If you haven’t yet, please read Part 1 of “Having Difficult Conversations”.

Part 2 is about difficult conversations I have had in the workplace.

Despite what people might think of you, have the courage to lead difficult conversations that demonstrates you taking ownership, and ultimately taking action to ensure you address the things that negatively impacts your team or organisational culture. When people say things you don’t understand or that you feel to be untrue, confront it.


Some of the most feared difficult conversations to have is in the workplace. As an HR professional who has occupied a senior management position, I could recount thousands of experiences, but today will share just a few.

I will start with when I was requested to review a proposal received from a prominent individual of value and influence to the company. The proposal was for this individual’s firm to replace one of our service providers. From the very start, I felt that if my feedback in respect of the proposal was not favourable, I would need to have a difficult conversation with the key decision makers. The relationship with the existing service provider spanned many years. The service received included annual reviews of the service offering compared to what else was out there, which led to a number of added benefits to the company’s employees over the years. So I did the necessary investigations and comparisons between the offering we were receiving, and the new prospective offering. I found nothing of additional material value from the new prospective service provider. Most of the evidence proved that the service and benefits all stakeholders were receiving from the existing provider, was still the best option. So I requested the meeting with the decision makers, which included the Chief Executive Officer.

Again, because of who the prospective new service provider was, I knew it would be a difficult conversation to have, but felt confident that I could provide detailed information as to why the service provider we had been using was still the best option. What made this conversation even more difficult, was that I needed to say the proposal received from the individual presented a conflict of interest, which I did, and also frankly asked whether the company would even be considering the new service provider were it not for who the proposal came from. Being a company with strong ethics, the decision makers agreed to remain with the service provider we had for nearly a decade. I believe that if we don’t put in the effort and investigate the facts, and speak up no matter how difficult or uncomfortable it might feel, decisions and outcomes could have adverse consequences for the companies we work for, the people we are responsible for, and for us in terms of how we feel about ourselves.

Another time, a manager who reported to me for just three months resigned with immediate effect. It was a resignation I didn’t see coming. From my perspective things were progressing well, and communication was constant. The letter of resignation, however, was the biggest shock of all. In summary, the individual blamed my leadership and management, or rather lack thereof (in her view), as the reason for leaving so suddenly. A lot of what was said was either taken out of context, twisted or blatantly untrue. What affected me most was that I was portrayed as everything I despise in a manager. Nevertheless, this led to a few difficult but necessary conversations. First with my line manager, then with my management team, and finally the entire department. To my line manager, who was naturally concerned as the position the individual was employed in was critical, I expressed my shock, and my disappointment that I could make another individual feel as expressed in the letter, true or not. What concerned me most of all is that it was said in the letter, that other members of my team felt the same way. So I suggested to my line manager that we conduct an anonymous survey about how the entire team in the department was feeling. I needed to know the truth so I could understand what I needed to change or do differently. The next difficult conversation was with my management team, to tell them of the resignation, and share the resignation letter with them. I felt sharing it necessary, especially in the world we live in today. People are so easily connected through various platforms made possible through technology. I feel strongly that gossip in the workplace is becoming more of a problem than it has ever been before, and felt that transparency was the best way forward. The last difficult conversation, was with the entire team, to speak about their responses in the survey which was shared with me.

I was tasked by my line manager to provide feedback to the team. This was not easy, as naturally, especially when anonymous, people feel confident in sharing everything they think and feel. From the responses it became clear to me that a few responses were as a result of assumptions, a lack of understanding, and then of course, gossip. All common in a workplace, and left alone, can affect performance, behaviours, relationships and wellbeing. However, about 90% of the results were not in line with the views and feelings of the individual who left. The majority of the responses were positive, and other than high standards of performance, working incredibly hard and long hours, and the level of accountability expected causing some anxiety and a lack of motivation, there was a team culture that I felt proud to be a part of, and felt fortunate to lead. My focus therefore could shift to dealing with what was causing the team’s anxiety and lack of motivation. I believe when we are transparent, open to receiving criticism ourselves, showing we have weaknesses and can be vulnerable too, we demonstrate strength, equality, and our own learning continues.

Lastly, when working closely with people for many years, you can develop friendships that extend outside the office. These friendships can become some of your most valued relationships. This has happened to me. Three of my friends started out as my colleagues, at different points in my career, and my relationships with them are all on different levels. What made this more complex, was that they all reported directly to me. So day-to-day management of these individuals often led to many difficult conversations. Some of these conversations related to improving performance, highlighting development areas, making decisions in terms of awarding them bonuses, or not, because performance just wasn’t good enough.

As a line manager, a leader, and the custodian of all things HR in our company, I had to ensure fairness. I have even had to take decisions for minor issues of misconduct that had consequences for some of these individuals. I remember a particular difficult conversation with one of these individuals relating to growth and development of others who reported to her. She was either not frank enough about overall performance or direct enough about development areas. She would provide solutions in all things, and check and edit their work. This limited them thinking for themselves, and taking ownership for their outputs. Were I not to have this conversation with her, what kind of manager and leader would I be? I believe that if colleagues who are also your friends do not understand and respect your role and responsibility within the working environment, then they don’t truly value your friendship either. I am fortunate that I have these individuals in my life, and that our friendships still remain.

Overall, I hope that my account of difficult conversations in the workplace might ignite in you the belief that all conversations are possible, no matter what or with whom. Everything starts with having the courage to have the conversation, when it’s needed, and to see it through. The ending might surprise you, might make you feel lighter and able to move on. All difficult conversations can be had if you ensure your integrity is intact, and that you never take away another’s dignity in the conversation.

And so, my two part blog series on having difficult conversations comes to an end.

If any of my posts have been of any value to you so far, please follow my blog, comment below, and engage with me by sharing your thoughts and experiences.  Also please forward this onto others you think might benefit from this post. Until next week…

Yours in Adapting & Being

Adapt&Be Employment, Leadership & Management, Workplace

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