Dear Sage,
I am finding myself having to say “no” to my team lately.
No, that won’t work.
No, we can’t afford that.
No, that’s not something we should do.
I feel like I have to be realistic - but lately it feels like I’m shutting down people unintentionally. I don’t want to be a stick in the mud. Yet how am I supposed to encourage new ideas when I’m feeling responsible for the results - and being responsible feels like I have to be the one to say “no”?
— Well-Intentioned Gatekeeper
Dear Well-Intentioned Gatekeeper,
Most leaders are trained to manage risk, protect resources, and keep things steady. That matters—and it can also become a trap.
When every idea gets filtered through what might go wrong, we start protecting the team from possibility as much as from failure.
I used to be stuck in this trap all the time. And then two moments shifted how I lead.
Shift from “We Can’t” to “How Might We”
The first came during a session with my friend and colleague Caitlin Walker. I was sharing my perspective on an idea when she stopped me and said, “I know what you’re trying to do—and from now on, I want you to start with ‘Up to now …’.”
It was nearly magic. I could share concerns without squashing the energy of new ideas.
The second came when I heard Cy Wakeman speak about Thinking Inside the Box. She described how leaders can define the “undesirable realities” - those unchangeable constraints of budget, timing, and capacity - right up front, then ask their team, “How might we accomplish the goal within this box?”
Those two lessons changed my defaults. Now, I work to name what’s truly fixed and separate it from assumptions or habits. When I outline the actual box we’re working within, creativity shows up. And when I start feedback with “Up to now…,” people hear partnership instead of judgment.
My team doesn’t need fewer constraints - they need clearer ones.
What You Can Try
Pause before saying no. Ask yourself, What am I protecting? Sometimes it’s the organization. Sometimes it’s comfort or control.
Name real constraints. Be clear about what’s non-negotiable and what might just be habit. Clarity creates freedom.
Try “Up to now …” When sharing experience, frame it as what has happened - not what always will. It leaves space for something new to emerge.
Use “How might we …” questions. These shift the conversation from judgment to exploration.
Revisit old stories. “We’ve never succeeded at that” isn’t evidence—it’s a narrative. Ask, What’s different now?
Turning Caution into Possibility
Caution has its place - it keeps people safe and work grounded. The challenge is when it quietly becomes the default. Over time, each “no” can condition a team to stop imagining.
The best leaders don’t throw caution away; they put it in perspective. They name the real limits, open the door to creativity inside them, and model curiosity even when the path isn’t clear.
That’s how teams rediscover energy and progress - inside the box, not outside it.
If you’re ready to bring that kind of energy back to your team, let’s have a conversation about how constraint can become a catalyst for creativity this year.
