I’ve always had an intrapreneurial spirit in the jobs I’ve held. In some roles, I have been given autonomy with the ability to set North Star goals and chase them. In other roles, I’ve found myself building up consensus and bubbling ideas upward. This has involved some tough conversations.
If you’ve checked my other blog posts, I tend to focus on innovation, creativity, corporate culture, project management, and organizational change management. These areas fascinate me, and I get very passionate about them.
Depending on the corporate culture, I might be overly opinionated due to my excitement of what is possible. I can come off as brash when I think I see a clear path to success that others aren’t seeing in the same light.
With that spirit in mind, I’ve found myself in disagreement with my bosses, co-workers, or even family members from time to time. I enjoy debates quite a lot, as long as everyone remains civil and understands that two people can have a heated debate without being mad at each other.
Despite what we see on the political stage, people can disagree and still hold mutual respect for one another. This is a key tenant in understanding and having important but tough conversations – even within honest evaluations.
Conversational Toolkit
Some skills are not directly taught in schools. Businesspeople often talk about soft skills, which are not something you’ll see discussed in any depth for students. Listening skills, empathy, emotional intelligence…you can pick your favorite buzzwords here.
Just like the topic of personal finance, most of us enter the “real world” ill-equipped and must learn as we go – often wishing that someone would have shown us how it all works sooner.
I didn’t read many non-fiction books until I was in my thirties. I missed benefiting from some of the tremendous advice in books that have since helped me reflect on my past experiences and to improve my approach to tough conversations. Here are some that I have used to shape my principles (in no particular order):
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Crucial Conversationsby Grenny, Patterson, McMillan, Switzler, & Gregory | Never Split the Differenceby Chris Voss with Tahl Raz |
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Boundariesby Dr. Henry Cloud & Dr. John Townsend | Linchpinby Seth Godin |
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Principles: Life & Workby Ray Dalio | The Five Dysfunctions of a Teamby Patrick Lencioni |
Personal Experience
Having advice ahead of time with conversational toolkits is helpful, but there is no substitute for experience and living through it.
I’m generally a “people pleaser” and enjoy making others’ lives easier even at my own expense. But it wasn’t until I fully understood the concept “to be unclear is to be unkind” that I started to realize that “toxic positivity” was a problem that should be avoided.
I wish I could say that tough conversations are without risk, but that would be untrue. Just as you are better off with conversational toolkits available to use, you also must realize that you may be talking to someone who does not have the same mental models and “tools” at their disposal. So measure your risks and tolerance for the individual you’ll be talking to and be intentional with it.
A Positive Experience
The first time I experienced this, I stumbled upon it, having not yet wrapped my head around these ideas. We had a boss who was known for being temperamental and prone to getting angry. He would love someone one minute and be a sworn enemy the next.
I had reached a point where I wanted to see a change in direction, a change in the culture of the company. I knew that my close colleagues felt the same, but everyone was nervous about talking to our boss about it.
Despite my introverted nature, I buckled up and decided to have a tough conversation with my boss. There were moments of contention in the chat, but he listened. Leaving his office, I didn’t have a good feeling and felt like nothing would change. My co-workers said, “No! Why did you do that? This could get bad for all of us!” They had me fearing that I made the wrong choice to speak up.
The thing is, that first day was a little uncomfortable… But the next three months or so were probably the best interpersonal interactions I ever had with that boss. After he had some time to digest what I brought up, he showed me more respect, and was willing to talk about broader topics with me. And best of all, he began a new approach that aligned with what I was hoping to see in our workplace.
A Negative Experience
At another company, we had an employee morale issue. I was brought in as a company leader, and the leadership knew about the issue. After a few months of talking to other co-workers and getting a lay of the land, I told myself that I’d try to champion the changes that needed to happen. If you’re not part of the solution, then you’re part of the problem.
It was a tough situation all around. The culture was ingrained, and if the company hoped to overcome it, there would be a lot of history to overcome. My efforts toward a solution came with many tough conversations.
I needed to manage up and have crucial conversations with my bosses about culture and allowing employees to grow and set their own goals. I also needed to manage laterally and downward when I’d hear watercooler talk spiraling.
Crucial and Productive Conversations
For the leaders, there were some seemingly productive conversations, and then there were some that hit a brick wall. For the others, I had to repeatedly remind people that nothing would change if you just complained to your peers. I tried to encourage them to find paths toward their desired end goals. In both cases, I was met with reluctance. The culture was in a rut and the people weren’t equipped with conversational toolkits to make tangible progress.
Sadly, I failed. The turnover at the company continued. The negative side-chats dominated. The company allowed bad actors to stay, which disheartened others. I wasted a lot of time.
In my last months there I had decided that I’d make my last push to make a difference and if I could not then I’d start looking for another place to go. The company leaders felt the shift too, talked to me about it, and we ended up amicably parting ways.
In one way that was a negative experience, but I’m a firm believer that you can learn from anything – even if it is what NOT to do! I’m now able to recognize areas that may be too far of a leap to make the effort worth it. I also found my next role with a much better culture.
Conclusion
Effective communication is crucial in personal and professional relationships. While it can be uncomfortable to have conversations where there is disagreement, what I’ve found is that it is much worse to let things sit and fester.
In my experience it is far better for both parties to know the facts sooner than later. It is much harder to deal with tough conversations if it comes with a history that only one person experienced. You don’t want to surprise the other party with, “I’ve felt this way for a long time.”
My advice is to tough through the nerves and have the conversations you’ve been avoiding. The alternative is more painful in the end, even though it feels more comfortable now. If things go poorly after an honest and civil conversation, then you’ll find that you are likely better off making a change, and they’ll probably feel the same way too.
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