The Path Less (or Never) Traveled: Why We Should Stop Scripting Careers as Employees and Business Leaders and Embrace Unconventional Talent

Following a strict career path, or assuming one for others, can hinder growth and goal achievement for both individuals and companies.

A purple flower emerges a field of yellow flowers
by Deanna Self
May 26, 2022

My most favorite part of leadership is supporting and watching others grow and achieve their dreams. Not the goals someone else has set for them; the ones they have set for themselves. The ones that bring pure joy and satisfaction. Sometimes that can be very hard to do if you approach leadership with a traditional mindset.  I’ve mentored many people over the years, and I’m always surprised by how scripted they think a career path should be. If you take a look at my career path, it is anything but scripted. I’ve owned my own companies – which means I was everything from the janitor to the CEO – and I’ve worked across many different functions within the corporate landscape. What has allowed me to make big jumps from function to function, such as sales to IT, is having the right focus. Instead of trying to become an expert – or thinking I need to be an expert – in every single area before moving on to my next role (as women often do), I have tried to focus mainly on the gaps and how I can best support them to drive productivity and innovation. It’s not to say a person doesn’t still have to perform well on the basics but defining expectations and approaching “success” differently has made me stand out – and it can help others stand out and achieve their dreams, too. 

What Digital Transformation Has to Do with Career (and Hiring) Decisions 

As I have navigated through a variety of roles, it has opened my eyes to the skills and capabilities that exist amongst different teams. Role by role, and layer by layer of those in the organization, I’ve come to realize there is a huge opportunity to forgo the traditional mindset of career progression and, just like we do in day-to-day business, think outside the box when it comes to adding new talent to the team. One of the biggest reasons we need to take an approach like this is because the market is changing and by default, we must also consider how we can change to best support customer expectations. The way we do that is through digital transformation.   

I think everybody has heard the term “digital transformation.” However, I’m willing to bet there are a lot of people who don’t really understand what it means for them or for their company. 

Do you even really understand what it means for you? 

How we do our work today is mostly driven by the technology that was available at the time we joined the workforce or accepted our current jobs. That’s right, many of us still view technology as a luxury versus a required tool because legacy processes and business practices haven’t been technology dependent, and we’ve been using both for a long time.  

Unless you’re right out of school and working at your first job, reflect a bit on your career and personal history with business technology: 

If there wasn’t a good technology solution to support the work, then the work stayed manual.  Over time, some of this work may have blended a bit to create some new processes, and you may have used a few ad-hoc solutions. But I (once again) bet that much of it is still siloed, and you spend many hours in a day just managing what falls outside of the process – which someone likely didn’t follow.   

That brings me back to the impact of digital transformation on us individually as employees and leaders, as well as our team and company collectively: 

If I put it simply, digital transformation is taking our manual processes and digitizing them so we can automate and eliminate manual interventions or possibly create new processes which help bring a better experience to the business, our culture, and the customer.   

But how do we bring about and support digital transformation when so much of the knowledge that exists is conducive to legacy systems and processes?  

It can sometimes be difficult to ask a person who’s been supporting business the same way for years to suddenly determine how they can now do their jobs, or even menial tasks, very differently. A good example of this is when I was in an IT role. I went to the sales partners I supported and said, “If you could have anything you wanted from a technology standpoint to really improve visibility and make a difference in your operating margins and customer experience, what would it be?”   

I had a full page of technology enhancements listed that I knew would help in a variety of areas, and I was biting at the bit to start checking them off, certain this group of people would share in my excitement about each of these improvements.  But, to my surprise, the response I got from the team was “I’d like a USB drive and to be able to print a PDF.”  The moral of this story: it’s hard to think about how you can conceptually do your job differently. This is the moment I realized I needed to start bringing in sources that could show them how work could be done more effectively.  

Changing Our Expectations about “Experience” Will Help our Careers (and Companies) Thrive 

We need to disrupt how we perform our jobs today, and big disruption comes from new mindsets, perspectives and experiences. To be successful, it means the right capabilities need to exist on our teams. If you’re working with a team that is pretty tenured, bringing in new talent or helping them develop their external lens by engaging with consultants or peers in other organizations can make changes easier. 

This means you need to bring in talent that can conceptually challenge the status quo but who are also strong enough to help lead the charge to bring about change. For me, this is where I seek out what would be considered unconventional talent for my team.  

What do I mean when I say that?  

Finding someone who doesn’t fit the mold of your current team – who can fill a gap. Rather than “fit,” think about how their skills and perspectives complement others and add to the team’s strength. 

If I took a good guess, I’d be willing to say that most teams have an opportunity to bring about better visibility – to improve their reporting so that it really tells a story and can drive action. And there are probably several processes that produce redundant work through a manual approach. That’s because, traditionally speaking, if a team had an open role, the mindset would be to bring in someone who has the same skills as the others on the team to support this work. However, the better move would be to bring in someone who… 

  • has the skills to help automate the processes (like UI Path as example) 

  • has proven success of leading/implementing innovation, or  

  • may have strong analytic skills to story tell through reporting so you can drive additional value through your team.   

I personally look at these gaps as opportunities to seek out folks with these different strengths from various parts of the business – to bring those missing capabilities into my team. I also see each open role or skill gap as an opportunity for my current team members to gain experience in other areas, to become valuable beyond their current strengths – the ones they were brought in for originally.   

Don’t Accept the Status Quo 

As someone who may be reading this and thinking about your career path, I challenge you to look outside of your structured organization and identify how you can leverage your strengths to bring about positive change to the organization in other areas, while also learning and building on your capabilities. There are people like me who are seeking out that unconventional talent, so get out of your comfort zone.  

I issue the same challenge to hiring managers. Don’t just look for someone who can backfill a role with the same skills that have always been needed. And don’t assume that “similar” skills, experience, or even personality will ensure compatibility between job candidates and your current team. As others say, diversity of thought is key to success. Well, diversity of skills, experience and mindset make a difference, too.      

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Deanna Self
Deanna Self is a supply chain executive with Zebra Technologies, responsible for the oversight and management of Zebra’s largest order fulfillment distribution center. She is an industry veteran with over 25 years of in-depth knowledge and experience in sales, operations, and information technologies. Deanna’s passion and focus is to transform business with new and sustainable solutions that drive efficiency and customer satisfaction. Prior to Zebra, Deanna spent over two decades in the food and beverage industry. She started out owning and operating her own distributorship to most recently as an IT executive for Nestle USA.