How to Work With Your Boss on Taking Risks
I received this submission in my Coaching Corner:
"While I like to take risks, my Manager plays it safe thus limiting the exposure of our team. How can one work in an environment where top down the Leadership is risk averse."
My Response:
I hear your frustration, so my advice...
Quit. Yup, quit! Go start your own company. Call your own shots. Take all the risks you want. What do you think?
Does it sound too risky? 💀
So, I wanted to make a point here. There are different levels and categories of risk. There are decisions that are big and mostly unchangeable (Amazon refers to these as one-way door decisions), which are higher risk like building out a new data center or buying a Super Bowl commercial spot. Then, there’s two-way door decisions, which have limited and reversible consequences, and are lower risk like testing new headlines on a landing page.
Can you categorize the risks you want to take at work — are they higher risk (one-way door decisions) or medium/lower risk (two-way door decisions)?
If they’re high risk, well, it’s the equivalent of telling your boss to quit their job. They’re going to have a negative knee-jerk, you’re-out-of-your-mind reaction. If they’re medium to lower risk, then there’s a few things you could do to influence their decision.
⬇️ 1. Lower the risk - Perhaps changing the headline on your homepage, while reversible, is something your boss thinks is high risk (it could be totally wrong and hurt new business acquisition). How could you de-scope this or take a smaller step to show progress, instead of going 100% out of the gate? Could you run smaller tests on other landing pages, do a focus group, run a test on the homepage with a small subset of users, test the messaging on ads? By showing supportive positive data, your boss may see that this isn’t as high risk as they thought and worth the risk to try out.
❌ 2. Call out the risks - Have you ever felt scared? One of the ways you can address your fear is to understand what you’re fearing and doing something about it. Let’s say you want to test out a new free pricing plan. We know the benefits — that it may drive a lot of new user sign ups and make us more competitive. But you’re getting push back from your boss. Walk through all the risks and how you can address them, and what you can’t address. Hopefully the list of unaddressable risks becomes lower than the benefits and your boss gives you the go ahead.
At the end of the day, your leadership is going to need to support your decision. They pay the bills, and your paycheck, after all. Hopefully you can convince them to see that the risks you want to take are worth the rewards that you’ll be able to reap.
And if that doesn’t work, you know what to do. Quit and start your own company. 😉 Or at least go somewhere where they're more likely to take bigger risks.