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Caught in the Middle: How to Navigate Middle Leadership with Integrity

Updated: Mar 18



middle leader caught in a web

I have been in some sort of middle leadership for 14 years now and I have recently had conversations about navigating this with integrity and what it takes. Last week I had the opportunity to teach a Professional Development session for Middle Leaders at my work (a large international school in Singapore) and I wanted to take the opportunity to share those thoughts and ideas here too.


Whether volunteered, voluntold or vacuumed into that position - whatever has placed you as a middle leader, that is exactly what you need to be doing: leading from the middle. If we were to consider structure in a linear way, you are caught between management above and team below. It is easy to lean more in one direction or the other. If you are pursuing higher levels of leadership, you may find yourself leaning more in that direction. If you are caught up with the gossip and complaints of your team, you can lean more toward them. Consider the structure as a web (in the PD session I use streams of toilet paper as a physical example). If you lean more in the direction of your leaders, it is all too easy to tear the toilet paper between you and your team, causing a disconnection between team and management. Likewise, if you lean more toward your team, the tear can come between you and management. And so it is quite an art to be able to stay in the middle, keeping everyone connected, preventing any tears. It requires a high level of integrity and a significant amount of energy and self control. Which way do you find yourself leaning?


In order to be able to maintain the "middle" ground, it is important for us to be clear with how we communicate upward and how we communicate downward. (Please remember, "upward" and "downward" is in a linear structure of leadership in an organisation, rather than hierarchical). But before diving into how to navigate this, it is necessary to deliver one piece of difficult information that is important for framing Middle Leadership: It is not about you. Middle leadership is never about you, the middle leader - it's not your organisation, your vision, your ideas... but it is your job to serve someone else's organisation, someone else's vision and someone else's ideas. Of course occasionally, with healthy collaboration, the ideas may have come from you, but remember they have been given permission from your leaders.



Relating Upward


I believe that relating well upward helps middle leaders to lay foundations for a healthy working relationship. I also have seen that it is possible to disagree without causing disagreements. Coming up are some tips that I have found are helpful in building a strong working relationship with your leaders.


  1. Get Organised As middle leaders, we are a spaghetti junction of information, tasks and expectations. As these things: information, tasks and expectations are placed on us, we have the responsibility of dealing with these without breaking the web upward, or the web downward. Those in a similar situation to me (where I have my own job and role, AS WELL AS a middle leadership role), will find that this is essential to being able to relate upwards well - this is the foundation upon which the rest sits. Getting organised may look different for each of you, but for me this is by having a rolling email inbox and by having a clear and regularly updated list. My email inbox has only got the things in it that I need to address. Everything else goes into a selection of folders, so I know where to access it again should I need. Systematically at the end of each academic year (I am in education), I will archive that year and start fresh, with only a handful of ongoing folders still remaining. Currently I only have 18 emails in my inbox - all of which need action in the next few days. I also have a simple google document with check boxes that I share with a team partner and our leaders. That way, everyone can see at all times what we are working on. What is the one thing in which you need to be better organised today?

  2. Be Proactive Whatever your leader needs the most is probably what you should focus on the most. In my experience, it can be really obvious what your leaders need OR it can be really tricky to find out. I have had the benefit of some of my leaders framing a season with "this season we will be focusing on..." and that allows me to write a post-it, etch it onto my board or to set myself a reminder for 2 weeks time to see how well I am fulfilling this focus. Once you know the focus, or the things that are needed, look for opportunities to communicate it to others, or even fulfil it in one way or another. Proactive members of the team are awesome - they contribute with such value and are reliable. As middle leaders, we should aspire to be proactive. Think of your current project or equivalent. In what ways can you be proactive today?

  3. Ask Questions If it is not clear what your leader is after, ask them! Recently, I was asked to do a task that I felt needed more evidence before I acted. I didn't ask questions quickly enough and my superiors were frustrated with me and by the time I asked them the questions, the answers were already laced with frustration. If I asked sooner, we could have avoided a tense moment. Questions can be asked for clarity, for deepening your understanding, for confirming your understanding. Remember - tone is often harder to read in an email and so if in doubt, look for a 5 minute check-in so that you are super clear. After one or two of those short face-to-face conversations, you would have built an understanding between you and your boss/leader/manager that they know you are wanting to help the cause, and not questioning their authority. Is there anything you need clarifying at the moment?

  4. Provide Headlines Particularly in larger organisations, it is easy to feel like your leaders do not know what you are doing and we often feel the need for our superiors to know what we are up to. In this case, I'd say a headlines email is a perfect thing to send once every week or two. A headlines email is just a quick 3-5 bullet point email that lets your line manager know the headings of what you have been working on. If they require more, they can ask and you could provide more in depth "articles", but headlines are a great way of showing what's been going on. Is there anything you feel would be good to share with your supervisors/managers/leaders at the moment?

  5. Appreciate Openly It makes a huge difference to know you are being appreciated by the people you lead. It helps to clarify purpose and identify successes. Some feel like this is "kiss a$$ing" but I believe it is valuable. Of course, be genuine. Remember, appreciation is not given with the aim to receive it back. These little open appreciations are great for building a strong working relationship and can work as a catalyst for leaders to know what about their leadership is working particularly well. Is there a leader you can appreciate today? What specifically have they done that has helped you?

  6. Practice Humility This is a principal for life to be honest, but I have seen it so many times where we as middle leaders can get it wrong and begin to stop having a posture of humility, a willingness to learn and to place others before ourselves. Sometimes you just need to back down and let go, in order to allow momentum to build up within your team. As middle leaders, we are at advantage that there is always someone above you to be able to learn from. Humility allows the learning to happen with ease. How have you been carrying yourself lately? Abrasively? Arrogantly? Maybe it's time to back down and practice humility.

  7. Bleed Up Frustrations and disagreements happen always - it's part of being human. But you can really damage a team by complaining downwards. You can break trust of a team and you can see it all crumble down. So bleed upwards - go and see someone in leadership who can help listen, action and even mediate if needs be. Is there anything you need to stop sharing downwards? What might you need to discuss with someone in leadership?


I hope these are helpful tips - I have found them to be and I can give specific examples of where these have really helped me to maintain my integrity as an employee as well as my own personal integrity.


As identified earlier, middle leaders, by the nature of our role are in the middle (I know, it's obvious!) and so as well as Relating "Upward", we need to be able to successfully Relate "Downward" too. Here are three tips for relating downward.


  1. The Tea Scale A friend of mine, Ben Wattley, is a medical doctor and he shared this thought with me a number of years ago and it has never left me. As a young doctor, he realised that the nurses always made cups of tea for the doctors and never the other way around. He decided that he would try to tip this balance and start to offer cups of tea to the nurse team, always ensuring the scale was balanced. He even talked about how some of the nurses felt awkward about this sometimes, but that it was important to know that they were valued. What is your Tea Scale? I always try to get around to my team and encourage them, thank them for something specific and appreciate them. Recently I have tried to wash up someone else's dirty plates or cups in the sink in our shared work room too, leaving them post-it notes to wish them a great day.

  2. Delegation I'm not sure where I heard it first (and so credit is due somewhere!) - only 20% of delegation is actually delegation, the remaining 80% is for accountability and feedback. Sometimes we think delegation is done when we ask someone to do something, but that's not the case. I'll give you a real example from my life as a middle leader in a large international school. I regularly receive reports of student behaviour and oftentimes this would require follow-up: emails to parents; student meetings and so on. This is the sort of thing I might delegate. - I email the teacher asking them to follow up with the student and their parents by a certain date (delegation). - I ask them to cc me (accountability). - I ask them to let me know how it went (feedback). - I also set myself a reminder for when to follow up should I have not heard from my team member by a certain date. Of course, the WAY we delegate is important too. Delegation isn't devaluing the task, it is empowering the team member. So help them to feel that way. Accountability places the value on the task - it needs to be done well. And feedback places value on you as the delegator.

  3. Flexibility As middle leaders, we must resign to the fact that this is one of our requirements - a non-flexible middle leader is one who will find the job and relating to others hard as a result. For those who struggle with flexibility, there's good news - you can plan "flexible time" - a short 10-15 minutes in the day to assign to anything unplanned that may need your attention. In middle leadership, everyone at some point will be crying for your attention and to create space so that it doesn't feel like an emergency that you need to "squeeze in" somewhere is helpful. At other times, you'll need to prioritise things quickly to be able to fit in everything that you need to do and at other times, you'll need to be prepared to throw everything out of the window, because something else has come up.


If you are able to apply these little tips, I believe they can help you as a middle leader. I believe it can help your organisation and that each of these will make for a more cohesive team.


Please let me know in the comments whether this has been helpful for you and if you have tried any of these tips or have any of your own!

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