Emotional Leadership Mistakes I’ve Made as a Small Business CEO

Seven years in, people ask me if Ellevated Outcomes has turned out differently than I envisioned – or if our success has been a surprise. My answer is… not really. But you have to remember: this isn’t the first business I’ve built. So, when I started Ellevated Outcomes, I knew the technical aspect of how to build a business. BUT (wait for it), I’ve certainly made mistakes along the way. There is a huge facet of being a small business CEO that I wasn’t prepared for. And it is by far and away, the most excrutiating part: emotional leadership.

Eighteen months ago in NY, over 6AM coffee talk while our spouses slept in, my friend Tony said to me:

Your personal limitations will become your organization’s limitations.

Ouch.

So today, I’m going to be oh-so-personal and share 3 mistakes (out of mannnnnnny more) I’ve made over the past 7+ years. And you’ll notice: none of them have to do with anything “business-y.” They all have to do with people. Ask any CEO of any size business, and they’ll agree. People are the hardest part. And I’ve learned: that to nail your emotional leadership game, you need: clarity, groundedness, and personal agency.

Before I get into it, I need to state a preface that’s important to this piece. So much conversation today is around emotional intelligence leadership. And that is very, very important. What I’m going to discuss today isn’t that. It incorporates it, but it’s not the same.

Here’s why: I’m speaking to creative, small businesses. And in my experience in the market, considering others isn’t the issue. CEOs in our market are dying to consider their employees’ feelings. Sometimes to a fault. So, it’s one side of the coin, but it’s just that: one side.

The complement to EI is what I’m dubbing (self) emotional leadership. The common thread in the mistakes I’m about to share are when I got confused about myself and my stance, and then I wavered. In that wavering I compromised my own sense of self; and it caused confusion. And the sources of each of these? My personal insecurities and fears…

Mistake #1: Lessening My Standards

Since the age of 18, I’ve been in and out of therapy, as a recovering perfectionist. I’m lucky for this catch so early in life and that I’ve now had multiple decades to work on it.

I share that backdrop as context to tell you: I’m sensitive when others critique my standards, attention to detail, and the level of excellence I expect from myself and others. Throughout my life, these comments have come at me from many angles: family, friends, and employees.

After I started hiring a team at Ellevated Outcomes, I was repeatedly told that my expectations were “too high.” At home, my husband critiqued my management style, citing the same. In response, I softened my standards of others and became scared of setting and holding expectations. The result was: people underperformed, and when I gave them feedback on it, they became angry – because I hadn’t been clear on what our non-negotiable standards were.

What I Now Do Differently:

These days, I’ve found my way (back) to: my standards are Ellevated Outcomes’ standards. They are what gives our brand panache and makes our Outcomes what they are. It’s not personal; it’s business. Or perhaps in this case, it’s personal and it’s business. And I’m unwavering about it. After all, when you’re a creative or service-based business, you must deliver a consistent brand and client experience.

Example:

Recently, I asked someone on the team to complete a body of work within their responsibilties, and I asked them to run it through peer review before presenting the final to me. When I received the deliverable, I was disappointed. New Julie ; ) took this as an opportunity to clarify expectations on our standards. So during monthly 1-1s, I raised it with each person who was part of the process, keeping it simple, factual, and a teaching moment:

“I need to share some feedback on xx. I’ll be careful in delivering this; because I understand your role in the process, and you were not the owner. However, as part of peer review, you signed off on it, so you need to know: this isn’t up to Ellevated Outcomes’ standards. It’s below the caliber of work I expect anyone to put in front of me, and we would not put this in front of a client. Next week, I will complete the final, and when I share it back, please put the two versions side-by-side and make note of the differences. And of course: ask me any clarifying Qs about the gaps.”

In this category, I have learned: Do not meet people where they are. Teach them how to meet you at the standards you expect.

And if they don’t have the capacity to fulfill their role at the company’s standards, you need to make a hard decision.

Mistake #2: Not Explaining our Culture Clearly Enough

You’ve heard me talk about our values before: integrity, honesty, inclusion, and abundance. A few years ago, an employee gave me this feedback on her last day at our company:

“You talk about abundance and generosity being our values… but that has not been my experience here.”

As you can imagine, this feedback initially stung (and bravo to her honesty!) but it quickly turned into a huge aha. (Of all my insecurities – and there are plenty – generosity is not one of them).

The “so what?” was: “We have different definitions of generosity.” It made me realize the same for every facet of our culture: responsibility, feedback, empathy… others will have different definitions than I. We’re all a product of our own experiences.

What I Now Do Differently:

Now, whenever an employee has an experience in our company that’s put them in the learning pit or been different from their expectations, we make time to talk about it and really dig into why. My growth is: I don’t revert and change the thing to eliminate the adversity. Instead, I coach them through thinking about it critically so that we can articulate the gap between our respective perspectives. From there, I take note of their POV and do my best to incorporate it into explanations with them and others, moving forward.

Example:

Someone recently told me that their onboarding was much harder than they expected. Initially they framed it as a me-issue, mentioning “two different Julies.” Instead of getting defensive (growth!), I provided some prompts, to help them reflect further, in a more fact-based way. When we dug into it a few weeks later, the conclusion was: “Actually, you did clearly describe how on-boarding would feel. But I thought, ‘That won’t apply to me.’”

Though this was a phew! moment, I still did my own internal feedback looping. Following that, in conversations I’ve had with people in our hiring pipeline, I’ve doubled down on how learning pit-y on-boarding can feel in our company (you learn a lot).

Recently, when describing this to someone, she just nodded along, yes-ing me. If we speak again, I will circle back and directly say, “You didn’t ask me any questions when I described this to you. That tells me you weren’t really listening, or you don’t understand what I’m saying. Should we try again?”

Mistake #3: Not Differentiating between CEO & Middle Manager

This was a 2024 Q4 lightning-strike moment. Out of the blue, it dawned on me: most people don’t want a CEO managing them. They want a middle manager in that seat. This was such a blind spot for me, because I’ve been reporting to CEOs or very senior executives, since 2012. And I’m forever grateful for this career-changing experience. I was motivated by the hard work, learning how they thought, and growing into their expectations of excellence. How I felt wasn’t in the equation.  

At Ellevated Outcomes, we have monthly 1-1s, where, on a scale from 1-5, I rank each employee on their performance versus my expectations, and they rank me.

The clap of lightning was: no one’s ranking me on my CEO job. No one gives a f***, ha! Others will assume you’re running a financially viable business (most people are not; but that’s for another day). They’re ranking me on how I make them feel, each day, as their manager. The value of a middle manager came into clearer focus for me.

What I Now Do Differently:

Now, in dialogue, I try to separate these roles verbally. I’ll say, “wearing my manager hat…” “wearing my CEO hat…” Also, there is some emotional acceptance of knowing there are going to be periods where I’m disliked because I’m making CEO decisions, and I’m the manager of the person it affects. It can be messy – especially when our business is at a temporary stage of me wearing both hats. I need to be fluent in both roles and able to roll with the (literal-figurative) punches of making tough CEO calls and protecting/nurturing my people as their manager.

Example:

It’s no coincidence that our strategic objective for the year is to reach the final stage of Ellevated Outcomes able to run and grow without me in the manager seat.

After all, your personal limitations will become your organization’s limitations.

Final Thoughts

So at the seven-year checkpoint, I conclude with you: emotional leadership is by far the most challenging part of being a small business CEO. It requires self-awareness, clarity, and immense personal agency. The biggest mistake I’ve made in these examples – and many more – is reacting. Trying to change myself, in response to what others want.

I’ve learned, and finally have confidence that: whatever you’re looking for, is looking for you too. You won’t be for everybody, and everybody won’t be for you.

And even with the people who are for you(r business): there will be conflict, tough conversations, and mistakes. Peace and feeling good all the time is not the goal.

But having a clear and confident stance on your own emotional leadership means that you remain steadfast. You mess up, learn, and communicate. And perhaps you change your approach. But you don’t change you.