Make sure to check out the previous post: Advices I wish I got at the start of my career.

Ask for help

Son, your ego is writing checks your body can’t cash.

– Captain Tom “Stinger” Jordan, Top Gun

The number one reason why senior people fail is that they do not ask for help. We are all shareholders. You do whatever you can to unblock yourself. It is about time to market and showing results.

Promote thought leadership

If you want to build a ship, don’t drum up the men to gather wood, divide the work and give orders. Instead, teach them to yearn for the vast and endless sea.

Antoine de Saint-Exupery, author of The Little Prince

In tech, most decisions are based on influence, not hierarchy. Thought leadership is a great way to gain influence. To be a leader, you should start by acting like one. Be confident, give tech talks, and voice your opinions in planning, design review, and postmortems. Doing so makes you the obvious choice for the next big project or the next leadership roles.

The outcome and how you drove that outcome are both important. Be careful with your reputation.

Befriend Jeff Bezos before he gets rich

The best time to become friends with Jeff Bezos is before he becomes rich and famous. Networking does not mean you must reach upward. Invest in your peers, who are more receptive to getting to know you. Imagine you are Stripe in 2012. Rather than running into walls with F500 enterprises, you should onboard hundreds of startups, because among them are the next Airbnb and Lyft. Relationships compound. Start early.

Do informational interviews. Ask people at other firms what they like and don’t like about their job. Always follow up to maintain weak ties, such as

• Saying hello to someone you met at a conference last year. Or asking if they’ll be attending after this year’s agenda is published.
• Share interesting news about your old company with a former colleague.
• Send them news, event, commentary related to their interests. Examples:
  • “Tom, I just read this great white paper on blockchain. I know you’d get a lot out of this.”
  • “Alice, congrats on the new job. Enclosed please find a copy of the best book I’ve read on starting a new job, The First 90 Days. Call me if you want to compare notes.”
  • “James, I just got an invite to a private class at this new gym but can’t go. You mentioned you love Crossfit — want my ticket?”

Stop productivity porn. Bias towards action.

Watching others lifting weights is not going to make you fit. Many of us spend so much time collecting books we want to read but haven’t, or studying how others slice up their days to get more done. You get more done by doing and by starting now.

Develope relationship skills

A major reason change efforts so often fail is that successful implementation eventually requires people to have difficult conversations … With everyone taking for granted that their own view is right, and readily assuming that others’ opposition is self-interested, progress quickly grinds to a halt. Decisions are delayed, and when finally made they are often imposed without buy-in from those who have to implement them. Relationships sour. Eventually people give up in frustration, and those driving the effort get distracted by new challenges or the next next big thing. The ability to manage difficult conversations effectively is foundational, then, to achieving almost any significant change.

– Douglas Stone, Author of “Difficult Conversations: How to Discuss What Matters”

Relationship problems are at the heart of every organization. Take product managers (PM) and engineering managers (EM) for example. PM & EM have overlapping scopes by definition. When you seek better scoping, you don’t have a scoping problem, you have a relationship problem.

Here are some tips:

Be a good listener. People rarely change. People just want to be understood. Listening is more persuasive than talking. Listening fosters a reciprocal relationship. Listening is not just about paraphrasing back. Ask deep and relevant questions, take notes, and maintain eye contact. For many, listening needs to be a trained response. When you are frustrated, you are the least curious—you have so much noise in your internal head that left little space to worry about what’s on the other person’s head. Learn to lean into the conflicts, just like firefighters learn to run towards the fire.

Lean into conflicts. Avoiding conflict is the worst kind of measure of relationship health. Staying quiet creates resentment. You must confront, but do so with skills and preparation. It is mature to share your feeling and inquire about others’. Doing so builds trust. For example: “Bob, I feel frustrated. It seems this conversation is not getting anywhere, and I want to understand why.” Acknowledge the differences between the two parties, not who is right or better. I love this example “Jill, you and I seem to have different preferences about when code reviews should be done. I wonder if that’s something we could talk about?”

Resolve email conflicts in person. If a conflict starts on email, it is hard to solve on email. In this case, just meet in person or pick up the phone. It is hard to communicate emotions through email—no tone, no voice, no facial expression, no body language.

Apology diffuses the tension. In most conflicts, blaming does not help. Most of the time, you share part of the blame, even just 5%. Apologizing and acknowledging the fault on your side could really diffuse the tension. Apology is an underrated and underutilized skill. Apology needs to be genuine. Saying “I am sorry that you feel that way” is not genuine. Here is how to make a good apology:

1. Acknowledge the harm. “I am sorry that I interrupted you in the meeting.”
2. Say why it is wrong. “It was disrespectful and discourage the full exchange of ideas.”
3. Say what you will do next time, not what you won’t do. “I will make sure to let you finish before I chime in.”
4. Ask for forgiveness. Bring cupcakes.

Go straight to the job you want

Don’t let inertia drive you. Take some risks when you are young. No one in their 40s said they took too much risk.

If you are unhappy about your job, move on. Every job change you make, you always wish you make it 6 months earlier. Life is so short. Do not spend time on jobs that you do not like. You will be so productive in jobs you like. Don’t assume that you have to do this job, then get that job and then that job, and then you can do what you really want. Go direct.

Know your alternative. Negotiate hard on your second best offer, then negotiate with your first choice, knowing what you can walk away towards. Pay attention to details. Be specific about equity grant date, vesting schedule, etc.

What to look for in the next job: Growth

With the right opportunities, you can 10x your impact every decade. Because of compounding, what seems to be golden handcuffs today is dwarfed by the opportunity to accelerate growth. The exponential curve actually consists of many little S-curves. If you find yourself approaching the flattening end of the S-curve, it is time for a change.