Five questions to help you make better, more confident decisions
Decisions are the currency of leadership.
The higher up you go in your career, the harder those decisions tend to get. And yes, the stakes go up, too.
But here’s the good news. If you want to make sound decisions, you don’t need to have all the answers. You just need to ask the right questions.
As you face big decisions this year, I want to share five important questions I’ve learned to ask before making a big call. Heaven knows I didn’t get them all right over the years (Crystal Pepsi, anyone?), but this process will help you make any decision with more clarity and confidence.
1. Am I the one who really needs to make this call?
As you rise, it’s easy to take on more decisions than you should. But sometimes they’re better left to the people closest to the work.
Hootsuite CEO Irina Novoselsky told me she believes in pushing decisions down whenever possible and trusting the people you’ve hired to make them. It frees up your time and builds a stronger, more capable team, as people feel empowered to own the decision themselves.
So before you do anything else, ask if the decision is really yours to make, or someone else’s to grow from.
2. What are the stakes of this decision?
At Amazon, they use a simple framework to evaluate the type of decision they’re facing and the risks that come with it:
Is it like walking through a one-way door or a two-way door?
CEO Andy Jassy went into detail about this idea when he joined the podcast, explaining that most business decisions are two-way doors: “You can walk through that door, and if you got it wrong, you can walk right back through.” These are decisions you can delegate and move faster on, so you stay agile and ahead of the competition.
On the other hand, one-way door decisions are hard—if not impossible—to undo. These call for more time, more input, and more care.
Decide which kind of door you’re facing. That alone will give you a better sense of how fast to move and how much energy the decision deserves.
3. How well do I understand the reality of this decision?
If you want to make good decisions, you need to start with sound information.
Not what you want to be true, or what you assume is true, or even what you hope will be true.
Southwest Airlines CEO Bob Jordan stressed the importance of intellectual honesty as he and I discussed how he made decisions during the Boeing Max crisis. As he told me, “You’ve got to be clear-headed about what you’re facing, and you’ve got to make decisions based on real data.”
So be honest with yourself about how well you understand what’s going on. Look at the facts. Study the data. Listen to your team and customers.
Remember, a good decision based on bad information isn’t a good decision at all. But if you can define reality, even when it’s ugly, then you put yourself in position to make a decision that actually holds up.
4. Have I invited healthy debate about this?
Richard Fain led Royal Caribbean for 20 years, helping turn it into the global travel powerhouse it is today. And he couldn’t have done it without making some key decisions (like literally cutting a cruise ship in half in order to make it bigger and better).
In my conversation with Richard, one thing was clear. There’s a powerful connection between those kinds of smart decisions and the culture of healthy debate he encouraged. For them, he said, “‘Devil’s advocate’ becomes a nice word. It’s a compliment, not an insult.”
So for any important decision, consider the ways you’ve invited constructive pushback. Have you surrounded yourself with diverse perspectives and given them permission to challenge assumptions? Has your team debated and discussed it from all angles?
That’s the kind of culture that makes every decision stronger and keeps teams aligned.
Knowing you’ve considered every angle helps you avoid mistakes, move forward with confidence, and build a team where everyone feels heard.
5. Am I thinking clearly, or falling into bias?
None of us is perfectly objective. Even experienced leaders fall into patterns of flawed thinking — often without realizing it.
To avoid these traps, start by recognizing you’re not immune to them. Then learn to spot the most common culprits of cognitive bias. Watch for:
Sunk cost fallacy: Sticking with a failing strategy because you’ve already invested a lot into it
Example: You up the budget on an underperforming product because it took two years to build.
Halo effect: Letting someone’s past success influence how you judge their current ideas
Example: You green-light a high-performing exec’s proposal without digging into the details.
Confirmation bias: Ignoring evidence that doesn’t support your view
Example: You leave AI off the quarterly agenda because you’re skeptical of its value.
Recency bias: Giving more weight to the latest data or feedback
Example: You change strategy after one bad sales week, despite a strong quarter overall.
Once you know how to name the bias, it’s much easier to account for it in your thinking and keep it from clouding your judgment.
Final thoughts
Leaders are defined by their decisions. And because of that, it’s easy to romanticize the process or attribute good decision making to brilliance or boldness.
But in my experience, great decision makers have honed that skill through habit, discipline, and the questions they ask themselves throughout the process:
- Am I the one who needs to make this call?
- What are the stakes?
- How well do I understand reality?
- Have I invited healthy debate?
- What biases do I have?
That’s the work. And the more you do it, the more confident — and consistent — your decisions become.
Which of these five questions do you already use? Which one do you want to bring into your next big decision? I’d love to hear what’s worked for you. Drop a comment or tag a leader you admire who makes great decisions under pressure.
Your Next Step
Make the How Leaders Lead app part of your daily leadership routine! It’s 100% free to download and use, no catch.