How to keep your job as CTO
By: James Williams
Tags: Technology, Cio, Technology Management, Cto, Chief Technology Officer

How to keep your job as CTO

And, the 4 things you must know

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If you are a CTO, you need to see yourself as an executive. If you don’t, you will be fired.

In this blog, I give advice I failed to follow at the beginning of my career. It is advice, once followed, that propelled me to the top. Not only was I able to help take a company public, but now I run a successful consulting business. I use the same principles found in this article.

The meaning of CTO

Operating at the CTO level is the most counter intuitive endeavor you will ever take on.

If you are moving from a start-up CTO, to a larger company, it’s worse. It turns out that a computer science degree does not teach you how to deal with a board room. I’d venture to say, that no focused degree does.

How are you navigating your board today? Do you have a strategy? How do you reach out to customers on your own? How are you building relationships?

What’s the last thing you sold internally or externally?

I am willing to bet that some of the most talented CTOs have not thought of any of the questions. I know I didn’t.

So, here is are the 4 things you need to know to keep your job.

1. You are a sales person

If you think your job is just the technology you have already failed. It’s easy to convince yourself that focusing on your technical duties is your only job.

And, if you build the best technology and make all the right decisions, then your obligations as CTO are fulfilled.

Wrong!

Throw out everything you thought and read carefully.

I have been on the chopping block countless times with that approach. And when I was on the outs with my colleagues, I didn’t even know. I found myself confused, because I had done what I was trained to do. I did the work until 4 AM. I studied. I read white papers. I responsibly did the job.

After all, I know best-practices. I understand algorithms. I can code. I create architectures. I know engineering culture and how to build teams. I can do cost analysis, and I keep up with the latest trends in tech.

So what!

The Executive role is not a meritocracy

I mean we all know the world isn’t a meritocracy, but somehow we still operate that way. Is this you?

You win when you get buy-in internally. You need your talents plus a relationship with your colleagues. If done correctly, you are working as a team with your board to achieve business objectives.

How do you know if your board sees you as a vital part of the decision team? If you are hearing what your board wants from someone else, you are not in the inner circle. And, if you are not in the inner circle, they are not sold on you.

Making friends with your colleagues

To get buy-in, you need to sell. I am not referring to a used car, sleazy salesperson. I am talking about doing the job of a true executive.

You want to have a relationship with all departments. From finance, to business development, to sales, customers and customer support. They all need to know how your engineering team helps them.

If they don’t, in the quiet corners of the office, they will systematically pick you apart. Or, they replace you. Another common tactic is to hire two of you.

Here are a few things you don’t want said about you.

She really doesn’t understand the business. She’s just tech.

I am not sure she knows how we make sales here.

I don’t really see her as an executive. She’s not executive material.

She’s really good at running her team, but I am not sure she even knows what our customers want.

She’s not <Insert your respective domain expertise here>

If these things are said about you, you haven’t sold you to your colleagues. Stop thinking of sales as a negative term and get good at it. Your job depends on it.

And the end of this article, I give my CTO life hacks.

2. Be willing to quit everyday

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To be effective you have to operate at an elite level. To use a sports analogy, you have to leave it all on the field.

The bottom line is, if you are worried about keeping your job, you will lose it.

A great friend of mine and executive coach always said, “you have to be willing to push your poker chips in the middle of the table.”

And if you don’t, you get zero respect.

Playing politics

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Many business people will be accustomed to navigating politics. Unfortunately, this is all some will do. They will understand their jobs are part sales and politics. They know they can’t focus on the goals of their job title unless they navigate the politics of their organization.

The meritocracy approach will leave you out of meetings. You will find yourself gazing through the glass of a conference room. You will wonder, “Should I be in that meeting?”

You will find yourself at the bottom of the cap table. It is highly likely that you will see decisions made for you.

I have learned through the years, to champion my initiatives. And, to take a firm stance on what’s important for the people I lead. It finally occurred to me that I represented not only my team but also the company.

A common mistake is to get a CTO job and still behave like a team lead.

My point here is, you want to possess that swag in your walk that says, “ I deserve a seat at the table.” But, you have to do the work.

Think like an athlete.

3. You must constantly negotiate.

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Every conversation you have, no matter how small, is a negotiation.

You have to listen to what your colleagues want. What helps them? Make sure they know you understand what technology means to them.

It’s not about sprints, and the folklore of container strategies. Save those conversations for the water cooler and your friends.

You need to understand the sales funnel and what you can do to help. And, because you can’t do it all, you have to negotiate.

Ask how, when and what questions. Find out when feature X is really needed. Learn the impact of this feature. Try horse trading.

Ask things like, “If I give you Y now, does that help?” Provide options that solve their problem rather than having a bias to NO. Give them a timeframe.

It helps to make internal informal contacts. In the past, I have written SLAs for each department. This gave them an understanding of what my team could do, and our limitations. These SLAs were written in business terms, not Agile stories.

You will find if they know what you can do, they will work with you.

4. It’s your fault if they don’t understand technology

A huge mistake is to assume that other departments understand your pain. Somehow, they should know that your engineers don’t want another death march.

Or, you convince yourself that how the company ended up with technical debt matters. They have jobs too. And, it’s likely that you each need one another to be successful.

It is your job to make sure they understand.

Ask yourself, how will doing an architectural feature impact sales? How can you accelerate sales with a bug fix? Is it possible to team with your sales team to figure out a win-win?

You must put effort into explaining things. One hack I used is to use my own designer to draw pictures. Basically, I created info graphics and I took the time to sit down and explain it.

I learned that if I wanted to be thought of as a partner, I had to treat them as equals. Just because they don’t code, doesn’t mean they aren’t smart.

My CTO Tips

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Here are a few hacks I have learned over the years. Some come from colleagues who were just smarter. Others come from years of being coached.

Have weekly one on ones with key leaders of each department. They can be as short as 15 minutes. I used to take my CFO for steak once a week. It was cheap steak, but steak nonetheless.

They can be as short as 15 minutes. I used to take my CFO for steak once a week. It was cheap steak, but steak nonetheless. Establish your own relationship with customers. To stay connected, you must know what your customers really want. You cannot afford to get second hand information about something so essential. I invited customers to some of my engineering sessions so that we could learn from them. We all have one engineer that shouldn’t be in that meeting. It’s still worth it.

To stay connected, you must know what your customers really want. You cannot afford to get second hand information about something so essential. I invited customers to some of my engineering sessions so that we could learn from them. We all have one engineer that shouldn’t be in that meeting. It’s still worth it. Present all the issues you know, first! Many times, I found that someone in the business didn’t understand me because I didn’t understand them. Even if I couldn’t do anything about it, I didn’t hear their pain. It goes along way to listen. If you don’t repeat the pain back to them, then they assume you don’t understand.

Many times, I found that someone in the business didn’t understand me because I didn’t understand them. Even if I couldn’t do anything about it, I didn’t hear their pain. It goes along way to listen. Write SLAs. Set expectations on when bugs can be fixed. Let them know how and when features will be released. Share the same SLAs with your team. In fact, I would have my team write then approve them. You will create alignment.

Which one of these tips will you use? Do you have tips that have worked for you? Share your comments.