We recently sat down with Meghan MacRae, Operations Manager at Flipp to talk about how she approached her one-on-one meetings. From the change in being a peer to manager, all the way to juggling to manage 18 reports, Meghan covers it all! 

For those who don’t know, Flipp is a retail technology company that works with the largest retailers in North America and connects them with millions of users looking to save on their weekly shopping. 

Quick facts about Meghan:

• Works at Flipp (450+ employees) 💪
• Has 18 reports (6 coachees and 12 indirect reports) 👩🏻‍💻
• Her team is onsite with a flexible working policy, allowing team members to work remotely for part of the week 🏡
• She is a first-time manager 🥇

With such a large team, how often do you have one-on-one meetings?

At Flipp, we have a different structure than most teams meaning that I have one-on-ones with both my coachees and indirect reports. I meet biweekly with my coachees for formal one-on-ones and monthly with my indirect reports. However, with such a big team I want to make sure that in addition to formal meetings, we are communicating on a regular basis. That’s why I also have daily and weekly touchpoints with everyone on the team. 

How long are your one-on-one meetings?

My one-on-ones typically go for 30 minutes. However, sometimes I’ll add more time to the meeting if:

• We’re focusing on skill development
• My direct report requires performance management
• There’s more than 30-minutes worth of items on the agenda that they would like to cover

Why are you having one-on-one meetings?

As a new manager, one-on-ones are a great platform to build relationships and rapport with folks who were once my peers, and are now my reports. I use this time to understand their career goals, strengths, and areas of opportunity, but I also encourage the team to come to these one-on-ones with their own agenda as well. By building a mutually beneficial relationship based on respect, I’m building a safe space to have healthy conflict, tough conversations, and provide feedback that is not taken personally by them or myself.

How do you prepare for your one-on-ones?

The day before any one-on-one, I will scan through the notes from our last meeting, to ensure that I’m prepared to continue any conversations that were had. I also come prepared with my own list of questions. If a coachee wishes to use the time to work on skill development (i.e. communication skills, objection handling, or on the spot problem solving), I will come prepared with various scenarios that we can work through together. Additionally, I will also gather additional resources like articles or real-world examples in order to provide my coachee with as much support as possible. 

I recognize that I am not an expert in everything, so I do my best to empower my coachees to seek mentorship outside of myself, this includes providing them with a list of resources, podcasts, TED talks, and fellow team members across the organization that they can reach out to and learn from. 

Do you use a meeting agenda?

Yes. However, the agenda will differ for every individual. Generally my agenda will at least touch on the following topics: 

• Discussing top priorities
• Build on or check in on growth plans
• Share and discuss feedback (both ways)
• Reflect on the past and seek improvements

I try to focus one-on-ones on career, skill and self development, feedback and building rapport, but each one-on-one is a bit different for me. I coach for a variety of roles, from Operations Coordinators all the way to Operations Leads, and coaching is not a one-size-fits-all experience. The way I see it, I coach humans who are complex and have very different needs from one another. I think about how I like to be coached and use my experiences to coach others in the same way. 

Who owns the meeting agenda?

Both me and my direct reports. One of the great benefits of coaching is that it is a mutual relationship and you get what you put in. It’s important for me as the coach to set up a structure and purpose for every individual one-on-one so that expectations are clear. One of those expectations being that my direct reports are just as accountable for the meeting agenda as I am. 

If I’m coaching a newer member to the team, I’ll typically own the agenda for the first 3 months. This ensures that these direct reports are getting the support they need. For most, this is their first experience having a coach in a professional setting and I find that they typically require more direction at the start. As they get more comfortable in their role, and with the culture of the company, the ownership switches to the coachee to come prepared with an agenda. 

What are your go-to one-on-one questions?

Ice breakers

For these types of questions, I’ll generally ask about their previous work experience. I also often ask my new coachees to complete a Myers Briggs test, so that we can have some discussion about personality types. I’m an INFJ and we talk about what that means for me.

Starting each meeting

I love to ask questions that will get my coachee’s talking, including: 

• What have you been up to this week? 
• Looking back on the month, what would you say was your biggest accomplishment? What are you most proud of?
• Looking back on the week, is there something you wish you had done differently?
• Did you face any challenges? 
• What do you enjoy about the work you are currently doing?
• What do you not enjoy about your role? Why? 

Supporting my coachees

If a coachee comes to me for advice, I almost always will ask them what they think first. This allows me to assess how they would approach a situation and advise them accordingly. This is my preferred method because it allows me and my coachee to come up with a solution together. 

I also ask questions about how I can directly support them, including:

• What can I do to support you?
• What was the biggest takeaway from our discussion today?

Feedback

I frequently ask my reports and coachees for feedback. Every time I ask, I make sure to reiterate what my goals are as their manager and things that I’m working towards professionally. I’ve found this process extremely helpful when asking for feedback because they’ll usually have some ideas that will help me progress, and as a result, improve our relationship over time.

How do you encourage your direct reports and coachees to open up?

I’m vulnerable and empathetic. I think that in order to get a coachee or report to open up, you need to lead by example. I will always share my goals, areas of opportunity, and admit my own mistakes. I find that by doing this, it helps to create a safe space and allows them to feel more comfortable sharing whenever they’re going through a rough time. When I was new to the workforce, I assumed that my coaches/managers had everything figured out; they knew everything. However, once I realized that this wasn’t the case, it became much easier for me to open up and relate to them.

When asking questions to get someone to open up, I will try and start with:

• “I know when I was new to Flipp, I felt… How are you feeling so far?” 
• “I know coming to a company with such an open culture can be an adjustment, especially when coming from a corporate background, how are you finding the transition? 

Asking questions that touch on my own experiences can help show them that it’s okay if they’re going through something similar.

How did you handle the transition from working with peers to managing them?

It was definitely an adjustment. My approach was to have one-on-ones with my direct reports to discuss how expectations will be changing for both of us. In these meetings we discussed how, although my role has changed, I still expect feedback from them and that they can expect the same from me. We also talked about how I would now be less present at my desk (as my days would be tied up in meetings), so we walked through the best ways to reach me. These conversations may seem mundane, but they helped a lot with the transition, and provided a safe space where we could talk about what we were nervous and excited about.

Like I mentioned before, showing vulnerability can really help build rapport and trust. I was very honest and shared that it would be an adjustment, and it may be awkward, but we will get through it together.

I will say that this gets easier and easier to manage as time goes by, when the team starts seeing me in action in my new role. I think it also gets easier as newer team members join, who have only ever known me as Manager Meghan—so I don’t have to battle so much with the expectations of my former role.  

What’s your biggest challenge when it comes to one-on-ones?

I think with the nature of working in operations, the folks I work with are highly detail oriented and hold themselves to extremely high standards, which is an awesome thing. Where I find it challenging in our one-on-one’s is that they can focus quite heavily on their areas of improvement, or things they don’t think they are excelling at. I notice a lot of my reports want to excel at everything they do. 

As a coach/manager, I’m a big fan of playing to your strengths. I find myself often having conversations with my reports/coachees and reminding them that operations is a team, and we all have a role to play. The analogy I like to use is, you can be an amazing quarterback, but it doesn’t mean you will be a great wide receiver, and you don’t have to be, because we have someone on the team who is a great wide receiver. If we all play to our strengths, we will be an unstoppable team. 

How do you know if you’ve had a successful one-on-one meeting? 

I look at coaching as a marathon, not a sprint. Some meetings are going to be more productive than others, but my main goal is to ensure that we are always moving towards our agreed-upon goals. I would say the best way to measure success is to ask your coachee what they found valuable from the session, if they can provide you at least one thing, I’d say it was successful. Similarly, I’ll reflect on my own to make sure I got something out of it too. It can be anything from more face time with a report to helping them problem solve or remove a major blocker.

What’s the most surprising/memorable conversation you’ve ever had in a one-on-one meeting?

The most memorable conversation I’ve ever had would be with my own coach shortly after I was promoted to a manager. I was facing pretty heavy imposter syndrome and was struggling to find my voice at the meetings I was now involved in. I was also now peers with managers that I had looked up to my entire professional career at Flipp. My coach said “You’ve earned a right to be at that table, you’re there for a reason, find what it is”. Hearing this gave me reassurance, and it empowered me to find what my strengths are, and play to them. Since then I have received feedback from my peers that I bring great insight to the team and they appreciate the voice I bring to meetings.

What’s the biggest mistake a manager can make in a one-on-one setting?

Put pressure on themselves to have all the answers. In my experience, the best coaches don’t have all of the answers. Instead, they ask the right questions to get their direct reports to come up with the answer themselves.

As a manager, I don’t think it is my job to give the best advice or provide life-saving tips or tricks, but rather I think it is to empower my coachee/report to figure out the answers on their own. 

What’s that saying, give a man a fish, and you feed him for a day. Teach a man to fish, and you feed him for a lifetime? That’s how I approach management. Instead of giving answers, I’d rather ask questions and share frameworks so that my report/coachee can problem solve independently.

What advice would you give to a new manager who’s about to run their first one-on-one meeting?

Come prepared to every meeting. Whether it is prepared questions, an agenda, or talking points, don’t walk into the meeting empty-handed. One-on-ones can be extremely valuable to both you and your direct report, but they are also quite a time commitment. I never want a coachee/report to leave a one-on-one feeling it was a waste of time. I think especially as a new manager, and running your first one-on-one, you likely haven’t built the rapport or trust needed to have a less structured one-on-ones, so in order to make the most of it come prepared. 

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Want to learn about how other people managers run one-on-one meetings? Check out these other interviews:

• Connor Bradley, Growth Team Lead at Jobber
• James Carr, Infrastructure Engineer Lead at Zapier
• Lorena Scott, Head of People Operations at Ritual

What to do next

Now that you've read this article, here are some things you should do:

1. Look into how Hypercontext can help you run effective one-on-ones.
2. Check out Hypercontext to see how it can help you run a high performing org.
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