The Betting Game: 7 Signs You're Making the Right Bets …

The deeper I get into my career the more evident it becomes that my professional journey is nothing more than a series of bets I’ve made on people. The same can be said by anyone who has crossed my path along their professional journey. They have made a bet on me and my company, and it is my responsibility to make sure that bet pays off for them in the end.   

It’s important to understand the betting culture as you continue to navigate through your career.

Employees bet on companies to advance their careers, companies bet on employees to advance their businesses, customers bet on providers to fulfill their service demands. The crazy workforce you are navigating through is nothing more than an ecosystem of bets that we are all making on each other.

This is not the emotionless, platonic and transactional philosophy it might appear to be. Smart bets on the right people and the right companies will bring a harmony like you’ve never felt before in your career, so keep your money on the winner when you’ve made a winning bet. When you’ve made a losing bet, it’s time to move on. Here are seven signs you’re on the winning side of the workforce “betting game.”

1. Watch how your managers handle defining moments.

Let’s face it. You spend more time with the people you work with than with your friends and family. You go through a lot with your peers in the workforce. Inevitably you will be exposed to what I refer to as ‘defining moments’ alongside your managers throughout the year.

These are the moments, usually a few times per year, that define special leadership from average leadership. Ironically, these ‘defining moments’ tend to be personal dealings. How did your manager handle things when you were dealing with a personal situation? Think back to when you faced personal adversity and ask yourself how the people at work handled those situations? Did it galvanize them to step up and lend support while you were gone? Were they empathetic or did they complain? How your peers handle defining moments is a good barometer of whether or not you’ve made a bet on the right people.

Related: Want to Be a Better Leader? Show Employees You Care.

2. Do you work with smart losers or sore losers?

Full disclosure: I hate losing. You will not find a more motivated and driven competitor than yours truly. However, losing is the most important part of life, and the workforce is certainly no exception.

Over the course of your relationship with peers in the workforce, you’re going to lose together time and time again. Lost customers, botched execution, mishandled strategy. You’re human. These things are going to happen. The important thing is to be smart losers, not sore losers. Reflect back, hold yourself accountable for mistakes and get better for the next time with zero-tolerance for making the same mistakes twice.

Think back to the losing moments. Were your peers smart losers or did they pout over losses? If you’re with smart losers, chances are you’re betting on the right people.

Related: 10 Blessings That Come Hidden in Rejection, Losing and Failure

3. The laugh-cry-think test.

Broadcaster and basketball coach Jim Valvano famously stated that every day of your life you should laugh, cry and think. Look around your office and ask yourself if the people you are surrounded by evoke these emotions out of you. Everywhere I look in my company there are people who crack me up with humor, who inspire me with stories of overcoming challenges, and who challenge me to think in ways that get the best out of me. It’s an incredible feeling when you can say that you surround yourself with people who enrich and fulfill you every day. Take a deep look at the work environment you’re in, and take the “Laugh, Cry, Think” test. If it gets a passing grade then it means you’ve bet on the right environment.

Related: How Good Meals and Goodwill Lead to Good Business

4. The output vs outcome detector.

You need to ask yourself what you are getting out of the company versus what you are putting into it. It’s a difficult question, since everyone has different motivations — money, pride, inspiration, desire for experiences and growth opportunities, the people they work with and for. Most people are motivated by more than one of those.

Think about what you are putting into your company. What are your contributions, your results, your output? Then consider what you are getting out of the company in return for those outputs. If the proportion skews in favor of the company, chances are you are either underperforming or you are in the wrong place. If you’ve bet on the right people and the right company, then you should get from your company what you put into it. If you get more from your company then what you put in, then you’ve made the most winning bet of all-time.

Related: 5 Companies Getting Employee Engagement Right

5. Culture consistency.

Here’s the most challenging part of the betting game: how to detect if the culture is genuine or if it’s nothing more than window dressing.

Every company today proclaims their culture is special and unique. Pets in the office! Yoga rooms! Sleep pods! Every company shouts about their “culture” from the high heavens. My company is no exception to this. However, true culture comes down to three qualities: authenticity, empathy and consistency. Read all about the company you’re thinking of joining, and when you step foot into their office ask yourself if the culture you feel is consistent with what you read about. If the answer is yes, chances are you’re joining a team that is real, genuine and true to their own identity. If your experience in the office is inconsistent with what you read online, then chances are they’re forcing something that is not genuine. This is a good sign that you’re betting on a company that is confused about what culture actually means.

Related: What Switching to Lyft Taught Me About Tech’s Authenticity Problem

6. Prudence or puberty?

When you look at leadership in your company, look at signs to determine if they’re running the company prudently or recklessly. It’s usually difficult to pick up on signs of recklessness when you’re low on the org chart, but as you work your way up it will become more visible.

Look at your company’s track record of layoffs. Why have people been let go? Is it for financial reasons or for performance reasons? The former is a bad sign that speaks to instability and mismanagement. Is your company investing for strategic reasons or vanity? If it’s the latter, watch out.

Think about the long-term vision communicated by senior management. Do you believe in it, or do you think it’s a pipe dream? Stability, longevity and prudence are perhaps the most overlooked qualities in this crazy world we work in. Look at the people above you on the org chart. Do they make decisions with prudent conviction or with reckless abandon? Always bet on the “prudes.” 

Related: 4 Keys to a Stable Business

7. The payoff stage.

Every bet has an expiry. Some are short-term, some are long-term. As the CEO of a services business, I’m partial to the long-term bets. It’s my job to get everyone who has chosen to be on the journey with me to see and feel what the bet will look like when we get to the payoff stage, especially if the payoff stage is a long time away.

Regardless of whether it’s short-term or long-term, ask yourself what the payoff stage looks like; i.e. what does it look like for you when the bet is over? This is a good question to determine if you’ve made a winning bet, and to help determine if the bet you’ve made is a quick payoff or a long payoff. Can you see yourself ringing the bell with your company, or do you bet on your company over the short-run before you move onto the next bet?

Understand the bet, the shelf life of the bet and what you think it looks like at the payoff stage. If there is a smile on your face when you think of the payoff stage then you’ve picked a winner.