Career lessons learned: how small tweaks can make all the difference

A collection of career lessons I've learned that have lead to greater professional fulfillment, better workplace partnerships, and accelerated career growth.

Beware, there be dragons

Careers are tough. With everything from workplace bias to gender pay gaps to simply trying to find what you’re passionate about, the modern professional encounters a number of obstacles. And then there’s people: namely our co-workers. Often the greatest challenge we face is not the work, but the people we work with. There’s also professional growth. For those of us who are fortunate enough, we encounter opportunities for growth: perhaps, we get the promotion; or perhaps, we get accepted to our dream job; or perhaps, we get the opportunity to lead and manage a team. But then these opportunities turn out to be far more challenging than we anticipated. The excitement dwindles and the inevitable anxiety settles in: were we really ever equipped to take on this job? will others support us when we need them to? will we buckle under pressure, or can we arise to meet the new challenge?

The lone warrior?

If you’ve ever felt these emotions or had these doubts, you’re not alone. In fact, from my experience everyone at some point or another has felt and continues to encounters these circumstances (dragons) throughout their career.

In this article I’ll cover a few of the lessons I’ve learned throughout my career, and speak to their practical importance. I’m sure many of these findings will be familiar to you. My hope is that some of these resonate with you, but also lead to new insights and tools for how to meet this situations with confidence in your own professional journey.

Let’s begin, shall we?

Perception is reality

In an ideal world, people want to believe they are rational actors. Walking around like detective Colombo, asking for “Just the Facts.” Making decisions and formulating opinions based off of the proof. However, by and large, what I’ve experienced throughout my career is that people actually lean heavily into their own perception: acting more like Sherlock Holmes than Colombo. They consider the information they “see” or “don’t see” and make their own deductions (or assumptions) from there.

People consider the information they “see” or “don’t see” and make their own deductions (or assumptions) from there.

As an example, I’m very passionate about pursuing the truth. I index on this. But what this means, is that my truth seeking questions and comments in strategy meetings, have sometimes been seen as “divisive” or “irritating.” And let me be clear, I can see why. No one likes a naysayer. The problem is that my intention and others’ perception are misaligned. I intend to get to the truth of the matter, but I sometimes forget that a little sugar makes the medicine go down.

I have several other flaws, but for the sake of brevity, let’s stick to this one. Early on in my career, this behavior of mine often led others to view me as “hard to work with.” It created a dynamic in my working relationships that was unhealthy. And people, had a difficult time seeing the value of my proposals because of the way they were presented.

So I changed. And I keep changing.

Understanding that perception is reality, is key to driving the narrative you want about yourself.

One of my favorite quotes that has really helped me in this area is by Voltaire, who says, “ It’s not enough to conquer people; you must seduce them as well.” I had the truth, but I lacked the charm. Understanding that perception is reality, is key to driving the narrative you want about yourself. It will help you with establishing healthy working relationships and productive partnerships with your teammates. It may even help you to establish a little empathy for yourself and others.

Build trust

I hope by now most companies are realizing that trust is the most essential quality to employee productivity and organizational health. I’ve seen and participated in several organizations that had highly intelligent, highly skilled, highly capable people, but they were incapable of working together or producing repeated customer value. What I realized is that external products mirror the internal organizations that build them. Chaos or misalignment bleeds through to the edge.

Awhile back I read a leadership book by John Maxwell called 21 Irrefutable Laws of Leadership. I understand that leadership books by white men are overplayed, but this book really resonated with me. In particular, Maxwell calls out the “3C’s” of leadership that are essential for building trust:

  • Character
  • Competence
  • Connection

Healthy organizations, wether they know it or not, exhibit these 3 characteristics, especially in leadership. And vice verca for unhealthy organizations. Roughly here’s how I interpret these areas:

  • Character: do your actions match your words? do you prioritize the right thing, over the easy thing?
  • Competence: are you effective in your role? Do you frequently deliver impactful work or make strategic, beneficial decisions?
  • Connection: do you care about others and show it? do you understand their goals and aspirations?

While everyone contributes to a culture of trust, managers and leadership should be held most accountable, because their behavior and decisions have broad impact. As such, it’s crucial that leaders regularly evaluate themselves in these areas as well as provide broader organizational opportunities for feedback in them.

Bait the hook to suit the fish

When LLoyd George, British Prime Minister during WW1, was asked how he managed to stay in power after war time, he responded that he learned to “bait the hook to suit the fish.” That is, he dedicated time to understanding what others wanted. And, then he framed his proposals in a way that appealed to their desires. This seems like such a simple thing, but it’s deceptively difficult.

Throughout my career, I have often started conversations from the perspective of “what I wanted,” or “what my discipline needed.” I was inwardly focused. Needless to say, it didn’t get me very far — even if I had solid reasoning. And here’s why. This may sound harsh, but most people are rarely “philanthropic” towards their coworkers. We each have a tendency to focus on our own area of expertise, our own domain of concerns, and hence our own desires and wants. So, if you want to create change in your organization, if you want to drive a new direction that requires help, if you want to have influence, it’s extremely beneficial to ask “what’s in it for the other person?”

If you want to create change in your organization, if you want to drive a new direction that requires help, if you want to have influence, it’s extremely beneficial to ask “what’s in it for the other person?”

Some other helpful questions might include:

  • What are their goals?
  • What makes them feel important?
  • What motivates them to act?
  • How could your proposal benefit them?

This may sound a bit manipulative, like you’re being disingenuous. But, I believe it’s actually an opportunity to create greater productivity, empower others to do their best work, and facilitate a solution that is mutually beneficial for both of you in the long run. So, get your tackle box ready, because every fish has a different appetite.

Set expectations, early and often

Expectation setting is essential to productive working relationships and to your own mental health. It ensures that you and the people you work with are on the same page and aligned on key aspects of your job. I recommend having expectation conversations any time you start a new job. And then keep having them every few months.

There’s a few layers of people you might want to have these with. I’ll begin with the position of an IC (individual contributor). Start with setting expectations with your manager. I’d recommend asking them what they expect from you to begin with. Then provide your own thoughts. A few helpful questions could include:

  • What do you expect from me in my current role?
  • What kind of and how much visibility would you like on the work I do?
  • How do you feel I can best support the mission and values of this team?

However, expectation setting should be a two way street. I think it’s incredibly valuable for IC’s to help their managers understand how to work with them, what kind of triggers they may have, and what kind of help they need. This could include areas like:

  • How you like to receive feedback
  • What kind of behaviors are triggering for you
  • Where you feel like your strengths and weaknesses are
  • What makes you tick or come alive
  • What your long term professional aspirations are

Expectation setting should be a two way street

Another layer of expectation setting is with your partner teams. With partner teams it’s important to identify areas of ownership, as well as the particular responsibilities of each discipline. Some helpful topics and questions for partner expectation setting may be:

  • What do you feel you are responsible for driving and owning?
  • How do you currently work with my discipline? What, if anything, would you change about the current workflow?
  • What do you need from me and my team to do your job effectively?

Now, I’ll shift over to managers. As a manager, the most productive and impactful thing you can do with your team is driving alignment. Some helpful areas to cover with each team member might include:

  • What success looks like for the team
  • What kind of results you expect from them
  • How you will evaluate their performance
  • Ways they can leverage you for help
  • Opportunities for career growth

It’s important to realize that these conversations are not a “one and done deal.” Inevitably things drift over time and people can get out of tune. I have been playing guitar for over 15 years now, and one of the things I realized early on is that when you play with other musicians, everyone regularly has to “retune” or “recalibrate” to a central tuner. It ensures that instruments can harmonize with each other. Working on a team is very similar. What worked 6 months ago, may not be the thing that works now. And so, you have to regularly recalibrate.

Some helpful exercises that managers can conduct with their teams to recalibrate is the “start,” “stop,” “continue” exercise. This type of exercise can be done with whiteboards and sticky notes or with tools like Parabol. The basic idea is for everyone to provide thoughts on:

  • Things they should start doing
  • Things they should stop doing
  • Things they should continue doing

It’s an opportunity to adopt good behaviors, discard bad ones, and emphasize existing ones. This exercise could be conducted at any time, but I find it’s helpful after a larger shipping cycle, because the team has had time to observe and take note of a range of processes and behaviors

Be Visible

I, self-admittedly, can be a bit of a hermit. I have a tendency to find the job that needs to be done and then do it. I involve the parties that I need to partner with and then move forward. What this means though, is that I don’t always volunteer information.

Let’s go back to the first point “Perception is Reality.” When people don’t know about the work you’re doing, then they start to draw their own conclusions. You may do awesome, innovative work, but if people don’t know about it, then there’s a drop off point for them. I’ve found this to be a point of contention with managers I’ve had throughout my career. I didn’t regularly give detail and insight into my work (often because I was busy doing it), and some managers interpreted that as me being disconnected or unavailable. One of my friends calls this the “leaky respect bucket.” Over time, people may forget your contribution or the value you offer, and respect leaks out the bottom of their metaphorical bucket. And, it’s important to realize that some buckets drain faster than others.

Over time, people may forget your contribution or the value you offer, and respect leaks out the bottom of their metaphorical bucket.

I finally came to understand that people will only appraise what they observe.

So, something I’ve started doing recently with my managers is offering visibility into my work, via links, slack, meetings, and status updates. In our 1:1’s, I’ll calibrate with questions like:

  • Is this enough visibility into my work and processes? would you like more? or less?
  • What would you like to know more about?
  • What kind of questions do you have about current work in flight?
  • How do you think I could improve on “scenario A”?

These 1:1’s are also an opportunity to explain the complexity or ambiguity of your current projects and seek the help you need from your manager.

This may feel awkward at first, like you’re bragging or showing off or asking for too much help or honestly offering unnecessary information. But it’s not. It’s giving people the information they need to understand your contribution and generating an opportunity for valuable feedback.

Hold yourself and others accountable

We spend a lot of time with the people we work with. Throughout our tenure, we are given so many opportunities to grow and help others grow. We are given insight into the goals of those around us and, and as leaders, an opportunity to help our reports achieve those goals. Additionally we see what others struggle with and where they may need help. Overall, one’s career is a significant responsibility with wondrous dividends when we truly invest in ourselves and those around us.

But, it’s easy to miss these opportunities. We get busy, or we forget, or we get distracted. We substitute good intentions or flowery words for real change. That’s why we must be accountable: to ourselves and to others. Being accountable means that you have skin in the game. It means you lead by example. It means you have a bias towards action. It means you own up to your mistakes and strive to do better.

Practically, here are a few tactics I’ve found beneficial for accountability:

  • Never leave a meeting without next steps
  • Use follow up meetings to discuss how these next steps are going
  • When feedback is given, create an action plan with specific tactics and communicate that back to the people who gave the feedback
  • Measure your progress with others

At its core, accountability is asking, “what needs to change, and what are we going to do to get there?” And then, continuing to evaluate the progress made over time.

Have a growth mindset

Through my career, I have met gatekeepers and bridge builders. I have also been both. Gatekeepers rely on existing knowledge and comforts and refuse to give ground, even in light of new evidence. Alternatively, bridge builders seek connections between ideas and people. Their journey is not fixed; it’s on going. And new evidence, is not a burden; it’s an opportunity.

Bridge builders seek connections between ideas and people. Their journey is not fixed; it’s on going. And new evidence, is not a burden; it’s an opportunity.

Change is difficult, we all know that. It challenges our status quo, and maybe even our sense of self worth or intelligence. But the cost of not changing, is higher than the cost of changing. While at Microsoft, I came to really embrace Satya Nadella’s introduction of the “fixed” vs “growth” mindset. Gatekeepers have a “fixed” mindset: they are intimidated by new challenges and changes in information.

Some ways to tell if you’re having a “fixed” or “growth” mindset are:

  • How do I deal with new developments or evidence of information? Do I meet it with frustration and judgement? Or, do I meet it with consideration and openness?
  • When confronted with a personality flaw, do I hide it or acknowledge and improve?
  • How do I view alternative perspectives and disciplines?
  • When I receive feedback, do I seek to understand or do I deny it?

To borrow another Satya phrase, I strive to be a learn it all instead of a know it all.

Avoid thrashing

The modern work place buzzes with a constant influx of information: slack feeds, emails, meetings, task trackers, twitter feeds, new articles, and so much more. It’s a wonder we get any work done; or do we?

Computers are amazing task managers. They can switch between tasks ( apps ) with the click of a button. But they also store all of these things in memory. And, there’s only so much memory. Some memory gets spent on “responding” to your requests, while other memory is spent producing an output ( actually performing tasks ).

In computer technology, there’s a term known as “thrashing.” Essentially a computers starts thrashing, when all of its memory is being used for “responding,” and there’s no memory left for producing an output.

Sound familiar?

Remember that constant stream of information and things you need to respond to? If you’re anything like me, I’m sure you have had days where you ask, “now what did I accomplish today?” and hear silence on the other end. Response is necessary and useful, but it’s best if you designate certain times for it or delegate if you have that luxury.

Context switching comes at a cost, and productivity happens when you designate time for deep work and time for responding

Some helpful approaches for balancing response time with focus time are:

  • Leveraging something like the Pomodoro technique to create 25 min deep focus time slots.
  • If you’re big on email, using a certain time of day (I typically like afternoons) to respond to all pertinent emails.
  • If you’re big on Slack or other chat apps, try designating 5 minutes every hour to respond to all requests.

Really the technique can vary. The key thing to remember is that context switching comes at a cost, and productivity happens when you designate time for deep work and time for responding.

Regularly evaluate your professional goals and your company’s direction

I left this lesson for the end of the article because it’s something that I have often failed to evaluate regularly. I have a tendency to be fully planted in the here and now. Projecting my long term expectations about life is difficult for me. But, I’ve come to realize that a failure to frequently evaluate my own professional goals means I can spend time walking down a path that wasn’t meant for me, or that I should have left long ago.

Professional goals encompass so much of what we want out of life. After all, we spend the majority of our lives working. Work can lead to a great amount of pleasure, or alternatively it can lead to growing resentment and disappointment. And usually these two outcomes are linked closely to the intersection, or lack there of, of your professional goals and your company’s direction.

I’d like to give a few pointers on how to evaluate your professional goals and your company’s direction. We’ll start with the first one. The following questions can be helpful when understanding your professional aspirations:

  • First, what makes you tick? What makes you come alive?
  • Equally as important, what is completely drudgerous and mind-numbing for you?
  • Are you farmer or hunter? Do you prefer nurturing existing product areas and operating with clear constraints? Or, do you love big ideas with limitless possibilities?
  • What areas of your profession would you like to grow in? Leadership? Management? Particular skills or expertise? Cross-Disciplinary communication?
  • What type of influence do you want to exert in your organization or your industry? Do you want to be known as a great presenter? An effective strategist? A people connector? A knowledgeable domain expert? A caring mentor? An educator? An innovator?
  • What makes you feel important?
  • What does success look like to you? Is it pushing the limits of quality and innovation? Is it creating organizational momentum? Is it having others look to you for advice or perspectives? Is it customer testimonials that validate your work?

One thing you will notice is that these questions are centered around who you are and what you care about, not what you produce. We have to know what we care about before we can know what we want to invest in.

We have to know what we care about before we can know what we want to invest in.

Regarding ways to evaluate your company’s direction, some questions might be:

  • Who are your company’s customers and users, and how is it trying to help them?
  • What values does your company talk about it? Now, how does that align with their behavior?
  • Does your company or organization prioritize growth (acquisition of new users and new market places) or profit?
  • What are the priorities of your leadership team? (VP’s and C-Levels)
  • What’s your company’s roadmap?
  • How does your company grow and invest in existing talent?

Money talks. And you can learn a lot about what a company prioritizes by following the money.

Charting your own course

As you continue your career and go about your day, I hope that the aforementioned lessons resonate with you on some level and can help provide clarity. I’ve done the easy part of identifying the lessons, but the hard work now lies in figuring out their application (even for me). As always, if you have thoughts, feedback, or personal stories of your own please hit me up on twitter. Thanks for reading!