Starting an Effective One On One Meeting

Work Jan 22, 2021

Meeting with your manager 1 on 1 is an opportunity to voice concerns, grow, and build rapport. So how do you start off strong, and make the most of it? This question is on my mind as I am starting with a different manager at work. How do I take advantage of this fresh start?

What are one-on-ones?

To begin with, we need to understand the basic purpose of one on ones in the professional world. As their name implies a one on one is where a manager meets with their direct report in a private environment.

It's a fundamental procedure for facilitating communication within a company. This is especially true for upwards communication in a hierarchical structure, allowing ideas and problems to bubble up from the bottom of the hierarchy to the top. Likewise it can be used for passing word down from top to bottom, or spreading news laterally in flat structures.

One of the most important aspects of one on ones is using them as a safe space for personal conversations, whether giving feedback or discussing sensitive issues. If you're familiar with the saying, "praise in public, criticise in private," then that privacy is often found in one on ones.

Even if you don't have problems that need privacy, holding regular one on ones builds trust before the problems come up. That way it's simpler to work through problems when they finally do arrive. It's easier to accept feedback if you have developed enough of a relationship with your manager to trust their judgement, and are familiar with their communication style.

Though one on ones are based around communication, that's not all there is to them. They allow you to design the relationship between your manager and yourself with intention. That is to say, as a direct report you can make of the meetings what you will.

For instance, they're a great opportunity for a direct report to focus on their own career and goals. They can ask for new project opportunities to work on, reflect on what has gone poorly, receive mentorship, or ask for resources such as training that allows them to better perform their job.

One on ones are also a great chance to present your manager with action items. Without action items, endless discussions that go nowhere are less than useful. Your manager can instead unblock impediments to your work, especially the administrative overhead kind. They can speak with others on your behalf, such as to raise concerns with the next level of management above them. Likewise, your manager may help you find action items for yourself to carry out.

Remember, a manager is a person trying to keep you productive despite any issues going on. Action items are how you and they carry this out. They are not a therapist or a friend.

Changing teams

I recently made a move at work that necessitated changing managers and starting a new series of one on one meetings. This relatively fresh start is a great time to reflect upon one on ones, and to implement better practises than I have been. Let's start with a look at how I got here:

My first manager was more of a technical leader than a manager. They brainstormed with me, explained technical problems, and guided me through routine problems I encountered. Our one on ones rarely touched upon my career aspirations. Nor did we have much in the way of mentorship going on, nor difficult conversations. The closest we ever came to difficult conversation was negotiating the transition from part-time work to full-time work.

At the time this management style was great, since this was my first professional manager. It was low stakes, straightforward, and friendly. We got to talk shop like the nerds we are. I learned the basics of professional polish, and I gradually overcame my reclusive anxieties.

Then came a reorganisation that brought along a new manager for me. They were completely separate from my technical lead. During our meetings we focused on the team's productivity, professional development, and project ownership.

This was my first opening to the broader world of professionalism, especially the fact that I was a professional who owned the outcomes of my projects. No longer was I just a lackey doing what I was told. I was responsible and accountable for the success (and failures) of my work. My manager helped me get a feel for the expectations on me, and most importantly he clarified what projects were important to the company.

A bit of advice I read a while back helped me understand that most employees spend their time working hard on things that the company and management don't notice or care about. Being aligned in goals with management is a key reason for my manager to have one on ones with me.

That said, I've kept my one on ones from becoming status updates on those important projects. We have other meetings that we can use for that. My one on ones are mine. Most often I drive the agenda for them, and use the time carefully to make the most of it. When else do I get to learn about professional conduct, or quiz people about work unrelated topics like 401ks, HSAs, communication, and interacting with HR?

Alas after only a few months with this second manager, I made the decision to change to a different team. I interviewed the manager for a team I wanted to join, liked what I saw, and made the jump. Now I just started official one on ones as a new member of the team – hence this post reflecting on them.

Advice and routine questions

Going into this new series of one on ones, I had a few bits of advice stuck in the forefront of my mind.

Talk about how to extract the most work from yourself
Use bullet points to hit the important highlights
Love the person, not the relationship

As far as extracting more work from yourself, your manager's goal should always be to support you in getting the most out of yourself. That means letting them know when you have problems, coming up with action plans to address them, and sticking to those plans. That does not always mean that they're pushing for more and ever more work – instead it's about recognising limits and staying sustainable. It's also your own responsibility to make sure you're doing what you can to stay productive.

Using bullet points should be a self-evident trick that has great impact. If you come prepared with an agenda on bullet points, you can make sure you talk about everything important to you.

Then "love the person, not the relationship" was a curious line my mom in law gave me about honesty. The focus is on saying what is necessary and important rather than masking the truth with relationship-soothing watering downs. If your manager needs to know something, they need to know it. Even if it strains your personal comfort and relationship with them; a small discomfort early is better than a large blowout later.

There are also a bunch of routine questions I'm already used to employing during one one ones:

For myself, "What's been going well/poorly?"
For my manager, "How is the team doing?"
"What are the team's priorities?"
"What's going on with the company?"
"How's life?"

It's helpful to use these questions as starting points to quickly move into specifics. It's important to avoid giving closed responses, which are terse and can leave the conversational flow stilted.

A giant list of many more questions to ask during one on ones

Primer questions for the first meetings

Since I'm starting with a new manager, I need more than just routine questions. I need an establishing character moment. Bringing professionalism to the table is part of it, as is establishing communication styles. I want my manager to understand where my goals are, that way they can find the overlap with their own goals and we can have common ground to work from.

I find that form of communication and understanding to be poetic. It's great when two people are in accord and working towards a shared goal.

Here's a few questions that I used to start it off:

"What makes 1 on 1s valuable to you?"

This was one of my very first segue questions, with good reason. Understanding what your cohort is seeking to gain from a one on one helps you reach accord sooner. It also helps you avoid situations where each side is working towards cross purposes.

For instance if I want to largely use one on one time to build rapport and get to know my manager personally, I should let them know that. That way they don't get focused on talking about just projects at work. Likewise I like to learn what they value, that way I can spend time helping them achieve it.

"What areas are there for me to grow into?"

This is dependent on my situation as I'm joining an established manager's team. One of the important questions on my mind is which niche will be my eventual home. Asking my manager makes sense, as they are familiar with the options and can help me assess the best match.

"What's your background? How did you get here?"

Whenever you're working in a team, one of the first points of orientation should be to learn about your teammates. You should learn their strengths, areas of expertise, and past experiences. One place to start is with their background.

To summarise it with the memorable words from a leadership workshop I attended: "If you're lost at sea, the first thing you want to find out is if anyone has experience with being rescued before."

Final Thoughts

I believe in cultivating a manager's viewpoint even if you have no interest in leadership – just like I believe everyone should know how to give and take orders, even if they have no intention of dealing with authority. Being able to understand both sides of a leadership interaction goes a long way towards making you more effective, whether you're a manager or a direct report.

Similarly, as a Domme I appreciate the benefits of learning to lead. The more I understand how people work, the better I can take care of my dearheart. If we structured our lives like an executive household, we'd use tools like one on ones to fit in quality time and gauge moods.

There are a lot of resources out on the internet about leading, and I'll leave off with this final one, an awesome list: