Four Questions Every Leader Should Be Asking — Starting With Themselves

We talk a lot about psychological safety, employee well-being, and building cultures where people feel supported. But before leaders can create that kind of environment for their teams, they need to be able to do it for themselves. When leaders are disconnected from their own emotional state, it shows up in how they communicate, how they make decisions, and how their teams feel walking out of a meeting. Culture doesn't get announced, it gets absorbed. And that starts with self-awareness.

The research on emotional intelligence backs this up. Six Seconds, a global organization dedicated to the science and practice of emotional intelligence, has spent decades studying how emotional literacy, the ability to identify and name what you're feeling, is foundational to effective leadership. Their work, grounded in Plutchik's Wheel of Emotions and the Six Seconds Model of Emotional Intelligence, shows that leaders who can recognize and navigate their own emotions make better decisions and build stronger, more trust-based teams.

Here are four simple questions that can help nonprofit leaders check in with themselves, and model the kind of reflective culture that actually sticks.

1. What am I feeling?

Most of us skip this step entirely. We move fast, stay busy, and push through, and somewhere along the way, we lose track of what's actually going on underneath.

Name it: stressed, stretched thin, energized, uncertain. You don't need the perfect word, just an honest one. Getting it out of your head and into language is the first step toward understanding it.

Six Seconds calls this emotional literacy, and their research shows that people who can describe emotional experiences in greater detail have stronger emotion regulation overall. One of Six Seconds CEO Josh Freedman's favorite coaching questions is deceptively simple: What else are you feeling? Because emotions rarely travel alone. That first label, "I'm stressed," is almost never the whole story. There's usually something underneath: maybe it's fear about funding, pride tangled up with exhaustion, or grief sitting alongside purpose.

And here's why this matters beyond you: when nonprofit leaders normalize naming emotions, even casually, even briefly, it gives everyone else permission to do the same. That's how psychological safety gets built, one small moment at a time.

2. What options do I have?

When we're in the thick of a hard situation, it's easy to feel stuck. Like there's only one path forward, or no path at all. But that feeling is rarely accurate; it's usually a sign we need to zoom out.

This question is a pattern interruption. It invites you to shift from reactive to intentional. Even identifying two or three small choices, who to loop in, what to let go of, what to ask for, can open things back up. The trick is to not shut yourself down while brainstorming – let creativity take the wheel, even if it’s just for 10 minutes. Then, consider how each option plays out.

For nonprofit leaders especially, this is a powerful habit to bring into team conversations. When a program director comes to you overwhelmed by a funder deadline and a staffing gap at the same time, helping them map their options is often more valuable than handing them an answer.

3. What do I really want?

Not what you think you should want. Not what looks good in a grant report. What do you actually want, for your team, for the mission, for yourself?

It's worth pausing on because the answer is not always obvious. Sometimes what we think we want (to fix the problem quickly) and what we really want (for our team to feel trusted and capable) are pointing in different directions. When you know what you're actually after, you make better decisions and communicate with a lot more clarity.

Try bringing this into goal-setting and one-on-ones. "What do you really want here?" can unlock a level of honesty that changes the whole dynamic, especially in mission-driven organizations where people tend to put the cause ahead of their own needs until they burn out.

4. What do I need?

Start this one at the team level: what does this group need right now? Not just in terms of resources or process, but in terms of support, recognition, or breathing room. The answers might surprise you.

Then turn it inward. For many nonprofit leaders, especially those running lean teams and wearing multiple hats, their own needs go unspoken (even to yourself). A break. A clearer boundary. More support from the board. Space to think before responding. Whatever it is, naming it is the first step to meeting it.

From Question to Habit

These four questions aren't a fix-all. But they are a foundation for self-awareness, for more honest conversations, and for the kind of leadership that makes people feel genuinely supported.

Start small: run through them yourself before a board meeting or a tough conversation, or introduce one in your next team check-in. Building a culture of well-being doesn't always start with a new policy or a wellness stipend. Sometimes it starts with a leader who's willing to ask themselves a hard question, and actually sit with the answer.