The Strategic Yes: Why Great Leaders Move Before Every Detail Is Guaranteed
One of my favorite “young Holly” stories still makes me laugh.
Toward the end of my time as a student at The King’s College, I was working in the Admissions Office and got tasked with planning a recruiting trip to D.C. And man, did I plan it.
I do not remember the exact schedule all these years later, but I do remember it was two or three days of a jam-packed itinerary, multiple high school visits, and apparently zero margin for food because when I showed it to Luke Smith, who was going to co-pilot the trip with me, he looked at me and said, “Holly, when are we supposed to eat lunch?”
Oops.
He was a trooper and came along for the ride, including the part where I got a ticket for running a red light near the National Mall, which is another classic Holly story for another day.
Fast forward 16-ish years, and I am having flashbacks because of what this week looks like.
A few months ago, Tim Stevens, a client, the founder of LeadingSmart, and also a dear friend, looked at his calendar and said, “I don’t have anything currently scheduled the first week of June. Should I come to Houston for some strategic planning days?”
I immediately said, “Let’s do it.”
And then, naturally, we filled the week to the brim.
He scheduled an onsite with a client doing what he does best
We’re filming our first LeadingSmart Masterclass on one of the topics we get asked to consult on most
We’re carving out a day for strategic planning
We’re hosting a webinar on staffing and structure
We’re facilitating a roundtable gathering of 18 executive leaders
As I was preparing for the week, I realized something important.
The Masterclass, the webinar, and the roundtable were all new ideas Tim said yes to with no guaranteed ROI. No perfect spreadsheet, no fully proven model, no certainty that every detail would work exactly the way we hoped (and, by the way, Tim loves a spreadsheet, making his “yes” even more impressive).
But he said yes anyway because the ideas were aligned with the mission. They would serve leaders. They would help teams. They would teach us something. And they were worth trying.
And it struck me…that is a different kind of yes.
It is not a reactive yes.
It is not a people-pleasing yes.
It is not a scattered yes to every shiny idea that crosses the table.
It is a strategic yes.
And strategic yeses are one of the most important disciplines a leader can learn.
The Best Leaders Do Not Wait for Perfect Certainty
At the executive level, very few decisions come with perfect information.
You usually do not get a guaranteed ROI before you make the hire, launch the initiative, restructure the team, create the product, host the event, or test the idea.
You may get signals, patterns, or convictions, but it’s more likely that you get a sense that this move is aligned with where the organization needs to go next.
And then you have to decide whether you are willing to act before every question has an answer.
That does not mean leaders should be reckless. Reckless leadership ignores reality. Strategic leadership pays attention to reality and still knows when it is time to move.
There is a big difference between saying yes because you are bored and saying yes because the opportunity aligns with the mission.
There is a big difference between saying yes because you cannot say no and saying yes because the work matters.
There is a big difference between chasing every idea and testing the right ones.
This is why the last (but not least!) stage of The READY Framework is called the Yes Barometer, because it’scritical to organizational growth that leaders understand what deserves a yes.
Innovation Requires Experiments
Most organizations say they want innovation, but what they really want is guaranteed success with no mess. Unfortunately, that is not how meaningful ideas grow.
The first version of almost anything is an experiment.
The first webinar teaches you what your audience actually cares about.
The first masterclass shows you what people are willing to pay for.
The first gathering reveals which conversations leaders are hungry to have in the room.
The first version of anything gives you information you cannot get from a planning meeting.
This is where many executive teams get stuck. They analyze for too long, hoping the risk will eventually disappear.
But the risk rarely disappears. It just changes shape.
At some point, a leader has to decide, “This is aligned enough to try.”
Not perfect.
Not guaranteed.
Not completely figured out.
Aligned enough.
That is often where momentum begins.
Mission Creates the Filter
Of course, not every opportunity deserves a yes.
In fact, the more your organization grows, the more important it becomes to say no often. Capacity is not unlimited.
Attention is not unlimited, your team’s energy is not unlimited, but mission gives leaders a filter.
When the mission is clear, you can evaluate opportunities differently.
Will this serve the people we are called to serve?
Will this help us learn something we need to learn?
Will this deepen trust with the right audience?
Will this create momentum toward the future we are building?
Will this stretch us in a healthy and strategic way?
That is why Tim’s yes stood out to me.
He did not say yes because we had every detail figured out. He said yes because the opportunities were connected to the work we already care deeply about: helping leaders and teams get healthier, clearer, and better equipped for what is ahead.
You Need People Who Will Build With You
Tim joked this morning that this week feels like finals week, which is probably what sent me straight back to my over-scheduled recruiting trip itinerary.
And honestly, I am grateful for people who will roll their eyes at my over-scheduled itineraries with a smile and still say yes.
Every leader needs those people…people who can look at a meaningful opportunity and say, “This is worth trying.”
People who:
bring wisdom, experience, humor, and flexibility into the room.
are willing to learn through action, not just theory.
understand that important work often starts before the spreadsheet has all the answers.
The Leadership Question
So maybe the question is not, “Do we have every detail figured out?”
Maybe the better question is, “Is this the right kind of yes?”
Is it aligned with the mission?
Will it serve the right people?
Will it teach us something we need to know?
Does it create momentum toward the future we are trying to build?
Are we saying yes from clarity instead of pressure?
Because life is too short to be bored, and the work is too important not to try.
The best leaders do not say yes to everything.
But when the right opportunity comes along, they know how to say a strategic yes before every detail is guaranteed.