What to do when you don’t get picked. How to be seen, picked, and promoted as an aspiring ed leader.

Michael Lomuscio
The Startup
Published in
9 min readDec 13, 2019
Photo by Nathan Dumlao on Unsplash

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Many of us have been there: a leadership position is opening up or the Head of School announces that a new committee is forming to tackle this or that issue. It looks like a wonderful opportunity and you know that you are a great fit. You want to be picked.

Maybe you were hoping that someone would think to ask you. Maybe you inquired about the work, hoping that it would lead to an ask. Or, maybe you explicitly expressed your interest in the work and requested to be part of it.

Whatever the case may be, you weren’t picked.

As an aspiring leader, that can really sting. It dents the ego and has the potential to launch you into a psychological spiral of negative self-talk.

The key to turning your disappointment into productive action is to stop the negative self-talk and replace it with the truth. Use this experience to help you be better prepared for the next opportunity. The most effective way to do that is to reflect on what senior leaders are looking for and how they pick people for leadership positions and working groups.

What are senior leaders looking for?

Senior leaders have a lot on their plate. They are responsible for the health and sustainability of the school as well as the wellbeing of students. Producing results with excellence is key. A highly functioning senior leader knows that this means having the right people in the right positions.

When it comes to matching people with positions, there are six traits that senior leaders must consider. Relative to the open position, the right person must be:

  • Motivated
  • Results-driven
  • Equipped with the needed set of skills
  • Creative and innovate, but understanding of what is feasible and realistic
  • Focused on excellence
  • Unflappably positive

These six traits compose your Leadership Value Proposition (LVP for short). Your LVP is a measurement of the value that you would bring to the table if you were placed in an open leadership position.

Reflecting on your LVP can help you better understand why you weren’t picked for a particular leadership opportunity and how to better position yourself to land future leadership positions.

Motivated

It is a miserable experience for a senior leader to have someone on their leadership team who doesn’t want to be there. Senior leaders want people on their team who clearly WANT to be there.

We all want to feel seen. It’s a great feeling when your boss approaches you and says “I’ve got a special project and I know that you’re the one for the job!” But often in real life, that simply isn’t how it happens.

The sobering truth is that people aren’t really thinking about you all that often. It’s not because they don’t like you, they are just thinking about themselves and the whole host of challenges they are tackling at the moment. Unless something brings you to mind, it’s unlikely that you are going to be the first, or second, one that they think of.

Hence, if you want to be picked, you need to explicitly express interest. It’s not enough to hope to be picked. It’s not enough to hint at wanting to be picked “Hey, I noticed that you’re putting together a committee for XYZ. It sounds like really interesting work.”

It can feel a bit forward or uncomfortable approaching a senior leader and directly expressing interest in a position. However, that is the easiest and most direct way to let them know that you are highly motivated to be in the position and to do the work.

You need to muster up the gumption to explicitly tell your senior leader that you are interested in the leadership position.

How will you communicate that you are highly motivated to do the work?

Results-driven

Senior leaders need people on their team who are focused on producing results. Independent schools, as well as most organizations, are full of critics, self-proclaimed experts, and armchair philosophers who like to sit around criticizing and pontificating about the decisions made by senior leaders.

Critiquing is easy. Consistently delivering quality results under resource and time constraints is hard.

Senior leaders need to be confident that you are able to consistently produce quality results, in a timely manner, under a variety of changing constraints.

How will you communicate that you are results-driven?

Equipped with the needed set of skills

It’s tempting to interpret being passed over for a promotion with senior leaders not believing that you’re leadership material, but frequently that is not the case.

In addition to being motivated and results-driven, senior leaders need the people on their teams to have very developed skill sets. The best leaders hire for their weaknesses. For example, if a senior leader is great with fundraising, but doesn’t have expert-level knowledge with admissions, you can bet that they are going to hire the most skilled director of admissions that they can find. This means that senior leaders are on the lookout for domain experts.

So what’s the take-away?

If you are a domain expert, you need to find humble, non-aggressive, ways to display your skills and the value that you would bring to the table.

A senior leader doesn’t know what they don’t know. If you have a well-developed skill set that you believe would add value to your school, you need to make it known.

It’s important to find an authentic way to do this. The use of the words “humble” and “non-aggressive” is intentional; the only thing worse than presenting yourself as a showoff or know-it-all would be presenting yourself as incompetent.

Here are some ways you can display your knowledge and skills:

Set up a meeting with a senior leader to express interest in taking on a special project in a particular area. For example, if you have a background in writing grants and want to display your advancement prowess, you could ask the current director of advancement if you could take on a side project of helping to write a grant for the school. If you have experience in curriculum development, you could ask your division head if you could work on creating a new elective course.

When you ask to take on a side project it shows that you are motivated, you get the opportunity to show that you are results-driven, and you get the chance to display your skills.

If your first side project goes well, try taking on another. After you have successfully completed a few side projects, you can approach your senior leader again to express how much you have enjoyed them. Let your senior leader know that you would like to pursue more of this kind of work. Ask them what kind of opportunities might exist for you to continue doing this kind of work.

What if I’m an aspiring leader, but don’t have expert level knowledge in a specific school domain?

Shift your focus from getting a promotion to developing your skills. The best way to gain domain knowledge is to dive into an actual project.

If you’re doing something that you’ve never done before, learn as much as you can, do research, and be hungry for feedback.

Stay motivated and work hard. Over time you will develop the expertise necessary to stand out as an expert.

Creative and innovate, but understand what is feasible and realistic.

Independent schools are often in the paradoxical conundrum of needing to innovate to stay relevant while also honoring and remaining true to school history and traditions.

For example, many schools located in cities are constrained by physical space, which comes at a premium and makes expansion difficult. For some schools, the constrained physical space promotes a high-collision environment that embeds itself into the culture of the school. Innovations to solve the space problem would need to retain the human connectivity that these schools have come to value.

Another example comes from rural boarding schools. Some rural boarding schools are constrained by their distance to other schools. They often want to offer their students a robust and competitive athletics program. However, their distance from other schools makes this difficult. Many boarding schools highly value the unique focus on academics that they can offer their residential students. Hence, any innovative solutions to solve the athletics problem would need to account for maintaining a quality academic program.

As they say, “necessity is the mother of invention.” There is an intimate relationship between constraints and the quality of creativity. To develop meaningful solutions to independent schools’ most pressing challenges, innovators must have an understanding of the resource limitations and constraints under which their organizations operate.

You must first see the box in order to think outside of it.

Senior leaders must see that you have a deep and wide perspective on your school and that you are able to creatively take on the unique challenges that it faces.

There are two pitfalls that I often see aspiring independent school leaders fall into when it comes to creativity and innovation

  1. They let their field of vision get hyper-focused on the small part of the organization that they interact with daily. This results in losing sight of the big picture and makes it hard for them to offer creative solutions that are feasible.
  2. They hyper-focus on the big picture at the cost of losing sight of the on-the-ground constraints that need to be considered.

In order to show that you are a creative innovator, you must show that you understand the unique context of your school and the varying levels of constraints that need to be considered when developing feasible solutions.

Focused on excellence.

This is often the hardest aspect to coach in an aspiring leader.

At the end of the day, you have to execute with excellence.

This is similar to the popular adage, “slay your lane.” Essentially, you need to do great work in the position you were hired for, whatever level that might be. You have to produce high-quality results, and do it consistently. Let your consistent character and the quality of your work speak for you.

This doesn’t mean that you’ll do everything perfectly. I’m a huge fan of agile development workflows, sprints, learning from failure, the lean start-up model, and iterative cycles of design thinking. I’m not saying that you shouldn’t expect to fail and learn from it.

However, failure cannot be your modus operandi when you are leading an organization. You need to perform with excellence. Make sure that you are putting your best foot forward. Ask questions when you are unsure about something. Admit when you need help or have made a mistake.

You need to demonstrate to senior leaders that you are someone who can be counted on to do great work.

Be unflappably positive.

Finally, be a great person to work with. Have a relentlessly positive attitude. Don’t gossip. Don’t engage in the rumor mill.

This doesn’t mean that you avoid highlighting challenges or expressing your concerns. But it does mean being part of the solution rather than the problem.

Leaders establish the tone and culture of their entire school. High functioning leaders are aware of this and work to build a positive culture. They simply cannot allow anyone, regardless of their level of talent, to infect that culture with illness.

Like infections, toxic organizational cultures can develop quickly and be hard to get rid of.

Building and growing a positive school culture is one of the chief responsibilities of a senior independent school leader. If you are an aspiring leader then it has to become one of your chief concerns as well.

I have heard many senior leaders express the sentiment, “It’s easier to train a positive person than it is to fix the damage caused by a highly trained toxic individual.”

So, be an unflappably positive person.

Conclusion

As you aspire to be picked for a leadership position, reflect on your Leadership Value Proposition and how you are displaying it. Be intentional and strategic.

  • Show that you are motivated and results-driven.
  • Use side projects to develop and demonstrate expert-level skills and knowledge.
  • Study the forest and the trees to boost your capacity to innovate feasible solutions.
  • Execute your current role with excellence.
  • Be a positive person who contributes to building an amazing culture.

Finally, don’t forget to be yourself and to have fun. Leadership is too much work to not enjoy the ride.

About the Newsletter

This newsletter provides resources for aspiring independent school leaders to accelerate their growth. It goes out a couple of times a month with content and Saturday mornings with short curated recommendations for books, articles, podcasts, etc. If you like this newsletter, forward it to friends!

About the Author

I’m a career independent school educator and researcher. I utilize my background as an applied mathematician and data scientist to generate evidence-based insights for independent schools and the Ed research community. I believe that in order to stay relevant and find innovative solutions to the challenges facing independent schools, we need to internally develop leaders with excellence and intention. I’m a fierce advocate for aspiring independent school leaders and dedicate time to providing you with resources to accelerate your growth.

You can connect with me via FullstackEducator.com, LinkedIn, and Instagram. Subscribe to the Fullstack Educator Newsletter to get resources for aspiring independent school leaders sent directly to your inbox a few times a month.

© Michael Lomuscio 2019

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Michael Lomuscio
The Startup

I'm a career independent school educator and researcher. I currently serve as the Director of STEAM Programs at a PreK-12 international boarding school.