How to work with a cautious vs risk-taker

Cautious vs. Risk-Taking Personality Traits

Your team at work is made up of cautious people, risk-takers ... and those who are everywhere in between. Understanding your employees’ tolerance for risk can help you manage more effectively (and make smarter hires).

In general, people tend towards one of two extremes: cautious personalities or being a risk-taker. Let’s explore how these traits play out at work.

What does it mean to have a cautious personality at work?

Someone who is cautious in the workplace tends to stick with proven, time-tested solutions. It’s not that they never take risks, but they tend to be more skeptical of doing so. Cautious personality types prefer having time to weigh the evidence, do research, and give a change plenty of consideration before taking the plunge.

What are the characteristics of someone with a cautious personality?

Here are a few cautious personality traits that can show up in the workplace:

  • They tend to default to what they already know works, unless there’s a compelling reason to change.
  • They may be wary of new, unproven processes and tools.
  • They look before they leap. (If someone else leaps first, all the better.)
  • In the extreme, they may miss out on opportunities for growth in favor of the status quo.

How to work with a cautious person

Cautious personality types can be big assets on your team, especially if they’re handling important or sensitive tasks. Let’s dive deep into how the cautious personality trait plays out at work.

How to train a cautious employee
  • If you’re introducing a new way of doing things, offer evidence that it works whenever you can. Don’t look to your cautious employees to be “early adopters.”
  • Give cautious employees space to voice their concerns about new processes, especially one-on-one with you.
How to motivate someone who is cautious in the workplace
  • Make sure that the concerns of cautious employees don’t get steamrolled by the enthusiasm of risk-taker personalities. This give-and-take is not only important to making sure everyone feels heard, but also for making the best possible decisions.
  • Don’t rush cautious people into big risks. If there’s time to slow down and investigate other options, leave room for that.
  • If someone on your team who has a cautious personality takes a risk, make sure you support that risk! Recognize risks that turn out well, and support the employee when they don’t, too… especially if you want to see the employee take more risks in the future.

How to give feedback to a cautious person

  • In your one-on-one meetings, regularly check in about any areas where your cautious employees might need to make a change to get better results.
  • Cautious personalities can sometimes stick with the status quo for too long (especially if they are also change-averse; read the other character trait descriptions for a fuller picture). Look for instances when you might need to suggest mixing things up.

What is the opposite of being cautious?

What about the other members of your team? If they don’t fit the description above, they may lean towards being risk-takers in business settings: people who are much more willing to go out on a limb if it makes sense to them.

What is a risk-taker?

In the workplace, someone with risk-taking personality traits doesn’t need the same level of proof or time to think things through that a more cautious employee would. Risk-taker personalities accept new ideas more easily and are ready to act.

What are the characteristics of risk-takers at work?

You might notice some or all of these traits in the risk-takers on your team:

  • They have a sense of adventure and want to try new things. (Many risk-takers also like change; read all of the character trait descriptions to learn more about how different traits interact.)
  • Once they decide what they’d like to do, they’re impatient to get started.
  • They make decisions relatively quickly after considering the most important criteria.
  • They’re comfortable making executive decisions on the spot, without consulting others, when the need arises.
  • They’re more accepting of failure and moving on when something isn’t working.
  • In the extreme, they may have an “ask forgiveness, not permission” mindset that can land them in trouble.

How to work with a risk-taking personality

Knowing the right way to work with a risk-taker can make a huge difference on your team. When risk-takers feel supported and have the right expectations for communication, they’re much more likely to succeed — and that can lead to big wins for everyone.

How to train a risk-taker
  • Risk-takers sometimes feel they have “enough” information to act on sooner than more cautious employees. In training, make sure they aren’t tuning out important details.
  • Role-play can be a great learning tool for risk-takers. Engage them in training by asking, “Knowing what you know right now, what would you do?” Then, follow up on that by walking through what would happen if they made that choice. This is a great tool for coaching the employee on both skills and good judgment within the role.
How to motivate a risk-taker in the workplace
  • Let your risk-takers… take risks! Risk-takers are unhappy when they feel stymied and unable to try out new ideas. They thrive with some freedom of discretion. Of course, you may not be able to green-light everything, but look for areas where you can offer greater freedom for the risk-taker to use their own discretion.
  • If you’re looking to pilot a new tool or process, let your risk-takers try it out first. They tend to thrive as “early adopters,” especially if they also like change.
How to give feedback to a risk-taker
  • Look beyond the end result. Sometimes risks pay off… and sometimes they don’t. Give feedback on the process and whether or not the risk was a good one. Would running it past another person have helped? Was this the best decision at the time, even though it didn’t pan out?
  • Remember that you have your own place on the scale between being cautious and taking risks, too – and so does your overall company culture. Maybe you’re naturally cautious and need to avoid worrying too much about your risk-taker’s decisions, especially if they have a track record of making good choices. Or maybe you’re in a very conservative work environment and the risk-taker on your team is going rogue in a way that doesn’t fit the culture. Keep these factors in mind as you communicate.

What’s better in the workplace: cautious vs. risk-taking personality traits?

Many business experts advocate a “no risk, no reward” mentality. There are plenty of articles coaching employees to take more risks in order to advance at work. But this ignores the fact that there are plenty of roles where a cautious personality may be better suited for the job. On your legal team, for instance, you probably want people who are going to thoroughly investigate any kind of risk instead of jumping ahead; the same is true with anyone dealing with safety.

But of course, there are also many roles in which risk-taking personalities will naturally thrive. And risks come with all kinds of jobs: Think of the customer service representative who makes a snap decision to best help the customer, the graphic designer who submits a daring new design the client will either love or hate, or the CEO who makes a risky business acquisition.

In the end, most workplaces need a balance of these personality types to encourage growth and make solid decisions together.

Want to learn more about your employees’ work styles — and get insight into applicants?

Hire Success delivers insight on personality traits including being cautious vs. being a risk-taker, as well as tons of other personality traits and the four personality types (A, B, C, and D). We help you hire smarter and manage your team better.

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