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Ask Jason: How To Advance In My Career to CTO or VP of Technology

October 24th, 2019

I got a great set of questions from, let’s say, “Anonymous.” I’m going to edit the original wording a little, but not much.

I am a frequent watcher of your pluralsight videos (Jason Alba’s Pluralsight courses here). I am looking to move to the next level of my career as a VP of Technology, VP of Software Development, or CTO. I am currently [one level below those titles]. I am looking to build a roadmap to get me to the next level. A few questions I have are:

What do I need to master?

If we were talking in person I’d ask you a bunch of questions, most of which center around this role you want. My first CIO role was in a tiny company. I made up the title myself. I had CIO responsibilities, kind of, but there is no way I could have sat next to a CEO from a Fortune 1000 company and talked shop. I would have been clueless.

I was after the title. It was a good job, and great for where I was in my career. But a few years later when I was looking for a job (and instead started JibberJobber because no one would hire me) I couldn’t compete at the executive level.

So I’d like to know what kind of industries and companies you want to work in. Do you want to work in Fortune 500 or 1000, or in a startup? Do you want to work in a funded startup or a bootstrapped startup? Do you want to work in a bleeding edge industry or in more of the commodity space? Do you want to be in an environment where you have a staff of 500 people or 5 people?

The skills you need to master will depend on the answers to those questions.

I recommend having a pretty serious conversation with yourself about what kind of company, environment, and opportunities you want. As you do that you should get a shortlist of answers to the questions I asked… and from that list you work backwards.

If you have those titles at a really big company you might need to master more soft skills, like negotiation, leadership, communication, mentoring, strategy, etc.

If you are the titles at a fairly small company you might need a fair amount of soft skills, but you might be in more technical meetings with your small team, making technical decisions, than in executive level strategy meetings. I’m not going to say one is better than the other… but what do you think you’ll enjoy more?

I assume you have some serious technical chops. You have to, to be where you are today. You’ll have to maintain a degree of those technical skills, but you’ll probably want to really beef up on all things strategy and communication. Any executive should consider my Management 101 course boring… or at least, they should understand every single thing I talk about there.

Master learning. Master curiosity. Master human relations. Master hiring well and leading an A team. If you can master those things you will be a great boss and a valuable contributor.

JibberJobber Ask Jason

What do I need to improve?

It depends on what you are after, and where you are at right now. The answers to my questions above, and the results of an honest self-assessment should help you identify gaps in your skillset. Then, work consistently on those gaps. This is a marathon, so take it slow and don’t burn out early. Perhaps read a book a month, or every two months, on things you need to improve on. Go one step further and write about what you are learning. Whether that is through a blog (so everyone can see and learn with you) or a journal (so no one can see), I don’t think it much matters. But write. Critically think about what you are learning about. Practice. Teach. Mentor. Internalize personal growth.

I’ve talked about “the best time to plant a tree.” You will likely have opportunities come your way for the roles you aspire to. You might not be ready right now, but you can start preparing right now… and in 5 months or 5 years or whenever, you will be on the right path of the right preparation.

I am considering this my ‘Plan B’ option.

At first I took this line out of this post… but then I thought I really want to highlight it. EVERYONE should have a Plan B option. And a Plan C. I think I’m on Plan N or M… because A and B and C didn’t work out.

In our careers we have to be agile. We have to adapt. Please have a Plan B, and let it be fluid!

JibberJobber Plan B

I would like to understand where do I start and where is the defining moment when I feel I am ready to take the leap.

Honestly, you have already started. You started a long time ago, and your current title tells me you have done very well. Your defining moment will come at a time when you think “who me? Yes, I’d love to take that job, but I don’t think I’m the right person!” But, if you are on the path I talked about, and you are learning, and curious, and writing, and you are excelling in developing your soft skills, you are as much the right person as most other people.

Sure, there will be rock stars who are more qualified and better than you. But that doesn’t mean you should turn down opportunities. In my last role I suffered from imposter syndrome for months. It was weird because I normally suffer from a big ego. But there came a day, months in, where I thought “Oh my, I really do get why I’m here. And I’m just right for this job. I don’t know it all yet, but I’ll learn and I’ll contribute. And I will be known as a great hire, even if I have to fake some of this stuff until I get it.”  So maybe your defining moment will come a few months after you take the leap :p

In a follow-up email Anonymous says:

I am thinking about going to the local Technology Meetups, conferences, and networking events. But I don’t know if these events are going to help.

They will help you if you know why you are going, and once you go, you do the right things. When I started going to network meetings I was wasting my time. Or, honestly, I was learning. I went for me, and didn’t know why I was there other than that is what people said I should do.

Even though I’m a speaker at these types of meetings I tell people to not go for the speaker. Maybe you’ll learn something, or get inspired, but go because of what happens before the speaker gets up, and what happens after the speaker sits down. Go for the other people in the room. You should get personal branding benefit from going to these meetings. You should develop and nurture networking relationships. You should find opportunities to give to others, to help, to make introductions, and even to volunteer your time to the organization. Any of those are excellent reasons to go to network meetings and conferences.

I also go with a mindset of “competitive intelligence research.” That is, I want to know what topics are hot (look at the trends in topics… what is always talked about? What is new?) I want to know who the players are, how good the speaker’s messages are, and I personally go to learn more and better presentation skills. But if you don’t learn anything you should do some excellent networking at these meetings.

Who knows… maybe your next offers will come from people you meet at those meetings.

What are your thoughts about using recruiters?

I think recruiters can be great to help you land your next role. It is critical to understand, however, that unless a recruiter has an opening that is right for you, and you are right for their role, you are nothing to them. You aren’t even a number… you are just in the way to them finding their next hire.

I’m not ragging on recruiters. They would tell you the same thing… at least, if they were being honest they would. If you want to know how recruiters work, check out Nick at Ask the Headhunter. He has an excellent ebook on working with recruiters.

There you go… a little bit of this, a little bit of that. You have a fun future ahead of you. Continue in your preparation so when the opportunities come you’ll be prepared to jump!

 

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