I have a habit of turning things around and looking at them from a different perspective from most people. So while many are pre-disposed to think in terms of finding the answer to a question, I prefer to step back and question the question before answering it.

This habit goes back to my days of working in the family business in my early twenties. When we needed to hire someone to fill a position, the task of finding good candidates somehow fell to me.

I suppose that it was because we did not yet have an HR person in those days, so the occasional need to fill a position became a project that went to “Steve Junior”.   So here I was being put in a position where I needed to first figure out a number of things before I could even begin.

The department head’s question would start with “Can you find someone to fill this job in my department?” While there was a brief answer (“Yes, of course”), what became more important was the series of questions that soon followed. What is the job description, what kind of experience are you looking for, what is the salary, etc.

I got into the habit of asking lots of questions, and I still do lots of it today. Like many things, the more you do something, the more comfortable you become doing it.

Sometimes when doing job interviews I would ask candidates “What is more important, knowing the all the answers or knowing the right questions?”  I can tell you that we never hired anyone who did not hit that one out of the park.

Many people spend a lot of their time trying to find answers, even though they may not have taken the time to make sure that they are answering the right questions.

Somehow when we begin looking for the answers we feel like we have started down the road to finding a solution, while thinking through the questions still feels like we are in neutral and not making progress.

Many businesses bring in consultants hoping to find “the answer” to their problem. I believe that anyone who promises you answers without first ascertaining that you are looking at the right questions is someone to be avoided.

I maintain that if you take the time to ask all the right questions, the answers often take care of themselves.

An outsider can often bring a different perspective to your situation, and the simple fact that they must ask a lot of questions can make you think in terms that you might not have thought of, and this can in turn help you with both the questions and the answers.

Don’t be afraid to ask questions, but try to avoid Yes/No questions. Learn to ask a lot of “why?” questions, as hearing people’s answers to those are usually the most enlightening.

It should go without saying that actually listening to the answers that you get is pretty important too.

Every once in a while, it is good to ask yourself a couple of big picture questions, because the answers you come up with on those will help you put a lot of things in the proper perspective.

I like to start with “Where are we trying to go?” followed by “How do we plan to get there?”

They are very simple and quite general, but I think if more people in more businesses took the time to stop and ask themselves these two simple questions, on a regular basis, they would be more likely to make progress and stay on track.

So, where are you trying to go? And how do you plan to get there?


Steve Legler “gets” business families.
He understands the issues that families face, as well as how each family member sees things from their own viewpoint.
He specializes in helping business families navigate the difficult areas where the family and the business overlap, by listening to each person’s concerns and ideas.  He then helps the family work together to bridge gaps by building common goals, based on their shared values and vision.
His background in family business, his experience running his own family office, along with his education and training in coaching, facilitation, and mediation, make him uniquely suited to the role of advising business families and families of wealth.
He is the author of Shift your Family Business (2014), he received his MBA from the Richard  Ivey School of Business (UWO, 1991), is a CFA Charterholder (CFA Institute, 2002), a Family Enterprise Advisor (IFEA 2014), and has received the ACFBA and CFWA accreditations (Family Firm Institute 2014-2015).
He prides himself on his ability to help families create the harmony they need to support the legacy they want. To learn how, start by signing up for his monthly newsletter and weekly blogs here.