Most leadership writing on initiatives assumes a clean starting point: a leader presents a compelling vision, the team rallies, the work gets done. Start with Why, the books tell us, and everything else falls into place.
But what about when the Why is thin? Or worse, when it’s handed down from somewhere above you, you weren’t part of the conversation, and you can see the challenges but the benefits aren’t clear?
That’s the scenario most leadership advice quietly skips. Let’s talk about it.
When It Works the Way It Should
When an initiative starts well, it usually starts collaboratively. Senior leaders bring the initiative concepts (or ask for suggestions) and the strategic context is discussed. People closer to the work bring the operational reality. There’s enough psychological safety in the room that someone can say “I think there are some challenges…,” and the response is curiosity rather than defensiveness.
That kind of conversation pressure-tests the ideas, and powerful initiatives are born. The Why gets stronger when smart people push on it. When it’s announced, the reasoning has been tested by the same people who’ll actually carry it out and who are not just informed but invested.
When the Why is built that way, teams can get behind hard things. They’ll work long hours. They’ll absorb setbacks. They’ll defend the initiative to skeptics in the hallway. Not because they were told to, but because they helped shape the case and they believe in it.
When “the Why” Doesn’t Hold Up
Sometimes none of that happens. The initiative arrives on your desk, you’re told to lead it, and the rationale feels weak. You attempt to ask questions and the answers are unsatisfying. Possibly the responses are even delivered with impatience and may even signal disappointment by the senior leader in the asker. Maybe the reasons contradict what the team has been told before. Maybe they ignore constraints you’ve been raising for months. Or maybe you can’t see how it can possibly get done with resources needed exceeding those available. It may just feel like someone’s pet project dressed up in strategic language.
This is where leadership gets uncomfortable — and where emotional intelligence earns its keep.
The first question is the hardest, and you have to ask it honestly: Can I support this in good faith? Is this something I am able to get behind?
Not “can I tolerate it.” Not “can I fake enthusiasm for it.” But can I genuinely stand in front of my team and advocate for this work without betraying their trust or my personal integrity?
If the answer is no; if “the Why” isn’t just weak but it violates something foundational for you, you may need to start preparing your exit.
I have come across one instance of this in my life. I determined that the need to follow an initiative required me to compromise my values. Fear told me I had no choice but to comply. But when I came home and looked into the eyes of my young sons, a question popped into my mind, “What would I want them to do?” This clarified things and superseded my fears – the obvious answer was that I would want them to “do the right thing.”
That night I started looking at other opportunities. Within a week I had an interview and eventually got a job at a company whose stated values aligned with mine. Leaving for that opportunity was the best professional decision I ever made.
But there’s a middle path, and it’s where most of us spend much of our time. You disagree with parts of it. You see real problems. Possibly you can see the broader logic, even if it’s not the choice you’d have made. You can support it in good faith, even though you wouldn’t have chosen it.
Leading Honestly Through a Weak Why
Here’s what I think emotionally intelligent leadership actually looks like in that spot:
Be straight with your team. Not undermining but straight. Something like:
“This initiative is important. Our broader leadership team sees pieces of the picture we don’t see from here and have decided on this direction. I’ve raised some concerns about how it lands at our level, and I’ll keep raising them. But we need to help make this successful. And as we support this, I need you to be open and honest with me about the concerns you have. We will do our best to address them, and where we are challenged, I will make leadership aware.
Notice what’s happening in that statement. You’re acknowledging the legitimacy of the decision. You’re not pretending you authored it. You’re committing to advocating in both directions — for the work with your team, and for maintaining transparency with them and senior leaders. And you’re promoting honest input without inviting mutiny.
Then you actually do it. Your team works the issues. You discuss possible solutions. You voice concerns upward in language leadership can hear — specific, business-grounded, and solution-oriented. You bring context to your team, so they understand why decisions look the way they do. You become the connective tissue between levels, not just a megaphone for the people above you. And you remove the political baggage from the team so they can focus on execution.
Concurrently, you pay even closer attention to maintaining psychological safety. You are patient with the complaints and focus discussion on the facts of the challenges and prospects for solutions. You acknowledge ideas, frustrations, creativity and perseverance. And you put your team’s input in writing to provide both a living record, and an opportunity for decision-makers to reflect on their own time that provides the space for clear thinking.
The Bottom Line
We can get hard things done without doing them blindly. Loyalty to an organization doesn’t require turning off your judgment, shutting down your mind, and blindly supporting an initiative. But it often requires facing personal fears which are almost always exaggerated beyond practical reality.
The leaders I most respect have figured out how to hold both: real commitment to the work, and real honesty about its limits. That’s not a contradiction. That’s the job.
Author Bio:
After leading teams of various sizes for 29 years, I served as a Leadership
Development Program Manager for 4 years. In that capacity, I reviewed research on what makes leadership development programs effective and applied those learnings in a new program that I created called HUMan-Based Leadership development (HUM-B- LE). This program was successfully applied across 5 operations leadership teams and ultimately resulted in a measurable improvement in culture for the broader team of employees.
I earned my BS in Industrial Engineering from the University of Michigan and an MBA from the University of Colorado. In 2018 I earned a Certified Professional Coach designation and use these skills in support of helping leaders improve. I enjoy helping leaders grow a culture of psychological safety and employee engagement. Research demonstrates that these attributes correlate with high performance and improved business results. My base purpose is to make a difference in the lives of employees by helping leaders create these environments.
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