Unpacking the Power of Personal Branding and Sniper Scopes with Josh Siegal of Real Matters

Josh Siegal is the Vice-President of Talent & Culture at Real Matters, a Network Management company that combines proprietary technology with independent qualified Field Agents to create a marketplace for mortgage lending and insurance industry services across Canada and the United States. Josh has held previous senior roles in the Media, Consumer Product and Not-for-Profit sectors and has in addition, taught Marketing and Organizational Behaviour courses at Wilfrid Laurier University and Nipissing University. He is a graduate of the Schulich School of Business (BCom) and Wilfrid Laurier University (MBA).

Looking back ten years, where did you think you’d be by this point in your career? How did you get here and how are you thinking about your own career development at the moment?

Thinking back ten years, I was working in the nonprofit world and was conducting the career due-diligence which would eventually allow me to start my MBA. I was thinking about three potential paths of how my career could unfold, but all three paths had the commonality of a career centered on a holistic understanding of business and strategy and a desire to avoid being pigeonholed into one specific function.

Fast-forward ten years, I’ve gotten to where I am today by really aligning myself with opportunities that connect with my personal brand, by focusing on becoming increasingly self-aware in terms of how I can add value to organizations and by seeking out opportunities which are aligned to my personal story while enabling continued learning and growth.

In terms of how I’m thinking about my career at the moment, learning and growth is at the forefront of everything I consider from a career perspective. If I cannot clearly articulate how a prospective opportunity will provide learning and/or contribute to my growth story, I definitively know it’s not the right opportunity for me.

What were some of the most important business lessons you have had to learn the hard way so far? How have they contributed to your current success?

Most importantly, being comfortable with failure was one of the hardest lessons I had to learn. When I was younger, I considered myself to be a perfectionist and perfection does not exist in the real world. Ultimately, if you are not willing to fail or if you don’t have the resilience to deal with failure, you are not working on things that are challenging enough. Failure is ultimately a byproduct of stepping up, trying something really difficult and pushing yourself beyond your comfort zone. If success was guaranteed, then you wouldn’t be needed to tackle the hard work that needs to get done and ultimately, you are not maximizing the value add to your organization.

Secondly, the concept of breaking ‘fixed-ness’ has been very important. Just because something has always been done a certain way doesn’t mean that it should continue to be done that way. Being willing to question and push back on the traditional ways of doing things is something difficult but critical. You always need to do the right thing as opposed to how things have always been done.

Lastly, you must be willing to forge your own path and journey. Everyone has their own career timeline, definition of success and experiences which are very personal in nature. Yes, it is important to network and learn from others, but you need to shape that to the context of your own journey and what it means to you.

What is the most common misconception out there about what shapes culture?

Culture is not about ping-pong tables, pub crawls and free snacks. These are just flashy perks that typically indicate a lack of depth in culture from my experience. While I believe that fun is an important and underutilized word in business today, culture is not about just having a “fun” work environment per se. I believe that culture starts with your Talent Acquisition process. This is the big rock at the front of your organizational process map. You need to think about it like six sigma. By dealing with the big rocks up front first, you will end up solving a lot of problems from a cultural perspective down the road. If you bring in the right people, trust them, and give them hard challenges to solve, this will shape your culture. Some senior leaders that I’ve seen get distracted by shiny new things when it comes to culture. Focusing on the core things like smart people and process should always be the key concerns.

What does leadership look like to you and what is the most exciting leadership opportunity for the next generation to make a real impact in today’s organizations?

Good leaders are like the scope on a sniper rifle. They help the shooter align targets, narrow the field of view, steady the shooter, minimize distraction and keeps the shooter focused on what is ahead. These are the things that great leaders do.

I admire Jack Welch and believe he is one of the best business leaders of our time. He had high expectations for people, was candid, never pulled his punches and one always knew where they stood with him. He developed systems, processes and tools to get his organization onto their aggressive growth targets and did so by creating a culture that was not tooled to the lowest common denominator.

Moving forward, the best opportunity for the next generation is to start looking at the world through a new lens and paradigm. They need to absorb the learnings of those who came before them, respect those experiences, ask a lot of good questions and seek alternative thoughtful solutions to the difficult problems of today. There is a great framework out there for innovative thinking called Systematic Inventive Thinking that I highly recommend others have a look at. It’s a great way to help people funnel their thoughts and tackle problems in a strategic way.

You’ve always been someone who talks about working smarter, not harder. What does that actually look like in practice?

It all begins with truly valuing and protecting your own personal time. If you don’t value and place boundaries around the time you are going to allocate towards particular activities, whether it be at work or otherwise, you lose your ability to gain a breadth of experience in life, which is integral to developing you as a fully fleshed out human being. This is the starting point to working smarter, not harder and will discipline you in terms of avoiding the easy answer of just throwing more man hours on trying to solve challenges.

Then it comes down to your ability to ask really good questions to get at the heart of what your stakeholders are asking you for. Thoughtfully probing your stakeholders and pushing to uncover the real “why” around what they want shows that you are thinking strategically, that you care and that you want to add value. It also allows you to push for better ways of doing things.

What’s the best piece of advice you would give to those new to the workforce to help them get ahead of the game in today’s marketplace? 

Regardless of how long you have been in the workforce, you need to be extremely self-aware and understand your value proposition. Be very clear about what makes you different and what your elevator pitch is. Be able to tell the story of your journey and connect the dots for others. Look at more than just your education in terms of the value that you bring. It’s always important to be true to yourself and have a vision for where you want to go. Finding that true north and aligning everything that you do in your personal and professional life towards following that true north is the only way that you can build a thoughtful and impactful story.

Josh S11.png
Aubrey Chapnick