Issue 31: Giving Upward Feedback to Your Principal
Receiving feedback is a necessary trait of a Chief of Staff, but so is delivering feedback.
Welcome back, aspiring and current Chiefs of Staff!
This week’s issue is written by McKay Roozen, executive coach for soon-to-be executives. She helps mid-career high-performers take ownership of their career to create more impact. Her clients change the trajectory of their careers by gaining clarity on their goals, making big career changes, and improving their performance – all while gaining a sense of personal and professional fulfillment.
McKay is giving Ask a Chief of Staff readers an exclusive opportunity to start 2024 off with a bang! If you enroll in one of her personalized, 1-to-1 coaching programs with a January 2024 start date, you get a bonus 60-minute strategy session and an extra week of asynchronous access to McKay (valued at $750). Must enroll before December 8th - schedule a call here.
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How can a Chief of Staff best give upward feedback?
As a Chief of Staff, you’re serving as the right hand to a high powered executive. It’s a given that they’ll be giving you feedback on the quality of your execution and it’s in your best interest to proactively ask for feedback so that you can continue to grow in your career.
On the other hand, providing upward feedback might feel like a daunting task and it might even seem as though you’re adding more responsibilities to your principal’s workload. The truth is that offering upward feedback presents an opportunity to ease an executive’s burden and simultaneously create more equity value.
From Mesh.ai, “When done correctly, upward feedback can lead to better manager performance, more decisive leadership, improved team morale, increased team performance, and a better work environment overall.”
As a Chief of Staff, you’re uniquely positioned to collate and deliver highly strategic and important insights that can improve your principal’s performance to help them win. When they win, the company is able to deliver more efficiently and your work also becomes more impactful as well. Your upward feedback will not only improve the relationship between you and your principal; it also has the potential to improve your principal’s relationships with their leadership team and other key stakeholders in the organization.
Here is a process and procedure you can leverage to deliver feedback in an effective and encouraging way:
1️⃣ Gather data and identify the problem 🔎
Your first step is to prioritize what feedback you want to share with your principal based on what’s needed at a company level and at an executive level. As you’re deciding importance, start at a high level and reflect on the company’s trajectory over the past several months. Consider how your principal supported the tailwinds or contributed to the headwinds. Then, reflect on the role their management skills play in that dynamic. Your key question for reflection is:
What changes can your principal make to improve the company trajectory?
Zooming out a bit, it’s helpful to consider if there are any repeating patterns that you’ve noticed. For example, if your principal has a habit of speaking over other voices or has a hard time prioritizing, your ability to pattern match can be a huge asset to them. Consider:
What are your principal’s patterns and blindspots?
It’s also important to ask yourself if there’s an elephant in the room. In my work with high performers, they are often frustrated by their executive team’s inability to see the problem that’s right in front of them. I call this “the work at the center,” and strategically bringing attention to the thing that no one is talking about can be a tremendous way to build your soft power. The key question here is:
Is there a glaring business problem that no one is discussing?
Lastly, consider the actions you believe should be taken to improve the company’s success. As a Chief of Staff, you’re positioned to shape the future of the company, but you can only do that if you have a POV on how that should be done. Gather feedback by defining your vision for the company and how you want the culture to evolve. Ask yourself:
Where do you want the team and/or company to be this time next year?
What needs to happen at an executive level to get there?
Just like it’s your responsibility to help your principal prioritize key initiatives, it’s your role to prioritize and pace feedback. Assume that they can change one thing (at best, two things!) at a time. Narrow down your feedback and consider:
What is the most urgent problem to solve based on the company’s stage and needs?
Is there one piece of feedback that could solve multiple problems?
2️⃣ Structure the feedback 🏗️
Determining what feedback to give is as important as deciding how to share it. Start with empathy. Like anyone else, your principal has goals, pressures, and expectations for themselves. Understanding what they care about will help your feedback land better – and it’ll make it easier for you to manage up in the long run. Reflect on:
Where does your principal want to be in 5/10/15 years?
What pressures are they feeling from the rest of the leadership team, the Board, and their direct reports?
Next, it’s important to ask yourself why they haven’t already made these changes. Consider your own blindspots or assumptions here and reflect on what they have to lose if they take your feedback. Related to the prior point about prioritization, it’s important to orient this feedback in the context of their other priorities (more food for thought in this HBR article). Ask yourself:
If the problem feels obvious to you, then why haven’t they fixed it already?
How does the necessary change align or clash with their individual goals and/or the company’s goals?
You not only want this feedback to land in the moment, you also want to see change. Thus, it’s important to determine your role in helping them successfully implement this feedback. Map out your own expectations, both in terms of what “good” looks like and over what time period. Be realistic! It’s also important to help in the creation of the solution: co-creating the actions post-feedback will lead to better retention and sustained change. The primary question here:
How are you planning to help them close this gap?
3️⃣ Plan for the conversation 🗣️
Get ready for the conversation itself and think through the best way to deliver the feedback. Consider the time, place, tone, and the examples you want to use (more tips on that here). Knowing how your principal likes to receive feedback will also make the conversation go smoother. Ask yourself:
Do they prefer written or verbal feedback?
Do they want to sit with the feedback for a day before discussion or would they rather tackle it head on in a conversation right away?
Additionally, it’s always a good idea to root the conversation in what they care about (ex. revenue, growth, impact, team alignment, etc.) while also considering what they might be afraid of. Prioritize the former and avoid the latter when you frame the feedback. Reflect on:
What does your principal care about and what are they insecure about?
Perhaps most importantly, think through your expected next steps. Consider what sequence of action you want them to take and how you can help them do that. Remember, it’s as much your responsibility to deliver the feedback as it is your responsibility to help your principal take action. Consider the following:
What’s the action you want them to take and how will you communicate that expectation?
Lastly, map out the worst-case scenario. Think about how things could go sideways, not only as you’re giving feedback, but also after the conversation itself. Identify how things could be misunderstood, misheard, or misremembered and structure out the conversation accordingly. Ask yourself:
How can you de-risk the conversation?
4️⃣ Follow through and follow up 🛣️
After delivering the feedback, you’re probably eager to see your principal take action quickly. But the reality is that change is hard for everyone – especially for executives who are juggling multiple responsibilities and may have been working in their styles for years, if not decades! Assume they have good intentions and ask yourself:
Are my expectations aligned with their pace of change?
If you’re observing your principal incorporating these changes, wonderful! Let them know that you appreciate their effort and acknowledge the progress. But, if you’re not seeing change as quickly as you’d like, it’s time to regroup and try again. Perhaps it’s simply a matter of reminding them of the feedback and why it’s important, or it could be an opportunity to deliver the message differently.
Alternatively, it can be an opportunity to reconsider what pressures your principal may be facing or what is happening in the background of which you’re not unaware. Look for clues from their action or inaction and consider:
What do their actions reveal about the pressures they’re experiencing and/or your own blind spots?
5️⃣ Decide your feedback cadence ⏲️
So, you’ve given upward feedback to your principal and the conversation went swimmingly! Now what? Ideally, giving and receiving feedback happens on a regular cadence and not just during an occasional conversation. As a final step, make a plan for how you’re going to give input to your principal on an ongoing basis. For example, you can bake it into your regular one-on-ones, performance reviews, and project post-mortems (more ideas here from BetterUp). A question to ask yourself:
What cadence of feedback best serves your principal and allows them to make timely improvements to their performance?
Remember, everyone – especially your executive – deserves supportive feedback and directive guidance. When you approach your relationship with your principal with agency, empathy, and a sizable dose of strategy, you’ll change the trajectory of your career and further establish yourself as a strategic and trusted advisor.
Special thanks again to McKay Roozen for co-writing this issue with us! Schedule time with her before December 6th to take advantage of her end-of-year deal!
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Additional Chief of Staff Related Reads:
Seeing around corners: How to excel as a chief of staff
How to Write A Resume and Get Interviews