The Dangerous Questions Great Leaders Dare to Ask
If you want real feedback, stop seeking easy affirmations. Start welcoming raw truth.
I once had a team member tell me, flat-out:
“We knew you wouldn’t listen. So we stopped speaking up.”
That line haunted me.
Because the truth is... I thought I was open. I asked for feedback. I ran the surveys. I did all the things.
But I wasn’t asking the right questions.
I was fishing for affirmation... not truth.
When you feel like you are drowning in a sea of issues, it’s hard to prioritize inviting more people to share more areas for improvement.
And yet, without these insights, as a leader, you cannot direct your team well.
Here’s the good news: You don’t have to address all of the feedback.
And the not-as-fun news: But you do need to seek it.
One of the most valuable, but underutilized, sources of intel is your team.
They are the people closest to your customers, your partners, and your operations. They know where you’re winning and where you’re missing the mark. They are your best brand ambassadors, and they know where all the bodies are buried.
And yes, I know. You already ask for their feedback, regularly:
You run annual employee engagement surveys.
You create space in your team meetings.
You ask your direct reports in your 1:1s.
Isn’t that enough?
No.
Even if you do all of that — and I bet there are one or two you miss (I certainly did) — you aren’t doing enough.
Why?
Because it isn’t enough to ask for feedback.
Why your team doesn’t tell you the truth.
Let’s be honest. Even if you’ve built trust with your team, most employees, most of the time, have some fear.
The fear might not be about you, but it could be about the company, the industry, their goals, or some other aspect of work.
These fears may not be guiding their work day-to-day but they certainly impact their ability to take risks.
One of the biggest risks for any employee is speaking up and raising concerns.
The “What if’s” are endless:
“What if they are seen as a naysayer?”
“What if what they share is obvious and they’re viewed as not sophisticated?”
"What if the company has no intention of dealing with what they raised, and their point of view puts a target on their back for being out of alignment?”
”What if they are viewed as an instigator and troublemaker?”
These are real, valid fears, and can only be counteracted if you, as the leader, choose to tackle them head-on.
Ask these questions instead.
Open-ended questions are great when you have established norms where employees know that raising concerns will not end in punishment. Unfortunately, that’s not most workplaces.
In most organizations, open-ended questions result in silence.
So how do you help your team take the risk and speak up?
Get specific with your questions.
Stop hiding behind anodyne, vanilla questions that make it clear you don’t want to really hear the hard stuff.
Go for the jugular instead.
Here are some examples:
Where is leadership missing the mark?
What are the issues you don’t think we are addressing as a company
What would make our company 1% better?
What would make our company 100% better?
What is the easiest change or investment we could make that would have an immediate positive impact?
What’s a hard change or investment that we should seriously consider because of the size of the impact?
Why do people leave?
Why do people stay here?
These questions might feel like you are asking for dissent. But that’s not the point.
They are invitations to help you improve the organization.
What you learn should guide you to make your company stronger, more purposeful, and a better place to work.
What to do with the feedback you receive.
The surest way to create a safe environment where your team will speak up is to have a clear process for evaluating what they share and determining what you will address.
When people see follow-through, they start to believe in the system.
Some ideas on how to make this a reality:
Create a committee
Time-bound the evaluation process
Make the decision criteria transparent (e.g. impact on revenue, impact on expenses, strategic alignment, etc)
Highlight what you address and close the loop when something is implemented
Celebrate all the inputs, and especially the ones that are implemented and make a positive impact
You don’t have to start with all of these.
Make it clear to your team that it will be an ongoing process to make employee feedback a priority. Give yourself permission to launch with a v1 and iterate over time.
What do you do if your team raises issues that don’t align with your values or goals?
Every answer is helpful feedback. If you notice misalignment, it’s signal that either:
Your values and goals aren’t clear enough to the team and/or
You have team members who likely are not a fit because they don’t agree with your values or your goals.
Start with your current team and prioritize helping managers to align with their employees.
If there’s a significant disagreement, then it’s time to gently but efficiently part ways. That isn’t retribution for answering honestly. You aren’t penalizing someone for expressing themselves.
You’re creating an open and transparent environment where misalignment can be addressed and helping your team stay focused.
For the person who is misaligned, they likely don’t feel motivated by your goals or values. That’s not a great environment for their growth or success. Parting ways will give them an opportunity to find a place that better fits their priorities.
Then look at your hiring practices. Recruiting is the first step to ensuring you are creating a team that is well-aligned on values and goals.
Your job isn’t to be a great place to work for everyone.
Your job is to create a great place to work for people who want to work in your environment with your mission.
If it’s a hustle culture, fine. You might not be great for caregivers or people who have a desire for significant activities and relationships outside of work.
If it’s a culture where accelerating business growth is priority number 1, that’s ok too, but make sure your people know and know what’s expected of them.
You might lose some people in the process, but that is the cost of creating great alignment.
The benefit? Your remaining people will move faster and with greater ease.
Key Takeaways
Your greatest source of insight is right within your organization: your team.
Create practices and a culture where you solicit their input, especially their concerns, to help you avoid missed opportunities and to build a culture of shared ownership.
Don’t rely on open-ended questions. Get specific to get real.
Demonstrate your commitment by following through with recommendations that support company priorities and that can be resourced.
Address misalignment by first clarifying your goals and your values. Then work individually and on your recruiting process to avoid future misalignment. It won’t be easy, but it will help your aligned staff work more effectively.
The next time your team falls silent... ask yourself what questions you haven’t dared to ask.
📨 Know a leader who wants to engage their team deeply but needs help?
Forward this to them. Maybe it’ll give them ideas and a helpful nudge.
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May you lead without limits,
