How To Have Challenging Conversations. Tips From Organisational Science


Key takeaways


  • Don’t choose between a “hard sell” and a “soft sell”. Neither of these things work, neither does the “feedback sandwich”.
  • Become more “open to learning”. Increase the validity of information, respect and commitment to set these conversations up properly.
  • Use 7 components to guide challenging conversations. Not quite a “how to” script, but pretty close – do these things and your “challenging conversations” might become a whole lot less challenging.


How To Have Challenging Conversations. Tips From Organisational Science



Many of the challenges we face in schools come down to people management. For most problems in education, it’s easy to find an “answer” – something that’s been shown through empirical studies to achieve your goal.

This sets leaders up with a “change agenda”, something they want to see done differently by people to improve student outcomes. The hard part isn’t coming up with the change agenda; it’s making sure it fits the context of your school and that the people who will need to carry the agenda out, actually will.

When we looked at How to Lead School-Wide Change That Sticks, we saw that leading change doesn’t always lead to improvement. In this post, we look at more of Viviane Robinson’s work, this time drilling down to the conversation-level looking at her Open to Learning framework as discussed in this great, and free, background paper.

Much of Robinson’s work is housed in organisational science, specifically the work of Chris Argyris (the guy who brought the world things like double-loop learning, the ladder of inference and organisational learning). Let’s have a look at what this science can tell us about having tricky conversations.

Don’t choose between a “hard sell” and a “soft sell”


“Challenging conversations” happen all the time in schools. Usually, they arise when one person needs to talk about the quality of another’s performance. This might be during a formal performance review, but a lot of the time it’s not – it’s just in the daily work of school leaders working with teachers on curriculum design, delivery, assessment and student management.

These conversations arise when one person (usually the leader) is pursuing a change agenda with another individual (usually the teacher). This might be adherence to a policy change, coming on-board with a school-wide practice shift, or talking to someone about some element of their practice not meeting the leader’s expectations.

These conversations are hard because leaders often feel they need to choose between having a “tough” conversation and “picking their battles” by skirting around the edges of the performance issue. Some leaders shy away from these conversations, mostly because they believe that having a difficult conversation with someone is going to be too stressful, cause too much conflict or undermine goodwill.

This is known as the “task/person dilemma” – it arises when leaders feel they must choose between the pursuit of the change-agenda and protecting their relationship with the person they’re speaking with.

This results in leaders choosing between two popular, but ultimately ineffective options – the “hard sell”, and the “soft sell”. Guaranteed, you’ve used both at one point in your career. They seem effective, but don’t really work. Let’s have quick look at why

The hard sell

In the hard sell, the leader prioritises the change-agenda and accepts that doing so is going to hurt the relationship. In the hard sell, the leader declares what they see as an educational problem and asks the teacher to fix it.

For example, consider a leader who has just observed a lesson which was miles away from the school’s instructional model, using the hard sell the leader might say something like:

“I’m really concerned that I didn’t see use of the instructional model there. I’d like you to read through the model’s documentation, and then talk to your Learning Area leader about how to use the instructional model for a class like this. Come back to me once you’ve done this and let me know the changes you’ll make to your lessons”.

This approach gets the message across but it’s likely to provoke defensiveness from the teacher, which is unlikely to support lasting practice change. Ultimately, the leader may have just damaged her relationship with the teacher without getting any closer to implementing the change agenda.

The soft sell

The soft sell sees the leader prioritise the relationship over the change agenda. When people use this approach, they often say things to themselves like “I’m picking my battles”, or “I’m building goodwill to draw on later”. In our example above, the leader might say something like:

“So, tell me about how you’re using the instructional model in your lessons? When I observed your class, I could see that students were really enjoying the activity they were doing. How do you see the instructional model fitting into your classes right now?”


Rather than declaring her concerns about the teacher’s non-use of the instructional model, the teacher invites the teacher to reflect on the model in her lessons, as well as offering “ceremonial praise” on the level of student engagement. The teacher feels good about this, but it’s not very good for their teaching in the long run and it doesn’t address the perceived educational problem that the leader is harbouring.

Neither of these strategies are effective. The task / person dilemma isn’t resolved with either and the issue the leader has concerns with is likely to persist.

From the Background Paper:

“In the soft sell strategy, the leader discourages debate by failure to disclose her evaluation of the [issue observed]. In the hard sell strategy, the leader discourages debate by assuming the truth of her views. Neither strategy will produce the type of conversation that is necessary to reach a principled agreement about the quality of [teaching] and about whether change is needed.”


Become More “Open to Learning”

Hard and soft sells aren’t effective ways to have challenging conversations, so what works? The shit sandwich? It doesn’t work either – which you’ve probably worked out if you’ve ever received one.

The major thing that needs to change is the leader’s assumption that their evaluation of performance is correct. Instead of making this assumption, the leader should spend more time validating their evaluation of performance with the teacher. This allows the two parties to reach agreement of the quality of performance and what needs to change.

Three values underpin conversations that do this well:

1. Increase the Validity of Information

Treat your views as hypotheses that need to be confirmed. Rather than assuming your evaluation of performance is correct, spend more time canvassing the thoughts, opinions and reasoning that underpin this evaluation. Having canvassed these views, you also need to seek feedback and disconfirmation from the teacher (yes, disconfirmation check that things don’t fit, not just that they do.)

2. Increase Respect

Give people the benefit of the doubt. If you start with the premise that you’re talking with someone who is well intentioned, interested in learning and capable of making a valid contribution to the discussion, you’ll be much more likely to have a productive conversation. A lot of this comes down to deep listening as well as sharing the control of the conversation with the other person.

3. Increase commitment

Make sure you’re working towards shared decision making. To do this you want to share the problem, and the problem-solving process with the other person. This allows you both to “own” solutions and work together in implementing and monitoring their execution.

So, if we return to our not-using-the-instructional-model example above, a more open-to-learning way of approaching this may be:

“During the first half of my observation today, I noticed that the students hadn’t been asked to complete a lesson starter, and that the lesson didn’t seem to have any formal “explicit instruction” phase, students just received the task and started working. The starter and instruction are really important parts of our instructional model, so I thought I should tell you that and invite you to talk me through the way you’d structured that lesson”

In this example, the leader doesn’t hide their concerns about the structure of the lesson, but neither do they assume they’ve made the correct assumption and simply tell the teacher what to do. Instead, the leader provides their view, the grounds on which it is based and invites the teacher to help them check their view is correct.

Use 7 Components to Guide Challenging Conversations

Pulling this all together isn’t easy, especially with the emotional vulnerability associated with conversations about performance. While there isn’t a step-by-step “how to” guide for these conversations, there are some fundamental components that underpin effective practice.

1. Describe your concerns as your point of view

Here, you want to explain your concern without assuming it is the reality. Don’t hide your concern in a leading question and expect the other party to reveal it. State it clearly and transparently.

Examples from the Background Paper:

“I need to tell you about a possible concern I have about…

I think we may have different views

I realise this may not be how you see it…

I’m really disappointed in the artwork because…”



2. Describe what your concern is based on

If your concern is not “the reality”, then you need to provide the other person with the basis for your opinion. Giving the grounds for your view puts you in a better place to check its validity with the other person

Examples from the Background Paper:

“The reason why I was concerned is…

Yesterday when I was going past your corridor I heard…

If I’m right it’s the third meeting you haven’t been able to come to… “



3. Invite other’s point of view

This part is crucial. If you want to get the other party on board with improving the situation, you must find out what they think about the change agenda. Try to approach any differences in opinion as opportunities to learn, rather than opportunities to persuade. You want to be like a therapist here, listening and digging into the views you hear, not like a prosecutor, trying to refute, twist or ignore opinions that don’t match your own.

Examples from the Background Paper:

“Pause and look at the other person or say:

What do you think? You haven’t said much so far…

Do you see it differently?

I’m sure there is more to it than what I’ve said… “



4. Paraphrase the point of view and check
Paraphrasing is a great way to keep emotionally connected to the conversation, but also to check you’ve heard and understood things properly. Here you want to confirm that you have been listening properly by asking the other person to confirm that what you say back matches their understanding.

Examples from the Background Paper:

“I got three important messages from that…Am I on the right track?

You’re shaking your head. What have I missed?”



5. Detect and check important assumptions
You want to spend some time identifying and checking important assumptions. Take stock of the important things underpinning the conversation, canvass these, and check the other person agrees. All of this helps you agree on what information is valid, and what is not (rather than you each assuming your own view is the valid one and doing this – I love how they look at at each other afterwards like it didn’t hurt. It hurt.)

Examples from the Background Paper:

“What leads you to believe that the children aren’t yet ready to read?

What would be an example of that?

What other possibilities are there?

How would we know if we are wrong?

What evidence do you have about the effectiveness of this math package?”



6. Establish common ground
This doesn’t necessarily mean that you completely agree with one another. An important part of this conversation is pointing out clearly, in the steps above, the things you don’t agree with the other person on. But you do want to establish some common ground, because this will give you a way of moving forward.

You might determine common ground by both agreeing that the status quo isn’t ideal (even if you don’t agree how to fix it yet), or you might agree on the best next steps for resolving differences. Either way getting on the same page on something is important for keeping you both working together, it helps you pursue both the relationship and the goal.

Examples from the Background Paper:

“We both agree this is unacceptable as it is…

It sounds like we see the problem the same way…

We both want…but we have different ideas on how to get there…

We see the cause of the disruption differently but both want to do something about it…”



7. Make a plan to get you both what you want
You’ve done a lot of work by this point and now it’s time to round it out with the planned next steps. What these are isn’t that important, but having both parties agree on them is.

Examples from the Background Paper:

“How would you like to learn more about the new curriculum requirements…?

OK – you talk with your teachers and let me know next week how they explain the results.”



Key takeaways


  • Don’t choose between a “hard sell” and a “soft sell”. Neither of these things work, neither does the “feedback sandwich”.
  • Become more “open to learning”. Increase the validity of information, respect and commitment to set these conversations up properly.
  • Use 7 components to guide challenging conversations. Not quite a “how to” script, but pretty close – do these things and your “challenging conversations” might become a whole lot less challenging.