Software Leadership: What poker taught me about work

There are many lessons and many levels to something like the game of poker, most of which you can directly apply to your IT job.

Ryan Haveson

Several years ago, a friend of mine asked me to come to a poker game at his house. I had never played poker before. With my nonexistent poker skills, I figured not only would I end up leaving without any cash, I wouldn’t even last to the end of the night.

Fortunately, I had a couple of weeks before the game. I went to the bookstore and bought every book I could find on poker. For the days leading up to the game, I read extensively about poker, watched poker on TV and even played practice poker online. By the time game night came, I felt ready.

The prep work really paid off. I was able to hold my own and even leave at the end of the night with some winnings. Most people aren’t all that great at poker, so the prep work gave me an advantage. If I hadn’t spent the time learning about the game and practicing beforehand, I’m confident I would’ve left with nothing.

I certainly didn’t master the game in two weeks, but with a good bit of prep work I was able to hold my own. Now after a few years, I look back and realize how many important lessons poker had taught me as it applies to work and life in general.

Poker work-life skill No. 1: Be prepared, it pays off

Poker is a fascinating game because it forces you to make decisions on a minute-by-minute basis. I continued playing poker for several years. I rounded out my book knowledge with more hands-on experience. In most aspects of life, it’s hard to objectively measure the success or failure of any given decision. In poker, it’s very clear every few minutes at the end of the hand or the end of the night whether you won or lost.

Some decisions require complex statistical calculations, or interpreting subtle behavioral queues from your opponents to decipher if they’re bluffing. Other decisions are surprisingly easy. This is a similar dynamic to life as an IT professional. For example, the best starting hand in poker is two aces. When dealt pocket aces, you have a significant statistical advantage to winning the hand. In this situation, during the opening betting round your goal is to get as many people to bet into the pot as possible.

If someone before you makes a big raise, you have a pretty good shot at coming out of the hand with a nice payoff. They most likely think they have a good hand. Remember, a pair of aces is the best starting hand possible. Besides the unlikely scenario where someone else also has the other pair, you’re in a good position to win.

Imagine someone agreeing to give you $10 for every $1 bet you make on a coin toss. You take this bet any day, any time. However, poker has an element of chance. Nothing is ever guaranteed. The first time you draw someone into a pot where you have a clear advantage and then they catch a lucky card in the end to win a big pot, you learn the next lesson.

Poker work-life skill No. 2: You can do everything right and still lose

The corollary to this is that your opponent can make a big mistake and still win. Over time, the right decisions usually lead to the right outcomes. As in life, though, there’s an element of chance in everything we do. Many people shy away from making big decisions because they can’t be guaranteed a result. That’s a flawed way of thinking. As the saying goes, “nothing ventured, nothing gained.”  

In poker, as in life and work, the more decisions you make, the better you become at assessing risk and weighing the trade-offs. Throughout the game, I became more comfortable taking risks. Risk taking is like exercising a muscle. The more you practice, the better you get. Because the results aren’t completely within your control, it’s important to remember a side effect of this rule: You should never risk something you’re not willing to lose.

On one occasion, I bet all of my money early in the night on a hand that was almost guaranteed to win (there was a greater than 90 percent chance). I lost when someone stupidly took the bet then caught a lucky card. I had to spend the rest of the night watching from the sidelines, because I had lost all my cash.

Poker work-life skill No. 3: Don’t risk something you’re not willing to lose

Poker has many layers, much like the work environment. The first layer of risk/reward assessment and statistical analysis for decision making is relatively straightforward. That’s only one part of the game, though.

The first word that comes up when people think of poker is “bluffing.” This is the art of throwing off your opponents so they don’t know the strength of your cards. It turns out that bluffing is actually a two-step process.  

The first part is to determine the result you want to achieve. For example, if you have a strong hand, you want to have more players stay in the hand and bet into the pot. On the other hand, if you get a bad card, your goal should be to get everyone else in the hand to fold.

The second part is deciding how to modify your behavior to achieve the result. If you have a great hand, the natural behavior would be to do a fist pump and grin. You know you’re in a superior position. Of course, this would result in everyone bowing out of the hand, so your winnings would be much less.

Poker work-life skill No. 4: Separate the desired result from the behavior needed to achieve it

This two-step separation isn’t natural. It is, however, one of the most important things I’ve learned from poker as it applies to work. How many times have you been in a situation at the office where you have a great idea, one that will really set up the team up for success, but the person you need to convince is either too busy to listen or just doesn’t get it? This can be extremely frustrating.

You must maintain your composure in such situations. Losing your temper or letting your emotions get involved in the discussion can be counterproductive. It can cause the other person to shut down. In these types of confrontations, I think back to the poker table. I remember to separate the result from the behavior I want to use to achieve that result.

You should also remember that any change or decision involves risk (remember poker work-life skill No. 2). Even if it’s statistically the right decision, the outcome isn’t guaranteed. This might be the issue your colleague is concerned about, so you should remember that it’s a valid concern.

Poker work-life skill No. 5: Prepare an influence strategy before any high-stakes conversation

In poker, some people are risk-takers and like to bet on anything. Other people are conservative. You’ll meet both types at the poker table and in the office.

The risk-takers are hard to bluff. They’ll be in the hand to the end hoping to draw a card they want. The conservative people have the advantage in that they’re in a better position to bluff. When they bet big, they generally have the cards to back it up so they can scare people out of the pot. Everyone has a different style of making decisions. At work, just as in poker, you have to adjust the way you approach any high-stakes conversation.

Some people are risk-averse. You need to take extra care to address any concerns they have or be extra clear about the risk-mitigation measures you plan to take. Some people just don’t like doing extra work and require a bit more selling on the value proposition of the result.

Remember lesson No. 1 here (be prepared) as it applies to these important conversations and you’ll be in a better position to achieve your desired result. Don’t confuse this strategy with being manipulative. Coercion and manipulation involve misleading someone down a bad path or a path that isn’t in their best interest. Preparing for a conversation so you can help generate the desired outcome is part of helping set your team up for success.

While I don’t play poker that much anymore, the lessons I learned really helped me in the office environment. I strengthened my decision-making muscles, and I became more comfortable with the fact that things won’t always go my way—and learned not to worry too much about that.

I learned to be more of a risk-taker. I also learned that going in with guns blazing isn’t always the best way to achieve great results. So the next time someone invites you to a poker game, don’t be afraid to accept. But first, go to the bookstore and read up on the game. Otherwise, your night will be short and you’ll end up watching from the side.

Ryan Haveson

Ryan Haveson has more than 15 years of experience leading engineering teams and delivering software and services for some of the world’s most recognized brands, including Xbox and Windows. He was a group manager in the Windows Experience team for Windows 8. He and his team designed and delivered end-user and developer-facing features, including the live tile notifications platform and the new Task Manager. He’s currently leading the engineering systems group at Qualcomm Inc. for the Windows/Windows Phone on Snapdragon division in sunny San Diego. Reach him at or at