Tuesday, May 28, 2019

On Spring and Being Relentlessly Resourceful

Complex elegance
Relentlessly resourceful
Imagining Growth

Paul Graham wrote a short blog post back in 2009 describing the characteristics of a good startup founder. His two-word description was “relentlessly resourceful”. I came across this great post again this morning after listening to Harry Stebbings and the 20 Minute VC interview with Geoff Ralston, President of Y Combinator. Ralston noted that he wants to invest in “resourceful and determined” founders, “people who can build”, founders who he believes are going to be able to “create things.” These descriptions of great founder characteristics sound simple, almost silicon valley cliche’, but they stuck with me this morning as Kiya and I took our hike and I thought about today’s haiku.

Spring in the mountains is endlessly inspiring. Growth is all around us. It’s not just the new growth that comes with spring that is inspiring though. It is the relentlessly resourceful growth. Trees grow through cracks in the jagged rocks, grass pushes through layer upon layer of fallen decaying aspen leaves, and the flowers of the mountains bloom in exceptional and brilliant ways to compete for attention. My wife inspired me to capture photos of the spring, and the close encounters, like the one above, have been eye-opening. So much complexity grows beneath our feet. There is elegant and beautiful complexity that grows through the spring rains and the mountain storms. There is relentless and resourceful growth in the mountains and it is simply amazing.

Graham notes in his post that there are probably other fields where “relentlessly resourceful” might be a recipe for success. I could not agree more. I believe that Client Experience teams (aka Customer Success) benefit as much, if not more, than any other function from individuals who demonstrate relentless resourcefulness. Serving customers in today’s enterprise software market is incredibly challenging. There is so much technology chasing our customer’s attention. I read recently that the average knowledge worker uses 36 cloud services in their day-to-day work. Thirty-six! And it’s not just the technology that complicates how we serve our customers. Our customer’s lives are increasingly complex as today’s dynamic organizations change, restructure, and evolve. Breaking through to our customers is a challenge but that is only the beginning. Today’s enterprise customers live with and are often obsessed with consumer-grade technology and experiences. Their expectations for enterprise technology are no different. Serving them and delivering the outcomes they need requires everyone in CX to become relentlessly resourceful.
How do we become relentlessly resourceful? As startup investors, founders and leaders how do we encourage and develop this critical characteristic in others? Here are three ideas.

Encourage Authenticity

Christopher Lochhead wrote a great piece this morning on authenticity. I have long admired Lochhead’s own authenticity in designing legendary businesses and brands and his Legends and Losers podcast is a must listen for anyone interested in building something truly unique. As Lochhead notes, “People don’t want to be sold on an idea — they want to learn from a real person through a natural conversation.” To be relentlessly resourceful we need to encourage, and not just encourage but actively draw out, the authenticity in ourselves and others. Authenticity is an exceptionally powerful resource that too often sits on the shelf. Individuals are encouraged, either directly or through implied norms, to look and act like others. Almost by definition, relentlessly resourceful individuals will leverage all of their strengths, including their own unique voice, style, and ideas, to break through and drive outcomes for customers.

Give it Room

Another silicon valley cliche’ is the idea of “failing fast”. Benedict Evans had a great post some years ago “In Praise of Failure” that did an excellent job of articulating the value in creating room to fail. As Evans explained, “You need to ask not whether this idea will fail, let alone whether it could fail, but rather, ‘what would it be if it worked?’ You need, in a sense, to ‘suspend disbelief’ - to put aside your normal human risk-aversion and skepticism, accept the probability that it could go to zero, and ask if this could 'put a dent in the world', and if so, how big.” Despite the article’s unfortunate title, and how many have misinterpreted this well-worn sound byte, building relentless resourcefulness is not about celebrating failure but allowing room for it. It is about accepting that in order to win big you need to play big and try new things and yes, sometimes those big ideas will fail. To be relentlessly resourceful and develop that characteristic in others we need to create room for them to fail. Practically that might mean giving a manager room to make a hiring decision that you don’t completely agree with, giving them the space to test a new methodology that you don’t completely buy into, or focusing on stretch assignments for well placed passive employees on the team. Relentlessly resourceful is not about casting seeds into the wind and telling your team it is okay if they fail but giving your team the opportunity to plant, nurture and grow in unconventional places and ways.

Push. Hard.

Many people have achieved great things without being challenged along the way. That doesn’t sound quite right, does it? Challenge is essential to achieving great things. Pushing one another enables us to run faster. Ben Horowitz wrote in The Hard Thing About Hard Things, “Most business relationships either become too tense to tolerate or not tense enough to be productive after a while. Either people challenge each other to the point where they don’t like each other or they become complacent about each other’s feedback and no longer benefit from the relationship.” Horowitz noted about his relationship with Marc Andreessen, “Even after eighteen years, he upsets me almost every day by finding something wrong in my thinking, and I do the same for him. It works.” To help our teams develop the relentlessly resourceful characteristics that will help fuel our business success, and their ultimate career success, they need the challenge. I am not suggesting, which might surprise some people that I have worked with, that everyone should be a hard ass all of the time. But I am suggesting that winning the leadership popularity contest is not a recipe for driving or delivering exceptional results. To develop ourselves and others we need to push and push hard. We need to challenge one another and sometimes that will be uncomfortable. Doing so provides the friction needed for growth and can help to create the environment for relentless resourcefulness.

There is a lot we can learn about driving startup success from a simple hike in the mountains. The flowers beneath our feet grow and flourish when they excel in their ability to attract the pollinators. They do this through unique and innovative designs. In our startup journey, success is often realized through our individuality and authenticity. Mountain flowers grow when there is room. When there isn’t, either growth doesn’t happen or, like the trees pushing through cracks in the stone, they make room. Similarly, for our teams, we need to make room to grow. It won’t always work out but we need to take our best shot. Finally, like spring growth in the mountains, we have to push, often hard, to find the sunlight. The fallen aspen leaves, the decay of prior seasons, can bury the flowers if they don’t push hard enough to find the light. The strong survive. In our startup lives, we need the challenge, we need to push and be pushed in order to thrive. Life is relentlessly resourceful. With work, we and our teams can be as well.   

Thursday, May 16, 2019

You're Distracted and Chasing Rabbits

In her element
Prepared to go the distance
Is that a rabbit?

Kiya is a good dog. A true Alaskan Malamute she is strong, friendly and loves hiking the snow-covered trails as much as anything. Kiya is also a bad dog. Like most Malamutes she can be stubborn, has a high prey drive that takes control and sheds like … oh god how she sheds.

Kiya is also easily distracted. We hike every day, often along the same trails behind our home in Park City. But every time is like the first time. She pulls me along the trail to explore the same tree she has smelled a hundred times. She grabs the perfect stick, really more of a tree, from the trail and carries it as happy as she was yesterday when she rediscovered it for the 10th time. FULL STOP! Drop the stick. “DID YOU HEAR THAT?” A rabbit, a leaf falling, often nothing at all. High Alert! She scans the forest, ears perked, ready to go. And then we are moving again. It was nothing. It’s often nothing. Kiya is easily distracted.

We are all easily distracted. Like the mysterious rabbit that teases Kiya’s imagination our dark forests of technology haunt ours. The snap and rustle of our communication tools keep us all on high alert. WAIT! DID YOU HEAR THAT? Someone was commenting on my post. Someone liked my status update. Someone browsed my profile. Is that an email! Oh, wait. It was nothing. Back to work.

We are all too easily distracted. Work for a bit. See the ping from Slack. Work for a bit. Hear the ping of Twitter. Work for a bit. Suspect maybe another email… and on we go. Our rabbit is out there. Like Kiya, we must be vigilant if we are going to catch it. I read recently that the average knowledge worker only spends about 3 minutes on any given task before switching. 3 minutes on a task and 2 minutes before switching digital tools. It’s crazy! Is it the fallacy of multitasking or is it an obsession with rabbits? The same post noted that we find only an hour and twelve minutes a day of completely focused work. Six hours per week. Only 15% of our work week is focused work. The rest, rapid task switching, falling into the trap of multitasking, searching for… oh look M&Ms are on sale.

Kiya’s distraction drives me nuts. Co-worker distraction also drives me nuts. When new hires join my team I admit to them, very early on, that I have three major pet peeves. Showing up late to meetings, not being on camera when we are on Zoom meetings and... multitasking. Especially when we are on calls together or with clients, it’s just not okay. We all know better but… RABBIT! A few years ago I wrote a very snarky blog post about multitasking, specifically challenging that ass in the room to put down the phone. With almost 30k views I think it resonated with others as well. We really all do know better. We all hate that guy. The multitasking, the distraction, the… RABBITS!

Unfortunately, they aren’t going away. The well-worn paths of our daily habits will have distractions that continue to multiply like so many rabbits. Our 15% of focused productivity each week will be chipped away at until it is all task shifting and bouncing noise back and forth. Unless… we put down and turn over the phones, turn off the notifications, and challenge ourselves, and those we lead and care about, to focus. It's hard. No one likes the reminder. But, we are better for it when we do. When it’s time to focus, focus. When it's time to find rabbits, take the dog for a walk.

Friday, May 10, 2019

Chilling Out

Overwhelmed with angst 
Searching for resolution 
Maybe, just chill out

This morning I saw #DearMeTenYearsAgo trending on Twitter and I paused to think of all of the things I wish I had known ten years ago. It's a long list. I was 35 ten years ago and had already mastered the art of the mistake. Divorced twice, five kids with six different mothers, addicted to Skittles on wheat bread, three felonies in five states and all sailboat related to say nothing my neurotic habit of overthinking things. There had been tough times. One of the many, many, things I wish I had known ten years was to just chill out.  

For much of my early career, I had been overwhelmed with angst. Some of this anxiety was positive. It motivated me to over prepare for meetings, to speak less and listen more, and to work harder than I needed to on small things. Just as often though, maybe more often, the angst led me to worry about things that I couldn't control like what people thought or were saying about me. It led me to worry excessively, neurotically, about how my career was progressing. Was it fast enough? Was the role big enough? How did I compare to my peers? It led me to incredible frustration when things, and you can name a million of them, didn't go the way that I expected them to. So much of my career has been filled with angst. Not just angst though. 

So much of my career has been filled searching for resolution. Not just any resolution though. The resolution that I want. The resolution that I expected. Promotion decisions that didn't come quickly enough, project assignments that didn't land the way that I wanted them to, co-worker interactions that left me frustrated or outright angry. So much of my early career was spent frustrated and looking for resolutions that didn't come fast enough, didn't turn out how I wanted them to or just as often never came at all. 

I think many people feel this way. Overwhelmed with internal angst and searching for resolution. We compare ourselves to others that we don't really know. We worry about what people think of us when they don't think of us at all. We struggle to compete on things that don't matter and neglect the things that do. We search for answers we don't need and waste the energy we don't have on the search. We all get spun up in our own thoughts and detached from reality. 

My #DearMeTenYearsAgo, just chill out. Relax. Nothing is as serious as it seems at the moment. The angst, the anxiety, the worry is all wasted. Ten years later you won't remember because it won't matter. It never mattered. Just chill out. 

Monday, May 6, 2019

Choosing Adventure

Moving fast or slow
Obstacles are relative
Choosing adventure

"It is hard becoming a new version of yourself." A simple understated line from season 4 episode 6 of "Billions". It is hard. The obstacles standing in your way are all relative. Others might see them as small. They might see them as insignificant. But obstacles are relative. Everything is relative. The challenges that stand in your way are yours. It is hard to become a new version of yourself. It is even harder to become the best version of yourself. 

Today I have been struggling to become a new version of myself. Habits that once served me well no longer do. They are simply no longer relevant. My addiction to being hyper-responsive on Slack or email serves no one. After deleting the Slack app there is no longer even anything to respond to. But I pick up my phone. I look and see the empty home page slot where my attention once lived. It is mindless. The habit is empty. Truth is, I see now, it always was. Once it is gone it is hard to remember why it ever mattered. 

I am struggling. I instinctively check email. The little red notification, that magical little flag that validated my checking email, doesn't appear. It's turned off. I still check. It is a hard habit to break even when there is no validation at the end. There is no little red icon telling me that I am important to someone. Its absence is unsettling. I am embarrassed by the habit. Why did I ever feel like I needed to constantly check this? Did it ever really matter? Why am I holding my phone? When the little red validation is gone it leaves a hole. It leaves a question. 

It is hard to become a better version of yourself in part because who we are - who I am - is formed by habits and routines that are often mindless. Ideas that I latched onto early in my career became a part of who I am. Always on. Always at the ready. A click away. It is hard not to be that person. 

It is an obstacle that may sound insignificant. A bad phone habit. That's all. Who doesn't check their phone too much? Who doesn't want to see that little red alert that begs for your attention? It's all relative. It's not just the checking that keeps me from becoming a better version of myself. It's the need to keep checking. Checking when it no longer makes sense. Checking when it never made sense. It's hard. Hard to break a habit of external validation. Harder still to create a new habit. 

It's all relative. Maybe for you, the little red icon doesn't mean anything. Maybe for you, it is a like from a friend on your Instagram or Facebook post. Maybe for you, it is a congratulation on your LinkedIn post. Maybe for you, it is [ fill in your own blank ]. We all have them. Our mindless habits. Our work habits. Our moments of need for external validation. Does it matter? If it was turned off tomorrow would it really matter? Did it ever matter? 

It is hard to become a new version of yourself. The obstacles that stand in the way are all relative. The choice is yours though. The choice is mine. To overcome, we must choose. I am choosing the adventure. The adventure of overcoming my obstacles. You? 

Friday, May 3, 2019

The Courage to Say It

Clay cup of courage 
Inspiration wearing thin 
The end of the week

I am worn out. That shouldn't be hard to admit though, right? Why is it? It's Friday. It was a long week. I worked hard. I did good work. Some of the best work of my career I think. I should be feeling a little spent. I should feel like I left it on the field. That's okay, right? As long as I worked hard, gave 100% it's okay to feel worn out, right?

But still. Admitting I am worn out feels like defeat. It's only Friday. Not just that, it's Friday morning. What does it mean that I am "worn out"? Does it mean I am getting old? Does it mean I am a part of the problem with kids today? Does it mean I can't keep up? Why am I worn out? My Dad worked for 40 years, in the same spot, doing the same thing. Many of those years he worked 6 days a week to provide for us. How can I be worn out not even halfway through my career? a wonderful constantly evolving career, and worn out on a Friday morning? What's wrong with me!? 

I have had this conversation with myself more than once. I  suspect many others go through a similar battle with themselves. I suspect many coffee cups endure the long hard introspective stares of people wrestling with the day ahead, even when it's Friday. Even when the glassy stare is coming from someone who has achieved amazing things during the week, or achieved amazing things in their career or done more than their 40 or loaded more than 15 tons. 

It shouldn't be so hard to admit that when we are worn out. It should be a positive sign of self-awareness. It should be a healthy sign of managing yourself and your emotions. But, for me, it's not. It's hard to admit. Its always hard to admit I am worn out. It's another long conversation with a coffee cup. 

If you find yourself having the same conversation, you are not alone. 

Thursday, May 2, 2019

Defining Moments in Leadership

Sharing honestly

Spring growth and transformation 
Defining moments

I believe leadership is defined in the small decisions and interactions we have as much as the big and highly visible ones. When many people think of strong leaders they often picture the individuals at the top of the org chart who share the big strategic announcements, make the key executive hires or drive M&A activity. Leadership stuff. Real leadership though isn't all big moments. It's not all top of the org chart.

The best leaders I have worked with made the small one-on-one moments feel just as important as the big public leadership events. They took the time to listen - really listen - and engage in the conversation with as much focus and attention as they would a board meeting. The best leaders shared feedback honestly, candidly. No bullshit. No tiptoeing around the corners to avoid confronting the hard facts. Simple honesty. "Here is what you can do better" or "here is what you need to do to get what you want from your career."

We all want that honesty. It is lacking so much today that we are desperate for it. It sucks to hear critical feedback. It just does. No one likes it at the moment. But we all want it. We all need it. The best leaders share it and ultimately we are all better for it. Leaders, real leaders - not just the top of the org chart individuals - take those small interactions, those small opportunities for honesty and growth, and make them defining moments.  

Wednesday, May 1, 2019

Reflections on Growth

From passing showers 

Brief moments to remember 

Reflections on growth

Yesterday it rained in Park City. It rained and then snowed and then rained some more. This morning I walked the dogs in the leftover slush. It is that beautiful time of year in the mountains when everything is growing and the air is fresh and clean with spring. It is also that frustrating time of year when the trails almost dry out enough to get the mountain bike out and then it rains and snows and everything turns to mud again. From hour to hour, and day to day things change.

I have been reflecting a lot on professional growth, both my own and the growth of some of the remarkable individuals I have had the opportunity to work mentor over the years. Professional growth can feel a lot like spring weather. One day, your professional life can be sunny and bright with clearly defined development goals, strong mentors and an ambitious but achievable career plan. It's sunny and bright.

Later that same day, things change. It clouds up and starts raining. Maybe someone moves your cheese or your mentor leaves or that once achievable career plan starts to look more like a muddy trail to nowhere. It's wet and dark.

With all of the wonderful spring growth around Park City, I am reminded that it is not despite the weather but because of it that growth occurs. In our professional lives, it is not despite the challenges of shifting career plans that our growth occurs but because of it. Someone moves our cheese so we find new cheese - better cheese, we lose a mentor but find new ones with fresh perspectives and advice, our career plan turns out to be all wet but we find a new path and a path that is ready to ride. From day to day, hour to hour things change and that is where we grow.

Sometimes, after it been raining we just need to pause and reflect and remind ourselves of the growth to come.

Today, it's sunny.