Sept. 12, 2022

Why Won't They Do What I Tell Them? (Challenge #32)

Why Won't They Do What I Tell Them? (Challenge #32)
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It’s time for another leadership challenge! 

 Today, we’re looking at a real-world scenario where a leader feels they are clearly communicating their expectations, but team members just aren’t quite getting it. 

 We should warn you though, any possible solution to this type of problem ultimately involves having a conversation that could make everyone feel a bit uncomfortable. 

 On the bright side, we’ve got a whole lot of practical advice for you!

 In order to solve a problem like the one we have here, you first need to understand the reasons behind it. These could be any number of things including simply not understanding your instructions, not understanding the need—or the why— of your instructions, disagreeing with your instructions or disagreeing with your authority to give said instructions. 

 There are different ways of dealing with each possibility, but at the end of the day, people just want to be heard and know that they are supported. 

 Tune in today for helpful tips on how to navigate disagreements when it comes to giving and receiving instructions, and create a kinder, more harmonious work environment. 

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This episode was produced byPodcast Boutique.


Long time listeners of the podcast know that every so often I like to do a deep dive into a leadership challenge that’s been shared by a member of the Kind Leadership Challenge community. This week’s question comes from a conversation with one of my new LinkedIn followers. They’re a Head of School, AKA a Principal at a secondary school in West Africa, and are struggling with getting their more seasoned, and “difficult” instructors to follow instructions. This leader believes they are clearly communicating their expectations, but those team members just don’t want to do it! I don’t care where you are or who you lead, I think we can all resonate with that problem. So let’s dig into that problem, shall we? 


Welcome to the Kind Leadership Challenge, where I empower educational and library leaders like you to build a better world! I’m Sarah Clark, founder of the Kind Leadership Guild. My PhD in higher ed Leadership, my experience coaching, consulting, and presenting to library leaders all over the world, and a career working in academic libraries from the front desk to the Dean’s office taught me that leaders can transform their organizations without burning out. And now I’m sharing those same lessons with you.  

Over the next ten minutes or so, I'll share short stories and simple challenges designed to heal yourself and your school or library, so you can get back to making the impact you wish to see in your communities. By embarking on each week’s challenge on your own or in our private community, you and your team will begin growing humanely, managing effectively, and creating collaboratively, so you can build the more informed and educated world we all need.

Spoiler alert: This week’s challenge will ultimately have to be addressed with a conversation that may feel a bit uncomfortable. Fortunately, if you’re dealing with a similar situation with someone not following your instructions, we’ve got a tool for that! Mastering Challenging Conversations is a free checklist for planning, conducting, and moving forward from any challenging leadership conversation. Just go to, enter your email and start having the conversations that will impact your community for the better.


My new LinkedIn connection’s challenge with their team not following instructions left me with more questions than answers. When I realized I wanted to do an episode about their challenge, I thought about asking them for more detail on the situation and how they’d handled it so far. But then I realized that this episode might be more helpful both to this leader and to the rest of you listening if I started from this very basic scenario of team members not following instructions, explore the most likely reasons these “difficult” teachers weren’t doing what they were told, and explain what conversations you need to have with your team members the next time you’re faced with a similar scenario. 
 After brainstorming based on similar challenges I’ve either experienced or coached other leaders through, I realized the team members’ apparent resistance is likely coming from at least one of four areas. First is the most obvious but most overlooked reason: your team doesn’t understand the instructions! I’ve certainly fallen prey to this one myself more times than I care to admit. So let’s start by presuming positive intent. Ask your team members to explain to you what they think you want them to do. You might be surprised to learn that what you thought you explained perfectly clearly was in fact really confusing. If that’s the case, then you can explain your instructions again, make sure they understand them, clear up any questions or concerns, and you’re good to go!  Sometimes you get lucky, and that’s all you need to do to get them on board. Unfortunately, sometimes the problem is deeper than that.

So here’s the second and possibly most common reason that teams don’t follow your instructions. They may understand your instructions, but they don’t understand the need for your instructions. This is often the case when you’re trying to improve or change an old process, and your team might not understand the reason for the change. If you think that might be the case, then it’s time for another conversation. Rather than simply explaining why you want to make the change, ask your team about the new instructions, and what problems they see with them. After all, if you’re giving instructions, then by definition you’re delegating actions to them, and they may see problems with your new instructions that you can’t see. If they identify problems with your instructions that are in your control to fix, then fix them. If they’re not in your control, like a new regulation or rule from your supervisor or governing body, explain that too, and work with them to identify the best or at least bad way to implement the mandate. Either way, once they’ve had a chance to explain their concerns, now is the moment to explain the reasons why the instructions are as they are. And often understanding the why behind the change is all team members need in order to decide to follow your instructions, even if they don’t totally agree. But that’s not always the case, which leads me to the third scenario.

Your team members may understand your instructions, and they understand why the instructions are how they are. But they disagree with the reason why you’ve given the instructions so strongly that they are unwilling to follow your instructions. And that’s where things start getting tricky. 

Back in episode 13, when I talked about the leadership lessons I picked up during my short career as a welfare caseworker, I observed that most of the time, people just want to feel heard. I think that’s especially the case when a front line educator or librarian sees their organization changing in ways they don’t agree with, and see you, and by extension your instructions, as a symbol of that negative change. Of course, that strategic shift they dislike at your school or library is probably a mandate from higher authorities that’s out of your control. Heck, you may privately agree with your team’s concerns! However, agree or disagree with the strategy, you’ve decided that it’s in the best interests of your organization and your career to go along with the new plan that led to the new instructions. 

If this situation sounds familiar, then your best conversation is one where you ask your team members to share their concerns. Depending on how much trust and safety already exists between you and your team, it may take more than one invitation for them to really open up. Leave the door open, and really listen, so that they can feel understood. And then be frank about what is and is not within your power to change, and about the fact that they will face consequences if they don’t follow your instructions. Finally, tell them you will support whatever decision they make about whether they want to stay at the organization, if they truly feel they can’t get on board with the new plan. 

I’d love to say that’s the worst possible reason why a team member might not be following your instructions. Unfortunately, there’s one more. In my experience it’s pretty rare, and usually a symptom of deeper toxicity within an organization. But it’s real. A team member may understand your instructions. They may understand the reason behind them. They may even agree with that reason. But they don’t agree that you have the authority to give those instructions, so they refuse to follow them.     

There’s a few reasons for this. Your team member may disagree with your hiring, or have bitter feelings around the circumstances behind your hiring. They may dislike your boss or your boss’s boss. They may have political or philosophical objections to following your lead. Whatever the reason, it’s ultimately irrelevant. You are the leader, whether or not they agree with that reality. And as a leader, you have a professional and frankly moral obligation to do your best by your team, as long as your duty to your team isn’t overridden by a higher moral obligation (in which case you should resign, but that’s a topic for another episode). 

At this point it’s time for a very uncomfortable, but very simple conversation. Sit down with your resistant team member, and make absolutely sure that their noncompliance is not due to the first three issues we discussed. If their noncompliance isn’t due to those first three issues then tell them the hard, simple truth. If they refuse to do what you need them to do, they will face consequences up to and including termination.  And put them on whatever version of a performance plan or warning system your organization has, sooner rather than later. One insubordinate team member can poison a whole organization and shatter a leader’s self worth. So you need to nip it in the bud. Get backup from HR and your superiors if you need to. And if your organization won’t give you backup, then start looking for a new job.

Well, that was a cheerful note to end this episode on! I shared that fourth scenario not because you’re likely to experience it (because most leaders don’t). However, you need to have a plan in your back pocket just in case, because in the unlikely event it does happen, you probably won’t be thinking clearly. That’s also part of why I offer 1:1 coaching as part of the Kind Leadership Academy, because no leader should ever have to face a situation like that without support. But in any case, you do have the ability and power to help your team follow your instructions more effectively, and I hope this episode gives you a blueprint to coach your team to new levels of excellence.

Thanks for listening and for taking action to become a kinder leader. If you found this week’s episode insightful, give the show a rating or review—or even better, share this episode with your fellow leaders!  Never doubt that day by day, you’re building a better world, even if you can't see it yet. So until next time, stay kind now.   

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