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One-on-One With Senior Leadership: 10 Tips For A Good Meeting

A one-on-one meeting with senior leaders can be a great way to build trusted relationships and work toward growth and development.

By Fellow.app  •   July 29, 2022  •   7 min read

When preparing for a one-on-one with senior leadership, it’s normal to feel nervous. But don’t let your nerves get in the way! A senior one-on-one is a, well, one-of-a-kind opportunity to spend time with a higher-up in the C-suite. 

Senior leadership one-on-ones are a great chance to talk about your long-term career goals, work through day-to-day challenges, and share all kinds of other ideas. Below, learn how you can make the most of your upcoming one-on-one – and what to do now to set yourself up for success later. 

What are one-on-one meetings?

A one-on-one meeting – also referred to as a “1-on-1” or “one-on-one” – is a meeting that gives direct reports and their higher-ups a chance to connect. Some one-on-ones will be between a team member and a manager. Others might be between that manager and a member of the senior leadership team. (And yes, management and leadership are different!)

A one-on-one with senior leadership is a great time for a meaningful, both-sides conversation about what’s working and what needs closer attention. Though some managers and leaders skip regular one-on-ones and wait until performance review meetings to give feedback and touch base, don’t fall into that trap. Skipping one-on-ones can lead to things getting lost in translation, so push for a weekly or biweekly one-on-one to keep all feedback timely.

Michael Lopp (Rands), the author of Managing Humans and The Art of Leadership, has the following to say on why regular one-on-ones are key. “The important part of regular 1-on-1s is not that information is conveyed, but it’s about you being consistent as a leader. What is more important than trust and respect in all directions on a team?”

Host productive one-on-ones

Level up your one-on-ones with senior leadership by using a collaborative meeting agenda. Plus, use pre-built meeting agenda templates to maximize meeting productivity. Try a tool like Fellow!

Free One-on-one Meeting Agenda Template

10 tips for a good one-on-one with senior leadership

Any good meeting, including a one-on-one with senior leadership, boils down to how you prepare for the meeting. Below, you’ll learn how to prepare for a meeting with whomever you report to so you can best use your one-on-one time. 

1Be prepared

When you prepare for a meeting – especially a meeting with senior leadership – it can decrease those pre-meeting jitters. It can increase your confidence too – you’ll know you’ve put in the work to have a great meeting. 

Preparation is great for the person sitting across from you too. When you show someone that you’ve taken the time to not waste their time, they’re likely to notice and appreciate the effort. 

Of course, you might have some questions on exactly how to prepare for a one-on-one meeting. It’s easier than you think! If you meet regularly with leadership, then preparing starts with creating a meeting agenda template. Include priorities, challenges, talking points, findings, and space for meeting action items. This way, you always have your basic agenda structure in place — you’ll simply change up the talking points or findings before each meeting.

Pro tip: Take advantage of Fellow’s pre-built meeting agenda templates to ensure you always come prepared!

2Try to establish a personal connection

Feeling intimidated by higher-ups at work is completely normal, but it’s probably unfounded. After all, your higher-ups are people too. A great way to get past your anxiety is to find some common ground and build rapport well beyond your one-on-ones. 

This way, you can ease into your one-on-one with non-work-related questions. Ask the leader across from you about their favorite baseball or the latest episode of that TV show you bonded over in the break room. Working relationships are about much more than getting work done, especially since the two of you spend a lot of time with one another. 

3Bring things you want to talk about

A meeting isn’t a one-sided conversation – you should prepare talking points and questions for your one-on-one. In other words, it’s the perfect time to pick senior leadership’s brain. 

For example, if you’re having trouble managing a situation between employees at work, ask the leader how they’d handle the challenge. You’ll get real-time guidance and problem-solving and see the thought process behind their decision-making. And sure, leadership will likely have topics to discuss too, but don’t shy away from taking full advantage of this opportunity to connect.  

4Talk about your career goals

If you’re meeting weekly with senior leadership, then you might get in the habit of only sharing your biggest questions and status updates. And while those discussions are important, another equally important topic is your career goals. Bringing them up can move your career forward and give you another topic for your meeting. Plus, it shows senior leaders that you envision a long and bright future with the organization. 

Marissa Goldberg, the founder of Remote Work Prep, has this to say about incorporating long-term goals into the one-on-one. “As a manager, I like to know what each of my employees are aiming for long-term,” she says. “That way, I can open up opportunities and encourage skill growth that will help lead them to where they want to be. I don’t make their growth choices for them. Instead, I listen to their dreams.”

5Go in with the right mindset 

One-on-ones are something to be excited about, so try to go into them feeling that enthusiasm. Changing your mindset from “Oh no, another meeting” to “I can finally ask senior leadership that question that’s been nagging me!” can do wonders. You’ll start to associate these meetings less with another task on your to-do list and more with opportunities to learn and grow. 

6Show your interest in the business 

Sometimes, you might feel unsure about an executive’s interest in your ideas, but they often do care about what you have to say. They typically want fresh and innovative ideas from the people working for the organization. So don’t be afraid to share that well-thought-out, well-researched idea you’ve been mulling over. They might be able to collaborate with you on the idea to build it out further and make it a reality. 

7Be confident in what you bring to the table

Confidence is key, especially when speaking with senior leadership – a group that wants to be sure you know your stuff. And sometimes, you can have all the facts and figures, but without that extra confidence, it might not translate. So do your research, come prepared, and speak with authority. Your leadership might have questions, but you’ll be confident you’ve done the work to share great answers and put their minds at ease. 

At the same time, confidence is just a baby step away from arrogance, which is a huge no-no during one-on-ones with senior leadership. Your goal is to walk the fine line between knowing your stuff and being humble enough to welcome feedback and suggestions. 

8Practice your conversation skills 

One-on-ones with senior leadership are a great time to brush up on your communication skills. You should always speak clearly and with intention, and you should also be an active listener. 

Take a moment to practice simply speaking with someone, whether it’s a team member or a friend. Notice the natural ebb and flow of a conversation — moments where you can ask questions to move the conversation forward. Good conversations are all about finding that balance between confidence and taking a step back to let the other person take charge on occasion. 

9Show your unique personal brand 

Part of being confident is knowing what you have to offer. In a way, that’s kind of like figuring out your own personal brand and promoting it. If you’ve ever posted on social media or looked at a social feed, you know how to take this step.

Here’s an example: Let’s say you’re a high-performing sales manager who nails every C-level meeting. You should leverage that skill during your one-on-one with senior leadership. Make it clear that you’re the go-to person in your area of expertise, and show your leadership all you have to offer. This can mean sharing your success secrets and proposing an idea to help the rest of the sales team improve. 

10Don’t get in your own way 

There’s always the potential to self-sabotage or get in your own way before you even get started. An easy way to avoid that is to get confident with all the above steps. Tell yourself that you have what it takes to build better relationships with senior leadership, and recognize and acknowledge your strengths. Then, just go from there — when you don’t limit yourself and your potential, you can really wow your senior leadership. 

Show up to your senior leadership 1-on-1s with confidence 

While work life can be stressful, senior leadership 1-on-1s are a great time to cool down, connect with higher-ups, and get the support you need. All the tips here can help you reach that goal with ease. And so can Fellow’s meeting software.

Before your one-on-one with senior leadership, both of you can use Fellow’s collaborative meeting agenda to come prepared and shut out those pre-performance butterflies. Plus, with Fellow’s Guidance tool, you can create, share, and review potential talking points for your one-on-ones. This way, you’ll always have something meaningful to discuss with your senior leadership – and an easy way to prove yourself. 

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