Preparing for my next role

Now that I’ve wrapped up my time at Microsoft, my attention is shifting towards my next job, where I’ll be working as a Technical Advisor to a CEO.1 I had the job title in my previous role at Microsoft for Startups, but the scope of that role was for a small team, not a company.

The description for the new job starts with:

You’ll work directly with the CEO and senior leaders to deep dive into some of the company’s most interesting technical challenges and bring perspective. You’ll connect the dots, ask hard questions of the teams, and point out great ideas and flawed designs.

My first reaction: “Awesome! That’s definitely something I want to do.”

My second reaction was “Shit! That’s a lot to do. I gotta get ready!”

The role of a Technical Advisor isn’t a common one. And, it’s a hard one to measure success for. So, I started asking questions. The first person I asked for advice was Mat Velloso, who currently serves as Satya’s Technical Advisor at Microsoft. He laughed when I asked him my questions, saying, “I interviewed every one of my predecessors in the role and asked them the same thing.”

A lot of what Mat told me really popped into focus a few days later while reading a beta copy of Staff Engineer by Will Larson. There was one particular sentence that just jumped out:

Much as the Lorax speaks for the trees in his popular children’s book, staff engineers speak for their companies’ technology.

This encapsulates the spirit of what Mat told me. Most people on Satya’s team manage large organizations and represent the needs and opinions of those groups. Mat is there to provide a counterweight to those needs and ideas, focusing on Microsoft’s technology portfolio as a whole.

So, how is that different than being a Chief Technical Officer (CTO)? Well, first off, the position doesn’t include the word “Chief” or “Officer,” both of which come with a lot of other responsibilities and accountabilities. It also depends a lot on the kind of CTO a company has. Werner Vogel’s post about the different CTO roles is helpful here. A Technical Advisor should complement and extend the capabilities of a leadership team, not just the person who they report to.

That brings me back to Will Larson’s four common archetypes of Staff-plus roles. Using this framework, a Technical Advisor is a “Right Hand”:

The Right Hand extends an executive’s attention, borrowing their scope and authority to operate particularly complex organizations. They provide additional leadership bandwidth to leaders of large-scale organizations.

Thinking about it this way and how the role bridges the other archetypes’ work (tech lead, architect, and solver) with the executive team really brings a lot of clarity to how to approach the role. Of course, there are a lot of limitations to being a right hand.

While they leverage an executive’s authority, they’re not necessarily the person that people want to talk to. They also need to stay closely aligned with their leader’s approach and values to be effective. I’ve had some advice that the best way to handle these limitations is to not have, or at least suppress, a personal opinion. There is an appeal to do that, but taking it too far would limit the role’s effectiveness, I think. Certainly, I don’t think Mat follows this advice too much.2

Obviously, with a couple of weeks to go before I start, I’m still knee-deep in defining how I want to start addressing the challenges that will come with the role. Some of the books that I’m using to prepare are:

Several of these books aren’t about technical topics, and I’ve read many of them in the past. A good review, however, is something that I’m doing to get ready. Here are a few other suggestions from folks:

• The Art of Leadership, by Michael Lopp
• Drive, by Daniel Pink
• Creativity, Inc., by Ed Catmull
• The Culture Code, by Daniel Coyle
• Predictably Irrational, by Dan Ariely
• The Upside of Irrationality, also by Dan Ariely
• Accelerate, by Nicole Forsgren, et al.
• The Customer Driven Playbook, by Travis Lowdermilk and Jessica Rich

Thanks Bill Dudney, Larry Wright, Ian McDonald, and Mat Velloso (again!) for those. Any other suggestions? Please don’t hesitate to send them along.

1. I know I’m being vague as to who I’ll be working for next — all in good time, dear readers. All in good time. ↩︎

2. You can get a good sense of Mat’s opinions and take on life through his Twitter feed. He often brightens my day with a quip or observation. ↩︎