Issue 15: Building Trust with the Executive Team
A Chief of Staff usually works with one principal, but your relationships with the rest of the executive team matter too.
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How can a Chief of Staff establish trust with the leadership team?
When stepping into a Chief of Staff role, you work in lockstep with your principal and that relationship is the one that you uphold and serve as your first priority. But a commonly overlooked extension of this relationship is the bond and trust that a Chief of Staff must build with the rest of the leadership or executive team.
A common refrain I’ve heard from both new and seasoned Chiefs of Staff is that, though their relationship with their principal is highly trusted and secure, they have trouble breaking into the rest of the leadership team and getting buy in. IE: leadership wants to deal with your principal directly and not through you. This underserves both you and your principal in two ways: 1️⃣ Your principal isn’t able to delegate trusted decision to you because they ultimately have to deal with the stakeholders, and 2️⃣ you are being underutilized because you are unable to move the pieces on the board that you have been assigned.
In today’s issue, we’re going to talk about ways to diagnose this lack of trust and what actionable steps you can take to build the stepping stones to a stronger relationship with the leadership team.
1️⃣ Start before you start: Even before you start as a Chief of Staff, there are ways to begin planting the seeds to get the leadership team aligned with you. In your interview process, take the time to ask questions that begin to surface the obstacles and challenges that the rest of the team is facing and begin to present yourself as a potential solution to help alleviate some of these blockages. For example, you might ask:
Why do you think [PRINCIPAL] needs a Chief of Staff at this time?
Where do you find [PRINCIPAL] most and least effective?
What could a Chief of Staff do to help make your job easier?
Where do you want to be spending your time that you feel like you aren’t able to?
By hearing the team out and lending an active listening ear, you can start to understand a fuller picture of where the leadership team stands and when you start in the role, you can bring up this same information to gain a pulse check of where things now stand. If the problems are at a standstill, it’s an opportunity for you to think of possible solutions that you can suggest as new projects to your principal and the rest of the leadership team. If the problems have already started to resolve, you’ll still get points for remembering what you were told even prior to you starting and hopefully that will signal to the executive team that you are keeping their interests in mind as you begin your Chief of Staff role.
When Nicki Disz reflected on her interview process for her current role, she advised, “Meet with other key stakeholders not only to learn their perspective on what’s important to have in the role, but to win them over and build groundswell on your behalf!”
2️⃣ Get aligned with your principal to present a united front: When you first start in your Chief of Staff role, sit down with your principal to write out your job description. Priorities may have changed since your initial interviews and what’s top of mind can often shift quickly, especially at early stage start ups. Take the time to understand what your principal and company’s areas of alignment are and get clear on how you fit into the picture. Are you expected to be the project manager, the delegator, or an observer? Is your principal expecting you to be a stand in for them in certain meetings and/or situations? You can use the original job posting as a jumping off point but now you can get specific about what it means to put each of those responsibilities into practice. IE: Leading strategic initiatives - what are the initiatives that are currently in progress and how can you either be an observer to learn how things are run or are there easy ways you can be a contributing member and create some added value quickly (more on this in tactic 3️⃣).
Once you and your principal are in agreement with what your first projects and priorities will be, present this to the rest of the team. That way, both the leadership team and the rest of the company is clear about what falls under your jurisdiction and what still needs to be surfaced to your principal. When I started as a Chief of Staff, my principal took the time to introduce me to the team at the next all hands, stating that I was going to be working with him on client initiatives and that I would be responsible for internal operations such as HR, People, etc. As a result, employees knew to come to me if they had questions about payroll, insurance, benefits, and other related items, therefore freeing my principal’s time to drive forward on things like fundraising, partnerships, and more.
Keep in mind what you start working on will likely not be what you will be working on a quarter or six months from now so this “rewriting” of the job description should happen consistently and be a common touchpoint between you and your principal.
3️⃣ Look for the low hanging fruit: Using what you know about the leadership team’s top priorities and blockers, see if there are quick wins you can gain by checking things off a to do or automating processes. Chances are, there are some administrative tasks that the leadership team may not have gotten around to automating yet or things that are being done manually that don’t take up much time in the moment, but small blocks of time can quickly add up.
One opportunity I saw for myself was when our Chief Science Officer (CSO) wanted to thank contributors in our community by sending them a piece of branded swag. Given my background procuring swag at prior companies, I knew that this was a project I could knock out of the park and that our CSO’s time would be better spent interacting with the community instead of researching t-shirts and mugs. I offered to take the project off his plate and come to him once the designs were finalized and prices quoted. I teed the project up for him to check the approval button and earned some additional trust and respect from his perspective.
Later on in the year, the CTO and CSO collectively wanted to create a monthly newsletter that would go out to the community and subscribers of the company. Even though I had no technical expertise in the domain that we were working in, they came to me with the proposed newsletter format and even suggested a few platforms on which to host the newsletter on. They also gave their respective teams the heads up that I might be asking them for help on language and the more technical aspects of writing, thereby allowing me to use their team as a resource for a project that they entrusted me with but the end project would ultimately would reflect on them.
Looking for these collaborative opportunities to test the working waters will go a long way in getting you the access you need down the line when you need to get buy in on larger stakes projects and initiatives.
4️⃣ Take initiative but don’t overstep the bounds: Common fears that I hear iterated by members of the executive team when a Chief of Staff comes in is that they 1️⃣ may lose direct access to the CEO or principal that the Chief of Staff is partnered with or 2️⃣ have a feeling that the Chief of Staff is now there to spy on or micromanage them.
While both of these fears can be assuaged when both principal and Chief of Staff present a united front on what the Chief of Staff is there and isn’t there to do, you can also take matters into your own hands with your actions and interactions.
In your first few weeks as a Chief of Staff, you should be on a constant listening tour around the company. Again, have your principal set the precedent that this is part of your onboarding to be an effective Chief of Staff not only for them but for the organization as a whole. Ask if you can be an observer in the room for department meetings and other gatherings where your principal may not always be present but the information may help you form a better picture of the ins and outs. Reiterate that you’re not doing this to report back to your principal, but instead, by being a common thread in various rooms, you’ll be able to piece together whether or not there are multiple teams or departments working on the same thing when they could be more effectively working together.
Your role in these meetings is purely to observe and synthesize. Don’t feel the need to chime in or offer solutions. One Chief of Staff that I greatly admire stated that her cadence in these meetings were to listen (she sat at the end of the table if in person or video off/muted in Zoom) and if she heard anything that she might have additional insight into or that she knew was in direct conflict with what her principal may have told her, she would send a follow up message to the meeting leader to give them a heads up: arming them with information to make a different decision if they wanted to but by no means suggesting that it was necessary. You can take the initiative to offer up information that is relevant, but do not take it under your purvey to help them solution. Imagine yourself as an enabler, but not an executor.
5️⃣ Help them help you: Building trust takes psychological safety. In this Harvard Business Review article about cultivating psychological safety, it mentions 3️⃣ particular tactics that correlate especially well to the Chief of Staff role:
Admit your own fallibility.
Actively invite input.
Respond productively.
By opening up your own vulnerabilities and blindspots to the rest of the executive team, you would be surprised at the receptiveness of the rest of the team to lend a helping hand instead of seeing it as weakness.
In the newsletter example I mentioned above, when the CTO and CSO came to me to spearhead the newsletter, they were acutely mindful of my lack of technical expertise. In fact, in the first week starting as a Chief of Staff, I had stated that while I was not an engineer or scientist, I was happy to make up the knowledge gap by learning from others on the team and doing a lot of Googling. By surfacing this vulnerability from the get go, they were able to preemptively arm me with resources (the time and knowledge of their teams) in order to ensure a successful execution of the newsletter. They saw my admission not as a failure but an opportunity to help me learn more about the industry and a way that I could help them take on an initiative that they would otherwise need to spend additional time wrangling resources for.
As with anything in the Chief of Staff role, there isn’t a one size fits all approach to building trust with the executive team, but through these tactics and anecdotes, you can start to build the foundation of what is necessary to be in a successful relationship with not only your principal, but the rest of the executive team.
Additional Chief of Staff Related Reads:
Unlocking Your Inner Chief of Staff: Guide to Maximizing Organizational Impact - Leigh Felton
Spring Clean Your Executive Office
6 Steps To Being A Successful Chief Of Staff
🎥 Upcoming Workshops:
As a reminder, all upcoming workshops will be free for AaCoS community members to attend, but paid for other attendees. If you haven’t applied to join our community yet, you can join our waitlist here.
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This upcoming workshop will be led by Nancy (CEO of Moonhub) and Teddy (Chief of Staff at Moonhub) and will explore the dynamic between principal and Chief of Staff when it comes to early stage hiring. You won’t want to miss this one!
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👋🏼 Until the next issue,
Clara
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