How to have a challenging discussion

This is one of the common issues to come up during my individual and group coaching sessions. Being able to challenge a colleague in a constructive way, one where the other person doesn’t feel attacked yet they understand the issue, is crucial for a productive and happy work environment.

Yet, it’s often something that is avoided. And when this is the case, it can lead to conflict in the workplace. Whenever I’ve been asked to intervene when two individuals, or a whole team, is in conflict when I dig down to the root-cause it’s because an important, difficult conversation hasn’t happened or has happened in a clumsy way.

Feedback is a key factor in building a high-trust environment, as evidenced in a study by Ana Maria Costa and colleagues.  In a review of 125 studies, the researchers found trust is fed at three levels. They found good relationships with each other and the team leader, tasks where people needed to work together helped build trust and a climate where people could give open and honest feedback safely contributed to better levels of performance and higher job satisfaction.

Here are eight things you can do to help a challenging conversation go well:

  1. Feed-forward rather than feed-back. Rather than rake over the past, it might be more productive to focus the discussion on the future performance or behaviour you’d like to see. Art Petty wrote a great piece about this, talking about how the combination of wanting to be liked and wanting to avoid pain are just two reasons why we hate difficult conversations.
  2. Be your most compassionate self. This doesn’t mean you’re going to be a soft-touch. As Shakira Joyner said in a post about compassionate leadership, Enabling people to achieve their goals and getting them where they want to be will sometimes involve difficult conversations”. And as Monica Worline and Jane Dutton state in their book, Awakening Compassion in Organizations, “…organizational messages maintaining a positive default assumption about people at work – that they are generally good, capable, and worthy of compassion – make these difficult dialogues about errors or unfortunate events easier”.
  3. Put yourself in the other person’s shoes and be respectful. In a study of over 100 employees and 22 supervisors in an American hospital, leaders who displayed empathic concern were more likely to have staff who help each other and put extra effort in to their work but only when there was little difference in relationships between the leader and each team member. In other words, those leaders who treated people broadly the same (whilst respecting them as individuals) tended to have better levels of team co-operation and individual effort.
  4. Ask yourself if you’ve being reasonable in your expectations. Maladaptive Perfectionism developed by Jennifer Grzegorek and colleagues is where a person has extremely high standards and are always beating themselves or others up for any perceived imperfection. This can cause high anxiety over mistakes and can be a reason for micromanagement. Before you have the conversation with the person, ask yourself if you are being reasonable in your expectations.
  5. Make it about the issue not the person. Fundamental Attribution Error, developed by Lee Ross, Teresa Amabile and Julia Steinmetz is the tendency to attribute others’ weaknesses to character rather than circumstances. When the recipient of the feedback feels it’s personal then don’t be surprised if they react defensively.
  6. Be clear about and stick to the purpose of the discussion. Avoid the s**t sandwich. It causes confusion. Jennifer Miller talks about the importance of separating praise from feedback. And as Kate Russell, an HR expert, says in a recent piece on grievances in People Management magazine, “It’s about standards and how you communicate them. It’s not enough to say ‘you’ve not met the standard’ – you need to spell it out. If this went to tribunal, you’d need to show that the employee knew what they should have been achieving, and that you were clear about what that was.”
  7. Lead by example by showing how to receive constructive challenge and feedback. In a study on humble leadership, Susan J Ashford and colleagues looked at 465 top leadership teams across 65 small and medium Belgian and American companies. The researchers found that when CEOs proactively asked their top team for feedback it had a direct and positive impact on company performance. This was dependent on how confident the overall leadership team was. Visionary (heroic) leadership was also found to have a positive impact on performance but this seemed to be when overall team confidence was lower. And as Brendon Burchard says in his 2017 book, High Performance Habits, “consistency in receiving feedback is the hallmark of consistent growth”.
  8. Come from a supportive place. Kim Scott, the author of Radical Candor, in an interview with Kevin Kruse, says there are two elements to great feedback. The first is you need to care personally. The second is the willingness to challenge directly. Getting the balance right between support and challenge is crucial – a point that Anna Rasmussen makes in a commentary piece for People Management.

I have a tool to help you get that balance which I teach with the managers I work with. You can download this tool FOR FREE HERE.

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One comment

  1. There is a lot of value in what you have written, and thank you for that. The difficulty, as I see it from my small corner, is we’ve been trained since infancy not how to discuss. A couple of people, one man and one woman, grew up in households where discussions were the norm. In their youth, they would sit and listen to the adults discuss the issues of the day as well as other topics. One of the two, from what I’ve learned, went onto a successful career discussing, and that person is very good at listening as well as sharing.
    Debate clubs would be very good in schools provided the instructors know how to discuss. Then, debate rules would need to include the ideas you have written, but allow some differences as debating is necessary even in the face of those not as equitable.
    I, myself, find the arena of discussions a learning prospect. As a teacher for over 20 years, I have listened to my students when they have points during discussions, have taught them how to write essays supporting their points but also understanding opposing points of views, and had them read in class that others may learn. I have always challenged them to provide their views, but also to realize others may not agree with them, but may, and that learning how others see is as important so they may investigate their own beliefs or points.
    I have asked the question, what two things would you change in the current educational system, then listening afterwards. What I have found is the inability to speak heartedly from a thoughtful perspective. Most don’t wish to comment, perhaps afraid of commenting out loud to someone they don’t closely know, or react defensively, not willing to have a real discussion. A few I have been able to share ideas, but even with these people, the air becomes stifling and real discussions soon end. Only one of many did we have a real heart to heart, but that was probably more to us being in agreement with most aspects.
    We grow up in households, and many don’t demonstrate how to discuss opposing points of view. The media is so one-sided on so many topics, and many television talk shows don’t demonstrate very well how to discuss. In schools, we have teachers who teach, but don’t often know how to show or how to hear children’s views even if they counter the pollitical culture (dangerous to be pc incorrect in school), so no real debates can take place there unless you have a teacher like me who likes to hear ideas against my own beliefs.
    I remember the topic of saving puppies. I thought the topic good. I thought the students’ ideas and desire to help these animals fantastic. However, I had to add that while I personally wouldn’t venture down this road, that I see dogs as I see all animals (Though, I must admit, I like dogs a lot.), I thought her compassion was well-placed. What I found, perhaps being a man, was my simple comment about my not venturing down this road was met with some skepticism by some students. They wanted everyone to love dogs, and a simple opposing view brought harsh reactions. But this was important. I explained that while they have a right to their views, others do too, and we can’t know the range of reasons behind everyone’s decisions.
    You see, I did not grow up with pets, but a couple of friends had dogs I adored. Also, having been a hunter and fisherman, my experiences may be different. I also worked in a zoo for a couple of years where slaughtering dead animals (i.e. road kill) or putting animals down for slaughter (On occasion, someone would bring in one of their cows that would not survive, but didn’t want to see it in pain.) was the norm, the meat used for the tigers, lions, and other carnivores. So my experiences were very different than these students’.
    Too many of us live in our tiny corners. We don’t venture out to be challenged. But when we do, too many look for only commonalities for support, unwilling for their own beliefs to be challenged.
    Thank you again, so much, for your words of wisdom.


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