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022: Battling Boss Shame Through Systems

Tamara Kemper is a teacher, instructional designer, and operations consultant who, along with her team, helps mission-driven business owners create and document the systems that allow them to scale and remain a wonderful place to work.

Creating a New Definition of “Boss”

Tamara Kemper has always struggled with the word “boss.” For her, the word connotes a sense of superiority with which she’s never been quite comfortable.

Instead, the word “boss” should speak to how a leader can empower others around them. For Tamara, a boss is “somebody who is building the skills of her team, bringing them to see or encouraging the gifts in themselves, helping them find the ways that they can shine and grow, and spreading everything she can in her expertise to people who need that expertise.”

That’s exactly what Tamara does as an entrepreneur: help other bosses who are ready to scale their businesses create and document the systems they need to empower others to do the work for them in a standardized way that aligns with the company vision. Oftentimes, it’s the things that are most obvious or come most easily that these bosses most need to share with others.

“So, when you're ready to go from this rock star just figuring things out to we want a whole bunch of rock stars – we want there to be a rock star way to do it – that's when [you’re] ready to work with us,” said Tamara.

Boss Shame

Boss shame (n.): the feelings of self-doubt, isolation, or embarrassment evoked by the misconception that entrepreneurs must always have it all together

One of the biggest obstacles Tamara sees her clients come up against is boss shame – this idea that they should have all the answers at any given time and the resulting feelings of inferiority that come with moments of uncertainty.

Boss shame can stem from two places: (1) a desire to solve messy, tricky problems for the fulfillment that comes with finding a solution, or (2) because we feel like we should know everything and be fully responsible for carrying our visions. We might also feel embarrassed to ask for help or admit that we don’t know something as a leader in our field.

“Everybody's acting like they've already figured it all out. And really what you have is a room full of people who are all making it up one day at a time,” said Tamara. “That's why I love entrepreneurship. Because it is a journey. It is such a fun, wild, weird, crazy ride that I don't even know [half of the time] how I did this [or that].”

She added: “If we all had to wear a Post-It note on our forehead that says, ‘Hi, my name is Tamara. I'm currently struggling with _____.’ you know, that would probably open up some really interesting conversations, because I bet there's three other people in the room, five other people in the room who are going through that or maybe who have the solution to that thing.”

The Pitfalls of Boss Shame

Boss shame is something Tamara has struggled with personally, too – in fact, on almost a daily basis. For her, it presents as an icky feeling in her gut that insists she must excel at everything.

While feelings of boss shame are natural, we can’t let them make us stagnant. On the one hand, the constant grind toward excellence often keeps us from doing anything; if we can’t fully realize something to our vision, why do it at all? On the other, it can also lead us into a pattern of over-delivering to make up for our lack of perfection.

“I think there’s always this one thing in your business where […] you know what it would look like if it were excellent, but you literally do not have the skills or resources to do it today,” said Tamara. “And you just have to kind of sit with that discomfort just that it is. The awareness of it will keep you going toward the right direction, but it is uncomfortable.”

Said Tamara: “This is a place where we need to continue moving forward and continue being explicit about what ‘done’ looks like so that it's not this thing you can't get to. Let's define what would be good enough, and then you can get to it.”

Getting to “Done” with Systems Documentation

Get Clear On What “Done” Looks Like

Have you and your team defined “done”?

On a micro level, that definition applies to what “done” looks like for any given project. On a macro level, it applies to what “done” looks like in terms of your ultimate business goals. What systems and processes would you have to have in place to deliver your products or services to the scale and quality you desire?

If you’re not clear on what “done” looks like, nothing will ever feel quite finished, leaving you and your team with a perpetual feeling of dissatisfaction or a “nagging striving.” When you have a clear definition of “done,” on the other hand, “it becomes a cycle of finishing and celebration.” You and your team can close the book on one project, relax for a moment, and appreciate a job well done.

Having a shared definition of “done” is also essential from a leadership perspective: “If you have a team and you're not explicit with them about what success looks like, you will be putting out fires, you will be intervening, you will have people stepping on toes, because there's not clarity – what does done look like, who owns each step in the process, and who owns the final result. Those are gifts. If you can give that to your people, you're letting them let go of all the potential interpretations that they may have in their heads of their idea of perfect, and you're saving yourself so much time.”

Create Standards Around Core Values

When creating systems or processes, companies often skip over the human part of the equation and head straight to listing out steps for how to complete certain tasks.

Before getting into the nitty gritty of your systems documentation, start by defining the big catchalls that would apply to how anything gets done – in other words, your core values. For example, one core value might be: “When we see something wrong, we say something.”

By explicitly laying out core values, they become a job requirement that will naturally guide how employees do their jobs from the minute they’re onboarded.

Bring in a Fresh Perspective

Sometimes the best way to overcome boss shame is simply to recognize when you need to ask for help. Help doesn’t even have to come from someone with expertise in your field – any kind of fresh perspective can do wonders.

“I think I'm always surprised that you can ask somebody who knows nothing about your business and you can get these really amazing gems of insight,” said Tamara. “Even the most unexpected people can share insights and be the key to unlock something that you need.”

By being open about our struggles and reaching out for help when we need it, we’re removing the taboos around entrepreneurship that cause boss shame in the first place. If everyone were more candid about their experiences, we would realize that it’s impossible to have all the answers all the time and that we realistically can’t run our businesses alone.

Work on Solving Your One Key Challenge

“A lot of times all of the things that are on our to-do list are distractions and our ways that we soothe ourselves, frankly, into feeling like we're moving forward or we're moving [at all],” said Tamara.

But are we actually taking meaningful action that will move the needle forward in the ways we envision?

Tamara encourages those who are ready to ask for help but don’t know where to start to ask themselves one question: what is the one thing that, if resolved, would remove everything else on my to-do list? For example, maybe it’s finding an assistant who can take care of most of the day-to-day business upkeep.

Once you’ve identified what that one thing is, it’s time to start searching for the people who can solve it for you. You may not know the right people yet, but you will find them if you truly believe they’re out there.

“I swear, that investment in energy towards where you're heading, it magically makes it work. You will move towards where you need to go,” said Tamara.

Networking can be a great way to identify the right people to help you move forward in your vision. It can initially feel awkward or burdensome to ask for help, but most people are honored to be asked for their insight or expertise – it shows respect and trust.

“Find your people. They'll help you find those people. You'll figure out the next thing. It's really hard to do it on your own,” said Tamara.

Connect with Tamara Kemper at

Listen to the show and check out the show notes for this episode for additional information and resources here.


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