What makes someone a great leader? Craig Dowden digs in

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The concept of leadership has always fascinated Craig Dowden, a Toronto-based executive coach, keynote speaker and author. Having witnessed examples of where positive leadership has turned around challenging situations – and where poor leadership has created chaos in promising circumstances – Dowden has made the study of leadership his life’s passion.

His curiosity led him to pursue a doctorate in psychology, with a concentration in business, exploring how great leadership happens and looking through a scientific lens to answer his own questions: What makes people want or not want to follow certain individuals? And what separates great leaders from the rest?

“Leadership, like any other domain in our lives, has been extensively studied,” says Dowden. “It’s imperative we learn from that knowledge base. What are the evidence-based, concrete behaviours of the top leaders that apply in most situations?

“Rather than base our ideas on one case, what can be learned from hundreds, if not thousands, of examples?”

To that end, Dowden has drawn upon decades of research as well as his own consulting background and personal interviews with dozens of CEOs of top companies including McDonald’s and IKEA. His new book, A Time to Lead: Mastering Your Self . . . So You Can Master Your World, aims to help leaders develop real-world solutions to today’s challenges.

We asked Dowden for his insights about leadership in family-owned businesses.

What’s unique about leadership in a family-owned business versus a regular business?

In a traditional organization, you have the individuals within it and their personalities and the personality of the organization, so you have to figure out how to bring those two entities together. In a family-owned enterprise, you’ve got the familial personality and personalities within that, so there’s an added layer superimposed on the individuals in the organization. That’s a really critical difference.

Because you’re interacting as family, you also see people outside of work in ways you likely wouldn’t see colleagues in a traditional organization – like at a family barbecue or at home – so you have access to private data about them. Sometimes we make assumptions about how someone is, based on that external data, and form conclusions. If someone’s really messy at home, you might worry they’re not detail-oriented at work.

Also, when you’ve grown up parenting a child or children and now they’re in the business, it can be difficult to let go of the past and our expectations. Those elements are all additional data points.

What’s your advice to strengthen leadership?

A critical first step is figuring out the type of leader the organization needs. What are those skills and qualities that are absolutely essential for someone to succeed in that role?

With that template in place, now you can assess each individual who could take on that role and how they fit currently. Where do they fit really nicely? Where are the gaps? What developmental opportunities or training or coaching could we offer to bridge that gap quickly and effectively?

The template is vitally important, because otherwise people can have different scorecards or metrics and might feel they’re in different positions across the board than what they are.

You also want to determine whether you’re looking from a talent planning or succession planning process. While all that’s helpful in making informed decisions, you need to recognize the opportunities and risks of putting people into particular positions. It’s a great opportunity for open and honest conversation.

How do you approach difficult conversations?

The best way to have a constructive conversation in a difficult subject is to have the person come to that realization. Approaching with curiosity is a great way to start to see if they sense that the readings are off or not where they need to be.

You want to have an exploratory conversation. Where do you think you’re doing well? Where are some challenges? Where do you need support?

This is where having clear markers of success and performance metrics are so wonderful, because we can gently raise that and say, well, for this past quarter, we’re looking at this. Talk to me more about that gap, where we are and what do we need to do to fill it. It helps to keep things in a constructive light.

Where’s the best place to have those conversations with people in the family business?

I love the expression, ‘Praise publicly, criticize privately.’ In the vast majority of cases, it’s a one-on-one conversation because the more people around the table, the more risk there is that someone’s going to feel defensive and lash out. You want to consider the family member and what environment is going to be best for them.

Sit down with them and say, ‘Hey, from time to time, I’m going to have feedback for you, just like you’re going to have feedback for me. What’s the best way you want me to have those conversations, particularly if it’s challenging?’

Someone might say, ‘Just pull me aside at the cottage,’ while someone else might want to keep work and family separate and say, ‘Talk to me at the office.’ Now you understand where and how they best want to receive feedback. With family members, it’s vital to talk about how you’re going to interact with each other at home and in business.

Trust is the most invaluable currency in any personal and professional relationship, and it’s elevated to its maximum importance within the family. To be successful, keep transparency and trust top of mind.

How do you find your authentic voice?

Some people feel you have to bare your soul and get into extraordinarily uncomfortable places. That’s counter to authenticity, because now you’re not comfortable about how you’re expressing yourself.

Authentic conversation allows you to show up in a way that you feel your values and beliefs are being honoured, as well as in a manner that’s creating a positive impact on the people around you.

What’s your advice on building resiliency?

From a resilience standpoint, stress comes from feeling under-resourced.

So as a family member, as well as the family collectively, we can ask ourselves, ‘In what areas do we have the resources we need to deal with the pressures we face? Where do we feel under-resourced? What are our risks?’

That’s incredibly powerful, because now we can decide where we need help.

More from Canadian Family Offices:

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• FEA designation brings spark to Krista Han’s work with business families
• Wealthy people and family offices: Hackers see you and know you’re vulnerable
• An ‘outlier’ year: What wealthier investors are doing, and their plans for 2023

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