Finding your leadership style

When it comes to career advice, a common recommendation is you’ll need to work on your leadership to become more senior.

In previous times “leadership skills” may have been code for “become a manager”, but nowadays even in hands-on/individual contributor roles leadership skills are becoming increasingly sought after. People are encouraged to know their leadership style, name and share it with others, as well as understand how to flex in different situations.

But I know from experience that this can be easier said than done for lots of folks. Some people just don’t see themselves as leaders in the traditional sense they’ve been exposed to to date, and even if they want to grow in this area they can find it hard to turn abstract concepts of “leading” into something practical that they can grow towards. Sometimes this happens before you’re in a typical leadership position, but there are also a lot of people out there who’re already doing a leadership role whilst still trying to figure this stuff out!

How on earth do you start to work out what your leadership style is, or could be? What skills do you need? What do you need to do to live it? In this post I’ll run through a whistlestop tour of the concept of leadership, and share some of the prompts that I’ve used to help people navigate this tricky topic. As always my wording and examples are slanted more towards engineering and technology, but you should be able to apply the concepts to other domains too.

Defining leadership is complex!

Before we dive in, it’s important to note that there is no one definition of leadership. Wikipedia’s Leadership page notes that it’s a contested term, with specific global geographical differences in approach noted, as well as changing perspectives over time. However, despite this, the essence seems to be that leadership relates to the ability of a person or group to guide others in pursuit of a purpose or outcome.

Whenever I come up against quite abstract terms, I like to head over and do an image search to see how stock imagery interprets it. If you do so, you’ll likely see lots of cliched imagery of swashbuckling generals, leading from the front, standing alone, and most likely being very masculine. There also seems to be a bit of a thing about superheroes and capes. Many of the images you’ll see have coded aspects of racism, sexism, ableism, and other isms.

Don’t be too disheartened! Whilst this is definitely one take on leadership, as the Wikipedia page details, there are plenty of other ways and styles to embrace leadership, both in what you do, and how you do it.

At this point it’s probably worth doing a little bit of reading about different approaches to leadership in your field. Some of my go-to references to point people towards include:

• Pat Kua’s Flavours of Technical Leadership talk
• Lara Hogan’s Leadership Style Colours
• Will Larson’s Staff Engineer Archetypes
• Leadership on a Submarine and the related book

However, there’s again a lot of focus here on more senior positions. When I sat down and thought about examples from working with people at all stages in their careers day-to-day, I came up with examples like people:

• Taking charge of creating a restructured “engineering wiki” for docs, gathering input, and sharing it back.
• Helping a less experienced engineer to better understand database migrations and scripts.
• That person then subsequently giving a talk and sharing their new knowledge with even more people.
• Taking ownership and making decisions on team socials and rituals.
• Suggesting improvements to interview scorecards without being asked.
• Introducing estimation sessions to their team.
• Advocating for quality, and investing in paying down debt.
• Creating a survey that helps surface areas that people want to improve.
• Introducing new technologies to the business.

As a junior engineer, leadership may feel lofty, but demonstrating it can be as simple as fixing errors in documentation or re-wording it to be more effective for others. This is still leading others to a better outcome.

📝 Prompt 1: how do you feel about leadership?

Interaction time! With these prompts, I’ll aim to help you walk through your own approach to leadership. If you’re struggling with this, consider getting someone to coach you through it (a manager, trusted colleague, friend etc). You don’t necessarily have to answer all of the questions, you can just talk through the ones that you think are most useful, or which spark the most thoughts. Let’s start at the beginning. Having read the above…

• What does leadership mean to you?
• Do you already see yourself as a leader?
• Do you want to be a leader? Why, or why not?
• Are there expectations from others for you to be a leader? What kind?
• What kind of different styles of leadership can you think of?
• How do your feelings match up to how others describe leadership in business books and articles you may find?
• What’s beginning to resonate the most?

Understanding leadership styles can unlock opportunities, and remove barriers and friction

Personally, my views on leadership have changed a lot over time. I’ve become much more confident in my own style, and have started to advocate a lot more for an understanding and appreciation of people leading in their own way. This has tied a lot into my learning about progression frameworks, and how we can codify and reinforce expectations… for good and for bad!

As things stand, I’m really clear that as a default I…

• Don’t enjoy being ‘just a cog’; I actively like working on making a difference.
• Want to have the autonomy to create systems that set people up for success, and work on bigger picture change as well as more self-contained improvements.
• Care about diverse, empathetic, safe spaces where people can do great work they’re proud of, can grow as people, and which will eventually take them on to greater things.
• Need to keep learning, like being stretched, and want to make it safe for me and others to do so (and make mistakes along the way).
• Care a lot about making tech a better place, and thinking about tech ethics and misuse.
• Lead from the back, not the front. I do best when I enable others, consult, and steer rather than pulling everyone along.

We’ll come back to this later but it’s important to note that sometimes you need to flex your style in different situations. However having a good sense of your own default style and how that meshes with the environment around you can smooth your everyday interactions. I can flex my leadership style – for example if there’s an emergency and I need to urgently direct rather than consult – but if I was working in a situation where the above wouldn’t apply for the majority, I know it’s probably not the best match for me.

On the good days, finding a leadership style that suits you and your environment will mean you can operate most easily, keep your energy, be resilient, and authentic. You’ll feel like it’s easier to bring out the best in others. However, if you use a leadership style that’s ineffective or just doesn’t fit your strengths you’re likely to have a harder time, or even find you’re failing more than you’re succeeding.

When I think about some of the points in my leadership career I’m least proud of and have most regrets over, they’re almost exclusively times where I felt like expectations of my leadership were mismatched with what I felt was appropriate or authentic. At times I’ve felt like I sacrificed some of my integrity, because I wasn’t confident enough in the situation to advocate more strongly for a different approach. This can lead to friction for you, and worse outcomes for the people you’re leading.

📝 Prompt 2: what approaches or elements of leadership feel most natural for you?

Start to think about how all of this applies to you, whether that’s times where you’ve been successful and helped to lead others to a good outcome, times where you’ve struggled and been frustrated, or think about people you’ve worked with who you’ve seen as great leaders and would like to emulate.

• Speak to other leaders – how do they see themselves? How did they develop their sense of leadership? What can you take from that?
• How would others describe your leadership? What would they recommend you lean into?
• What are your strengths? How can you turn that into how you lead? For example, if you’re great at persuasive speech, maybe you can lead by lending your voice to helping someone make a case for technology changes.
• Can you think of a time when you felt most like a leader? What was happening, what were you doing?
• What do you care most about, and feel passionately about? If you were going to start a company what kind of place would it be?
• Who are you leading? Who are you trying to connect with? What matters to them? 
• What kind of technical skills, hard skills, subject matter expertise do you bring?
• What are you acting like when you feel most empowered and rewarded?
• What do your life experiences and personal identity contribute to your self of leadership?
• What do you want for others? Think about careers, workplace environment, culture to operate in etc.
• What challenges do you need to overcome to lead authentically? This could be other people’s limited view of what a leader looks and sounds like.
• Who do you admire for their leadership, and what qualities do they have?

This last question in particular is one that I find myself constantly coming back to and challenging myself with, to help me continue to evolve my leadership. Some real examples of people who have inspired me to grow:

• Someone who’s amazing under high pressure and with uncertainty, who always keeps everyone calm, can make decisions effectively, and provides enough realism balanced with optimism.
• A storytelling genius, great at strategies and getting everyone genuinely excited about the role they can play.
• A person who leads by example without being showy or gatekeepy. They can easily move between being highly technical, but also showing vulnerability, honesty and helping everyone feel like they can belong.
• Someone great at coaching others, sharing skills, being the best example and always working so it trickles down through others.

📝 Prompt 3: pulling it all together

By this point you should hopefully have a whole ton of notes and thoughts! How you pull it together is up to you, but some approaches that can work well are to make a mind map, write out recurring points on individual cards, or just get a blank sheet of (virtual or real) paper and start adding words.

To bring it all together, I’d encourage you to think about any themes can you see around how you’ve been describing:

• The values you already/would like to embody as a leader
• The strengths and experiences that you’ll bring to back this up
• The activities and behaviours you use, or would like to use to lead
• The environments and scenarios that you thrive in, and the kind of people you want to work with
• The kind of outcomes that you strive for

If you’d find it useful, you can try to turn this into a little bio-esque paragraph about you as a leader, to help cement and communicate some of the ideas. Or if you struggle with this kind of self-description, give your notes to someone else to pull together for you.

📝 Prompt 4: take it for a test drive

Congratulations, at this point you’ve hopefully figured out a plan to get comfortable with your default approach to leadership, and the style, approach, and situations that you feel you can be most successful in.

Now that you’ve got a bit more of an idea around what leadership may mean for you, it’s time to try it out. A safe way to do this is to pose yourself some hypothetical challenges. You can come up with your own, but as a starter, how would you approach the following with the leadership style you’ve been thinking about?

• You’ve just found out your company strategy is changing, and because of this your team’s being disbanded. You need to break the news.
• Advocating for an engineer that you feel is being unfairly treated by the business.
• Trying to improve retention of people at your company.
• Replacing a fundamental piece of your tech stack with something totally different.
• Trying to advocate for a major piece of technical improvement work that won’t have any visible difference for the product or customer experience.
• Your CTO is making what you think is a really bad mistake.
• Helping to improve morale within your team.

For each of the scenarios you think about it can be useful to consider what feels natural and easy, and what still feels uncomfortable or like it would be a struggle. This can help you better understand where your style works, where it starts to fall down. What can you learn from this?

📝 Prompt 5: evolving and adapting

Don’t be too disheartened if your natural style doesn’t fit every situation – this is normal and to be expected! In addition, even though you’ve identified your current style, you may find you keep evolving it over time.

I’ll leave you with some final nudges to think about:

• What are the gaps between where you’d like to get to and where you’re at now? Which bits are you still working on, or don’t feel fully comfortable with yet, and how can you find opportunities to practice?
• Who can you learn from, and how can you experience even more leadership styles and situations?
• Based on some of the gaps you’ve found from above, or situations you’ve found yourself in, how might you need to change up your style at different points? What might you need to work on this, particularly if the situations call for something that doesn’t come naturally to you? (You may want to think about training, opportunities, habits to form, or other support to ask for)

(Header photo by Jamie Templeton on Unsplash. Thanks, Jamie!)