Transformational Training as Lived Experience: 5 Questions for Heather MacDonald, Pluralsight

I spoke with Heather MacDonald, principal consultant for technology training and online learning platform Pluralsight, about how to align learning with the broader goals of an organization.

JC: Heather, you were previously VP of strategy at a midsized bank—what brought Pluralsight into your life?

HM: I was in charge of strategy, change management, internal communication, employee engagement, women in tech, workforce of the future, and data analysis for the executive team. I wondered, could I take everything I’ve learned and see how it applied across larger enterprises? I came over to Pluralsight to do this.

My career path has been everything under the sun: construction and retail, restaurants and nonprofits, big and small companies. This allowed me to identify many common patterns across multiple sectors.

Also, I wanted to make workplaces more equitable so everyone would have the opportunities I did. I started at the bottom. My first job was as a construction admin for my dad, who didn’t have the budget to hire a full-time professional. From there, I never stopped learning, never stopped taking on responsibilities, and always showed up so I wouldn’t let down the people who opened doors for me.

On paper, I am not the typical candidate for the job that I’m doing. I don’t have the education, certifications, or time in a Big Four consulting company. What I do have is decades of lived experience, and I think the same can be true for so many other people. They also need that first door to be opened for them, then the understanding of how to open doors for themselves. That’s what I set out to do across the strategies and programs I create.

JC: You’ve literally lived the experience of self-development and growth; that expression was made for you. How does your job map into practice? Is it individual customers, or is it broader?

HM: I mostly work with individual customers to co-create the right solution based on their program maturity and pain points. We look at things like, “What is the strategy for this specific client? What are they hoping to achieve, learning and development-wise, and how does that connect to the business strategy?” Then, we distill that into actionable steps to support the learning and development of their people.

Part of it is sharing broader thought leadership about what these strategies look like and what they are in practice. This could be writing blog posts, presenting on webinars, or hosting workshops both locally and globally.

Then some of the work is internal facing. Because my role touches everything in Pluralsight—I’m collaborating with sales, customer success, product, and other teams—we work together to figure out the best solution for our customers and how to help them achieve it.

JC: You touched on discerning the best strategies to help people. I’m a great believer in imposter syndrome—how do you approach arriving at a new company full of smart people?

HM: What I’ve realized in this job is that no matter which industry they sit in or how big they are, the issues people face are super common and sometimes self-evident. If you’ve worked broadly in business, you can see the bigger landscape.

The problem is that everyone wants a silver bullet. They want Pluralsight to fix 100% of their problems overnight. That won’t work, so we need to work through that. You need to spend time learning about the organization to help the organization learn and improve. I never want to be seen as a consultant who thinks I know better and only gives orders. I want to walk alongside someone on their transformation journey to ensure they can be successful.

It’s like learning to drive. You don’t hand the keys to a Lamborghini to a 16-year-old and say, “Good luck, have fun, and I’ll see you in an hour.” They need to learn the book stuff, then go on the range and drive in a controlled environment. But people want to give you their Lamborghini and say, “Go ahead, figure out my entire company.” Even if you’re a great driver, you don’t just start driving and understand there’s a problem with the alternator, or that you need new tires.

In general, though, we do see patterns repeating. For example, we’ve all worked in places where change strategy starts at the top, and the executives and often senior leaders fully get it; they are bought in. But you hit layers seven, eight, and nine, and those people have no idea why they are here and why they matter. “I’m just a cog in the wheel,” they think, so how can they be bought into company-level change?

From a strategy perspective, it’s about stepping back and saying that if you as a business aren’t working through change management and communications effectively, none of this matters. You’ll never get anywhere if you can’t communicate down, up, and across. You need to create the environment and safety for the changes your organization needs to make.

At the pace of technological change and evolution, we can’t expect any one person to know it all anymore. We have to step back and say it’s more about collaborative and real-time learning and making sure people can fill the needs they have today. That’s where mentorship and practitioner support come in.

JC: Often, new organizations haven’t done the masterclass of business growth; they’re learning on the spot. Meanwhile, bigger companies are not able to change. They’re siloed. It’s less about telling them how to do the stuff they’ve been doing for 20 years and more about helping them understand how to align with the new. We all need that collaborative, transformational stuff. You don’t learn the theory and then suddenly change.

JC: Darrel Kent, one of our lead analysts, said that when he’s helping newer organizations, they’re learning old principles for the first time—how do you address that?

HM: It’s not the fault of executives who have been in business for decades. What worked back then was to go to school, get a degree, get a job, work your way up, and you could afford to buy the house with the white picket fence, drive the nice car, and feed your family on one income. Legacy industry execs, like those in banking, utilities, and telecom, sometimes feel like what worked for them should work for everyone and don’t understand why folks are pushing for more remote work and different benefit options.

With all that has happened in our world, we’re in a time where that plan for career success doesn’t work anymore. You can get a good job and still not be able to buy a house, buy a car, or afford a family. You can go to a top-tier school and still not get a job because you don’t have the experience. We have to honor where you’ve been and acknowledge that if we want to remain competitive and grow, we must make incremental changes.

We can’t expect every executive leader to understand how to navigate a fully hybrid and remote environment. That is challenging for people who are used to doing it one way because that worked for them before. So, how do we support the top layer of executives and leaders to learn the skills and capabilities they need to continue leading companies? We need to set egos and titles aside and realize we’re all learning through this. We need to step back and collectively figure out how the world of work is going to look going forward, and honestly, it’s likely to keep changing over time. Anyone looking for a static way of leading is going to get left behind.

JC: I have to say I am slightly disappointed it’s not old guys smoking cigars and sitting in big leather chairs dictating letters anymore! I was looking forward to that.

HM: Ha! I still encounter people who say, “Could you fax me that agenda?” No, you can open the attachment. It’s one page with three bullet points. “Oh…can you print it?” No, we’re saving trees today. This agenda doesn’t need to be put in a filing cabinet.

JC: Given quick fixes aren’t an option, how do you put a strategy together that will work for such a range of people?

HM: I tell people considering our service that we’re not consultants who tell you everything you’re doing was wrong and then disappear. We help you start to make progress toward your transformational change goals. By nature, transformation does not happen overnight. It takes time, effort, and evolution.

We go back to basics and the foundation of OK, you’re trying to upskill a workforce. The disparity between your organization’s least and most technical person is probably massive. So, how do you get everyone on the same page?

It’s not the same for every organization, but you can figure out what will fit most people. Some, who are reasonably skilled and have a decent amount of time, can self-select into a program. Then, figure out the outliers, the people who are super far behind or ahead. What do they need to be doing? It will require different solutions for them.

In cybersecurity training, for example, maybe your warehouse teams need the most attention today because someone clicked on a phishing email and caused a data breach. You need to think about what cybersecurity training looks like for people in a warehouse. What works as cybersecurity training for people in an office setting is not going to be the most applicable, or effective, way to train people in a warehouse or who have roles that aren’t tied to a desk.

Even if you are reasonably technical in your role, that’s no protection. We have to make sure everyone understands that one bad email could take down your entire company. We don’t want people to be scared and paralyzed, but we want them to have a strong enough sense of awareness that they don’t click on the thing that could be a bad link.

Even cybersecurity professionals at the top of their game who have been doing this forever are having to adapt because everything keeps changing. Attacks that happened yesterday are not the attacks that will happen tomorrow. There’s constant anxiety of, “Am I going to be the person that misses the thing that takes down my company?” That group needs a different level of tech skills development support and engagement to ensure we’re not burning out the people who need to be well rested and prepared if things go wrong.

JC: Oh, this resonates. When I used to do security awareness training, we tried to help people think a bit more—about leaving passwords on a Post-it, for example. There’s more to learning than pointing people at a training manual.

HM: Yes, indeed, it’s the 70-20-10 model for learning. 70% of learning needs to be hands-on and experiential, like labs, job rotations, and stretch assignments. 20% of it should be social learning like mentoring, communities of practice, coaching, or buddy systems. The last 10% is formal learning, videos, books, college courses, and certifications. Formal learning is good for gaining knowledge but doesn’t translate into wisdom until you put it to work.

If you can’t contextualize what you’ve learned, you’re book smart. With that 70%, you can fill the gap between “I learned a thing” versus “I know what this means within the context of my role, my business, the economy, and the world around me.” It’s the difference between learning something and bringing it into your own lived experience.

JC: Thank you so much, Heather!

HM: My pleasure.