Fancy Can Wait

Starting a new leadership role is both exhilarating and daunting, in equal measure. As such, while I am thrilled to join CyberCube as the company’s VP of Engineering, I’m also well aware that the appointment comes with expectations and requirements. Reporting up to the CEO, it’s an amazing opportunity to make an impact in the cybersecurity world by helping grow a high-performing engineering team at the cutting edge of risk quantification...?Now, I've got to deliver on that promise.

“Oh, the clever things I will do!” is the natural thought, but fortunately experience is a great teacher, and if there’s one thing I know it’s that before you build a skyscraper, you need a rock solid foundation. You see, the biggest mistake senior leaders make in a new role is trying to get fancy before they have mastered the fundamentals of their new environment. This article explores that a bit, and looks back in my career for places where I’ve seen too little time spent on the foundations of leadership and management - a lesson I’m committed to never forgetting.

The First 90 Days

Michael D. Watkins’ classic book The First 90 Days is a staple for anyone stepping into a leadership role; so much so that I make it a point to reread it each time I start a new job. However, even with a solid plan, no strategy survives first contact with reality.

The book encourages swift impact, which, when misapplied, can put tremendous pressure on a new hire to show quick results. That can be good - in a startup, where you need to move fast and break things, or in a turnaround where everything is already broken and nothing works.?However, for most businesses, you’re either “sustaining success” or dealing with a minor realignment of technology, people, and processes. In these situations, thoughtfulness wins every time. Watkins acknowledges this nuance, but new leaders often overlook it, rushing to “prove themselves” and unintentionally committing cultural missteps that are difficult, if not impossible, to repair.

My advice on this one is easy: if you’re going to read Watkins' book (you should!) read the whole thing, cover to cover. Don’t skip the parts you don’t like, and please don’t just cherry pick, because in context it all makes sense. Out of context is another matter, though, and if you blindly shoot for “impact” you may well come off as a complete lunatic. Worst yet, your cultural missteps may take you a long time to repair, and some of those mistakes won’t just buff out… they’re going to leave a mark!

The most important thing to do when you begin is quickly orient to the kind of organization you’re in, and determine what immediate action, if any, is required. Whether it is or isn't, I want to reinforce one simple idea: get the basics in place before you go out on a limb and do something “clever”. Foundations are foundational for a reason!

Start with the Basics

My mandate at CyberCube for the first 90 days was simple yet profound: “Meet the team and develop a long-term plan.” This focus on understanding people, processes, and culture sets the tone for thoughtful leadership. If you’re not given such clear direction, it’s worth advocating for—or creating—your own version of this roadmap.

So, what are the basics you should be focusing on??

1: Listen and Observe

When you’re first in an organization, it’s a bit dizzying. You don’t know the players or the relationships between them, and you don’t know the history. You’ve likely been through a pretty intensive interview process so you have a sketch of the organization, but that’s very different than working somewhere. Your job, initially, is to listen and observe. And I mean watch like a hawk. What’s said. Who’s saying it. What’s the body language of the speaker and the listeners? This is where remote work makes your life harder, but investing in really attentive listening will still pay you back, whether face to face or on Zoom. Confluence is great for learning, but the real education will come from the team around you. And remember, communication isn’t just what is said. It's much more nuanced.?

2: Clarify Roles and Expectations

Once you’ve gotten oriented, make sure you understand the different roles in your organization and the parts of the organization you bump up against. Before you are tempted to roll up your sleeves and “clarify” expectations for others (aka "tweak and change them"), clarify for yourself what they are, and where they are vague. Trueing things up can usually wait a little bit.

3: Communicate, communicate, communicate (and then communicate one more time)

Next, we turn to communication. You’re "the new boss", and people will be both nervous (what are you going to do, how can they make a great first impression, etc.). As such, there’s a lot of talking during onboarding and beyond.

In my case, my first few weeks have been a lot of calls. Meeting other executives, partners, and my own team requires a lot of talking, and it’s both life-affirming (I love meeting new people… people are cool!) and tiring. When my days are done, I flop on the couch, and turn on some John Coltrane to drift around in. It takes a toll (the calls, not Coltrane), but it’s well worth it. You have to be really clear in your communication; are you asking, telling, or suggesting? Your team doesn’t know you, so they’re going to want to show you what they can do, and that itself can create problems.

Pro tip: If you’re spitballing ideas in meetings, make sure to preface them as such to avoid unintentional projects popping up overnight!

4: Understand and solidify core processes

Engineering is only as effective as its processes. Are your product and engineering teams aligned? Where are the bottlenecks in your development cycle? Focus on simplifying and optimizing these fundamentals before experimenting with innovative solutions.

Why Fancy doesn’t work

Given that we have a great recipe for the basics, you might wonder why I am dead set against “clever” in the first 90. Well, the answer is simple: even if your new organization is well-grounded and operating well, you won’t really know that yet. Organizations, like plants, grow into their current shape for a reason. You’re coming into the organization, and maybe you can see that the shape is distorted. Okay, fine. It probably needs to change at some point, but before you get your virtual pruning shears out, you should stop and think. Why is it the way it is? If you don’t know - and I mean really know - why it’s grown up that way, the clever organizational tweak you’re about to make is likely to result in blowback or worse.?

Moreover, even if you’re lucky like me, and your organization does have really solid people and foundations, you should still resist the urge to get clever with things. Yes, everything is in place, and yes, you have talented people. But there is so much you don’t know. You need to find your footing first. Fancy will get in the way of things, and you won’t have earned the trust of the people around you yet, nor will you know how they like to receive new ideas, praise, or constructive feedback. All those things need to be in place before you roll your sleeves up and do something that’s “clever”. I can’t state this strongly enough: the basics exist for a reason.?

Lessons from the Trenches

Trying to think of examples I’ve witnessed here is difficult, because I want to keep everything anonymous. However, I’m drawn to two experiences I’ve witnessed from my own career:

• The “All-In” Decision. I have witnessed an incoming executive making a hasty, consequential - and ultimately risky - personnel decision. Their choice - while bold - was based on limited information and an incomplete understanding of the culture of the organization. It was clever, aspirational, and “fancy”... but utterly wrong. What followed was misalignment, churn, and bottom-line fallout. Don’t paint yourself into a corner when you don’t even know where the walls are!

• The over-engineered Solution. In another instance, an incoming manager couldn’t resist the “fancy” solution to a capacity problem. While there was certainly a challenge to be addressed, there were much simpler solutions available. Instead, a complex organizational extension was hurriedly set up. It worked for a while but ultimately had to be rolled back. Employees bore the brunt of this failure, and the organization was left back at square one.?

In both cases, simpler, more culturally-effective solutions would have avoided costly mistakes. Business is about risk, I get that… but it’s about controlled risk, not gambling.?

Final Thoughts

As I get settled in at my new job, I realize I’m very lucky. I have a smart team around me, and the culture is good: we’re aligned on our mission and vision, and things are taking shape nicely. However, even that can be a snare, because the tendency is then to move quickly once again, and I have to keep reminding myself that I’m still getting oriented. Impact is good… but I want it to be the right impact. Given that my team is awesome, I should look very carefully at any improvements, because they’ll have already considered them, and opted to pass for a reason.?

I've learned a lot from playing sports, and I can't resist closing with a tennis analogy. Leadership, like tennis, is about mastering the basics. Fancy shots may win points, but solid footwork and technique win matches. So whether you’re stepping into a new role or navigating familiar territory, don’t worry so much about being clever. Focus on laying a strong foundation—for yourself and your team. From there, the sky's the limit.