Diana Kander: Success takes more than a poker face

Diana Kander

Diana Kander likens business to poker. Success means staying curious, covering your blind spots and taking risks. The bestselling author and ICBA LIVE 2020 general session speaker says these are key strategies for innovating, problem-solving and future-proofing your community bank.

By Eric Best


Curious about what it takes to be a successful entrepreneur? Try watching a game of poker.

Just like in business, poker players must eschew temptation and practice self-control to win a hand. Using small bets—or intentional risks in business—players find opportunities to test assumptions, chip away at risk and maximize their chances of success. They pay attention to other players and take note of their behaviors, just like business leaders must understand their customers. Similar to Owen Chase, the protagonist of Diana Kander’s 2014 novel All in Startup, they wait for the right moment to go all in on their big move.

“I think of poker as the ultimate metaphor for entrepreneurship, because you are guaranteed to lose,” says Kander, a general session speaker at this month’s ICBA LIVE 2020 in Orlando, Fla. “You’re going to have stuff not work out. The trick is: Can you figure out the losses before you lose it all? And can you maximize the gains when they’re going well?”

Kander has made a name for herself with two business books that use hypothetical entrepreneurs’ stories to teach real-life skills. While she’s not a star poker player herself, she does write from experience. Now a consultant in the banking industry, Kander has owned and managed businesses ranging from real estate to staffing and software companies. Some have been successful; some haven’t.

In fact, All in Startup was inspired by one of her biggest failures. Kander had started a company and raised plenty of money from angel investors, but it couldn’t stop her and her team from avoiding a troubling revelation: Their solution didn’t actually solve the problem it was meant to remedy. By the time Kander had figured that out, their capital had dried up.

“It blew up really big and then it crashed really hard,” she says. “I started journaling to deal with all the feelings I was going through, and once I had figured out what we had done wrong and how I would do it differently, that journal turned into my first book.” The book became a New York Times bestseller and has been used in entrepreneurship classes at nearly 100 universities around the world.

One lesson Kander took from her entrepreneurial experience: Don’t get an ego. “The trick is, how can you put things in your life to keep you objective about what’s going on and to make each decision like you’re making it from scratch?” she says. “It’s impossible to go through a poker tournament and not lose hands, but the thing that makes a professional is if you can have more money left at the end of the day.”

“It’s impossible to go through a poker tournament and not lose hands, but the thing that makes a professional is if you can have more money left at the end of the day.”

–Diana Kander

Learning how to be an entrepreneur

Kander’s keen sense of what it takes to be an entrepreneur came from watching her parents.

Her mother and father emigrated from the Soviet Union during the Cold War, eventually settling in Kansas City, Mo., where they had family.

“We came to the U.S. as refugees, so they had like $260 and they had no capital, no connections, no English, no education that was recognized in the United States,” Kander says. “They just had limited upward mobility.”

Her mom worked in a lab manufacturing dental crowns. When her dad was injured in a car accident, Kander’s mom would bring books from work home for him to read. The two took that knowledge and turned it into their own dental lab.

When her parents became business owners, Kander caught the itch herself. In school, she’d sell flea market finds to her classmates at a markup. When she got older, she went door to door selling water filters.

“I saw the transformation that [entrepreneurship] had on my family,” she says. “The possibilities are endless, so I was like, ‘I need to start a business immediately.’”

Kander went on to study political science at the University of Missouri–Kansas City and then got a law degree at the Georgetown University Law Center, which she thought would put her on the fast track in the business world. She took a job as an attorney but eventually left to start businesses in a variety of industries. “I spent my 20s trying to gain as much knowledge and skills as possible,” she says.

Close feedback loops

This insatiable curiosity is at the core of Kander’s message to budding entrepreneurs and business leaders across industries. In her 2018 book The Curiosity Muscle, cowritten with entrepreneur Andy Fromm, she advises leaders to make sure they don’t have “feedback loops.”

“It’s like the manager of a restaurant walking by your table being like, ‘Everything great? OK.’ and then just keep walking,” she says. “That’s how a lot of feedback loops are set up. People pride themselves that they have 95% approval scores and everything is going great. That’s just not how you grow or improve.”

If you only listen to positive responses, Kander says, then it’s like going to the gym to lift one-pound weights. Staying curious builds strength and stamina.

Often, she says, it’s an organization’s culture that stifles employees and stakeholders from being curious about ways to make things better. She points to findings from Google’s Project Aristotle—the tech giant’s 2012 initiative on team effectiveness—that said the most important thing to making a team work is psychological safety. That means people shouldn’t feel they’ll be punished if they speak up.

“I ask people in large rooms to raise their hand if they’re working on something that they don’t necessarily believe … is going to work, and a lot—I mean most of the room—will raise their hand. They don’t raise them high, because their managers are in the room, but they let me see their fingers,” Kander says. “It’s a problem, because nobody ever got fired for being quiet.”

To help people stay curious and grow risk tolerance in your organization, Kander says to take baby steps. For example, instead of asking for feedback on the company generally, start by allowing your team to critique a project or initiative that went well.

“Before they can criticize something that didn’t work out or really speak up in times of danger,” she says, “they’ll [want to] test it a little bit at a time [and] see how the group or their boss reacts.”

Ultimately, Kander says it’s emotion that can get entrepreneurs into trouble. Poker players avoid tilt, where a short run of a few bad hands can lead to an entire game going downhill. Staying objective, curious and open to constructive feedback can take the emotion out of your or your community bank’s next decision.

“Either your ego is too much invested in what’s going on … or you’re so stressed about things going poorly that you just can’t make good decisions,” she says. “It’s just easy to get emotionally wrapped up into what’s going on.”

It turns out that a lot of work goes into a poker face—but it can really pay off.

4 ways to stay curious

Diana Kander, author of The Curiosity Muscle and All in Startup, says these tips will help you make better decisions and drive results:

  1. Know your blind spots. In other words, what don’t you know? Each bit of information or additional insight will propel you in new directions. “As soon as you stop being self-aware and stop trying to uncover your blind spots,” Kander says, “I believe you will start to plateau and get stuck wherever you are.”
  2. Establish priorities. Once you have new momentum, decide what will bring you the most value. Kander uses the example of a huge beverage brand, which studied its product lines and found that many were “zombie products,” meaning they weren’t driving the bottom line. “Shut down things that aren’t working,” she says. “It’s easy to say no to bad ideas, things that are obviously not working. It’s hard to say no to things that are not good enough.”
  3. Measure the right things. Is your new direction or solution the correct one? Is there an objective way to tell it’s working? Sometimes, Kander says, we ignore data because we’re afraid of what it will tell us. “We like to protect our ego. Our natural inclination is to be comfortable and safe,” she adds.
  4. Involve others to get what you want. Are your goals siloed to just you or another manager? Sharing your goals with someone can keep you accountable and boost your chance of success.

Eric Best is deputy editor of Independent Banker.

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