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A smart 5-step guide to solid decision-making

23rd Feb 2021 | 10:00am

Before I was a CEO, I made decisions faster. Now that I have the final call on many critical decisions that will affect my entire company and its future, I spend much more of my time pondering them and thinking about their downstream effects. 

I’m often asked about my decision-making process—the backstory behind what goes into every choice, large and small, that I make at Okta. Here’s a look into my tried and true five-step process that helps me delegate, think through, and reevaluate the most important ones.

Identify which decisions to pass off

My role as a CEO comes down to five or six critical decisions I have to get right each year and how I operate around them. But hundreds of other smaller decisions arrive on my desk each day that have to be thought through, which means I need to delegate efficiently to other team members. 

I like to classify decisions into two distinct tracks: quick choices and bigger, strategic ones. Jeff Bezos talks about categorizing decisions based on what’s “irreversible.” That’s tough to do; how can you predict irreversibility? I’d position it more as longer-term implications; you can reverse practically every decision, it just might take a while. Knowing which have longer-term implications can help you categorize them, determine who should own them, and decide how much time and research you need to put in yourself.

Seek perspective

I gather many opinions, and not always from the same people—who I go to depends on the decision. I’ve often found people shy away from disagreeing with the CEO, so I actively seek out opinions and opposing views. The only way I’ll get them is if I’m thoughtful in how I ask. I never want to lead the witness, so I try to stay balanced in how I pose the questions to welcome different perspectives. 

When we began the ScaleFT acquisition deal, I didn’t initially understand how valuable the company and its products could be for our business. I asked for perspective from my team, presenting the questions in an unbiased way. A few teammates pointed out how we could integrate to offer automated server access, and that’s when the deal shifted from interesting to must-have. Server access wasn’t the original reason we were interested in ScaleFT, but bringing in other viewpoints helped me see things differently. 

Play devil’s advocate

You should also play devil’s advocate with yourself—it’s difficult, but possible: you have to be good at holding opposing views in your head. Think logically, start internal arguments, and weigh pros and cons before making the leap. I also ask myself how I think people will receive the outcome, and I question the decision more if I think most people will agree with it.

When we decided to bring on a new Chief Security Officer last year, we struggled to find the right candidate. I thought about changing the role and having the CSO report lower in the organization, but when I stepped back and questioned that instinct, I realized it was the easy way out. We decided to stick out the search a bit longer, and we ended up finding the perfect candidate — but it wouldn’t have happened if I hadn’t played devil’s advocate and pushed myself to continue the hunt. 

Take alternate scenarios into account

Before I make any decision, I like to scenario-plan and think through potential consequences to understand what could lead to a wrong decision. This helps me weigh all potential outcomes and usually gives me more confidence in my final call. 

This strategy came into play a couple of years ago when discussing hiring strategies. Our head of workplace proposed a hybrid work model called Dynamic Work that would allow people to work wherever they want, and I thought it was too drastic at first. But as I learned more about the execution and considered the risk of the alternatives—an inability to hire due to location-based restrictions and fierce hiring competition in major tech hubs—I knew it was the right call and would enable us to find the best talent. Collaborate with your team to understand the pros and cons of every decision, and the best choice for your company will become clear.  

Be objective 

Finally, once you make a decision, stay objective in evaluating the result. Go back to your original goals and anticipated outcomes. Did you achieve them, and did stakeholders react as you expected? Then, be honest about whether your decision caused the outcome or if market tailwinds were just on your side.

And don’t expect to get it right at first. Learning the path to solid decision-making takes practice, and it requires patience in carving out the time needed—especially when you’re new to the role and used to making fast decisions with little input from others. I’m 12 years in leading Okta and still discovering new things about the process every day, but this framework has allowed me to successfully make some of the more critical decisions at the company so far.