission, vision, and values. Our Operating System is the collection of policies, practices, and programs that run the country, from the timing and cadence of elections, to the ways the three branches of government enact and execute policy, to the ways state and local governments fit in. Our Operating Philosophy is the Declaration of Independence. It’s our essence. It is what separates our form of government from other forms of government. We are a Representative Democracy, a Constitutional Federal Republic. We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness. That to secure these rights, Governments are instituted among Men, deriving their just powers from the consent of the governed.

Some examples? Zappos is a Holocracy – defined as a system of corporate governance whereby members of a team or business form distinct, autonomous, yet symbiotic, teams to accomplish tasks and company goals. The concept of a corporate hierarchy is discarded in favor of a flat organizational structure where all workers have an equal voice while simultaneously answering to the direction of shared authority. Patagonia (and lots of other companies) is a Delaware Public Benefit Corporation (PBC or often called a B Corporation), which must by law follow Stakeholder Capitalism and not Shareholder Capitalism. Plenty of crypto organizations are set up as DAOs (Decentralized Autonomous Organizations), which is a group of people who come together without a central leader or company dictating any of the decisions, built on a blockchain using smart contracts and a currency of tokens that give them the ability to vote on decisions that are made around how the pool of money is spent and managed.

Hopefully that makes sense. Next week, I’ll talk about our Operating Philosophy at Bolster.

It feels like it may be a bit premature to write a post with this title here in the summer of 2021. Even as vaccines are rolling out fairly quickly, the combination of the Delta mutation of the COVID-19 virus and a bizarrely large anti-vaccine movement in the US, plus slower vaccine roll-outs in other parts of the world, are causing yet another spike in infections. 

However, I read Michael Lewis’s The Premonition last week, a bit of a “mid-mortem” on the Pandemic, and it got me thinking about what lessons we as a society have learned in these past 18 months, and how they can be applied to entrepreneurs and startups. I am particularly drawing on the few weeks I was deeply engaged with the State of Colorado’s COVID response effort, which I blogged about here (this is the 7th post in the series, but it has links to all the prior posts in order).

Here are a few top of mind thoughts. 

First, entrepreneurial skills can be applied to a wide range of society’s challenges.  The core skills of founders and entrepreneurs are vision, leadership/inspiration/mobilization of teams, and a fearlessness about trying things and then seizing on the ones that work and rapidly discarding the ones that don’t, quickly absorbing learnings along the way. If you look broadly at the world’s response to the Pandemic, and at Colorado’s response as a microcosm, you can see that the jurisdictions and organizations that employed those types of skills were the ones that did the best job with their response. The ones that flailed around — unclear vision, lurching from plan to plan and message to message, pandering to people instead of following the science, sticking with things that didn’t make sense — those folks got it wrong and saw more infections, hospitalizations, and deaths. 

Second, parachuting in and out of leadership roles really works but is a little bit unsatisfying. I think that, even in a short period of time, I got a lot of good work done helping organize and stand up the IRT in Colorado. It was very much an “interim CEO” job, not unlike a lot of the roles we place at Bolster. Without a ton of context around the organization I was joining, I still had an impact. The unsatisfying part is more about me as the exec than it is about the organization, though. I’m so used to being around for the long haul to see the impact of my work that I found myself pinging Sarah, who took over the leadership of the group after I left, Brad, and Kacey and Kyle on the teamfor a few weeks just to find out what was going on and what had become of Plan X or Idea Y. 

Third, I came to appreciate something that I used to rail against in the business world, or at least came to appreciate an alternative to it. I frequently will say something like “don’t solve the same problem four different ways,” almost always in response to people facing a big hole in the organization and trying to hire four different people to fill the hole, when likely one hire will do (or at least one for starters). But what Michael Lewis calls the “Swiss cheese defense” or Targeted Layered Containment (TLC) that worked pretty well as defense and mitigation against the virus while there was no vaccine totally worked. He calls it the Swiss cheese defense because, like a slice of Swiss cheese, each layer of defense has holes in it, but if you line up several slices of Swiss cheese just right, you can’t see any of the holes. Some masking here, some quarantining there, couple closures over there, a lot of rapid testing, some working from home where possible, some therapeutics – and voila – you can blunt the impact of a pandemic without a vaccine. The same must be true for complex problems in business. I am going to amend my approach to consider that alternative next time I have a relevant situation. 

Fourth, blunt instruments and one size fits all solutions to complex problems (especially in this situation, with multiple population types in multiple geographies) — even those with good intentions — can’t work, drive all sorts of unintended consequences, with a lack of feedback loops can make situations worse or at least frustrating. Nationwide or even statewide rules, quite frankly even county-wide rules, don’t necessarily make sense in a world of hot spots and cool spots. Statewide regulations for schools when districts are hyper local and funded and physically structured completely differently, don’t always make sense. There are definitely some comparables in the business world here – you’d never want, for example, to compensate people across all geographies globally on the identical scale, since different markets have different standards, norms, and costs of living. 

Finally, I am left with the difficult question of why all the preparation and forethought put into pandemic response seemed to fail so miserably in the US, when several nations who were far worse equipped to handle it in theory did so much better in reality. I am struggling to come up with an answer other than the combination of the general American theme of personal choice and liberty meeting the insanely toxic and polarizing swirl of politics and media that has made everything in our country go haywire lately. Big government incompetence in general, and failures of national leadership on this issue, also factor in heavily.  I also gather from Michael Lewis that the transition from one administration to another frequently involves a massive loss of institutional knowledge which can’t help. Of all these, failure of strong leadership stands out in my mind. 

The lesson for startups from this last point is important. Leadership matters. Eisenhower once said something to the effect that “plans are nothing but planning is everything.”  The thoughtfulness, thorough planning, communication and inspiration, and institutional knowledge that come from effective leadership matter a lot in executing and growing a startup, because you literally never know what COVID-analog crisis is lurking quietly around the corner waiting to pounce on your startup and threaten its very existence.

I attended two offsites in the last two weeks – both great in terms of seeing people in person.  Interesting how differently they handled COVID protocols, although they were different groups with different vibes.

One was a CEO conference for one of my VC’s portfolios.  There was a huge emphasis in all the pre-conference comms about COVID.  And lots of testing.  We all got mailed a very sophisticated in-house PCR test ahead of time to take and photograph/upload, complete with chemical reagents and some kind of centrifuge.  Then those of us who flew in for the event had to do an on-site rapid test before entering the opening reception and even had a side room to sit in for 15 minutes while we were waiting for the rest results.  Once in the room, everyone was super awkward at the beginning.  Should I wear a mask?  Do I shake hands?  Hug?  Wave?  Bump elbows?  But once we got into the flow of the meeting, people were more relaxed and interactive…even some close talking.

The other was my company, Bolster – our first ever “all hands” meeting in person (we started the company just 18 months ago and have people in multiple locations).  The COVID topic was almost nonexistent.  We only have 25 people, and everyone is vaccinated, no one is immuno-compromised, and the couple of people with young and unvaccinated children are very much not on lockdown (that could be more regional – I see that more in NY than in CA).  We simply asked people to get tested before they come on the honor system and then told people when we got there that people should do whatever they were comfortable doing in terms of masks and contact, no judgment.  There was no awkwardness that I could tell at all.

In terms of the meetings themselves, both were great – it was fantastic to be live with other humans!  While there is a lot to be said for the efficiency of 15 and 30 minute meetings on Zoom, that pattern of work can’t be 100% of your year.  It doesn’t allow for serendipitous hallway interactions or highly effective design collaboration like whiteboards and post-its do.

What neither group nailed was blending people actually at the offsite with a few people who didn’t want to, or couldn’t, attend in person.  That’s got to become the norm for offsites going forward, for sure.  Videoconference software or hardware/software combinations need to get better at supporting the hybrid environment for sure, but so do meeting facilitators.

All in, while I’m looking forward to traveling less in the future, there’s much to be said for meeting in person from time to time and figuring out how to optimize that time.

Return Path Core Values, Part II

As I said at the beginning of this series, I was excited to share the values that have made us successful with the world and to also articulate more for the company some of the thinking behind the statements.

You can click on the tag for all the posts on the 13 Return Path’s core values, but the full list of the values is below, with links to each individual post, for reference:

1. We believe that people come first
2. We believe in doing the right thing
3. We solve problems together and always present problems with potential solutions or paths to solutions
4. We believe in keeping the commitments we make, and communicate obsessively when we can’t
5. We don’t want you to be embarrassed if you make a mistake; communicate about it and learn from it
6. We believe in being transparent and direct
7. We challenge complacency, mediocrity, and decisions that don’t make sense
8. We believe that results and effort are both critical components of execution
9. We are serious and passionate about our job and positive and light-hearted about our day
10. We are obsessively kind to and respectful of each other
11. We realize that people work to live, not live to work
12. We are all owners in the business and think of our employment at the company as a two-way street
13. We believe inboxes should only contain messages that are relevant, trusted, and safe

As I noted in my initial post, every employee as of August 2008 was involved in the drafting of these statements.  That’s a long post for another time, but it’s an important part of the equation here.  These were not top-down statements written by me or other executives or by our People team.  Some are more aspirational than others, but they are the aspirations of the company, not of management!

The Best Place to Work, Part 0

I keep getting questions about a deck I’ve used several times at Techstars, Seedcamp, DreamIt, and the like which is called “7 Ideas for Creating the Best Place to Work.”  So today I will launch a 7-part series over the next 7 weeks to describe my 7 points.  As always, this is not intended to be perfect or comprehensive, but it is a bit of lessons learned over the last 12-13 years at Return Path.  It’s just 7 ideas – not the only 7 ideas.  And there’s nothing magic about the number 7, despite what George Costanza says.  Or Steven Covey.

Here’s the outline:

1. Surround yourself with the best and brightest
2. Create an environment of trust
3. Manage yourself very, very well
4. Be the consummate host
5. Be the ultimate enabler
6. Let people be people
7. Create a thankful atmosphere

Let’s go!  I will create a tag cloud for this series called Best Place to Work.

I realize I haven’t posted much lately.  As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004.  That inspired me to create a blog for entrepreneurs and leaders.  I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO:  A Field Guide to Scaling Up Your Business back in 2013.

Today is a special day in my entrepreneurial journey and in the life of the company that I started back in 1999 (last century!), Return Path, as we announce that Return Path has entered into a definitive agreement to be acquired by an exciting new company called Validity.  Press release is here.

Over almost 20 years, we’ve built Return Path into one of the largest and (I think) most respected companies in the email industry.  We’ve had a culture of innovation that has led to some groundbreaking products for our customers and partners to help make email marketing work better for consumers as well as marketers, and to help keep inboxes safe and clean for mailbox providers and security companies.  

But the company is unusual in many respects.  One of those is longevity. I’m not sure how many Internet companies started in 1999 are still private, backed and led by the same team the whole time, and generally in the same business they started in.  Another is our values-driven “People First” culture. From Day 1, we have believed that if we attract and retain and develop and invest in the best people, we will make our customers successful with great products and service, and that if we do right by our customers, we will do right long term by our shareholders.  While I know that not every employee who ever walked through our doors had a great experience, I know most did and hope that all of them realize we tried our best. Finally, I’m proud that our company gave birth to a non-profit affiliate Path Forward a few years back at the hands of executives Andy Sautins, Cathy Hawley, and Tami Forman.  Path Forward helps parents get back to work after a career break and helps companies improve their gender diversity and hiring biases and has already been a game changer for dozens of companies and hundreds of women.

Today, Return Path serves almost 4,000 customers in almost every country on the globe, with $100 million in revenue, profitable, and excited about the next leg of our brands’ and our products’ lives in the care of Validity.  If you haven’t heard of Validity before today, watch out – you will hear a LOT about them in the weeks and months ahead. They are an incredibly exciting new company with a vision to help tens of thousands of companies across the globe improve their data quality but also help them use data to improve business results.  That vision, inspired by a new friend, CEO Mark Briggs, is a wonderful fit for Return Path’s products and services and people.

To finish this post where I started, Fred’s exact words in that post which got this blog going were:

What does this mean for entrepreneurs and managers? It means that the first time you run a business, you should admit what you are up against. Don’t let ego get in the way. Ask for help from your board and get coaching and mentoring. And recognize that you may fail at some level. And don’t let the fear of failure get in the way. Because failure isn’t fatal. It may well be a required rite of passage.

All of that is true and has been great advice for me over the years.  But Fred left out one important piece, which is that entrepreneurs need to constantly thank the people around them who either work their butts off as colleagues in the business or who give them helpful advice and coaching.  Return Path’s journey has been a long one, longer than most, and the full list of people to thank is too long for a blog post.

I’ve noted Fred and Brad in this post already and I want to thank them and also thank Greg Sands from Costanoa Ventures, the third member of our “dream team” investor syndicate, for their friendship and unwavering support and good counsel for me and Return Path for almost two decades, as well as many other board members we’ve had over the years including long-time independent directors Jeff Epstein, Scott Petry, and Scott Weiss.

I want to thank my co-founders Jack Sinclair and George Bilbrey, and anyone who has ever been on my executive team, including long-time execs Ken Takahashi, Shawn Nussbaum, Cathy Hawley, Dave Wilby, Anita Absey, Angela Baldonero, Andy Sautins, Louis Bucciarelli, Mark Frein, and David Sieh.  There’s nothing quite like being in the proverbial foxhole with someone during a battle or two or ten to forge a tight bond. I want to thank Andrea Ponchione, my extraordinary assistant for 14 years, who keeps me running, sane, and smiling every day. I want to thank my executive coach Marc Maltz and the members of my CEO Forum for allowing me to be unplugged and for their friendship and advice.  I want to thank all of Return Path’s 430 employees today and over 1,300 ever for their hard work in building our company and culture together and for our 4,000 customers and partners for putting their faith in us to help them solve some of their biggest challenges with email.

Finally, no thank you list for this journey would be complete without saying a special thank you to my wonderful wife Mariquita and kids Casey, Wilson, and Elyse.  They deserve some kind of special honor for being inspirational cabin-mates on the entrepreneurial roller coaster without ever being asked if they were up for it.

This event may inspire me to begin writing more regularly again on OnlyOnce.  Stay tuned!

(This is the fifth 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, and 4.)

Thursday, March 26, Day 10

• Sarah continuing to take over and stronger by the day
• Sarah cleared me to go home, only one more person to ask
• Deep deep dive on Mass Testing – so good to spend that time 
• Pretty much got the strategy right – shocking we could get that close with so little public health experience – Kyle awesome – EOC leadership briefing
• That was most of the day
• Some downloads to Sarah and Kacey
• Feeling that two of our project teams are going sideways – that will be a big focus for me tomorrow before I leave
• Quick assignments for tomorrow
• Talked to Jared – he’s good with me going now that Sarah is in place and things are running.  Awesome!

Friday, March 27,  Day 11

• Download with a couple of the project teams to help get them back on track 
• This whole thing is one big exercise in Agile!
• Serendipitously might have found private sector partner for one of the teams in need.  Reminded of George’s great line, “when the student is ready, the teacher appears”
• Gov briefing on mass testing plan
• Spent a lot of the day on strategy/overview/retrospective deck.  Have to review it with Brad and core team members. Gov wants to get it in front of the National Governors Association to share learnings/best practices for the states behind us in this fight
• Gov thankful goodbye
• Brad thank you Haiku – so awesome – “You see things others don’t see”
• FInal team check-in, lots of nice thank yous from people on team
• Close out drinks with Sarah, Kacey, Kyle – persevered despite lack of corkscrew.  Poor Kyle’s shirt looks like he was standing next to a shooting victim
• Incredibly thankful moment with team – really like and care about these people – we’ve done such great work together – 11 days but feels like months and months
• Close out email to Governor and Chief of Staff about team

Saturday, March 28, Day 12

• Check out!  Fly home! Happy to see Mariquita, Casey, Wilson, and Elyse!

Stay tuned for two more wrap-up posts, tomorrow and the next day…

Seth Responds

About an hour after I posted a not so flattering review of Seth Godin’s new book this morning, I got an email from Seth with a couple good points worth responding to here.

His main points (other than offering me a refund, which was nice) were that (a) the book itself was very clear about its content — on the book itself (back cover, inside flap, marketing copy), kind of like a ‘live album’ for a recording artist; and (b) if I thought the blog postings were worthwhile, why  did I still feel like there was a downward trend in his writing?

Ok, so these are fair points.  Let me try to clarify.  I am 99% sure that I bought the book off the Amazon.com email which said “if you enjoyed other books by Seth Godin, then here’s his latest,” which prompted my robotic one-click order without paying attention to the fine print.  That’s why I was disappointed when I got the book.  My bad, I guess, although that’s somehow an unsatisfying thought as a consumer — that I should have paid more attention to the fine print.  Live albums from musicians usually have that in the title so the marketing is clear, and they still sell a ton, probably even more so.

In re-reading my review, I actually think it’s balanced — I do say there are a bunch of circumstances where the book is a must-have — but my use of the word “sell-out” was a bit harsh given the attempts to present the book as a compendium.  But the downward trend in my mind is more than just this book.  I think a lot of Seth’s writings have been hitting the same notes for the last couple of years, while I’ve been hoping to hear his next Big Moo.

I didn’t take up Seth’s offer for a refund, as I fall somewhere between (a) and (c) in my definition of why this is a must-have.  And while I’m at it, maybe I should rethink my earlier point that this whole blog thing isn’t about conversations.

Memory Lane or Dark Alley?

We had an interesting meeting today.  A small group of the old-timers at Return Path, including one of our founders who doesn’t work at the company any longer, convened a summit to brainstorm ways to reinvent our original, original business, Email Change of Address (ECOA).

For those of you who don’t know what it is, ECOA is a very simple idea — that people who change email addresses need help updating their personal and business contacts, and also their most trusted commercial email newsletter relationships.  It’s a free service for consumers, and a paid service for opt-in email marketers and publishers who use our service to reacquire their customers with renewed permission and a shiny new email address.

When we created ECOA in 1999, we were sure it was the proverbial $100 million idea (what idea wasn’t in 1999?).  More than six years later, the product is a success and profitable, but it never took off with that explosive growth we all imagined early on.  Return Path has grown a lot since then, both organically and through M&A, and since about 2002 or early 2003, we basically put the ECOA business on “auto-pilot,” tending to it as needed and making sure it still worked well for consumers and clients and was adequately competitive in the market, but no longer investing meaningfully in its growth.

Now that we’re much larger and have the time and resources to put into it, we decided earlier this year to pay some attention to our neglected first child and see what we could do with it.  Today’s meeting was the first step, and boy was it interesting.

So I can’t decide whether the process of preparing for and going through this meeting was like a pleasant walk down Memory Lane…or a scary run through a Dark Alley late at night.  It was fun having a conversation about a part of the business that was so important to us at one time in our lives (it was all we had!), and the group of us were literally reminiscing in the meeting about all the different thoughts and ideas we had for the business over time, as well as about different former colleagues who worked with us on the business.  At the same time, it was pretty painful to look at some of our original projections for market size and of course business size — not to mention some of the marketing efforts, Powerpoint templates, logos, and names that fell by the wayside.

The good news is, either way, we do have lots of great ideas for how to move the ECOA business forward con gusto…so look for more news on this front as the year unfolds.

(This blog post was first published as an article in Entrepreneur Magazine on April 15.)

Creating strong boards can help propel a board forward. Weak and ineffective boards hold a company back.

As a CEO, one of the most important (yet overlooked) tools in the playbook is building and leading a board of directors. Throughout my 20+ years of entrepreneurship, I’ve led four companies (including Bolster, where I’m a co-founder and CEO today) and served on eight boards. I’ve learned that strong boards can help propel a company forward and I’ve also witnessed how weak and ineffective boards can hold companies back. Mediocre or mismanaged advice, plus lack of accountability, can do long-term damage to a business as well.

Drawing from personal experience and anecdotes from dozens of Bolster’s client CEOs, here are some tried and true “Seven Habits of Highly Effective Boards.”

Habit 1: Begin with the board in mind

A lot of CEOs treat board curation as an afterthought, which means that boards tend to consist largely of who happened to be in their network at the company’s inception: investors. CEOs also tend to treat their boards as a distraction or an annoyance. Both of these lines of thought are problematic. 

Boards should be viewed as a CEO’s second team (along with their management team), as a strategic weapon that helps the company succeed and as an opportunity to bring new voices and perspectives. Research has shown the more independent and diverse a board is, the better it performs.

Habit 2: Be proactive about board recruiting

Devote as much focus to building a board as to building the executive team. This process is time-consuming and can’t be delegated to anyone else. Aspire to reach people who may feel out of reach. Asking someone to join the board is a big honor, so that ask becomes a good calling card. When recruiting, interview as many contenders as possible, don’t be afraid to reject those who aren’t a good fit and have finalists audition by attending a board meeting. Source broadly, too. Diversity is really important for many reasons; challenge any recruiter, agency or platform to surface diverse board candidates.

Habit 3: Keep your board balanced using the Rule of 1s

Whether it’s a three-person startup board or a seven-person scale-up board, it should include representation from all three director types: investors, management directors and independents. A few basic principles on board composition that work well are what I call the Rule of 1s: First, boards should include one, and only one member of the management team: the CEO. Even if co-founders or C-level managers are shareholders, don’t burn a board seat for a perspective that you have access to regularly. Second, for every new investor to the board, add one independent director, which is the biggest opportunity to introduce external perspectives. If your board gets too crowded with subsequent funding rounds, ask one or more investors to take observer seats to make space for independents. And don’t be afraid to change your board composition over time. Companies are dynamic and boards should be, too.

Habit 4: Cultivate mutual accountability and respect

While a board might seem intimidating, work past the power dynamic and push toward collaboration and mutual accountability. To ensure board members are prepared for meetings, keep commitments and leverage their networks, set the example by demonstrating preparation, consistency and reliability. By regularly delivering pre-read materials to the board several days in advance, the board will build a new habit. By soliciting feedback from board members after each meeting (and even offering them feedback), you’ll show the board that you’re listening. Over time, they’ll lean in, too.

Habit 5: Drive intellectually honest discussions

Even on the healthiest leadership teams, it can be scary to disagree with or challenge a sitting CEO (after all, they are still the one in charge!). But this power dynamic flips in a boardroom, which gives that group a unique opportunity to push and challenge business assumptions. While it may be tempting to look for board members with softer dispositions, it can be more beneficial to have tough, direct board members who aren’t afraid to express their opinions, but who are also good listeners and learners. My favorite discussions are conversations where I’m pushed to consider a different direction. It helps get more done, surfaces better ideas and increases the effectiveness of the company.

Habit 6: Lean in on strategic, lean out on tactics

Even board members who are talented operators have a hard time parachuting into any given situation and being super useful. Getting operational help requires a lot of regular engagement on a specific issue or area. But they must be strategically engaged and understand the fundamental dynamics and drivers of your business: economics, competition and ecosystem. This is an easy habit to reinforce in meetings. If board directors drift toward getting too tactically in the weeds, that’s great feedback to offer after the meeting.

Habit 7: Think outside the box

Good board members understand all the pieces on the chess table; great board members go one step further and pattern match to provide advice, history, context and anticipated consequences. This is an enormous benefit to CEOs focused on the minutiae of the day-to-day, particularly if a business operates in a trailblazing industry where many of the rules may not yet be written. As a CEO, if you’ve never seen something first hand before, it’s hard to get clarity and external perspectives, which is why it’s crucial that great board members bring pattern recognition and “out-of-the-box thinking” to their role.

At the end of the day, boards are there to support and direct a company. There’s no perfect formula, but by implementing these steps with a few healthy habits, CEOs can cultivate strong, dynamic boards for their companies.

People talk a lot about Imposter Syndrome — “What am I doing here? I’m not qualified to do X at all” regularly when it comes to women and people of color in the workplace. That is a real thing. It shouldn’t in any way be discounted. It’s painful to go through and painful to watch.

I’d guess that 9 our of 10 founders have Imposter Syndrome at least once during their founder journey. Maybe it’s even more like 99 out of 100. And I bet most of them have it more than once…some regularly. This may be even more true for founders from underrepresented populations, but it happens regardless of demographic.

Being a founder is inherently unnatural. Seeing the world through a different lens, inventing something, and being crazy enough to act on it, quit your job, raise capital, and convince other people to quit their jobs to join you on your journey is a tall order no matter who you are.

No founder’s journey exists without speedbumps and moments where things aren’t working and you feel like your company is going to die a horrible and painful (and worse, public) death – what my former Board member and friend Scott Weiss famously calls the WFIO moment (We’re F’d – It’s Over), popularized by Ben Horowitz in The Hard Thing About Hard Things.

Founders, it’s ok. We’ve all been there. Take a step back. Solve the problem. Change the approach. You’re not in the wrong place. You’re just having a bad moment. And most important, remember, you’re not alone.