Cengage Group CTO Jim Chilton on the P&L difference

Contrast your journey with those who end up getting pigeonholed. Why do some people get overlooked for new roles or opportunities without knowing why? 

I think it has a lot to do with the willingness to be vulnerable about what you’re looking for while also being clear about what you expect for the work that goes into it. I’ve seen some people will do a few things and think they’ve earned the right. You have to be very clear about the expectations of your role, and demonstrate how you have fulfilled those multiple times. Saying you had one good year, one good project, one good implementation is not enough. It’s not enough for the types of conversations where you say, trust me with your $200 million acquisition. You have to earn that.  

It’s also about patience and being comfortable and vulnerable enough to ask for additional things to do. The risk in saying, ‘I want something more to do,’ is that the receiver of that information, your CEO, may be like, ‘You don’t like your job?’ ‘No, I love my job. I do my job well. I’ve done all these things. I’ve talked about my successes and the things that the team and I have done. I want to do more.’ 

It’s also saying: ‘I want to do more on my time. I’m happy to take this on and do this. I’m going to go from a 40-hour work week to an 80-hour work week because I want to do this and I can be someone who can help make a difference both for the company and for this organization and this acquisition that we made.’  

Too often I see people that want more, and before the more even starts, they want to know how much more they’re going to get. They lead with, ‘I want more and you should pay me more or give me more equity or do this or do that.’ It’s my belief that when you work hard and do these things, good things will happen, and you will be rewarded and recognized. That’s why you’ve got to believe at your core that you want to do this and that the value of these experiences will extend beyond the current role. Make sure that you’re doing it because you care, you want to learn, and you want to develop. 

I’ve never liked that expression ‘fake it ’til you make it’ because I think it sends the wrong message. I think a better message might be ‘grit it ’til you get it.’   

I’ve seen disastrous things happen for people that fake it ’til they make it. At Dassault Systèmes, I watched some incredible people come in as interns from great universities, super bright, they pushed and clawed for more money, more titles, got all the things they wanted, got frustrated when they finally couldn’t get more money or more titles and they left the company. Then they discovered that they couldn’t do that job at that level, and they lost that job — and then they discovered, again, that they couldn’t do that job at that level. And now they’ve got two or three back-to-back blemishes on their resume. No one wants to hire them at that level; no one wants to hire them below that level. They have painted themselves into a corner.  

I’ve watched those people claw their way back decades later, finally earning their stripes to that actual title, and what a painful process that is. The managers of those people failed them by promoting them and giving them a title way too soon. That’s a responsibility I’ve taken seriously, and I know some people on my team love me for it, and some probably hate me for it. But I think you owe it to people to set them up for success.  

For those who are coming up in the IT ranks today, why should they seek out a role in the business? 

It’s a great opportunity to do two things: First, to differentiate yourself. To show you are diversified and broad enough in your thinking that you can do more than the track you’re on. Diversification and differentiating yourself as a candidate is super important and you’re going to learn a ton of things.  

Second, you will be far better at your job as a result. When I was the general manager of Infosec, we were having challenges around lead generation, and there was great technology that we could put in place that would allow us to generate leads more rapidly. When I put my CTO hat on, those were rules that would break my policies about how we would generate leads. The general manager of me is like, ‘I absolutely want to use this technology because it will allow me to accomplish my business objectives.’ As the CTO I’m like, ‘You can’t use that technology. It’s against our values and principles as a company.’  

It allows you to get in the other seat so when you’re going back to that CTO job and you’ve got a business unit leader standing in front of you telling you they desperately need to be able to do something, you have a completely different understanding about the pain that they are feeling and the understanding that you have to give them because you’ve lived the experience now.  

Finally, this experience is becoming ever more critical to being a good CTO or CIO. The expectations for executive-level technologists today are very different than when I took on my first leadership role. Now, if you sit at the table, you represent the whole business, no longer just your function. The company, the CEO, and your fellow leaders are depending on your guidance on technology, cybersecurity, and risk. Today’s CIO/CTO must bring the technology expertise to the table, while also demonstrating strong business and leadership skills.

This has become a multidimensional job. Being a great technologist who created a great product or solved a problem for company X is no longer adequate. You must be able to create a vision, inspire teams, show relevance to their work and business outcomes. This can be a fascinating role where you can participate in nearly every dimension of the business to truly leverage technology as a differentiator.  

Would you say that’s one of the ways you’re a better CTO today, because of this P&L experience? 

The level of appreciation and understanding I have for the business and the leaders in those businesses — I mentioned Alexander Broich, who’s one of our general managers — I have an incredible amount of respect for him after working with him on Cengage Work and Infosec, a whole other level of understanding from watching these folks who have been doing this type of work their whole life. The same with Balraj Kalsi and Michael Hansen. Just incredible intellects in the work that they do, and learning from them is a humbling experience. My blind spots were things that they saw right away.  

As I go back into the CTO role, it allows me to have a ton more respect for the people that are running those businesses and the challenges they are faced with, but it also gives me more context for what the team and I can be doing to help us be successful in those endeavors, with a whole different perspective on what challenges exist for these business leaders. When we’re talking about standards and compliance and governance and all of these things, to understand that just complying and responding to our requests may be a burden against their very existence of trying to grow that business, grow the revenue, grow the EBITDA, really improve that business. We’re sitting there pestering them about something that they may see as far less relevant. So our job is really helping them understand why it is relevant, why this can help you, and how this could be an unlock for the business. 

For more insights from Jim Chilton’s leadership playbook, tune into the Tech Whisperers podcast.