So Many Questions, So Little Time

As much as I enjoy speaking with people who are part of a family business, some of the discussions I have with colleagues who also work with such families are even more stimulating.

These can involve general topics that affect many families, or, on occasion, a specific family situation that one of us happens to be dealing with concerning a particular client family.

Some of the most energizing dialogues meander all over the place, from general to specific and back again.

This blog stems from some notes I jotted down after one such meeting a while back, with two friendly colleagues who happen to work for a multi-family office, where the subject matter bounced all over the place, much to my delight.

Needless to say, together we raised way more questions than we answered, but all were related to how families can get their needs served as they prepare for the future.

Handling a Family’s Concerns

The questions also rotated around what a family could do, should do, and would do, depending on a number of different factors.

For example, what should a family be concerned about, as they begin to prepare for an upcoming generational transition?

What could they do about things, assuming that they even properly comprehended what challenges they were actually going to be facing together?

What would they be ready to undertake as first steps to move in the right direction together as they begin to understand the importance of doing this work as a family?

Finding Resources and Getting Help

What kind of work could they be doing together, assuming they knew that some help was available to them?

When it comes to what a family should be doing, as advisors that’s really tough to assess up front, until we’ve done the work and spent enough time getting to know them, so that we can have some ideas to suggest to them.

Assuming that we have some ideas, we also need to consider what the family would be able to handle right now, so that we can get some small early wins and develop momentum with them.

Preparing for the Family’s Future

An interesting way to learn more about a family can involve asking them what they would like the future to look like for their family.  You can expect different answers from different family members, so you also need to decide whether you’re asking them as a group or one-on-one.

After that you might want to ask them what they think they could be doing to achieve that kind of future.  A follow-up to that one might be to ask what they think they should start with.

It’s one thing to have these kinds of conversations with people who are part of a business family, but it’s even more important to make sure that they are also having such discussions amongst themselves, as a family.

Encouraging Families to Have Dialogues

As much as you might think that most families regularly talk about things together, you’d be surprised how often you find out that the really important subjects just don’t seem to come up very often.

Family enterprises result in some complex relationships between people where the family and the business overlap, and maybe because people spend lots of time together, they assume that they know how the others feel.  See: Curiosity as the Antidote to Assumptions in Families

As advisors we can and should encourage families to have dialogues about important subjects that involve their futures together, but that might not be sufficient.

Often what families really need is someone to guide such discussions so that they feel like a safe space for everyone to share, which is not always the case.

Moving Away from Should to Could and Would

Often families who are looking for advice will ask what should we do.

Even when we have some good ideas, it’s better not to jump in with an answer right away, as noted above, because we really need to get to know them first.

Helping them see what they could achieve and become together can go a long way.  But there’s usually lots of work involved in hitting their full potential, so it’s best to also share with them everything that would be involved in getting there.

What we want to avoid is having any of our family clients someday having regrets about what they woulda, coulda or shoulda done.


We All Know What Happens When We Assume

For me it was Mr. McGee, a High School teacher, who first shared the dangers of making assumptions. I cannot recall the context of this lesson from circa 1980, but I distinctly remember him writing the word “ASSUME” on the chalkboard.

He then said, “You know what happens when you assume?”

The class waited for the punchline. He then drew two short vertical lines, before and after the “U”, leaving three distinct words:

A  S  S   U  ]   M  E

“You make an ASS out of U and ME

That was over 40 years ago and it’s still with me, so let’s just say the message stuck.

And We Are ALL Guilty of It

I’m pretty sure most readers will have heard some version of this tale somewhere along the way, and if not, feel free to borrow the one from Mr. McGee.

And, not surprisingly, all of us are also certainly guilty of making assumptions, because, well, you can’t not make them sometimes!

But what if there were an antidote that we could dream up that could help us minimize those occasions where we risk making an ass out of each other, especially with important people in our lives, like our family members?

Well I’ve got good news, there is one. And we all have some of it in us, and we can improve with practice.

My title has already given it away, but for those of you who already got lost in my prose (and I don’t want to assume that you recall the title of this blog) it’s curiosity.

A Coaching Webinar as Source

The idea for this post came a while back when I was watching a webinar about coaching, and presenter said, “The greatest resistance to curiosity is assumptions”.

I jotted that down because I felt like there was some juice to be squeezed from it.

But as I thought about it from many family business contexts with which I am familiar, I decided to turn it around and focus on the assumptions that too many people make about family members.

Rather than looking at “resistance to curiosity”, I want to concentrate on using curiosity to overcome the many problems that come from not having enough curious conversations.

It Comes Down to Attitude

My guess is that senior generation family members are typically guilty of this a bit more often, but I’m sure it happens in every generation.

It typically stems from an attitude of believing you know things you just never bothered to verify.

“Of course the kids will want to work in the family business” comes to mind for me, personally.  In my case it also came along with a healthy dose of not leaving me any choice.

My Dad knew what was best for me, or so he surely believed. Of course his plans for me also happened to be what he thought was best for him.

He could have been much more curious about what I wanted, but he never allowed himself to go there, just in case he’d learn something he didn’t really want to know.

Someone from Outside the Family as a Spark

So how might one go about sparking the kind of curiosity that I’m talking about here?

When the group of people is always exactly the same, it’s easy to get into a rut, and there isn’t much room for curiosity.

But what happens when an outsider shows up with the group, and that person is curious and begins to ask questions to satisfy their curiosity?

This could be just the right way for some new subjects and ideas to land on the table for consideration.

There are many things I should have pushed back on with my Dad, but I did not, for all kinds of reasons, many of which are more clear to me now than they were decades ago.

Could a well-placed and well-meaning outsider have helped spark certain discussions that could have been started, so that I could shine a spotlight on some of the many assumptions he had made about me?

Recognizing That Something’s Amiss

Sometimes you know that something is amiss and if you take the time to ask what you’re assuming, you’ll likely be onto something.

If you can then get curious and actually ask questions so that you can learn, you’ll be going in the right direction.