How to Ask the Hard Questions and Be “Realistically Positive”


So much of the psychology of our business culture is about teams, working together, looking for the “win-win” scenario… and that’s all good. Those are good things to work towards.

But can we try hard to create a collaborative environment, and still handle the hard and uncomfortable questions and issues? I hope so, because it’s pretty critical. It’s important that we be able to work together and still be realistic about problems and potential road blocks. All too often in the work place, the people who always bring up the problems or the road blocks are branded as “negative.” But those two things don’t have to be mutually exclusive.  At the most fundamental level, we are talking about being great to work with, confident and positive, but still maintain the ability to ask the hard and uncomfortable question. Here at The Latimer Group, we call that being “realistically positive.”

It’s really a great concept, that is deceptively simple… The best ones usually are.

The point here is that while you are working hard to be collaborative and positive and enthusiastic, don’t lose the ability to also look at the flip side of issues. Don’t be afraid to be a voice of skepticism once in a while. Don’t be afraid to ask the hard question, like “what will our client hate about this?” Don’t ever stop trying to understand the key issues that may get in the way of the success you seek.

This is confusing for many people. In an effort to be seen as a collaborative and positive, “glass half full” colleague, many make the mistake of convincing themselves that this means you have to agree all the time, avoid hard issues, and be an eternally sunny cheerleader. Not so. The magic is in the method — the way you challenge issues.

If you ask those hard questions respectfully, without an attempt to embarrass anyone, without an “I know more than you” attitude, without an “I told you so” attitude, you can add great value to the people around you. You can be supportive and collaborative and positive, and still ask “are we sure we know how they will react?” Or “what are we missing here, that we have never thought of before?” Or “what does our competition do better than we do?”

The point today is that you can add enormous value to your organization by combining two approaches: be supportive and positive and collaborative; AND be realistic and inquisitive and willing to ask the hard questions.

Good luck, and have a great day.

At The Latimer Group, we believe that successful teams are built on honesty, open communication, and collaboration. For more on team building and team communication, look for Dean Brenner’s book, Sharing the Sandbox: Building and Leading Great Teams in the 21st Century, on sale now.

Photo by Brian distributed under the following license


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Dean Brenner

A book about change

The Latimer Corporation’s CEO Dean Brenner is a noted keynote speaker and author on the subject of persuasive communication. He has written three books, including Persuaded, in which he details how communication can transform organizations into highly effective, creative, transparent environments that succeed at every level.