Being the boss of your own business does not give you unlimited freedom to do everything you want – it actually holds you back from freedom. Gwen Bortner and Tonya Kubo discuss why entrepreneurs love to resist management by their teams. They emphasize the importance of having the willingness to be held accountable and how to create a healthy two-way accountability system. They also present the biggest disadvantages of bosses resisting management, from decreased effectiveness, longer turnaround times, to poor client experiences.
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Why Bosses Love To Resist Management
Why Business Owners Resist Being Managed
What if being the boss is holding you back from the freedom you started your business to achieve? In this episode, we’re going to be talking about why letting your team manage you might be the key to unlocking the business you want. Gwen, this conversation is going to be about how we as entrepreneurs love to resist the structure we so desperately crave in our businesses. This is something you and I talk about all the time. I feel like it’s high time we bring the conversation to the show. Gwen, what I want you to do is kick us off and tell me and our audience why is it you think business owners resist being managed by their team so much.
I can give you an absolute example. One of my favorite people and a great client has said to me when we bring this up, “I’m the boss. I won’t be told what to do.” She makes all the great faces and does all the things. There’s a bit of humor but she also knows that she’s serious. It’s like, “I’m the mom that’s why.” It’s a bit like that answer of, “I’m the boss. Why would you tell me what to do?”
This is the place where we get caught in what we see typically out in the world. If you think of a CEO of a giant company, there are not very many people telling them what they can and can’t do. If they do, often they have a board who is their boss. It rarely comes much up from below. It’s usually coming down from the top. If they’re smart, they’re asking for input from the people that report to them but rarely are they the ones being held accountable by those people.
When we start saying being managed by your staff, that’s saying, “I’m going to be held accountable by someone that I employ,” whether we employ them as an employee or contractor. It feels backward because that’s not how we’ve seen the hierarchical structure work. That’s as much of the resistance as anything else. That’s a huge piece of it because we’ve got this mental framework that we all work from. The other piece is, “I’m the boss. I want to be able to do what I want.” It is a critical piece.
If nobody else is doing it, then why does it matter?
We aren’t asking you to turn over every aspect of your business to your staff to hold you accountable. We’re talking about doing it for the things that you suck at and don’t do well anyway but you may still have to be the one to do. There are some aspects of the business that are always your responsibility. I talk about all the time that the two things that are always your responsibility is the health and the culture of the business. You can’t delegate them to anybody else but you could delegate someone saying, “I want you to check on the health of the business.”
That’s not delegating the health of the business but it is delegating the process of checking the health of the business. I’m using that one because generally for me, the health of the business has a lot to do with finances. A lot of the entrepreneurs I work with don’t love the financial aspect of their business. For example, you’re the only one who can do the billing, particularly if you’re the primary deliverer and you’re doing things that are typically billable. It’s f you’re an attorney, accountant, and things like that we have to track our hours, build them, and all of those things.
If you don’t like doing that piece, then having one of your staff hold you accountable to getting that done by every Friday makes sense. I’m not saying you’re turning everything over the business to them. I’m saying they’re holding you accountable for doing that. Otherwise, you know that there’ll be lots of reasons that you won’t do it on Friday and then you won’t do it on the next Friday. All of a sudden, there’ll be no invoicing going out. You’ll be mad at the other people because it’s not going out. It’s still your fault but you’re not responsible because you don’t like doing the billing.
I went through a phase like that in my business with sitting on proposals.
I love that. That’s a great example.
I didn’t like scoping out the projects and then having to decide whether I wanted a project that big of a scope, deciding how much I should charge for the scope of that project. I didn’t like any of that. I would sit on proposals and let proposals stack up and then feel guilty about the fact that I was supposed to get that proposal done two weeks ago and I still haven’t done it. In my case, I had somebody who would ask me if the proposal was done but that’s all they would do. That felt more guilt on top of guilt.
That’s because they weren’t holding you accountable.
Holding The Boss Accountable
Use my example and tell me how they could have held me accountable. I’m going to take notes so that I can use those words down the line in the future.
There are two aspects of this. First, you have to be willing to be held accountable for getting the proposal out.
Tell me both of them and then I want you to drill into each one individually.
That’s the first piece. If you’re not willing to be held accountable and you don’t care, then there’s nothing anyone can do. The final result always is you’re an independent human being. You get to do what you want. I can’t make you, particularly if I’m working for you. There’s nothing I can do to make you. The other is being held accountable. It means that I will respond. The person is asking enough of the right questions and is able to work with you.
If you are not willing to be held accountable, there is nothing anyone can do about it. Share on XIf I was that person, for example, I would say, “Did you get the proposal done?” “No, I did not.” “Is there a reason that it hasn’t been done? Is there something that you need that you’re missing?” “No, I’m not missing it.” “Is the reason you’re not getting it done because you don’t want to do the work at all?” They’ve got to be able to ask you good questions.
That’s a good question. “Do you not want this project? If so, that’s a different conversation.”
If you don’t want the project, then let’s take that off the list altogether and we don’t have to feel guilty about it. There’s no need to propose for something you don’t want. God forbid, you might get it. This is where we get into true accountability, which we’ve talked about a few times on the show. This is a great example of it. True accountability is someone has to be able to reflect back and help you figure out why you’re stuck. It can’t just be anybody.
If it’s a VA who is getting paid $5 an hour because they’re completely out of country and don’t even understand what you’re doing, they can ask the question but can’t hold you accountable. They don’t have enough context to be able to hold you accountable. If you’ve got someone like you for me, you do hold me accountable for a number of things. It’s because I’m willing to be held accountable and have the hard conversation when you say, “Yeah, but why?” “I don’t want to talk about this,” but then I proceed to do it because I’m willing to be held accountable. Anything that I’m not willing to be held accountable, no matter how successful you are at other things, you will not be able to hold me accountable to.
You’ve done a great job of explaining what it means and what it looks like to be willing to be held accountable or what being held accountable looks like. What does being willing to be held accountable look like? A lot of us say, “I’m willing.” Meanwhile, our behavior tells everybody around us otherwise.
That’s the tricky bit. We all think we’re willing because that sounds like the right answer.
We want to be willing.
The true right answer is when someone asks the question, does your behavior change? If it doesn’t, then you’re not willing. You’re just saying the words. When I say the behavior changes, sometimes the change of behavior is answering the questions and realizing, “The reason I haven’t done this proposal is I don’t want this work.” It’s not that the proposal gets done. There’s not one right answer in the change of behavior but there is a change in behavior. Either we say, “I just need to do it,” or, “I realized what I’m missing is I don’t understand this part I need to get some clarity.” It doesn’t matter but the accountability conversation creates some new action. If there is no new action, then you’re not willing to be held accountable.
Common Places Leaders Resist Being Managed
Gwen, I’m curious off the top of your head if you have 2 or 3 common places where leaders resist being managed or held accountable by their team.
One of the places is deadlines.
I would agree with that.
Deadlines can be in lots of different places and spaces in time but having someone hold you accountable to get to a deadline of, “This has to be done by this time,” and working with you to understand either why you are or not hitting that deadline. The first issue is deadlines. We often are an entrepreneur because we don’t like deadlines.
Entrepreneurs often pursue such a career path because they do not like deadlines. Share on XWe don’t want to be told what to do. That’s why we’re entrepreneurs, Gwen.
Deadlines are a version of being told what to do. Deadlines are probably the most prevalent, generic answer that can be there. The other that’s related, and this is where we start getting specifics, is down to, “Are you not getting your invoicing out on time because you’re not doing the piece you need to do? Are you not getting bills paid in a timely manner because you’re not writing the checks,” or whatever the process can be. Unless you love the finance aspect of your business, there’s always something in the very generic bookkeeping accounting department that is another place that people don’t want to be held accountable to.
Often, that’s a place where it’s like, “I don’t want to look at these numbers or pay attention to this thing. I don’t want to feel like I’m in business because I love what I do. I don’t want to feel like I’m all salesy and grabby after money,” even though there was an agreement to trade your service for money. There can be all sorts of weird mind stuff that’s going on there. Whatever the thing is, there’s always some aspect of your business that you least enjoy. Those we also typically resist being held accountable for because it’s hard for us to do. We’re always waiting for that perfect opportunity or when we feel it, which is never going to come.
I also think about the finance part. I’m sure that there are readers who are way more evolved emotionally than I have been in the past. It also comes down to when you don’t know what normal is. You don’t want to look at your numbers because you’re afraid to confront failure. “I’m working so hard I don’t want to see that it’s not for anything.” That’s another piece that comes in with numbers. They end up being very emotional even though numbers aren’t.
Numbers are just data.
The other thing that we’ve talked about in the past, and I wonder how common this is as a resistance point, is taking on more work. I see that where there’s a staff member who’s like, “No. We are full. We’re at capacity. We can’t do more.” The boss says, “We can. You don’t understand that they’re willing to pay triple.”
That’s an accountability piece. It’s a weird version of a scarcity mindset. It doesn’t sound like it when you say it. “I’ve got to take everything that comes my way. If I don’t, what’s happening in the background is nothing’s ever going to come my way again.” Another version of that, which is different but yet along the same lines, is taking the client that is not a good client.
Also, contrary. It becomes a unicorn and you don’t have a model in place for that.
That’s another version. Often, someone else can see, “This is not a good fit for the business that we’re on but we can do it.” Most people who have entrepreneurial businesses are smart. Generally, they’re hiring also smart people, which means there’s a whole lot of things that we can do. Whether or not we do them well and can do them consistently is a whole different conversation. We get caught on, “But we could.” It’s the other version of, “I repair roofs and you’ve asked me to fix a gutter. I could fix the gutter because it’s attached to the roof but I’ve got to get a whole new set of stuff.” Having your employees say, “Yeah, but we don’t do gutters. We do roofs,” is another one of those accountability things. That’s another great example of a category.
How Resisting Management Leads To Bottlenecks
We came up with three good ones. From a CEO perspective, how does resisting my team hold me accountable? How does that create bottlenecks in my business?
It doesn’t necessarily create bottlenecks but it minimizes the chance for effectiveness.
Say more about that.
It could create bottlenecks but it’s usually more about overall effectiveness. That often means there are lots of little bottlenecks but it doesn’t necessarily mean there’s this big bottleneck like the whole thing. That’s why I’m resisting using the term bottleneck. It’s not that we feel like if we clear the bottleneck, then it’s all good. That may not be the case.
It does reduce effectiveness because you’re putting energy into trying to do the thing that you’re resisting to do anyway. You’re putting energy onto both sides of the equation. “I’m trying to put energy into resisting it because that’s not my natural tendency to do the thing. I’m also trying to put energy into doing it because it needs to be done.” All you’re doing is doing this as hard as you possibly can.
Resisting management reduces team effectiveness. You are putting energy into trying to do the thing you are resisting to do anyway. Share on XIt’s worse than fighting against yourself.
The challenge is all of that energy is technically going nowhere. As opposed to if you were able to be held accountable and know that if there’s a proposal that needs to be done, a deadline that needs to be hit, an activity that has to happen, a time that we need to say no to a potential new client, the list goes on and on, someone that doesn’t take a lot of energy for can raise the flag and say, “This is one of those times.” You’re going to trust them as much as you possibly can. All of that energy that was going against itself and going nowhere can be used to set for something else that’s way more productive.
I’m sure the polite thing to say is a benefit of letting your team lead. I’m going to say a benefit of letting your team boss you around. As a CEO, I know that’s what it feels like. It feels like they’re bossing you around and that’s what you don’t like. One benefit is that you free up energy to direct into more productive areas.
Also, things you like doing.
Let’s say I’m sitting here and I’m like, “You’re not the boss of me. You can’t tell me what to do.” Give me some other benefits I can use in self-coaching. I can say, “If I let them take the lead in bossing me around here, then I have more time and energy to do this other thing.” What other benefits could there be?
The other thing is it almost always results in improved profitability. I’m not going to say improved revenue because sometimes it’s not. We’re doing what I call straight-line behavior. Instead of wandering around, we’re getting right to the point doing the thing and that’s saving a whole lot of resources. There’s the energy resource but there is undoubtedly a whole lot of other resources. It may be other people on the team’s time or your time. You freed up time. If you’re able to allocate another hour that is generating income, sometimes it’s about creating efficiencies and real effectiveness.
You’ve been fighting it and I know this happens to you from time to time with your clients. You’ve allocated this hour to work on this project, assuming that they’re going to deliver the thing to you that you’re supposed to get and then they don’t. That hour isn’t being used the way it was supposed to. The next person who needs the thing isn’t getting the thing. Depending on a person’s model, it may be like, “I’m charging you for the hour anyway but you’re getting zero for it.” That’s a huge hit to the bottom line. “I’m paying you X dollars per hour and I’m getting zero for that because I was unwilling to be held accountable to my deadline.”
That’s what I was going to say. It’s the benefit of allowing your team to lead. You talked about profitability but in the specific example of deadlines, we are talking about timely service delivery, which ultimately is going to be client satisfaction. It also has to do with team capacity to your point about, “I set aside this hour. I didn’t set aside that hour.” It’s like, “I set aside this hour so that I could turn it around. We’ll make it up tomorrow. If you don’t get me your part until tomorrow, then I can’t turn it in until the day after that,” which then puts me behind on the next project that I was supposed to do after this one buttoned up.
It’s a cascading effect. Look at what the pieces are. We talked a little bit about being willing to be held accountable but part of that is being willing to be held accountable, which means you have to behave as the CEO. I’ve got enough clients that I can tell you, they don’t even realize that they’re misbehaving. They’re shocked when things don’t go the way they want. “This is why. You’re misbehaving.” They’re like, “But I know what’s right.” No, you don’t.
Being willing to be held accountable means behaving appropriately as the CEO. Share on XI may have said that a few times myself.
You don’t always know what’s right. Let’s use the example that you and I talked about very early on when we started working. I kept saying, “I do not feel like we’re getting any results from the marketing.” You said, “It’s because we keep changing the direction every five minutes.”
I did say that.
I believe I said to you something close to, “I consider it your job to tell me when I’m doing that you have to hold me accountable, I think that these things all line up.” I don’t know if any of your other clients have ever said that to you. “You’ve got to hold me accountable because I don’t think I’m doing anything wrong. I don’t think I’m changing the messaging or anything else. To me, this feels like the same message.” You’re like, “It’s not even close. If I knew that, then I wouldn’t need you.” This is an example of, “I have to be willing to follow the rules.” Not too long after that, if I would talk about something, I would always ask, “Does this throw off our marketing plan?”
That is a good example. You said, “That’s what I have you for.” It’s like, “But I’m still learning how to work with you and all these things.” This is important to point out. I don’t think you always recognize this, Gwen but you then took ownership of checking in. When you had an idea, you would then say, “I have this idea but you need to tell me if this throws off the strategy that we’re in play. To me, it’s the same thing but maybe it’s not. We could have that back-and-forth conversation.” I don’t think you realize in this specific example that you came to the table much more evolved than the average CEO that I’ve worked with in that regard.
I also knew that I had given you authority. At any point that I would say anything, you would say, “Wait. We need to figure out how this fits.”
That’s around the time that you would bring up an idea and I would say, “Gwen, that’s a great conversation to have six months from now. Can we write that down and have that for six months?” You would say, “We said we were going to have this conversation in six months, Tonya. It’s been six months.” It was a good partnership toward a shared goal.
Creating A Two-Way Accountability System
Here’s where I want to take our audience, though. I know that we’ve got people reading who are like, “That all sounds fine and good but how do I do that?” It would be easy to say, “You just do.” This is something that you have worked with so many clients on so I am curious if you have advice on how you create a system for this two-way accountability that’s healthy. The other piece of it is it is a healthy accountability. There’s no shame or judgment.
To your earlier point, it’s like, “Did you do the proposal? No? What is it that’s getting in the way of not doing the proposal? Is it that you don’t have enough information? Is it that you don’t want the job? You didn’t do the proposal but you said you would do the proposal. You were supposed to do the proposal two and a half hours ago.” Honestly, you’re asking the same question. “Why didn’t it get done?” You’re just asking it in a different way. When I say healthy two-way accountability, that’s what I’m talking about.
The first is the other person has to know it is their job. That was an example of, “It’s because of this and this.” It’s like, “It’s your job to tell me when it’s not. I made that clear. You have to tell me when it’s not. I have given you the authority to do that.” The other piece is you have to be willing. The first time it happens, as the CEO, you need to not get defensive. It’s the first thing. If you get defensive, they’re going to put their guard up.
They’re going to be like, “They asked me to do it, I did it, and then I got my hand slapped.”
You have to not slap their hand. Being defensive is very much a hand slap. There’ll be a point later on that you can get defensive when you’ve had a bad day and they’ll be fine with it. There’s more than once I’ve gotten defensive with you and you’re like, “She’s working through some stuff,” but not early on. You knew that that wasn’t normal behavior. A normal behavior was to say, “Right.”
The other is realizing if they’ll be able to ask the right questions. Do they have enough knowledge, skill, experience, and all of those things? If not, then you’ve got to start the conversation to say, “I haven’t. Let’s talk about why.” You help them start hearing the questions that need to be asked of you. If you’re lucky to have someone who can ask good questions, which I have with Tonya, because she asks me questions all the time, it makes it easier but you don’t always have access to that. I have not always had Tonya.
In those cases, I have to ask myself the questions. If you want to train them, you need to ask questions with them in the room so that they can start hearing what these kinds of questions are. It’s like, “Why haven’t I done it? Let’s talk about why I haven’t done it.” One of the phrases that I learned from being in a room with Chris Voss was instead of asking why, you say, “What has prevented me from?” Why sometimes gets us into a defensive posture but “what has prevented me” gets it about the thing, not about my emotions around it.
“What has prevented me from getting the proposal done?” As soon as you start asking that, you start saying, “The reason the proposal didn’t get done is I ended up in the hospital for three days this week.” “What would prevent you from getting it done next week?” “I don’t think anything.” The person who’s holding you accountable can say, “I can tell them there’ll be a proposal coming next week?” “Yes.” The other piece of accountability is it’s keeping the communications open and allowing them to keep moving forward. For instance, if your proposals end up needing to have a meeting scheduled in person with a slide deck that someone else prepared, it could be a big thing. I know yours don’t but pretend like it did.
Accountability is about keeping communications open and allowing everyone to keep moving forward. Share on XI’m sure somebody is.
The thing is there are three other people who need to be updated in the chain. Part of the accountability is to say, “Person X was going to have a week to get the slides done. They’ve got two weeks so they may want to switch to some workaround. Someone else needs to schedule the appointment but they need to not schedule it this next week. They need to schedule at least a week after the proposal has been done.” It sets into a chain of events. Part of that is allowing for the communication piece of it. It’s often things that we feel like it’s our problem. Invoicing is another classic one that I find a lot of people need someone else to hold them accountable for.
This has never been a problem I’ve had.
I’m always shocked when I hear it but it comes up way more often than I would expect.
I’m glad you brought it up. I’ve had a lot of problems as a business owner but that’s not one of them.
I’ve heard that. Sometimes it’s because people don’t want to feel like they need the money. Invoicing is saying, “I need the money.” The problem with that is you’re like, “It’s only my problem because it’s my business and all those things,” but at the point that someone else is trying to pay a bill on your behalf, it becomes their problem. It becomes a scramble. Maybe you’ve got money you can transfer or do whatever but all of a sudden, it becomes somebody else’s problem. It’s the pieces that we’re not naturally doing. If not ask the good questions, it at least helps you brainstorm through them a little bit.
Let me take us from the top. This is an episode where while we give some pretty practical advice that any audience could implement, it is not easy and will not be implemented overnight or in a month. It’s important to set that expectation but I also think it’s important to summarize with the understanding that this will take time. You and I in that marketing strategy example did not button that up probably for 3 to 6 months. We made incremental progress toward it but it was not what I would say solved for several months.
Technically, it’s still not solved because every once in a while, something comes up. That is our process so it’s not a problem.
What Accountability Looks Like
We have that healthy two-way accountability established. We both know what role to play in the conversation. Let’s go back to the topic at hand, which is the power of letting your team lead. You are the boss and you are getting in the way. We’ve covered the common resistance points. I love that we talked about a few examples and it came down to, “Are you willing to be held accountable? What does it look like to be held accountable so that you can recognize that when they’re trying to do it?”
This all comes down to benefiting the bottom line by improving the effectiveness of your organization, whether your organization is 2 people, 5, 10, 20, or so on. As far as the system that you can create, it’s about, first, what I heard is to say what you expect from your people. If you expect them to be the one who makes sure the thing gets done, you need to tell them that. Don’t get defensive when they do what you told them to do. That’s probably the hardest because I don’t think people intentionally ever get defensive. That’s why we call it defensiveness. It’s an impulse.
To the point of that also is as much as possible, go the opposite way, which is to reward them and congratulate them for doing it.
That’s good. That is something that you do. You will say, “Thank you so much for saying that and bringing that up.” “I don’t like that you did that.” Sometimes you’ll say that. “I don’t like that but thank you.” Say what you expect. Don’t get defensive when they do what you told them to do. This is going to be the hardest for anybody who isn’t used to this process already, which is then evaluate whether they have the skill and experience of asking you effective questions to figure it out.
Sometimes, we don’t even know how to ask ourselves the questions. How could we evaluate what they should have asked us? As best as you can, if they’re not able to, then you need to figure out how to ask yourself the questions and ask them out loud with them so that you’re modeling that. You’re then having open productive conversations moving forward.
What I will say is if you work through this and you realize that you’re not capable, that is a sign that you need a coach, an advisor, or some outside person to start working that through with you so that you can figure out what those good self-coaching questions are because then you can give them to your team member. Is there anything else you would add to this, Gwen?
I’m going to reemphasize that this doesn’t mean that you’re no longer the boss. It means that they’re helping you be more effective in the areas that you are naturally less effective in.
Closing Words And Episode Wrap-up
Thank you so much, Gwen. This is an episode that I can see myself listening to several times even though I hate the sound of my voice. There are some good reminders and practical tips. It’s going to be a layering process. Readers, if you’re going to try to do it, you’re going to stumble a little bit and keep at it. This is one to bookmark or whatever the bookmark equivalent is for shows. Our time is up and it goes so fast.
I will say that if you want a weekly nudge toward building the business you want, you want to start practicing some of those fun questions in a very low-risk way. We have a premium newsletter that Gwen has thought up called Insight to Impact. In that newsletter, once a week, Gwen will send you a thoughtfully crafted reflection question. They’ll come every Friday. The best part is that when you take the initiative to respond to that conversation, then you get a response back with some insights that will help you take another step toward implementing positive change in your business. You can get details on that at EverydayEffectiveness.com/Impact. Until then. We’ll see you again.
Mentioned in the Episode
- Want a weekly nudge toward true accountability? Check out Insight to Impact, our premium email subscription.
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.
