Keith Cowing

Keith Cowing

Product guy. Entrepreneur.
Career advisor. Read bio

February 16, 2017


Building a happy and successful career takes time and energy. Try focusing on these four words to guide you in the right direction.


First, be honest with yourself. It’s amazing how easy it is to lie to ourselves. When you’re excited or upset, think carefully about your motivations, your loves, your fears, and your biases. We all have them. The more you understand them, the more effective you will be.

Second, be proactively transparent. Being honest is more than telling the truth when somebody directly asks you. If you go out of your way to educate people about what’s going well, what’s not, and what is at risk, you can proactively avoid a lot of problems.

Third, be open about your concerns and provide constructive criticism. Look at people who are extremely successful and you will frequently find this behavior. They give honest feedback, but do it in a constructive way so people can improve. If the train is about to go off the rails, you want somebody on your team who will raise their hand and tell you. Be that person, it pays off.


Kindness matters. The trick here is to carefully weave it with honesty. It’s easy to be honest and abrasive. It’s also easy to be kind and avoid criticism. It’s extraordinarily difficult to be kind and constructive at the same time. But if you can perfect this art, it will pay dividends throughout your career. If people know they can come to you for the brutal truth, but get it in a way that doesn’t attack them – you will become a trusted adviser.

The flip side is that you have to let go of the idea that you will make everybody happy. It is not possible. It is possible, however, to be honest and have the best intentions. If you are open, honest, and constructive then you can sleep well at night and accept the consequences. You will always miss something. You will always make somebody upset. That’s OK. It really is. It has to be or you will never make meaningful progress in this world. But have the best intentions.


The devil is in the details. Get your shit done. Send out status updates. Read the document before the meeting. Go the extra mile to close a deal. In the short-term, 9 out of 10 actions will go unnoticed. But people catch on and you will earn a reputation for being gritty and reliable. In the long-term, your results will speak for themselves. Success is 99% perspiration. Strategy doesn’t separate companies and careers. Execution does.


There is something magical about having somebody you can count on in the most critical situations. Pick your favorite sports analogy, whether it’s Tom Brady, Derek Jeter, Simone Biles, or somebody else. If you aspire to 10x your market value, you should aspire to be disciplined, prepared, and reliable. Poise under pressure is a result of consistent grit over an extended period of time. When you become the clutch player, you become a true leader.

November 2, 2016

phone screen materials

The interview process frequently starts with a phone screen. Follow these tips to make sure you’re ready.

Prep your physical space

If you might invest years of your life at this job, take the extra 15 minutes to make sure you’re ready for the interview. Plan exactly where you are going to take the call. That means privacy, little background noise, and either a landline or good cell phone reception. Also, have your resume handy along with a pen or laptop to take notes.

Rehearse your intro

Research shows that most interviewers make their decision within the first five minutes of an interview. This means you need to rehearse your opening. Again. And again. And again. Trust me. It’s work, but it is critical. The phone screen is similar to your resume, think of it like a movie trailer. Your goal is not to tell your whole story on the phone, but to entice them so they want to bring you on-site to see the rest. I recommend describing yourself in two to three unique sentences. Then use the rest of your conversation to prove those sentences true. Also be clear about what you’re skilled at, what you’re excited about, and how this role fits into your career goals.

Review your resume and ask yourself questions

Pretend you are the interviewer. Now read your resume and for every project and every bullet, see what questions come to mind:

  • What happened after you launched Project X?

  • What made this project a success?

  • What would you do differently next time?

  • What does this mean?

  • What role did you play on that team?

For each story, decide how strong your answer is and how relevant it is to your two to three sentences. If it’s a strong project, rehearse your response and discuss it proactively during interviews. If your answer is weak or not relevant, consider deleting the bullet.

Research your interviewer

Knowing your audience gives you a leg up. So ask politely when you’re scheduling the interview if you can have the name and role of the person interviewing you. If they decline, leave it there. But asking once is fine. If they give it you, use your research skills across the web to learn everything you can. You might pick up tidbits about what they look for, what they’ve done, what they’re working on, what hobbies they have, or where they went to school. You will not change any fundamentals, but you can tune your answers and conversation points so that you’re more likely to connect with the person.

Write down questions for them

The interview process is as much for you as it is for them. Picture yourself in this role. Would you be happy? Would you be successful? What factors about the company or the role would change the answers to those two questions? Turn those thoughts into detailed questions for the interviewer and write them down. It’s your life and your career, make sure you know what you’re getting into.

June 23, 2016

interview failure

You say:
I’m not feeling challenged in my role.
They hear:
My boss is giving the most important projects to other people and there is a reason for that.
I have gotten everything I can out of this role and am ready for something bigger. So I am exploring opportunities internally and externally and this role sounded really interesting.

You say:
No, I haven’t had a role like this before.
They hear:
I want to get hired, but there’s a large chance I can’t do the job.
I haven’t had this exact role before, but it looks like the key components are A, B, and C. A and B are exactly what I’ve been doing on Project Z, let me tell you about it. C is something I’ve been working on recently and am excited to learn.

You say:
No, I don’t know much about your products – an overview would be great.
They hear:
Choosing a job is one of the most important decisions in my life and I chose not to do my homework before this interview. If you hire me to run a project, I won’t do my homework then either.
I looked through your website, read your annual report (if the company is public), and saw some articles about Project X. But I can only tell so much from the outside so I would love to hear more.

You say:
I am really passionate about Education (insert appropriate market). No, I’m not interviewing at similar companies – just this one.
They hear:
If I truly had passion for Education, I would know a bunch of interesting companies and be exploring jobs at several. That means I’m either lying about my passion or lying about where else I’m interviewing. Neither option is good.
I’ve been excited about this space for awhile. I think companies X, Y, and Z are also doing interesting things so I’m looking at companies like them as well. But I’m particularly intrigued by this role for the following reasons.

You say:
Sorry I’m a few minutes late. The traffic/train/weather/etc. was terrible this morning.
They hear:
I am not reliable. This is one of the most important meetings I will have this year and I did not plan my day to make sure I’d be on time. When you have a critical deadline, it’s 50/50 that you can count on me.
Barring true emergencies (family situation, car accident, etc.) don’t be late! Seriously. If your trains and traffic are unreliable, get there an hour in advance and do work at a nearby coffee shop. If you are out of town and staying at a hotel, scope it out the night before so you know exactly where to go in the morning. Attention to detail matters. If you can’t arrive to an interview on time, why should they trust that you can deliver projects on time?

You say:
No, I don’t have any questions.
They hear:
If I was curious, I would ask a lot of questions. If I cared about the work environment, the team, and the product strategy, I would ask a lot of questions. But I have no intellectual curiosity and a low bar. So I have no questions. I just want a job.
Ask great questions! This is part of the interview. Identify the key things that matter to this business and drill in to learn more and see if you want to work there. You don’t need different questions for every single interviewer. It’s OK to repeat your questions and get multiple perspectives from different people. It’s not OK to have no questions.