As leaders rise, honest feedback gets harder to find—not because people don’t care, but because questioning the boss can feel risky, disrespectful, or emotionally charged. In this episode of The Business You Really Want, Gwen Bortner and Tonya Kubo explain why every CEO needs at least one trusted person who will push back, ask the tough questions, and reveal what they can’t see alone. They unpack what makes a question “hard” (hint: it’s rarely the words—it’s the emotional discomfort, blind spots, and hidden assumptions) and why accountability often breaks down when the power gap is too wide. They also share a practical roadmap for finding real pushback—whether through a true #2 internally, the right peer group, a coach, or an experienced advisor—and show how to create a culture where your team feels safe challenging you without fear of fallout. If you want better decisions, clearer priorities, fewer preventable crises, and a team that solves problems instead of nodding along, this conversation will transform how you think about leadership—and the questions you’re willing to face.
Mentioned in this episode: Subscribe to Gwen’s weekly email, One REALLY Good Question, at www.tonyakubo.com/question.
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The Power Of Hard Questions: Why Every CEO Needs Someone Who Pushes Back
The Challenge Of Receiving Honest Feedback
Your growth is always going to plateau at the level of questions you are to face. As leaders grow, honest feedback becomes rarer and rarer. Anybody who has climbed the ladder can tell you that is true. It’s not because people don’t care. It’s not because people aren’t invested in your success or in the success of the organization. It’s because they are afraid to step on your toes. They don’t want to offend you. They don’t want to talk out of turn or be bolder than the position you have given them. I’m going to have Gwen unpack this for us because she tends to work with CEOs at a much higher level than I do. She always stays out of the business rather than getting into the weeds of the business.
I’m much more of a work under the hood service provider. I don’t care how much revenue is but we’re going to explore why every CEO needs to surround themselves with people or at least one trusted person who will ask hard questions and how you as the CEO can create a culture where the people around you feel safe challenging you. Gwen, let’s address the biggie here because I do think what I said is true across the board. That is that the higher you climb, the more you are surrounded by yes men and yes women. Why do you think that’s the case?
Why Questioning The Boss Feels Like Disrespect
There’s so many reasons but fundamentally, it’s about the culture that we have which we respect. We’ve been taught that we need to respect the boss and questioning feels like disrespect. It’s not but depending on how it’s done, it can be disrespectful. It’s a challenging piece to figure out how you ask the question in a way that is respectful. How do you have the hard conversations? Often, the other reason is everyone else in the organization is so focused myopically on their particular piece of the puzzle. They’re not in a position and they know that. That’s the thing. They’re like, “I don’t push back because I’m pretty sure I don’t understand everything.”
It’s a challenging piece to figure out: How do you ask the question in a way that is respectful? How do you have the hard conversations? Share on XIt becomes easy to defer and say, “I’m not going to push back.” Even if it’s an environment that supports pushbacks and questions being asked. There is a peer level thing. A great COO will push back. That is their job but a lot of folks don’t have one, even if they have a COO. They don’t have a COO that has that relationship with their CEO that they can push back and ask hard questions and say, “I know you want to do this but we’re not doing that.”
You’re right that a good CEO will push back but a lot of CEOs don’t know that. They’re out there hiring COOs who will co-sign whatever idea they have.
They’re hiring a duplicate of themselves instead of hiring an opposite of themselves.
Misconception Of A “United Front” Vs. Productive Disagreement
One thing we talk a lot about is the importance of a puzzle piece. We should fit together to make a better hole. We shouldn’t think the same and feel the same about you. Part of it is your point about the perception of authority and that over politeness. People mistake a united front to be, we think the same and we believe the same at the top. A united front is we have two entirely different perspectives that we are not afraid to bring up and to articulate. When we come to an agreement, we are assured that agreement is the best course of action for the present and the future of the organization.
We should fit together to create a better whole. A united front means we have two entirely different perspectives that we’re not afraid to voice and articulate. Share on XWe’ve all seen it. You and I have both worked in corporate environments of some sort or fashion. It’s so easy for us to defer when we’re not at the top of the situation. This is why I’m a big fan of, you need someone who’s going to be willing to ask you the hard questions. My belief is the less skin they have in the game, the more likely they’re going to be able to ask you the hard questions. If the response is, “That’s stupid. I’m not doing that or I don’t want to deal with this.” It’s no skin off their nose back to, this is why it’s a hard job even for a good COO because they’ve got skin in the game. If they’re asking a hard question and they don’t like the answer, they’ve got to deal with that.
It’s going to affect them in who knows how many different kinds of ways. If you have someone who doesn’t have skin in the game, then they can keep pushing. You can make what they perceive as a stupid choice and it doesn’t affect their paycheck. If they’re being hired as an outside consultant, which a lot of times they are. It may affect their paycheck because at some point it’s like, “I can’t afford to pay you anymore to do this service.” You’re not their only source of income. It’s not the paycheck. It’s only one of many.
I want to back up a minute because we’re talking about asking the hard questions. You’ve got to have somebody who’s willing to ask the hard question and I hear that all the freaking time. Do you know what nobody ever says? What makes a question hard? This vague hard question thing, can you break that down for me?
Defining A “Hard Question”
I don’t know if I can. To me, the hard question is the question that never occurred to you because it’s either so against your natural grain. It’s so contrary to the way that you would normally think and/or it is the question that somewhere deep back in your head you have been thinking about that you’ve been afraid of verbalizing. How would you define a hard question?
What you’re talking about is questions that confront blind spots. Which I think are hard. It is hard especially for founders to come to terms with the fact that they have gotten this far and they have this blind spot to anything. I do think in the heart of hearts, they believe that they’ve got it all covered. I agree with you there. I also think that part of that confronting blind spots has to do with revealing your assumptions. Part of how you get a blind spot is that you’ve just been going along assuming things are true then somebody says, “That’s not true.”
It doesn’t have to be true.
They’ll say things like, “What makes you say that’s true?” It’s like, “It’s because of this and this,” then they point out like, “That’s all based on assumption. That’s not based on fact.” You have to go, “If that’s wrong, what else is wrong?” That 100% is in line with what you’re saying. Hands down and non-negotiable, what makes a question hard and what makes most people hide from hard questions is emotional discomfort.
What makes a question hard, and what makes most people hide from hard questions, is emotional discomfort. Share on XI would never put it that way, but that’s exactly true.
As a boss, I don’t want to be asked questions by people who report to me that make me emotionally uncomfortable. That makes me think, “Maybe I don’t have it all figured out. Maybe I am not fit to lead this industry or even this individual who’s asking me the question.”
The culture bit that we’ve talked about. We’ve built a culture, which is a stupid culture of whoever is leading has all the answers. That’s just stupid, as you said, you don’t want to be asked something like, “I don’t.”
Part of it is it challenges your identity. On the flip side, as an employee, the last thing I want to do is make my boss feel uncomfortable. I don’t want to see my boss’s insecurities come up. I don’t want my boss’s feelings to be hurt and disappoint them. I don’t want to be the person who has to point out that they don’t have it all figured out. That’s a lot of emotional labor to shoulder for me as an employee. It’s just easier to be a yes man.
Part of it is, do you know what you’re doing? They become self-doubt and me as the employee of like, “Do you know what you’re doing? Is this all just smoking mirrors? Am I following somebody that doesn’t have a clue?” One question would never get somebody there or at least I hope it will get somebody there. If you’re the person bringing up lots of questions a lot of time. All of a sudden, it’s like, “They don’t have a clue. They don’t know what they’re doing. I should be running this company” There’s that whole piece that comes with that. As you said, there becomes a very large emotional burden on the employee if they’re the ones asking all the hard questions.
I don’t know if we’ve talked about it on the show before, but you’ve talked about it. Where some people assign their businesses roles in their personal life that probably aren’t that healthy.
You’re right, I don’t know if we’ve talked about it on the show before. A lot of times, the business is substituting for all of their relationships. Sometimes, it’s substituting for all of their enjoyment and fun. One of the questions that I asked early on is, what are your hobbies? A lot of the entrepreneurs say, “I used to or sometimes I.”
Often, business takes the place of relationships—or even the enjoyment and fun in life. Share on XYou need a hobby because your business shouldn’t be your hobby. I’ve also been in some situations where, “I have to work. I’m working 10 hours, 12 hours and 15 hours.” We can fix that. We do things that should fix it and it’s not. It’s like, “It’s because you don’t want to spend time with your husband, your wife, or your kids, and/or you don’t have any other friends.
To recap that piece. The reason is, it’s hard for even a leader who wants to be held accountable to find people to hold them accountable as they become more successful. It’s that perception of authority. It’s the team going, “You’re the boss. Whatever you say goes. I’m not going to spend too much time or intellect worrying about the house and wise because you, oh, great powerful all-knowing CEO sees mechanisms in motion that my little tiny brain never could.”
Also, what makes hard questions hard is hard not just for you as a CEO to hear, but also for your team members to say. There’s the emotional discomfort part. You don’t want to be emotionally uncomfortable. They don’t want to make you emotionally uncomfortable. It’s the confronting blind spots. None of us like to know that we have been walking around this giant ignorant area. Even though we’ll say, “I know I have blind spots.” We don’t believe we have blind spots. We say that sometimes so somebody could be like, “You’ve thought of everything.”
Accountability For Effective Problem Solving
The thing that we didn’t talk about but it’s so important is real accountability needs to be very close or above peer level. If they’re not exactly up, they need to be pretty close or if they’re not close, they need to be significantly above you and not significantly below you. Part of accountability is problem solving. It’s reflection, but it’s also problem-solving once we identify things. If you’re a CEO and the person who’s bringing it up has only been in business for two years. The chance that they can help you solve a problem that you’re having. They might.
There could be some insight or some experience or whatever that will allow that to happen. Most of the time that’s not the case. You need someone that’s got some experience and some chops to bring to the conversation. That’s another thing that is why accountability within the organization is hard. There could be some people in there as I said. The whole CEO example is an example of someone who could come in to help think through and problem solve. Someone in a larger organization, a mid-level person probably doesn’t have enough experience across the board to help you solve the big problems.
Which brings us to the next point, which is how do you find people who will push you or how do you cultivate them. Sometimes, there isn’t anybody. Especially if you’re in an industry that’s super confidential or highly competitive and cutthroat. Who you can trust is rare. Sometimes, it’s not so much that there’s somebody already out there who can hold you accountable or who can push you to those hard questions. You’ve got to cultivate that within somebody.
I want to go through the list of people that come to mind for me in reverse order of first to think of and maybe last to think of. I want you to tell me what works and doesn’t work or maybe even the best-case scenarios or worst-case scenarios for that type of person. When it comes to cultivating, you can look at your internal leaders. If you identify as number one in your organization, you should always be actively seeking a number two.
You either hire your number two or you build your number two from within. That is probably the first place to look because you don’t have to worry about trade secrets or anything like that. You don’t have to worry about educating them on the industry. They’re already there. They already know the nuts and bolts. You have to cultivate that culture of accountability. That’s more on you than it is on them. You have to show that they can trust you with their honesty.
You have to cultivate a culture of accountability, and that responsibility falls more on you than on them. You need to show that they can trust you with their honesty. Share on XI would say peer group. When I say peer groups, I’m talking about external professionals at the same level. If you are a retail shop owner, your peer group would be other retail shop owners. They don’t necessarily have to be selling the same product or in the same niche, but you’re all running retail shops. You all understand that though your store is different from their store. There are certain things that are just true about running retail businesses.
This is where the groups like women’s professional organizations like Vistage, McKay, the young entrepreneur’s organization. All of those potentially fit in that environment where a relatively small group. There are certain requirements to come in and it’s not like a pay-to-place situation. You need to have this level of experience. I know in the Women Presidents Organization, you need to be running a million-dollar business to come in. They also have what they call the Platinum level, that you need to be running a $20 million business more.
They also understand the people running a $1 million or $2 million business or dealing with different things than a person running a $20 million business. That is another environment. It can be a paid environment like those or a self-created environment where you say, “I know several other people that are at a similar level dealing with similar kinds of things that we don’t feel that we’re competitors. We want to have this conversation together.
External Resources For Accountability: Peer Groups, Coaches, Advisors
After that I would say there’s coaches. Coaches are nice because you lay the ground rules when you hire them. Generally, though, a coach would be somebody who you are hiring to help you make best use of what you already know. Coaches tend to be great at asking questions but they’re not great ways at giving you additional perspective. Not if they’re practicing true coaching. For example, a good friend of mine was put in a position of leadership.
Her division had gone through a lot of leadership turnover. Every leader was run out. They didn’t have a leader at the time when she was promoted to her role. There was nobody to mentor her but she also was like, “Chances are they’re not going to hire somebody here. That person’s either going to be aligned with me or not aligned with me but I’ve got to figure out how to navigate it if it’s just another repeat.”
They’ve hired an executive coach who had some understanding of the industry who could help her figure out how she wanted to lead, what her leadership style was going to be and how she was going to leverage that style to navigate these wonky politics in the organization on top of her day-to-day job. Which was not navigating politics. That’s an example of a coach. From a coach, this is where people don’t necessarily realize that there is another type of professional or another type of person who can hold you accountable and push you. That is the advisor. You are an advisor, so you know exactly what the advisor does.
Sometimes it’s for mentors also.
We’ve heard of mentors and advisors. I’ve heard people bring in martial arts and meditative terms for it. I’ve heard it called an OB-1. Who’s your OB-1? The advisor stays outside of the business much like a coach would. The advisor brings the sum total of their personal professional experience. The personal professional experience of everybody they’ve ever worked for and with. Also, your professional experience and insight all come together to say, “Based on what we know and what we’ve seen over the last 2 or 3 decades.”
Typically, advisors have to have about twenty years under their belt, if not more. They say, “Here are the things that I see trip up people in your shoes now. Here is what I’ve seen make or break a person in your position. Here’s how we can navigate around that.” What are your thoughts on those ideas? Is there a particular stage of business where you should look at each individual type of person?
The first one you talked about is the most valuable if you have access to it. Assuming that a lot of our readers are not in the large organizations. They’re not going to have an internal leader. That’s where the challenge is. You usually need to be of an organization probably of at least 50 before you start seeing that.
You may have someone at a small organization. Sometimes you get lucky and you figure that out pretty early. To me, that is the challenge. Are you hiring? Do you need the roles that would be at the level? If you do get that level, can you afford to pay them at the level that they need to be for that? That would be the challenge for the first one. It’s much more about the size of the organization.
With peer groups, as I said, the advantage of them is their outside perspective. They’re usually dealing with a lot of similar things. The advantage of the pay to play is you get consistency. When you’re doing it on your own, you’ve got to have everyone dedicated to it. I know of a lot of people in a lot of situations where those groups have been self-sustaining and self-maintaining for a long time. To me, that’s about commitment. That’s the risk if you’re not paying to play in one of those organizations.
You’ve got to have people who are very committed, but I can see both of those work. They can technically work at any size. I’ve seen that work in very small situations. I’ve also seen it work in bigger situations. The advantage typically is you’re getting more perspective because it’s not just one person. Sometimes there’s a facilitator. Usually, in a paid situation facilitator and the other sometimes there’s not. The groups are usually small-ish. It’s not hundreds of people. It’s usually anywhere from 5 to 20. It’s a smaller group, but you’re able to develop a relationship and see how that goes. That’s the advantage of that.
You can potentially get lots of perspective on any particular thing. Which you may be like, “Eight of those things were stupid, but this one is the one that makes sense.” When we talk about the coach versus the advisors/mentor, if we’re going by, what I’m going to call two definitions of coaching, isn’t necessarily helping you solve the problem. They’re trying to pull the information you know out of you but they are going to ask hard questions.
Depending on what you’re needing, that can be it. Where it’s like, “I just need that.” There’s also that advisor/mentor. Depending if you can find a mentor. A lot of times a mentor is doing it as a volunteer thing. The downside of that is, it’s volunteer, so they’re not at your beck and call. Generally, they are someone that’s well respected in your world and you’re going to want to use them judiciously. That’s the downside of that situation. Whereas, if you’re paying an advisor, you know what the schedule is.
You’re expecting the time and you’re expecting to do the work. That’s what you’re paying for. It’s the consistency of the information. The challenge there can be, are you looking for someone who has industry knowledge? Are you looking for someone who has broader generalist knowledge? What are the things that you need? Sometimes, you need industry knowledge. You need to find a particular set of skills. In other times, you want broad knowledge because you’ve got industry knowledge. You want to be thinking about it in bigger ways or unique ways that your industry would never come up with.
Sometimes, that’s the question. What if you did it this way? It’s not truly a blind spot. It’s just like, “No one does it that way.” No one in this industry does it that way but it’s a way that you could do it. Let’s talk about what that is. Sometimes it’s, are we looking for alternative ideas and questions? Looking back to the coaching versus the mentor or advisor space of, are we looking to figure out what’s within ourselves or are we looking to get fresh ideas on things and ask hard questions?
Thank you for that because that was a good breakdown of where each comes into play. People oftentimes get that they hire a coach because they don’t know who else to hire. They get frustrated because the expectations they had of a coach are much more in line with an advisor or sometimes even like with an internal leader.
They expect that coach to do a deep dive in their industry and their business. That is not what coaches do. Thank you for breaking that down for us. Where I’d like to land this episode specifically, it goes back to what you said at the beginning, which is the team culture piece. Assuming that our reader has at least one other person that is on their team. What could they be doing to strengthen that strategy and team culture? How can hard questions help?
How Leaders Can Model Asking Hard Questions
There’s two sides to this coin. One side of the coin is helping them learn how to ask hard questions. Which is by asking them hard questions and not giving them the answer. That’s our default mode. People come to you with a question about anything. Often, for you, it’s an easy question because it’s your business. You built it up and you’ve done all the things. Our default is to look smart and answer and/or do the easy thing for us, which is, “Here’s the answer. Go here. Do this.”
If you start developing the process of being curious and asking questions and saying, “What do you think the answer is? How would you approach it? Where are you stuck? Getting in that habit of asking questions so that people start seeing that that’s a way to process and think. That’s one of the things. Now, with the pervasiveness of the internet, we add on AI and all the rest of it. We’ve gotten to the point of like we don’t need to know anything. We don’t need to be curious. We’re just like, “Put it in Google. Put it in chat. Put it in whatever AI tool that we’re using.”
We say, “That makes sense. We’ll do that.” Not doing a human version of that is one side of that coin. It’s for you to model asking questions. The other side of the coin is relatively easy but you’ve got to be very conscious about doing it. That is when someone asks a question, when someone does anything that’s even close to where you want them to be to make sure we’re rewarding that behavior. When I say rewarding that behavior, I’m not talking about giving them some little prize for it. It’s saying, “I love that you asked that question.” It’s also getting comfortable with, “I don’t know the answer, or I need to think about that. That hadn’t occurred to me. I’m not sure how I want to respond to that.”
Getting comfortable with not knowing the answer—and showing it’s okay to pause, reflect, and think before responding—is a true mark of thoughtful leadership. Share on XShowing that it’s okay. Back to creating that emotional safety piece that you were talking about, I’m not going to emotionally respond in a way that makes you uncomfortable. People are like, “Maybe I could ask this other question because it’s weird that we’re doing X, Y, and Z.” They asked the question of X, Y, and Z. Sometimes, it can be like, “That’s a great question. We should have covered that in your onboarding. There’s a big why behind that.
If we aren’t, that looks like something we need to fix. Here’s the why, or we’ve just been doing it that way for a long time. What’s your suggestion?” Modeling that in what I’m going to call the low stakes questions so that people get comfortable asking higher and higher stakes questions. It’s both sides of it, getting them comfortable at being asked questions so that they get more comfortable asking questions.
The end result is we get better decisions out of the deal because we have evaluated all areas, all aspects of it. It clarifies priorities like with your example just now. It’s like, “Why do we do this thing? It never made sense to me, but I never thought to ask about it.” You go, “We do this because of this and this.” You’re like, “That makes sense now.” Also, fewer crises because a crisis typically emerges from something happening that nobody saw coming.
In some cases, natural disasters for instance. You can’t see that one coming, but you can know if you live in an area where there are natural disasters even every 100 years. You can prepare for those natural disasters. In general, asking hard questions will ultimately lead to fewer crises and to the emotional safety point.
This is where people underestimate the power of building a culture of hard questions. People think that if I let my staff ask me hard questions, I am going to lose authority or I’m going to lose respect. In reality, when you let them ask you hard questions and you show that you can handle that and you in turn ask them hard questions. You’re developing a strong basis of trust with each other.
You are and the beauty of that is all of that is the basis of a good accountability process where you can look to say, “We’re not looking to be right or wrong. We’re looking to solve the problem.”
The problem is the enemy. Not you and not me. This was so good. What we’re talking about is why every CEO, even you dear, reader, needs someone who pushes back. Whether they’re in your organization or out of your organization. You will be much more effective as a leader and you’ll be much more successful in business if you develop a culture where it is safe to ask you hard questions. Now, maybe you have to hire that out. Maybe you’ve got a number two in your organization.
We’ve talked about a variety of ways that you can make that happen. The thing to know is if you’re looking around and going, “There is nobody who pushes back on anything I say.” You’re not alone. That is very normal as you become more and more successful in life, whether you work for a corporate environment or you are the founder or CEO. The main thing is to understand what makes a hard question hard so that you can be more open to it and give people around you permission to ask them.
Also, to Gwen’s point. The best way to get people to ask them is you start asking other people the hard questions. If you have to hire it out, we gave you a roadmap for doing that and it helps you to see where your organization and you as a business owner will come out the other side stronger once you have that solid process for asking and answering hard questions.
The best way to get people to ask hard questions is to start asking them yourself. Share on XNow, maybe you’re like, “I don’t even know what that looks like.” Maybe it’s a hard question. Maybe it’s not a hard question. Maybe you want an example of what it could be to be pushed gently, then you need to subscribe to Gwen’s email that we call so cleverly, One Really Good Question. It is exactly as it sounds. It is one good question landing in your inbox every single Friday. You can choose to make that a personal reflective question and journal on it.
You can think about it for half a second. You can archive it or delete it. Do whatever you want with it. If you choose to hit reply and give an honest response. Gwen will repeat. Gwen will reward that honesty with her own response. It’s a great way to have a one-on-one conversation with Gwen by email. It’s also a great way to practice that process of accountability and to see how it feels to have somebody else push back a little bit on a hard question and your response to it. Until next time. I want you to be thinking, what would it look like if you had more people around you who knew how to push back and ask hard things, versus people who just agreed with everything that you said.
Mentioned in This Episode
About Your Hosts
Gwen Bortner has spent four decades advising executives and entrepreneurs in 45+ industries. She helps women succeed in business without sacrificing happiness by identifying their true desires and aligning their business functions. She spots overlooked bottlenecks and crafts efficient plans toward sustainable success that center your values and priorities. Known for her unique approach to problem-solving and accountability through the G.E.A.R.S. framework, Gwen empowers clients to achieve their definition of success without sacrificing what matters most.
Tonya Kubo is a marketing strategist and community builder who helps entrepreneurs build thriving online communities. As co-host of The Business You Really Want and Chief Marketing and Operations Officer (CMOO) at Everyday Effectiveness, she keeps conversations on track and ensures complex business concepts are accessible to everyone. A master facilitator with 18+ years of experience in online community building, Tonya takes a people-first approach to marketing and centers the human experience in all she does.
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