“Underpromise and overdeliver.”
I’m sure you’ve heard that maxim before.
But most of the time I spend money, I don’t expect anyone to overdeliver. I expect to get what I paid for. That’s really all I ever want. Sure, a little surprise and delight never hurt, but being friendly and caring about the details isn’t precisely overdelivering.
Yet many small business owners obsess over going above and beyond. They add in all sorts of extras that the client or customer never paid for. They’ll do anything to make a customer or client feel supported—nay, loved.
When does overdelivering become overcompensating?
You put a lot on the line when you decide to start a business. Whether you plan to build something massive or a simple structure to do your best work, no matter your vision, entrepreneurship is an act of vulnerability. The stakes are high—whether those stakes are financial, social, personal, or some combination of all three.
Every entrepreneur attempts to hedge this bet a bit. To balance the risk and compensate for uncertainty. Otherwise, you might balk at the promises necessary to get a business off the ground, close a big client, or build your product.
Underpromising and overdelivering compensate for lack of confidence and self-trust. It eases the anxiety about risk, uncertainty, and the sky-high stakes of entrepreneurship. Overdelivering can also offset a lifetime of being told—implicitly or explicitly—that you have to make up for some aspect of your identity.
And it’s on this social and psychological aspect of overdelivering that I want to focus. Earlier this year, I spoke with sales coach Allison Davis. She told me that she was struggling with the dance between upholding a value for generosity and tripping into the rhythm of overdelivering. Allison explained:
When I set out to have my own business, I wanted to actually create engagements where over-delivery was baked in. I think that’s who I am as a human being. … But how much of that is reasonable?
This is something I think about myself—mainly because the tendency to overdeliver pops up in many unexpected ways. It’s often not simply a matter of offering up more and more of yourself, neglecting your own boundaries and needs. For instance, business owners ask about what content should be free and what content should be reserved for sale. They want to overdeliver for free and in their online courses or programs. I’m prone to over-delivery after a program or training ends. I’m quick to assure participants that they can lean on me for support—free of charge.
Sean and I often talk about overdelivering for our podcast production agency, YellowHouse.Media. He often jokes that he sets a bad precedent by going above and beyond in the way he edits an episode. Or, we get into the weeds about what we’ve promised a client versus what he fears their expectations are. Producing a podcast is such a subjective activity that, no matter how detailed our proposal, there always seems to be some gray area about what we’ve agreed to and the care we put into our projects.
So yeah. I think most of us, especially women, non-binary, and marginalized people, get stuck on overdelivering in one way or another. We value generosity—but our actions can look more like entrepreneurial martyrdom.
Before we go further, let’s define “overdelivering.”
Overdelivering creates an imbalanced exchange of value because the seller provides more than is paid for or agreed upon.
In a transaction, both sides agree to the value of the exchange. We tend to think of value creation as the product we sell or the problem we solve. But it’s not actually value until it’s exchanged for something else of value (typically, money.) When we offer a service or sell a product, we’re creating potential value, which is realized when a customer provides a fair trade to use that value. This is a win-win scenario! The customer gains value in the form of the product or service. The business gains value in the form of financial compensation. Both parties get what they want. Overdelivery introduces voluntary inequity into this exchange. The customer still trades appropriate value for the ability to use the potential value a business has created—but the business actually delivers more than the potential value initially agreed upon.
No additional value is created in this exchange. The customer just gets more than what they paid for.
So why do we do this? Rationally, it doesn’t seem to make sense. In trying to understand this for herself, Allison told me that she investigated the origin of her compulsion to overdeliver—something she tries to prevent her own clients from doing.
Where does this belief that I have to overdeliver come from? I spent 17 years on sales teams at media publishing companies while they were managing their decline. Overdelivery was the last gasp. ‘You want to buy the office furniture? I’ll sell it to you. What do you want? I’ll do anything.’ And so, I think there’s a bit of it baked in [for me] because when you are coming up in an industry that is dying, you are scraping to stay alive. So, how do I undo 17 years of that?
How Allison described the origin of her tendency to overdeliver got me thinking about how we could see over-delivery as a survival strategy—one that could be born from any number of social or psychological dynamics experiences over a lifetime. And with the precarious work dynamics that we’re subject to as small business owners, it’s no wonder that our survival strategies are triggered.
Our brains use heuristics to make sense of situations quickly.
“Underpromise and overdeliver” is a sort of heuristic that we may use any time we feel like we’re at risk of underperforming, losing a job, displeasing a superior, or simply uncertain about the future. The same heuristic can pop up in educational settings, romantic relationships, and parenting.
Allison told me how, shortly after moving from Burlington, VT, to New York City for her first Big City Job, she received an email from the head of a small advertising agency she had done some work for. The email contained two graphics—the first was her name, Allison, displayed over the word “deliver.” The second graphic was her name displayed under the word “promise.”
“That’s weird, dude,” I said to Allison. She agreed but asked me, “You know what I did with that email?” I’ve been around long enough to know exactly what she did with it.
“Did you print it out and post it somewhere?”
She replied, “Sure did. Right at my desk. Wore it like a badge of honor.”
I’m baffled by this guy’s choice to send that in an email. Was there nothing more substantive he could have said? I don’t know—maybe he did have more helpful things to say. But what struck me is that surely this Very Important Advertising Man had no doubt sent that email countless times before. He didn’t have those graphics made specially for Allison. It was a template that signified exactly what he found valuable about the people who worked for him: they were willing to do more than he paid for.
When you expect to always be the winner in a relationship, you inculcate some toxic behavior. Economically speaking, it deflates the financial value of a person’s work. If I’m consistently delivering more than what you’re paying for, the actual terms of what I can expect to get paid go down (similar to the work intensification process I covered last week). Further, the expectation for over-delivery entrenches hierarchy, with the higher status party always expecting to get more than what they paid for. And it’s on that note, that we need a little feminist theory breakdown.
Feminist theory, of course, isn’t only about women’s empowerment. It’s a total questioning of sociopolitical assumptions—relationship hierarchies being among the most essential “norms” to question. We know that women are socially conditioned to act as caregivers. Not all women like caregiving or excel at caregiving—I don’t. But very few of us escape the message that caregiving is our responsibility. Non-binary, queer, and marginalized people regardless of gender, most often receive a similar message.
What if the tendency to “overdeliver” is actually a commercial manifestation of that caregiving responsibility? Is overdelivering is the labor equivalent of a birth parent’s self-sacrifice on behalf of their child or partner or even their parent? We see this dynamic throughout the work world—in the service industry, in tech, and in every corporate office building. Women and marginalized people are often funneled into caregiving roles at work—human resources, legal counsel, office manager. Our professions come to be defined by our social conditioning toward caregiving—rather than our actual skills or strengths.
Further, as feminist philosopher Kate Manne explores in her work, fulfilling our caregiving responsibilities helps us avoid the enforcement meted out by misogyny. Stepping into caregiving roles allows us the relative safety of sticking to our part. What happens to a person who defies their socially conditioned role? The more traditionally powerful people attempt to “put them in their place.” This dynamic can play out in work relationships between people of any gender, including woman-to-woman. Because it’s so easy to fall back into the default programming of patriarchy and misogyny.
Manne describes two classes in our culture: human beings and human givers. Human givers provide the labor required for human beings to simply be. That labor, of course, is reproductive, caregiving, maintenance type of work. In their freedom from that type of labor, human beings can pursue their interests and ambitions, disrupt and create, or at the least leave home and bring back a steady paycheck.
I saw this play out in real-time on Twitter a few weeks back. A guy tweeted that, essentially, he was proof that it was possible to have kids, work a full-time job, get 8+ hours of sleep every night, and build multiple revenue-generating side projects. You can imagine the response. Several women asked him about his wife and how much he contributes to caregiving. He claimed they split the work right down the middle and that his wife also works a full-time job. I find that incredibly difficult to believe on its face. And, I know there is so much more going on below the surface.
The responsibility of caregiving is not a list of chores or even hours spent with the kids. Caregiving is, in my experience, a state of mind—a state of mind that holds a complex web of preferences, needs, obligations, anxieties, hopes, and dreams all together at once. This straight white man’s assertion that it’s possible to fit all of his activities in during the day reveals that he is not the one holding that web in his mind. Because caregiving is not merely a logistical puzzle—it’s an emotional, intellectual, and social puzzle. The human giver takes on that puzzle so that the human being can be free to do more “valuable” things.
In entrepreneurship, I see this same class dynamic play out. Some entrepreneurs position themselves as human beings and, with varying success, build an infrastructure to support that. They’re the ones liberated from administrative tasks and customer service so that they can focus on what’s “important.” And then there are the entrepreneurs who assume the role of human givers, taking on a caregiving role with their customers or clients. Unsurprisingly, this can create tension, even toxicity. I’ve seen this play out among team members, between clients and service providers, in small groups, and in whole communities or audiences. An often unstated power dynamic at play can lead to harmful assumptions about who owes another what.
I’m not arguing that delegating admin or customer service is unethical or necessarily exploitative. It can be vital for the quality of your work and your emotional health as a business owner. But I am advocating for compassion and recognizing the integral role that the people we hire to do those jobs hold in our businesses. I see many business owners desperate to step into the role of a human being. They want to be liberated from the constant worry about everyone else’s needs and prioritize themselves for once. But at the same time, what’s often expected of them from customers is that self-sacrifice at the core of caregiving. It can be real social conditioning whiplash. One minute you’re the self-assured CEO who routes all communication through an underpaid assistant, and the next, you’re dealing with a complaint about not being accessible enough in your Facebook group—which you sold based on access to you.
Overdelivering seems like a way to avoid this mess—to compensate for the discomfort of being in a position you’re not accustomed to. But often, overdelivering merely entrenches these tired class dynamics.
How do we create relationships in which no one needs to be the human being to whom care is owed or the human giver who owes the care?
What does a working relationship look like in which both parties offer care and maintain boundaries? I don’t know about you, but this relationship construction feels utterly foreign to me. In the last five years, I’ve finally seen relationships where this mutuality is modeled. But actually achieving that in my own relationships? That remains elusive. My reflex is to figure out as quickly as possible what the power dynamics are so that I know my place. And then do my best to uphold that role.
Even if you don’t wade through the same social pathological muck that I do, my guess is that we build our business relationships in similarly fallow soil. This is what’s cultivates our predilection for overdelivering.
Whenever we assume the position of lower status or lower power, we overcompensate by overdelivering. And the person of higher status has learned to expect that overdelivering, that overgiving.
Consider Allison’s story again: she’s trying to prove herself after landing in New York City. She does some work for the head of a small advertising agency. He’s the one in the power position. When she goes above and beyond to prove herself, he rewards her by pointing out her overdelivering and, in the process, sets an expectation of what he finds valuable. Failure to meet that expectation means she wouldn’t earn his praise and could lose the job.
And that’s the thing about overdelivering and human giving. We become hyper-responsive to its assumptions. We internalize overdelivering as an expectation rather than a true “above and beyond” action. Anything less than overdelivering risks negative consequences.
So what can we do to resolve this?
Aside from therapy, coaching, and a dogged deconstruction of internalized misogyny, we can create fairer structures inside our businesses and build more equitable relationships with our clients or customers. Allison told me that she was starting to see the way forward as:
- Analyzing each action of overdelivering to discern whether she felt like she had to do it or whether it was something she genuinely wanted to offer
- Including the actions she wanted to continue with as part of her scope of work
- Pricing for that full scope of work
- Adjusting her client capacity to reflect the actual labor of a client engagement
How much [work] can I handle? And if it has to go from four clients only to two at a time? Well, great. But guess what? Those two that get me will make up the spread of revenue from the loss of the other two. And that’s just what it is. The only way that will happen is to put the “over-delivery” in the scope of work and explain the value.
Allison also told me that she recognizes the potential ripple effects of making a decision like that. Similar to how I explained that overdelivering deflates real wages, she said that if she keeps delivering work beyond scope, that hurts the next person her client works with by changing the expectations of what the job is worth. “We’ve got to level the playing field for each other,” she said. “That is why I think it’s good to be not only transparent about what we’re charging for the work we do, but what is actually in that scope of work—not merely in the bullet points.”
Let’s circle back to what we’re actually talking about when we talk about overdelivering.
When overdelivering becomes the expectation for our work, we’re saying that delivering on what we’ve agreed to is not enough. If we feel compelled to overdeliver, we don’t believe that merely delivering is acceptable. That seems… not right. It is problematic in terms of self-efficacy, and I think it might be fundamentally dishonest.
Allison recalled her time spent in the sales industry:
What can you add if the thing you’re selling isn’t enough or isn’t attractive enough to buy? And the only thing to add was the office furniture… or all of me. ‘Whatever you need.” From mani/pedis and fancy dinners to maybe an extra free advertisement here and there.
When there isn’t another office chair or ad spot or mini-course to throw in the bundle you’re offering, the only thing that can be added is more of you. And that is dangerous.
I’ve fallen into that entrepreneurial and personal brand pattern many times. How can I make this more enticing? Well, I’ll add in a weekly Q&A session. Or, I’ll add in email support. Or, I’ll create a Slack channel for direct access to me. How do I demonstrate the value of what I’m offering before someone buys? Well, I’ll make video after video, putting my heart and soul into as much free content as possible. Or I’ll do a webinar where my personal struggles become leverage for making a sale.
At the heart of this is a very genuine, authentic desire to connect and provide value. I don’t question that at all—for myself or for others. And yet, just because that authentic desire to connect is there doesn’t mean it’s right. It doesn’t mean it’s not harmful. It’s potentially harmful to the customer because you set unrealistic expectations even when your intention is overdelivering. But it’s also detrimental to us as business owners.
When my personal support or story becomes part of the sale and what I promise to deliver, I risk losing a sense of who I am outside of that transaction. How could I not lose myself if I constantly mold my availability and care into the form others need it to take?
In my post on emotional labor and my mental breakdown, I talked about how sociologist Arlie Hochschild said that one of the potential consequences of offering up extreme amounts of often uncompensated emotional labor is self-alienation. You lose sight of your own needs, feelings, and even your own sense of self. To my mind, this ties directly to Kate Manne’s argument that human givers aren’t allowed to “be” in their own right. They exist to serve human beings.
When I asked Allison about this potential for self-alienation, she told me a story:
I remember a conversation back in my early twenties with one of my very best friends to this day. And my goodness—the self-righteousness and bravado of our early twenties! He said, ‘I don’t know who you are. You are this person when you’re at a work event, you’re this person here. Who are you really?’ And you know what my response was at that moment? ‘You’re lucky to know all of them!’
All of those different people Allison describes, all the various people I could tell you that I’ve been in my own life and work—we’ve developed those identities to compensate for feeling like we’re not enough. We’ve allowed them to step in so that we could be whoever was needed at that moment. Sure, Allison had that whipsmart, cocky reply in her twenties—but deep down? My guess is that she’d internalized the expectation that she’d be exactly who someone else needed her to be. I know I did. And when we become what someone else needs of us, we’re sending ourselves the message that who we are isn’t enough.
When we carry that into our business dealings, it’s no wonder that “delivering” doesn’t seem like enough. There is no precedent of equal exchange for many of us. More is always demanded—if not by our partners, children, or even our old bosses, then by persistent cultural narratives.
A balanced transaction—value for value—will always trigger that overcompensation reflex in this paradigm.
In her book, Living A Feminist Life, Sara Ahmed argues that we need to really examine the “concepts” at work in how we think and behave. She writes:
Concepts are at work in how we work, whatever it is that we do. We need to work out, sometimes, what these concepts are (what we are thinking when we are doing, or what doing is thinking) because concepts can be murky as background assumptions.
What assumptions have you made of what’s expected of you as a business owner? What assumptions have you made about how you or your work isn’t good enough?
Here’s the revolutionary concept I want to share: transactions are supposed to be balanced.
Exchange should be based on equal terms. Both customer and provider contribute comparable value to meet each others’ needs.
The more we incorporate that balance into the ways we do business, the more we can realize gains outside of work.
What would it take to provide your service or offer your product in a balanced way? In what ways are you overdelivering—and maybe overcompensating—that you could either eliminate or price for fairly? What guardrails could you put in place to ensure that delivering is enough?
And where else might the reflex to overcompensate be at play in your life and work?