Two Words That Make You a Better Founder

A simple approach to succeeding where others burn out

What’s the difference between a great founder and a mediocre one?

More and more, I’m convinced it’s an uncanny ability to focus on possibilities rather than problems. Put another way: It’s having the confidence that you can transform the hundreds of issues you’ll encounter every day into successes. And, of course, cultivating that mindset throughout your team.

Thankfully, as someone not born with this crucial skill, I’ve learned first-hand that you can actively develop it.

And it all boils down to just two words.

When you only see problems, you burn out.

Early in my career, I was an operations manager for a large convention center. Responsible for managing hundreds of people, I was constantly focusing my attention on what needed to be fixed — what wasn’t working. I wasn’t sleeping because my mind was filled with issues, which only made things worse. I was laser-focused on fixing problems through ever-longer to-do lists, but things only got worse.

Eventually, I got so stressed out that I screwed up big time. I miscommunicated the start times for a massive event, resulting in keynote speakers arriving late to their own talks — and angering the hundreds of audience members who were waiting for them.

One day, a guy named Joe pulled me aside. My most trusted mentor, Joe was a senior colleague and friend I had known for years, and he was distressed by my behavior.

“Don’t you see that by worrying so much about what’s not working,” Joe said, “you’re making it so that nothing’s working?”

“Not really,” I said.

How on Earth was I supposed to make things work if I couldn’t fix what wasn’t?

And that’s when Joe made a totally unexpected suggestion:

“Why don’t you take a class in improvisational acting?”

I had never heard of improv, and had never taken an acting class of any kind. But Joe said improv could teach me how to better handle the incessant flow of problems and decisions I was facing, so I signed up for the beginner class.

Two words that changed my approach to management, entrepreneurship, and leadership

Over the next six months, I learned more than I could ever have imagined about how to be a better manager and, eventually, a better founder. But one lesson in particular — neatly summed up in just two words — was, for me, the real eye-opener.

On the first day of the class, our teacher, John, asked me to get up on stage with a classmate — a tall, bald man wearing jeans and a t-shirt. He then assigned us to act out a scene, with one catch:

“Start every line you say, after the first one,” John directed, “with these two words:”

Yes, and…

Those two words, John said, expressed the core of improv philosophy. No matter what the situation, no matter what your scene partner said, your job was to follow suit. To go with the flow.

“Here, today, you can do no wrong,” John asserted. “Assume that whatever happens is supposed to happen. Don’t worry about where the story is taking you.”

John’s approach mystified me. All I could think about were the myriad ways in which I might mess up the scene. Nevertheless, I gave it a go. My partner spoke first.

“Let’s go to the movies,” he said.

I felt the urge, which I would have followed if left to my own devices, to say something like, “Nah, I don’t feel like it.” After all, people want to see conflict, right? But I played by the rules.

“Yes, and…let’s take our dog with us.”

If I had gone with my natural tendencies, the result surely would have been a boring episode about two people who can’t make up their minds. Instead, we brought down the house (our fellow classmates) with a theater scene in which our barking dog angers the other patrons. We tried to quiet the dog with popcorn, which only made things worse — and more hilarious.

OK, it wasn’t going to land us an HBO comedy special, but it was so much fun! I found it so liberating, and wanted more than anything to bring that lightheartedness into the rest of my life.

Which made me wonder:

What if I embraced that same kind of acceptance of, and willingness to work with, the situations I encountered at work?
My improv classmates and I going to the beach in 2006 (That’s me in the passenger seat.)

How “Yes, and….” makes you a better founder

Practicing “Yes, and….” at work was a revelation. My mind opened up beyond immediate problems, and I was more likely to see possibilities. I wasn’t so stressed anymore. Four years later, in 2009, I became an entrepreneur, and I’ve continued to practice “Yes, and.” In my experience, it helps founders in three important ways:

#1. You become a better manager of people

A month ago, a key Worldwide101 employee told me that she had been offered a more senior position at another company. While she insisted she loved working with us, she had made up her mind to leave.

Make no mistake: Not even “Yes, and” made handling this easy. The news hit me so hard that I cried. After everything we had accomplished together, this felt like a giant step backward.

But, thanks to years of practice, I was eventually able to move beyond my immediate reaction and embrace possibilities. In this instance, I consciously initiated an inner dialogue, as if I were on stage with my improv teammates:

“Sarah has found another job, and she is leaving us. I am devastated”, says one voice.
“Yes and…she will be so much happier, and that’s important, don’t you think?” says another.
“Yes, and…she has had such a great impact on our company. I don’t think we can say it’s a step backwards. We are better now than when she started.” says yet a third voice.

And then back to me.

“Yes and…maybe it will pave the way for something even better.”

A couple of weeks after giving her notice, Sarah came forth to recommend her friend Erin to fill her position. Not only is Erin an amazing fit — with all the prerequisite skills — but when she first heard that Sarah worked at Worldwide101, she was so envious she told Sarah that working for Worldwide101 was her “dream job.” Also, because Erin has a personal relationship with Sarah, the transition has been absolutely seamless, with Sarah taking care of Erin’s onboarding and training.

#2. You get better at handling uncertainty

When we first launched Worldwide101’s virtual assistant service, we didn’t have a super-clear sense of our target customer. We got requests from demanding founders and executives who wanted VAs to play an important role in their businesses, but we also had customers who wanted VAs for only the most menial tasks. Before, I would have stressed a lot about that. Instead, I was able to accept the uncertainty, confident we’d figure it out.

Sure enough, one day I got a rude phone call from a customer who had been threatening her virtual assistant for weeks, and I realized that this person had done us a huge favor. After that, we focused our resources on where things were going well, which was with clients who valued premium VAs. We even created criteria and processes to define not only who our service was for, but who it wasn’t for.

#3. You inspire others to similarly focus on possibilities

Practicing “Yes, and…” is a regular topic at our management team meetings. I’m sure I sound like a broken record, but anytime a problem arises or someone complains, I literally begin my response with those two words.

The result is a team that has a higher appetite for risk, face challenges more bravely, finds solutions we hadn’t thought of, attracts better talent, and has helped us grow into the number-one service for premium virtual assistants in the world.

The never-ending struggle against “Yes, but…”

Of course, we’re all human, and nothing is black and white. I still work with hundreds of people every day, and there are moments when I find myself absorbed in problems. There are days when I can’t help myself from essentially saying “Yes, but…”

Still, by practicing “Yes, and,” I can avoid having those feelings become an all-consuming affair of sleepless nights and inner torture. Instead, I’m able to remain open to the idea, as unlikely as it may seem in the moment, that what looks like moving backwards might actually be a step in the right direction.


Sandra Lewis is the founder of Worldwide101, a premium virtual assistant company connecting demanding founders and executives with highly skilled, meticulously matched help.
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