Starting Your Leadership Journey

I was reading Advice For Engineering Managers Who Want To Climb The Ladder written by Charity Majors (aka mipsytipsy). Her written style is a combination of bold, salty, and extremely intelligent – plus, she often writes about her own leadership journey. Worth adding to your RSS reader!

Anyway, I was reading that post and thinking, “hey, I like this idea” so I’m going to add to the conversation with my thoughts on adopting leadership patterns that serve you well across any sort of individual contributor or manager role.

Although, I’ve come to really dislike the term manager. It feels the same as calling a software developer a keyboard button pusher. There are projects and programs to manage, but people require leadership. So, I’ll just use the term “leader” moving forward.

I’ll do my best to avoid navel gazing. No promises. (Editor’s note: I failed)

Update: I was a guest on the Day 2 Cloud podcast (2022-08-10) to talk about this blog post.

Find your Why to start your leadership journey

Start with an anchoring exercise and find your passion. You need this.

It’s important as a leader to first find your why of things. John Ullmen, an Executive Coach and Professor at UCLA Anderson School of Management, often points to this as the authentic source of strength in times of stress or fear. In his courses on Executive Presence, he cites having a passionate why statement as one of the four pillars to driving true career success in a completely non-fake manner.

For me, the why is: Be an effective leader and mentor to my peers. It’s listed publicly as part of my 2022 Goals. My passion is seeing the best versions of people and seeking to connect them to others who can support them in their journey. I want to make a difference for the better. When I’m feeling challenged or threatened – and I may want to relent and given into pressure – I remember that my passion is having the discipline to maintain effectiveness as a leader and mentor. Even if the answer is no or I end up getting something wrong, so long as I held true to that, I know that my actions were aligned to my passion.

Simon Sinek is also a big fan of having a why. In the book Start With Why, Sinek writes:

It all starts with clarity. You have to know WHY you do WHAT you do. If people don’t buy WHAT you do, they buy WHY you do it, so it follows that if you don’t know WHY you do WHAT you do, how will anyone else?

Simon Sinek, Start With Why

I don’t have to guess at this. I know it because I’ve taken the time to self-assess, gather feedback, iterate with growth, and then self-assess again. It’s been a huge part of my year of Deep Work. To be a better version of myself through brutal honesty, data gathering, and trusted feedback loops.

Interestingly enough, in the past year I have changed from an ENTJ “Commander” to an ENFJ “Protagonist.”

When I read the Career Paths section, this jumped out.

It’s not a huge jump – from slightly Thinking to slightly Feeling – but it’s a noticeable change. I’ve started the habit of taking these sorts of assessments on an annual basis. Maybe this pattern will help you out, too.

DevOps your ideas with others

I was talking to one of my close advisers about my focus on organizational leadership as a part of stepping away from technology. He offered me a counter perspective. I wasn’t leaving technology at all, I was just embracing a different type of technology: that of building social structure. The same technology that fuels any collaborative social effort that is learned, iterated upon, and passed down to the next generation to use.

My hypothesis was this: since we’re dealing with a technology, successful technology patterns should hold true.

It’s been mostly right so far. Honestly, I just think of it as applying a “DevOps for Ideas” perspective. The faster you can gather ideas, test them out, and then implement and scale them, the faster the organization and culture can change and adapt.

Some thoughts:

  • Build ideas and seek the council of others to vet them. Ask for their ideas, too. Return the favor.
  • Create communities that matter to you, such as others in a similar or desired role or others of your seniority.
  • Use your concerns and learnings to invoke conversation.
  • Do everything you possibly can cross-functionally. 🌟 star for extra emphasis
  • Avoid silos like your life depends on it.
  • Test your ideas with small scale pilots.
  • Know what good looks like using data, especially from your trusted advisers.
  • Experiment with ideas frequently and maintain complete transparency that you’re doing it.

I’ve highlighted experiment for a reason.

Experiments are different from failures

Messaging matters. Here’s why I use the term experiment when communicating with people.

Experiment: a scientific procedure undertaken to make a discovery, test a hypothesis, or demonstrate a known fact.

People like experiments, usually. It sounds fun. What are we going to try this time? is a lot more enjoyable than We failed again, damnit!

Message to motivate. Use your experiments to try out ideas with your team and other cross-functional teams. See what works. Share it with others. Then, find other things that spark your passion and make them better, too.

As an example, I’m experimenting each day by offering my team a quick little challenge in our Slack channel. Most recently, I asked what they learned or are excited about learning. Half of the team shared something, so I tossed them a $10 gift card for the effort. The next day, I asked someone on the team to post a challenge. She chose to challenge everyone to share something they learned over the previous weekend, and bonus points of it’s project related. From that, I learned many things from the team, including the fact that an iPhone can play white noise (with a little video showing us how to do it). Groovy!

Know your goals and encourage goal setting

Leadership means being good at communicating what you’re trying to do to other people. I don’t mean that in an offhand “wow, yeah, Chris knows the words real good.” I mean the ability to listen so intently to someone that you stop really hearing the words themselves and instead hear the driving forces behind the words. The emotions. Their concerns and hopes. It’s all there, sort of floating behind the words.

Don’t let this go. These signals are saying hey, there’s an opportunity here!

Be prepared for this level of communication by knowing your goals and how you plan to achieve them. Treat this as your prioritized roadmap. Share it as publicly as possible, and refer to it when you hold conversations about your career, what you want to learn, and strategic partnerships you wish to form. People trust honesty, and nothing is more honest than showing your cards.

Getting back to the person with concerns. Align to them! How can you connect that person to the right information, person, or place? In short: how can you add them to your network and community?

I bet that feels weird to think about. But, the sooner you start to see other people for their passions and goals, and start thinking about how you can align to them and work together, the quicker you will unlock value that is difficult for others to replicate.

Consider aligning your goals to that of your leaders, but don’t forget to consider what it is you want to do. In most cases, I find that you can do both. Smart leaders will see you making plans, writing down goals, and coming up with ideas, and they are going to want to ally as a partner. That’s when the magic happens! Team up and go make things happen, and invite more people to support along the way.

The fun part is in leading a team and building them into the next round of leaders.

Contribute to a culture of leader-building

I recently finished a book titled Turn the Ship Around!: A True Story of Turning Followers into Leaders by L. David Marquet.

It is fantastic. It is all about creating leaders and building a culture of leader-to-leader relationships. If I took one thing from this book, it is that being able to create a truly distributed decision making organization unlocks some wicked amazing results.

As I see it, job one for everyone at an organization is to build leaders through coaching and developing others. It sends a message to your boss, your peers, and your direct reports that we’re in this together. They have their jobs, and you have your job, and it’s really all about expressing priorities and aligning to goals via healthy channels of communication.

Be the example from which you wish others to pattern. Don’t wait to be told to lead.

Some final tidbits for aspiring new leaders

Being a leader doesn’t mean being the boss or a manager. It is something that we can all do. And, in fact, when we take it upon ourselves to be leaders, the world often rewards us with work that is higher value, more interesting, and greatly financially compensated.

Here are some tidbits for you to experiment with:

  • Own your 1×1 time. Drive the agenda, focus on your career path, and leave mundane updates to async channels (e.g. Slack). Treat your boss as the support structure for your time, not the other way around.
  • Update and communicate goals. Keep your goals public. Revisit them weekly or monthly. Gather the team up once a month to share status on goals, discuss concerns over timeline, and socialize ideas on how to improve.
  • Run retrospectives to frequently gauge feedback. Use tools such as keep-stop-learn-action or a SWOT. Getting buy-in, perspective, and feedback from a diverse audience should be a normal part of operations.
  • 🌟 Seek council from others 🌟. Identify your peers and those who have roles you want and be clear that you want to learn how they think and make decisions. Heck, find those who have absolutely nothing to do with your department and start a dialog. Find common ground, build communities, shrink the amount of silos. Use your network to share your concerns and goals, and seek support.
  • Treat your career and performance as an unending project. Document everything you can about who you are today and who you want to be tomorrow. Be extreme in your investment here. It’s never “one and done” as much as it is “recognize, then strategize.”
  • Take absolute control and responsibility over your career and life.

I work in a leader-leader environment. It’s the best, hands down. I would never, ever want to be a leader in any other way, and I absolutely love having talented team of smart individuals that challenge my perspectives and make me better.

I recognize my role as a leader is being a supportive passenger in my team’s career journey while recognizing and encouraging them to be the one driving. Remember, message to motivate.

The sooner we all realize this, the happier we’re all going to be.

OK, rambling over!

Peace and love. ✌