Home » Career Advice

Category: Career Advice

Looking for career advice?

Let me teach you the best of what I know! My blog posts contain the best insights and lessons-learned from my years as a corporate strategist and product management leader in the high tech software industry as well as what I’ve learned in the past three years of coaching dozens of leaders at top-notch tech companies like Microsoft, Amazon, Apple, Google, Facebook and numerous startups.

Here’s Why Making A Radical Career Change Is So Darn Tough

Is there anything as hard as trying to navigate a radical career change?

From the time we are barely walking, we are being groomed to land a fruitful career. School, internships and part-time jobs are all designed to prepare us for what we will one day call “our career.”

This doesn’t pose a problem unless you decide one day that your career is no longer the right one.

Swimming against the current

There is no built-in social structure to facilitate major changes in career direction. Doing so requires a willingness to go against the grain, to not buy into the concerns of family and friends, and the capacity to work through powerful emotions that seem to pull you back to the secure job you once knew.

The other day a coaching client reached out with this exact concern.

He hired me to make a transition towards a different kind of life.

His previous career was that of a corporate ladder-climber. He was wildly successful. However, he was burned out and hungry for a better experience of work and life.

The goal was to craft a job based on his skills and interests; a solopreneur lifestyle that yielded income, joy, and a clear sense contribution. A full lifestyle redesign.

This was his decision and came out through several long coaching conversations and the client’s introspection after having a few months away from work to decompress.

The problem

A few months into his lifestyle design project, he got cold feet.

He worried that he was pursuing the wrong goal, that what he really wanted was to get back on the corporate “fast-track.“ The solution seemed to be, “let me just figure out how to run along the corporate fast-track while enjoying it and not getting stressed.”

My response was:

“Just relax and don’t jump to conclusions. See how it feels when you are actively working on your new business and creating a new lifestyle. If you have recurring and deep-rooted insights that you should return to your previous career, by all means, listen to those signals.

On the other hand, you might discover that the impulse to throw out the baby (your dream) with the bathwater (your past experience and future expectations) is just that, an impulse.”

Not every impulse requires a response.

This impulse, to rush back to the safer confines of the familiar life, is a common experience for anyone who is seeking to design their ideal lifestyle and vocation. Such re-imagination is bound to kick up a lot of emotional muck, including a healthy dose of insecurity (along with fear, guilt and yes, even boredom).

What happens when you get insecure?

Whenever I get insecure, I want to get a solid grip on the familiar, the safe and the secure (duh!). Just like when I was a kid learning how to swim, I would lunge towards the life-preserver impulsively. Eventually, I learned to ignore this impulse and trust my arms and legs to keep me afloat.

When my client got insecure (and redesigning one’s life will tend to do that) he wanted to retreat to the safe confines of the career environment he knew all too well, even though that environment was full of stress and no longer fit his values.

It was an impulsive move and a natural one. We all want to be safe and safety can be found through any number of places.

Three common safe havens are:

  1. Financial security.
  2. Recognition.
  3. Familiar environments.

My client was feeling a tremendous impulse to run back to his previous career, as it fulfilled all three of these safe havens.

It’s worth exploring these safe havens, as they aren’t nearly as “safe” as you would think.

Financial Security

Money matters. Though the specific amount you require to be happy is probably far less than you think.

When you get insecure, you will become money conscious and price sensitive. If you are looking to transition your career, and start feeling anxious, the salary prospects (and certainty of income) of a familiar job can loom large.

A sure-thing corporate salary will start to feel much better than the uncertainty of a new venture.

You will find yourself being pulled back into the orbit of your past line of work.


Recognition is just as important as money.

I learned this first hand as a manager in the high tech industry. While my team members all appreciated bonuses, I was amazed by the degree to which top performers cared even more about being sincerely recognized and valued for their work.

When we feel insecure, we gravitate towards environments where we feel appreciated and have confidence in our ability to perform.

This recognition can be found in the safe confines of a previous line of work.

Familiar Environments

Familiar environments are boring unless you are feeling nervous. Then, they become safe havens.

It’s in a familiar environment that you know the rules and how to play the game. It’s like having a home court advantage.

If you are feeling insecure about a career transition, you are going to feel like you should stick to familiar people, places and things. This can be a real monkey wrench for anyone trying to redesign their lifestyle.

What can we do about it?

Radically changing your career and lifestyle is hard. I’ve done it and still work through occasional (though increasingly rare) hunger pangs of a secure income, familiar environment and built-in recognition that comes from seeing the rungs I’ve climbed on the corporate ladder.

It’s also tough to figure out what you want, to look at the hazy mist of the future and plot a course into the unknown.

It’s even more challenging to make it happen.

The first step, however, is to strive for internal clarity.

Figure out your answer to the “what” questions. It’s a crucial starting point.

What do you want your life to be like? What career has meaning for you? What impact do you wish to make on the world? What learning curves are you excited to climb? Etc.

If you don’t know the answers. Relax, you are in good company.

All you can ever do is take your best guess based on how you feel in the moment.

Find a quiet environment and a calm inner space from which to explore your answers to these questions.

Then, as the mind is fickle and tends to forget, write down your answers so you can reference your thoughts the next time you feel nervous about how things are going for you.

Remind yourself of the life you are creating, why it matters to you and how you can serve the world as a result. Passion alone isn’t enough. We need a deeper purpose and meaning to our work and lives.

The good thing about insecurity is that while it’s the trigger for wanting to give up on a dream, it’s a fickle emotion that flees at the very moment you get busy working on something that matters to you.

So let’s get to work.

How To Have Amazing One On One Meetings

We are in a culture of meetings run amok. Most upper-level managers I know spend over 50% of their time in meetings. Even worse, research shows that 1/2 of all meetings are considered a waste of time! In spite of an environment where the tyranny of meetings is a new norm, I’m a firm believer that there is a certain type of meeting that is not done often enough, and when it is, it’s done poorly. I’m talking about one-on-one meetings.

Why One On One Meetings Matter

Human connection is the lifeblood of society. Relationships are at the core of what any business is and does. Your company is not a function of your product. Your company is a function of the creativity and productivity of people who choose to work there. One on one meetings are a way of taking care of the human connection in a way that people feel empowered with a clear sense of direction and an unwavering sense of safety and support from their leader.

This blog post is written from the perspective of the reader (you) being the leader. However, the insights apply equally to anyone who is looking to “manage up” and improve the way they relate to their bosses.

Before we get to what you should do in a one on one meeting, let’s talk about what not to do…

Please, Don’t Do This!

The worst use of a one on one meeting is to apply pressure and micromanage team members. No one wants to be micro-managed. If you find yourself issuing a litany of directives and checking in on the status of progress and tasks and other minutiae, you are not only missing a vital opportunity to coach your team, you are pushing them further away from their inner source of creativity and motivation. This is exhausting for everyone, including you!

It’s Not About You (The Manager)

Instead of using a one on one to tick off a checklist or spew directives, approach your one on one meetings with the opposite perspective. In my opinion, the purpose is to support the growth and development of team members.

Take care of project updates and administrative minutiae using email, use one-on-one meeting time to coach your team! If you, as the manager, do not have something to talk about, this doesn’t mean the one on one meeting should be canceled. The time is for your team members, not just yourself! Some of the best conversations happen when there is no “fire to fight” or project to micromanage. With a relaxed perspective and a willingness to explore, you would be amazed at what could emerge from even a short conversation.

One On One Meeting Structure: Three Questions

I like to think of three key questions to frame a one on one meeting. This is how I used to structure my one on ones when I was a team leader. You can be creative with how the questions are phrased, but ensure that each of the three topics are covered. I think you will discover (as I did) that this format of conversation helps team members to feel a strong sense of belonging and commitment to the team. You will also find that they help you (as a manager) to uncover meaningful topics of conversation.

Q1: What is going well?

Start on a positive note. Connect to something meaningful and supportive. Even in the worst times, there is always something positive going on. Encourage your team members to surface the things they are proud of. As a manager, don’t passively listen, but listen intently, to what is being said. If something intrigues you, probe deeply by asking powerful questions. For example:

“Tell me more?”
“What happened next?”
“How did you come up with that?”
“Interesting, should we continue doing more of that?”
“How can we expand the impact of that to other parts of the company/team?”

Q2: What would be even better?

We are all on a learning curve (perhaps several!) and face areas of developmental growth. No one is exempt; even Fortune 500 CEOs stand to improve in specific areas! Encourage your team to surface the things that they see as areas of growth. These may be challenges, missed opportunities or ideas for improvement in the future. If a project just completed and didn’t go according to plan, use this as a chance for your team members to reflect on what could have been better in their approach.

I like the phrasing of “What would be even better?” instead of “What’s wrong?” or “What isn’t working well?”. The former phrasing has a more favorable flare that people will be more receptive to.

As a manager, understand that it’s not natural for team members to want to share things that are not going that well, lest the messenger be criticized. It’s up to you, the team leader, to create a sense of safety in the conversation. Emphasize that you are really interested in hearing what could be even better for the sake of supporting their growth, and also, thinking broadly about how you can also assist in making things even better.

Q3: What, if anything, do you need?

Outdated management models dictate that team members work for bosses, who set goals, plans and allocate resources. Under this model, if things don’t work out, the fault lies with the individuals on the team who supposedly “failed to execute.”

However, flipping the management model makes a lot of sense for dynamic and modern businesses. After all, it’s your team that has a direct line of sign to your business operations, what’s working and where things could be even better. Why not allow your team to tell you what they need? Wouldn’t this both make your job of allocating resources easier and better serve the needs of your team and business?

I’ve discovered that just asking the question, “What, if anything, do you need?” holds remarkable power. It’s a coaching question that gets people thinking about their inner resourcefulness and what is really getting in the way of their taking positive action. Often, you’ll notice that they don’t need much to act on what you discussed, their awareness of what to do is all they needed!

Important: I am not phrasing the question as “How can I help?” Your offering to help might be needed, but should be offered only after your team member has tapped into their inner wisdom to solve their problems. Then, if they are still stuck, you might wish to ask if there is any way you can help. Just be careful not to “play hero” and solve everyone’s problems for them. Sometimes, I’ll let a team member sit with a problem for a while and then jump in only if I see that they are stuck. People can be remarkably resourceful if you allow them the time and space solve problems on their own!

Consistent Frequency

How often should you conduct these meetings?

Only discussing these points during an annual review is the sad truth about how many leaders operate. Consistency is key, though the exact frequency can vary.

When I led teams of 5–8 people working on diverse topics, I would meet with everyone weekly for an hour each. This made sense since each team member worked on radically different problems, and our team was moving at a very fast pace. A lot would happen each week!

If your team is aligned to work on a similar set of problems, or if the pace is slower; bi-weekly or monthly one on ones would make sense. Some global CEOs set aside quarterly one on one meetings with their direct staff members due to the extreme demands on time and travel. Experiment and see what works best for your situation. Whatever you decide, make it a consistent routine. Treat your one on one meetings as sacred time.


I hope that you are now in agreement that one on one meetings are a vital component of your management rhythm. I also hope that you have a clear sense of how to conduct them. The three vital questions I included in this blog post are a fantastic starting point for you. Try them out and let me know how it goes! If you have any further questions, please leave a comment.

5 Things You Must Understand When Making A Major Career Change

Making a career change can be tough. The longer you’ve served a team or company, the harder it feels.

My career change came after almost 14 years with one company.

While I held a half-dozen different roles at Microsoft, it felt like home. It was hard to leave. I literally grew up as an adult at the company. My best friends were made during my time there.

I don’t know if you are like I was. Perhaps you are earlier in your career and need to go in a different direction with your work. You might be later in your career, and ready for an encore. Different still, you might be out of work and looking to jump back into the thick of it.

Either way, what I know is there are a few key things you must understand when making a major career change. When you see these truths, the choices made will move you in a positive direction.

At least, this is how things have worked for me. It might work for you too.

Read more

How To Make Effortless Decisions That Will Propel Your Career and Life

decision making analysis paralysis

What decisions have had the biggest impact on your life?

In my life, there are a few that stand out. Where to go to college. Taking a job in tech instead of consulting or banking. Moving to Seattle. Getting married. Quitting my job to travel the world. Starting my business. Moving to Colorado.

When you think about your major life decisions, what was it like making those choices?

Was it hard? Was it easy?

Did you weight the pros and cons or just go with your gut instinct?

Every day we are making choices. Some seem big, and some seem small. Decisions can be exciting, but also a drain on energy and source of stress.

In this post, we will get to the heart of what decision-making really is, and find a way to make them less stressful and more effortless. I’ll specifically focus on two big mistakes we make. These errors keep us stuck and limit our potential.

If our destiny is shaped by our choices, moving towards free-flowing decisions (and away from analysis paralysis) is a crucial step to take.

Read more

The Truth About Your Advice: It’s Not As Good As You Think.

Do you love to dish out advice?

In my experience, without asking for it, people will throw their opinions around. Family members will tell you about the type of career you should have. Partners will tell you what clothes to wear. Friends will tell you where you should go on vacation or who you should date. Co-workers will give you career guidance.

Some people even go so far as to hire coaches to tell them what to do. I’m a coach myself, but I’m not in the advice giving business. I prefer to help clients discover answers on their own.

Moreover, the bigger the decision we face in life, the more we tend to turn to others to solve the problems for us. Seeking the advice of others seems like a smart thing to do when dealing with a critical situation. The problem is, nobody knows our life as well as we do. No one else has as much at stake. How then, can anyone possibly know what we should do?

The truth is that they can’t.

At best, giving and receiving advice is a way to gather knowledge. As the giver, it is a sure-fire way to stroke the ego. At worst, however, seeking the advice of others can lead you down the wrong path while shutting off the flow of your inner wisdom. When we tell others what to do, it constricts their innate intelligence and creativity. The same happens when we turn to others for the answers to our biggest problems.

However, what do we do when others come to us for guidance or when we are stuck in life? Should we expect people to figure everything out on their own? Of course not! However, you should handle these situations differently thank you think. By doing so, you will show others (and yourself) how to tap into the inner wisdom and capacity for problem-solving that we all hold as human beings.

Instead of doling out advice we should do this instead:

Read more

5 Keys to Rising Strong in a New Job

new job

For a moment, I’d like you to paint a vivid picture in your mind’s eye. Imagine that you’ve just survived a grueling interview process for a fantastic job. Everyone loved you. You get the offer and accept!

After joining the new team, you take your time to ramp up and learn. Slowly but surely, the days tick by as you struggle to learn the ropes and pick your big project to focus on.

Fast forward a year into the future, and you feel like you are stuck. Your last project was completed, but your boss didn’t seem pleased with the outcome. You are working hard but having a tough time getting things done. You don’t have the allies you need to push decisions up and across various chains of command. You don’t feel like you are on the same page as your management team.

Fast forward two years, and you know the jig is up. This role hasn’t worked out. While you aren’t being told to leave, you can see the writing on the wall. Before the hammer can drop, you decide to resign to seek a new challenge. It’s a bitter ending to what seems like a sweet once-in-a-lifetime job opportunity.

This story, as sad as it may be to travel through in your mind’s eye, is all too real for many highly qualified and determined professionals.

This blog post is designed to help you be among those who succeed and not the many who fail.

Read more

12 Things I Wish I Knew When I First Started Working

80,000 hours. That is how long you can expect work over the course of your lifetime. I’m well on my way, approaching the 35,000-hour mark by now.

I’ve done my fair share of work. First in the accounting department of an airline (not awesome). Then at an investment bank (surprisingly boring). Finally, I spent about 14 years at Microsoft Corporation (great place to work). Now I’m an entrepreneur (ahhh…finally!).

Over the years, I’ve learned a lot about how work can impact life and vice versa. I’ve seen what helps me get ahead and what holds me back.

I’ve learned what to do. I’ve learned what not to do!

If I could turn back time, there are plenty of things I would have done differently. Here are 12 things I wish I knew when I first started working:

Read more