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

I Am the CEO, Why Am I Confused About How I Should Spend My Time?

How a simple 2 x 2 matrix can help you become a better entrepreneur by understanding the key differences between efficiency and effectiveness.

A recently published New York Times article talked about how our brain tricks us into doing less important tasks, shining a light on how complicated the delicate art of time management can be.

You’d think that, living in an era of technology-enabled efficiency like we do, it would be simple to manage our time. We have time management apps to handle deadlines, reminders, workflows and all the nitty gritty details of delegation. But most of these solutions are focused on EFFICIENCY (doing things right), not on EFFECTIVENESS (doing the right things).

As an entrepreneur, this problem is multiplied exponentially. How and where you spend your time is more valuable than anything you have in your control. Before you ever get to automated workflows and collaborative calendars, you first need to figure out the basics of delegation.

I struggled with this topic as a young entrepreneur and tried every trick imaginable. I found myself wasting hours on tasks someone else could do better, perhaps because I enjoyed doing them. Other tasks I mindlessly handed over to others in the spirit of delegation, even though I was uniquely qualified to complete the task myself.

Unless you are acting as a sole proprietor, the challenge of balancing time management, capital utilization and strategic priorities is a never ending tug of war. And as your business starts to grow and scale, this tug of war becomes increasingly complex. You are faced with countless things to do with limited capital, time and team members.

Michael Smerklo, Co-Founder and Managing Director of Next Coast Ventures

At some point along my entrepreneurial journey—about the time that I was about to either get fired or committed to a mental institute—one of my mentors shared with me a simple four-step process based on the Eisenhower Matrix that helped me with this never-ending dilemma of time management. In fact, this exercise became an annual obsession for me as I sought the optimal formula for entrepreneurial success – in a growth company, the CEO’s job changes almost every three to four months

Step One – Use a 2×2 matrix to figure out what you are uniquely qualified to do

First, create the following 2×2 grid, with the y-axis describing your skill (either good or bad) and the x-axis describing your passion (love or hate) and list a couple of business functions that fit in the various boxes. The key is to figure out exactly what box a particular skill should fit in.

Here are the high level definitions in a bit more detail:

  • Upper Right – I am good / I love it: What task are you, as CEO, really good at doing? Not the things you think you are good at, but rather things that you have verifiable proof that you are uniquely qualified to complete. The key here is not only to determine what you are good at, but to assess how much you enjoy this part of your job.
  • Upper Left – I am good / I hate it: What are the tasks that you are actually quite accomplished at (naturally or from prior training) but bring you no pleasure? For example, I started my career as a CPA so I was actually very good at the financial part of the business, but I dreaded the annual budgeting process. The key here is to feel okay with this box too—not one loves every aspect of the job, not even the CEO.
  • Lower Right – I suck / I love it: This is a pretty dangerous quadrant and one that is likely the hardest to have an accurate read. Do you love engaging in deep product reviews … but flunked out of CS early on in college? Do you see yourself as a natural born sales person, but have never carried a quota in your life? Look long and hard at this box — as it is really, really is an important exercise in self awareness.
  • Lower Left – I suck / I hate it: Usually this seems to be an easy box to fill out, but this quadrant can be a real trap for a lot of entrepreneurs. The key is to make sure you really do suck at the function versus just don’t enjoy it. It is really easy to confuse these two emotions (enjoyment versus proficiency). Challenge yourself to make sure you aren’t actually quite good at something you don’t enjoy or vice versa.

Step 2 – List your company’s top priorities for the next six to twelve months

This should be pretty straight forward from your budget or business plan. Think of the four to five things that if completed will really move the needle for your business. Do you need 20 paying customers in the next 12 months? Is launching the next version of your product critical to moving the business forward? Or maybe your key outcome is centered around international expansion?

As a guide, these should be the tied to key metrics that you have shared with your board or that you have decided are critical for your next round of funding. Basically, your goal here is to list the four to five things that really are “make it or break it” for your business in the next 12 months. Here is an actual list I kept on my desk as a CEO—I called them the “Things That Matter” or TTM.

Step 3 – Compare your grid with your top priorities

Next, take a quick look at your grid. Take special note of how many of the top priorities for the business fall into the upper right quadrant of your grid. Here is an image of my grid from the early days of my CEO tenure:

By reviewing this grid against your top priorities, you can quickly determine where the gaps are and make decisions as to what you will focus on personally. You can also see where some big gaps might be and these should be your immediate focus as it relates to your team.

If your top goal is to acquire 10 new customers, but you hate selling, you better have a great sales leader on your executive team. If not, get hiring ASAP! On the other hand, if “get MVP in the market” is your key goal and you just happen to have spent five years in Product Management at Google, chances are that you can drive this outcome without a big external hire.

Step 4 – Allocate your time based on the grid

One mantra I learned early on was another simple concept: It is far easier to use the skills you already possess than to acquire new ones. In short, spend your time playing to your strengths and hire a team to overcome your weaknesses. For the grid, this means spending as much of your time in the upper right quadrant (good, love) and building out a team for the other areas of the matrix.

By using this quick four step process – and comparing it to your top business priorities – you can quickly see what areas you should engage in (even temporarily) and what areas you should quickly seek help in. This is, after all, the essence of effective delegation and time management.

NOTE: This post was originally published on Richtopia.

E2E: 20/20

Turning Thought Leadership Content Into Company Change with Matt Cain

Matt Cain is the CEO of Couchbase, a data management platform based in Mountain View, California. He read Michael Smerklo’s E2E post on time management and used it to construct an exercise for his leadership team during his company’s most recent offsite. Michael’s piece focused on using an Eisenhower Matrix to help CEOs learn to manage their time more wisely. Matt walks us through how he turned this thought leadership piece into actual company change.

How do you approach thought leadership exercises with your team?

I am constantly in pursuit of new approaches that can help us get better as a team and as a company. The timing of this particular exercise worked well because we were in the midst of our annual planning process – tackling important issues and building a new multi-year plan. I’m a big fan of multi-day leadership offsites because they give us the time and space to attack important issues in a meaningful way and go deep. We wanted to ensure that we were aligned on what really mattered to us, and how best we could achieve success. We are fortunate to be growing and scaling very rapidly, but ensuring we are tackling priorities in an aligned and efficient way is crucial. Michael’s framework was a simple, but creative way to start that exercise – exploring my personal priorities, initiatives, strengths and weaknesses. It was a really convenient way to allow me to personally demonstrate and model vulnerability while discussing what we want to accomplish as a group.

Matt Cain, CEO of Couchbase. Learn more about Matt below.

How did you use Michael’s thought leadership piece to create an actual team-building exercise?

I spent time ahead of the session preparing what I thought were our most important priorities, and then filled out the 2×2 matrix as Michael suggested in his article. At our offsite, I walked my team through the priority and matrix concept (pictured right). I then asked each of them to fill it out on my behalf and made it clear they would do so without seeing my draft. I explained we would then compare their versions to mine. Some people had worked with me for a long time, while others had not, but regardless the exercise established a trusting environment where we could have this conversation. Getting a level of vulnerability in the corporate arena where you can say: “Here’s something that I ‘suck’ at and here are some things I think I’m good at,” is not commonplace. Asking others you work with to tell you what they think you might be good at or “suck” at is even more rare. You can only enforce that type of dialogue by demonstrating a true willingness to take feedback and get better.

The Eisenhower Matrix from Michael's article.

What was something that surprised you about the exercise?

What really jumped out at me was the nuance behind the areas of perceived disconnect. As an example, during our initial review, several members told me that they thought I was good at networking, where I had it on my dislike list. I strive to build and maintain authentic relationships and connect with and help people, but do not enjoy networking for networking’s sake. My team assumed I enjoyed it because they perceived me to be good at it. In another example, one member of my team said to me that he thought I was really good at micromanaging, which he thought was an important skill, but yet another thing I don’t particularly enjoy. Even the term initially bothered me. We realized that I can be effective at diving into a function or issue in the organization and quickly get at the detail that matters to drive to resolution, which I agree is important. But we also realized I need to be encouraged to do so by my team because it isn’t the my first impulse. My natural instinct might not be aligned to what’s needed in a particular situation, so I have to rely on my team for help. But they need to first understand what those natural instincts are. No one can fix problems they don’t know about. We went on to explore triggers, histories, personality traits, and several other factors that brought us closer together.

What was something both you and members of your team agreed you struggled with?

Process and process creation. We now commonly refer to that as “lower left” activities for me and we have fun with that (them more than me sometimes!). Fortunately, we have process experts and operators within the team that take responsibility in these areas. It’s incredibly empowering to drive people to their “zones of genius” and remove things and are better done by others. Self-awareness emerges, but so too does insight into how leaders throughout the organization need to think about building diverse teams: thinking, experiences, perspectives, strengths, etc.

“You can only enforce that type of dialogue by demonstrating a true willingness to take feedback and get better.”

How do you make these findings actionable in the office?

After we filled out and discussed our findings of the matrix, we labeled each line item as either green or red. Green meant I or the team should allocate more time to these activities. Red meant we want to spend less time. In addition, we intend to use the matrix for all of my leaders, allowing them to go through the exercise and understand how they are over or underexposed in their roles. This will help them be their most effective selves and build the best teams they can.

What advice would you give rising CEOs about interesting thought leadership content they come across or advice they receive?

I’ve been studying leadership and team dynamics – and managing self-awareness for constant improvement – for as long as I can remember. Rooms in my house are covered in leadership and culture books from people I admire. My feedback on leadership is to follow your passion and to constantly be in pursuit of self-improvement. The best performers in the world, regardless of their profession (music, sports, business, etc.) tend to have the most coaches and are the ones that are always looking to get better. The way I pick up resources to help with self-improvement varies a lot over time: sometimes I’m into a book, sometimes I’m into retreats, other times I’m on a long-haul flight and get some direct insights just from being unplugged for hours. There’s no one model; do what works for you, just like working out. Find your recipe, stay committed, and follow your passion.

“My feedback on leadership is to follow your passion and to constantly be in pursuit of self-improvement.”

About Matt Cain

Matt has nearly two decades of experience leading global organizations, he is currently the President and Chief Executive Officer of data management platform Couchbase. Prior to Couchbase, Matt was President of Worldwide Field Operations for Veritas Technologies LLC after serving as Chief Product Officer for Veritas’ $2.5B business. During his tenure, he revitalized the company strategy, increased operational efficiency, delivered growth across the portfolio, and was instrumental in the separation of Veritas from Symantec. Matt previously held a variety of senior leadership positions at Symantec Corporation and Cisco Systems. He holds a bachelor’s degree in Electrical Engineering from Northwestern University and a master’s degree in Business Administration from the Stanford Graduate School of Business.