C-suite career advice: Jason Cohen, WP Engine

What tips would the c-suite give to the next generation?

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Name:  Jason Cohen

Company:  WP Engine

Job Title:  Founder / CTO

Location:  Austin, Texas


What was the most valuable piece of career advice that you received?

The way to get promoted to a new position, is to already be behaving like leadership and doing the work required by that position.

For example, as you move up the management ladder, your job becomes more about connecting with leaders across the business rather than staying focused on execution within your team. So, one way to start behaving like an executive is to establish relationships with peers or leaders in other departments. This can mean personal one-on-ones, lunches, or project-based reasons for working together. When you're in those meetings, rather than try to show how great you are, be direct and find out what is important to the other person -- what are their goals, challenges, etc. – so you can figure out how to help others through your team's efforts, or at least be mindful of what others are going through. This mindset of trying to help the entire company succeed, rather than the success of the teams you manage, is an example of behaving like an executive instead of a manager.

There are of course many other examples. By understanding what it means to do the work of a new position, and trying to do that work today, you are demonstrating that you are ready and willing to be engaged.


What was the worst piece of business advice that you received?

"Don't bring me a problem unless you are also bringing me a solution."  

We've all heard this. I hate this advice. I hate it as an executive because it means people won't surface problems. Often problems are clear, but solutions aren't. Why should the person who is prescient enough and brave enough to put their finger on a problem, also be required to solve it before they're allowed to speak? Why shouldn't we engage the right set of people in forming and then executing a solution?

I believe the intent of that statement is: Don't just complain; be constructive. That's sound advice, but of course it's possible to be constructive while also not yet knowing how to solve the problem.

Another intent is: Don't just drop problems into my lap; be a part of the solution. That's true too. If you treat your boss as the only person who can solve all the problems, then they are the only person who can solve all the problems, but only because you've abdicated that responsibility. Don't abdicate!  If you can formulate and bring a solution, do that!

But, the thorniest problems probably don't have clear solutions. Yet, those are exactly the ones which need to be surfaced, so that the team as a whole can create a solution. Don't bury the hard problems!


What advice would you give to someone starting their career in the tech industry?

The good news is there will only be more opportunities and jobs in tech, ranging across all geographies, skill levels, and specialisms. The bad news is, everyone else already knows that, so competition can be fierce. Therefore, know your unique strengths, and bring those to bear as you navigate your career.  


You will most likely be competing with people who have been writing code since they were eight years old. However, your own skill sets may lie elsewhere. For example, you might have a strong IQ or be a great mentor. You could be a fast learner. Flexibility might be your thing or perhaps you’re able to communicate and work well with people in specific departments outside of engineering or IT. The list goes on.  

The fact is, there are many ways in which someone can be valuable for a team and an organization. Being technical and writing code is one of them, but there are many. Focus on your strengths and bring those to the workplace, in your interview, in your work, and to your team members.

Success has many facets!


What tips would you give to someone aiming for a c-level position?

Be certain you want the lifestyle of a C-level position.

It's easy to say "yes," because of the perceived ego boost of being able to say, "I'm a C-blank-O" at a party, the stock options and cash compensation associated, or thinking about your impact on the direction of the company, your department, and the overall success of the organization. Which aren't entirely bad reasons.  

But it's not the whole story.

According to the Sword of Damocles story, Damocles was flattering his king, Dionysius, and exclaimed that Dionysius was truly fortunate. He was a great man of power and authority, surrounded by magnificence. In response, Dionysius offered to switch places with Damocles for one day so that Damocles could experience that fortune firsthand. Damocles eagerly accepted the king's proposal and was sat down in the king's throne. However, Dionysius had arranged for a huge sword to be hung above the throne, held at the pommel only by a single hair of a horse's tail. Damocles finally begged the king that he be allowed to remove himself from the throne realizing that with great fortune and power comes great danger.

The flip side of having a huge impact on the company, is that you have the capability to destroy millions or even billions of dollars of value. You could be responsible for having to lay off hundreds of people. You’re tasked with finding solutions to the problems that no one can fix. Everyone is watching you, all the time, so if you're having a bad day and look upset walking down the hallway, that turns into a rumor about how something must be wrong. An executive has to constantly be aware of their mien. When things go well, the credit goes to the team, and when things go poorly, the responsibility is yours. Even the best executive teams struggle with stress – with dysfunctional teams it's a daily struggle of politics and personalities.

Being an executive is also a 24/7 job. The reality is, no executive at a public company has ‘work/life balance.’

It can be difficult to understand the negative side of being an executive, because the public face is always one of confidence, strength, and ease. But nothing could be further from the truth. Perhaps the best book on this subject is Ben Horowitz's Hard Things about Hard Things. Read that book, and if you're still not just interested but excited about being an executive, then it's probably the right path for you.

Otherwise, don't let the allure of ego or even compensation trick you into a career that ultimately will make you unhappy.


Are you particularly proud of any career advice that you’ve given or the career route/development of anyone you’ve mentored?

I'm proud when someone finds their true calling and pursues it, whatever that may be, and no matter what others may think, as long as you have a sensible plan and rational determination.

The popular thing to do has been to either switch departments, switch careers, or determine that you love teaching people rather than making the most money. Often, people believe they have to become a manager to further their career, instead of realizing that managing people could make them unhappy. For them, it could very well be that being the best at their craft is an even better for their happiness, but still enables them to increase their compensation and the respect of their peers.