How To: Be A Good Employee, Be A Great Boss | #winningcareers

Like many of you, I am both an employee and a people leader.

At different points of the day, sometimes from one minute to the next, I have to switch gears so that I can be fully present as both a good employee and a good people leader. This constant quest for excellence, from one email to the next, from one meeting to the next as context changes is… taxing.

From observing behavior closely, and from my own experimentation and failure, I've noticed consistent patterns in what great employees do and great bosses do. In my long professional career, I’ve tried to emulate these patterns and to build on them as I try to deliver a non-normal impact to my employers.

While obsessing about Marketing and Analytics here on Occam’s Razor, I want to share the habits and behaviors encoded in these patterns so that you can have a non-normal impact in your chosen field as well.

[At the end of this post, you’ll find my guidance summarized in a printable infographic.]

I’ll cover the ten good employee patterns:

And follow that with six great boss patterns:

Ready to boost your career to a new orbit?

How to be a Good Employee.

1. Never bring problems.

Even if you are a fresh intern, never bring problems alone to your boss.

For any employee – at any level of seniority – I do not expect (as a people leader) that you will know everything, or that you will be able to articulate the perfect solution to any problem. But, please bring a solution(s). Or recommended next step(s) that you feel are a way out of the problem you've identified. At a minimum, succinctly describe the context, i.e., what have you already tried, and why won’t it work? Help your boss out.

At the very least, a boss has 18 other things on their plate at any given moment, 5 to 40 other employees to worry about, and 3 big things that are 2 weeks late already. When you bring a solution(s) along with the problem, in addition to demonstrating empathy, you've gifted your boss some starting points for a productive conversation.

It is also an excellent demonstration of your proactiveness (especially if you explored some of those solutions with others in the team or other stakeholders). It also shows ambition. It shows you are different. This is invaluable.

[Bonus Tip: When you present your solution/s to the problem you’ve identified, be sure to explain the framework you used to think of. The solution may or may not be great, getting your boss’ feedback on how you think is super-precious. And, great bosses love frameworks! (See some of my favorite frameworks in item #4 in the boss section.)]

2. Be thorough.

Our time is so fragmented. Our lives are so stretched. Even as I'm writing this post at midnight work emails are flowing and I'm trying to be a good employee/boss by responding with value-added perspectives.

The first casualty of fragmentation is that an employee becomes a surface skimmer. This is the person who takes in just the minimum amount you need to complete a task. It is so damn easy for the corrosive tl;dr to become your fundamental approach.

I love people who are thorough – and I’ve always tried to emulate them.

They do more research than is required. They talk to one more expert than I expected. They find the external author of the statistical algorithm I want them to use, and ask them for guidance. They proactively end up taking free training courses. They instinctively ask for assumptions in any dataset/argument (I adore this!). They go deep into problems to identify causal factors and not correlations – which is why their solutions have a non-normal impact.

This is hard to do. It takes time and a lot of conscious practice. But, If you choose to do it, you'll be an outlier amongst your peers.

3. Care about little things.

Caring about little things is a different way to demonstrate your competence – and attention to detail.

As a people leader, I should not have to spend 30 minutes fixing alignment in your slides. Or, check for spelling errors. Or, request that you fix shifting altitudes in your analysis (a true-crime!). Or, request that you tailor the analysis for the audience/s (context!). Or, remind you not to be on your phone in a team meeting. Or, triple-check the formulas in the analysis from the Agency. Or, tell you there is already a tool that does what you want to build.

Look, I’m happy to fix all this for you – they might seem small but they really matter. But consider two things: 1. If I’m fixing your small mistakes, what’s my opinion of you. 2. Imagine how much joy I’ll feel as a people leader when I, repeatedly, notice your attention to detail (no matter how small the detail).

Also, it is not just little things about work. Caring touches all sorts of interactions you’ll have.

Here’s a great example: We had a little emergency at the office. While in my area, I rushed to get it fixed for a very senior leader. Two days later a thank you note arrived. It felt special. And, I know this leader is really busy, he did not have to write a note. I would not have noticed. But he did. He cared about little things. It spoke volumes about their values.

Another example: I had a meeting with someone on our team today. It was at 1500 hrs. She brought me lunch. She’d peeked at my schedule and had realized I would not have eaten. Little thing, big message.

4. Look beyond the near future, see the full landscape of opportunity.

Your world is smaller than your boss's. By design. You have a core area of focus. Your team peers will have theirs. That entire superset is your boss's world. It is much bigger, has a higher altitude, and contains additional strategic responsibilities (some obvious to you, others perhaps not).

An error occurs when an individual employee looks at their finite view and assumes that is all there is and proceeds to create solutions with that view. Or, identify problems with just that view. Or, unwisely, jump to conclusions based on that view.

You should always seek to look over the horizon, and expand your view.

Ask your boss to share with you how they see a particular situation. Ask your boss to more regularly share her/his strategic view of the landscape. Have a quarterly skip level with your boss's boss. Talk to the Director of an adjacent team and ask them questions about their goals, problems, objectives, solutions. Listen to your CEO's quarterly earnings calls. Make it a habit to not just see six or nine months out (be the person who can see three years out).

All this context will help you become a strategic thinker, you'll learn how to extract nuance, you'll be less upset with something short-term upsetting because you have the capacity to see the long view. Your boss will be appreciative, because your ideas will be strategic, more widely applicable, stronger.

This is an incredibly hard skill to learn. (And when it exists in a person, it makes them super-precious. If you have it, we are hiring!)

5. Create your personal board of directors.

Our bosses and immediate teams end up taking too much of our mind-share. It can be myopic, at times even suffocating. It impedes your growth.

Find four other people in the organization (not outside, though that can serve a different purpose) who you can talk to once every few months. You can bounce new ideas off them. You can ask them for unbiased advice. You can ask them how they tackled situation x or y. You can ask them where the snakes are and where the ladders are in the organization's bureaucracy.

Aim to have a diverse mix in your personal board. Perhaps someone at your level, and someone three levels higher. Someone in an entirely different part of your org. Someone in HR (if you are not in HR). Someone in Strategy. You can see how I’ve picked my board.

Have lunch with them (individually is best). Email them a simple question. Do a video chat if you are in the middle of a problem.

They are there to show you that your world is bigger than your boss's. (#1 reason people quit their team/company is a bad boss.) They are there to give you context. They are there to nudge your career in an optimal direction.

And, remember Dr. Cialdini’s first principle of influence: Reciprocity. Hence, don't forget to seek opportunities to give back to each person on your board.

6. Do at least one thing outside your immediate team/scope.

This is a lesson from Google's 20% philosophy. Spend some of your time at your employer working on an entirely different project/team. It can be related to your core job or adjacent to it or entirely different.

I work on Analytics in team x, I can work on an Analytics project in Verily, an Alphabet company, as I did the first six months of the CV-19 pandemic. I work in Marketing, I can take on a project in Sales or HR or Engineering.

A huge benefit is that it diversifies your view/job/thinking/culture/problem space/people you work with/joy sources. It is rejuvenating. A 20% project also exposes you to new company leaders (can't hurt, and maybe one of them will join your personal board). You might end up in a new job (!). Your company benefits because you are adding value in a new space, while accumulating new skills.

I'll warn you that my 20% projects at Google are tacked on top of my already long work hours. But, I'm happy to make the commitment because I derive such joy from them, and sincerely believe they are part of my personal growth.

In your current job, do you have a 20% project? 10%?

If not as a part of your current job, do you have a “20% project” outside of work? I cannot recommend enough the immense value of having a side hustle.

7. Invest in yourself.

Many of you are blessed that your company will invest in your growth. They'll make training available to you, they'll send you to a yoga+statistics retreat in Santa Cruz to make you an even better analyst, or they might even send you to a week-long course in presentation design at UCSD.

If your company offers these opportunities, proactively grab them. Create your own calendar with precise dates when you will do each of the above things (aligned with your career growth goals).

Chances are, your company is not going to care. Chances are, what they want you to learn is to get better at extracting coal just as the entire planet is abandoning coal.

In these cases, you are on your own. I still encourage you to take a leaned-in posture towards investing in yourself.

There are half-a-million free courses online in your job area, seek them out. There are people in your company who are the world's best at thing x, they will probably put something together for you to learn from. If your circumstances allow, there’s definitely a course at your local community college or local university that will cost you a bit but allow you to learn something new – you’ll have to pay some fees, but almost always you’ll make this back easily in the near-term if you apply what you learn.

The hard truth is, if you want to future-proof your career the responsibility for that is entirely in your hands. Only you care about you.

8. Ask for more responsibility, vs. asking for a promotion.

I love this topic. LOVE.

So much so that I wrote 1,241 words on this brilliantly critical concept in my Premium newsletter. You can read it for free here:

I do not say this lightly: You are going after your next promotion all wrong. And, your boss is not too happy about it.

9. Stay weird.

In corporate cultures, there is usually immense pressure to conform. This is not how we do things around here.

You would think that in order to be a good employee I’ll request you to be cognizant of cultural norms, adapt, blend in.

You would be wrong. I want to emphatically encourage you to be yourself.

Transparency: This is the thing I've struggled with the most, and remains deeply important to me (and I postulate it should to you as well for your long-term mental well-being).

I’ve covered this crucial topic in my newsletter, you can read it here:

As you navigate your long professional career, eliminate the possibility you’ll wake up one day and wonder who you are.

10. Solve for the company, not just your boss.

We, rightly, take directions from our boss and solve for them. Often, even when we realize that is the wrong decision for the company.

Actual conversation:

Heartbreakingly common.

If you find yourself in this position, ask your boss for more context as to why they are pushing for something that from your expertise seems wrong. Perhaps there is a valid business reason you don't know.

If none exists, on occasion, show courage. Stand up for the right decision for the company, bring your expertise and facts with you. It is unlikely to make you popular, but you'll sleep better and you'll be a good employee.

[My guidance to our team: Don't solve for me, don't solve for my boss, don't solve for my boss's boss, solve for Sundar. It gives us a clear True North, a global maxima driving decision-making aid.]

Pause.

That seems like a lot, no? Complex problems in life rarely have simple solutions (and if they do, they are almost always wrong).

The ten patterns on how to be a good employee above are not an exhaustive list. I wanted to write about the importance of developing a super sharp ability to say no, the value of learning that some fights are worth losing, and more. But, I hope ten are enough to spark new thinking in you.

Let me switch hats now…

How to be a Great Boss.

Being a great boss is much harder. Exponentially harder.

Here are lessons from my career, and from careers of bosses I’ve admired.

1. If you hire Michelangelo to paint the Sistine Chapel, don't hold his hand while he is painting.

We all start as individual contributors, and we are good at technical competence – that narrow collection of skills you need to be a coder, a cook, an accountant. Over time, you go from good to great (because you read my list above!).

Then, you get promoted and pretty soon the boss role requires general competence (being good at a lot of different things, particularly human-related). Hence, over a surprisingly short period of time, you’ll discover that if you are becoming a good boss that you are no longer exceptional at coding/cooking/accounting (areas in which you had technical competence). People in your team will surpass your technical skills (in fact if you are a good boss, you’ll hire people like that).

It is actually a good thing that you trade-off technical competence for leadership competence. You are becoming really good at leading a team, at strategic thinking, at slaying bureaucracy, at opening new thoughtscapes for the organization, and more.

Confreakingratulation!

With that inevitable switch from deep technical competence to general competence, a common, astounding, mistake bosses make is to apply technical criticism based on their general competence. They tell a coder how to write advanced code. They have no current analytical skills and tell the measurement team what their strategy should be. Etc.

Given the power dynamics, this boss makes their employee(s) work worse. They restrict, rather than expand.

Your job as a boss is to hire the very best that will come work for you. To create a culture of excellence. And, to bring hard problems to them. Then… Get out of the way and let your stars shine.

You've hired people who are better than you at the job they are doing. Then, for the sake of all that is holy, please let them do their job. Know your personal limitations.

2. Explain strategy. And, critically, why that strategy.

Most employees will have narrow roles which ends up giving them narrow views of the universe of possibilities. Often, it is hard for them to understand why the company decided on strategy x or y. Or even why suddenly View Time is the #1 KPI of the whole company.

You have a higher perch. You know all this (/much of this).

Your number one job is to set aside time on a continual basis to expose all this strategic thinking and decision-making to your team.

Go into as much detail as you can. Particularly help them understand the nuances at play, why it was so difficult to decide between A and B. If you can, use an example and share your thought processes to make the strategy/decisions better – there is rich learning there for your team members.

With this teach a human to fish gift, you've provided your employees with the invaluable context that will help them be more effective at their jobs. And, you've contributed to the body of knowledge that an employee will need one day to be a great leader.

Be super proud of yourself.

3. Your #1 job is your employee's career growth.

[See how many #1 jobs there are for a boss? Heavy is the head that…]

Honestly other than making sure you are the glue between long-term company strategy and short-term tactical execution, your only other job is to help your employees grow. Job title. HR level. Salary. Professional skills. % of mental satisfaction time.

Advocate for them in HR Rating dogfights. Did I say dogfights? I meant sessions.

You have a sense of their strengths and opportunities, convert that into your personal recommendations for internal and external classes they can take.

Support having a % of work time dedicated to learning. (20%!)

Create sessions where everyone can learn from each other.

(Ex: For my last team we had one full day every quarter in each office location dedicated to radical candor. We would put up our best work, and we would all have a go at it to figure out what we could have done better. It was brutal. It required an unbelievable trust in me (hard to critique your boss in public). These sessions fueled everyone's drive for excellence!)

On that note, sometimes as a boss you just have to have a tough conversation. Look, doing x is simply not going to cut it. I'm sorry but there is no path here that aligns with your long-term outcomes. Let me help you find a different one. This is going to be painful, but we need to talk about z. It is entirely possible the employee will not like it, but this is a part of truly caring (and a demonstration of your courage).

One tip for bosses when having tough conversations: Don't make it about you, make it about them. Seems obvious, I'm astounded how rare it is.

4. Teach how to think, not how to do.

The very best leaders teach how to think, how to expose nuance, the value of looking beyond the horizon, how to bring people along, the difference between a bug and a feature, and more.

Teaching people how to think will outlast your time in the team. Doing things for them, giving specific how instructions solve a short-term pain but leave little beneficial residue with the employee.

This is why, as a boss, I love frameworks so, so much! Care-Do-Impact for storytelling. Acquisition-Behavior-Outcomes for dashboard. See-Think-Do for Marketing. And more 2x2s than you can shake a stick at. All of these frameworks you've read on Occam's Razor came from my attempt at contributing to teaching the team how to think (or more precisely, how I think).

Frameworks codify thinking. Then, your employees don't need you!

That quite literally is the best thing you can do for yourself as a boss, because you are now ready to be promoted to a bigger challenge/team.

5. Set extraordinary standards, live them yourself first.

Both parts are important.

For any group of individuals to live up to their personal best potential, they have to have stretch goals. There has to be a component of normal is not enough. There has to be a spark that unlocks intrinsic motivation for excellence. Your job is to create a culture that's uncomfortably exciting.

Here's my current (overall) boss doing that:

"Lots of companies don’t succeed over time. What do they fundamentally do wrong? They usually miss the future. I try to focus on that: What is the future really going to be? And how do we create it? And how do we power our organization to really focus on that and really drive it at a high rate?"
-Larry Page.

Not wanting to miss the future is such a big part of why I wake up and come to work every day – uncomfortably excited.

You can't just create something you don't live.

Incredible employees rarely rise from teams led by lazy bosses.

If you are not personally learning or growing, they are unlikely to want to. If you are not showing attention to detail, they won't either. If you live a do as I say and not as I do… Well, if they do what you say it might only be under some punitive threat.

Walk the talk. You'll be exceptional.

6. Consciously invest in self-awareness.

Even the best leaders (self-included) over time lose their connection to reality.

We are high up the ladder, so full of caviar (is caviar vegetarian?) and frequently flying private jets (do they have premium economy?) that we end up with an odd view of ourselves. Sometimes it is imprecisely inflated. Sometimes it is entirely wrong. Sometimes you don't realize the true strengths you have as a leader.

I don't need to tell you how dangerous this is – the well-trodden path of every (ultimately) bad boss. The good news is that the fix is obvious, even if it takes conscious effort.

Ask for feedback, constantly. (And, create an environment where someone two levels below you in the HR ladder can be honest with you.)

If you can't ask for feedback, ask your employees (or personal board of directors) what can I work on next to be better? Leave it open-ended like that.

It is super effective: Shadow your employees for a day (or week), feel their pain, see their glory. Shadow a group in an entirely different part of your organization (I love call centers), try to do their job.

Consciously observe what other leaders do unconsciously that makes them so effective. Do the same for leaders who are disappointing, and reflect on what makes them so.

My friend Paul shared that he writes a few sentences in his journal each night – one thing that went really well that day and one thing that did not. Then, at the end of the month, he looks for patterns and it fuels his self-awareness. What a brilliant idea.

What do you do as a boss to invest in improving your self-awareness?

Pause.

The list for being a good boss is shorter because it is a list for being a great boss. It is harder.

It is not an exhaustive list. I wanted to write about 360° loyalty, building trust, truly understanding the difference between people and resources, and more. But, I hope six are enough to spark new thinking in you.

Bottom line.

Every human is a work in progress. I am good at some of the things above, great at a couple, and still struggling with some.

The important thing is to be aware of the patterns, create goals, and keep working on being better.

As always, it is your turn now.

What are two things, from either list, that you'll choose to focus on in order to be an even better employee/boss? What did I miss in either list that you consider essential?

Please share your feedback, and answers to the above questions, via the comments below. I look forward to the conversation.

Thank you.

PS: Something very special for you. John Fox of Venture Marketing generously created an infographic with the above reflections…

You can also download a pdf version if you would like a higher resolution for printing.