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When Empowering Employees to Take Risks, Isn’t Empowering (and Why That Needs to Change)

As a leader, you believe in empowering your team to take risks. But are you also empowering them to manage risk?

A group of people standing on a tightrope, symbolizing risk-taking and the need for balanceA group of people standing on a tightrope, symbolizing risk-taking and the need for balance

Leaders: Optimists by Design

Success in business often requires taking calculated risks. By the nature of their position, people leaders are relatively experienced and successful, traits that often lead to optimism, as Andy Grove famously explained:

In order to build anything great, you have to be an optimist, because by definition you are trying to do something that most people would consider impossible. Optimists most certainly do not listen to leading indicators of bad news.

But what about your team? While you may be comfortable with risk, others might not be as experienced or have the same level of success you do. This lack of experience can make taking risks feel much riskier, especially when tenure and past successes offer a safety net.

Additionally, past failures can make individuals more risk-averse. A team member might hesitate to take a risk if their previous attempts didn’t pan out, even if the current situation is different.

Empowering to Hedge: Not Just Risk-Taking

While encouraging risk-taking is important, empowering your team to hedge risks is equally crucial. Consider our environment in tech (and Andy Grove’s quote above):

  • We all celebrate moving fast” and reward risk-taking.
  • The safest thing anyone can do is advocate for pushing boundaries.

In this environment, suggesting caution can feel like the real risk. This dynamic discourages open communication and limits valuable insights from team members who might have valid concerns.

I think we should slow down”

Anyone who has worked with me, will tell you that I’m not a fan of slowing down. I’m not advocating that you should either. If someone raises concerns about moving too fast or needing more preparation, acknowledge their perspective and inquire. This could reveal valuable insights and potential pitfalls you might have missed.

Empowering Questions

When faced with someone raising concerns, here are some helpful questions you can ask:

What specifically might occur that makes you concerned?

Is that more likely to occur now than it was before?

What activities do you recommend in order to reduce the severity of these risks?

I find that I add value by merely asking these questions. In my own effort to understand, it often brings clarity of thought to the team as well. Ideally you can take this conversation to a place where the team proposes useful solutions behind the concern they’re raising. These might be increased monitoring or better testing, etc. If they don’t have a recommendation beyond slow down” that is also telling.

In the course of discussion usually we can find some ideas to be pragmatic and achievable with a trivial amount of time and effort. As a bonus, the whole situation ends up building trust between us. Remember, you aren’t only pushing for ideas to come from them team because they’re better ideas than ours (although they probably are) we also want the team to be bought into how move forward.

So empower to take risks. Just don’t forget that sometimes the risk they’re taking is speaking up to play it safe”. So empower them to do that too.

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