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What they don't tell you about being an executive

The corner office (ha! Remember offices?!). The coveted title. The authority. These might be what many envision when they think of executive roles. However, the road from being an individual contributor to a manager to an executive in charge of an entire function is one that is much more of a winding road than the traditional image of a "ladder." Or maybe it is a ladder, but with countless rungs missing.

I've had the privilege of spending time as an IC, a middle manager at a large organization, an executive at a few small companies and many things in between all of those worlds. And I don't in any way consider myself an expert in this area - but I have learned a lot from my mistakes and by reading and listening to other leaders who I look up to. And so I wanted to add my small story to this corpus, and hopefully point folks in the right direction as they build their own careers. At the end, I've included a number of references from people much smarter than I so that you can continue learning from some of the best executives in technology.

Executive Team as Your Primary Team

Perhaps the biggest shift from being a front-line manager or an IC is where your primary team lies. Traditionally, most folks think of the function they are working in as their number one responsibility. So it would make intuitive sense that when you are leading that function that it would be clearly your number one priority. But when you're on an executive team, it’s actually more important to firstly be a member of your own executive team.

Patrick Lencioni in "The Advantage" provides a compelling argument for the latter. He states that members of a leadership team should give precedence to their roles within that team over the teams they individually lead. While it might seem natural to prioritize one's own department or function, such a mindset is fraught with risks. It inadvertently turns the executive group into a lobbying faction, each pushing for their department's interests, rather than collaboratively deciding what's best for the entirety of the organization.

This shift in priority is not just a theoretical construct, but has tangible repercussions on the ground. Employees within departments want a cohesive and aligned leadership team, as the decisions and directions of this group directly impact their success. Chaos or a lack of unity at the executive level frequently leads to inter-departmental conflicts, hindering progress. Understandably, some leaders might resist deprioritizing their immediate teams. After all, it is the function of their role to oversee that team. However, Lencioni argues that such a shift is vital, not for hierarchy but for building a truly cohesive, integrated, and healthy organization.

Meetings as Actual Work

Okay, let's address the number one elephant in the executive room...meetings. I almost led with this, as I think it is top of mind for many, many leaders. Especially in a world where many people have shifted to remote work without having specific intention around that shift, it can be a real struggle to understand when a meeting is valuable versus a "waste" of time.

My father plays golf with a Director at a large engineering organization, and in the post-COVID remote world (without adapting their work practices) they talked about being on Zoom meetings from 7 am to 7 pm every day. This is perhaps the obvious extreme, where it’s clear there are more meetings than are valuable- but where is the line? When you're an IC, many meetings can feel wasteful...but that line is different as you move into leadership.

As Satya Nadella, CEO of Microsoft, said, "You have to create clarity where none exists.” That clarity often originates in these very meetings, setting the direction for the entire organization. And since driving that clarity is the most important thing you can do as a leader, you have to start seeing meetings as vital parts of your job. That's not to say you shouldn't make sure they are effective - I've seen LOTS and LOTS of ineffective meetings in my day. In fact...note to self: write an article just on running effective meetings.

Once you've got that muscle of effective meetings worked out (and like a muscle, always working at it and improving, so it doesn't atrophy), your team, both the executive team and your functional team, will benefit. As Sarah Drasner put it in Engineering Management for the Rest of Us:

I get it; engineering teams like to . . . do engineering work! No one likes a lot of meetings, but getting a group together is valuable time spent. Your team needs to see one another with a regular cadence. They need to talk through their work, discuss issues, and hang out a bit. 

Meetings are part of the job. Make them count.

The Evolution from IC to Executive

Shifting from an individual contributor to an executive isn't just about scaling tasks. It's a paradigm shift. Instead of diving deep into the 'how', executives often navigate the realms of 'why' and 'what'. 

There is a pretty blunt story about this that is in the folklore around Apple founder Steve Jobs. The story goes: when employees rose to the position of vice president at Apple, Steve Jobs would share an anecdote with them. He'd describe a scenario where if the trash in his office wasn’t taken out, he'd ask the janitor why. The janitor might reply, "The door lock was changed, and I didn’t have the key." This excuse is acceptable because a janitor needs access to complete his task. In his position, having such reasons is permissible.

Jobs said to his new VPs, "For the janitor, reasons are valid. But as you move from the janitor's role up to the CEO, those reasons become irrelevant." He would say that the line between reasons mattering is somewhere between a janitor and VP at Apple, so now that you were a VP, the reasons for something no longer mattered, the outcome matters.

Perhaps a more positive spin comes from Drasner in Engineering Management for the Rest of Us:

Try to work on aligning people to the outcomes you are looking for from them. You don’t have to code it all yourself, you need to articulate why the code is necessary, and what it will need to do in order to accomplish this. Trust in them to figure out the hows and consult when they need guidance. 

When you're an IC, the code you write and the things you produce matter. As you move to being an executive, your job is the alignment to the outcomes as well as the outcomes themselves.

Giving Agency and Prioritizing People

With power comes responsibility, particularly in decision-making. GitLab introduces the concept of the Directly Responsible Individual (DRI), streamlining decisions by assigning a clear owner. However, this doesn't exclude team input. Everyone should have the chance to voice opinions, even disagreements. Once a decision is made, commitment is crucial, but internal discussions can continue, ensuring the path taken is truly the best one.

Give individuals the autonomy to prioritize tasks they find most valuable. If a meeting doesn't appear essential and a person's involvement isn't crucial, allow them the choice to skip it. "Trust in them to figure out the hows and consult when they need guidance." Empower every team member to act as a manager of one, eliminating the need for daily check-ins to meet their objectives. Grant them the autonomy to take charge of projects and initiatives, trusting them to drive successful outcomes.

The wisdom encapsulated in Ben Horowitz's quote, "Take care of the people, the products, and the profits — in that order," serves as a guiding principle for any successful organization. It underscores the idea that the well-being of employees should be the foremost priority, as it is the workforce that drives innovation and productivity. When the team is motivated and aligned, superior products naturally follow. Profits, though important, come last in this sequence. They are often the result of an engaged workforce and exceptional products. In prioritizing in this manner, leaders can build a sustainable, healthy, and profitable organizational ecosystem.

So, now what?

In the dynamic landscape of leadership, the role of an executive is often romanticized, if not grossly misunderstood. While some paint a picture of grandeur and ease, the reality is marked by challenging decisions, nurturing talent, and striking the delicate balance between individual departments and overarching organizational goals. Regular meetings are not mere calendar fillers; they are the compass by which a company navigates its future. 

Being an executive is a journey, not of solitary leadership, but of collective progress and alignment to values; it means changing your perspective. You move from doing things yourself to having a broader vision that empowers and impacts others. It's rare that an IC's decision will affect the future livelihood of other team members, but executives make those kinds of decisions every day. Great executives understand the big impact of every decision and realize that disagreements with those decisions are inevitable. However, unity in the execution of those ideas is key. Most of all, being at the top of an organization isn't just about driving growth. It's not even mostly about driving growth. It's about creating an environment where people are empowered to innovate and are encouraged to prioritize what's essential: family, friends, and their well-being.

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