I shared previously HITO evolved from a solo operation to a team of ten employees and how we implemented systems to create a business that could operate without my constant presence. While those systems were crucial, they were only half of the equation. The other half—perhaps the more important half—was people.
As a single mother by choice preparing for the arrival of my son, I knew that even the best systems would fail without the right people implementing them. Here’s how we approached building a leadership team that could thrive during my absence and beyond.
One of the most transformative concepts in my business journey came from Dan Sullivan’s book “Who Not How.” The premise is simple but powerful: Instead of asking “How can I do this?” successful entrepreneurs ask “Who can do this?”
This shift in thinking was particularly crucial for me as I prepared for motherhood. With limited time and energy, I needed to focus on finding the right people rather than trying to do everything myself or creating elaborate systems that no one would follow.
Implementing this philosophy meant:
1. Identifying key functions that needed leadership during my absence
2. Finding people with the right skills and values to fill those roles
3. Investing in their development before I stepped away
4. Giving them real authority to make decisions
This approach required me to let go of the idea that I was the only one who could do certain things “the right way.” It meant accepting that others might take different approaches than I would—and that different didn’t necessarily mean worse.
Another crucial framework came from Gino Wickman’s “Traction,” which emphasizes having the “right people in the right seats.” This means not only finding talented individuals but ensuring they’re in roles that align with their natural abilities and passions.
We implemented this by:
1. Creating clear accountability charts that defined each role’s responsibilities
2. Assessing team members against our core values to ensure cultural fit
3. Evaluating whether people were in roles that matched their strengths
4. Making tough decisions when someone was in the wrong seat
This process revealed that some team members who were excellent in their current roles weren’t suited for leadership positions. Others had leadership potential but were in roles that didn’t allow them to exercise it. And in some cases, we had talented people whose values simply didn’t align with where we were heading as a company.
One of our most painful but educational failures came with a hire I made to oversee operations and client relationships before my maternity leave. On paper, he had an impressive pedigree and spoke a great game during interviews. He seemed like the perfect solution to my impending absence.
Looking back, there were numerous red flags we chose to ignore. His arrogance surfaced in subtle ways during the interview process. He occasionally dismissed team members’ input. He spoke about past employers with a hint of disdain. But we were in a time crunch—my due date was approaching, and I felt immense pressure to find someone quickly. So I overlooked these warning signs and made the hire.
The consequences were swift and severe. Once I had my son and was absent for just a few weeks, he began making irrational decisions that negatively impacted the company, our clients, and even his own professional standing. He implemented processes that violated compliance standards. He made promises to clients that we couldn’t ethically fulfill. He began reshaping our service offerings without proper consideration of regulatory requirements.
What made the situation worse was his dishonesty. When team members raised concerns, he dismissed them. And when they eventually reached out to me directly (thank goodness they did), he lied to my face when confronted. I had to gather evidence of his actions while simultaneously caring for my newborn son—not exactly how I had envisioned spending my maternity leave.
This hire nearly caused permanent damage to our reputation—the reputation I had spent years building. We had to take immediate and decisive action. We parted ways with him and then took full accountability with our clients. We contacted everyone potentially affected by his decisions, transparently explained what had happened, and redid projects to ensure they were fully compliant, often at our own expense.
This failure taught us several invaluable lessons:
1. Never ignore character red flags, no matter how impressive the resume. Technical skills and experience are necessary but insufficient. Value alignment and integrity are non-negotiable, especially for leadership positions.
2. Pressure is a poor decision-making partner. The time crunch led us to lower our standards and rush a critical hiring decision.
3. Team culture is your best early warning system. Our established team members recognized the problems before they became catastrophic. Their willingness to speak up saved us from even worse outcomes.
From this experience, we completely revamped our recruiting process. As I mentioned in my previous post, we created a comprehensive interview guide that standardized the entire hiring process. We designed interview questions specifically to assess alignment with our core values. And we implemented our “hell yes or no” rating system—if anyone on the interview team wasn’t enthusiastic about a candidate, we passed.
We also built in mandatory “cooling off” periods after interviews to allow time for reflection away from the candidate’s persuasive presence. And we added specific reference check questions designed to uncover the exact issues we had missed.
This systematized recruiting process dramatically improved our hiring success rate. It also ensured that even when I wasn’t involved in hiring decisions, the team was selecting people who would uphold our standards and vision.
Most importantly, this failure reinforced that people decisions are the most consequential decisions we make as leaders. A bad hire—especially in a leadership position—can undo years of hard work in a matter of weeks.
One of the most important lessons we learned is that “right person, right seat” isn’t a one-time assessment. People grow, roles evolve, and the business changes. Someone who was perfect for a role a year ago might no longer be the right fit today.
We implemented regular evaluations to assess whether:
– People who were once in the right seat were still in the right seat
– Team members who were developing needed new challenges
– Roles needed to be redefined as the business evolved
This ongoing evaluation process helped us identify when someone who was once the right person in the right seat had become either the right person in the wrong seat (requiring a role change) or the wrong person in the right seat (requiring a difficult conversation or transition).
Finding the right people was only the beginning. We also needed to develop their leadership capabilities before I stepped away. This development process included:
1. Shadowing opportunities where future leaders could observe my decision-making process
2. Graduated responsibility with increasing autonomy over time
3. Regular feedback sessions to discuss what was working and what wasn’t
4. Leadership training through books, courses, and external coaching
Perhaps most importantly, I created safe spaces for future leaders to make mistakes while I was still available to help course-correct. This allowed them to develop judgment and confidence before they needed to operate independently during my maternity leave.
One of our biggest challenges was achieving full buy-in to our operating system and accountability structures. When I stepped away for maternity leave, the leadership team wasn’t yet fully committed to holding each other accountable.
In retrospect, this was partly due to timing—we had only been implementing our operating system for about a year, less than half the recommended time for full cultural integration. But it was also because we hadn’t spent enough time on the “why” behind these systems.
Team members understood the mechanics of our operating system but didn’t fully appreciate how these accountability structures protected the business and ultimately their own success. Without this deeper understanding, some accountability measures fell by the wayside during my absence.
This taught us that people need more than instructions—they need context and purpose. When we later reinforced these systems, we spent more time explaining not just what to do but why it mattered.
Building a leadership team isn’t a one-time project—it’s an ongoing journey. Even after returning from maternity leave, we continue to refine our approach to finding, developing, and retaining the right people.
Some key lessons from this continuing journey:
1. Values alignment trumps skills. We can teach skills, but values are deeply ingrained.
2. Development takes time. Rushing leadership development leads to insecure leaders who make poor decisions under pressure.
3. Different doesn’t mean wrong. My way isn’t the only way, and sometimes team members find better approaches than I would have.
4. Accountability requires relationship. People accept accountability from those they trust and respect.
5. Everyone needs coaching. Even the most talented leaders benefit from ongoing guidance and feedback.
Building a strong leadership team required significant investment—of time, energy, and financial resources. There were moments when it seemed like it would be easier to just do things myself rather than develop others to do them.
But the freedom this investment has created has been worth every minute and dollar. It has allowed me to:
– Be fully present with my son during his early months
– Return to work with boundaries that protect our time together
– Focus on strategic initiatives rather than day-to-day operations
– Build a more valuable business with multiple layers of leadership
Most importantly, it has allowed me to model for my son what it means to lead with purpose and balance. He sees a mother who is passionate about her work but equally passionate about being present for him.
