E2E: 20/20

How to persist through unprecedented leadership challenges (without losing your mind in the process)

Note: This blog was originally published in CEOWORLD Magazine.

The zoom meeting with a few of my junior team members started out just fine. As fine as it can be when you are on Zoom meeting number 11th (or was it 12th?) of the day. Then it happened. Three of my four kids burst into my home office, excited to show me an art project. I struggled and failed to hit mute. My wife had interrupted my previous meeting not 20 minutes earlier, so I was admittedly already on edge. As I yelled at them to get out and quiet down, all in front of my understandably horrified employee, I couldn’t help thinking to myself: Am I being a terrible dad or a terrible business leader? In that moment, it felt like I was failing at both.

Business leadership is hard in the best of times. But right now might be the toughest time to run, and especially to launch, a successful company.

Not only are CEOs contending with all of the usual C-suite responsibilities, but now there’s also a global pandemic, the pressures of managing a newly distributed workforce and a significant dose of social upheaval thrown in the mix. We are living out scenarios never covered in business school or considered in even the most thorough business plans. Virtually overnight, many leaders had to learn how to implement extreme health and safety measures, as well as how to support employee engagement and performance remotely for the very first time, all while struggling to acclimate themselves to a new work-from-home setup.

This situation has been overwhelming and stressful for everyone. There will always be something that comes from out of nowhere to knock you off course. But a leader’s job is to ensure her business continues to run on all cylinders no matter what — even in the middle of a global health crisis, a struggling economy or a period of societal unrest. Right now leaders are getting “all of the above” and are being asked to do more with little time to figure it all out. How can leaders meet the challenges of the present moment and continue leading confidently through adversity?

When everything feels uncertain and out of control, the one thing you can control is between your ears. Some call it grit. Some call it stubbornness. I prefer simply persistence. A persistent mindset is the only thing that will keep your head above water despite the deluge around you. It will allow you to remain focused and keep plugging away at your business goals no matter what. But it won’t happen overnight — it takes daily practice and dedication.

Here are five simple ways to develop a persistent leadership mindset:

Prioritize self care

Many professionals may have hoped the recent shift to remote work would offer a little more flexibility. Goodbye commute, hello work-life balance. I’ll finally crack that novel I’ve been meaning to read. I’ll even be able to play with my kids more often. Except, that didn’t really happen. In fact, a recent study from the National Bureau of Economic Research found that, in the aftermath of stay-at-home orders, workdays grew by 48.5 minutes and the number of meetings increased by 13 percent. We’re actually taking on more work and more stress, not less.

That’s why prioritizing self care is more important now than ever. Whether you enjoy meditation, running, reading, writing in a journal — whatever energizes and refreshes you, set aside time in your busy day just for you. You have my full permission to be selfish right now, not only for your own good, but for the benefit of your family and your team. Self care is imperative to your ability to persist and succeed as a leader.

Utilize Your Time Wisely

If you feel like time has no meaning lately, you’re not alone. The disruption to our regular routines has been warping our sense of time. Days blur into one another until, before you know it, an entire quarter has passed. But if it feels like each workday is really getting away from you lately, maybe it is. Are you being thoughtful about how you utilize your time? Here are a few things I recommend:

Use a simple “Eisenhower Matrix” to break down your priorities and separate what’s important, what can wait and what you need to completely remove from your plate.
Reevaluate your relationship with Zoom. (It’s not you, it’s me.) Not everything has to be a video conference. Sometimes a simple email or voice call will do just fine.
Put down your phone and step away from your laptop. Choose a time of day (4pm? 6pm? 8pm?) to disconnect from work and reconnect with yourself and your family.
Even though the lines between your career and personal life are blurring, you don’t have to be “on” all the time. Be purposeful and mindful with your time instead of allowing yourself to become overscheduled and maxed out.

Re-set Your Expectations, ASAP

I think we’d all love to flip a switch and poof: no more global pandemic. Then we’d have college football and movies again, and we’d all get to go back to work. That’s secretly what we’re hoping for, right? But here’s the thing: none of that stuff is happening any time soon. We’re not going back to normal. The sooner you can embrace this new reality, the better.

To persevere as a leader amidst chaos and adversity, it’s critical to reset your expectations as quickly as possible. The tide has already changed. You can either remain stagnant and let the water cover your head, or shift your mindset, start kicking and live to see another day. The most successful leaders will skip ahead, and do it fast. Fast forward your mind to get to the new reality, rather than hoping for a return to normalcy. That’s how you continue moving forward.

Equip Your Team to Persevere

Rarely has compassionate leadership been more essential than it is today. We’re all going through similar difficulties (or our own private hell, depending on who you ask). People everywhere are overworked, striving for balance and experiencing social withdrawal. Some employees might be dealing with health issues, while those with young children are massively stressed about the future of their children’s education, a burden that didn’t exist six months ago. If your team is crashing and burning, it’s tough to remain resilient as a leader.

Recognize what your people are going through and provide them with the extra support they require during this tumultuous time. In addition to approaching your interactions with greater empathy and compassion, create a framework within your organization that addresses these issues. Host open discussions about self-care strategies where team members can share ideas and discuss their own experiences. Go the extra mile to provide any sense of normalcy or connection, such as virtual team lunches, games or happy hours. Allow more flexible work schedules or perks for employees that continue meeting performance goals. In short, just give people a break.

Keep it All in Perspective

There’s a tendency in business leadership to speak in war analogies or in terms that imply “do or die” consequences. While business or financial outcomes might occasionally seem like the end of the world, the good news is, they are decidedly not. And thankfully, regardless of how serious a business issue may appear, it probably isn’t a matter of life or death.

A key leadership discipline is the ability to maintain a grounded perspective about what’s truly at stake while others are declaring the sky is falling. Yes, COVID-19 has real stakes. Yes, you should be focused and driven by performance goals. Yes, you should strive to ensure your company survives. But if you can keep a more realistic, pragmatic perspective, it will have a significant impact on your ability to remain calm and balanced in high-stress situations, and ensure your team stays that way too. At the end of the day, there are more important things than hitting your quarterly targets.

Business leadership is a marathon, not a sprint. There will always be unforeseen challenges ahead. You can’t control that — but you can control your mindset. Making self care a priority – and giving yourself and your team a break – is more important than ever. A persistent mindset will give you endurance when you need it most and allow you to power on past any obstacles.

E2E: Scale

A Bad Board of Directors Can Ruin Your Company

Note: This article originally appeared on on February 2, 2018. It has been republished here with the permission of its author, Neal Dempsey. You can find the original article here.

Companies live or die by the people who run them. The product is almost insignificant compared to the influence of humans, good and bad. That includes the board of directors. Founders should take great care when choosing their board members because an inexpert board of directors can bring a company down.

Not every company has choices about investor money or the board members assigned by the investors. However, think of investors and board members like a marriage. You’re going to be together for 7-10 years, so you’d better be sure it’s a good match.

While investors perform extensive due diligence on companies before giving money, founders don’t often take the time to scrutinize investors. That’s a mistake. It’s not only your right, but it’s your fiduciary duty to research your investors. Spend time with them – get to know them. Understand their strengths and weaknesses, just as they understand yours. Make sure you call other companies they’ve invested in and get a good understanding of how they work with their investments, function as a board member and interface with the CEO and management.

Neal Dempsey, Managing General Partner, Bay Partners

Just because an investor has previous successes doesn’t mean he or she is a good match for your company. Your board members need to understand how fragile companies are in the early days. They need to know how to move the company to a more secure position in the market. Maybe the board member has a big name with a big company, but that may not be what your company needs. Chances are, that person will give advice based on what a big corporation would do, and that can drain your resources and cash. Small companies need to be lean and act quickly. Big companies function on big revenues and slow, bureaucratic decision-making. If your potential investor or board member doesn’t understand the difference, he or she may not be right for you.

Early stage board members need to be more hands-on with the company. For example, one investor I know sat on the board of an early-stage company that was about to run out of cash in 30 days. Giving advice wasn’t enough. He worked with the founders to develop a tactical plan that would bring in the customers and cash they needed to survive. The founders drew a 30-day calendar on a white board. They labeled each day with a minimum new revenue number required to meet the 30-day survival plan. The investor was in the office every day during that time, helping them navigate challenges and find additional customers and revenue sources. Investors need to be big picture, strategic thinkers. But sometimes, they need to be doers and make things happen for the company. Investors and board members may not manage the company day-to-day, but in the early stages, board members are almost part of the executive team.

Choose board members with a breadth of experience that rounds out your management team. If you’re a technologist, bring on advisors who are good at sales and marketing. If the CEO is a sales expert, include a product development or technical advisor. Seek a human resources specialist to think through strategic hires. The board should complement the founders’ skill sets and bring needed expertise for growing and pivoting the company as needed.

On the other hand, the board shouldn’t run the company in place of the CEO. The CEO still needs to have the final say. One founder I know deferred to the board’s insistence on a particular hire to lead the North American office. The CEO did not think this person had a good understanding of early-stage companies, the market or his customers. The board liked this guy because he had successfully run divisions of big companies. In fact, the board all came from big corporations, so they were most comfortable with like-minded, big company people. The founder hired the person despite his apprehensions, solely on the recommendation of the board. That hire almost ended his company. The new hire spent most of the company’s investment money on all the wrong things and accomplished none of the company’s goals. The hire set the company back years because they couldn’t get a second round of funding. The board misguided the CEO because they didn’t have early-stage experience. Today, the founder says his big regret was not only choosing a board who didn’t understand his business, but blindly following their advice.

Conversely, one of the companies I invested in had a CEO who was quite skeptical about taking investor funding. She carefully interviewed each potential investor. One venture capital (VC) firm pulled what we call a “bait and switch.” They put their top leader forward while courting the company, and then when they were ready to close the funding round, assigned a younger, inexperienced associate to sit on this company’s board. The VC firm thought they had the deal locked in, but the CEO did not respect the inexperienced board member and as a result declined the funding deal. Stunned by her decision to leave them out, the VC firm begged to repair the relationship. The founder only let the investors join the funding round once she noted in the contract that the young associate would not be allowed to sit on her board or advise her company, and the most senior partners would be the only ones to interact with her. That was a brave decision, but she knew over time, that board member would be fatal to her company. A lesser funding round might make things harder in the short-term, but avoiding a toxic board member was the right long-term decision. In the end, by standing up to the investors, she got everything she wanted.

Be as selective with your investors and board as you are when choosing a spouse. Find investors with experience in your market and early-stage companies. Don’t worry about getting the flashiest name you can get. Make sure advisors truly understands your vision, business and bring real value. Get reference checks from their portfolio companies, customers and employees. Learn what they’re like in the heat of battle when things are tough, because there will inevitably be hard times. How do they solve problems? How do they mentor founders through the difficult trials? Turn down a bad investor or board member if necessary. Most importantly, be the driver of your company, even after you’ve selected your board. Follow your gut. Chances are your instincts are right.

About Neal

Neal Dempsey is the managing general partner at Bay Partners. He joined Bay Partners in 1989 and focuses on SaaS, software, enterprise, Internet and eCommerce companies. He created the Dempsey Foundation and founded the Center for Innovation and Entrepreneurship at the University of Washington Foster School of Business. He had 3 IPOs in 2012 with Eloqua (which was acquired in 2012 by Oracle for $871 million), Enphase Energy ($242 million) and Guidewire Software (market cap: $2.09 billion). Dempsey is an adventurer who has climbed six of the seven tallest summits in the world. He says of his propensity for risk: “My philosophy is to always do something that scares you, which includes investing sometimes. But that’s when I feel most alive.”

E2E: Scale

Should the customer success function report to the head of sales or the CEO?

For any recurring revenue business, there are seven key reasons why the Customer Success function should report directly to the CEO and NOT the Head of Sales.

Customer success has (finally) started to become an established function within SaaS companies. As a startup begins to scale and move from ideation/product creation phase into revenue generation, it quickly becomes clear that resources are needed to help manage customer relationships AFTER the initial sale.

I have been an advocate of Customer Success and the importance of both the function and mindset within SaaS/Recurring Revenue companies since dinosaurs roamed the Silicon Valley…

As recurring revenue business models have become the standard for technology companies, it has become clear that Customer Success is critical for sustaining growth, profitability and customer reference-ability. In short, if you don’t get Customer Success right, nothing else matters.

As a result of this increased importance, it has been refreshing to see most emerging-growth companies building out functions that focus on all aspects of Customer Success – from onboarding and adoption to support and eventual renewal of the subscription agreement. This function can also take on responsibility for upselling and/or cross selling of additional seats or subscriptions.

In short, this is a critical function for any SaaS/Recurring Revenue business.

But here is the question I get asked more often than not about this function – should this function report directly to the CEO?  My quick answer – why wouldn’t it?

The normal response from CEOs that I work with goes in one of two directions:

  • Well, revenue is involved (cross sell, up sell, renewal) so my Head of Sales is arguing that it should report to her.
  • I already have so many direct reports (sales, CFO, product management, engineering, HR, marketing) that I can’t imagine adding another direct report.

My response is pretty simple and direct (before making sure, of course, that I remind EVERYONE that I was once a CEO so whatever I say must be 100% accurate)….What is the ONE THING that will make or break the success of your business? Hard to answer with anything here EXCEPT Customer Success!

Here are THE seven KEY reasons why Customer Success should report to the CEO:

  1. VISIBILITY: It lets you see exactly what is happening with your most important asset besides your employees: your customers.
  2. CLARITY: Having Customer Success separate from Sales gives the organization visibility into what is really happening after a prospect becomes a customer – and takes away a lot of the typical finger pointing between sales, product management / engineering and professional services.
  3. METRICS: When the Customer Success function reports directly to the CEO, an organization can develop specific metrics that really determine the health of the customer BESIDES how much money they are spending (i.e., sales).
  4. BALANCE OF POWER: In most emerging-growth SaaS businesses, the power within the organization typically sits first with product/engineering (“we need to build something that works”) and then shifts to sales (“we are screwed if we don’t sell something”). By having Customer Success sit OUTSIDE of either of these functions, a CEO can avoid a lot of the natural power plays that happen (resource gathering, budget disputes, etc.) and stay focused on the customer.
  5. SALES FOCUS: If Customer Success reports to the Sales function, there is too much potential for either the customer getting ignored (“I have to make the quarter”) OR the customer’s needs becoming a distraction (“We missed our f#cking quarter because of these customers”). The sales team’s job is to sell – keep it that way.
  6. FEEDBACK LOOP: As a CEO, one of the hardest things to do is to get clarity on what is really happening inside and outside the business. The ultimate is to get insight into what is happening in the magic loop – Plan and Build (product management and engineering) vs. Demand and Sales (Marketing and Sales) vs. Customer Experience (Customer Success).
  7. SIGNALING: By having this function report to the CEO, it tells the world (internal and external) that the organization really does care about the customer. It’s pretty hard to say “the customer is king” when the function isn’t sitting in the Monday morning Executive Staff meeting.

The advent of the Customer Success function is refreshing to see for technology companies, and the industry has come along way from the early days of “sell now, beg for forgiveness later” mindset.

By making the Customer Success function a direct report to the CEO, the long-term health and wellbeing of a business is significantly enhanced.

And it also takes one more excuse away from those Sales Executives when they miss the F#cking quarter – that fact alone might make it all worthwhile.

E2E: Scale

On Board Management: Wise words from 4 Silicon Valley legends

What I learned from Bruce Dunlevie, Bill Campbell, Marc Andreessen and Al Davis about creating, building and managing a world-class board of directors.


As an entrepreneur, how do you view your board and the importance (or lack thereof) as it relates to your business?

Throughout my entrepreneurial journey, I learned a lot, made some mistakes, and eventually developed an approach that transformed my board into a strategic weapon.

But it didn’t come naturally or happen overnight – I made some silly missteps and had to modify my mindset when it came to board management quite a bit as I went.

If you’re anything like me, you struggle with the best way to assemble, manage and interact with your board, especially given all the other things you have on your plate while scaling your business.

I expect that you are always trying to figure out how much time to devote to the board in general and why, other than their presence as a necessary evil, you should even spend time thinking about this topic. A board can really help you and even might be the difference between success and failure in your journey – so I encourage you to avoid the temptation to de-prioritize your board in lieu of other initiatives.

Rather, by learning from my three key lessons, I hope you will see your board (or the benefits of having a strong board) in a new light. And with a new perspective, you will be able to use your board as one more arrow in your quiver that will help you build an amazing business.

Here are the mistakes I made, the teachers who helped me modify my approach, and the benefits I derived from these learnings.


There is an old joke about this board Management that is a good place to start for this lesson:

What do board members and mushrooms have in common? They BOTH should be treated the same – kept in the dark and covered with shit.

For the first few years I was running my company, I didn’t really engage my board in a strategic manner and kept most of the meetings high level – making sure that I had every questions answered BEFORE I walked into the board room.

Or I would fill board decks with pages and pages of details – making sure that we spent so much time in the meeting going through the materials that the opportunity for free form discussion or dialogue never materialized.

Of note, I wasn’t doing this on purpose or to hide anything – rather I just didn’t know how to get much from my board. As a result, I was either giving them too much or too little information, so by default the meetings were never really that constructive.

And while I would get through the meetings just fine, I NEVER realized I was “keeping my board in the dark and covered in shit.” AND yet I found myself feeling more and more frustrated after every meeting. I wanted more insights from the people who were most likely to help me look around the corners I hadn’t seen before. But I just didn’t know how to get what I needed from my board. 

And while I understand (FULLY!) how painful it can be to deal with annoying, boastful, arrogant, know-everything board members (I better stop now), I did ultimately learn how to get the best out of my board without wasting huge cycles to do so.

For this lesson I owe a debt of gratitude to one of my best board members, Bruce Dunlevie,  founding partner of Benchmark Capital, the preeminent Venture Capital firm in Silicon Valley. When Bruce first joined my board, I was consistently making the “too much information” mistake I described above – frankly giving my board too many details and hoping they would – from the same minutiae I had scoured – divine some nugget of information that I had not yet gleaned myself.

After one particularly frustrating board meeting, Bruce called me to give me some incredibly sage advice.

Bruce could see what was happening from a mile away – because HE HAD seen so many other Entrepreneurs fall into this trap – and he could emphasize with me and my effort to deal with a powerful board. And, like any good board member is apt to do, Bruce asked me a couple of simple questions that changed my perspective completely:

“Mike, does anyone on the board know as much as you do about your business? Seriously – how big is the gap between what you know about the operations versus what the board even understands about the business. Have you taken this gap into consideration when building the board agenda and supporting materials?”

As I reflected on this question, I quickly reminded myself that I spent close to 80 hours (at least) A WEEK thinking about my business – while my average board member thinks about the same topic for 40 hours A YEAR (at best).

This is a huge discrepancy, and noticing this delta is probably the most important realization for any entrepreneur when thinking about how to manage a board, set an appropriate agenda, or build a compelling board deck. Simply put: don’t attempt to get your board up to the same level of understanding as yours. Rather, use this gap to your advantage.


The first step here is a mindset shift. Once you have made this shift and stop trying to get your board to the same level of understanding that you have about your business, you will change both the context and content you use in your board communication. By setting the right agenda and developing a board package that is good mix of key operational updates AND open-ended strategic discussion, you’ll be amazed at how much more you can get from your board in very short order.


Another mistake I made along my journey was giving my board too much input on the operations of the business. This is a pretty common mistake and is more prevalent with first-time entrepreneurs, especially those who have raised institutional capital from a PE or VC firm where the relationship between capital provider and entrepreneur is still being cemented.

The mistake here is to give your board too much credit – assuming the members know more than you do – or assuming that their suggestions must be followed to a fault.

One of my early mentors was the legendary Bill Campbell. He was on the board at Loudcloud / Opsware, and I was fortunate to stay in contact with him and get his input from time to time during my journey.

Bill is simply the best in the business and has forgotten more about leadership and entrepreneurship that most of us will ever know. I was speaking to him about this very topic and he quickly noticed my attitude of giving the board “too much credit” and how this approach was causing me to miss a real opportunity. To help educate me, he asked me one simple question:

“Mike, how do you see your job, as CEO, as it relates to the board?”

After we talked openly about this question, I came to the following key realization about my role versus that of the board and it helped me immensely.

My responsibility as CEO / entrepreneur was to make decisions and give the board insight into both my decision-making process and the direction I was taking the business. The board’s job was to give me feedback that I could choose to use to inform my decision.

The bulk of my communication – say 98% – with the board was really about seeking input, with the remaining 2-ish% being major corporate decision-making that required board approval. As such, I needed to make sure my mindset and material reflected this – specifically that the lion’s share of my board interaction was really about seeking input to help me with MY decision-making.

As Bill said to me at the time (in a gruff way that is classic Bill Campbell):

“You are running the f-ing business. You are making the decisions. If you get enough right, you keep your job. If you mess too many up, then the board should fire you. It is really that damn simple.”


I then realized that the board’s job was to determine if I was making more good decisions than bad. And if my decision-making success rate dropped below an acceptable level, the board then would need to make a decision about my ability to do my job. Once I accepted this relationship, I felt more empowered as a leader and saw my relationship with my board become much more productive.

As part of this, Bill also taught me a GREAT phrase that summarized this relationship – I used it at least once a board meeting whenever a board member wanted to give really me specific advice on a problem I was trying to solve:

“That is super input. I really appreciate your point of view on X (insert detailed operating issue here). I will take your input into consideration, and if need be I might follow up with you to get more of your perspective here.”

Try it the next time a board member is espousing some action that she is certain will work for you. Trust me, you will start to use this more and more and will savor the lack of response it generates!


During the early days at Loudcloud (which became Opsware), I was fortunate to get to travel a great deal with one of the four founders of the business, the legendary and prolific Marc Andreessen. On one of these trips, in early 2000, I was asking Marc about how he was assembling the board for Loudcloud and why he had recently recruited Michael Ovitz to the board.

Of course I knew of Michael Ovitz, the legendary Hollywood super-agent and founder of CAA – but I wasn’t sure how this background was relevant to the technology company we were building. Marc’s response to my question was fast and clear to (and a bit dismissive, but Marc responded to most of my questions that way):

“I want every advantage I can get to build this business. And that includes the board. Michael is a great entrepreneur – he knows how to build a service business and can help us increase our profile, talent-acquisition model, and approach to client relationships. Plus, he is outside of The Valley and brings a fresh perspective that we can’t get anywhere else.”

Now Marc is a special talent and has for a long period of time played at the highest level of power and influence in the technology industry, so his ability to attract talent to his board – even back in 1999 – falls into the category of outlier.

But my point here is that Marc was both clear about what he was looking for and how it could help him build a business. And then he went out and recruited board members that fit this profile. (See a great interview between Marc and Michael here)


If you think about this perspective and ask yourself a few questions, I expect you will think a bit differently about who is on your board and how each member can do more to help you win in your business.

  1. Are you getting the right level of feedback from your board around key strategic issues?
  2. If you think about the 2–3 top strategic issues the business is facing, do you have expertise on your board to help you address these issues?
  3. If not, do you have a plan to develop your board in a logical, thoughtful way to change the composition for better alignment between #1 and #2?

When I was running ServiceSource, I took this learning to heart and consistently looked at my board to see if I had the best talent in the room to help the business grow and succeed.  And with each important milestone that we were looking to achieve, I would try to find a board member to help the company get there.

This helped me get board members with experience in international expansion, sales and marketing, cloud application and even financial expertise when we were getting ready to go public.

And I shared this mindset with the board openly and regularly, so they became part of the process and understood exactly where I wanted to take the board.


As an entrepreneur, you have a really, really hard job, and rarely do you have a lot free time to devote to things that are not going to help you compete and win in the marketplace.  I know firsthand just how hard it can be to deal with a board – and I can understand why a lot of entrepreneurs see little or no value in dealing with the board.

But if you think about your board – both management and composition – a bit differently, you find you’re missing a key trick.

Al Davis, the late, great and notoriously fiery owner of the Oakland Raiders was fond of summarizing his management philosophy with his head coaches in very simple terms:

As the entrepreneur, you are the head coach and your job is to win. It really is that simple.  So if you want to win, it is pretty important to think about how you can get more from your board to help you make this happen.

  • DON’T treat your board like a mushroom. It might be easier to run the business in the short term with this approach, but it isn’t sustainable and, more importantly, you are missing a real opportunity to get their input on the RIGHT issues.
  • DON’T treat your board like they are running the company. That is your job, and you have the responsibility and perspective that no one else really can understand. So keep your board in the loop, seek their input, and engage them openly. But remember my magic phrase (trust me, you will use it more than you think), and know the difference between running the show and board governance.
  • DO assemble a board that can be a strategic weapon. You need *every* advantage you can get in your fight, so think about how the right board member can help you get leg over the competition. Be clear about what needs you have and how a particular skill set on the board can help your business grow – and then aggressively recruit for a top talent to fill this spot on your board. You will be surprised by how much this can help you on the journey.

Think of your board like any weapon in your arsenal, then just win, baby. Just win!