Issue 20: Working with Engineers & Technical Roles as a Chief of Staff
If you don't have a technical background, how can you work best with those who do?
Welcome back, aspiring and current Chiefs of Staff!
This week’s issue is brought to you and guest authored by Flywheel Executive Coaching. Founded by Katherine Huang, former Chief of Staff at Bubble and Hyperscience, Flywheel Executive Coaching offers coaching services to tech and finance leaders, entrepreneurs, and anyone seeking to make a positive change in their career.
You might even recognize Katherine from our previous workshop, Establishing Trust with Your Principal, or as an instructor from the Chief of Staff School.
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How do you work with engineers and other technical roles if you’re non-technical Chief of Staff?
Many Chiefs of Staff come from “non-technical” or generalist backgrounds, and are hired for their experience in business operations, project management, cross-functional communication, and other generalist skills.
In your Chief of Staff role, you may be reporting into a CEO or another executive with a “technical” background despite not having this background yourself. You may also find yourself working with a VP of Engineering or other engineers on cross-functional projects, project management, recruiting, and other initiatives.
In this week’s issue, we’ll be talking about 5️⃣ tactics you can use when working with technical talent so that you’re able to optimize the relationships you build with them and help each other accomplish the goals of the org.
📚 Aim to understand the lingo
If you’re joining a team where the technical vernacular is new to you, look for resources where you can give yourself a baseline understanding of what the technical ideas are. Is there a company knowledge base where you can read up on key technical terms? If not, it might be helpful to suggest this as a project for you to work on and use it as a wiki in the future as the company continues to hire roles that are non technical (HR, Talent, etc.)
Additionally, seek out a friendly colleague for a coffee chat or 15-minute Zoom to answer any questions that arise as you’re studying these terms. When engaging in these types of conversations, lead from a place of curiosity. The benefits of doing these are two fold: 1️⃣ You’ll learn more about the technical elements of your company from the lenses of someone who works there and 2️⃣ When you approach people with curiosity and humility, they feel validated and that leads to connection. These relationships will prove useful in the future when there are projects and initiatives that require cross functional collaboration.
*Note from Clara: I share an anecdote where I was responsible for writing a technical newsletter in a previous issue, despite having no technical background myself. It was because of these initial conversations that I had with engineers and scientists prior that made that initiative a success.
🔍 Seek to understand individuals
Similarly, try to learn as much as possible about the technical teams in order to maximize your success when collaborating with them. Don’t just limit yourself to talking to heads of departments or managers. Take time to chat with individual contributors as well and understand their challenges at the micro levels.
Some key questions you might ask as you go on your listening tour through the organization:
What is their reporting structure - is there an opportunity to help craft an org chart to help bring transparency to the team as well?
Where are there challenges in working with other stakeholders? Are there specific blockers or obstacles preventing them from completing their work?
What are the team’s OKRs and biggest roadblocks to achieving them, either internally or externally?
These are all important aspects to learn, yet they don’t require a specific technical background to understand. When things do get more technical, ask your teammates to explain further and direct you to additional resources that might help you paint a better picture of the challenges they’re dealing with. Additionally, this will give you more insight into the org as a whole as you see where there might be disconnect from the IC and leadership levels.
There’s also opportunity here to craft user manuals for folks on the team so that not only do you get further insight into how to work with individuals, the whole team can benefit from taking time to understand how their peers and coworkers best work together.
👀 Look for quick wins
Quick wins are always a great way to knock out a series of to dos while building stronger relationships with those who you’re looking to work more closely with. For example, can you streamline and document a repeatable process that was previously being done ad-hoc each time? Can you spot areas for improvement in their project management process? When speaking with engineers, are you hearing a common issue that you can communicate to the appropriate stakeholder, such as confusion about a certain HR policy?
Oftentimes, engineers and other technical talent don’t need help with the hard skills of their roles, but instead, there are problems that arise with communication, progress updates, or cross functional collaboration. As a Chief of Staff, you’re uniquely positioned to pattern match and see common threads that arise and create processes to help alleviate those issues.
In an added bonus, you might even see how these challenges might run counter to or clash with company culture or values. If this is the case, you can use the opportunity to either reiterate company values or call attention to the need to strengthen or reevaluate them.
🖼️ Add structure where needed, but keep an eye on efficiency
As a Chief of Staff, you are able to experiment and iterate on process and structure because you have a high level view of what the organization’s operating rhythm and cadence looks like.
Establishing the right structure starts with following best practices yourself. A common occurrence for a Chief of Staff reporting to a principal with a technical background (or any busy executive, regardless of background!) is that the principal may believe that ad-hoc conversations will be sufficient and save time, versus scheduling recurring 1-1's. While there is merit to having more off-the-cuff conversations at times, there is also consistency in communication where a recurring meeting is present. To add structure, you could speak up and suggest that a weekly 1-1 could be a more effective way to work together and build a strong rapport. The standing meeting time could be blocked off in advance and only acted upon if there is a clearly proposed agenda - the onus of which is on you as a Chief of Staff to provide. Another suggested format is to have a recurring agenda where you can provide updates and feedback to your principal and vice versa.
Similarly, if you spot gaps in communication between engineering leaders or between the engineering and customer success teams (for example), and have context on the issues that need to be discussed, offer to set up and facilitate a meeting to help work through these. On the flip side, and equally important, if and when meetings are no longer needed, be ruthlessly efficient in canceling them to free up time on everyone’s calendars.
👯♀️ Don’t Go at it Alone
You were hired for the unique experience and diverse background that you bring to the table. By taking a cross-functional approach, you can successfully work with all types of roles and teams. When doing so, remember to dive in with the right balance of confidence and self-awareness, which will help you make the most out of your Chief of Staff role and add value across the organization.
Additionally, remember that you may be the only Chief of Staff at your company, but you’re not the only Chief of Staff that exists in the world. The number one piece of advice I can give to any Chief of Staff is to find others in similar positions and build your own brain trust around yourself. Finding a community of other Chiefs of Staff will help give you perspective and advice when you deal with challenges, such as working with technical talent.
In anticipation of Q3, Ask a Chief of Staff is reopening its waitlist and accepting new members. If you’re an aspiring, current, or former Chief of Staff, we’d love for you to join us in our Slack community to share best practices and knowledge with each other.
Hope you’ve enjoyed the latest issue of this newsletter and we’re looking to you for future newsletter topics! If you have any questions around being a Chief of Staff, tactical takeaways that you can apply, or other curiosities about the Chief of Staff role, submit a question below and we’ll answer it in a future newsletter issue:
🎥 Upcoming Workshops:
July 19th: Moving from Imposter Syndrome & Inner Critic to Inner Guide
As a reminder, workshops are free for all Ask a Chief of Staff community members and the recordings will only be provided to members and registered guests. There is a suggested ticket price on all workshops on but the first 25 registrants can waive your ticket price with code ASKACOSREADER.
Additional Chief of Staff Related Reads:
Career changers: Networking isn’t enough
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👋🏼 Until the next issue,
Clara
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