Coaching w/ Challenges

One of the criticisms I hear often when coaching engineering leaders is that no one provides enough guidance on the steps to becoming a great leader.

I think most of you who have joined me in that type of coaching position understand my methodology. These “steps” are one of the greatest fallacies in professional development.

So, my style of coaching is very much adapting each leader to finding their own unique leadership style that suites their personality and experiences.

Having said that, I do find some commonality across every new leader, regardless of the style they employ, and I do believe it’s worth delving into. There is a lot of criticism and meme-worthy commentary on our industry on how we build our engineering leaders through trial by fire.

The dichotomy of growing leaders looking to find the set of instructions to succeed in their new positions, and the experienced leaders who understand that these instructions don’t exist, makes a person wonder how our industry even survives at all? Let alone thrives? Is it completely out of necessity to support the burgeoning knowledge-based infrastructure? Will we someday face a generational crisis as a new generation of leaders understands the mechanisms of technology but not the people creating the technology?

I do not think we are on the verge of such a crisis, but it is certainly a fair criticism that particularly in the engineering space, those of us that have had leadership training and experience can perhaps do more to share this wisdom with our industry peers. While it remains true that “steps” to being a great leader do not exist, I can at least outline three of my very loose guiding principles I follow in building new leaders:

1. Be Antagonistic

Young leaders need it. We’ve all experienced the first-time leader who thinks he’s naturally gifted, and everyone will meet his expectations immediately.

I’m not worried about antagonizing that leader…the real world will antagonize that lot soon enough.

I’m thinking of the more nuanced leaders. The ones who do “get it” straight out of the gate. They usually have a modicum of soft skills. They’ve been identified as a leader by their peers in a natural fashion. And usually, HR is in the corner badgering you to promote them quickly.

The problem with not antagonizing these leaders is they tend to be afraid to stray outside of their comfort zones. Leaders need to be adaptable. Different situations call for different leadership styles.

Is a project wildly behind schedule and overbudget with employees not showing up for work? The big bad word “Direct” leadership…might be a needed tool. Is your soft skilled leader up to that challenge?

Can they be a coaching leader when training is needed?

Can they delegate when too many tasks are thrown at them?

It’s shocking how many young leader’s careers are completely derailed because their senior leaders did not antagonize them enough. Any one of these scenarios could be an initial point of detriment to a young leader’s career, that can snowball into an insurmountable barrier when shifting into higher level leadership positions where these skills are expected to already be refined.

I’ve had the unfortunate experience many times now of watching Directors and Senior Directors lose their positions for being unable to take charge, unable to delegate, unable to do the things that are outside of their natural leadership style. They weren’t antagonized enough as young leaders.

The word antagonize is by choice, and sometimes rightfully criticized. I stick with it because, it is a naturally antagonistic conversation. If you’ve ever engaged a young leader and tried to work with them outside of their natural leadership style, you will understand what I am talking about.

Even coaching through it — they will squirm and gripe and do everything in their power to revert to their natural style that suits their personality. It is by nature, an antagonistic process to exercise other unnatural leadership styles.

So, I will definitely be making my soft skilled leaders engage in some very hard, direct conversations at every opportunity, and vice versa. We build strength by exercising the muscles that are the weakest. There are some great soft skilled leaders whose direct-style leadership is the “leg day” of their repertoire. They need to work those muscles out to build a strong foundation.

2. Listen, and Guide. Do not advise.

Too many young leaders have come to me asking for instructions on how to handle a given scenario.

I have answered that question for them exactly zero times.

Consider this. A direct line leader is responsible for building and establishing a relationship with their direct reports. That rapport is the backbone of any organization. With that in mind — by what logic does it make sense to interject my temporary personality quirks into that relationship?

Because that’s what me answering the question for the younger leader does.

That leader is now operating from the perspective of “this is what my boss” would do — and I’ll be frank — I always operate from the perspective that I’m attempting to build leaders far, far, FAR better than me.

I don’t want them to think about how I would address a problem. I want them to think about how much better at the job they are then me and come up with a creative solution that reinforces and builds the relationship they have with their direct report.

That’s not to say I don’t encourage them to come to me with problems. Like any good leader I hold consistent 1:1s and absolutely interrogate my managers for how their teams are doing. A lot of times this interrogation is over a beer or a solid round of Mario Kart (Nintendo Switch made this so much easier) — but rest assured while I’m slacking off, I’m also very intently listening to your ongoing struggles as a young manager and helping you uncover your sense of creativity in leadership, all at the same time hitting you with the blue shell and riding across the finish line.

Again…listen…and guide. Discussing problems are great. Solving them for your leaders, not so much.

3. Understand the Personal Aspect of the Leadership Journey

This one may be particular to me, but it took some time to realize kindness and directness are not antonyms.

As a person with autism going through the leadership journey, I realized early on, that I’m not going to be that soft skilled, super conversational coach that I always wanted to be.

Now, there was a decision point in my career where I could have chosen to go full neckbeard and abandon the notion of leading. I could have leaned into my autistic tendencies. There are plenty of very successful, remarkable, well-paid autistic software architects who operate in secret at the upper echelons of every Fortune 500 in America and I’m sure I would have joined their ranks quickly and led a much less stressful life.

Few realize that for me — showering, shaving, and jumping in front of a zoom camera — that’s like running a daily marathon! It takes ALL THE ENERGY just to smile on camera until I sign off for the evening.

It’s also a weird conundrum for me because I do love people. I sincerely do. I just need to lay in a dark room for two hours after talking to them.

But I do care about them so much! It’s very weird to me!

So, I made a choice way back in those early adult days that I was not going to let myself off the hook that easy. I was determined for many personal reasons (violent home, poverty stricken, poor education), to become a good leader and grow the skills I was weak in, while maintaining my technical skills as a backup option in case I wasn’t able to cut it.

It’s 25 years later, with many years of emotional intelligence courses, military training, and executive leadership courses, and if I were to take it back to basics…that essence of kindness is really the foundation of what we do.

Think about it. Your job as a leader…is to make other people the best version of themselves doing the best version of what they do.

You literally care about other people for a living.

Your job as a leader of leaders is to help young leaders figure out their own personal reasons for doing that.

This was my journey. There many, many, many years of emotional skills training and trying to be “softer”. Then, there came a certain point in my career where I realized I could take off that “soft” mask just a little bit…and be a little bit more of my natural autistic, direct self, and still be ok.

Because despite my quiet weird directness on the outside, underneath it all, I really, truly cared very deeply about the people I managed and wanted to see the absolute best for them.

So, in my case it was a strange journey, because as I leaned back into my autistic view of the world, and become a little more direct, but also a little more authentic — it really become a powerful tool for me.

The directness reentering my leadership personality allowed me to more tactically and coherently address operational issues.

The hyperempathetic side of me I spent decades nurturing allowed me to do that with a true sense of kindness and caring.

I can’t place a pinpoint on the exact time I found that sense of balance, but I can tell the trajectory of who I am as a person and as a leader changed. At some point, my heart become a trillion times larger when it came to true emotional investment in leadership. My confidence became unshakeable from that point, and I’ve enjoyed every aspect of leadership since.

Our goal is to help young leaders reach that same point.

So, I will continue to tell young leaders, there’s no set of steps or instruction manuals on how to lead. Hopefully there are some good mentors and some guiding principles along the way that help you identify your own leadership journey. I hope some of my personal insights have been helpful. Feel free to leave some of your experiences along your journey or any of your own guiding principles you’ve encountered in the comments below. I will really enjoy reading them!