Ruth Penfold-Brown


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The biggest thing that we fail at within our companies and teams, and frankly wider relationships, is our ability to have challenging conversations. 

Yep. Really. And especially if we want to create a culture of innovation. 

A challenging conversation could be talking to someone about a change that impacts their role, it could be trying to get a promotion or pay rise, or it could also be sharing feedback with someone. We avoid them because our brains are trying to avoid pain and suffering, but without these conversations, we lose so much. 

Challenging conversations are an essential part of growth. By definition of creating something different, you are going to be changing things to get there, biggest of all being our mindsets and perspectives. If we don’t get good at working together to change things, we don’t end up changing anything at all. 

How I learnt to have challenging conversations

I learnt the importance of having challenging conversations first of, by doing not it. I worked at Shazam and was excited to codify our culture for the first time. We obviously had a culture but it had never been mapped out properly which made it harder to hire amazing talent sometimes, but also meant that we could be different things culturally at different times. 

It actually took me 3 attempts to make it happen. The first attempt I avoided challenging conversations, so didn’t take the leadership team on the journey with me and instead, worked with an external partner then excitedly presented the results in a doomed ‘tah dah’ moment (side note: I have since learnt that most projects created for a group of people in a vacuum that doesn’t include them, will fail more often than not haha). Unsurprisingly, they rejected it outright, feeling like things already worked well in the business. 

The second attempt came on the back of a spike in attrition, where I managed to take the leadership team on the journey as I now had data around why this was so important, as I had learnt what they needed, but I failed to create the groundswell amongst the team itself. I had covered the group I thought I needed to, but failed with everyone else. 

My third attempt, I had managed to really surface all the resistance that existed to the change and was able to take the whole business with me and create something meaningful for us all. 

Change takes time, commitment and determination to make things happen, but it makes the end result (if you get there) even more meaningful. So here is my 3 step formula for forcing yourself to lean into a challenging conversation. 

#1 Write a script

For a challenging conversation; think of the one most important message you need to convey and write it down. This is your focus, above all other things that come up in the discussion. Your one thing you must share before you, or they, leave the conversation. 

Something powerful happens when we write things down and don’t just carry them in our heads. It’s also worth brainstorming potential objections ahead of the conversation to make sure that you are as prepared as you can be to take people on the journey with you. 

Is it a conversation that you aren’t sure what will come up with encouraging yourself to speak up in a meeting, allow time to brainstorm the following:

  1. Are there any issues within your team you are aware of, that it is worth surfacing with the wider leadership team? 
  2. What are the things you/your team are currently working on? 
  3. Based on what you understand of the challenges the company is facing, what are the things within your team/business area that are most relevant. 

For example, I was Chief People Officer, so if there was a challenge around Sales, there was almost always a People element to that that I was able to comment on, even if I wasn’t able to add value to the overall discussion otherwise. 

If the conversation is a feedback conversation, it is also important to consider the fact that you are only witnessing the world from your perspective, from your ‘truth’. There may be some objective facts about the situation, but what goes wrong is that we often fail to separate the narrative from our own perspectives. 

A truth might be:

This wasn’t delivered on time

A perspective might be:

You are incapable of delivering things on time

Just like you can only share your perspective, the same is true for your listener in reverse. So in reality, in these conversations, whilst there may be universal hard truths, the interpretation of those truths is often only perspective and therefore, it will help to choose your words from a place of inquiry rather than a statement of fact. 

My model for feedback is CISSA:

  • Context of the feedback plus give 1-2 examples, make it specific and prepare for it.
  • Importance of the feedback, the impact on you, the team, the organisation, gives the reason why they should care about this.
  • Space to hear their take on the feedback; do they need time to go away and do this? 
  • Shift needed to counteract the feedback (if at all); what is the outcome you wish to see?
  • Agreement; make the agreement of what is going to happen next together, whatever that might be.

#2 Rehearse and plan

Just like giving a presentation, make sure that you take the time to rehearse ahead of time. Make sure that the first time that you read your script isn’t live. This is where your ONE MESSAGE is crucial. This is your focus, above all other things that come up in the discussion. Your one thing you must share before you, or they, leave the conversation. 

Part of building a good dynamic with someone involves truly attempting to get to know them and understand what does and doesn’t work for them. It is also essential to try to be in the right energy when the conversation happens. I  like to think about that across three lenses:

  • Right attitude: To communicate effectively you have to care about the person you are giving the feedback to. That doesn’t mean that you have to know them super well, it could actually be your first meeting, the key is about caring enough to understand (and take responsibility) for the imprint that you leave on the humans you interact with day to day.
  • Right energy: Particularly with feedback, it’s worth checking in on your own energy and intention. Is the thing that you feel you need to share honest? Is it necessary? Is it constructive? 
  • Right time: Choose a time and place that suits the other person. If you already know them, what do you know about how they like to work. Try to also find a time that works for you, where you can create the space to feel as calm as possible and be prepared for the conversation.

Planning also means we are creating accountability with ourself to actually go ahead and do. 

#3 Have the conversation

You’ve prepped, you’ve planned, you’ve rehearsed, now is the time to deliver your perspective and engage in a conversation with the other person. 

Prepare to give them time in the conversation (and beyond). If they are not yet aware of their impact, they may feel attacked (irrespective of their behaviour and potential impact). Remember this: It is NOT your role to rescue them. If they get upset and need to leave the conversation, give them space. Reach out either a few hours later or the next day to schedule a follow up meeting.  

Final tips for speaking up

Ultimately, when it comes to challenging conversations: 

  • Get comfortable with discomfort. Remember fear will never leave us and challenging conversations are an essential part of what it means to lead others and learn to self advocate. When we shy away from them, no one wins. You have to build an environment where you can be straightforward but also not erode safety. 
  • Invest in your relationships by building bridges intentionally, especially with those that feel different to you, be honest about the difference rather than pretending it isn’t there
  • Be a human with your team, let them know you as a whole person. Inclusiveness looks like being okay with falling, learning, and being wrong, you need to set that example by sharing your own failings/learnings. Be warm, friendly and supportive.
  • Share the situation as openly as possible, when we speak in half truths it creates mistrust, because humans always know when someone is holding something back. Use inspiring language and communicate well.
  • Finally, make life easier for yourself by telling your closest teammates how you like to receive feedback, and ask them the same question. Taking control of how you like people to give feedback to you will allow you to create the support you might need to get better at taking it. 
About the Author

I help Founders and People leaders to build and scale purposeful businesses, whilst scaling themselves at the same time.

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