10 Steps to holding tough conversations with your team

Matthew Bradburn
People Collective
Published in
7 min readJan 19, 2023

We’re back!

One week in and we reached 1094 subscribers on our Linkedin newsletter (subscribe here), and we’re very grateful so many of you are interested in what we can share from our collective learnings 🎉 🥲

Yesterday I had my first induction into the Maven accelerator programme, as we look to take our learnings global. Next week, you’ll be able to sign up for our 6 part course for managers who want to challenge themselves to become GREAT leaders. We’ll share the link then.

For now, I wanted to share our learnings on Crucial conversations. Now you might ask, what on earth is a crucial conversation? Are you just using some management BS 💩… Well we think not. We think that reframing tough conversations as crucial conversations, removes the negativity and emphasises the need for action, FAST!

Staying on the theme of 10 practical steps, we’ve put together “10 steps to effectively hold crucial conversations”. The focus being the questions YOU need to ask YOURSELF before holding them. No-one said this would be comfortable 🛋

What are crucial conversations?

Crucial conversations are conversations we anticipate to be challenging because of how we think things might turn out. This might be when you need to tell an employee they’re not meeting expectations, or if there’s some drama on your team that needs to be sorted out. Even just saying no to a request can be a crucial conversation when heightened emotions are at play.

They can be emotional and tricky, but they’re important to have if you want things to improve. Below are some steps to help you prepare for hard conversations specifically around poor performance/behaviour:

1. Recognise and act early to address issues

We often put off hard conversations because they feel uncomfortable, but addressing issues early will always prevent bigger problems down the road. You’re giving your team member a chance to make a change before it becomes too late to fix. You’re also taking action, which is one of the BIGGEST failings of mediocre managers. But we get it, it’s hard. One way to combat avoidance is to consider the cost if the conversation doesn’t happen vs the discomfort of having it now.

  • Is it impacting the rest of the team? Consider performance, morale, and behaviour.
  • What message does my tolerance of this behaviour/situation say to the rest of the team?
  • Am I setting a precedent?
  • Will this person stop doing this if I don’t ask?
  • What will happen in 6 weeks if I don’t address this now? Will the conversation be worse?

2. Acknowledge the reality without judgement

We often will take our view of a situation as fact, but really we view everything through the blinkers of our own biases, experiences and assumptions. Taking a moment to consider the reality of the situation objectively as possible can help you to step away from the idea of it as a “challenging conversation” and help you start with empathy.

  • What is fact and what is opinion?
  • Where have I made assumptions or jumped to conclusions?
  • Is there anything else that might have played into this that I’m not considering?
  • What part might you have played in creating or continuing this situation?

3. Reframe the conversation

Reframing the conversation is a great trick to change how the situation will be viewed by both people by considering how you can both walk away with the best possible outcome. It’s especially helpful when there’s a lot on the line and emotions are high. It takes take, but start now. Look for the great outcomes and possibilites.

  • What is your ideal outcome?
  • What is their ideal outcome?
  • What do you want to avoid happening?
  • What do they want to avoid happening?
  • How can you both walk away happy?

4. Check your own mindset and emotions

You might have an idea of how you think the conversation will play out, or how the person will react. But really you have no idea of what the actual response will be. However, by going in with a fixed idea of outcomes, you can actually create the scenario through your body language and responses. Taking control of a conversation starts with taking control of your mindset and emotions.

  • Are you feeling, how might that come across?
  • How do you think this conversation is going to play out?
  • What else could happen instead of that?
  • How do you react in tense conversations? How could that create issues?
  • What might be a better response?
  • What will you do to manage any tricky emotions that come up when talking?

5. Prepare what you’d like to say (but don’t script it!)

Being prepared is great, but trying to map out the conversation is only going to leave you feeling lost when the other person doesn’t stick to the script that they didn’t know you were using.

  • Use a structured feedback model like OIPS to prepare what you want to say
  • Use observations and data where possible
  • Word your thoughts with open questions to avoid making accusations
  • Consider how you might pause the conversation if you need to

6. Don’t try to win

If the conversation centres around convincing the other person we are right, it means that someone has to be wrong. Leading with curiosity and avoiding conclusions and emotions can help to foster a more productive and respectful conversation. When people are more focused on learning from each other, they may be more open to considering new perspectives and ideas.

  • Why?
  • What do you think of…
  • Would you agree?
  • What do you think the best way forwards is?

7. It’s OK to take a break and come back to discuss more at a later date

Not everyone takes feedback in the same way and some people might need time to digest. Checking in to see if that person wants some time is an excellent step to moving forwards.

  • Would you like some time to process everything and meet again tomorrow?
  • I’d love to know what you’re thinking right now, but if you want some time I understand
  • I’ve thrown a lot of information at you and understand it might be overwhelming, what do you need?

8. End with clear actions and a plan on when you’ll meet next

You want to make sure that everybody leaves the conversation with a shared understanding of what you discussed and is clear on what needs to happen in order to move forwards. Remember to check their understanding of what you’ve said to avoid any gaps!

  • Be very clear on what needs to happen next and by when
  • Agree when and how you’ll next check-in
  • Make sure you understand what support they need from you and act on it
  • Don’t be afraid to spell out the consequences that will happen if they don’t make a change

9. Reflect and build self-awareness

It’s a great practice to take some time after a crucial conversation to reflect on how things went and what you might do differently in future to avoid similar situations.

  • What went well and what didn’t?
  • Is there anything you could have done differently to avoid the situation happening?
  • How will you avoid this in the future with other team members?

It can be great to get that person to summarise the conversation and the next steps and send it to you. This gives them accountability, creates a written record and also means you can check if they’ve understood you properly.

10. Remember that it isn’t only your responsibility

It can be easy to feel guilty and hold all the responsibility if things don’t work out after a crucial conversation. Just remember that as long as you’ve tried to support that person and treated them with respect, it’s not all on you to have fixed any issues. If someone isn’t the right fit, it’s usually better in the long run for everyone for them to move on.

“As much as others may need to change, or we may want them to change, the only person we can continually inspire, prod, and shape — with any degree of success — is the person in the mirror.” — Kerry Patterson, Crucial Conversations Tools for Talking When Stakes Are High

Thanks for reading, would love thoughts on the content, any insights you might have as well!

A reminder that we can help build your team capability through our accelerator programme:

“The programme was great, best of the ones I’ve done so far in my career. 5*” A recent attendee from Vortexa

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Matthew Bradburn
People Collective

Father first and then Founder of www.peoplecollective.io - your modern people and org consultancy