What to do when an essential leader resigns mid-year
New Year’s Day: a blank slate, a fresh start, a day to take stock and set direction for the year ahead. For over 40 years, I enjoyed this federal holiday as the rest of the world did–often on vacation, sometimes at home, usually reading books and feeling full of resolve about the year ahead.
As an educator, I had never worked a New Year’s Day in my life. Not only was it a federal holiday, it also fell squarely inside a two week break: sometimes with only a day or two left to go, sometimes it was about the halfway point of break. I have often used time over breaks to get caught or work on new projects, but never, ever on New Year’s Day
Until January 1, 2020, when I got a text from my Middle School Principal saying “Hey, can we talk today?”
My spidey sense tingling, I had a bad feeling. Sure enough, he resigned–to add insult to injury, effective immediately. While this wasn’t entirely surprising (or to be honest, unwelcome), the timing was frustrating. Really–you couldn’t wait to resign until the federal holiday was over?! (I later learned that he waited until the New Year so he could “claim with integrity” he worked through 2020. How did I discover this? When he applied for a new job and the hiring manager called me to ask about his performance for the school year! Still irritated by the way in which this whole situation went down, I made sure she was clear that literally the only thing that he did in 2020 at my school was resigning and cleaning out this office, not serving through the school year as his resume implied. Needless to say, he did not get the job. Karma keeps track.)
At the start of another New Year, I thought I’d offer some perspective and advice on what you can do should you have a mid-year Principal resignation–or that of any other key senior leader who is the only one in their position. While the particulars of this are around resignation, the following steps are also useful in the event a Principal needs to go on leave suddenly, or is ill.
First, allow yourself to feel your feelings. There are likely a lot of them–I know I was irate and had a whole lot to say and think about not only how this went down but the past few years. While you can’t dwell in your feelings forever, you do have to let that energy out in order to move forward productively. I called a friend and let off some steam, and after that went to a spin class. I had to discharge that negative energy and work through that feeling of betrayal enough so I could get to a place where I could be productive in figuring out what to do.
Once you’re in a good-enough spot with that, make a list of all the reasons why this is an opportunity. As former mayor of Chicago Rahm Emanuel once said “Never let a serious crisis go to waste.” Look, no one wants a mid-year Principal resignation–you may not have wanted it to happen, at this time, in this way–but it did, so you might as well make the best of it. I realized quickly that I could accelerate some of the changes that clearly were necessary at the middle school by cutting out the middleman–in this case, a leader who was hypersensitive to people’s feelings and shied away from having conversations with adults that held them accountable. Presto change-o, barrier removed! Keeping that perspective helped me have a better attitude moving forward and think about how to manage the situation to help get us closer to the mission and vision.
Your solution will likely have two parts: interim and permanent. Figure out your timeline. How long each period of time will be will depend on the specifics. Is there someone strong internally? There should always be a thorough interview process so even if you suspect that person could be the right candidate, you’ll still need a solution for a few weeks while you conduct an accelerated process. In my case, I knew that the middle school was in need of continued turnaround. There was no one internal who would be a strong candidate, and mid-year talent searches in my experience had usually been a disappointment. I quickly decided that there would be an interim solution through the end of the school year, and we would launch a search for the permanent candidate a few months from then, in the spring. Having decided that, it allowed me to focus on what was next with a strong sense of clarity.
With the timeline established, it’s time to start getting more granular. Look at the role being vacated. Hopefully, you have done some clear roles and responsibility codification and building out team division of labor so you can refer to those documents now as you try to wrap your arms around the role. You are trying to figure out what the nitty gritty of the next few weeks or months looks like–what has this person been doing? What will they need to do?
Make a list of what they would normally do, and categorize each one as “Must Do”, “Nice to Do”, or “Okay to Pause”. Dump out everything in your head you can think of and put it in one of these categories for now.
As you categorize, be really judicious about what has to get done. What this step does is make sure that you are able to keep the trains running at your organization, and you are also shaping the expectations for who will be taking over parts of the role. Maybe you are lucky and have a retired principal you know who could come in and act as Interim for a period of time, but in the event you don’t (I didn’t), this may need to be temporarily distributed among your existing team and you want to make sure that since you are adding to existing roles, it’s what truly needs to happen. It can be hard to put “researching the new science curricula” on hold, but it may have to be paused since existing team members are likely taking on some additional responsibilities, and this may not be essential.
As you categorize, there may be some areas that you are unsure about. I sometimes would have a “figure this out in a week” category, once I had a more solid sense of the lay of the land. After you have finished categorizing everything on the list, go back and go through each responsibility line by line, thinking “Does this HAVE to be here? What will happen if this doesn’t get done?” Be relentless in ensuring that only the most important tasks as in the must-do category.
Now, think about who on the team can possibly take on some of this work. Be generative in who could help with solutions: are there contractors you can bring in? Network team folks? A trusted former employee who went to grad school but likely has sometime to help with a few things that may be in their wheelhouse? The less this work lands on 1-2 people, the better–it’s more sustainable for everyone. Picking up a few extra responsibilities for a short period of time feels do-able; taking on someone’s job entirely in addition to your own feels overwhelming even to the most accomplished person.
Until now, this work has been done on your own. Part of leadership is having a plan when a crisis develops. This is your time to think through and consider all the elements at play. At this point–once you have a clear sense of what may be coming, you may want to bring in a trusted thought partner. I knew I’d want to bring in our high school principal–both as a thought partner for what I was missing and for her perspective–as well as our COO, who was in charge of HR and would be able to pressure test what I was thinking. Because I was not trying to ruin their New Year’s, I didn’t reach out to them until the next day–no need to spoil their holiday. In addition to talking through where I saw the scope of work going on an interim basis, we also talked through communicating this news with the team and families and communities, and how to do so in a way that would inspire confidence rather than fear. By the time we were done talking, we had a solid plan of what was to come and how we’d break this news to the team. I had also discussed with the COO at a high level how we could stipend people who were taking on significant additional responsibilities, to acknowledge this additional work in some way.
The last thing I had to do was really take a hard look at my schedule the next few weeks and rearrange it. Like it or not, this was a huge, mostly unanticipated change for the middle school, one of 2 schools in my network and as the Chief Executive and Academic Officer, there would be fallout that I would be responsible for helping to contain. In this case, I was personally going to assume many of the responsibilities: I don’t always recommend this, but in this case there were a number of factors that made me think it was the best choice. I had to look at my responsibilities and decide what could be paused for now, as I took over as Interim Principal, what others could help with (like fundraising or board work), and what I would still need to make time for even while I juggled both. This also meant personally making sure that I would be able to take this on: arranging my childcare around this, for example. As a divorced parent at the time, I happened to be on one of the two weeks a year I had away from my kids when I got this call. That year, the 1st was a Wednesday: I had been planning on going back to Chicago on Friday, but instead I drove home on Thursday. By Thursday afternoon, I had communicated this to the COO and high school principal, called the Middle School admin team–who was most impacted–and was able to get some planning time on the calendar before the team came back on Monday for PD.
There are many fun parts of leadership, and this is usually not one of them. However, being able to help lead the organizations through periods of change is part of why you’re in charge!
Does any of these resonate with you? Would love to hear any comments below on advice you would offer when a critical leader resigns mid-year.
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