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Focus More, Don’t Work More: 9 Leadership Lessons From My First Year as Head of School

Posted by on November 29th, 2023
Posted in Blog, Coaching, Independent Schools   

Every leader needs a good coach, and I am privileged to coach Dr. Anna Moore, Head of The Howard School in Atlanta, Georgia. We have worked together since the start of her first year, in which she was both new to her school and new to being the head of a school. 

It was a big professional jump and one she was ready for. Howard School is lucky to have her confident, effective leadership.

I asked Anna to share what she learned in her first year at Howard that can help you reach your own goals, feel more confident, and be more effective.

Jennie: First, why have a coach?

Anna: Leading an organization is demanding emotionally, intellectually, and physically. Imposter syndrome tends to be pretty common, especially among women. Although the majority of teachers are women, as you move up in school leadership, men occupy most of the seats. The strains of leading can result in you feeling you have nowhere to turn to for counsel to help you develop as a leader and advance your organization’s goals. 

Even with mentors and cohorts of other leaders to call on, you can often experience being overwhelmed by the responsibilities of leadership— despite looking like you have it all under control. Coaching provided a unique and protected space for me to do the personal work of my own leadership development. This has made me a stronger leader.

Jennie: What benefits do you get from coaching?

Anna: I actually was a little skeptical about coaching overall. I have a Ph.D. in Clinical Psychology with a specialization in Neuropsychology, so I wondered how valuable coaching could really be for me.

Having you as my leadership coach made the difference between managing imposter syndrome and building a fully authentic leadership style that allows me to be more confident and effective. My team is stronger and my school is stronger because I am being coached.

The private space to explore any and all issues that arise with a professional coach – without judgment or fear of impacting my reputation – is one I want for all heads of schools and nonprofit leaders. 

You noted that it is successful people who actually hire coaches. My leadership style and confidence quickly and exponentially grew as a result of being coached. Group settings with other leaders are often about shared friendship and venting. There’s value in that, but it’s less healing, productive, or transformative. 

Being coached helps me be accountable in a different way, and it’s a place where I have a chance to fold in personal things that might impact my professional life. It’s not therapy. But addressing any dynamic that’s pushing in or shaping me and having the ability to think it through cognitively helps me structure my day or week while I manage that reality.  

You pose questions that help me see things I might not otherwise. I feel more prepared in a constantly changing world and work environment. 

Jennie: What are the most important lessons you learned about leadership and confidence in your first year as Head of Howard School?

1. It’s lonely, so don’t go it alone.

Even with professional allies, which I do recommend, having a coach helps you restore and re-energize and not feel so overwhelmed and isolated.

2. Leadership is deeply personal.

We can all read books on leadership, but having a coach allows me to think about leadership for myself, not the “right” answer or someone else’s formula. Coaching has allowed me to deconstruct my definition of a leader. I was initially externally driven. I saw goalposts and things I wanted to achieve as a leader, but that is NOT the same as being leaderful.

Working with you is deeply iterative, and that was a surprise to me. We went far deeper than ‘What’s your leadership style?’ It was intimidating at first!

3. Your team matters.

Several months into coaching, I changed my LinkedIn profile tagline to “Leading leaders for the sake of students.” This may seem simple, but it represents a transformation in my thinking. 

I was given lots of well-intended advice as I moved into the role of Head of School, including “Don’t make any big changes early on.” But as I worked with you to name my core values and understand more of what my school needed from me as their leader, I realized that having a team grounded in trust with a shared sense of respect and purpose was non-negotiable for me – and best for the school and our students.

I wasn’t hired to lead a school or an institution; I was hired to lead people. The team we’ve put in place now is strong, committed, and being nourished on their own leadership journeys.  

So to leaders reading this, I say: Honor your path and the needs you see in your school. Build the team and the resources you need to do your best work. This is why you were hired – to lead! Coaching for me created the space to find my best way forward for the sake of my school, and the coaching I’ve since gotten for my team resulted in an immediate uptick in our flow, with a more authentic and open dynamic we can all feel. 

4. Books and workshops are no match for weekly examination of my leadership.

Every week, I continue to refine my sense of self as a leader. With workshops and other professional development, I leave with several nuggets of good information and some key takeaways. The difference with 1:1 coaching is that you think about who YOU are as a leader. It’s DEEPLY personal. 

5. Stay out of the weeds.

I am more effective than I was early on. I move more quickly now. I’ve been able to let go of some of the weeds. It took confidence to do that, and the more I do so, the more I see how leaderful that is.

6. Ask for what you need.

I’m now able, in those moments when anxiety or fear takes over, to find that inner voice and strength to say what needs to be said. So, my advice is to ask your board and team for all of the tools and support you need as a leader, especially when you’re new. And ask for a coaching budget for you and others on your team.

Remember that it’s actually successful people who seek coaching, so ask for the money for it right out of the gate. I was surprised by the amount of transformation in a short time. The return on investment for me and my school happened really quickly. 

7. Focus more, don’t work more.

It’s easy to work around the clock. That’s stressful, exhausting, and ultimately not good for you, your colleagues, or your organization. Now, I have a better ability to trust I am working hard enough so I can be with my family or relax. I do that more fully, and then I am more effective at work and a better partner.

8. Bring your personal values to the job.

Being honest about what matters to me – and acting on it – creates confidence. Knowing my values helps me be authentic and make decisions more easily. 

When I have a struggle or question, turning to my values helps me make decisions (small and large) that are best for me, the people involved, and the school.

When personal and professional values don’t align, you feel “icky” and often inauthentic. That chips away at your confidence, and people around you can feel that. 

9. Negative mental self-talk holds you back.

We all know that we have some negative self-talk going on during stressful times. But I did not realize that I (and all of us) have that negative self-talk going on all day long. The work we did, including learning to use the Positive Intelligence™ framework to quiet that negativity, has had a profound impact on me. I recommend it to everyone and have seen a profound impact on me and my team.

How will you up your leadership game in 2024? Happier professionals are more effective, elevating your ability to meet the moment for your mission.


Jennie Winton is a Founding Partner of Mission Minded, a 25-year marketing veteran sought for her expertise in branding nonprofit organizations, and a one-on-one leadership coach.

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