How to have a meaningful conversation with your team. (And why you should.)

Having a team meeting where you're honest and truly listen to each other can yield great results. It’s not always easy to do, so we asked business leaders about their experience of facilitating meaningful conversations with their teams.

Photo by Dylan Gillis on Unsplash

When was the last time you had an honest and meaningful conversation with your team?

A few weeks ago we asked 60 business leaders from a range of small, medium, and large organisations a series of questions about their experience of this with their teams.

The responses showed lots of common issues that leaders face when working with their teams, but interestingly, a few immediately pushed back: “What do you mean by a meaningful conversation?” they asked. 

So first things first.

What is a meaningful conversation?

A conversation with your team is meaningful if it nudges along your understanding - of each other and the situation - as well as influencing you in a significant way.

The conversation could be on anything from aligning on vision or goals, clarifying a key message, working out a new way of doing things, or deciding what to do next. 

What’s important is that a meaningful conversation requires an honest discussion - where you all feel safe enough to share your truth, really listen to each other, and allow the full meaning of what each other says to come out - so that everyone feels heard and understood.

Even better if there’s some tangible impact and beneficial change as a result, moving you all forward towards what matters.

Why a meaningful conversation with your team is important.

Having meaningful conversations with your team gives people an opportunity to share ideas, and the thoughts and opinions they might not have the chance to voice otherwise. 

This is particularly important in the workplace, where a lot of communication happens digitally, and most conversations revolve around the practicalities of day-to-day work.

​Encouraging a deeper and honest dialogue with colleagues where you all really listen to each other and feel safe to share what you really think and feel, helps build relationships, resolve tensions, and can promote a new kind of collaborative energy and fresh thinking.

In the busy day-to-day of projects and deadlines we don’t always make the time to have these kinds of discussions, but meaningful conversations can also help pave the way for increased productivity and better connections between people, which leads to more collaboration and delivery of better work as a result. 

And if you don’t find out how people really think and feel, your team could under-perform, especially when the pressure is on.

What happens in practice?

Let’s say you have some action to take or a tricky challenge to solve, and you want ideas and input from your team, to find out what people think and feel, and get buy-in.

You arrange a meeting hoping to have real and honest dialogue, to harness the intelligence and creativity of your team, and to connect and talk beyond just reading words in an email or on a screen. 

But we’ve all been in team meetings where people didn’t really listen to each other or share what they really think, so you didn’t gain any new understanding, and no progress is made. 

When we asked business leaders a series of questions about their experience with meaningful conversations with their teams, there were common themes that emerged:

1. What’s the biggest frustration you find in trying to have meaningful conversations with your team?

When business leaders told us about their experience, these were the common frustrations:

• Quiet vs loud voices
  Several leaders expressed their frustration that the same voices always speak up, so they don’t get to hear a full range of opinions.
  
  At the same time, a common complaint was that some people don’t speak up at all - either because they are generally quiet, find it difficult to interrupt, or they’re afraid of poking their head above the parapet in case they get shot down.
  
  
• Not listening
  Another frustration was of people not listening to each other, perhaps because of personality clashes, and instead they talk at each other, “so it’s not a dialogue where new understanding might emerge.”
  
  
• Being negative
  Several leaders mentioned the challenge of negative team members: “some people are always negative or are unwilling to change - which is tiring, and brings everyone down.”
  
  
• Resistance to change
  A couple cited team members' resistance to change as a frustration, including very honestly, their own resistance. “It's so easy to fall back into habits, and the safety zone of what feels controllable.”
  
  Another said that the team found it hard to shift away from the same way they’d always done things, and had the challenge of “convincing them that simply by doing more of the same that we had always done in the past was not going to lead to a different result.”
  
  
• Purpose / engagement
  Having an engaged team with a shared purpose was mentioned by a few leaders - both as a strong positive when everyone was aligned - and a frustration when they’re not - when a team member doesn’t have the same sense of belonging and purpose "they can be resistant to ideas and don’t make the effort to interact.”
  
  
• Growth challenges
  Several leaders talked about the impact on conversations of a rapidly growing business: “as the team grows, managers become more stressed as they struggle to manage their own workload and the team,” and the effect on the team of new starters: “it’s a challenge maintaining our real selves with new team members - trust needs to be there so we can have honest conversations.”
  
  
• Busyness
  Being too busy to have proper conversations was also cited by several leaders: “when you’re fire-fighting or under a lot of pressure, the day-to-day anxieties trump strategic conversations, and you don’t make the time to meet, and communication suffers.”
  
  
• Leadership
  They also talked about the importance of clear leadership to make sure meaningful conversations happen, because without it, “the will may be there but without strong leadership which gives ‘permission’ for time to be spent on this," this often doesn’t happen.
  ​
  Similarly when leaders were involved in something else and hadn’t empowered others to do it, or when no one else had responsibility for arranging it, "it doesn’t happen.”
  
  
• Diaries and locations
  A common challenge was the difficulty of getting a date in the diary when everyone could get together in one place. If not, what happens is you “share updates and info with small groups of people at a time, then information gets mis-shared, and gossip and chinese whispers start happening.”
  
  And finding the right forum: "is it team meetings or operations boards, or after work for drinks or in one-to-ones?”
  
  It’s especially an issue with remote team members. “when the team is spread across several locations - it’s hard to keep in touch and agree actions.”
  
  
• And lastly,
  ​The challenges of getting the team to have the conversation doesn't end there. As one head of department told us, “regardless of the conversations that happened in the team, little changed in the organisation as a result!”
  ​

2. What tips do you have for bringing your team together?

---

When we asked the business leaders what they've learned from trying to bringing their teams together, and for some tips on how to do it, this is what they said:
​

• Open and collaborative
  Things that don’t work include team meetings where people feel unsafe, because they're put on the spot or are undermined in front of colleagues. "Better to have an open and collaborative relationship if possible."
  
  
• Sharing of pains and positives
  What does work is being honest, and sharing the pain as well as the positives. "I would work harder sooner to create this kind of culture," admitted one leader.
  
  
• Directing not managing
  The transition from managing a team to inspiring a team made all the difference to one leader. "The moment I started directing them rather than managing them, they excelled and felt empowered. It freed up lots of my time to focus on strategy. Together we all benefited and it was a great time for the company."
  
  
• The challenge of remote working
  As the numbers of people working remotely increase, cultural issues and communication become more of an issue: "When we were all in one place, we had a good time. Now that we're all remote, it's much more of a challenge. "
  ​
• Numbers
  One leader suggested that the numbers of people in the meeting really affect the conversation. Smaller is better they said: "We have 10, sometimes that feels too many because of time, and because some people talk endlessly."
  
  
• Informality
  When deeper conversations need to be had, one leader said, "We used to hide behind social events to bring teams together. Now we have more informal gatherings out of the everyday context. They work really well."
  ​
• Go off-site and involve the team in the agenda
  Getting away from the office may mean closing the office for the day, but most leaders said it's worth it: "What works is getting offsite, all together at once, and having the team drive a section of the agenda so they can bring up anything they want to. It means closing for the office for a day, but it needs to be the whole team at once."
  
  
• Off-sites in nature are good
  Leaders also report that away days work, especially in fun outdoors places. or "strategy days at inspiring venues in the countryside. We like walks in the hills as well - though this has been less with the team as a whole."
  
  
• Common purpose
  Having a common purpose was also felt to be really important, especially when trying to introduce change: "If I was to have my time again, I would do more to ensure that we were aligned on our purpose before trying to change ways of working."
  ​

Conclusion
It’s clear from the responses we received that leaders feel it’s important to fit these types of conversations in, especially when so much about working in a team and getting things done together depends on having the right kinds of conversations, however challenging that might be.

So we encourage you to make space for meaningful conversations, and to be curious, open, and interested in what your team has to say. If you truly listen to each other, be prepared to be amazed!

At School of the Wild we bring teams into nature for an outdoor team building away day, to take advantage of being away from day-to-day distractions, when everyone is feeling more relaxed and open, to facilitate a space for better conversations.

After all, you can't solve problems in the same place you created them.

​If you’d like some help with having a more meaningful conversation with your team get in touch here.

​