As a baseball nut, I often use the following leadership gem in workshops and coaching sessions:
"You can't steal second base by keeping your foot on first base."
From personal career development choices to hiring decisions to business strategies, eventually, all leaders have to just “go for it.” Taking risks is a part of business—and life—and forward motion can’t take place until we finally lose contact with first base and make a dash to second.
Smart leaders take the time to carefully assess risks before they take their toes off first base. It’s wise to carefully consider options, look at different angles, and talk to trusted counselors and colleagues before committing to a new direction or opportunity.
But it’s easy for careful risk assessment to turn into “analysis paralysis” or an endless round of inner chatter. Many people wait for others to help them or make decisions for them, or they look for some undeniable signal that gives them permission to take a risk.
The challenge is to learn how to recognize the right time to take that foot off first base. Here are four questions to help you make that final commitment.
1. If I stay where I am, can I eventually realize a similar reward?
Every decision we make is a choice between options. We can choose to get up early to exercise or stay in bed and get an extra hour of sleep. We can choose between the salad or the steak at dinner. At work, we can choose between candidates for an open position or different product lines to develop. In personal development, we have myriad options—classes, books, online training, executive coaching, and more.
It’s easy to list the options that require action, but doing nothing is also an option. The baseball player on first base can choose to stay there until the regular play moves him to second base; sometimes, that’s the right choice. But doing nothing also comes with risk—the risk of missing a market opportunity, losing customers, or becoming stagnant in your career.
Ask yourself—if you stay where you are, will regular play eventually move you to where you want to be? If not, it might be time to take a risk.
2. Can I live with the trade-offs involved in taking this risk?
Because our resources are finite, every decision we make involves a trade-off. If we get up early to exercise, we’re sacrificing extra sleep. If we choose the steak at dinner, we are choosing not to have the salad.
In our careers, we might turn down a job offer that offers a significant increase in pay and responsibility because it would impact family time too much. Or we might put an advanced degree on hold to take advantage of an internship or special project that might not come along again.
What are the trade-offs involved in the opportunity before you? If the risk doesn’t result in the rewards you hope for, can you live with the trade-offs you made in pursuit of that goal?
3. What are the possible outcomes of this risk?
In her book Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts, decision-making expert Annie Duke points out that in every decision we make, “we are betting against all the future versions of ourselves that we are not choosing” (emphasis hers). As she suggests, every choice is a bet that our future selves will be better off by some measurement than if we’d made a different choice.
Think through the possible outcomes of the risks in front of you. Are the possible rewards too big to ignore? Will your future self—and maybe other people’s future selves—be glad you took this risk?
4. In five years, how will I feel if I don’t take this risk? How about ten years?
In the United States and much of the western world, we tend to take great pains to reduce our risks. We wear seatbelts and helmets, get regular medical exams and screenings, and avoid obviously risky environments.
Minimizing risk is, generally speaking, a good practice. People who minimize their risks tend to live longer than people who don’t. In five or ten years, we are likely to be glad we wore seatbelts and got our regular medical screenings.
But in business decisions, there comes a point where leaders need to commit to a decision and go for it. Too many times as I coach older leaders, they admit to me that they regret never trying something that they wish they had. And then it is too late.
Sometimes, it’s time to take your foot off first base and dash for second.
Of course, not all risks produce the results we want. A player who tries to steal second might be tagged out. But only by taking the risk will the player and the team know whether it was worth trying.
As you contemplate decisions in your leadership role or your career, it’s fine to take a cheetah pause and consider all the options, resources, and possible outcomes. But once you’re satisfied that your risk offers a reasonable chance of success, take your foot off first and run for second base!
Self-check:
- Do I get stuck overthinking decisions or reasonable risks?
- What is one risk I regret not taking?
- What is one risk I could take today to advance my career?
