Don't go along to get along

As a startup entrepreneur, I've been mingling more with other startup founders and investors. What's interesting about this group is that most of them are highly self-confident folks. Some built their confidence on having had relevant experience. Almost all of them are highly outspoken and ready to share their thoughts with you, whether you want them or not. This can be rather different from having a team of employees who may feel it's not their place to express their disagreement with your plans or strategies. 

Sometimes, I feel that I can more easily get into a devil's advocate conversation and have lively debate about different ways of tackling a problem with other founders and investors who have previously been startup founders. From the outside looking in, it appears that conversation is more confrontational, but no one's feelings are hurt...everyone is just trying to weigh in available options and their potential pros and cons. I find this refreshing!

While it might be a touch uncomfortable for some to have such open discourse with others, I think it's a good idea to hang out with people who have contrarian thoughts that may not always be popular but their thoughts could be right and they are willing to challenge your thought process. In life, there aren't always clear right answers. As such, it's really just a process of making as best a decision as you can, given incomplete information and resource constraints. The more you can surround yourself with people who are willing to speak frankly about anything, including touchy topics, the better. 

For employees, it's helpful to know that your managers are often interested in hearing your thoughts, even if they go against their own initial thoughts; effective leaders never want "yes" people on their team as it can be rather deadly for the organization. That said, it doesn't mean you have to be rude in the way you do so. There is no need to be haughty or make the person look bad. There's a time and place to provide feedback. Also, there's a lot to be said in using tact and appropriate demeanor to communicate opposing views with the effect of causing thought-processing which could lead to a change of mind.

The bottom-line is: don't go along to get along. It may have the appearance of keeping the peace and making everyone happy. However, in reality, no one is happy when they don't get to speak their minds in constructive ways that can benefit everyone in the organization for the long-run.